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 claims the benefit of U.S. Provisional Patent Application No. 63/088,848, filed October 7, 2020, and U.S. Provisional Patent Application No. 63/162,278, filed March 17, 2021.
Information Disclosure Statement
The Information Disclosure Statement filed 04/02/2026 has been considered by the Examiner. The submissions is in compliance with the provisions of 37 CFR §§ 1.97 and 1.98. Enclosed with this Office Action is a return-copy of the Forms PTO-1449 with the Examiner’s signature and indication of those references that have been considered.
Withdrawn Rejections
Claim 1 was provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1, 11 and 12 of Appl. No. 18/987,607 (U.S. PG-PUB 2025/0122197) in view of Chenard et al. (US 6,323,208 B1). The rejection is hereby withdrawn due to the expressed abandonment submitted for the application for U.S. PG-PUB 2025/0122197 filed on 03/20/2026.
Double Patenting
Rejections maintained
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.
A. Claim 1 is rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1, 15, 16, 19, 21 and 22 of U.S. Patent No. 12,441,729 in view of Chenard et al. (US 6,323,208 B1).
Claimed invention
Claim 1 is drawn to a process of preparing a compound of Formula (5M)
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comprising
mixing compound of Formula 4
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with a chiral acid, and
crystallizing the mixture of Formula (4) and the chiral acid to provide a cocrystal compound of Formula (5M) and the chiral acid.
Patent/Reference claims
The patent claims teach a process of preparing Compound A
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(A) and using it to make Compound F
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(F), a pharmaceutically acceptable salt, atropisomer, or a pharmaceutically acceptable salt of an atropisomer thereof.
While the patent claims teach that atropisomer forms of Compound F
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can be made from Compound A
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, the patent claims do not teach mixing Compound A with a chiral acid and crystallizing the mixture of Compound A and the chiral acid to provide a cocrystal compound of Compound A and the chiral acid.
However, the process of forming cocrystals by mixing a chiral acid such as tartaric acid with another compound in order to resolve atropisomers of the compounds was already known. For example, racemic mixtures of atropisomers that contain an acidic or basic moiety, chiral resolution may be achieved by forming diastereomeric salts with optically pure acids (for example, tartaric acid) when the racemate contains a basic moiety or with optically pure bases (for example a-methylbenzyl amine) when the racemate contains an acidic moiety. Repeated recrystallizations of these diastereomeric salts will allow the single pure atropisomer to be obtained. The single pure atropisomer can be used directly as a salt or may be neutralized to obtain the free base or free acid atropisomer. See Chenard, col. 13, third paragraph.
A person of ordinary skill in the art (POSA) would have found it obvious to mix a chiral acid such as tartaric acid with Compound A
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with repeated recrystallization to form the diastereomeric salt with an optically pure acid such as tartaric acid to form a cocrystal containing the salt and an atropisomer of Compound A including the M-atropisomer such as
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because
the patent claims teach that the final compound, Compound F can be made in the form of an atropisomer or a pharmaceutically acceptable salt of an atropisomer, and
Chenard teaches that, in atropisomers that contain a basic moiety, chiral resolution may be achieved by forming diastereomeric salts with optically pure acids such as tartaric acid; and repeated recrystallizations of these salts allow the single pure atropisomer to be obtained. Chenard also teaches single pure atropisomer can be used directly as a salt or may be neutralized to obtain the free base or free acid atropisomer.
The POSA would have had a reasonable expectation of success with preparing a cocrystal of a pharmaceutically acceptable salt of an atropisomer of Compound A and tartaric acid because Compound A has a basic moiety due to the presence of nitrogen in the ring and tartaric acid can be used for chiral resolution of atropisomers with a basic moiety to form cocrystals containing the atropisomer and salt.
Therefore, the claimed invention as a whole would have been prima facie obvious at the time the invention application was filed.
Response to arguments
Applicant's arguments have been fully considered but have not been found to be persuasive.
Regarding Applicant’s argument that the patent is not a proper reference for purposes of nonstatutory obvious-type double patenting in view of Ex parte Baurin, the application of NSDP is not precluded solely by comparing filing dates or projected expiration dates of the patents. Rather, the relevant inquiry is whether the claims of the instant application are patentably distinct from the claims of the commonly owned reference patent such that both patents if issued would extend the exclusivity period for the same or obvious variants of the invention. While Applicant cites Ex parte Baurin, the decision is fact-specific and does not establish a general rule precluding use of such references. In this case, Applicant has not established that the cited patent cannot give rise to an unjustified extension of patent term for patentably indistinct subject matter.
Regarding Applicant’s argument that the patent is not a proper reference for purposes of nonstatutory obvious-type double patenting in view of Ex parte Baurin, the application of NSDP is not precluded solely by comparing filing dates or projected expiration dates of the patents. Rather, the relevant inquiry is whether the claims of the instant application are patentably distinct from the claims of the commonly owned reference patent such that both patents if issued would extend the exclusivity period for the same or obvious variants of the invention. While Applicant cites Ex parte Baurin, the decision is fact-specific and does not establish a general rule precluding use of such references. In this case, Applicant has not established that the cited patent cannot give rise to an unjustified extension of patent term for patentably indistinct subject matter.
Applicant argues that Chenard does not expressly disclose a “cocrystal” and that the cited patent claims do not themselves recite crystallizing the mixture to provide a cocrystal of the compound and the chiral acid. However, the rejection does not rely on the patent claims alone, nor require Chenard to disclose the identical claimed process verbatim. The instant invention claims a process for using Formula 4
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to make its specific atropisomer labeled Formula (5M)
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. The reference patent teaches the relevant compound of Formula A (same as instant Compound 4) can be provided in its atropisomeric form. Chenard teaches that racemic mixtures of atropisomers containing acidic or basic moieties may be resolved by mixing with optically pure such as tartaric acid and repeated recrystallization and isolating a single pure atropisomer. Thus, Chenard provides the teaching of chiral-acid resolution and recrystallization and forming a desired atropisomer. Given that Compound 4/Compound A contains basic nitrogen moiety and the patent claims already teach atropisomeric forms thereof, the POSA would have had a reasonable expectation of success in applying Chenard’s known chiral-acid recrystallization technique to obtain the claimed atropisomer/chiral-acid crystalline form on the way to forming the claimed feature atropisomer of compound of Formula (5M). Therefore, the fact that Chenard does not use the term “cocrystal” is not dispositive of the chiral-acid recrystallization technique.
Applicant asserts that Chenard uses HPLC, not chiral acid. However, Chenard is not limited to HPLC as suggested by Applicant and, indeed, teaches chiral-resolution with optically pure acids.
Applicant further argues that there is no reasonable expectation of success. However, because Compound A/Compound 4 contains a basic nitrogen moiety and the cited patent claims already teach formation of atropisomeric forms, the POSA would have had a reasonable expectation that applying Chenard’s chiral-acid recrystallization technique would produce the claimed Formula (5M) atropisomer.
B. Claim 1 is rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1 and 14-16 of U.S. Patent No. 12,473,281 in view of Chenard et al. (US 6,323,208 B1).
Claimed invention
Claim 1 is drawn to a process of preparing a compound of Formula (5M)
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comprising
mixing compound of Formula 4
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with a chiral acid, and
crystallizing the mixture of Formula (4) and the chiral acid to provide a cocrystal compound of Formula (5M) and the chiral acid.
Patent/Reference claims
The patent claims teach a process that includes mixing Compound 4
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(4) with (+)-DBTA (i.e., a chiral acid) and arriving at Compound (4A)
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(4A) (i.e., a salt containing the atropisomer of Compound 4) and, after additional steps, eventually arriving at Compound (5M),
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(5M) (i.e., the atropisomer of Compound 4).
While the patent claims teach mixing Compound 4 with (+)-DBTA (i.e., a chiral acid) to make Compound (4A) (i.e., a salt containing the atropisomer of Compound 4 and (+)-DBTA) and eventually make Compound (5M),
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(i.e., the atropisomer of Compound 4), the patent claims do not teach crystallizing the mixture to provide a cocrystal compound of Compound 4A and the chiral acid.
However, the process of forming cocrystals by mixing a chiral acid (e.g., tartaric acid) with another compound and recrystallizing the mixture in order to resolve atropisomers of the compounds was already known. For example, racemic mixtures of atropisomers that contain an acidic or basic moiety, chiral resolution may be achieved by forming diastereomeric salts with optically pure acids (for example, tartaric acid) when the racemate contains a basic moiety or with optically pure bases (for example a-methylbenzyl amine) when the racemate contains an acidic moiety. Repeated recrystallizations of these diastereomeric salts will allow the single pure atropisomer to be obtained. The single pure atropisomer can be used directly as a salt or may be neutralized to obtain the free base or free acid atropisomer. See Chenard, col. 13, third paragraph.
A person of ordinary skill in the art (POSA) would have found it obvious to mix a chiral acid such as tartaric acid or (+)-DBTA with Compound 4
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with repeated recrystallization to form the diastereomeric salt with an optically pure acid (e.g., tartaric acid, (+)-DBTA) to form a cocrystal containing the acid and Compound 4A (i.e., atropisomer) because
the patent claims teach Compound 4, which is not an atropisomer, is mixed with (+)-DBTA (i.e., a chiral acid) to make Compound 4A (i.e., an atropisomer salt) that can be used to make Compound 5M (an atropisomer), and
Chenard teaches that, in atropisomers that contain a basic moiety, chiral resolution may be achieved by forming diastereomeric salts with optically pure acids such as a tartaric acid; and repeated recrystallizations of these salts allow the single pure atropisomer to be obtained. Chenard also teaches single pure atropisomer can be used directly as a salt or may be neutralized to obtain the free base or free acid atropisomer.
The POSA would have had a reasonable expectation of success with preparing a cocrystal of a pharmaceutically acceptable salt of Compound 4A and chiral acid (e.g., tartaric acid, (+)-DBTA) because Compound 4 has a basic moiety due to the presence of nitrogen in the ring and the chiral acid - tartaric acid for example - can be used for chiral resolution of atropisomers with a basic moiety to form cocrystals containing the atropisomer and salt.
Therefore, the claimed invention as a whole would have been prima facie obvious at the time the invention application was filed.
Applicant's arguments have been fully considered but have not been found to be persuasive.
Applicant asserts that the ODP rejection over the patent is improper because it has a later filing date and later expiration date. However, the proper inquiry here remains whether the instant claims are patentably distinct from the claims of the cited patent. Applicant further argues the term “cocrystal” is not mentioned by Chenard. However, Chenard teaches mixing the compound with a chiral acid and recrystallizing the resulting mixture to obtain a crystalline form containing the atropisomer and the acid. The cocrystal represents a predictable solid state form as the resultant.
Response to arguments
Applicant’s arguments rely on similar arguments as above. For the same reasons outlined above, Applicant’s arguments are not found to be persuasive.
C. Claim 1 is provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1, and 21-22 of U.S. PG-PUB 2023/0391771 in view of Chenard et al. (US 6,323,208 B1).
NOTE: The reference application for U.S. PG-PUB 2023/0391771 has been allowed. Upon issuance of a patent, this rejection will be made over the issued patent.
Claimed invention
Claim 1 is drawn to a process of preparing a compound of Formula (5M)
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comprising
mixing compound of Formula 4
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with a chiral acid, and
crystallizing the mixture of Formula (4) and the chiral acid to provide a cocrystal compound of Formula (5M) and the chiral acid.
Patent/Reference claims
The patent claims teach a process of preparing a racemized Compound A
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which is resolved using tartrate (chiral acid) to separate it into its respective atropisomers, i.e., (P)-compound A and (M)-compound A (i.e.,
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).
While the patent claims teach that racemized Compound A can be mixed with tartrate to form its (P)- and (M)-atropisomers (e.g.,
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), the patent claims do not teach crystallizing the mixture to provide a cocrystal compound of the (M)-atropisomer and the chiral acid.
However, the process of forming cocrystals by mixing a chiral acid (e.g., tartaric acid) with another compound and recrystallizing the mixture in order to resolve atropisomers of the compounds was already known. For example, racemic mixtures of atropisomers that contain an acidic or basic moiety, chiral resolution may be achieved by forming diastereomeric salts with optically pure acids (for example, tartaric acid) when the racemate contains a basic moiety or with optically pure bases (for example a-methylbenzyl amine) when the racemate contains an acidic moiety. Repeated recrystallizations of these diastereomeric salts will allow the single pure atropisomer to be obtained. The single pure atropisomer can be used directly as a salt or may be neutralized to obtain the free base or free acid atropisomer. See Chenard, col. 13, third paragraph.
A person of ordinary skill in the art (POSA) would have found it obvious to mix a chiral acid such as tartaric acid or (+)-DBTA with Compound 4
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with repeated recrystallization to form the diastereomeric salt with an optically pure acid (e.g., tartaric acid, (+)-DBTA) to form a cocrystal containing the acid and Compound 4A (i.e., atropisomer) because
the patent claims teach Compound 4, which is not an atropisomer, is mixed with (+)-DBTA (i.e., a chiral acid) to make Compound 4A (i.e., an atropisomer salt) that can be used to make Compound 5M (an atropisomer), and
Chenard teaches that, in atropisomers that contain a basic moiety, chiral resolution may be achieved by forming diastereomeric salts with optically pure acids such as a tartaric acid; and repeated recrystallizations of these salts allow the single pure atropisomer to be obtained. Chenard also teaches single pure atropisomer can be used directly as a salt or may be neutralized to obtain the free base or free acid atropisomer.
The POSA would have had a reasonable expectation of success with preparing a cocrystal of a pharmaceutically acceptable salt of Compound 4A and chiral acid (e.g., tartaric acid, (+)-DBTA) because Compound 4 has a basic moiety due to the presence of nitrogen in the ring and the chiral acid - tartaric acid for example - can be used for chiral resolution of atropisomers with a basic moiety to form cocrystals containing the atropisomer and salt.
Therefore, the claimed invention as a whole would have been prima facie obvious at the time the invention application was filed.
This is a provisional rejection.
Response to arguments
Because substantive arguments were not made against this rejection, it is deemed to still be proper and is, therefore, maintained.
Conclusion
No claims are allowed.
THIS ACTION IS MADE FINAL. 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 CHRIS E SIMMONS whose telephone number is (571)272-9065. The examiner can normally be reached M-F: 9:30-6:00p.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, James H. Alstrum-Acevedo can be reached at (571) 272-5548. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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CHRIS E. SIMMONS
Examiner
Art Unit 1622
/CHRIS E SIMMONS/Examiner, Art Unit 1622
/JAMES H ALSTRUM-ACEVEDO/Supervisory Patent Examiner, Art Unit 1622
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