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 .
Status of the Claims
The amendment filed on 11/20/2025 has been entered. Claims 3, 8, 15 and 28 have been amended. Claims 1-8, 13, 15-16, 21-24, 27-30 and 32-33 are thus currently pending.
Election/Restrictions
Applicant’s election of Group I, claims 1-8, 13 and 15-16 in the reply filed on 11/20/2025 is acknowledged. Because applicant did not distinctly and specifically point out the supposed errors in the restriction requirement, the election has been treated as an election without traverse (MPEP § 818.01(a)).
Claims 21-24, 27-30 and 32-33 are withdrawn by the examiner from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention, there being no allowable generic or linking claim.
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.
Claim 15 is 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 claim has been amended to recite the limitations: “wherein the alcohol has a formula selected from C2(H/D)5O(H/D), (CD3)2CHO(H/D), (CD3)2C(H/D)OD and D2O, CD4O, and (CD3)3COD”. However, the specification fails to disclose, either explicitly or implicitly, the entire claimed formulas of alcohols other than C2H5O(H/D), (CH3)2CHO(H/D), 2-propanol ((CH3)2CHOH), deuterated 2-propanol (IPA-d8) ((CD3)2CDOD), D2O, MeOD (CH3OD), and tBuOD ((CH3)3COD) ([0072], [00611] Table 1, [00725] Table S1, [00731], [00894] Scheme 1, [00897] Table 1, [00899], [00974], and [00975]).
Thus, at the time the application was filed, a skilled artisan would not recognize from the disclosure that Applicant was in possession of the entire species of the formula C2(H/D)5O(H/D), (CD3)2CHO(H/D), (CD3)2C(H/D)OD and D2O, CD4O, and (CD3)3COD except for C2H5O(H/D), (CH3)2CHO(H/D), 2-propanol ((CH3)2CHOH), deuterated 2-propanol (IPA-d8) ((CD3)2CDOD), D2O, MeOD (CH3OD), and tBuOD ((CH3)3COD).
MPEP § 2163.06 notes: " If new matter is added to the claims, the examiner should reject the claims under 35 U.S.C. 112(a) or pre-AIA 35 U.S.C. 112, first paragraph - written description requirement. In re Rasmussen, 650 F.2d 1212, 211 USPQ 323 (CCPA 1981)"
MPEP § 2163.02 states that “Whenever the issue arises, the fundamental factual inquiry is whether the specification conveys with reasonable clarity to those skilled in the art that, as of the filing date sought, applicant was in possession of the invention as now claimed. See, e.g., Vas-Cath, Inc. v. Mahurkar, 935 F.2d 1555, 1563-64, 19 USPQ2d 1111, 1117 (Fed. Cir. 1991). An applicant shows possession of the claimed invention by describing the claimed invention with all of its limitations using such descriptive means as words, structures, figures, diagrams, and formulas that fully set forth the claimed invention. Lockwood v. Am. Airlines, Inc., 107 F.3d 1565, 1572, 41 USPQ2d 1961, 1966 (Fed. Cir. 1997). Possession may be shown in a variety of ways including description of an actual reduction to practice, or by showing that the invention was "ready for patenting" such as by the disclosure of drawings or structural chemical formulas that show that the invention was complete, or by describing distinguishing identifying characteristics sufficient to show that the applicant was in possession of the claimed invention. See, e.g., Pfaff v. Wells Elecs., Inc., 525 U.S. 55, 68, 119 S.Ct. 304, 312, 48 USPQ2d 1641, 1647 (1998); Regents of the Univ. of Cal. v. Eli Lilly, 119 F.3d 1559, 1568, 43 USPQ2d 1398, 1406 (Fed. Cir. 1997); Amgen, Inc. v. Chugai Pharm., 927 F.2d 1200, 1206, 18 USPQ2d 1016, 1021 (Fed. Cir. 1991) (one must define a compound by "whatever characteristics sufficiently distinguish it").”
MPEP § 2163.06 further notes " When an amendment is filed in reply to an objection or rejection based on 35 U.S.C. 112(a) or pre-AIA 35 U.S.C. 112, first paragraph, a study of the entire application is often necessary to determine whether or not "new matter" is involved. Applicant should therefore specifically point out the support for any amendments made to the disclosure."
This is a new matter rejection.
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 3 and 6-7 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.
Regarding claims 3 and 6, the phrase "such as" renders the claim indefinite because it is unclear whether the limitations following the phrase are part of the claimed invention. See MPEP § 2173.05(d).
Regarding claim 3, the parenthetical limitation "optionally a carbocycle aryl moiety or a heterocycle aryl moiety" renders the claim indefinite because it is unclear whether the limitation is part of the claimed invention.
Regarding claim 6, the variable R13 of formula
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is indefinite because it has not been defined in the claim. Furthermore, the variable R11 (line 10) renders the claim vague and indefinite because it is unclear which group of the recited chemical formulas refers to, as the only groups presented in the formulas are R1-R10 and R12-R13.
Claim 7 is also rendered indefinite for its dependency on claim 6.
Claim 15 recites the limitation "D2O" in line 2. There is insufficient antecedent basis for this limitation in the claim as D2O is not the alcohol required by claim 1.
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 1-4, 6-8, 13 and 15-16 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Guo (Guo, S. et al. “Enantioselective Synthesis of β-Amino Acid Derivatives Enabled by Ligand-Controlled Reversal of Hydrocupration Regiochemistry” Angew. Chem. Int. Ed. 2020, 59, 20841–20845, doi.org/10.1002/anie.202007005, First published: 29 June 2020; cited in 11/15/2024).
Regarding claims 1-4, 6-7, 13 and 15-16, Guo teaches a method for preparing a deuterated compounds Re1 and Re2 (pg. 20844, Scheme 3A):
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wherein the method comprises reacting a reaction mixture comprising:
(i) 1a as a substrate compound comprising an alkene functionality o;
(ii) Cu as a transition metal catalyst;
(iii) (S)-BINAP and (S,S)-Ph-BPE as a phosphine ligand for the transition metal catalyst;
(iv) Me(MeO)2SiH as a substituted silane comprising a donor hydrogen atom;
(v) CD3OD as an alcohol comprising a donor deuterium atom; and
(vi) CPME as a solvent;
wherein the reaction mixture is reacted under conditions such that the alkyne functionality of the substrate compound is reductively deuterated to provide the deuterated compound.
Regarding claim 8, the structures of (S)-BINAP are as follows:
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Claims 1-4, 6-7 and 15-16 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Semba (Semba, K. et al. “Copper-Catalyzed Highly Selective Semihydrogenation of Non-Polar Carbon-Carbon Multiple Bonds using a Silane and an Alcohol” Adv. Synth. Catal. 2012, 354, 1542–1550, DOI: 10.1002/adsc.201200200; cited in 11/15/2024).
Regarding claims 1-4, 6-7 and 15-16, Semba teaches a method for preparing a deuterated compound 2j-d1 (pg. 1547, last scheme):
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wherein the method comprises reacting a reaction mixture comprising:
(i) 1j as a substrate compound comprising an alkyne functionality o;
(ii) Cu as a transition metal catalyst;
(iii) CF3Ar-Xan as a phosphine ligand for the transition metal catalyst;
(iv) polymethylhydrosiloxane (PMHS) as a substituted silane comprising a donor hydrogen atom;
(v) t-BuOD as an alcohol comprising a donor deuterium atom; and
(vi) THF as a solvent;
wherein the reaction mixture is reacted under conditions such that the alkyne functionality of the substrate compound is reductively deuterated to provide the deuterated compound.
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 5 is rejected under 35 U.S.C. 103 as being unpatentable over Guo (Guo, S. et al. “Enantioselective Synthesis of β-Amino Acid Derivatives Enabled by Ligand-Controlled Reversal of Hydrocupration Regiochemistry” Angew. Chem. Int. Ed. 2020, 59, 20841–20845, doi.org/10.1002/anie.202007005; cited in 11/15/2024) in view of Molport (“Tetrahydrofuran-3-acrylic acid methyl ester” Deposit and Available date 03-20-2015).
The teachings of Guo have been set forth above.
Regarding claim 5, Guo fails to teach or suggest that the starting substrate comprises an optionally substituted heterocycle moiety selected from piperidine, piperazine, oxirane, tetrahydrofuran, pyrrolidine, and the heterocycle moiety optionally is substituted with alkyl, alkoxy, carboxyl, carboxy alkyl ester, phenyl, phenoxy, halogen, nitro, sulfonamide, or tosyl.
However, in the same field of endeavor, Molport teaches tetrahydrofuran-3-acrylic acid methyl ester that has been commercially available before the filing date of the instant invention. Tetrahydrofuran-3-acrylic acid methyl ester comprises an alkene and a tetrahydrofuran ring substituted by a carboxyl group:
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Thus, substituting the starting substrates of Guo,
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, with tetrahydrofuran-3-acrylic acid methyl ester of Molport and subjecting the ester into the reaction process of Guo would yield nothing more than the predictable reductive deuteration of the alkene functionality of tetrahydrofuran-3-acrylic acid methyl ester.
It would thus have been prima facie obvious to a skilled artisan before the effective filing date of the instant invention to conduct a method for preparing a deuterated compound, the method comprising reacting a reaction mixture comprising:
(i) a substrate compound comprising an alkyne functionality or an alkene functionality;
(ii) a transition metal catalyst;
(iii) a phosphine ligand for the transition metal catalyst;
(iv) a substituted silane comprising a donor hydrogen atom or a donor deuterium atom;
(v) an alcohol comprising a donor hydrogen atom or a donor deuterium atom; and
(vi) a solvent;
wherein the reaction mixture is reacted under conditions such that the alkyne functionality or the alkene functionality of the substrate compound is reductively deuterated to provide the deuterated compound; and wherein the substrate comprises an optionally substituted heterocycle moiety selected from piperidine, piperazine, oxirane, tetrahydrofuran, pyrrolidine, and the heterocycle moiety optionally is substituted with alkyl, alkoxy, carboxyl, carboxy alkyl ester, phenyl, phenoxy, halogen, nitro, sulfonamide, or tosyl in view of the combination of Guo and Molport.
Conclusion
Claims 1-8, 13 and 15-16 are rejected and no claims are allowed.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to MEDHANIT W BAHTA whose telephone number is (571)270-7658. The examiner can normally be reached Monday-Friday 8am-5pm.
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/MEDHANIT W BAHTA/ Primary Examiner, Art Unit 1692
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