DETAILED ACTION
STATUS OF THE APPLICATION
Receipt is acknowledged of Applicants’ Amendments and Remarks, filed 4 August 2023, in the matter of Application No. 18/264,360. Said documents have been entered on the record. The Examiner further acknowledges the following:
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Claims 1-15 are pending.
Claims 2-14 have been amended.
No claims have been cancelled.
Thus, claims 1-15 represent all claims currently under consideration.
Priority
Acknowledgment is made of Applicants’ claim for foreign priority under 35 U.S.C. 119 (a)-(d). The certified copy has been filed in the present application, filed 4 August 2023, and in parent Application No. PCT/EP2022/052847, filed on 7 February 2022. Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55. Applicant claims foreign priority to Application No. EP21155684.0, filed on 8 February 2021.
Domestic Priority data as claimed by applicant:
This application is a 371 of PCT/EP2022/052847 (02/07/2022)
Foreign Applications:
EUROPEAN PATENT OFFICE EP21155684.0 (02/08/2021)
Information Disclosure Statement (IDS)
The information disclosure statements submitted on 4 August 2023, 19 March 2025, and 9 July 2025 are in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statements are being considered by the Examiner.
The listing of references in the specification is not a proper information disclosure statement. 37 CFR 1.98(b) requires a list of all patents, publications, or other information submitted for consideration by the Office, and MPEP § 609.04(a) states, "the list may not be incorporated into the specification but must be submitted in a separate paper." Therefore, unless the references have been cited by the Examiner on form PTO-892, they have not been considered.
Specification
The disclosure is objected to because of the following informalities:
Experimental series 2-3 whose results are shown in Tables 2-3, respectively, each use Examples 9-11, but they refer to different experimental conditions and results (Specification; pages 14-15, Tables 2-3). The Examiner notes that amending the experimental Example numbering in Table 3, for instance if Examples 9-11 were to read as Examples 12-14, would adequately address this ambiguity.
The disclosure is objected to because of the following informalities:
The written description recites WO2017/131607 as a disclosure directed to an allene ketone that can be isomerized to an unsaturated ketone with hydrogen. However, WO2017/131607 is directed to an oxygen mask, and therefore this disclosure appears to have been made in error.
Appropriate correction is required.
Claim Objections
Claim 1 is objected to because of the following informalities:
In line 10, “…linear or branched or cyclic hydrocarbyl group…” should read “…linear, branched, or cyclic hydrocarbyl group…”
In line 13, “…R4 represents H or methyl or an ethyl group…” should read “…R4 represents H or a methyl or an ethyl group…”
In line 22, “…R6 and R7 and R8 and R9…” should read “…R6, R7, R8, and R9…”
Claim 11 is objected to because of the following informalities:
In lines 4 and 8, “…in case of…” should read “…in the case of…”
In line 8, “…formula (IIIa)…” should read “…formula (IIIb)…” as stated in the written description (Specification; page 9, line 7).
Claim 14 is objected to because of the following informalities:
In line 8, “…isomerization of compound of the formula (I)…” should read “…isomerization of the compound of the formula (I)…”
In line 9, “…preferable…” should read “…preferably…”
Claim 15 is objected to because of the following informalities:
In line 11, “…linear or branched or cyclic hydrocarbyl group…” should read “…linear, branched, or cyclic hydrocarbyl group…”
In line 14, “…R4 represents H or methyl or an ethyl group…” should read “…R4 represents H or a methyl or an ethyl group…”
In line 23, “…R6 and R7 and R8 and R9…” should read “…R6, R7, R8, and R9…”
Appropriate correction is required.
Claim Interpretation
Claim 14 recites in step a) “preparing a compound of the formula (I) according to claim 1”. For the purposes of examination, this method step is being interpreted as a product-by-process limitation. MPEP § 2113(I) states that “[E]ven though product-by-process claims are limited by and defined by the process, determination of patentability is based on the product itself. The patentability of a product does not depend on its method of production. If the product in the product-by-process claim is the same as or obvious from a product of the prior art, the claim is unpatentable even though the prior product was made by a different process.”
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 1-15 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.
A broad range or limitation together with a narrow range or limitation that falls within the broad range or limitation (in the same claim) may be considered indefinite if the resulting claim does not clearly set forth the metes and bounds of the patent protection desired. See MPEP § 2173.05(c).
In the present instance, claims 1 and 15 twice recite the broad recitation “C1-10-alkyl group”, and the claim also recites “particularly a methyl or an ethyl group” which is the narrower statement of the range/limitation.
Further regarding claims 1 and 15, these claims recite the broad recitation “C1-10-alkylene group”, and the claim also recites “particularly an ethylene or propylene group” which is the narrower statement of the range/limitation.
In the present instance, claim 8 recites the broad limitation “R30=R31=R32=R33=R34”, and the claim also recites “preferably “R30=R31=R32=R33=R34 = H”, which is the narrower statement of the range/limitation.
In the present instance, claim 10 recites the broad limitation “wherein n represents 1, 2, 3 or 4”, and the claim also recites “particularly 1 or 2”, which is the narrower statement of the range/limitation.
In the present instance, claim 11 recites the broad limitation “wherein the molar ratio of the compound of the formula (II) to the compound of the formula (IIIa) or (IIIb) is ranging from 1:15 to 1:1”, and the claim also recites
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which is the narrower statement of the range/limitation.
In the present instance, claim 12 recites the broad limitation “the ammonium catalyst is ranging from 0.01 - 1 mol-%”, and the claim also recites “preferably ranging from 0.02 - 0.6 mol-%, more preferably ranging from 0.05 - 0.6 mol-%”, which is the narrower statement of the range/limitation.
In the present instance, claim 14 recites the broad limitation “a base or an acid”, and the claim also recites “preferable a base”, which is the narrower statement of the range/limitation.
The claim(s) are considered indefinite because there is a question or doubt as to whether the feature introduced by such narrower language is (a) merely exemplary of the remainder of the claim, and therefore not required, or (b) a required feature of the claims.
Regarding claims 2-14, these dependent claims do not resolve the indefiniteness of claim 1 detailed above.
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.
Claims 1-3, 5, 9-13, and 15 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Wang et al. (“Solvent-free synthesis of unsaturated ketones by the Saucy-Marbet reaction using simple ammonium ionic liquid as a catalyst”; Green Chem. 2009, 11, 843-847; IDS of 08-04-2023; hereinafter “Wang”).
Regarding claims 1 and 15, Wang discloses the following process for the manufacture of an allene ketone in the presence of ionic liquid ammonium catalysts including [Et2NH2]HSO4, [Et3NH]HSO4, [Pr3NH]HSO4, and [Bu3NH]HSO4 via the Saucy-Marbet reaction (Wang; page 844; Scheme 1 and Table 1):
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The reactants and allene ketone product disclosed by Wang anticipates formulae (I), (II) and (IIIa) of instant claim 1 when R1 is a methyl group (corresponding to R2 of Wang), R2 is a branched unsaturated hydrocarbyl group with 6 C atoms or 11 C atoms (corresponding to R1 of Wang), R3 is a methyl group, R4 is H, and R5 is a methyl or an ethyl group (i.e., a C1 or C2 linear alkyl group, corresponding to R3 of Wang). In addition, the [Et2NH2]HSO4, [Et3NH]HSO4, [Pr3NH]HSO4, and [Bu3NH]HSO4 ammonium catalysts disclosed by Wang anticipate the ammonium catalyst formula of instant claim 1 when R6 = R7 = C2 linear alkyl, R8 = R9 = H, and X = [HSO4]– (as in [Et2NH2]HSO4 of Wang); when R6 = R7 = R8 = C2 linear alkyl, R9 = H, and X = [HSO4]– (as in [Et3NH]HSO4 of Wang); when R6 = R7 = R8 = C3 linear alkyl, R9 = H, and X = [HSO4]– (as in [Pr3NH]HSO4 of Wang); and when R6 = R7 = R8 = C4 linear alkyl, R9 = H, and X = [HSO4]– (as in [Bu3NH]HSO4 of Wang). Furthermore, the reaction mixture of Wang anticipates formula (II), formula (IIIa), and the ammonium catalyst formula of instant claim 15. Thus, the process of Wang anticipates every limitation of instant claims 1 and 15.
Regarding claim 2 depending from claim 1, the process of Wang discloses wherein R1 is a methyl group (Wang; page 844; Scheme 1, corresponding to R2 of Wang).
Regarding claim 3 depending from claim 1 and claim 5 depending from claim 3, the process of Wang discloses the use of [Et3NH]HSO4, [Pr3NH]HSO4, and [Bu3NH]HSO4 ammonium catalysts that are characterized in that R6 = R7 = R8 = C2 linear alkyl, and R9 = H (as in [Et3NH]HSO4); R6 = R7 = R8 = C3 linear alkyl, and R9 = H (as in [Pr3NH]HSO4); and R6 = R7 = R8 = C4 linear alkyl, R9 = H (as in [Bu3NH]HSO4), respectively (Wang; page 844, Table 1).
Regarding claim 9 depending from claim 1, the process of Wang discloses a reaction example using 2-methyl-3-butyn-2-ol as a reactant (Wang; page 845, Table 3), which the skilled artisan would recognize has the following structure:
This compound structure corresponds to a compound of formula (II) of instant claim 1, wherein R1 = R2 = methyl, and therefore anticipates the limitation of instant claim 9.
Regarding claim 10 depending from claim 1, the process of Wang discloses reaction examples with dehydrolinalool and dehydronerolidol as reactants (Wang; page 844, Scheme 1 and Table 1; page 845, Tables 2-3), whose structures correspond to wherein R2 is formula (R2-III) (as in dehydrolinalool, see Scheme 1 of Wang for molecular formula), and wherein R2 is formula (R2-IV) and wherein n represents 1 (as in dehydronerolidol, see Scheme 1 of Wang for molecular formula), respectively.
Regarding claims 11-12 depending from claim 1, the process of Wang discloses reaction conditions comprising 0.05 mol dehydrolinalool (i.e., a compound that anticipates formula (II) of instant claim 1), 0.15 mol 2-ethoxypropene (i.e., a compound that anticipates formula (IIIa) of instant claim 1), and 0.25 mmol of ammonium catalyst (e.g., [Et2NH2]HSO4, [Et3NH]HSO4, [Pr3NH]HSO4, and [Bu3NH]HSO4 ammonium catalysts that anticipate the ammonium catalyst formula of instant claim 1), as shown in Table 1 of Wang (Wang; page 844, Table 1). The molar ratio of dehydrolinalool to 2-ethoxypropene corresponds to a molar ratio of the compound of formula (II) to the compound of formula (IIIa) of 1:3, and the amount of ammonium catalyst based on the amount of the compound of formula (II) of 0.5 mol-%. This molar ratio and amount of ammonium catalyst reside within the range recited within the instant claims.
Regarding claim 13 depending from claim 1, the process of Wang discloses the preparation of a compound of the general formula (I) of instant claim 1, characterized in that the compound is 6,10-dimethyl-4,5,9-undecatrien-2-one, a key intermediate of Vitamin E and Vitamin A, is produced from 3,7-dimethyl-oct-6-en-1-yn-3-ol (dehydrolinalool) and 2-ethoxypropene by using the reported Saucy-Marbet reaction (Wang; page 843, Col. 1, paragraph 1; page 844; Scheme 1 and Col. 2, paragraph 2; page 845; Scheme 2).
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.
Claims 1-3, 5, and 9-15 are rejected under 35 U.S.C. 103 as being unpatentable over Wang et al. (“Solvent-free synthesis of unsaturated ketones by the Saucy-Marbet reaction using simple ammonium ionic liquid as a catalyst”; Green Chem. 2009, 11, 843-847; IDS of 08-04-2023; hereinafter “Wang”), in view of Bonrath et al. (US 2013/0197272 A1; hereinafter “Bonrath”).
Regarding claim 1, claims 2-3 and 9-13 depending from claim 1, claim 5 depending from claim 3, and claim 15, the teachings of Wang were discussed in the previous rejection and are incorporated herein.
Regarding claim 14 depending from claim 1, although Wang teaches preparing a compound of the formula (I) according to claim 1, as recited in method step a) of instant claim 14, Wang fails to teach a process for the manufacture of a diene ketone of the formula (IV), comprising the step of isomerization of a compound of the formula (I) in the presence of a base or an acid, preferably a base, to yield the diene ketone of the formula (IV), as recited in instant claim 14.
However, Bonrath teaches the isomerization of β-keto-allenes into the corresponding α,γ-dienones by treatment with a basic ion exchange resin (Bonrath; Title; Abstract; claim 1). Bonrath further teaches that α,γ-dienones are interesting compounds for the flavour and fragrance industry and valuable intermediates in the synthesis of carotenoids and vitamin A (Bonrath; paragraph [0002]).
Of particular note, Bonrath teaches the isomerization of 6,10-dimethyl-undeca-4,5,9-trien-2-one to 6,10-dimethyl-undeca-3,5,9-trien-2-one in the presence of a basic ion exchange resin (Bonrath; paragraph [0031]; Example 2; claim 7). The reactant 6,10-dimethyl-undeca-4,5,9-trien-2-one and reaction product 6,10-dimethyl-undeca-3,5,9-trien-2-one taught by Bonrath anticipates formula (I) (as defined in instant claim 1 on which claim 14 depends) and formula (IV) of instant claim 14 when R1 is a methyl group, R2 is a branched unsaturated hydrocarbyl group with 6 C atoms, R3 is a methyl group, and R4 is H. Furthermore, the process of Wang teaches the synthesis of valuable compounds in the flavors and fragrances industry, including the preparation of 6,10-dimethyl-undeca-4,5,9-trien-2-one (i.e., the isomerization starting material of Bonrath), a key intermediate for the production of Vitamin E and Vitamin A, in a manner consistent with instant claim 1 and step a) of instant claim 14, as detailed above (Wang; page 843, Col. 1, paragraph 1; page 844; Scheme 1 and Table 1; page 845, Scheme 2).
The prior art as taught by Wang and Bonrath reside in the closely overlapping technical field of the production of organic chemicals that are valuable intermediates for the flavor and fragrance industry and for the production of vitamin A. Thus, the cited prior art is in the same field of endeavor as the claimed invention and is therefore deemed analogous art, as described in MPEP § 2141.01(a). As such, the skilled artisan would be sufficiently motivated to modify the process of Wang to implement the isomerization method step of Bonrath to the allene ketone products of Wang (e.g., 6,10-dimethyl-undeca-4,5,9-trien-2-one) to pursue valuable chemical intermediates for the flavor and fragrance industry and for the production of vitamin A with a reasonable expectation of success. Such an endeavor would result in combining prior art elements according to known methods to yield predictable results, as described in MPEP § 2143(I)(A), and applying a known technique to a known device (method, or product) ready for improvement to yield predictable results, as described in MPEP § 2143(I)(D).
Therefore, it would have been prima facie obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to have modified Wang to incorporate the teachings of Bonrath to arrive at the claimed invention as described in instant claim 14. The motivation to do so would permit the skilled artisan to pursue, with a reasonable expectation of success, synthetic access to valuable chemical intermediates for the flavor and fragrance industry and for the production of vitamin A, as described above.
Claims 1-6 and 8-15 are rejected under 35 U.S.C. 103 as being unpatentable over Wang et al. (“Solvent-free synthesis of unsaturated ketones by the Saucy-Marbet reaction using simple ammonium ionic liquid as a catalyst”; Green Chem. 2009, 11, 843-847; IDS of 08-04-2023; hereinafter “Wang”), in view of Shi et al. (US 6,380,437 B1; IDS of 03-19-2025; hereinafter “Shi”) as evidenced by Bano et al. (“Economically Viable and Efficient Catalysts for Esterification and Cross Aldol Condensation Reactions under Mild Conditions”; ChemistrySelect 2020, 5, 4470-4477; hereinafter “Bano”).
Regarding claim 1, claims 2-3 and 9-13 depending from claim 1, claim 5 depending from claim 3, and claim 15, the teachings of Wang were discussed in the previous rejection and are incorporated herein.
Further regarding claim 1 and regarding claims 4 and 6-8 depending from claim 1, Wang fails to teach an embodiment comprising a reaction of a compound of the formula (IIIb), and a reaction carried out in the presence of an ammonium catalyst of the formula
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wherein R30, R31, R32, R33, and R34 represent independently from each other either H or a linear or branched C1-12-alkyl or cycloalkyl group, and X = [HSO4]– or [HS2O3]–, as recited in instant claim 1.
However, Shi teaches a process for the preparation of unsaturated 4,5-allene ketones by the Saucy-Marbet reaction by reacting tertiary propargylic alcohols with alkenyl ethers or ketals in the presence of aliphatic sulfonic acids or sulfonic acid salts, including the preparation of 6,10-dimethyl-undeca-4,5,9-trien-2-one from 3,7-dimethyl-6-octen-1-yn-3-ol (dehydrolinalool), in a manner consistent with the process of Wang and instant claim 1 (Shi; Title; Col. 1, lines 5-12; Col. 2, formula IV; line 59; claims 1 and 3).
Of particular note, Shi teaches that ketals of the following general formula IV can be employed as an alternative to alkenyl alkyl ethers:
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wherein R4 and R6 represent a C1 to C4 alkyl and R5 represents hydrogen or a C1 to C4 alkyl (Shi; claim 1). The genus of formula IV of Shi overlaps significantly with the genus of formula (IIIb) of instant claim 1. Furthermore, the skilled artisan would recognize that in order to arrive at the product 6,10-dimethyl-undeca-4,5,9-trien-2-one from 3,7-dimethyl-6-octen-1-yn-3-ol (dehydrolinalool) using the aforementioned ketal as taught by Shi, the compound of formula IV of Shi would require R4 to be methyl and R5 to be hydrogen, respectively, in a manner consistent with both the process of Wang and the instantly claimed invention.
Thus, the skilled artisan would recognize that the alkenyl alkyl ether starting materials of Wang (c.f., Wang; page 844; Scheme 1) could be substituted with the corresponding ketal starting materials of Shi as a suitable alternative with a reasonable expectation of success, because both Wang and Shi teach that 6,10-dimethyl-undeca-4,5,9-trien-2-one can be obtained from 3,7-dimethyl-6-octen-1-yn-3-ol (dehydrolinalool) with either alkenyl alkyl ethers or ketals, respectively. Such an endeavor would result in the simple substitution of one known element for another to obtain predictable results, as recited in MPEP § 2133(I)(B).
Further regarding claim 1 and claims 4, 6, and 8 depending from claim 1, Shi further teaches that suitable sulfonic acid salt catalysts for the Saucy-Marbet process include pyridinium p-toluenesulfonate and tetramethylammonium p-toluenesulfonate (Shi; claim 6 and Col. 3, lines 27-32).
Although Shi fails to teach ammonium catalysts comprising pyridinium salts of [HSO4]– or [HS2O3]–, as recited in instant claim 1, Wang discloses the use of alkylammonium salts of [HSO4]–, as detailed above (Wang; page 844, Table 1). Wang further teaches that although the Saucy-Marbet reaction can be carried out in the presence of various acids used as catalysts including p-toluenesulfonic acid, the separation and recycling of the catalysts are difficult and the reaction usually calls for volatile organic solvents such as halohydrocarbon, toluene, and petroleum ether (Wang; page 843; Col. 1, paragraph 1). Therefore, the process of Wang is directed towards ionic liquids, including ammonium and imidazolium salts of [HSO4]–, to catalyze the Saucy-Marbet reaction under solvent-free conditions that eliminate the need for a volatile organic solvent and are very easy to separate and reuse (Wang; page 844, Col. 1, paragraph 1 and Table 1).
Finally, the utility and superior reactivity of pyridinium hydrogensulfate ([PyH][HSO4]) and triethylammonium hydrogensulfate [Et3NH][HSO4] as a Brønsted acidic ionic liquids and catalysts in organic chemical reactions is further evidenced by Bano, who teaches that ([PyH][HSO4]) (1a) and [Et3NH][HSO4] (2a) exhibit superior reactivity compared to pyridinium p-toluenesulfonate (1e) and triethylammonium p-toluenesulfonate (2e), respectively, in acid-catalyzed esterification and crossed aldol reactions (Bano; Title; page 4471, Scheme 1 and Figure 1; page 4472, Table 1 and Col. 1, paragraph 1; page 4474, Table 4).
The prior art as taught by Wang and Shi reside in the closely overlapping technical field of allene ketone production via the Saucy-Marbet reaction under acid catalysis with ammonium salts. Furthermore, both Wang and Bano teach the utility and advantages of alkylammonium and/or pyridinium hydrogensulfate ionic liquids as acidic catalysts in organic chemical reactions. Thus, the cited prior art is in the same field of endeavor as the claimed invention and is therefore deemed analogous art, as described in MPEP § 2141.01(a). As such, the skilled artisan would be sufficiently motivated to modify the process of Wang to incorporate teachings of Shi and Bano to incorporate the tetramethylammonium and pyridinum salts of Shi wherein the p-toluenesulfonate anion is replaced with hydrogensulfate to arrive at tetramethylammonium hydrogensulfate and pyridinum hydrogensulfate in a manner consistent with the catalysts described in instant claims 1, 4, 6, and 8 to pursue alternative acidic ionic liquid catalysts that are easy to separate and reuse with a reasonable expectation of success. Such an endeavor would result in combining prior art elements according to known methods to yield predictable results, as described in MPEP § 2143(I)(A), and applying a known technique to a known device (method, or product) ready for improvement to yield predictable results, as described in MPEP § 2143(I)(D). Finally, the skilled artisan would recognize that the alkenylalkyl ether starting materials of Wang (c.f., Wang; page 844; Scheme 1) could be substituted with the corresponding ketal starting materials of Shi as an obvious alternative with a reasonable expectation of success, as detailed above. MPEP § 2143(I)(B).
Therefore, it would have been prima facie obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to have modified Wang to incorporate the teachings of Shi and supportive teachings of Bano to arrive at the claimed invention as described in instant claims 1, 4, 6, and 8. The motivation to do so would permit the skilled artisan to pursue, with a reasonable expectation of success, an obvious alternative starting material for the Saucy-Marbet reaction and alternative catalysts that react under solvent-free conditions, eliminate the need for a volatile organic solvent, and are very easy to separate and reuse, as described above.
Regarding claim 14 depending from claim 1, Shi teaches that the allene products, which includes 6,10-dimethyl-undeca-4,5,9-trien-2-one (i.e., a compound of formula (I) of instant claim 1), can either be isolated directly or converted by basic isomerization into a 3,5-dienone of the general form:
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wherein R1 and R2 represent a hydrogen, a saturated or unsaturated, branched or unbranched C1 to C20-alkyl, aryl or alkylaryl; R1 and R2 together to form a 5- or 6-membered ring; R3 and R5 represent hydrogen or a C1 to C4-alkyl and R4 represents a C1 to C4 alkyl (Shi; claims 1-2; Col. 1, lines 11-13 and 15-17; Col. 4, lines 3-16). Shi further teaches that the 3,5-dienone compounds can be used as important intermediates for vitamins A, E, K1, and carotenoids (Shi; Col. 4, lines 17-18).
Thus, the skilled artisan would recognize that compounds of formula (I) of instant claim 1 (e.g., 6,10-dimethyl-undeca-4,5,9-trien-2-one) as taught by Wang and Shi could be further subjected to basic isomerization as taught by Shi to arrive at the corresponding 3,5-dienone (e.g., 6,10-dimethyl-undeca-3,5,9-trien-2-one) to pursue important intermediates for vitamins A, E, K1, and carotenoids. Therefore, as with claim 1, it would be been prima facie obvious to arrive at the claimed invention based on the teachings of Wang in view of Shi as evidenced by Bano.
Claim 7 is rejected under 35 U.S.C. 103 as being unpatentable over Wang et al. (“Solvent-free synthesis of unsaturated ketones by the Saucy-Marbet reaction using simple ammonium ionic liquid as a catalyst”; Green Chem. 2009, 11, 843-847; IDS of 08-04-2023; hereinafter “Wang”), in view of Shi et al. (US 6,380,437 B1; IDS of 03-19-2025; hereinafter “Shi”) as evidenced by Bano et al. (“Economically Viable and Efficient Catalysts for Esterification and Cross Aldol Condensation Reactions under Mild Conditions”; ChemistrySelect 2020, 5, 4470-4477; hereinafter “Bano”) as applied to claims 1-6 and 8-15 above, and further in view of Tao et al. (“Kinetics Study of the Ketalization Reaction of Cyclohexanone with Glycol Using Brønsted Acidic Ionic Liquids as Catalysts”; Ind. Eng. Chem. Res. 2012, 51, 16263-16269; hereinafter “Tao”).
Regarding claim 7, claim 1 is rendered obvious over Wang in view of Shi as evidenced by Bano, as detailed above.
Wang, Shi, and Bano fail to explicitly teach the process according to claim 1, characterized in that one or two groups of R30, R31, R32, R33, and R34 represent a methyl group, as recited in instant claim 7.
However, Tao teaches that Brønsted acidic ionic liquids (BAILs) have several advantages in the acid-catalyis reaction, which avoids the technical issues raised from mineral acids (Tao; Abstract). Tao further teaches that ionic liquids as environmentally-friendly reaction media have attracted significant attention for their unique properties, such as excellent thermal stability, negligible vapor pressure, tunable acidity, remarkable solubility, and effortless reusability (Tao; page 16263; Col. 1, paragraph 2). Of particular note, Tao teaches the preparation and characterization of six BAILs composed of the [HSO4] anion and different cations, including 2-methylpyridinium hydrogensulfate ([Hmpy][HSO4]; Tao; page 16264, Figure 1):
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Tao further demonstrates that [Hpy][HSO4] and [Hmpy][HSO4] are promising substitutes for corrosive mineral acids and solid resins in the production of ketals, to overcome the technical difficulties such as serious equipment corrosion and high mass transfer resistance (Tao; 16265; Col. 1, paragraphs 1-2 and Col. 2, paragraph 1).
The prior art as taught by Wang, Shi, Bano, and Tao reside in the overlapping technical field of acid-catalyzed organic chemical reactions. Furthermore, Wang, Bano, and Tao teach the utility and advantages of alkylammonium and/or pyridinium hydrogensulfate ionic liquids as acidic catalysts in organic chemical reactions. Thus, the cited prior art is in the same field of endeavor as the claimed invention and is therefore deemed analogous art, as described in MPEP § 2141.01(a). As such, the skilled artisan would be sufficiently motivated to select structurally similar ionic liquid catalysts, such as the 2-methylpyridinium hydrogensulfate ([Hmpy][HSO4]) catalyst of Tao, with a reasonable expectation of success. Such an endeavor would result in choosing from a finite number of identified, predictable solutions, with a reasonable expectation of success and would therefore be “obvious to try”, as described in MPEP § 2143(I)(E).
Therefore, it would have been prima facie obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to have modified Wang, Shi, and Bano to incorporate the teachings of Tao to arrive at the claimed invention. The motivation to do so would permit the skilled artisan to pursue, with a reasonable expectation of success, an obvious alternative catalyst for the claimed Saucy-Marbet process that offers several advantages such as excellent thermal stability, negligible vapor pressure, tunable acidity, remarkable solubility, effortless reusability, and the ability to overcome the technical difficulties such as serious equipment corrosion and high mass transfer resistance, as described above.
Based on the combined teachings of the references, the Examiner submits that a person of ordinary skill in the art would have had a reasonable expectation of success of arriving at the instantly claimed process. Therefore, the invention as a whole would have been prima facie obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, and absent a clear showing of evidence to the contrary.
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 1-2 and 6-15 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-12 of copending Application No. 18/264,390.
Although the claims at issue are not identical, they are not patentably distinct from each other.
Regarding instant claim 1, claim 1 of copending Application No. 18/264,390 teaches the following:
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Wherein the R group definitions are identical to the definitions of instant claim 1, and wherein X is [HSO4]– or [HS2O3]–.
Regarding instant claims 2 and 6-14, claims 2-11 of copending Application No. 18/264,390 teach every limitation of the instant claims.
Regarding instant claim 15, claim 12 of copending Application No. 18/264,390 teaches the following:
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Wherein the R group definitions are identical to the definitions of instant claim 1, and wherein X is [HSO4]– or [HS2O3]–.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Conclusion
Any inquiry concerning this communication or earlier communications from the Examiner should be directed to Derek Rhoades whose telephone number is (703)-756-5321. The Examiner can normally be reached Monday–Thursday, 7:30 am–5:00 pm EST; Friday, 7:30 am–4:00 pm EST.
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/D.R./Examiner, Art Unit 1692
/AMY C BONAPARTE/Primary Examiner, Art Unit 1692
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