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 .
DETAILED ACTION
Claim Status
Claims 1, 3-5, 9 and 13-21 are pending. Claims 1, 3-5, 9 and 13-21 are under examination. Claims 1, 3-5, 9 and 13-21 are rejected. No Claims allowed.
Filing Receipt
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Response to Amendments
Applicant's amendments and arguments filed 02/19/2026 are acknowledged and have been fully considered. The Examiner has re-weighed all the evidence of record. Any rejection and/or objection not specifically addressed below in original or modified form is herein withdrawn.
Withdrawn Rejections
The 112(a) rejection of claims 1, 3-5 and 9-13 in the non-final mailed 11/07/2025 is withdrawn. The claim amendments have overcome the rejection.
The 112(b) rejection of claims 13-14 in the non-final mailed 11/07/2025 is withdrawn. The claim amendments have overcome the rejection.
The 112(d) rejection of claims 10-12 in the non-final mailed 11/07/2025 is withdrawn. Claims 10-12 were cancelled.
The following newly applied 112(a) and two modified 103(a) rejections constitute the complete set of rejections and/or objections presently being applied to the instant application.
Response to Arguments
Applicant's arguments filed 02/19/2026 have been fully considered but they are not persuasive.
Applicant’s arguments are based on unexpected, good yields of at least 85% diastereomeric excess and cites Example 1-9.
Applicant argues catalyst yields are unpredictable and cites Examples 1 and 9 having yields of 87% ee while Example 10 utilizing a 2-phenylethyl substituted substrate gives a yield of only 80% ee.
The reaction in Example 10 which only achieves 80%, is a reaction encompassed by the current claims. The substrate in Example 10 being reduced is compound 3C wherein R1 is 2-phenyl ethyl. See immediately below and page 36 of the current specification.
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The unexpected, good yields of at least 85% diastereomeric excess do not occur when R1 is 2-phenyl ethyl. The purported unexpected result is not commensurate in scope with the claims.
Concerning the references supplied to purportedly substantiate the unpredictable compatibility of substrate and ligand catalyst, the prior art McWilliams in the original rejection explicitly teach “the hydrogenation of α,β-unsaturated ketone occurs enatioselectively and chemoselectvely at the ketone group using catalysts of type 1-3, providing high yields of enatioenriched allylic alcohols” p. 5, top left). Type 2 catalyst is seen below. Note: the claimed compound (3) is an α,β-unsaturated ketone.
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Starting from the vantage point that the above catalyst in the prior art produces high yields of enantioenriched allylic alcohols from α,β-unsaturated ketones of which is the currently claimed substrate, sets the stage for obtaining the high enriched yields as asserted by the applicant. The articles supplied by applicant do pertain to enantioselectivity yields with respect to catalysts, but do not specifically point to the unpredictable nature of the catalysts in the reference McWilliams with respect to α,β-unsaturated ketone substrates taught by McWilliams. Note: the claimed compound (3) is an α,β-unsaturated ketone.
Concerning the experimental data (e.g. Examples 1-9), yes the examples show a yield at or above 85% with variable R1 being n-pentyl and 2-methylhexyl (Example 1 and 9 respectively), however as discussed above the experimental data that generates at least 85% is not commensurate in scope with the claims. See Example 10, page 36 of the current specification.
Concerning the Comparative Examples 1-5, these examples do show a substantially less percent yield as evident in Table 1 in the current specification page 27. However, each reaction variable including the catalyst, catalytic amount, reducing agent, base solvent system and reaction temperature was changed with respect to working examples 1-9.
To properly show a true side-by-side comparison for example of the claimed catalyst, initially the other reaction parameters should necessarily be identical to accurately compare the percent yield with respect to the catalyst. Too many variables were altered to compare the working examples to the comparative examples. For example, formic acid or the use of neat THF may be the culprit in the substantial undermining of the percent yields. However, with all other parameters altered, the determination cannot be made. One cannot determine if all of the parameters in the working examples are necessary to achieve the claimed percent yields, without knowing the individual contributions of each individual parameter.
For the reasons stated above the obviousness rejection is maintained/modified
as set forth below.
Claim Rejections - 35 USC § 112
The following is a quotation of the first paragraph of 35 U.S.C. 112(a):
(a) IN GENERAL.—The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor or joint inventor of carrying out the invention.
The following is a quotation of the first paragraph of pre-AIA 35 U.S.C. 112:
The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor of carrying out his invention.
Claims 1, 3-5, 9, and 13-21 rejected under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, as failing to comply with the written description requirement. The claim(s) contains subject matter which was not described in the specification in such a way as to reasonably convey to one skilled in the relevant art that the inventor or a joint inventor, or for applications subject to pre-AIA 35 U.S.C. 112, the inventor(s), at the time the application was filed, had possession of the claimed invention.
The newly added limitation “(iii) the compound represented by formula (4) is produced with a diastereomeric excess of at least 85%” and/or 85%-94% when variable R1 is a C1-8 alkyl group that is substituted with a phenyl group, or more specifically R1 is 2-phenyl ethyl is new matter.
For example, per the above arguments, Example 10 of the specification wherein
R1 is 2-phenyl ethyl (a C2 alkyl group that is substituted with a phenyl group) results in
an 80% yield and not the claimed at least 85%.
After careful review, no support for the newly added limitation was found in the original disclosure. Applicant is invited to point to clear support or specific examples of the claimed limitation in the specification as-filed or remove such amendatory language in response to this action.
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) 1, 3-5, 9, 13 and 15-20 is/are rejected under 35 U.S.C. 103 as being unpatentable over Dammalapati et al. (WO2012/011128, Published 01-2012. Cited in IDS filed 09/24/2021 as reference AL), McWilliams ((R)- and (S)-2,2′-Bis(bis(3,5-dimethylphenyl)phosphanyl)-1,1′-binaphthalene, 14 pages, Published 04-2015) and Hirano et al. (USPGPub 2020/0317659, Published 10-2020 with a PCT filing
date of 05-2018).
The modifications to this rejection were necessitated by amendment.
Scope of the Prior Art
Dammalapati et al. teach the following (p. 3-4).
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Wherein, R1 is a C1-8 alkyl group substituted with a phenyl group, R2 is (2a), R3 is an alkoxy group, Ar1 and Ar3 are p-benzoyl and p-nitrobenzoyl.
Dammalapati et al. teach the definition of alkoxy as methoxy, ethoxy, propoxy… (p. 17). These alkoxies read on the current C1-3 alkoxy R3 variable.
Concerning claim 3, Dammalapati et al. teach variable Ar1 is a phenyl group (bottom of page 4). Current claims 15-16.
Concerning claim 4 and 9, Dammalapati et al. teach variable R1 to be a 2-phenylethyl group (all of page 4, multiple figures). Current claims 15-17.
Concerning claim 5 and the compound represented by Formula (6), Dammalapati et al. teach p-nitrobenzoyl chloride, X being chlorine (example 2, page 19). Ar3 being an aryl group substituted in the para position with a nitro group (p. 4 of Reference Dammalapati et al.).
Ascertaining the Difference
Dammalapati et al. does not teach the use of the metal complex (catalyst) represented by formula (5) nor the inorganic base and solvent during the stereo selective reduction, nor the diastereomeric excess of at least 85% and/or excess of 85%-94%.
Secondary Reference
McWilliams teach “the hydrogenation of α,β-unsaturated ketone occurs enatioselectively and chemoselectvely at the ketone group using catalysts of type 1-3, providing high yields of enatioenriched allylic alcohols” p. 5, top left). Type 2 catalyst is seen below on the next page. Note: the claimed compound (3) is an α,β-unsaturated ketone.
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Current variable Ar2 is a 3,5-dimethylphenyl group (current claims 15-16), W is binapththyl, Z is an ethylene group substituted with a C1 alkoxyphenyl group and C3 alkyl. L is one of the carbon atoms constituting the C1 alkoxyphenyl group (current claim 13). The above catalyst is (S)RUCY-xylBINAP.
Moving on, McWilliams teach screening and/or comparing known Ru catalysts utilized in asymmetric reduction of ketones to determine the performance of the catalysts with varying substrates (see page 2, left column and the remainder of the document).
Concerning the hydrogen atmosphere McWilliams teach hydrogen in hydrogenation reactions on page 2-4.
Concerning the temperatures, McWilliams teach overlapping temperatures as claimed. Top of page 4, 23C, and right side of page 4, 25C.
Concerning the solvents, McWilliams teach a mixture of tetrahydrofuran and isopropyl alcohol (IPA), page 4 left column and IPA page 4 right column.
Hirano et al. teach an asymmetric reduction reaction that involves ruthenium catalysts with hydrogen, bases: potassium tert-butoxide; tripotassium phosphate; and cesium carbonate and solvents: tetrahydrofuran; methanol; ethanol; n-propanol; isopropyl alcohol; and n-butanol. (par. 170, 181, 189-190, 195, 199, 203, 208-209, 279 and 286).
Hirano et al. generally teach transition metal complexes which have the ability to
catalyze an asymmetric hydrogenation (par. 199).
Hirano et al. teach (par. 201) transition metal that overlap with the ruthenium taught by McWilliams.
Hirano et al. generally teach overlapping ligands to the ligands taught by McWilliams. See Hirano et al. paragraph 199, 203, daipen, dpen and see Hirano et al. paragraph 208 xyl-BINAP.
Hirano et al. teach overlapping bases and solvents taught by McWilliams. See Hirano et al. paragraph 279, potassium tert-butoxide and paragraph 286 tetrahydrofuran and isopropyl alcohol.
The above teachings render McWilliams and Hirano et al. analogous art to the invention and overlapping in nature.
Obviousness
It would have been prima facie obvious for an ordinary artisan before the effective filing date of the claimed invention to have tried the appropriate stereo catalyst of the type 2 catalyst taught by McWilliams, with H2, THF/IPA and an inorganic base as taught by McWilliams in the reductive hydrogenation of compound (3) to (4) as taught by Dammalapati et al. to arrive at the current invention.
The ordinary artisan would have done so reasonable expectation of success because McWilliams teach “the hydrogenation of α,β-unsaturated ketone occurs enatioselectively and chemoselectvely at the ketone group using catalysts of type 1-3, providing high yields of enatioenriched allylic alcohols” (p. 5, top left). MPEP 2141 III (B)
and/or (E).
Moreover, it would have been obvious through routine experimentation to have
tried known asymmetric ketone reduction catalysts and arrive at optimal substrate/catalyst paring. Especially with the teachings of McWilliams in mind. MPEP 2144.05 II. A. and B. “[W]here the general conditions of a claim are disclosed in the prior art, it is not inventive to discover the optimum or workable ranges by routine experimentation.” In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955).
Concerning the claimed temperatures, MPEP 2144.05 I.: “In the case where the
claimed ranges “overlap or lie inside ranges disclosed by the prior art” a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976).”
Concerning the solvents, McWilliams teach overlapping solvents and explicitly teaches THF/IPA.
The ordinary artisan would have then looked to the teachings of Hirano et al. due to the overlapping teachings of Hirano et al. and McWilliams and would have found overlapping bases and solvents. It would have been obvious to substitute known bases and solvents that are utilized in asymmetric hydrogenation reduction reactions. See MPEP 2141 III (B).
After combining and utilizing the catalysts and reactants/reagents as argued to have been obvious, the ordinary artisan would have arrived at the claimed diastereomeric excesses with a reasonable expectation of success because McWilliams teach “the hydrogenation of α,β-unsaturated ketone occurs enatioselectively and chemoselectvely at the ketone group using catalysts of type 1-3, providing high yields of enatioenriched allylic alcohols” (p. 5, top left).
Claim(s) 14 and 21 is/are rejected under 35 U.S.C. 103 as being unpatentable over Dammalapati et al. (WO2012/011128, Published 01-2012. Cited in IDS filed 09/24/2021 as reference AL), McWilliams ((R)- and (S)-2,2′-Bis(bis(3,5-dimethylphenyl)phosphanyl)-1,1′-binaphthalene, 14 pages, Published 04-2015) and Hirano et al. (USPGPub 2020/0317659, Published 10-2020 with a PCT filing date of 05-2018) as applied to claims 1, 3-5 and 9-13 and in further view of Naitou
et al. (USPGPub 2016/0362369, Published 12-2016).
Scope of the Prior Art
The teachings of Dammalapati et al., McWilliams, and Hirano et al. are written in the above 103 and are incorporated by reference.
As a reminder, McWilliams teach (S)RUCY-xylBINAP. Additionally, McWilliams teach ruthenium complexes containing xylBINAP have demonstrated broad scope in the enatioselective hydrogenation of ketones (p. 1, right column). The (R)RUCY-xylBINAP of claim 14 contains xylBINAP.
Moving on, McWilliams teach screening and/or comparing known Ru catalysts utilized in asymmetric reduction of ketones to determine the performance of the catalysts with varying substrates (see page 2, left column and the remainder of the document).
Ascertain the Differences
The prior art does not explicitly teach (R)RUCY-xylBINAP as depicted current claim 14, nor the diastereomeric excess of at least 85% and/or excess of 85%-94%.
Secondary References
Naitou et al. teach (R)RUCY-xylBINAP utilized in a stereoselective reaction converting a ketone to an alcohol (p. 3). Note: (R)RUCY-xylBINAP contains both the xylBINAP and DAIPEN ligands chelated to a ruthenium center as in (S)RUCY-xylBINAP and the current variable L being a carbon as in (S)RUCY-xylBINAP taught by McWilliams. Thus, overlap exists with respect to the prior art. Moreover, the teaching of
(R)RUCY-xylBINAP renders Naitou et al. analogous art to the invention.
Obviousness
It would have been prima facie obvious for an ordinary artisan before the effective filing date of the claimed invention to have tried with a reasonable expectation of success the (R)RUCY-xylBINAP taught by Naitou et al. in the claimed reaction arrived at by the ordinary artisan in the first 103 rejection. In doing so the ordinary artisan would have arrived at the invention of current claim 14.
The ordinary artisan would have had a reasonable expectation of success due to ruthenium complexes containing xylBINAP have demonstrated broad scope in the enatioselective hydrogenation of ketones and that a chiral alternative (S)RUCY-xylBINAP was taught by McWilliams to provide high yields of enatioenriched allylic alcohols from α,β-unsaturated ketones.
The ordinary artisan would have looked to the teachings of Naitou et al. due to
the catalyst being taught overlaps with the teachings of McWilliams with respect to the ruthenium complex containing xylBINAP and DAIPEN and that both references
are pertaining to enatioselective hydrogenation of ketones.
Moreover, it would have been obvious through routine experimentation to have tried known asymmetric ketone reduction catalysts and arrive at optimal substrate/catalyst paring. Especially with the teachings of McWilliams in mind. MPEP 2144.05 II. A. and B. “[W]here the general conditions of a claim are disclosed in the prior art, it is not inventive to discover the optimum or workable ranges by routine experimentation.” In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955).
After combining and utilizing the catalysts and reactants/reagents as argued to have been obvious, the ordinary artisan would have arrived at the claimed diastereomeric excesses with a reasonable expectation of success because McWilliams teach “the hydrogenation of α,β-unsaturated ketone occurs enatioselectively and chemoselectvely at the ketone group using catalysts of type 1-3, providing high yields of enatioenriched allylic alcohols” (p. 5, top left).
Conclusion
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to BLAINE G DOLETSKI whose telephone number is (571)272-2766. The examiner can normally be reached M-F 7-4 EST.
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/B.G.D/ Examiner, Art Unit 1692 /Andrew D Kosar/Supervisory Patent Examiner, Art Unit 1625
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