DETAILED ACTION
This office action is in response to applicant’s filing dated July 24, 2026.
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 claims
Claims 1, 3, 6, 8, 12, 17, 21, 23, 26, 38, and 41 are pending in the instant application. Acknowledgment is made of Applicant’s amendments filed July 24, 2026. Acknowledgment is made of Applicant’s cancelation of claims 33, 43, 49, 52, 55, 56, 67, 71, 73, 75 and 78.
Election/Restrictions
Applicant’s election without traverse of Group I, claims 1, 3, 6, 8, 12, 17, 21, 23, 26, 38, and 41, drawn to a process of preparing the compound (R)-11 in the reply filed on July 24, 2026 is acknowledged. Applicant canceled all non-elected claims.
Claims 1, 3, 6, 8, 12, 17, 21, 23, 26, 38, and 41 are under consideration in the present office action.
Priority
The present application is a CON of PCT/CN2022/123711, filed October 5, 2022, and claims the benefits of priority to PCT/CN2021/122508, filed October 6, 2021, PCT/CN2021/122511, filed October 6, 2021 and PCT/CN2021/122512, filed October 6, 2021.
Information Disclosure Statement
The information disclosure statements (IDS) submitted on 08/01/2024, 10/21/2024, 11/20/2024, 01/07/2025, 01/15/2025, 02/07/2025, 03/12/2025, 04/03/2025, 04/08/2025, 05/05/2025, 08/22/2025, 03/20/2026 and 03/25/2026 are in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statements are being considered by the examiner.
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)(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.
Claims 1, 3, 6, 8, 12, 17 and 21 are rejected under 35 U.S.C. 102(a)(2) as being anticipated by Deligny et al (WO 2021/204896 A1, cited in IDS, filed 08/01/2024, hereinafter Deligny).
The applied reference has a common applicant, assignee and/or join inventor with the instant application. Based upon the earlier effectively filed date of the reference, it constitutes prior art under 35 U.S.C. 102(a)(2). This rejection under 35 U.S.C. 102(a)(2) might be overcome by: (1) a showing under 37 CFR 1.130(a) that the subject matter disclosed in the reference was obtained directly or indirectly from the inventor or a joint inventor of this application and is thus not prior art in accordance with 35 U.S.C. 102(b)(2)(A); (2) a showing under 37 CFR 1.130(b) of a prior public disclosure under 35 U.S.C. 102(b)(2)(B) if the same invention is not being claimed; or (3) a statement pursuant to 35 U.S.C. 102(b)(2)(C) establishing that, not later than the effective filing date of the claimed invention, the subject matter disclosed in the reference and the claimed invention were either owned by the same person or subject to an obligation of assignment to the same person or subject to a joint research agreement.
Instant claims are drawn to a drawn to a process of preparing the compound (R)-11:
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, where the step comprises separation of the stereoisomer form racemic mixture of compound 11:
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, and where the process of preparation further comprises the following steps:
Reaction of a salt of compound 10 with a peptide coupling agent to obtain compound 11:
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469
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;
Boc-deprotection to obtain compound 10 from compound 9:
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500
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;
Reaction of compound 8 with 8A to obtain compound 9:
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609
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;
Mesylation of compound 7 affording compound 8:
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126
627
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;
Desylilation of compound 6, affording compound 7:
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91
586
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;
Reaction of compound 5 with compound 5A to obtain compound 6:
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144
610
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.
Deligny teaches a process of preparing the compound 10:
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171
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from the compound 8:
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by Chiral SFC (pages 169 – 170, [0622] and [0623]). The process taught by Deligny further comprises following synthetic steps:
Synthesis of compound 8 from intermediate compound 26:
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170
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, where EDCI is a peptide coupling agent, and intermediate compound 26 is used as a salt, hydrochloride (page 169, [0621]);
Boc-deprotection, affording intermediate compound 26 from intermediate compound 25:
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651
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(page 119, [0510]);
Synthesis of intermediate compound 25 from intermediate compound 8:
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685
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;
Mesylation of intermediate compound 7 to obtain intermediate compound 8:
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156
618
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;
Desylilation of intermediate compound 6, affording intermediate compound 7:
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168
631
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;
Synthesis of intermediate compound 6 from intermediate compound 5:
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614
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(pages 110 – 111, [0491] - [0493]). Although Deligny does not say explicitly that intermediate compound 26 was introduced into the of synthesis of compound 8 in the form of salt, the skilled artisan would understand that since intermediate compound 26 is a product of Boc-deprotection, which reaction is conducted in the presence of HCl, the product is obtained as a salt, hydrochloride, and is used in the next synthetic step (synthesis of compound 8) as is.
Thus, Deligny teaches the same method for synthetic preparation of the same compound.
Therefore, teachings of Deligny anticipate the instantly claimed process.
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.
Claims 1, 23, 26, 38 and 41 are rejected under 35 U.S.C. 103 as being obvious over Deligny et al (WO 2021/204896 A1), as applied above to the claims 1, 3, 6, 8, 12, 17 and 21.
The applied reference has a common applicant, assignee and/or join inventor with the instant application. Based upon the earlier effectively filed date of the reference, it constitutes prior art under 35 U.S.C. 102(a)(2).
Regarding claims 1, 23 and 26, drawn to a process of preparing the compound (R)-11:
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, where the synthetic steps comprise:
Preparing compound 5 from compound 4:
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621
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;
Reaction of compound 3 with compound 3A to afford compound 4:
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.
Deligny teaches a process of preparing the compound 10:
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. Deligny also teaches the reactions:
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; and
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.
Deligny does not teach the reactions shown above on the compounds identical to instantly claimed compounds 4 and 5. However, Deligny teaches the same exact reactions performed on structural analogs, where phenyl ring substituents in the instantly claimed compounds 4 and 5 are merely structural modifications and do not participate in the above reactions.
Thus, since Deligny teaches the process of synthetic preparation of the compound structurally identical to the instantly claimed compound, as well as the process of preparation of structural variants, where the same synthetic steps are performed on the structurally analogous intermediate compounds, it would have been prima facie obvious to one of ordinary skill in the art before the effective filing date of the present invention to modify the known synthetic pathway by employing known alternative steps to arrive at the claimed process with the reasonable expectation of success.
Regarding claims 38 and 41, drawn to a to a process of preparing the compound (R)-11:
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, where the synthetic step comprises the reaction:
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, where the salt of compound (R)-10 reacts with a peptide coupling agent to afford compound (R)-11.
Deligny teaches a process of preparing the compound 10:
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from the compound
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by Chiral SFC (pages 169 – 170, [0622] and [0623]). The process taught by Deligny further comprises following synthetic steps:
- Synthesis of compound 8 from intermediate compound 26:
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170
513
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, where EDCI is a peptide coupling agent, and intermediate compound 26 is used as a salt, hydrochloride, (page 169, [0621]). Although Deligny does not say explicitly that intermediate compound 26 was introduced into the of synthesis of compound 8 in the form of salt, the skilled artisan would understand that since intermediate compound 26 was a product of Boc-deprotection, which reaction is conducted in the presence of HCl, the product is obtained as a salt, hydrochloride, and is used in the next synthetic step (synthesis of compound 8) as is. Although Deligny teaches the process of preparation of compound 10, where the cyclization reaction affords a racemic mixture and followed by separation of enantiomers, and instant claims disclose the cyclization of a single enantiomer (R)-10 to afford a single enantiomer (R)-11, both processes lead to the same final product (R)-11. Changing order of reactions in the multistep synthesis, which leads to the same final product, is the standard laboratory practice. MPEP 2144.04. states: See also In re Burhans, 154 F.2d 690, 69 USPQ 330 (CCPA 1946) (selection of any order of performing process steps is prima facie obvious in the absence of new or unexpected results); In re Gibson, 39 F.2d 975, 5 USPQ 230 (CCPA 1930) (Selection of any order of mixing ingredients is prima facie obvious.).
Thus, since Deligny teaches the same process of synthetic preparation of the structurally identical compound, where some steps are performed in the different order, it would have been prima facie obvious to one of ordinary skill in the art before the effective filing date of the present invention to modify a known process by altering the sequence of synthetic steps and producing the same exact final product with the reasonable expectation of success.
Therefore, taking all together, taught by prior art, the invention as a whole is prima facie obvious to one of ordinary skill in the art at the time the invention was made, as evidenced by the references, especially in the absence of evidence to the contrary.
This rejection under 35 U.S.C. 103 might be overcome by: (1) a showing under 37 CFR 1.130(a) that the subject matter disclosed in the reference was obtained directly or indirectly from the inventor or a joint inventor of this application and is thus not prior art in accordance with 35 U.S.C.102(b)(2)(A); (2) a showing under 37 CFR 1.130(b) of a prior public disclosure under 35 U.S.C. 102(b)(2)(B); or (3) a statement pursuant to 35 U.S.C. 102(b)(2)(C) establishing that, not later than the effective filing date of the claimed invention, the subject matter disclosed and the claimed invention were either owned by the same person or subject to an obligation of assignment to the same person or subject to a joint research agreement. See generally MPEP § 717.02.
Conclusion
Claims 1, 3, 6, 8, 12, 17, 21, 23, 26, 38, and 41 are rejected. No claim is allowed.
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/E.V.V./Examiner, Art Unit 1691
/SAVITHA M RAO/Primary Examiner, Art Unit 1691
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