DETAILED ACTION
Notice of Pre-AIA or AIA Status
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Continued Examination Under 37 CFR 1.114
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on 07/18/25 has been entered.
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claims 22-23, 25-27, 29, 35-37, 40, 42, 45, 49, 51, 53-55, 60-79, 81, 83, 85-87, 92-103, 109-112, 114, 127-130, 132 are rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
Claims 22 and 71 recite “a water solvent” which is unclear. Do applicant’s merely mean water as the water solvent, or does “a water solvent” mean a miscible solvent and water mixture together is the “a water solvent” as claimed?
Claims 23, 25-27, 29, 35-37, 40, 42, 45, 49, 51, 53-55, 60-70, 72-79, 81, 83, 85-87, 92-103, 109-112, 114, 127-130, 132 are also rejected because they depend either directly or indirectly from the above claims and do not resolve the above ambiguities.
Double Patenting
The nonstatutory double patenting rejection is based on a judicially created doctrine grounded in public policy (a policy reflected in the statute) so as to prevent the unjustified or improper timewise extension of the “right to exclude” granted by a patent and to prevent possible harassment by multiple assignees. A nonstatutory double patenting rejection is appropriate where the conflicting claims are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg, 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); In re Goodman, 11 F.3d 1046, 29 USPQ2d 2010 (Fed. Cir. 1993); In re Longi, 759 F.2d 887, 225 USPQ 645 (Fed. Cir. 1985); In re Van Ornum, 686 F.2d 937, 214 USPQ 761 (CCPA 1982); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); In re Thorington, 418 F.2d 528, 163 USPQ 644 (CCPA 1969).
A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) or 1.321(d) may be used to overcome an actual or provisional rejection based on nonstatutory double patenting provided the reference application or patent either is shown to be commonly owned with the examined application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. See MPEP § 717.02 for applications subject to examination under the first inventor to file provisions of the AIA as explained in MPEP § 2159. See MPEP § 2146 et seq. for applications not subject to examination under the first inventor to file provisions of the AIA . A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b).
The filing of a terminal disclaimer by itself is not a complete reply to a nonstatutory double patenting (NSDP) rejection. A complete reply requires that the terminal disclaimer be accompanied by a reply requesting reconsideration of the prior Office action. Even where the NSDP rejection is provisional the reply must be complete. See MPEP § 804, subsection I.B.1. For a reply to a non-final Office action, see 37 CFR 1.111(a). For a reply to final Office action, see 37 CFR 1.113(c). A request for reconsideration while not provided for in 37 CFR 1.113(c) may be filed after final for consideration. See MPEP §§ 706.07(e) and 714.13.
The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The actual filing date of the application in which the form is filed determines what form (e.g., PTO/SB/25, PTO/SB/26, PTO/AIA /25, or PTO/AIA /26) should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission. For more information about eTerminal Disclaimers, refer to www.uspto.gov/patents/apply/applying-online/eterminal-disclaimer.
Claims 22-23, 25-27, 29, 35-37, 40, 42, 45, 49, 51, 53-55, 60-79, 81, 83, 85-87, 92-103, 109-112, 114, 127-130, and 132 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-23 of copending Application No. 18270799 (‘799), Frasetto (US20120264947, from IDS), Oguma et al. (EP1334956, from IDS), Smith (WO2009158258, from IDS), Liang (MS Thesis, 2018, from IDS), BE885657as evidenced by Schultz (J. Org. Chem., 1963, 28, 1140-1142). Although the claims at issue are not identical, they are not patentably distinct from each other because both ‘799 and the instant application are directed to methods of forming pyroxasulfone comprising oxidizing the same sulfur containing compound to a sulfone with peroxides/hydrogen peroxide and with the same organic solvents, acetonitrile, C1-C6 alcohols which overlap with the claimed alcohols and are different from the carboxylic acid, and wherein the reactions are performed at the same temperatures and with the same transition metal catalysts, e.g. tungsten, molybdenum, etc. and wherein an acid/acid catalyst is also used. ‘799 does not teach/claim wherein the side product sulfoxide is formed in less than 5% or wherein the transition metal catalysts are the specifically claimed sodium tungstate, sodium tungstate dihydrate, ammonium molybdate, tungstic acid/tungstic acid salts, molybdic acid and/or salts thereof, etc. of the claimed phase transfer catalyst or wherein the hydrogen peroxide is present in the claimed percentages or wherein the claimed steps I and II are also performed. However, these deficiencies in ‘799 are addressed by Frasetto, Oguma, ‘689, Liang, Smith, and ‘657.
Frasetto teaches oxidizing the sulfur atom of applicant’s (4) with sodium tungstate/sodium tungstate dihydrate (tungstates are tungstic acid salts) (claims 22, 24-27, 45-48, 52-54) and 30% hydrogen peroxide (claim 23) in water and acetic acid solvent, which has an acceptor number of 0 to 50 to yield applicant’s (5) wherein in applicant’s (4) R1 is methyl, R2 is CF3, R3 is CHF2 and R4 and R5 are both methyl in Frasetto, which reads on claims 22-27 (See [0170]; Example 9).
Frasetto teaches applicant’s step ii wherein the base used to form applicant’s compound (4) is sodium hydroxide which is an alkali metal hydroxide (See Example 9; [0168-0170]).
Frasetto teaches wherein their reactions can be formed under acid catalysis with acetic acid (See [0127-0128]).
Oguma teaches methods of preparing sulfones and sulfoxides wherein the claimed tungsten catalysts or molybdenum catalysts, specifically tungsten (which forms tungsten oxide in the presence of hydrogen peroxide), are used with hydrogen peroxide in water, wherein the hydrogen peroxide is used in amounts of at least 3 moles preferably at least 5 moles per mol of the metal or metal compound without upper limit, and organic solvents, specifically the claimed acetonitrile, ethyl acetate, methanol, ethanol, tert-butanol all of which read on the solvents claimed in applicant’s new claims 104-106, 108-118, 122-124, 126-136 and wherein the sulfone was selectively formed with the sulfoxide being formed in about 5.0% or less in most instances, even 1% or less in some examples and where tungsten/tungsten oxide was used as the catalyst as catalyst selection was important for selectively forming the sulfone compounds ([0006]; [0007-0017]; [0018-0020]; [0066-0069]; examples 1-4, 6). Oguma teaches using reaction temperatures of from -20 to 100 °C for the conversion of the sulfide to the sulfone and/or sulfoxide, and that selective oxidation to the sulfone (instantly desired compound) can be controlled over the formation of the sulfoxide compound by controlling the amount of hydrogen peroxide used in the reaction ([0067]). Oguma also teaches wherein phase-transfer catalysts can be used in the reactions, specifically if included Oguma teaches that they prefer quaternary ammonium salts and specifically prefer quaternary ammonium chlorides and quaternary ammonium hydrogen sulfates, including the claimed tetrabutyl ammonium hydrogen sulfate claimed in claims 63-65 and 95-97 ([0071-0072]; [0074]).
Liang teaches methods of making pyroxasulfone of high purity wherein the oxidation of the sulfur atom to the sulfone can be accomplished in various solvents including DMF, acetonitrile, and methanol which read on the claimed solvents, and wherein the same conversion of applicant’s (4) to (5) is accomplished with hydrogen peroxide and the same solvents instantly claimed, the examiner is not seeing a metal catalyst in the reaction sequence (see English abstract; pg. 48-51, Table 3.8.1). Because Liang teaches accomplishing the same reactions with the same (4) being oxidized to (5) using hydrogen peroxide as the oxidant and wherein the same acetonitrile and methanol can be used as solvent.
‘689 also broadly teaches applicant’s compound (2), because ‘689 broadly teaches halogenating structurally similar/same alcohols to applicant’s formula (1) to form compounds similar/same to applicant’s formula (2), wherein the primary alcohol is reacted with a halogenating agent, e.g. chlorinating agent, specifically thionyl chloride which reads on claims 40 and 42 (See scheme in col. 180, conversion of [20] to [21] wherein applicant’s groups are as defined in the instant claims 43-44 as per Col. 180, ln. 55-67; see ~49th compound table 3, col. 23-24 which would be/could be made by applicant’s step i as discussed above and subsequent steps), and ‘689 further teaches wherein in applicant’s formula (1), R1 is/can be methyl, R2 is/can be trifluoromethyl, R3 is/can be difluoromethyl, and wherein in formula (2) X1 is chlorine atom and R1-R3 are/can be as defined in the instant claims (See scheme in col. 180, conversion of [20] to [21] wherein Y is applicant’s claimed substituted pyrazole ring which would be used to make applicant’s 5 which is expressly taught, see also Col. 180, ln. 55-67; see 49th compound table 3, col. 23-24 which would be/could be made by applicant’s step i as discussed above).
Smith teaches the step of condensing applicant’s (3) with different alkyl chloride compounds which also are condensed using base, specifically alkali metal hydroxides and specifically sodium hydroxide (see scheme 6) which reads on claims 36-37, specifically Smith broadly teaches compounds of applicant’s formula (3) which are reacted with other heterocyclic compounds having a primary alkyl halide kind of structurally similar to applicant’s formula (2) which form condensed compounds having the claimed S-CH2 bond linking the two heterocycle groups (See scheme 6; pg. 26, ln. 3-23). Smith teaches wherein applicant’s R4 and R5 can both be methyl (which correspond to Smith’s R1 and R2), and Smith teaches wherein the base used in step ii is an alkali metal hydroxide, specifically wherein the base can be sodium hydroxide (See scheme 6; pg. 26, ln. 3-23; claims).
‘657 teaches that it was known to gently oxidize sulfur atoms to sulfones via hydrogen peroxide without oxidizing other parts of complex molecules using tungsten or molybdenum salt catalysts/molybdic acid salts (as evidenced by Schultz (J. Org. Chem., 1963, 28, 1140-1142 cited in ‘657, see entire document; right col. Pg. 1140 bridging paragraph-left col. 1141; entire left col. Pg. 1141-top 3 lines of right col. 1141; left col. Pg. 1142, last 5 lines), and phase transfer catalysts, specifically quaternary ammonium phase transfer catalysts more specifically tetrabutylammonium salts (See entire document; claims; paragraph starting with The applicant has surprisingly found through the end of the paragraph/section starting with, a cation such as Na, K, an ammonium, a trialkylammonium ion or a tetraalkylammonium ion, for example a tetrabutylammonium ion…”).
It would have been obvious to one of ordinary skill in the art at time of the instant filing to have formed the claimed method when looking to copending Application No. 18270799 and the combined references because ‘799 teaches that it was known to form the same active using the same oxidation step with the same acids and the same peroxide/hydrogen peroxide and the same solvent and the same temperatures. Further, it was known to use the same transition metal catalysts as claimed by ‘799 and the secondary references discussed above and to perform the same steps ii and i claimed as taught by the secondary references above, and it was known in the art (Oguma and Liang) to adjust the conditions by maximizing the amounts of hydrogen peroxide and concentration of aqueous hydrogen peroxide used to oxidize sulfur to selectively form the desired sulfone and to limit the amount of the sulfoxide which is formed as is instantly claimed and the newly claimed solvents were known in the art to be useful for the oxidation of sulfide to sulfone and in the case of Oguma to limit the amount of the sulfoxide that is formed in these reactions. Thus, one of ordinary skill in the art would realize that the instantly claimed method is an obvious variant of the method disclosed in copending application 18270799 when taken in view of the secondary references cited above.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Claim Rejections - 35 USC § 103
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claim(s) 22-23, 25-27, 29, 45, 49, 51, 53-54, 60-79, 81, 83, 85-86, 92-103, 109-112, 114, 127-130, 132 is/are rejected under 35 U.S.C. 103 as being unpatentable over Frasetto (US20120264947, from IDS), He et al. (Phosp., Sulfur, and Silicon, 2012, 187, 822-830), Oguma et al. (EP1334956, from IDS), Liang (MS Thesis, 2018, from IDS).
Determination of the scope and content of the prior art
(MPEP 2141.01)
Regarding claims 22-23, 25-27, 45, 49, 51, 53-54, 71, 74-77, 79, 81, 83, 85-86, Frasetto teaches oxidizing the sulfur atom of applicant’s (4) with sodium tungstate/sodium tungstate dihydrate (tungstates are tungstic acid salts) (claims 22, 24-27, 45-48, 52-54) and 30% hydrogen peroxide (claim 23) in water and acetic acid solvent, which has an acceptor number outside of applicant’s claimed range, but which yields applicant’s (5) wherein in applicant’s (4) R1 is methyl, R2 is CF3, R3 is CHF2 and R4 and R5 are both methyl in Frasetto, which reads on claims 22-27 (See [0170]; Example 9).
Regarding claims 61, Frasetto teaches wherein their reactions can be formed under acid catalysis with acetic acid (See [0127-0128]).
Ascertainment of the difference between prior art and the claims
(MPEP 2141.02)
Regarding claims 22-23, 25-27, 29, 45, 49, 51, 53-54, 60-79, 81, 83, 85-86, 92-103, 109-112, 114, 127-130, 132, Frasetto does not teach wherein the solvent is other than acetic acid, specifically the instantly claimed alcohols and nitriles, more specifically wherein the solvent is acetonitrile or methanol, etc. or wherein the method leads to less than 5% of the sulfoxide compound (6), specifically less than 3%, or is 1% or less of compound (6) or the claimed equivalents of hydrogen peroxide which are used as compared to the sulfur substrate being oxidized. Frasetto also does not teach the instantly claimed temperatures. However, these deficiencies in Frasetto are addressed by Liang, He, Oguma.
Regarding the instant claims, Liang teaches methods of making pyroxasulfone of high purity wherein the oxidation of the sulfur atom to the sulfone can be accomplished in various solvents including DMF, acetonitrile, and methanol which read on the claimed solvents, and wherein the same conversion of applicant’s (4) to (5) is accomplished with hydrogen peroxide and the same solvents instantly claimed, the examiner is not seeing a metal catalyst in the reaction sequence (see English abstract; pg. 48-51, Table 3.8.1). Because Liang teaches accomplishing the same reactions with the same (4) being oxidized to (5) using hydrogen peroxide as the oxidant and wherein the same acetonitrile and methanol can be used as solvent.
Regarding claims 22-23, 25-27, 29, 45, 49, 51, 53-54, 60-79, 81, 83, 85-86, 92-103, 109-112, 114, 127-130, 132, He teaches selectively oxidating sulfur/sulfides to sulfones using hydrogen peroxide and sodium tungstate and wherein the amount of sulfoxide formed in the reaction is less than 5%, specifically less than 3%, and the reaction temperature is 50-60 °C, the hydrogen peroxide used is 30% hydrogen peroxide and the peroxide is used in 2.5 equivalents with respect to 1 equivalent of the sulfide substrate being oxidized (See general procedure for the oxidation to sulfones pg. 828-830; pg. 836-828 oxidation to sulfones section and conclusion sections).
Regarding claims 22-23, 25-27, 29, 45, 49, 51, 53-54, 60-79, 81, 83, 85-86, 92-103, 109-112, 114, 127-130, 132, Oguma teaches methods of preparing sulfones and sulfoxides wherein the claimed tungsten catalysts or molybdenum catalysts, specifically tungsten (which forms tungsten oxide in the presence of hydrogen peroxide), are used with hydrogen peroxide in water, wherein the hydrogen peroxide is used in amounts of at least 3 moles preferably at least 5 moles per mol of the metal or metal compound without upper limit, and organic solvents, specifically acetonitrile, ethyl acetate, alcohols such as methanol, ethanol, tert-butanol all of which read on new claims 104-106, 108-118, 122-124, 126-136 and wherein the sulfone was selectively formed with the sulfoxide being formed in about 5.0% or less in most instances, even 1% or less in some examples and where tungsten/tungsten oxide was used as the catalyst as catalyst selection was important for selectively forming the sulfone compounds ([0006]; [0007-0017]; [0018-0020]; [0066-0069]; examples 1-4, 6). Oguma teaches using reaction temperatures of from -20 to 100 °C for the conversion of the sulfide to the sulfone and/or sulfoxide, and that selective oxidation to the sulfone (instantly desired compound) can be controlled over the formation of the sulfoxide compound by controlling the amount of hydrogen peroxide used in the reaction ([0067]). Oguma also teaches wherein phase-transfer catalysts can be used in the reactions, specifically if included Oguma teaches that they prefer quaternary ammonium salts and specifically prefer quaternary ammonium chlorides and quaternary ammonium hydrogen sulfates, including the claimed tetrabutyl ammonium hydrogen sulfate claimed in claims 63-65 and 95-97 ([0071-0072]; [0074]). Oguma also teaches that it was known in the art to use phenyl phosphate/phenylphosphonic acid with sodium tungstate to catalyze the oxidation of sulfides to sulfones (and sulfoxides) (See [0004]).
Finding of prima facie obviousness
Rationale and Motivation (MPEP 2142-2143)
It is obvious for one of ordinary skill in the art at the time of the instant filing to form the claimed compound of formula (5) by changing the solvent of Frasetto for the instantly claimed acetonitrile or C1-C4 alcohols which are taught by Liang, Oguma and ‘689 to be useful for performing the same types of oxidation reactions of sulfur atoms with aqueous hydrogen peroxide of the same concentrations instantly claimed and with sodium tungstate as catalyst. One of ordinary skill in the art would be motivated to change the acetic acid solvent of Frasetto for the acetonitrile solvents of Oguma, ‘689, or Liang because for instance the claimed acetonitrile and/or alcohol solvents claimed were known to be alternative solvents for the claimed sulfur to sulfone oxidation reactions with the same catalysts and oxidants for forming sulfones, in that the reaction will proceed in these solvents especially since the instant claims do not require any specific yields of the pyroxasulfone (5) to be obtained and merely require less than 5%, specifically less than 1% of the sulfoxide (6) byproduct to be present.
Regarding the claimed temperature ranges it would have been obvious to optimize the temperatures of the reactions taught by Frasetto and the combined references in order to form applicants (5) via step (iii) to the instantly claimed ranges because ‘689 teaches forming applicant’s (5) and teaches that the reaction temperatures in the steps to getting to (5) are done at any temperature from 0 °C and the reflux temperatures of the reaction systems used, preferably 10 °C to 100 °C, and Oguma and He teach that the claimed temperature ranges were known temperatures for selective oxidation of sulfur to sulfones. Thus, it would be obvious for one of ordinary skill in the art to optimize the temperatures of the reaction to the claimed temperature ranges in order to afford the highest yields of (5) as the claimed temperature ranges were known in the art for being useful for forming the claimed compound and because optimization of the temperature of a reaction in order to afford the most effective yields is something that one of ordinary skill in the art routinely does when developing synthetic reactions to a desired product because one of ordinary skill in the art would want to produce as much of the desired product as possible for cost effectiveness.
Regarding using the instantly claimed phase transfer catalysts and/or acid catalysts, specifically the tetrabutylammonium hydrogen sulfate in reaction (iii) or the phenyl phosphate that are instantly claimed, it would have been obvious to use the claimed phase transfer catalysts and/or acid catalysts because as discussed above it was already known in the art to use the specifically claimed phase transfer catalysts and phenyl phosphate in sulfur oxidations to sulfones as is taught by Oguma.
Regarding the claimed ratios/equivalents of hydrogen peroxide being used it would have been obvious to one of ordinary skill in the art to optimize the amount of oxidant/hydrogen peroxide necessary in the oxidation reactions of Frasetto in order to selectively form the claimed sulfones with very little to no formation of the sulfoxide compound as is instantly claimed because Oguma and He teach that by adjusting the amount of hydrogen peroxide used in the oxidation reactions of sulfur atoms to sulfones can be selectively formed with little to no sulfoxide formed as is instantly claimed. Thus, it would be obvious to optimize the amount of catalyst and peroxide present in the reaction to selectively form the sulfone with little to no sulfoxide formed as is instantly claimed because such selective sulfur oxidations were known in the art as taught by the secondary references, e.g. Oguma, etc. as discussed above. Liang further teaches that hydrogen peroxide solutions were known to be useful for sulfur to sulfone oxidation of applicant’s (4) to (5) in various solvents and with the same catalysts instantly claimed.
Regarding using the claimed solvents of claims 104-139, it would have been obvious to one of ordinary skill in the art at the time of the instant filing to have selected the claimed solvents for use as solvents in the oxidation reaction taking the sulfur atom to the claimed SO2 group because each of the claimed solvents was already known in the art to be useful as solvents for the same oxidation reaction of oxidizing sulfur atoms in organic compounds to SO2 groups (i.e. a sulfone). It would have been obvious to one of ordinary skill in the art to at least try the claimed solvents in the oxidation of the sulfur atom to the SO2 group of Frasetto because each of the claimed solvents was already taught in the prior art to be useful as a reaction solvent in the same transformation/oxidation reaction which oxidizes a sulfur atom to an SO2 group as is taught by Liang, Oguma, and ‘689 as discussed above. It is known in the art to do solvent screens in developing the most effective reaction conditions for a specific transformation by looking to the prior art for the same reaction/transformation, in this case the oxidation of an S atom to an SO2 group in an organic compound, e.g. the claimed conversion (4) to (5) as taught by Frasetto in order to see what worked for other related/similar transformations and to use these solvents as starting points for screening/developing a more effective reaction sequence. Further, one of ordinary skill in the art would be motivated to screen the conditions disclosed by Liang, Oguma, and He for use in the transformation of (4) to (5) in Frasetto in order to provide a transformation which provides a more selective oxidation to the sulfide thereby leading to less of the undesired byproduct (6) and therefore a cleaner/more pure product (5) for use as a herbicide which would be beneficial and would have been obvious to one of ordinary skill in the art in effort to find a more effective synthesis for the formation of the desired (5) from starting material (4). While solvent screening can be time consuming, it is something that one of ordinary skill in the art routinely does in order to determine the most effective solvents for a given reactant, catalyst, etc. and all of the claimed solvents were already known in the art to allow the claimed transformation of the S to SO2 group in the same or similar substrates as taught by the combination of secondary prior art documents.
In light of the forgoing discussion, the Examiner concludes that the subject matter defined by the above claims would have been obvious to one of ordinary skill in the art within the meaning of 35 USC 103(a).
From the teachings of the references, it is apparent that one of ordinary skill in the art would have had a reasonable expectation of success in producing the claimed invention. Therefore, the invention as a whole would have been prima facie obvious to one of ordinary skill in the art at the time the invention was made, as evidenced by the references, especially in the absence of evidence to the contrary.
Claims 35-37 and 40, 42 is/are rejected under 35 U.S.C. 103 as being unpatentable over Frasetto (US20120264947, from IDS), He et al. (Phosp., Sulfur, and Silicon, 2012, 187, 822-830), Oguma et al. (EP1334956, from IDS), Liang (MS Thesis, 2018, from IDS) as applied to claims 22-23, 25-27, 29, 45, 49, 51, 53-54, 60-79, 81, 83, 85-86, 92-103, 109-112, 114, 127-130, 132 above and further in view of US7238689 (‘689) and Smith (WO2009158258, from IDS).
Determination of the scope and content of the prior art
(MPEP 2141.01)
The combined references together teach the inventions/methods of claims 22-23, 25-27, 29, 45, 49, 51, 53-54, 60-79, 81, 83, 85-86, 92-103, 109-112, 114, 127-130, 132 as discussed above and incorporated herein.
Regarding claims 35-37, Frasetto teaches a similar reaction to applicant’s step ii wherein the base used to form a structurally similar compound to applicant’s compound (4) from the reaction of a compound structurally similar to (2) (it lacks the CH2-Br or CH2-Cl group) and the claimed (3) is sodium hydroxide which is an alkali metal hydroxide, and Frasetto teaches applicant’s (3) (See entire document; Example 9; [0168-0170]; [0066, Scheme 2a]).
Ascertainment of the difference between prior art and the claims
(MPEP 2141.02)
Regarding claims 35-37, 40 and 42, the combined references do not actually teach the reaction of step ii occurring with applicant’s specifically claimed compound (3) and (2) or the claimed step i. However, these deficiencies in the combined references are addressed by ‘689 and Smith.
Regarding claims 40 and 42, ‘689 teaches methods of forming pyroxasulfone and specifically teaches forming pyroxasulfone (see Table 3, col. 23-24, ~ ln. 49th or 50ish in the table wherein R1 and R2 are methyl, R3 and R4 are H, n is 2, R5 and R6 are H, R29 is CF3, R30 is OCHF2 and R28 is methyl) and therefore broadly teaches applicant’s compound (2), because ‘689 broadly teaches halogenating structurally similar/same alcohols to applicant’s formula (1) which would have to form compounds similar/same to applicant’s formula (2), wherein the primary alcohol is reacted with a halogenating agent, e.g. chlorinating agent, specifically thionyl chloride which reads on claims 40, 42 (See scheme in col. 180, conversion of [20] to [21] wherein applicant’s groups are as defined in the instant claims 43-44 as per Col. 180, ln. 55-67; see ~49th or 50th compound table 3, col. 23-24 which would be/could be made by applicant’s step i as discussed above and subsequent steps), and ‘689 further teaches wherein in applicant’s formula (1), R1 is/can be methyl, R2 is/can be trifluoromethyl, R3 is/can be difluoromethyl, and wherein in formula (2) X1 is chlorine atom and R1-R3 are/can be as defined in the instant claims (See scheme in col. 180, conversion of [20] to [21] wherein Y is applicant’s claimed substituted pyrazole ring which would be used to make applicant’s 5 which is expressly taught, see also Col. 180, ln. 55-67; see 49th compound table 3, col. 23-24 which would be/could be made by applicant’s step i as discussed above).
Smith teaches the step of condensing applicant’s (3) with different alkyl chloride compounds which also are condensed using base, specifically alkali metal hydroxides and specifically sodium hydroxide (see scheme 6) which reads on claims 35-37, specifically Smith broadly teaches compounds of applicant’s formula (3) which are reacted with other heterocyclic compounds having a primary alkyl halide structurally similar to applicant’s formula (2) which form condensed compounds having the claimed S-CH2 bond linking the two heterocycle groups (See scheme 6; pg. 26, ln. 3-23). Smith teaches wherein applicant’s R4 and R5 can both be methyl (which correspond to Smith’s R1 and R2), and Smith teaches wherein the base used in step ii is an alkali metal hydroxide, specifically wherein the base can be sodium hydroxide (See scheme 6; pg. 26, ln. 3-23; claims).
Finding of prima facie obviousness
Rationale and Motivation (MPEP 2142-2143)
It would have been obvious to one of ordinary skill in the art at the time of the instant filing to have performed applicant’s step ii with the claimed (2) and (3) to form (4) as is instantly claimed because it was known to use the claimed base to form (4), and applicant’s (2) and (3) were known as is taught by ‘689 and Smith. One of ordinary skill in the art would have been motivated to perform the claimed step(s) because these steps were known in the art to be useful for forming the claimed compounds and structurally similar compounds as is taught by the combined references as discussed above and by using the (2) and (3) as taught by ‘689 and Smith would allow one another obvious way to get to compound 4 for oxidation to (5) as each of these compounds was known in the art and the reaction of getting from 2 and 3 to (4) is taught by Smith in forming similar compounds. Thus, it would be obvious to use this step in place of Frasetto’s step to get to (4) in order to provide an additional effective means of forming the intermediate (4) to then oxidize to pyroxasulfone (5), especially since Smith teaches good yields and reactions using the sodium hydroxide with applicant’s (3) in order to form similar compounds to (4) and applicant’s (2) was known as taught by ‘689.
It also would have been obvious for one of ordinary skill in the art to add applicant’s step i into the method of Frasetto and the combined references for forming formula (5) because it was known in the art to form formula (2) by halogenating, specifically chlorinating with thionyl chloride applicant’s formula (1) as is taught by ‘689 because ‘689 teaches applicant’s formula (5) and broadly teaches that applicant’s (2) can be formed via applicant’s (1). One of ordinary skill in the art would want to form formula (2) en route to formula (5) in order to provide a new effective route into the known herbicide pyroxasulfone which is applicants formula (5).
Claim(s) 55 and 87 is/are rejected under 35 U.S.C. 103 as being unpatentable over Frasetto (US20120264947, from IDS), He et al. (Phosp., Sulfur, and Silicon, 2012, 187, 822-830), Oguma et al. (EP1334956, from IDS), and Liang (MS Thesis, 2018, from IDS) as applied to claims 22-23, 25-27, 29, 45, 49, 51, 53-54, 60-79, 81, 83, 85-86, 92-103, 109-112, 114, 127-130, 132 above and further in view of BE885657 (‘657) (as evidenced by Schultz (J. Org. Chem., 1963, 28, 1140-1142 cited in ‘657)).
Determination of the scope and content of the prior art
(MPEP 2141.01)
The combined references together teach the inventions/methods of 22-23, 25-27, 29, 45, 49, 51, 53-54, 60-79, 81, 83, 85-86, 92-103, 109-112, 114, 127-130, 132 as discussed above and incorporated herein.
Ascertainment of the difference between prior art and the claims
(MPEP 2141.02)
Regarding claims 55 and 87, Frasetto does not teach wherein the metal salts used to catalyze step iii are molybdic acid or salts thereof, etc. However, these deficiencies in Frasetto are addressed by ‘657 (as evidenced by Schultz).
‘657 teaches that it was known to gently oxidize sulfur atoms to sulfones via hydrogen peroxide without oxidizing other parts of complex molecules using tungsten or molybdenum salt catalysts/molybdic acid salts (as evidenced by Schultz (J. Org. Chem., 1963, 28, 1140-1142 cited in ‘657, see entire document; right col. Pg. 1140 bridging paragraph-left col. 1141; entire left col. Pg. 1141-top 3 lines of right col. 1141; left col. Pg. 1142, last 5 lines)), and phase transfer catalysts, specifically quaternary ammonium phase transfer catalysts more specifically tetrabutylammonium salts (See entire document; claims; paragraph starting with The applicant has surprisingly found through the end of the paragraph/section starting with, a cation such as Na, K, an ammonium, a trialkylammonium ion or a tetraalkylammonium ion, for example a tetrabutylammonium ion…”).
Finding of prima facie obviousness
Rationale and Motivation (MPEP 2142-2143)
Regarding using the claimed molybdic salts to catalyze reaction (iii), it would have been obvious to one of ordinary skill in the art that the claimed molybdic salts could be used to catalyze the oxidation of the S to SO2 with peroxide as taught by Frasetto and the combined references because ‘657 as evidenced by Schultz teaches that the claimed salts were already known in the art to be useful for catalyzing the oxidation reaction of sulfur atoms with hydrogen peroxide and as such it would be obvious to substitute these other known metal catalysts, e.g. molybdic salts, for the sodium tungstate/sodium tungstate dihydrate of the combined references in order to develop the instantly claimed method because all of the claimed salts/metal salts were already known in the art to be useful for catalyzing the oxidation of sulfur atoms to sulfones with hydrogen peroxide.
Response to Arguments/Remarks
Applicant’s amendments to the claims have overcome the previous 112(d) rejections.
Applicant’s new claims have prompted the new/revised grounds of rejection presented herein. Applicant’s arguments with respect to the previous rejections have been fully considered but are not persuasive at this time.
Applicants first argue the double patenting rejection and they argue that a double patenting rejection is based on the claims only that in comparing the claims of copending ‘799 to the instant claims it is clear that the subject matter is patentably distinct because the instantly claimed method has been amended to exclude acetic acid. The examiner respectfully disagrees because this is an obviousness double patenting rejection and as such the incorporation of secondary references which in combination with the claims of the copending ‘799 patent together render the instantly claimed method obvious are appropriate, specifically since it was known to use the claimed solvents instead of acetic acid to run the claimed reaction as is taught by the secondary references Oguma and/or He and the new reference Liang above. Thus, it would be obvious to substitute the acetic acid of ‘799 for the claimed solvents based on the teachings of the secondary references as discussed above as it is known to do solvent/reaction condition surveys in order to develop the most effective reaction conditions for a desired reaction. This is something that one of ordinary skill in the art routinely does in reaction methodology development.
Applicants argue each of the references used in the double patenting rejection individually and first argue that ‘799 and the instantly claimed invention differ because ‘799 uses a acetic acid as a solvent which has been excluded from the instantly claimed solvent. The examiner respectfully points out that nothing in the instant claims excludes the use of a carboxylic acid in the instant method as the instant claims use comprising language which is open-ended and does not exclude anything from the claimed method. Further, in the later dependent claims of the instant method are performed in the presence of an acid catalyst and this acid catalyst of claim 61 is not limited and therefore includes/reads on the carboxylic acid of ‘799 especially since ‘799 never discloses or specifically claims a specific amount of the carboxylic acid in their independent claim and that instant claims do not limit the amount of acid which can be present in the instantly claimed method because the comprising language does not exclude acids in any amount from the instantly claimed method.
Regarding the 103 rejection of record, applicant’s amendments have prompted the revised grounds of rejection presented herein. Applicant’s amendments have been fully considered and insofar as they pertain to the revised grounds of rejection are presented herein.
Applicants argue that the instant claims are not obvious over the prior art of record and that they have provided three declarations to establish why one of ordinary skill in the art would not have been motivated to modify Frasetto with Oguma, etc. The examiner respectfully points out that that under further consideration the examiner still believes that Frasettto and Oguma and/or He when taken in view of Liang do still render the instantly claimed method obvious for the reasons which are discussed above and incorporated herein.
Applicants argue that the specification in light of the additional examples provided within the declarations filed on 07/18/25 demonstrate that the reaction of similar substrates to the final product pyroxasulfone and gave poor results under the claimed conditions. Therefore, applicants argue that when the chemical structure of the raw material is different reactivity is significantly different and they argue that there is no motivation to combine prior art references which use raw materials with different chemical structures. Applicants argue that because the reactivity of the substrates/reactants in He and Oguma is different from the claimed compounds or different from the tested examples that it would not have been obvious to switch out the conditions of Frasetto for the claimed reaction conditions which are taught by Oguma and/or He. The examiner respectfully points out that the claimed solvents were also known to be used in screens for the claimed substrates/the claimed step iii reaction as is taught by Liang. While Liang prefers DMF they do demonstrate that acetonitrile and methanol do form the claimed pyroxasulfone and the instant method does not require any the reaction to yield any specific amounts of pyroxasulfone. Thus, Liang can be relied upon for all it teaches because, “A reference may be relied upon for all that it would have reasonably suggested to one having ordinary skill in the art, including nonpreferred embodiments.” Merck & Co. v.Biocraft Labs., Inc. 874 F.2d 804, 10 USPQ2d 1843 (Fed. Cir. 1989), cert. denied, 493 U.S. 975 (1989). Disclosed examples and preferred embodiments do not constitute a teaching away from a broader disclosure or nonpreferred embodiments. In re Susi, 440 F.2d 442, 169 USPQ 423 (CCPA 1971). “A known or obvious composition does not become patentable simply because it has been described as somewhat inferior to some other product for the same use.” In re Gurley, 27 F.3d 551, 554, 31 USPQ2d 1130, 1132 (Fed. Cir. 1994). Thus, the examiner maintains that because the claimed acetonitrile and methanol solvents have been used by Liang for the same transformation it would be obvious to try switching the acetic acid of Frasetto out for the acetonitrile, methanol, etc. of Liang, Oguma, and He in order to provide additional means of synthesizing pyroxasulfone especially since Oguma teaches that the claimed conditions provide selective oxidation of the sulfur atom to the sulfone with very little to no sulfoxide being formed just as in the claimed reaction process.
Oguma is appropriate prior art because it is known in the art when developing reaction conditions for a particular transformation, in this case the oxidation of the sulfide compound to a sulfone it is known in the art to look to prior art which accomplishes this transformation for appropriate solvents, reaction conditions, etc. which can be used as a starting point for reaction screening in order to find the most effective conditions for performing/developing the most effective methods for accomplishing the desired reaction/transformation. Thus, whether or not Oguma uses the same substrate Oguma is prior art for all it teaches, specifically that it was known in the art to prepare sulfones with the claimed tungsten catalysts or molybdenum catalysts, specifically tungsten (which forms tungsten oxide in the presence of hydrogen peroxide), are used with hydrogen peroxide in water, wherein the hydrogen peroxide is used in amounts of at least 3 moles preferably at least 5 moles per mol of the metal or metal compound without upper limit, and organic solvents, specifically acetonitrile, ethyl acetate, etc. as discussed above which read on new claims 104-106, 108-118, 122-124, 126-136 and wherein the sulfone was selectively formed with the sulfoxide being formed in about 5.0% or less in most instances, even 1% or less in some examples and where tungsten/tungsten oxide was used as the catalyst as catalyst selection was important for selectively forming the sulfone compounds, and Oguma teaches using temperatures which overlap those instantly claimed. Thus, it would be obvious for one of ordinary skill in the art to look to the conditions taught by Oguma for forming sulfone compounds selectively when oxidizing sulfides in order to limit the amount of sulfoxides formed because Oguma teaches these types of selective oxidations such as those instantly claimed are accomplished with the same/overlapping scope of solvents, temperatures and transitional metal catalysts with the same hydrogen peroxide as claimed in the same/overlapping ratios. Thus, one of ordinary skill in the art would be motivated to use the conditions taught by Oguma for selectively formulating sulfones from sulfides in order to more effectively perform the reaction sequence taught by Frasetto in order to make more pure pyroxasulfone from that formed from prior art methods by reducing the amount of the sulfoxide byproduct that is formed especially since it was already known to perform such selective sulfide to sulfone oxidations in other compounds as is taught by Oguma. This is further supported by the inclusion of the prior art Liang which does teach that these solvents do work for forming pyroxasulfone. Thus, the combination remains proper and does not use impermissible hindsight because it must be recognized that any judgment on obviousness is in a sense necessarily a reconstruction based upon hindsight reasoning. But so long as it takes into account only knowledge which was within the level of ordinary skill at the time the claimed invention was made, and does not include knowledge gleaned only from the applicant's disclosure, such a reconstruction is proper. See In re McLaughlin, 443 F.2d 1392, 170 USPQ 209 (CCPA 1971).
Applicants results presented from the declaration on pg. 20-21 of applicant’s response have been reviewed. The examiner first respectfully points out that nothing in the instantly claimed methods requires a good yield of pyroxasulfone. It only requires that the byproduct be formed in amounts of less than 5% specifically less than 1% as claimed in later dependent claims. The examiner notes that while close compounds do not always work to provide the sulfone product in good yields, the examiner does note that good yields of the sulfone are not required by the instantly claimed method. The claimed method only requires that (6) the sulfoxide by product be formed in less than 5%, specifically less than 1% as in later claims. Applicant’s further argue that Frasetto itself achieve low yield, e.g. 33% again the examiner respectfully points out the instant claims do not require the yield of any specific amounts of (5) pyroxasulfone contrary to applicants arguments. Further applicants good results, specifically their high selectivity of pyroxasulfone (5) vs the sulfoxide byproduct (6) were actually obtained with specific amounts of specific tungsten or molybdenum catalysts, specific amounts of hydrogen peroxide, and specific amounts of solvents, at specific temperatures to achieve the less than 5% pyroxasulfone.
Applicant’s again point to the fact that the claimed conditions were also used in structurally more complex pyroxasulfone analogs of Recsei. The examiner respectfully again points out that this would also renders the claimed method obvious because the instant claims do not actually require any specific yield of pyroxasulfone to be obtained as long as the reaction contains less than 5% of (6) the sulfoxide byproduct. The examiner understands that applicants may not have expected their yields by performing the conditions of Recsei on their (4) to achieve (5) with the high selectivity. However, it routine in the art to use/try reaction conditions which perform the same reaction sequence and which have substrates as closely related to yours as possible in order as starting points to develop the most effective reaction conditions, as reaction optimization is something that one of ordinary skill in the art routinely does. Thus, the examiner is not persuaded that applicants results are necessarily unexpected when taken in view of Recsei because Recsei is essentially reacting a basically dimerized pyroxasulfone and getting good results, and as such these conditions would be expected to also be useful for oxidizing monomeric instantly claimed (4) to produce the monomeric instantly claimed compound (5).
Thus, the examiner respectfully points out that a specific yield is not required by applicant’s claims nor is there any safety requirement/limitation in applicant’s claims. Applicants argue that obviousness cannot be established by combining teachings of the prior art to produce the claimed invention absent some teaching…supporting the combination, and they argue that because Oguma and He do not teach the same substrate being oxidized that the examiner is using impermissible hindsight. The examiner respectfully disagrees and respectfully points out that there is teaching/motivation to combine the instantly claimed references in order to form the claimed method because Frasetto and ‘689 are both directed to forming the claimed herbicide pyroxasulfone and the prior arts Oguma and He are in the same field of endeavor because they are addressed to the same problem as the instant invention, specifically selective oxidation of sulfides to sulfones with minimal sulfoxide byproduct. As discussed above, especially with the added Liang it was known in the art to use the same solvents, with the same transition metal catalysts and hydrogen peroxide in overlapping ratios to those instantly claimed to selectively form sulfones with minimal formation of sulfoxide byproducts just as is instantly claimed and desired as is taught by Oguma and He. Thus, it would be obvious to start with known solvents, catalysts and hydrogen peroxide in the overlapping ratios as taught by Liang, Oguma and He for optimizing the methods of pyroxasulfone of Frasetto in order to develop a more selective method for the sulfide to sulfone transformation with minimal formation of the sulfoxide byproduct by using the methods taught by Liang, Oguma and He as this is a benefit of the sulfide to sulfone oxidation methods disclosed in these references as discussed above. Thus, whether or not the sulfide substrates which are oxidized in Oguma and He are simpler than those instantly claimed and/or taught by Frasetto, etc. it is still obvious to use these references as a starting point for developing the claimed method and for optimizing the method of Frasetto by changing the reaction solvent, etc. for those disclosed by Oguma and He because those solvents were useful in more/highly selective oxidations of sulfides to sulfones with minimal formation of the sulfoxide which is an undesired byproduct of the instant reaction. Thus, one of ordinary skill in the art would be motivated to alter known methods of oxidizing the sulfide intermediate on the way to the desired pyroxasulfone compound in order to more selectively form pyroxasulfone the desired herbicidal product over the undesired pyraoxasulfoxide byproduct and one of ordinary skill in the art would first look to other methodology papers where others have selectively performed this same oxidation and would use those conditions as a starting point/obvious to try in order to optimize their own processes just as proposed by the examiner above and that is why Liang, Oguma and He are properly used as secondary references as they are solving the same problem as applicants, in that they too desire a more selective sulfide to sulfone transformation with reduced amounts of sulfoxide byproducts. Thus, whether or not the substrates treated in Oguma and He are simpler than pyroxasulfone does not make them nonanalogous art as argued by applicants as the courts have previously held that a prior art reference must either be in the field of the inventor’s endeavor or, if not, then be reasonably pertinent to the particular problem with which the inventor was concerned, in order to be relied upon as a basis for rejection of the claimed invention. See In re Oetiker, 977 F.2d 1443, 24 USPQ2d 1443 (Fed. Cir. 1992). In this case, as mentioned above Liang, Oguma and He are in the field of endeavor, specifically organic chemistry methodology development, and are reasonably pertinent to applicant’s problem in that they are directed to selective oxidation of sulfides to sulfones with minimal formation of undesired sulfoxide byproducts. Thus, the combination of Frasetto with the secondary references Liang, Oguma, He, etc. is appropriate and still renders the method instantly claimed obvious for the reasons discussed above and herein.
Applicants then argue declaration 3, and the examiner notes that all declarations will be further addressed separately below. They argue that using computational chemistry they have determined that the compounds reacted in Oguma and He are much simpler and are more difficult to oxidize based on the HOMO/LUMO calculations. However, these are not the only references being used in the claimed rejection, because these references in light of the teachings of Liang which are directed to the claimed pyroxasulfone and teach that the reactions can occur in methanol and acetonitrile do make it obvious to switch the solvents, etc. of Frasetto for the claimed solvents and/or the tungstate for molybdenum catalyst as claimed as are discussed above. Thus, at this time the examiner still believes that the claimed method is still rendered obvious when taken in view of the combined references.
Further, applicants argue that Frasetto’s compounds are structurally distinct and more complex than the structurally different compounds in the secondary references Oguma and He. The examiner respectfully points out that applicants exact compounds, pyraoxasulfone and the intermediates leading thereto as taught by Frasetto do not need to be taught by each and every reference in order to be appropriate and proper prior art for rendering the instantly claimed method obvious. The secondary references are reasonably directed to the same problem that applicants are solving with their solvents, transition metal catalyst and hydrogen peroxide in their claimed step iii, specifically the selective oxidation of a compound containing a sulfide to the desired sulfone compound with minimal/reduced amounts of the undesired sulfoxide containing compound as a byproduct of the oxidation reaction. Oguma and He both teach that selective oxidations of sulfides to sulfones with minimal formation of undesired sulfoxide containing compounds are known in the art, and it is normal for scientists trying to improve synthetic methods to look to other papers/publications which accomplish the same selective transformations and to try their effective conditions and/or use these conditions as a starting point for adapting/developing similar/related reaction conditions (solvents, temperatures, etc.) to effectively perform these selective reactions, in this case selective oxidation of sulfide to sulfone on other more complex molecules. Applicants further argue that the Frasetto teaches difficulty with their compounds that are not recognized by the secondary references. The examiner respectfully does not believe these difficulties with their compounds in Frasetto teach away from developing the claimed conditions by looking to Liang, Oguma and He because nothing in Oguma or He or the instant claims specifically require the compounds to be stable after distillation/purification for a specific amount of time, nor does the instant claims require a specific yield of pyroxasulfone. The claims merely require that the undesired sulfoxide compound is present in less than 5% by weight of the product which is taught by Oguma and He to be known to be accomplished by using their reaction conditions for sulfide to sulfone transformations and these conditions overlap in scope with those instantly claimed in that they teach the same solvents, and the same transition metal catalysts and overlapping temperature ranges were known in the art to be used to accomplish these types of selective sulfur oxidations. Secondly, whether or not the starting materials are difficult to form does not mean that they cannot be formed. There is also no specific requirement that the starting materials be easy to form in the claimed reactions. Applicants further argue that Frasetto teaches that some compounds preferentially form in a different solvent from the subsequent reaction product and as such a solvent exchange or performing the different reactions in different vessels is required. Again nothing in the instant claims excludes solvent exchange or other steps or different reaction vessels from the instant claims. The examiner understands that applicants objective is provide an inexpensive, etc. synthetic method. However, none of that is required by the instant claims and further whether or not applicants have found other advantages to the claimed method does not mean that the method is not still obvious when taken in view of the combination of the prior art as discussed above. Thus, for the reasons discussed above and herein the examiner respectfully disagrees with applicants assertion that because Oguma and He are directed to selectively oxidizing structurally different sulfides and sulfones that these references are not relevant to the instant claims or the instant rejections and these teachings cannot be used to modify Frasetto. Applicants then argue impermissible hindsight. The examiner respectfully disagrees because, it must be recognized that any judgment on obviousness is in a sense necessarily a reconstruction based upon hindsight reasoning. But so long as it takes into account only knowledge which was within the level of ordinary skill at the time the claimed invention was made, and does not include knowledge gleaned only from the applicant's disclosure, such a reconstruction is proper. See In re McLaughlin, 443 F.2d 1392, 170 USPQ 209 (CCPA 1971). In the instant case the teachings being combined are all found in the prior art and in the case of Oguma and He teach selective oxidization of the same sulfide functional groups to the same sulfone functional groups selectively while limiting the amounts of sulfoxide byproducts that are formed. Thus, the combination of the prior art is proper and does still render the instant claims obvious for the reasons previously discussed. Further, the examiner has now added Liang to the rejection which further ties in forming pyroxasulfone with the claimed solvents of Oguma and He, etc.
Applicants then further argue that there has to be something more, some underpinning articulated reason that one lead one of ordinary skill in the art to modify the sulfur oxidation to sulfone step of Frasetto to be the claimed step iii. The examiner respectfully points out that she has provided rational underpinning as to why it would be obvious to modify Frasetto as has been discussed above and is therefore included again herein. Applicants then argue impermissible hindsight. The examiner respectfully disagrees because, it must be recognized that any judgment on obviousness is in a sense necessarily a reconstruction based upon hindsight reasoning. But so long as it takes into account only knowledge which was within the level of ordinary skill at the time the claimed invention was made, and does not include knowledge gleaned only from the applicant's disclosure, such a reconstruction is proper. See In re McLaughlin, 443 F.2d 1392, 170 USPQ 209 (CCPA 1971). In the instant case the teachings being combined are all found in the prior art and in the case of Liang, Oguma and He each teach selective oxidization of the same sulfide functional groups to the same sulfone functional groups selectively while limiting the amounts of sulfoxide byproducts that are formed. Thus, the combination of the prior art is proper and does still render the instant claims obvious for the reasons previously discussed.
Applicants then argue that ‘689 merely provides a general disclosure and is non-analogous to Frasetto because ‘689 does not use a metal catalyst. The examiner respectfully points out that ‘689 is not being used to teach step iii reaction/reaction solvents anymore and as such this argument is moot.
In light of the forgoing discussion, the Examiner concludes that the subject matter defined by the above claims would have been obvious to one of ordinary skill in the art within the meaning of 35 USC 103(a).
From the teachings of the references, it is apparent that one of ordinary skill in the art would have had a reasonable expectation of success in producing the claimed invention. Therefore, the invention as a whole would have been prima facie obvious to one of ordinary skill in the art at the time the invention was made, as evidenced by the references, especially in the absence of evidence to the contrary.
Declarations Under 1.132
Tetsuya Hirade provided a declaration under 1.132, filed 07/18/25. The Declaration meets the formal requirements. In the most relevant part, the Declaration presents computational data which compares the reactivity of the compound exemplified in He and Oguma vs the instantly claimed method and calculates the energy level, i.e. HOMO (highest occupied molecular orbital) of the starting material for the oxidation reaction and the LUMO (lowest unoccupied molecular orbital) of the oxidizing agent and using semi-empirical molecular orbital method PM7 to calculate the HOMO-LUMO gap of the materials wherein the larger the HOMO-LUMO gap the lower the reactivity. Their calculations show that the substrates used in He and Oguma are more reactive than the claimed (4) compound.
A Declaration is due full consideration and weight for all that it discloses. Declarations are reviewed for the following considerations: 1) whether the Declaration presents a nexus such as a side-by-side or single-variable comparison (In re Huang, 40 USPQ2d 1685, 1689 (Fed. Cir.
1996)), 2) whether the Declaration presents a comparison to the closest art, 3) whether the
Declaration is commensurate in scope with the scope of the claims (In re Kulling, 14 USPQ2d
1056, 1058 (Fed. Cir. 1990)), 4) whether the Declaration shows a difference in kind rather than
merely a difference in degree (In re Waymouth, 182 USPQ 290, 293 (C.C.P.A. 1974)), and 5)
whether the prima facie case is sufficiently strong that allegedly superior results are insufficient
to overcome the case for obviousness (Pfizer Inc. v. Apotex, Inc., 82 USPQ2d 1321, 1339 (Fed.
Cir. 2007)). The relevant criterion here is No. 1, whether the Declaration presents a nexus such as a side-by-side or single-variable comparison (In re Huang, 40 USPQ2d 1685, 1689 (Fed. Cir.
1996)). The examiner has carefully reviewed the Declaration, including the data presented in the Declaration.
In the most relevant part of the included declaration Tetsuya Hirade demonstrates that the claimed (4) compound which is being converted to (5) is less reactive than the substrates used in the oxidation reactions of He and Oguma. However, the examiner notes that this does not mean these reaction conditions would not work in instant reaction especially since there is no required specific yield of (5) from the claimed reaction, as long as it provide less than 5% of the sulfoxide byproduct (6). Further, the rejection now does not solely using He and Oguma as secondary references as Liang has also been added which demonstrates that the claimed solvents were able to support the formation of pyroxasulfone from (4) using hydrogen peroxide as the oxidant. Tetsuya Hirade asserts that because the reactitivity of the claimed substrate is different you cannot foresee the reaction would work effectively in the claimed substrate. However, an absolute guarantee of success is not the legal standard for an obviousness rejection. The standard for an obviousness rejection is a reasonable expectation of success. In the instant case, the claimed solvents and temperatures were known in the art to be useful for performing selective oxidation of sulfur atoms in compounds to sulfones with limited/minimal formation of the sulfoxide byproduct. Thus, it would be obvious to try these conditions in order to develop more effective conditions for oxidizing applicant’s (4) to form pyroxasulfone (5) with as little of the undesired byproduct (6) present. This is something that one of ordinary skill in the art routinely does is to start with reactions conditions which have been useful for the same transformation, e.g. sulfur to sulfone and use those as a starting point for optimization and developing the most effective reaction conditions. Thus, the examiner is not persuaded by this evidence at this time, that applicants conditions are not an obvious optimization of the conditions disclosed in the prior art for performing the same selective oxidation of sulfur to sulfone especially since for instance the new reference that has been added, Liang teaches that acetonitrile and methanol were solvents that allowed for the (4) to (5) oxidation reaction with hydrogen peroxide to occur.
Thus for the above reasons, the examiner maintains that it would have been obvious to one of ordinary skill in the art at the time of the instant filing to have developed the claimed reaction conditions when looking to the prior art references as combined at this time.
Tetsuya Hirade also provided a second declaration under 1.132, filed 07/18/25. The Declaration meets the formal requirements. In the most relevant part, the Declaration presents results from a later filed paper which reacted essentially a dimer of applicant’s (4) and formed what is nearly/basically a dimer of pyroxasulfone (5) under conditions reported by the later Recsei paper which also used hydrogen peroxide, sodium tungstate, and acetonitrile or methanol. Tetsuya Hirade states that their results are unexpected because an analog of pyroxasulfone done by Recsei only demonstrated 66% yield vs applicant’s achieved 96% yield of pyroxasulfone using these reaction conditions with less than 5% of the byproduct (6) being formed.
A Declaration is due full consideration and weight for all that it discloses. Declarations are reviewed for the following considerations: 1) whether the Declaration presents a nexus such as a side-by-side or single-variable comparison (In re Huang, 40 USPQ2d 1685, 1689 (Fed. Cir.
1996)), 2) whether the Declaration presents a comparison to the closest art, 3) whether the
Declaration is commensurate in scope with the scope of the claims (In re Kulling, 14 USPQ2d
1056, 1058 (Fed. Cir. 1990)), 4) whether the Declaration shows a difference in kind rather than
merely a difference in degree (In re Waymouth, 182 USPQ 290, 293 (C.C.P.A. 1974)), and 5)
whether the prima facie case is sufficiently strong that allegedly superior results are insufficient
to overcome the case for obviousness (Pfizer Inc. v. Apotex, Inc., 82 USPQ2d 1321, 1339 (Fed.
Cir. 2007)). The relevant criterion here is 3) whether the Declaration is commensurate in scope with the scope of the claims (In re Kulling, 14 USPQ2d 1056, 1058 (Fed. Cir. 1990). The examiner has carefully reviewed the Declaration, including the data presented in the Declaration.
In the most relevant part of the included declaration Tetsuya Hirade states that their results are unexpected because an analog of pyroxasulfone done by Recsei only demonstrated 66% yield vs applicant’s achieved 96% yield of pyroxasulfone using these reaction conditions with less than 5% of the byproduct (6) being formed.
The examiner respectfully points out that firstly these reaction conditions where these unexpected results were achieved which are conditions which fall within applicants broad scope of reaction conditions are not commensurate in scope with applicant’s claims as they are currently written. Specifically, Tetsuya Hirade asserts that applicant’s results are unexpected under these conditions because they got a higher yield than a pyroxasulfone analog tested by Recsei. Firstly, nothing in the instant claims requires any specific yield of applicant’s (5) pyroxasulfone. Specifically if the method achieves 1% of pyroxasulfone as long as (6) is formed in less than 5% it reads on the claimed method. Further, the claimed conditions do not require the specific temperature, or amounts, or timings, e.g. 1.5 days, etc. with which applicant’s argued unexpected results were achieved. Thus, the argued unexpected results are much narrower in scope than the instant claims which allow for any amount of molybdenum or tungsten catalyst, any amount of any strength hydrogen peroxide and any amount/ratio of the organic solvent and water and any amounts of the reactant (4) at any temperature and for any amount of time, whereas the argued unexpected results were obtained under much narrower conditions, with specific timings, temperature, catalyst, amounts of each reaction component,, strength of hydrogen peroxide solution used, etc. Thus, while the argued results might be unexpected, the results are not commensurate in scope with applicants claims at this time and as such are not enough to overcome the obviousness rejection of record for the reasons discussed above and herein.
Thus for the above reasons, the examiner maintains that it would have been obvious to one of ordinary skill in the art at the time of the instant filing to have developed the claimed reaction conditions when looking to the prior art references as combined at this time.
Tetsuya Hirade also provided a third declaration under 1.132, filed 07/18/25. The Declaration meets the formal requirements. In the most relevant part, the Declaration presents results from tests of comparative examples under the claimed reaction conditions and demonstrate that these comparative examples provide much lower yields of their oxidized products than the instantly claimed substrate (4) which is oxidized to pyroxasulfone in high yields.
A Declaration is due full consideration and weight for all that it discloses. Declarations are reviewed for the following considerations: 1) whether the Declaration presents a nexus such as a side-by-side or single-variable comparison (In re Huang, 40 USPQ2d 1685, 1689 (Fed. Cir.
1996)), 2) whether the Declaration presents a comparison to the closest art, 3) whether the
Declaration is commensurate in scope with the scope of the claims (In re Kulling, 14 USPQ2d
1056, 1058 (Fed. Cir. 1990)), 4) whether the Declaration shows a difference in kind rather than
merely a difference in degree (In re Waymouth, 182 USPQ 290, 293 (C.C.P.A. 1974)), and 5)
whether the prima facie case is sufficiently strong that allegedly superior results are insufficient
to overcome the case for obviousness (Pfizer Inc. v. Apotex, Inc., 82 USPQ2d 1321, 1339 (Fed.
Cir. 2007)). The relevant criterion here is 3) whether the Declaration is commensurate in scope with the scope of the claims (In re Kulling, 14 USPQ2d 1056, 1058 (Fed. Cir. 1990). The examiner has carefully reviewed the Declaration, including the data presented in the Declaration.
In the most relevant part of the included declaration Tetsuya Hirade demonstrates that their results are much higher than the comparative analogs of pyroxasulfone when the analogs of applicant’s (4) are subjected to the same oxidation conditions as (4) in order to achieve sulfone products structurally similar to the claimed pyroxasulfone (5).
The examiner respectfully points out that firstly these reaction conditions where these much lower yields vs pyroxasulfone were achieved which are conditions which fall within applicants broad scope of reaction conditions but these conditions are not commensurate in scope with applicant’s claims as they are currently written. Specifically, Tetsuya Hirade asserts that applicant’s results are unexpected under these conditions because they got a much higher yield of the claimed pyroxasulfone than the pyroxasulfone analogs tested by Recsei. Firstly, nothing in the instant claims requires any specific yield of applicant’s (5) pyroxasulfone. Specifically if the method achieves 1% of pyroxasulfone as long as (6) is formed in less than 5% it reads on the claimed method. Further, the claimed conditions are much broader in scope than those under which applicant’s argued unexpected results were achieved. Thus, the argued unexpected results are much narrower in scope than the instant claims which allow for any amount of molybdenum or tungsten catalyst, any amount of any strength hydrogen peroxide and any amount/ratio of the organic solvent and water and any amounts of the reactant (4) at any temperature and for any amount of time, whereas the argued unexpected results were obtained under much narrower conditions, with specific timings, temperature, catalyst, amounts of each reaction component,, strength of hydrogen peroxide solution used, etc. Thus, while the argued tested results of the declaration might be unexpected, the results are not commensurate in scope with applicants claims at this time and as such are not enough to overcome the obviousness rejection of record for the reasons discussed above and herein.
Thus for the above reasons, the examiner maintains that it would have been obvious to one of ordinary skill in the art at the time of the instant filing to have developed the claimed reaction conditions when looking to the prior art references as combined at this time.
Conclusion
No claims are allowed.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Erin E Hirt whose telephone number is (571)270-1077. The examiner can normally be reached 10:30-7:30 ET M-F.
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/ERIN E HIRT/Primary Examiner, Art Unit 1616