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 .
Priority
This application, filed 2 October, 2023, is a CON of the national stage application of PCT/US2022/022997, filed 1 April, 2022, which claims benefit of the prior application PRO 63/170,422, filed 2 April, 2021.
Information Disclosure Statement
The information disclosure statement (IDS) submitted on 1 September, 2026 is acknowledged and has been considered.
Status of the Application
Receipt is acknowledged of Applicant's claimed invention, filed 1 September, 2026, in the matter of Application N° 18/479,596. Said documents have been entered on the record.
Claim 71 is new. No new matter was introduced.
Therefore, Claims 1, 5, 7, 9, 11, 13, 15, 17-21, 24, 32, 36, 40, 43, 47, 51-52 and 71 are pending.
Election/Restrictions
Applicant’s election without traverse of Group I (Claims 1, 5, 7, 9, 11, 13, 15 and 17-21) in the reply filed on 13 April, 2026 is acknowledged.
Claims 24, 32, 36, 40, 43, 47, 51-52, and Claim 71, are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected inventions, there being no allowable generic or linking claim. Election was made without traverse in the reply filed on 13 April, 2026.
The new Claim 71 is directed to nonelected subject matter and has not been examined on the merits. Claim 71, newly presented in the instant amendment, recites subject matter corresponding to previously presented Claim 43, which was withdrawn from consideration as being directed to a nonelected invention. Although Applicant has amended the dependency of the subject matter such that new Claim 71 now depends from elected Claim 1 rather than Claim 23, changing the claim dependency does not alter the substantive subject matter recited by the claim or bring the previously nonelected subject matter within the scope of the elected invention. Accordingly, Claim 71 remains withdrawn from consideration as directed to the previously nonelected invention. It is further noted that, even if Claim 71 were considered for examination, the recitation of “the protected hydrazone compound of Formula l” would lack antecedent bases, as Formula l is not recited or otherwise introduced in Claim 1, from which Claim 71 depends.
Thus, Claims 1, 5, 7, 9, 11, 13, 15 and 17-21 represent all claims currently under consideration.
Response to Arguments/Amendment
Applicant’s arguments regarding improved yield have been fully considered but are not persuasive (Remarks, Pg 15-16). Applicant compares the yield obtained in an exemplified embodiment of the instant disclosure with yields calculated from a multistep synthesis disclosed by Patel. However, Applicant attributes at least a portion of the asserted improvement to differences in upstream processing, including resolution of a racemic mixture and additional reaction steps used in Patel to prepare the starting material. Claim 1 does not recite these upstream processing steps or otherwise require the manner by which the recited starting materials are prepared. Accordingly, the asserted overall-process yield comparison does not establish that the subject matter actually recited in Claim 1 produces an unexpected result over Patel. Applicant’s arguments therefore do not overcome the rejection which is therefore maintained.
Claim Rejections - 35 USC § 103 (MAINTAINED)
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.
Claims 1, 5, 7, 9, 11, 13, 15 and 17-21 are rejected under 35 U.S.C. 103 as being unpatentable over Patel et al. (WO 2019012063 A1, cited in IDS), hereinafter Patel.
Reference shares an Assignee with the instant Application.
Regarding Claim 1, Patel teaches methods for preparing the bicyclic ketone compounds via a sequence that includes formation of an N-amino lactam intermediate, reaction of that intermediate with an activated carbonyl species, and subsequent cyclization to form a fused heterocyclic system (‘063, Pg. 37, Scheme 3). Specifically, Patel teaches generating an N-amino lactam and reacting it with a carbonate-derived electrophile, followed by activation (e.g., POCl3) to promote condensation and cyclization to a triazole-containing bicyclic product. Patel further teaches the introduction of substituents via organometallic addition to carbonyl-containing intermediates demonstrating the use of conventional carbon-carbon bond-forming techniques in the same synthetic context.
While the instant claim recites reacting the N-amino lactam with a pre-formed “imidate” (e.g., instant Formula c), Patel teaches the use of functionally equivalent activated carbonyl intermediates generated in situ, which perform the same electrophilic role in condensation and heterocycle formation. The difference between employing a pre-formed imidate and generating an activated carbonyl intermediate in situ represents a predictable variation in how the reactive electrophile species is introduced.
In the absence of any evidence of unexpected results or criticality associated with the use of a pre-formed imidate, such a substitution would have been a matter of routine optimization within the level of ordinary skill in the art.
Regarding Claims 5, 7, and 9, Patel teaches the use of acid-mediated and activating conditions, including trifluoroacetic acid (TFA) in combination with an organic solvent (DCE) (‘063, Pg. 37, Scheme 3), as well as additional activating reagents such as POCl3 to promote condensation and cyclization reactions, thereby rendering obvious the recited use of an acid additive and reaction medium. Patel further demonstrates the routine use of a variety of organic solvents across its examples (‘063, Pg. 38-40), indicating that selection of a particular solvent, including alcohol solvents, would have been a matter of routine optimization.
Regarding Claim 11, Patel teaches the same class of intermediates, including an N-amino lactam intermediate that undergoes condensation and cyclization to form the bicyclic heterocycle (‘063, Pg. 37, Scheme 3).
Regarding Claim 13, Patel further demonstrates the use of nitrogen functional group manipulation, including protection and deprotection strategies, in later steps of the synthesis (‘063, Pg. 69, Steps 8-9), reflecting routine control of amine reactivity. Accordingly, the use of an amine protecting group on the N-amino lactam intermediate represents a predictable and routine modification within the ordinary skill in the art.
Regarding Claim 15, Patel teaches the use of organometallic reagents to introduce substituents via carbon-carbon bond formation through nucleophilic addition to carbonyl-containing intermediates (‘063, Pg. 37, Scheme 3). Such transformation is characteristic of Grignard-type reagents (R-MgBr), which perform the same function of installing an R Group at a carbonyl center. Accordingly, the recited use of R1-MgBr represents either the same or an equivalent organometallic addition step as taught by Patel.
Regarding Claims 17-18, Patel teaches Compound Examples 1 & 2:
PNG
media_image1.png
185
334
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Greyscale
(‘063, Pg. 38, Method 1).
Regarding Claims 19-21, Patel teaches Compound Examples 3 & 4:
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183
329
media_image2.png
Greyscale
(‘063, Pg. 39, Method 2).
Patel teaches a synthetic route to bicyclic heterocyclic ketone compounds involving formation of an N-amino lactam intermediate, reaction with an activated carbonyl species, cyclization, and subsequent modification. In performing such multistep syntheses, it is routine to vary the form of activated intermediates, employ protecting groups, select appropriate solvents and acid additives, and use standard carbon-carbon bond-forming reagents to control reactivity and access desired products. Patel demonstrates such flexibility in reagents, substituents, and conditions. One of ordinary skill in the art would therefore have been motivated to apply these routine modifications to the disclosed process, with a reasonable expectation of success in producing the same class of compounds taught by Patel. These variations do not change the fundamental reaction pathway or the nature of the intermediate, but instead reflect alternative implementations of the same synthetic strategy. Therefore, the resulting method would have been prima facie obvious.
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.
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/D.M.N./ Examiner, Art Unit 1627
/SARAH PIHONAK/ Primary Examiner, Art Unit 1627
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