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 on 12/08/2022, is a U.S. National Stage Application, filed under 35 U.S.C. § 371, of International Application No. PCT/US2021/036693, filed on 06/09/2021, which claims priority of U.S. Provisional Application No. 63/037,478, filed on 06/10/2020 and U.S. Provisional Application No. 63/070,502, filed on 08/26/2020.
Information Disclosure Statement
The information disclosure statement (IDS) filed on 07/11/2023, 06/20/2024, 08/19/2024, and 11/25/2024, complies with the provisions of 37 CFR 1.97, 1.98 and MPEP § 609. Accordingly, it has been placed in the application file and the information therein has been considered as to the merits, except where noted.
Status of claims
The preliminary amendment filed on 12/08/2025, that amended claim 106, and canceled claims 2-3, 6-8, 10-16, 19, 21-25, 27-36, 38-43, 45-46, 48-50, 52-59, 62-68, 70-81, 83-94, 96-99, 101, 103-105, 107-111, is acknowledged. Claims 1, 4-5, 9, 17-18, 20, 26, 37, 44, 47, 51, 60-61, 69, 82, 95, 100, 102, and 106 are pending.
Election/Restriction
Applicant’s response filed on 12/08/2025 to Restriction/Election Requirement filed on 10/10/2025, is acknowledged. Applicant elected without traverse Group I drawn to a compound of formula (II) and a pharmaceutical composition comprising a compound of formula (II). Claims 1, 4-5, 9, 17-18,20,26, 37, 44, 47, 82 and 95 read on the elected Group. Claims 51, 60-61, 69, 100 and 102 of Group II-V are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention, there being no allowable generic or linking claim.
Pursuant to the Election of Species Requirement, Applicant respectively elected without traverse, the compound depicted below for prosecution on the merits to which the claims shall be restricted if no generic claim is finally held to be allowable.
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Claims 1, 9, 26, 37, 44, 82, and 95 read on the elected species. Applicant’s elected species was searched, and determined to be free of the art of record. Pursuant to MPEP § 803.02, the search and examination was extended to the non-elected species discussed below, which new search species falls within the scope of instant claims 1, 9, 26, 37, 44, 82, and 95 (i.e., claims to proper Markush groupings that include both the new search species as well as the originally elected species. MPEP § 803.02(III)(C)(2)). The new search species underlies rejections of these claims pursuant to 35 U.S.C. § 102. As such, the election of species requirement is maintained as provisional, and claims 4-5, 17-18, 20, 47, 51, 60-61, 69, 100, 102, and 106 are provisionally withdrawn from consideration pursuant to 37 CFR 1.142(b). See, MPEP § 803.02.
Claims 1, 4-5, 9, 17-18, 20, 26, 37, 44, 47, 51, 60-61, 69, 82, 95, 100, 102, and 106 are pending with claims 4-5, 17-18, 20, 47, 51, 60-61, 69, 100, 102, and 106 are withdrawn from further consideration, and claims 1, 9, 26, 37, 44, 82, and 95 are under consideration,
Claim interpretation
Examination requires claim terms first be construed in terms in the broadest reasonable manner during prosecution as is reasonably allowed in an effort to establish a clear record of what applicant intends to claim. See MPEP § 2111. Under a broadest reasonable interpretation, words of the claim must be given their plain meaning, unless such meaning is inconsistent with the specification. See MPEP § 2111.01. It is also appropriate to look to how the claim term is used in the prior art, which includes prior art patents, published applications, trade publications, and dictionaries. MPEP § 2111.01 (III). However, specific embodiments of the specification cannot be imported into the claims, particularly where the subject claim limitation is broader than the embodiment. MPEP § 2111.01(II).
Claim 1 recites “… wherein each alkyl, alkoxy, heteroalkyl, cycloalkyl, or heterocycloalkyl is optionally substituted; …. an optionally substituted heterocycloalkyl or cycloalkyl; etc. claims 1, 5, 9, 18, 20, 37, 47, 51, 60, 61, 69 include multiple optionally substituted groups. However, the claims do not recite the substituents.
Instant specification does not define the term “optionally substituted”. The specification only provides general teaching of the substituents. For example, “unless stated otherwise specifically in the specification, an alkyl group is optionally substituted by one or more of the following substituents: halo, cyano, nitro, oxo, thioxo, imino, oximo, trimethylsilanyl, …”. [Pg. 10]. This recitation provides examples of possible substitutes. Therefore, under broadest reasonable interpretation, the term “optionally substituted” is interpreted as optionally substituted with any substituents or groups know to one of ordinary skill in organic chemistry.
Claim Objection
Claim 82 is objected to for the following informalities:
Claim 82 recites “…, R10 and R11 are each hydrogen …”. Then the claim recites “R11 and R12 are taken together with the atoms to which they are attached to form a cyclobutyl ring.” The claim is objected to because if R11 is hydrogen, the underlined recitation is not possible. While the skilled chemist would understand that the claim requires that R11 may be hydrogen or R11 is forming a ring with R12, however, the claim language should be changed to correct the improper recitation.
Appropriate correction is required.
Rejections 35 U.S.C. 112(b)
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.
Claims 1, 9, 26, 37, 44, 82, and 95 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.
Claim 1 recites “… optionally substituted 5- or 6-membered ring (e.g., cycloalkyl or heterocycloalkyl) on numbered page 3 and approximately 11 lines from the bottom of said page of the December 8, 2025 claim set. The recitation of “e.g.” is repeated in claims 9, 20, 51, 60, 61, and 69. The recitation of “e.g.” (for example) render the claim indefinite. As provided in MEMP 2173.05(d), “Description of examples or preferences is properly set forth in the specification rather than the claims. If stated in the claims, examples and preferences may lead to confusion over the intended scope of a claim. In those instances where it is not clear whether the claimed narrower range is a limitation, a rejection under 35 U.S.C. 112(b) or pre-AIA 35 U.S.C. 112, second paragraph should be made. The examiner should analyze whether the metes and bounds of the claim are clearly set forth.
Dependent claims 26, 37, 44, 82, and 95 are indefinite due to their dependence on a rejected claim and lacking any limitations that cure the ambiguities resulting from the parent claim(s).
Claim Rejections - 35 USC § 102
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.
§ 102 Rejection over Bernotas
Claims 1, 9, 37 44, and 95 are rejected under 35 U.S.C. 102(a)(2)/(a)(2) as being anticipated by R. Bernotas et al. (USPN 7585873B2, 09/08/2009, “Bernotas” cited in the PTO-892).
Bernotas discloses a compound for the treatment of disorders relating to the 5-HT6 receptor. Bernotas discloses compound of example 31, [Col. 22, Example 31]:
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Bernotas’s above compound anticipates claim 1 formula (II), wherein:
R2 is H; R3 is H; p is 0; R10 and R11 are H; R12 and R13 are H; R14 and R15 are alkyl, CH3; X7 is N; X4 is CR4 and R4 is H; X5 is CR5 and R5 is H; X6 is CR6 and R6 is H.
Bernotas’s above compound anticipates claim 9 formula (IIC), wherein:
R2 is H; R3 is H; p is 0; R12 and R13 are H; R14 and R15 are alkyl, CH3; X7 is N; X4 is CR4 and R4 is H; X5 is CR5 and R5 is H; X6 is CR6 and R6 is H.
Bernotas’s above compound anticipates claim 37 wherein R14 and R15 are alkyl.
Bernotas’s above compound anticipates claim 44 wherein R1 is -CH2CH2N(CH3)2.
With regard to claim 95, Bernotas teaches a pharmaceutical composition comprising a compound of the invention and a pharmaceutically acceptable carrier. [Col. 14, ln. 13-16].
§ 102 Rejection over Solana
Claims 1, 9, 37, 82, and 95 are rejected under 35 U.S.C. 102(a)(1)/(a)(2) as being anticipated by J. Solana et al. (WO 2018/149986 A1, 08/23/2018, “Solana” cited in the PTO-892).
Solana discloses 2-(5-Bromo-1H-pyrrolo[2,3-c]pyridin-1-yl)-N,N-diethylethanamine, [Pg. 77, ln. 11]:
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Solana’s above compound anticipates claim 1 formula (II), wherein:
R2 is H; R3 is H; p is 0; R10 and R11 are H; R12 and R13 are H; R14 and R15 are alkyl, -CH2CH3; X6 is N; X4 is CR4 and R4 is H; X5 is CR5 and R5 is halo, Br; X7 is CR7 and R7 is H.
Solana’s above compound anticipates claim 9 formula (IIC), wherein:
R2 is H; R3 is H; p is 0; R12 and R13 are H; R14 and R15 are alkyl, -CH2CH3; X6 is N; X4 is CR4 and R4 is H; X5 is CR5 and R5 is halo, Br; X7 is CR7 and R7 is H.
Solana’s above compound anticipates claim 37 wherein R14 and R15 are alkyl.
Solana’s above compound anticipates claim 82 formula (VI), wherein:
R3 is H; R10 and R11 are H; R12 and R13 are H; R14 and R15 are alkyl, -CH2CH3; X6 is N; X4 is CR4 and R4 is H; R5 is halo, Br.
With regard to claim 95, Solana discloses a pharmaceutical composition comprising a compound of any embodiments thereof, e.g., the above compound, and one or more pharmaceutically acceptable carriers. [Pg. 56, ln. 27-30].
§ 102 Rejection over Glushkov
Claims 1, 37, and 44 are rejected under 35 U.S.C. 102(a)(1)/(a)(2) as being anticipated by R. Glushkov et al. (USPN 4088647 A, 05/09/1978, “Glushkov” cited in the PTO-892).
Glushkov discloses indole derivatives, for example, 1-hydroxo-7-methoxy-9-(3-dimethyl aminoethyl)- 1,2,3,4-tetrahydro-g-carboline having the formula (2) [Col. 4, ln. 32-34]:
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Glushkov’s above compound anticipates claim 1 formula (II), wherein:
R2 and R3 are taken together to form heterocycloalkyl ring; p is 0; R10 and R11 are H; R12 and R13 are H; R14 and R15 are alkyl, CH3; X4 is CR4 and R4 is H; X5 is CR5 and R5 is -OCH3; X6 is CR6 and R6 is H; X7 is CR7 and R7 is H.
Bernotas’s above compound anticipates claim 37 wherein R14 and R15 are alkyl.
Bernotas’s above compound anticipates claim 44 wherein R1 is -CH2CH2N(CH3)2.
§ 102 Rejection over Viaud
Claim 1 is rejected under 35 U.S.C. 102(a)(1)/(a)(2) as being anticipated by M. Viaud et al. (USPN 5714495A, 02/03/1998, “Viaud” cited in the PTO-892).
Viaud discloses 1-aminoethyl-[pyrrolo2,3-b) pyridine below:
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Viaud’s above compound anticipates claim 1 formula (II), wherein:
R2 is H; R3 is H; p is 0; R10 and R11 are H; R12 and R13 are H; R14 and R15 are H; X7 is N; X4 is CR4 and R4 is H; X5 is CR5 and R5 is H; X6 is CR6 and R6 is H.
§ 102 Rejection over Azimov
Claim 1 is rejected under 35 U.S.C. 102(a)(1) as being anticipated by Azimov, V. et al. (Khimiya Geterotsiklicheskikh Soedinenii (1976), (6), 848-52 CODEN: KGSSAQ; ISSN: 0132-6244, “Azimov” cited in the PTO-892).
Azimov discloses compound XI below:
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Azimov’s compound XI anticipates claim 1 formula (II), wherein:
R2 is H; R3 is alkyl substituted with OH (CH2OH), see claim interpretation above; p is 0; R10 and R11 are H; R12 and R13 are H; R14 and R15 are CH3; X4 and X7 are N; X5 is CR5 and R5 is H; X6 is CR6 and R6 is H.
§ 102 Rejection over Burger
Claim 1 is rejected under 35 U.S.C. 102(a)(1) as being anticipated by J M. Burger et al. (J. Med. Chem. 2006, 49, 1730-1743, “Burger” cited in the PTO-892).
Burger discloses compound 6h [Pg. 1732, Figure 3], [Burger, supporting information, 6h, Pg. S6, 2nd para.]:
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Burger’s compound 6h anticipates claim 1 formula (II), wherein:
R2 is H; R3 is H; p is 2; R10 and R11 are H; R12 and R13 are H; R14 and R15 are H; X4 is N; X6 is CR6 and X7 is CR7 wherein R6 and R7 are H; X5 is CR5 and R5 is ORa and Ra is CH3.
Note: Claim 1 is anticipated by multiple prior art references. Applicant is advised to review the attached STN search document.
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 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.
Claims 1, 9, 26, 37, and 95 are rejected under 35 U.S.C. 103 as being unpatentable over B. Kenda et al. (US PG PUB 2012/0214815 A1, 08/23/2012, “Kenda” cited on the PTO-892).
Kenda teaches compounds for treating central nervous system disorders including epilepsy, epileptogenesis, seizure disorders, etc. [0012]. Kenda teaches 4-propyl-1-(1H-pyrrolo[3,2-b]pyridin-1-ylmethyl)pyrrolidin-2-one as one of the compounds, [Pg. 119 col. 2, 3rd comp.]:
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Kenda’s above compound reads on claim 1 formula (II), wherein:
R2 is H; R3 is H; p is 0; R10 and R11 are H; X4 is N; X5 is CR5 and R5 is H; X6 is CR6 and R6 is H; X7 is CR7 and R7 are H; R14 and R15 are taken together with the nitrogen atom to form a heterocycloalkyl substituted with alkyl (alkyl meet the definition of the substituent as described in the claim interpretation section above). Kenda’s above compound differs from instantly claimed formula (II) in that Kenda’s compound include one -CH2 whereas formula (II) required at least another -CH2 group.
However, as provided in MPEP 2144.09, a prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities. "An obviousness rejection based on similarity in chemical structure and function entails the motivation of one skilled in the art to make a claimed compound, in the expectation that compounds similar in structure will have similar properties." In re Payne, 606 F.2d 303, 313, 203 USPQ 245, 254 (CCPA 1979). See In re Papesch, 315 F.2d 381, 137 USPQ 43 (CCPA 1963). Compounds which are homologs (compounds differing regularly by the successive addition of the same chemical group, e.g., by -CH2- groups) are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties. In re Wilder, 563 F.2d 457, 195 USPQ 426 (CCPA 1977). See also In re May, 574 F.2d 1082, 197 USPQ 601 (CCPA 1978) (stereoisomers prima facie obvious); Aventis Pharma Deutschland v. Lupin Ltd., 499 F.3d 1293, 84 USPQ2d 1197 (Fed. Cir. 2007) (5(S) stereoisomer of ramipril obvious over prior art mixture of stereoisomers of ramipril.). Prior art structures do not have to be true homologs or isomers to render structurally similar compounds prima facie obvious. In re Payne, 606 F.2d 303, 203 USPQ 245 (CCPA 1979) (Claimed and prior art compounds were both directed to heterocyclic carbamoyloximino compounds having pesticidal activity. The only structural difference between the claimed and prior art compounds was that the ring structures of the claimed compounds had two carbon atoms between two sulfur atoms whereas the prior art ring structures had either one or three carbon atoms between two sulfur atoms. The court held that although the prior art compounds were not true homologs or isomers of the claimed compounds, the similarity between the chemical structures and properties is sufficiently close that one of ordinary skill in the art would have been motivated to make the claimed compounds in searching for new pesticides.). The presumption of obviousness based on a reference disclosing structurally similar compounds may be overcome where there is evidence showing there is no reasonable expectation of similar properties in structurally similar compounds. In re May, 574 F.2d 1082, 197 USPQ 601 (CCPA 1978) (appellant produced sufficient evidence to establish a substantial degree of unpredictability in the pertinent art area, and thereby rebutted the presumption that structurally similar compounds have similar properties); In re Schechter, 205 F.2d 185, 98 USPQ 144 (CCPA 1953).
In the instant case, and in view of MPEP 2144.09, the claimed compound and prior arts compounds are: homologs, because Kenda’s compound only differs by successive addition of the same chemical group, e.g., by -CH2- groups. Please note that the MPEP stated that “Prior art structures do not have to be true homologs or isomers to render structurally similar compounds prima facie obvious “; the claimed compound and the prior art compound have very close structural similarities and very similar properties as the claimed compounds and prior art compounds have similar utilities (both compounds target treatment of epilepsy related disorder; and applicant does not provide evidences of unexpectedly advantageous or superior properties of the claimed compounds over the prior art compounds. Therefore, Kenda’s above compound renders in claims 1 and 9 obvious.
Claim 26 is obvious because X4 is N; X5 is CR5 and R5 is H; X6 is CR6 and R6 is H; X7 is CR7 and R7 are H.
Claim 37 is obvious because R14 and R15 are taken together with the nitrogen atom to form a heterocycloalkyl substituted with alkyl.
With regard to claim 95, Kenda teaches a pharmaceutical composition comprising an effective amount of a compound of formula (I) in combination with a pharmaceutically acceptable diluent or carrier. [0593].
Conclusion
Claims 1, 9, 26, 37, 44, 82, and 95 are rejected. No claim is allowed.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to MANAHIL MIRGHANI ALI ABDALHAMEED whose telephone number is (571)272-1242. The examiner can normally be reached M-F 7:30 am - 5:00 pm.
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/M.M.A./Examiner, Art Unit 1622
/JAMES H ALSTRUM-ACEVEDO/Supervisory Patent Examiner, Art Unit 1622