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 .
Claim Status
Claims 1-9 were filed on 8/4/2023 and are currently pending.
Priority
The application was filed on 8/4/2023 and claims the benefit of priority to:
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See filing receipt dated 8/17/2023. Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
Claim Objections
Claims 5-9 are objected to because of the following informalities:
in line 3 of claims 5-8 and in line 15 of claim 9, the word “carbonyl” is misspelled as “carbony”. The misspellings should be corrected.
The definition of variable R5 in claim 8 should be reversed from “P1-[-NH-CHR6-C(=O)-]l-“ to “[-C(=O)-CHR6-NH-]-P1” because the nitrogen atom attached to R5 (N-R5) will be attached to the carbonyl carbon (C=O) of the chain and not through P1 or the nitrogen group (NHP1). The Applicant is claiming a peptide at R5, but the attachment orientation as recited in the claim does not match what is actually being produced in the claim.
In line 17 of claim 9, the limitation “amino acid” should be deleted and replaced by “amide”. Compound (IX) is an amide and not an amino acid.
Appropriate correction is required.
Additionally, in claim 8, the Examiner also suggests that the Applicant may want to consider the use of a different font or to substitute a different variable for “l” (lower case l) in the definition of variable R6 because variable “l” in the definition of R6 looks almost identical to number “1” in the font used.
Claim Rejections - 35 USC § 102
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
(a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention.
Claim(s) 1 and 3 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Takahashi (JPS63319205A, published on 12/27/1988, of record in the IDS filed on 9/26/2025). A machine generated translation of Takahashi is provided with the instant OA.
Takahashi teaches an example wherein tetrachloroethylene (TOE in the translation; TCE in the patent) is vaporized in the presence of oxygen (from air) and irradiated with UV for 5 minutes (300 seconds-claim 3) to produce phosgene. See lines 78-122 of the translation and Figure 1. Tetrachloroethylene is a C2 halogenated hydrocarbon substituted by four chlorine atoms and phosgene is a carbonyl halide of formula (Cl-C(O)-Cl). Takahashi teaches that the oxygen (1) and TCE (2) are flowed through quartz tube (3) and the gaseous mixture is irradiated with the UV light source (4) at a wavelength between 200-290 nm to produce phosgene. See Figure 1, abstract, and lines 114-122. This wavelength meets the limitations of the claimed “high energy light” (see p. 16, [0036] of the specification as filed). Therefore the example of Takahashi anticipates claim 1. Also see MPEP 2131.
Claim Rejections - 35 USC § 103
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
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) 1-4 is/are rejected under 35 U.S.C. 103 as being unpatentable over Takahashi (JPS63319205A, published on 12/27/1988, of record in the IDS filed on 9/26/2025) as evidenced by CID 31373 (downloaded from https://pubchem.ncbi.nlm.nih.gov/compound/Tetrachloroethylene#section=Boiling-Point&fullscreen=true on 3/3/2026).
The Applicant claims a method for producing a carbonyl halide, comprising the steps of:
Preparing a mixed gas comprising oxygen and a C2-4 halogenated hydrocarbon having one or more halogeno groups selected from the group consisting of chloro, bromo, and iodo, and
Flowing the mixed gas and irradiating a high energy light to the flowed mixed gas.
Takahashi teaches an anticipatory example wherein tetrachloroethylene (TOE in the translation; TCE in the patent) is vaporized in the presence of oxygen (from air) and irradiated with UV for 5 minutes (300 seconds-claim 3) to produce phosgene. See lines 78-122 of the translation and Figure 1. Tetrachloroethylene is a C2 halogenated hydrocarbon substituted by four chlorine atoms and phosgene is a carbonyl halide of formula (Cl-C(O)-Cl). Takahashi teaches that the oxygen (1) and TCE (2) are flowed through quartz tube (3) and the gaseous mixture is irradiated with the UV light source (4) at a wavelength between 200-290 nm to produce phosgene. See Figure 1, abstract, and lines 114-122. This wavelength meets the limitations of the claimed “high energy light” (see p. 16, [0036] of the specification as filed).
Takahashi does not explicitly teach the temperature of the example or the dimensions of the apparatus used.
Regarding the reaction temperature (claim 4), Takahashi teaches that when the TCE is subjected to the reaction as a liquid, the irradiation can take place in the range of 0 to 100°C. See lines 36-46. Takahashi further discusses the gas phase reaction in lines 47-53, but does not provide a specific temperature range. However, as evidenced by CID 31373, the temperature of the reaction must be at least 120°C or greater, the boiling point of TCE. This reaction temperature range encompasses that claimed. See MPEP 2144.05.
Regarding the reaction apparatus (claim 2), Takahashi appears to carry out bench scale reactions as evidenced by the Figures and experimental procedures. Takahashi only teaches that the light source (4 in Fig. 1 and 19 in Fig. 2) surrounds the reaction vessel, and the Figures depict the light source as being in close proximity to the reaction vessel. See lines 78-122 of the translation. Takahashi also discusses that the absorption of the wavelength, the concentration of TCE, and the time of irradiation (claim 3) are results-effective variables. Takahashi also teaches that the reaction is monitored such that the reaction can be adjusted in real time based upon said readings. See lines 31-66.
It would have been prima facie obvious to arrive at the instantly claimed process based on the teachings of Takahashi with a reasonable expectation of success before the effective filing date of the claimed invention. A person of ordinary skill would have been motivated to carry out the reaction in the temperature range of claim 4 because the boiling point of TCE is the lower end of the claimed range. Therefore, if the reaction is being carried out in the gaseous phase, then the irradiation temperature must be at least as high as 120°C, which overlaps with the claimed range. Also see MPEP 2144.05.
A person of ordinary skill would have been motivated to modify the process such that the shortest distance from the light source to the flowed mixed gas is 1m or less because i) if the reaction is carried out at bench scale, it is unlikely that the light source is 1m or greater away from the reaction, which is supported by the Figures, and ii) even if it is not, Takahashi teaches that the time of irradiation and absorption of the wavelength are both results-effective variables which can affect the strength of the irradiation step. If the reaction were too harsh, the skilled artisan could predictably decrease the irradiation time and/or change the wavelength or move the light source further away from the reaction and/or decrease the concentration of the TCE. Likewise, if the reaction were too mild, the skilled artisan could predictably do the reverse. Additionally, Takahashi teaches that it is routine to monitor the reaction and make adjustments to reaction parameters based on the data gathered. Therefore, the skilled artisan could use routine optimization to predictably arrive at the claimed process with a reasonable expectation of success based on the teachings of Takahashi. Also see MPEP 2144.05.
Claim(s) 5 is/are rejected under 35 U.S.C. 103 as being unpatentable over Takahashi (JPS63319205A, published on 12/27/1988, of record in the IDS filed on 9/26/2025) as evidenced by CID 31373 (downloaded from https://pubchem.ncbi.nlm.nih.gov/compound/Tetrachloroethylene#section=Boiling-Point&fullscreen=true on 3/3/2026), as applied to claims 1-4 above, and further in view of Tsuda (JP2013181028A, published on 9/12/2013, of record in the IDS filed on 8/4/2023). A machine generated translation of Tsuda is provided with the instant OA.
The Applicant claims producing a halogenated carbonyl using the process of claim 1 and further reacting the halogenated carbonyl with an alcohol to produce carbonate derivatives.
In addition to the discussion in the previous rejection, Takahashi further teaches that the phosgene produced in the reaction is “one of the most important raw materials in synthetic chemistry”. A number of different uses for phosgene are discussed, though not specifically how the phosgene is transformed for said uses. See lines 9-13 of the translation.
Tsuda teaches an analogous process to that of Takahashi, which is a process for use of a halogen and/or carbonyl halide derived from a mixture obtained by irradiating a halogenated hydrocarbon in the presence of oxygen as a chemical reaction raw material in a chemical reaction. See abstract and claims. In a first step, Tsuda teaches that the halide and/or carbonyl halide, including carbonyl chloride (phosgene), bromide, and iodide [0011], is obtained by irradiating a halogenated hydrocarbon, including the haloethene of Takahashi [0012], with oxygen at a wavelength of 400 nm or less. See [0013]. While Takahashi contemplates the use of both gas phase and gas/liquid phase reactions, Tsuda only contemplates the use of a mixed gas/liquid reaction. See examples, which teach volume amounts of hydrocarbons in mL and a reaction temperature at 20°C. See [0032-0042]. The formation of the halogen and/or carbonyl halide is described in detail in [0010-0024].
Tsuda further teaches that the second step of the process comprises reacting the halogen and/or carbonyl halide, including phosgene, with a primary amine or alcohol, preferably in the same system. See [0027-0030] and examples. When a primary amine is used, a urea derivative is obtained [0028] and when an alcohol is used, a carbonate derivative is obtained [0029]. Tsuda teaches that the amount of amine and alcohol are not particularly limited as long as the effects of the present invention are not impaired. In examples 3 and 4 in [0034-0035], Tsuda teaches the production of carbonates by reacting the intermediate phosgene with an excess of the monoalcohol, preferably a molar excess of at least 1:2 (phosgene:monoalcohol) to effect double substitution of both halogen atoms. Tsuda further teaches that “The chemical reaction of the present invention is not particularly limited as long as it involves a chemical reaction requiring a halogen and / or a carbonyl halide as a reactant etc. For example, a halide formation reaction, a urea derivative formation reaction, a carbonate derivative formation reaction, the carbodiimide derivative formation reaction, the isocyanate derivative formation reaction and the like are preferably mentioned. Further, the reaction conditions in the chemical reaction of the present invention can be appropriately set according to the desired reaction”. See [0014].
It would have been prima facie obvious to combine the teachings of Takahashi and Tsuda to arrive at the claimed process with a reasonable expectation of success before the effective filing date of the claimed invention. A person of ordinary skill would have been motivated to prepare a carbonate compound from phosgene because Tsuda teaches that phosgene that has been generated by irradiation in an analogous process to that of Takahashi can be predictably reaction with an excess of an alcohol to produce a carbonate compound with a reasonable expectation of success. Therefore, using a known synthetic intermediate in a known and predictable process for its use is not inventive.
Claim(s) 6 is/are rejected under 35 U.S.C. 103 as being unpatentable over Takahashi (JPS63319205A, published on 12/27/1988, of record in the IDS filed on 9/26/2025) as evidenced by CID 31373 (downloaded from https://pubchem.ncbi.nlm.nih.gov/compound/Tetrachloroethylene#section=Boiling-Point&fullscreen=true on 3/3/2026) and Tsuda (JP2013181028A, published on 9/12/2013, of record in the IDS filed on 8/4/2023) as applied to claims 1-5 above, and further in view of Akihiko (WO 2015/156245, published on 10/15/2015, of record in the IDS filed on 8/4/2023). A machine generated translation of Akihiko is provided with the instant OA.
The Applicant claims producing a halogenated carbonyl using the process of claim 1 and further reacting the halogenated carbonyl with an alcohol to produce a halogenated formic acid ester.
The combination of Takahashi and Tsuda teach the method of instant claim 1 to produce carbonyl halides and reaction of the halides with a molar excess of an alcohol to produce carbonates.
Akihiko teaches an analogous process to that of Takahashi and Tsuda wherein the carbonyl halide formation reaction takes place in the presence of a stoichiometric or sub-stoichiometric amount of an alcohol (≤1 mole alcohol: 1 mole carbonyl halide) to produce a halogenated formic acid ester of formula (I). See abstract and claims. Also see examples in lines 412-558 of the translation. Akihiko also teaches that the halogenated carboxylic acid ester can be used as a raw material for producing urethane, asymmetric carbonic acid esters, carbamic acid esters, and the like. See lines 394-395.
It would have been prima facie obvious to combine the teachings of Takahashi, Tsuda, and Akihiko to arrive at the instantly claimed process with a reasonable expectation of success before the effective filing date of the claimed invention. A person of ordinary skill would have been motivated to modify the combined process of Takahashi and Tsuda to produce halogenated formic acid esters because Akihiko teaches that if a stoichiometric or sub-stoichiometric amount of alcohol is added in the second step, that halogenated formic acid esters would be the expected product and that halogenated carboxylic acid esters are valuable synthetic raw materials, thus providing further motivation to obtain them from the combined process. Therefore, Akihiko teaches that the combined process of Takahashi and Tsuda can be predictably modified to obtain another valuable synthetic raw material with a reasonable expectation of success. Also see MPEP 2143(I)(A).
Claim(s) 7 is/are rejected under 35 U.S.C. 103 as being unpatentable over Takahashi (JPS63319205A, published on 12/27/1988, of record in the IDS filed on 9/26/2025) as evidenced by CID 31373 (downloaded from https://pubchem.ncbi.nlm.nih.gov/compound/Tetrachloroethylene#section=Boiling-Point&fullscreen=true on 3/3/2026) and Tsuda (JP2013181028A, published on 9/12/2013, of record in the IDS filed on 8/4/2023) as applied to claims 1-5 above, and further in view of Slocombe (“Phosgene Derivatives. The Preparation of Isocyanates, Carbamyl Chlorides and Cyanuric Acid” J. Am. Chem. Soc., 1950, p. 1888).
The Applicant claims producing a halogenated carbonyl using the process of claim 1 and further reacting the halogenated carbonyl with a primary amine to produce an isocyanate.
The combination of Takahashi and Tsuda teach the method of instant claim 1 to produce carbonyl halides and reaction of the halides with a molar excess of an alcohol to produce carbonate derivatives or a molar excess of amine to produce urea derivatives. Takahashi also mentions that the carbonyl halide products can also be used to produce carbodiimide derivatives and isocyanate derivatives, and that the use of the carbonyl halides is not particularly limited as long as it requires the carbonyl halide. See [0014] of the translation. Takahashi does not teach specific conditions for the formation of the isocyanate and other products from the carbonyl halides.
Slocombe teaches the reaction between phosgene (COCl2) and a stoichiometric or sub-stoichiometric amount (≤1 mole) of a primary (RNH2) to form a carbamoyl chloride (RNHCOCl), which is then decomposed to an isocyanate (RNCO):
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. See col. 1 on p. 1888 and experimental section.
It would have been prima facie obvious to combine the teachings of Takahashi, Tsuda, and Slocombe to arrive at the instantly claimed process with a reasonable expectation of success before the effective filing date of the claimed invention. A person of ordinary skill would have been motivated to modify the combined process of Takahashi and Tsuda to produce isocyanates because Tsuda teaches that the carbonyl halides from the process can be used to produce isocyanates and Slocombe teaches the specific conditions used to convert phosgene (carbonyl halide) to an isocyanate. Therefore, Slocombe teaches that the combined process of Takahashi and Tsuda can be predictably modified to obtain another valuable synthetic raw material with a reasonable expectation of success. Also see MPEP 2143(I)(A).
Claim(s) 8 is/are rejected under 35 U.S.C. 103 as being unpatentable over Takahashi (JPS63319205A, published on 12/27/1988, of record in the IDS filed on 9/26/2025) as evidenced by CID 31373 (downloaded from https://pubchem.ncbi.nlm.nih.gov/compound/Tetrachloroethylene#section=Boiling-Point&fullscreen=true on 3/3/2026) and Tsuda (JP2013181028A, published on 9/12/2013, of record in the IDS filed on 8/4/2023) as applied to claims 1-5 above, and further in view of Gerlach (“Scale-Up Studies for the Asymmetric Julia-Colonna Epoxidation Reaction” Adv. Synth. Catal. 2004, p. 1247).
The Applicant claims producing a halogenated carbonyl using the process of claim 1 and further reacting the halogenated carbonyl with an amino acid of formula (VII) to produce the amino acid-N-carboxylic anhydride of formula (VIII).
The combination of Takahashi and Tsuda teach the method of instant claim 1 to produce carbonyl halides and reaction of the halides with a molar excess of an alcohol to produce carbonate derivatives or a molar excess of amine to produce urea derivatives. Takahashi also mentions that the carbonyl halide products can also be used to produce carbodiimide derivatives and isocyanate derivatives, and that the use of the carbonyl halides is not particularly limited as long as it requires the carbonyl halide. See [0014] of the translation.
Gerlach teaches the reaction of phosgene (COCl2) with L-leucine (5) to produce L-leucine N-carboxy anhydride (6, L-leu-NCA):
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. See scheme 2 on p. 1247 and first step of the experimental procedure for (7) on p. 1249. Leucine (5) is a compound of instant formula (VII) wherein R4 is iso-butyl an unreactive, unprotected amino acid side chain group, and R5 is H. L-leu-NCA (6) is a compound of instant formula (VIII) wherein R4 and R5 are the same as above. Gerlach teaches that compound (6) is a key intermediate for producing Julia-Colonna epoxidation catalysts of poly-L-leucine (7, pll). See scheme 3 and Table 1 on p. 1248 and experimental section.
It would have been prima facie obvious to combine the teachings of Takahashi, Tsuda, and Gerlach to arrive at the instantly claimed process with a reasonable expectation of success before the effective filing date of the claimed invention. A person of ordinary skill would have been motivated to modify the combined process of Takahashi and Tsuda to produce anhydrides of instant formula (VIII) because Gerlach teaches that phosgene, a carbonyl halide, can be reacted with an amino acid of instant formula (VII) to produce said compound of formula (VIII). Gerlach further teaches the importance of the compound of instant formula (VIII) as a key intermediate in the synthesis of a pll catalyst., thus providing further motivation to obtain said compound. Therefore, Gerlach teaches that the combined process of Takahashi and Tsuda can be predictably modified to obtain another valuable synthetic raw material with a reasonable expectation of success. Also see MPEP 2143(I)(A).
Claim(s) 9 is/are rejected under 35 U.S.C. 103 as being unpatentable over Takahashi (JPS63319205A, published on 12/27/1988, of record in the IDS filed on 9/26/2025) as evidenced by CID 31373 (downloaded from https://pubchem.ncbi.nlm.nih.gov/compound/Tetrachloroethylene#section=Boiling-Point&fullscreen=true on 3/3/2026) and Tsuda (JP2013181028A, published on 9/12/2013, of record in the IDS filed on 8/4/2023) as applied to claims 1-5 above, and further in view of Haveaux (“α-CHLORO ENAMINES, REACTIVE INTERMEDIATES FOR SYNTHESIS: 1-CHLORO-N,N,2-TRIMETHYLPROPENYLAMINE” Organic Syntheses, Coll. Vol. 6, p.282 (1988); Vol. 59, p.26 (1979)).
The Applicant claims producing a halogenated carbonyl using the process of claim 1 and further reacting the halogenated carbonyl with an amide of instant formula (IX) to produce a Vilsmeier reagent of instant formula (X).
The combination of Takahashi and Tsuda teach the method of instant claim 1 to produce carbonyl halides and reaction of the halides with a molar excess of an alcohol to produce carbonate derivatives or a molar excess of amine to produce urea derivatives. Takahashi also mentions that the carbonyl halide products can also be used to produce carbodiimide derivatives and isocyanate derivatives, and that the use of the carbonyl halides is not particularly limited as long as it requires the carbonyl halide. See [0014] of the translation.
Haveaux teaches the reaction of phosgene (Cl2CO) with N,N-dimethylisobutyramide to produce 1-chloro-N,N-2,trimethylpropylideniminium chloride (top reaction), which is then converted to its enamine form with triethylamine (bottom reaction):
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. See scheme on p. 2 and experimental procedure A for top reaction and experimental procedure B for bottom reaction on p. 2-3. N,N-Dimethylisobutyramide is an amide of instant formula (IX), wherein R7 is isopropyl (C3 alkyl) and R8 and R9 are methyl (C1 alkyl). The iminium product of the top reaction corresponds to a compound of instant formula (X) wherein R7, R8, and R9 are as above; X is Cl and Y- is Cl-. In section 3 on p. 4-6, Haveaux teaches that both the iminium (keteniminium) product and the enamine product are valuable synthetic intermediates.
It would have been prima facie obvious to combine the teachings of Takahashi, Tsuda, and Haveaux to arrive at the instantly claimed process with a reasonable expectation of success before the effective filing date of the claimed invention. A person of ordinary skill would have been motivated to modify the combined process of Takahashi and Tsuda to produce compounds of instant formula (X) because Haveaux teaches that phosgene, a carbonyl halide, can be reacted with an amide of instant formula (IX) to produce said compound of formula (X). Haveaux further teaches the importance of the compound of instant formula (X) as a key intermediate a variety of synthetic pathways, thus providing further motivation to obtain said compound. Therefore, Haveaux teaches that the combined process of Takahashi and Tsuda can be predictably modified to obtain another valuable synthetic raw material with a reasonable expectation of success. Also see MPEP 2143(I)(A).
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 1-9 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-11 of co-pending Application No. 18/350092 (‘092, reference application).
Although the claims at issue are not identical, they are not patentably distinct from each other because the claims of ‘092 recite an obvious variant to that claimed wherein a C1 halogenated hydrocarbon (halogenated methane) is subjected to identical conditions to those claimed to produce a carbonyl halide. Methane is a one-carbon homolog of the instantly claimed compounds, therefore, it would have been prima facie obvious to arrive at the instantly claimed process by subjecting homologs of methane to the process of ‘092 to arrive at that claimed. Also see MPEP 2144.09. Further regarding claim 4, the temperature range of claim 4 of ‘092 overlaps with that claimed. Also see MPEP 2144.05. Further regarding claims 5-9, see claims 5-11 of ‘092.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Claims 1-9 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-13 of co-pending Application No. 19/122538 (‘538, reference application).
Although the claims at issue are not identical, they are not patentably distinct from each other because the claims of ‘538 recite irradiating a mixture of C1 halogenated hydrocarbon (halogenated methane), oxygen, and ozone to produce a carbonyl halide. Methane is a one-carbon homolog of the instantly claimed compounds, therefore, it would have been prima facie obvious to arrive at the instantly claimed process by subjecting homologs of methane to the process of ‘538 to arrive at that claimed. Also see MPEP 2144.09. Further regarding claims 2-4, see claims 6-7 of ‘538, wherein the distance between the light and the mixed gas is obtainable through routine optimization. Also see MPEP 2144.05. Further regarding claims 5-9, see claims 8-13 of ‘538.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Claims 1-5 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-5 of U.S. Patent No. 12351568 (‘568).
Although the claims at issue are not identical, they are not patentably distinct from each other because the claims of ‘568 are directed to the instantly claimed process of claim 5, wherein the alcohol is present during the first reaction step to produce the carbonate. As evidenced by example 16 in ‘568, the reaction necessarily produces phosgene (carbonyl halide) as an intermediate to the carbonate. See MPEP 2112. Further regarding claims 2-4, these are all values which would be arrived at through routine optimization. Also see MPEP 2144.05.
Claims 1-5 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-7 of U.S. Patent No. 12234321 (‘321).
Although the claims at issue are not identical, they are not patentably distinct from each other because the claims of ‘321 are directed to the instantly claimed process of claim 5, wherein the alcohol is present during the first reaction step to produce a polycarbonate. As evidenced by col. 17, lines 18-21 of ‘321, the reaction necessarily produces phosgene (carbonyl halide) as an intermediate to the polycarbonate. See MPEP 2112. Further regarding claims 2-4, these are all values which would be arrived at through routine optimization. Also see MPEP 2144.05.
Claims 1-3 and 7 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-10 of U.S. Patent No. 12060312 (‘312).
Although the claims at issue are not identical, they are not patentably distinct from each other because the claims of ‘312 are directed to the instantly claimed process of claim 7, wherein halogenated methane is used in the first step. As evidenced by col. 3, line 39-colo. 4, line 3 of ‘312, the first step produces a carbonyl halide intermediate. Methane is a one-carbon homolog of the instantly claimed compounds, therefore, it would have been prima facie obvious to arrive at the instantly claimed process by subjecting homologs of methane to the process of ‘312 to arrive at that claimed. Also see MPEP 2144.09. Further regarding claims 2-3, these are all values which would be arrived at through routine optimization. Also see MPEP 2144.05.
Claims 1-5 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-9 of U.S. Patent No. 11130728 (‘728).
Although the claims at issue are not identical, they are not patentably distinct from each other because the claims of ‘728 are directed to the instantly claimed process of claim 5, wherein a nucleophilic functional group-containing compound and a base are present in the first step. As evidenced by col. 10, lines 45-58 of ‘728, the first step produces a carbonyl halide intermediate. Further regarding claims 2-4, these are all values which would be arrived at through routine optimization. Also see MPEP 2144.05.
Claims 1-5 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-12 of U.S. Patent No. 11167259 (‘259).
Although the claims at issue are not identical, they are not patentably distinct from each other because the claims of ‘259 are directed to the instantly claimed process of claim 5, wherein a nucleophilic functional group-containing compound comprising fluorine and a base are present in the first step. As evidenced by col. 11, lines 43-57 of ‘259, the first step produces a carbonyl halide intermediate. Further regarding claims 2-4, these are all values which would be arrived at through routine optimization. Also see MPEP 2144.05.
Claims 1-4 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-8 of U.S. Patent No. 12421121 (‘121).
Although the claims at issue are not identical, they are not patentably distinct from each other because the claims of ‘121 are directed to the instantly claimed process wherein the process includes ultrasound and can also be applied to C1 halogenated hydrocarbons. Further regarding claims 2-4, these are all values which would be arrived at through routine optimization. Also see MPEP 2144.05.
Claim 5 is rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-8 of U.S. Patent No. 12421121 (‘121), as applied to claims 1-4 above, and further in view of Tsuda (JP2013181028A, published on 9/12/2013, of record in the IDS filed on 8/4/2023).
The teachings of Tsuda were discussed in a prior 35 USC 103 rejection and are incorporated herein. It would have been prima facie obvious to combine the claims of ‘121 and the teachings of Tsuda to arrive at the instantly claimed process with a reasonable expectation of success before the effective filing date of the claimed invention. A person of ordinary skill would have been motivated to prepare carbonates from the carbonyl halides produced in the claims of ‘121 because Tsuda teaches this is a well-known and predictable process. Therefore, using a compound for its intended use is not inventive. Also see MPEP 2143(I)(A).
Claim 6 is rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-8 of U.S. Patent No. 12421121 (‘121), as applied to claims 1-4 above, and further in view of Akihiko (WO 2015/156245, published on 10/15/2015, of record in the IDS filed on 8/4/2023).
The teachings of Akihiko were discussed in a prior 35 USC 103 rejection and are incorporated herein. It would have been prima facie obvious to combine the claims of ‘121 and the teachings of Akihiko to arrive at the instantly claimed process with a reasonable expectation of success before the effective filing date of the claimed invention. A person of ordinary skill would have been motivated to prepare halogenated formic acid esters from the carbonyl halides produced in the claims of ‘121 because Akihiko teaches this is a well-known and predictable process. Therefore, using a compound for its intended use is not inventive. Also see MPEP 2143(I)(A).
Claim 7 is rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-8 of U.S. Patent No. 12421121 (‘121), as applied to claims 1-4 above, and further in view of Slocombe (“Phosgene Derivatives. The Preparation of Isocyanates, Carbamyl Chlorides and Cyanuric Acid” J. Am. Chem. Soc., 1950, p. 1888).
The teachings of Slocombe were discussed in a prior 35 USC 103 rejection and are incorporated herein. It would have been prima facie obvious to combine the claims of ‘121 and the teachings of Slocombe to arrive at the instantly claimed process with a reasonable expectation of success before the effective filing date of the claimed invention. A person of ordinary skill would have been motivated to prepare isocyanates from the carbonyl halides produced in the claims of ‘121 because Slocombe teaches this is a well-known and predictable process. Therefore, using a compound for its intended use is not inventive. Also see MPEP 2143(I)(A).
Claim 8 is rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-8 of U.S. Patent No. 12421121 (‘121), as applied to claims 1-4 above, and further in view of Gerlach (“Scale-Up Studies for the Asymmetric Julia-Colonna Epoxidation Reaction” Adv. Synth. Catal. 2004, p. 1247).
The teachings of Gerlach were discussed in a prior 35 USC 103 rejection and are incorporated herein. It would have been prima facie obvious to combine the claims of ‘121 and the teachings of Gerlach to arrive at the instantly claimed process with a reasonable expectation of success before the effective filing date of the claimed invention. A person of ordinary skill would have been motivated to prepare anhydrides of instant formula (VIII) from the carbonyl halides produced in the claims of ‘121 and compounds of instant formula (VII) because Gerlach teaches this is a well-known and predictable process. Therefore, using a compound for its intended use is not inventive. Also see MPEP 2143(I)(A).
Claim 9 is rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-8 of U.S. Patent No. 12421121 (‘121), as applied to claims 1-4 above, and further in view of Haveaux (“α-CHLORO ENAMINES, REACTIVE INTERMEDIATES FOR SYNTHESIS: 1-CHLORO-N,N,2-TRIMETHYLPROPENYLAMINE” Organic Syntheses, Coll. Vol. 6, p.282 (1988); Vol. 59, p.26 (1979)).
The teachings of Haveaux were discussed in a prior 35 USC 103 rejection and are incorporated herein. It would have been prima facie obvious to combine the claims of ‘121 and the teachings of Haveaux to arrive at the instantly claimed process with a reasonable expectation of success before the effective filing date of the claimed invention. A person of ordinary skill would have been motivated to prepare compounds of instant formula (X) from the carbonyl halides produced in the claims of ‘121 and compounds of instant formula (IX) because Haveaux teaches this is a well-known and predictable process. Therefore, using a compound for its intended use is not inventive. Also see MPEP 2143(I)(A).
Conclusion
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/AMY C BONAPARTE/ Primary Examiner, Art Unit 1692