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 .
Election/Restrictions
Applicant’s election without traverse of Group I, drawn to a crystalline form III of a compound of formula 1, a pharmaceutically acceptable thereof of a solvate thereof in the reply filed on December 5, 2025 is acknowledged.
Applicant’s election of monohydrate of N-((3S,5S)-1-((3S,4R)-1-(tert-butyl)-4-(4-chlorophenyl) pyrrolidine-3-carbonyl) pyrrolidine-3-yl)-N-((1s,4R)-4-methylcyclohexyl) isobutyramide hydrochloride as the species of crystalline form III of a compound of formula 1, a pharmaceutically acceptable thereof of a solvate thereof in the reply filed on December 5, 2025 is acknowledged. While applicant elects the species with traverse, applicant did not distinctly and specifically point out the supposed errors in the restriction requirement; therefore, the election has been treated as an election without traverse (MPEP § 818.01(a)).
Claims 6-10, 12-15, 17-20, and 23-24 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention and species, there being no allowable generic or linking claim. Election was made without traverse in the reply filed on December 5, 2025.
Please note applicant indicated the elected species of crystalline form III of a compound of formula 1, a pharmaceutically acceptable thereof of a solvate thereof reads on claims 1-5 and 14-24; However, the examiner determined that claims 14-15, 17-20, and 23-24 are drawn to a non-elected species of crystalline form III.
Expansion of Election of Species Requirement
A reasonable and comprehensive search of the elected species conducted by the Examiner determined that the prior art at the time of the present invention was such that it did not anticipate or render obvious the elected species of crystalline form III of a compound of formula 1. In light of this discovery, the search is expanded to the subject matter of the subgenus of the elected species, i.e., N-((3S,5S)-1-((3S,4R)-1-(tert-butyl)-4-(4-chlorophenyl) pyrrolidine-3-carbonyl) pyrrolidine-3-yl)-N-((1s,4R)-4-methylcyclohexyl) isobutyramide hydrochloride.
Status of Claims
Claims 1-24 are pending. Claims 6-10, 12-15, 17-20, and 23-24 are withdrawn.
Claims 1-5, 11, 16 and 21-22 are under examination in accordance with the elected species along with the expanded species sets forth in the Expansion of Election of Species Requirement section above.
Priority
The instant application 18/251,129 filed on April 28, 2023 is a 371 of PCT/KR2021/015473 filed
on October 29, 2021, which claims priority to, and the benefits of Foreign Application No.
KR10-2020-0142398 filed on October 29, 2020.
Should applicant desire to obtain the benefit of foreign priority under 35 U.S.C. 119(a)-(d) prior to declaration of an interference, a certified English translation of the foreign application must be submitted in reply to this action. 37 CFR 41.154(b) and 41.202(e).
Failure to provide a certified translation may result in no benefit being accorded for the non-English application.
Accordingly, the claims are not entitled to the benefit of the foreign application written in foreign language and will receive an effective filing date of October 29, 2021, which is the filing date of 371 of PCT/KR2021/015473.
Information Disclosure Statement
The information disclosure statement (IDS) submitted on 4/28/2023, 2/20/2024 and 12/5/2025 are in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statements are being considered by the examiner.
Please note that foreign references without an English translation but have an English
translation of the abstract will only have the abstract considered by the Examiner.
Please note the IDS filed on 12/5/2025 has been submitted twice with identical references cited therein; therefore, one out of these two identical IDS has been crossed out.
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 1-5, 11, 16 and 21-22 are 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.
Instant claim 1 recites “[a] crystalline form III of a compound of the following formula 1, a pharmaceutically acceptable salt thereof, or a solvate thereof, wherein the X-ray powder diffraction pattern has 3 or more characteristic peaks selected
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,
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”. However, the instant specification only describes one species of crystalline form III, a hydrate of N-((3S,5S)-1-((3S,4R)-1-(tert-butyl)-4-(4-chlorophenyl) pyrrolidine-3-carbonyl)-5-(morpholine-4-carbonyl) pyrrolidin-3-yl)-N-((1s,4R)-4-methylcyclohexyl) isobutyramide hydrochloride having the structure of:
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(see e.g., Example 1). Please note said compound is a compound of Formula I, wherein R1 is an isopropyl. The specification further describes the powder XRD diffraction pattern peaks of said compound in Table 1 and Fig. 4.
The specification does not disclose other species of crystalline form III of a compound of the Formula 1, a pharmaceutically acceptable salt thereof, or a solvate thereof having 3 or more claimed characteristic peaks in the X-ray diffraction pattern. There is also no disclosure for other species of Formula 1 with other solvate and pharmaceutically acceptable salt therof, wherein R1 is any claimed group other than isopropyl, having 3 or more claimed characteristic peaks in the X-ray diffraction pattern.
Regarding the requirement for adequate written description of chemical entities, Applicant's attention is directed to the MPEP §2163. In particular, Regents of the University of California v. Eli Lilly & Co., 119 F.3d 1559, 1568 (Fed. Cir. 1997), cert. denied, 523 U.S. 1089, 118 S. Ct. 1548 (1998), holds that an adequate written description requires a precise definition, such as by structure, formula, chemical name, or physical properties, "not a mere wish or plain for obtaining the claimed chemical invention." Eli Lilly, 119 F.3d at 1566. The Federal Circuit has adopted the standard set forth in the Patent and Trademark Office ("PTO") Guidelines for Examination of Patent Applications under the 35 U.S.C. 112.I "Written Description" Requirement ("Guidelines"), 66 Fed. Reg. 1099 (Jan. 5,2001), which state that the written description requirement can be met by "showing that an invention is complete by disclosure of sufficiently detailed, relevant identifying characteristics," including, inter alia, "functional characteristics when coupled with a known or disclosed correlation between function and structure ..." Enzo Biochem, Inc. v. Gen-Probe Inc., 296 F.3d 316, 1324-25 (Fed. Cir. 2002) (quoting Guidelines, 66 Fed. Reg. at 1106 (emphasis added)). Moreover, although Eli Lilly and Enzo were decided within the factual context of DNA sequences, this does not preclude extending the reasoning of those cases to chemical structures in general. Univ. of Rochester v G.D. Searle & Co., 249 Supp. 2d 216, 225 (W.D.N.Y. 2003).
To provide adequate written description and evidence of possession of a claimed genus, the specification must provide sufficient distinguishing identifying characteristics of the genus. The factors to be considered include disclosure of complete or partial structure, physical and/or chemical properties, functional characteristics, structure/function correlation, methods of making the claimed product, or any combination thereof.
In the present case, the specification only describes one crystalline form species of Formula 1, specifically, the specification describes a crystalline form III in Example 1 with an X-ray powder diffraction pattern described in Table 1 and Fig. 4. However, the instant claims pertain to the full scope of “a crystalline form III of a compound of the…formula 1, a pharmaceutically acceptable salt thereof, or a solvate thereof” having 3 or more characteristic peaks at the claimed diffraction angles in the X-ray powder diffraction pattern. To the extent that said crystalline form has 3 claimed characteristics peaks in the X-ray powder diffraction pattern, it is insufficient to identify a specific crystalline species. A complete pattern containing at least four strongest reflections (major peaks) is often required to reveal the crystal's unique fingerprint. Weak reflections (minor peaks) cannot be used for crystalline phase or polymorphism identification, as they are often indistinguishable from background noise. Therefore, in order to sufficiently identify a specific crystal structure of a compound, at least four major peak positions are required to determine arrangements of all atoms within its unit cell, including lattice parameters, crystal system, and space group. In addition, the instant specification describes the hydrochloride salt of the compound of Formula 1 (N-((3S,5S)-1-((3S,4R)-1-(tert-butyl)-4-(4-10 chlorophenyl)pyrrolidine-3-carbonyl)-5-(morpholine-4-carbonyl)pyrrolidin-3-yl)-N-((1s,4R)-4-methylcyclohexyl)isobutyramide hydrochloride; see preparation Example 4) is an amorphous compound (see paragraph [00138] of the specification); and when said compound is dissolved in EtOAc at room temperature, it does not give the same crystal in Example 1 (see e.g., [00144]). In other words, the specification does not describe any other hydrochloride salt species of crystalline form III of the compound of the formula I, or a solvate thereof would have the same 3 or more characteristics peaks selected from the list instantly claimed.
in the absence of a sufficient recitation of a representative number of species for the claimed genus, while applicant is in possession of crystalline form III, a hydrate of N-((3S,5S)-1-((3S,4R)-1-(tert-butyl)-4-(4-chlorophenyl)pyrrolidine-3-carbonyl)-5-(morpholine-4-carbonyl)pyrrolidin-3-yl)-N-((1s,4R)-4-methylcyclohexyl)isobutyramide hydrochloride, with an X-ray powder diffraction pattern as shown in Fig. 4 and Table 1, it is not apparent that Applicant was actually in possession of the full scope of the crystalline form III of a compound of Formula 1, a pharmaceutically acceptable solvate or hydrate thereof, having at least 3 claimed characteristics peaks in the X-ray powder diffraction pattern based on the limited disclosure at the time the application was filed.
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.
(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 1-2, 11, 16, and 21-22 are rejected under 35 U.S.C. 102(a)(1) and 102(a)(2) as being anticipated by Kang et al. (WO 2021/091283 A1; cited in the IDS filed on April 28, 2023), as evidenced by Anderson (Academic Press, 2012: pp. 329-364)
Kang et al. teaches a compound of Example 1, N-((3S,5S)-1-((3S,4R)-1-(tert-butyl)-4-(4-chlorophenyl)pyrrolidine-3-carbonyl)pyrrolidine-3-yl)-N-((1s,4R)-4-methylcyclohexyl)isobutyramide hydrochloride, having the structure of:
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is an exemplary compound of Formula I (see e.g., [155]-[156]). Kang et al. further teaches said compound of Example 1 was obtained as a crude solid when purified by trituration using hexane and diethyl ether (see e.g., [173]). Kang et al. further teaches a pharmaceutical composition comprising the compound of Formula 1, or a pharmaceutically acceptable salt or isomer thereof as an active ingredient, together with a pharmaceutically acceptable carrier, wherein the compound is selected from: N-((3S,5S)-1-((3S,4R)-1-(tert-butyl)-4-(4-chlorophenyl)pyrrolidine-3-carbonyl)pyrrolidine-3-yl)-N-((1s,4R)-4-methylcyclohexyl)isobutyramide (see e.g., [69]; claims 4, 6-7).
In the present case, Kang et al. is silent regarding the limitation of “the X-ray powder diffraction pattern has 3 or more characteristic peaks selected from among peaks with the following diffraction angles (2θ values) of: 17.37±0.2°…, 24.66±0.2°, 25.52±0.2°”; However, the claimed characteristics would necessarily present in the compound of Example 1 of Kang et al. since said compound is a crude solid, and a hydrochloride salt of N-((3S,5S)-1-((3S,4R)-1-(tert-butyl)-4-(4-chlorophenyl)pyrrolidine-3-carbonyl)pyrrolidine-3-yl)-N-((1s,4R)-4-methylcyclohexyl)isobutyramide form in reactive crystallization. Please note the hydrochloride salt of N-((3S,5S)-1-((3S,4R)-1-(tert-butyl)-4-(4-chlorophenyl)pyrrolidine-3-carbonyl)pyrrolidine-3-yl)-N-((1s,4R)-4-methylcyclohexyl)isobutyramide taught by Kang et al. is a crystalline form, because salt formation is commonly mentioned as reactive crystallization and the product crystallizes as it is formed, as evidenced by Anderson (see e.g., page 340, “VI. reactive crystallization”). In other words, said hydrochloride salt is a crystalline that would necessarily have the claimed characteristic peaks, for instance, characteristic peaks at 6.62±0.2°, 17.37±0.2°, and 25.52±0.2; therefore, the pharmaceutical composition taught by Kang et al. also anticipates the claimed invention.
Please note that the Patent and Trademark Office is not equipped to conduct experimentation in order to determine whether Applicant’s claimed crystalline is different and, if so, to what extent, from that of the discussed reference.
Therefore, the claimed invention is being anticipated by Kang et al.
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 1-5, 11, 16, and 21-22 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-5 and 11 of copending Application No. 18/251,111; over claims 1-5 and 11 of copending Application No. 18/251,101; over claims 1-5 and 11 of copending Application No. 18/251,084; over claims 1-4 and 14-16 of copending Application No. 18/258,711; over claims 1-4, 11 and 14-16 of copending Application No. 18/258,717; over claims 1-4 and 13-19 of copending Application No. 18/258,730; over claims 1-4 and 9 of copending Application No. 18/558,142; over claims 1-4 and 12 of copending Application No. 18/558,148; over claims 1-3 and 12 of copending Application No. 18/558,351; over claims 1-5 and 17-18 of copending Application No. 18/557,866.
Although the claims at issue are not identical, they are not patentably distinct from each other because the instant claims are anticipated by the claims of the reference applications.
Each of the claims of the abovementioned reference application is drawn to a crystalline form of a compound of the claimed formula 1, a pharmaceutically acceptable salt thereof, or a solvate thereof. Each of the reference claims recite at least 3 characteristics peaks in the X-ray powder diffraction pattern that overlap or lie inside the ranges instantly claimed. For instance, claim 1 of copending Application No. 18/251,111 is drawn to a crystalline form IV of a compound of the following formula 1, a pharmaceutically acceptable salt thereof, or a solvate thereof,
“
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”, in which the compound of formula 1 is N-((3S,5S)-1-((3S,4R)-1-(tert-butyl)-4-(4-chlorophenyl)pyrrolidine-3-carbonyl)pyrrolidine-3-yl)-N-((1s,4R)-4-methylcyclohexyl)isobutyramide. It is noted that the crystalline form of the reference application contains at least 3 characteristics peaks that overlap or lie inside the ranges instantly claimed, for instance, the characteristics peaks at
9.69
±
0.2
°
(overlaps with the characteristic peak recites in the instant claim, 9.89±0.2°), 10.63 ± 0.2° (overlaps with the characteristic peak recites in the instant claim, 10.83 ± 0.2°), and 12.72 ± 0.2° (overlaps with the characteristic peak recites in the instant claim, 12.92 ± 0.2°) of the reference application overlaps with the peaks of instant application. The same is true for each of the above mentioned reference application. In addition, the claims of each of the reference applications are also drawn to a pharmaceutical composition comprising the crystalline form and a pharmaceutically acceptable carrier.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Claims 1-5, 11, 16, and 21-22 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 6-7 of copending Application No. 18/258,705 (reference application).
Although the claims at issue are not identical, they are not patentably distinct from each other because the claims of the reference application is drawn to a method that comprises a crystalline form of the compound of formula 1:
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having an X-ray powder diffraction pattern having 3 or more characteristics peaks selected from among peaks with the
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. It is noted that the crystalline form of the reference application contains at least 3 characteristics peaks that overlap or lie inside the ranges instantly claimed, for instance, the characteristics peaks at 12.841±0.2° (overlaps with the characteristic peak recites in the instant claim, 12.92±0.2°), 10.5969 ± 0.2° (overlaps with the characteristic peak recites in the instant claim, 10.83 ± 0.2°), and 12.841 ± 0.2° (overlaps with the characteristic peak recites in the instant claim, 12.92 ± 0.2°) of the reference application overlaps with the peaks of instant application. The claims of the reference application also pertains to a pharmaceutical composition comprising the amorphous compound of formula I and a pharmaceutically acceptable carrier, in which said amorphous compound comprises the crystalline form; and therefore, the pharmaceutical composition comprises the crystalline compound instantly claimed.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Claims 1-2, 11, 16, and 21-22 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1, 5, 8-10, 13-17 of U.S. Patent No. 12,516,047 B2 (reference patent), as evidenced by Anderson (Academic Press, 2012: pp. 329-364).
Although the claims at issue are not identical, they are not patentably distinct from each other because the claims of the reference patent is drawn to a compound of Formula I, or a pharmaceutically acceptable salt thereof, wherein the compound is selected from N-((3S,5S)-1-((3S,4R)-1-(tert-butyl)-4-(4-chlorophenyl)pyrrolidine-3-carbonyl)pyrrolidine-3-yl)-N-((1s,4R)-4-methylcyclohexyl)isobutyramide and the pharmaceutically acceptable salt is the hydrochloric acid salt. The claims of the reference patent is also drawn to a pharmaceutical composition comprising said compound and a pharmaceutically acceptable carrier.
In the present case, the reference patent is silent regarding the limitation of “the X-ray powder diffraction pattern has 3 or more characteristic peaks selected from among peaks with the following diffraction angles (2θ values) of: 17.37±0.2°…, 24.66±0.2°, 25.52±0.2°”; However, the claimed characteristics would necessarily present in the hydrochloric acid salt of compound of Formula I (N-((3S,5S)-1-((3S,4R)-1-(tert-butyl)-4-(4-chlorophenyl)pyrrolidine-3-carbonyl)pyrrolidine-3-yl)-N-((1s,4R)-4-methylcyclohexyl)isobutyramide) of the reference patent. Please note the hydrochloride salt of N-((3S,5S)-1-((3S,4R)-1-(tert-butyl)-4-(4-chlorophenyl)pyrrolidine-3-carbonyl)pyrrolidine-3-yl)-N-((1s,4R)-4-methylcyclohexyl)isobutyramide taught by the reference patent is a crystalline form, because salt formation is commonly mentioned as reactive crystallization and the product crystallizes as it is formed, as evidenced by Anderson (see e.g., page 340, “VI. reactive crystallization”). In other words, said hydrochloride salt is a crystalline that would necessarily have the claimed characteristic peaks, for instance, characteristic peaks at 6.62±0.2°, 17.37±0.2°, and 25.52±0.2; therefore, the pharmaceutical composition taught by Kang et al. also anticipates the claimed invention.
Please note that the Patent and Trademark Office is not equipped to conduct experimentation in order to determine whether Applicant’s claimed crystalline is different and, if so, to what extent, from that of the discussed reference.
Conclusion
No claims are allowed.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Chihyi Lee whose telephone number is (571)270-0663. The examiner can normally be reached Monday - Friday 8:30 am - 5:00 pm EST.
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/CHIHYI LEE/Examiner, Art Unit 1628 /JEAN P CORNET/Primary Examiner, Art Unit 1628