NON-FINAL REJECTION
This application, filed Jul. 25, 2024, claims benefit of priority to Provisional Application 63/529,077, filed Jul. 26, 2023.
Claims 1-16, 33, 34, and 36-51, as amended, are pending.
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
Applicant’s claim for the benefit of a prior-filed application under 35 U.S.C. 119(e) or under 35 U.S.C. 120, 121, or 365(c) is acknowledged.
Information Disclosure Statement
The information disclosure statements (IDS) submitted on Sep. 11, 2024, Jun. 24, 2025, Aug. 4, 2026, and Aug. 19, 2026 are in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statements are being considered by the examiner.
Election/Restrictions
Applicant’s election without traverse of Group I, drawn to compounds of formula (I), and the compound species (I-10) (5-(4-chlorophenyl)-5-isobutoxy-2,5-dihydro-3H-imidazo[2,1-a]isoindole), having the structural formula,
Elected Species (I-10)
Claimed Formula (I)
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in the reply filed on Sep. 3, 2026 is acknowledged.
The elected compound species (I-10) reads on formula (I) as recited by claims 1-4, 16, 33, 38, and 40-51, wherein R1 is isobutyl; R12 is chloro; and R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R13, and R14 are hydrogen.
Claims 5-15, 34, 36, 37, and 39 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to nonelected inventions and/or species, there being no allowable generic or linking claim. Election was made without traverse in the reply filed on Sep. 3, 2026.
Claims 1-4, 16, 33, 38, and 40-51 are currently pending and under consideration.
Claim Rejections - 35 USC § 112(d) – Improper Dependency
The following is a quotation of 35 U.S.C. 112(d):
(d) REFERENCE IN DEPENDENT FORMS.—Subject to subsection (e), a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
The following is a quotation of pre-AIA 35 U.S.C. 112, fourth paragraph:
Subject to the following paragraph [i.e., the fifth paragraph of pre-AIA 35 U.S.C. 112], a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
Claims 47, 48, 50, and 51 are rejected under 35 U.S.C. 112(d) or pre-AIA 35 U.S.C. 112, 4th paragraph, as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends.
Specifically, claims 47 and 48 fail to further limit claim 45 from which they depend, because claim 45 recites compounds of claim 43, wherein R1 is isopropyl, isobutyl, sec-butyl, t-butyl, neopentyl, or isopentyl, all of which are inherently branched alkyl groups, as recited by claim 47; and are duplicated in claim 48.
Similarly, claims 50 and 51 fail to further limit claim 48 from which they depend, because claim 48 recites compounds of claim 45, wherein R1 is isopropyl, isobutyl, sec-butyl, t-butyl, neopentyl, or isopentyl, all of which are inherently branched alkyl groups, as recited by claim 50; and are duplicated in claim 51.
It suggested to amend claims 47-48 to depend from claim 46; and to amend claims 50-51 to depend from claim 49.
Applicant may cancel the claim(s), amend the claim(s) to place the claim(s) in proper dependent form, rewrite the claim(s) in independent form, or present a sufficient showing that the dependent claim(s) complies with the statutory requirements.
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.
Claims 1-4, 16, 40, 43, 46, and 49 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Barcza et al. (J. Pharm. Sci. 64 (5), pp. 829-831 (1975), cited on PTO-892).
Barcza et al. exemplify compound (Ic) (Scheme I, p. 829), having the structural formula,
Barcza et al.
Compound (Ic)
Claimed Compound (I-8)
(Claims 4 and 16)
Claimed Formula (I)
(Claim 1)
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which reads on formula (I) as recited by claims 1-4, 16, 40, 43, 46, and 49, wherein R1 is ethyl; R12 is chloro; and R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R13, and R14 are hydrogen.
As shown above, compound (Ic) of Barcza et al. is identical to compound (I-8) (5-(4-chlorophenyl)-5-ethoxy-2,5-dihydro-3H-imidazo[2,1-a]isoindole) as recited by claims 4 and 16.
For the foregoing reasons, Barcza et al. anticipates claims 1-4, 16, 40, 43, 46, and 49.
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.
Claims 1-4, 16, 33, 38, and 40-51 are rejected under 35 U.S.C. 103 as being unpatentable over Metlesics et al. (USPN 3,931,217, cited on PTO-892).
Metlesics et al. disclose 1,3-diazacycloalkenyl[2,1-a]isoindoles having useful anorexigenic and psychostimulant properties as pharmaceuticals (abstract; col. 1, lines 12-15).
In particular, Metlesics et al. exemplify 2,3-dihydro-5-methoxy-5-phenyl-5H-imidazo[2,1-a]isoindole hydrochloride salt (Example 19), having the structural formula,
Metlesics et al. Compound 19
Claimed Formula (I)
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which reads on formula (I) as recited by claims 1-4, 16, 33, 38, and 40-51, to the extent that R1 is alkyl (methyl), and R2 through R14 are hydrogen.
The compounds of Metlesics et al. are disclosed to be formulated into preparations for administration by enteral or parenteral routes. In general, the formulations will be prepared with pharmaceutically acceptable adjuvant materials (col. 14, lines 24-66), as recited by claim 33.
Compound 19 of Metlesics et al. differs from the elected compound species (I-10) in that R12 is hydrogen instead of chloro, and R1 is methyl instead of isobutyl.
Metlesics et al. Compound 19
Elected Species (I-10)
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However, Metlesics et al. disclose compound 19 as a species of the formula defined in claim 1, wherein R1 and R3 are each hydrogen or halogen, and R7 is lower alkyl:
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Regarding the chloro substituent, Metlesics et al. further exemplify the compounds of Example 9 (5-(p-chlorophenyl)-2,3-dihydro-5-hydroperoxy-5H-imidazo[2,1-a]isoindole HCl) and Example 15 (5-(4-chlorophenyl)-2,3-dihydro-5-hydroxy-5H-imidazo[2,1-a]isoindole), each having R3 defined as chloro in the para position.
Thus, Metlesics et al. expressly disclose, teach, and suggest not only halogen at R3, but specifically a chloro in the para position, i.e., at R12 of claimed formula (I).
Regarding the isobutyl substituent, R7 of formula (I) of Metlesics et al. is limited to lower alkyl, generally understood by those skilled in the chemical arts as C1-6 alkyl. Because compound 19 is exemplified with methyl in this position, Metlesics et al. expressly disclose, teach, and suggest that this alkoxy methyl group can be extended to C4-alkyl, e.g., isobutyl.
Therefore, it would have been predictable to one of ordinary skill in the art as of the filing date to modify the compound of Example 19 of Metlesics et al. to arrive at the elected compound species (I-10) with a reasonable expectation of success, because compound genus of Metlesics et al. is very small, and expressly encompasses these two modifications to Compound 19. Further, the compounds of Metlesics et al. are disclosed for the same use as the claimed compounds, as pharmaceuticals for the treatment CNS disorders.
As recognized by MPEP § 2144.09, compounds which are homologs (i.e., differing regularly by the successive addition of the same functional group, e.g., CH2) are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties. See In re Wilder, 563 F.2d 457, 195 USPQ 426 (CCPA 1977).
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, 16, 33, 40, 43, 46, and 49 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-5 of U.S. Patent No. 12,454,535. Although the claims at issue are not identical, they are not patentably distinct from each other because the reference claims would anticipate the examined claims.
Reference claim 1 recites compounds of formula (I), having the structural formula,
Reference Claim 1
Formula (I)
Examined Claim 1
Formula (I)
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R1 is a dioxolanylmethyl group
R1 is an alkyl group, an alkenyl group, an aralkyl group, an alkoxyalkyl group, a carboxyalkyl ester group, a cinnamyl group, a heteroalkyl group or a heterocycloalkyl group;
R2-R5 are each independently H or alkyl
R2-R5 are each independently H or alkyl
R6-R11, R13 and R14 are each independently H, alkyl, alkoxy, F, Cl, Br, CF 3 or I
R6-R14 are each independently H, alkyl, alkoxy, F, Cl, Br, CF3 or I
R12 is alkyl, alkoxy, F, Cl, Br, CF3 or I
at least one of R6-R14 is alkyl, alkoxy, F, Cl, Br, CF3 or I
Reference formula (I) falls within the scope of examined formula (I), because the alkyl, alkoxy, F, Cl, Br, CF3 or I substituent is specifically at R12; and because the dioxolanylmethyl group at R1 reads on heteroalkyl.
The instant specification defines “alkyl” to include C1-20 straight chain and branched alkyl groups, as well as cycloalkyl groups (para. [0046]), including, e.g., cyclopentyl (para. [0047]). Wherever “hetero” is used it is intended to mean a group as specified, where at least one carbon atom has been replaced with a heteroatom selected from the group consisting of nitrogen, oxygen, and sulfur (para. [0053]).
Thus, reference formula (I), requiring a dioxolanylmethyl substituent at R1 of reference claim 1, and the compound species (I-19) of reference claim 2,
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fall within the scope of “heteroalkyl” at R1 as recited by examined claim 1. Further, reference compound (I-19) is recited by examined claim 16.
Reference claim 3 recites compound (I-1) (5-(benzyloxy)-5-(4-chlorophenyl)-2,5-dihydro-3H-imidazo[2,1-a]isoindole, having the structural formula,
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which falls within the scope of examined formula (I), wherein R1 is benzyl (aralkyl). Further, reference compound (I-1) is recited by examined claim 16.
Reference claim 4 is drawn to a composition comprising a compound of formula (I), and a pharmaceutically acceptable excipient, which reads on examined claim 33.
Reference claim 5 is drawn to the compound of formula (I), wherein R12 is Cl, which falls within the scope of examined formula (I), which requires at least one of R6-R14 to be alkyl, alkoxy, F, Cl, Br, CF3 or I.
For the foregoing reasons, the reference claims would anticipate the examined claims.
Claims 1-4, 16, 33, 38, and 40-51 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-2 of copending Application No. 18/899,299 (reference application). Although the claims at issue are not identical, they are not patentably distinct from each other because the reference claims would anticipate the examined claims.
Reference claim 1 is drawn to a method for treating a central nervous system disorder in a subject in need thereof, comprising administering a therapeutically effective amount of a compound of Formula I, II, or III, or a stereoisomer thereof, or a pharmaceutically acceptable salt thereof, wherein formula (I) has the structural formula shown below:
Reference Claim 1
Formula (I)
Examined Claim 1
Formula (I)
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R1 is an alkyl group, an alkenyl group, an aralkyl group, an alkoxyalkyl group, a carboxyalkyl ester group, a cinnamyl group, a heteroalkyl group or a heterocycloalkyl group;
R1 is an alkyl group, an alkenyl group, an aralkyl group, an alkoxyalkyl group, a carboxyalkyl ester group, a cinnamyl group, a heteroalkyl group or a heterocycloalkyl group;
R2-R5 are each independently H or alkyl;
R2-R5 are each independently H or alkyl
R6-R14 are each independently H, alkyl, alkoxy, F, Cl, Br, CF3 or I;
R6-R14 are each independently H, alkyl, alkoxy, F, Cl, Br, CF3 or I,
wherein at least one of R6-R14 is alkyl, alkoxy, F, Cl, Br, CF3 or I
Further, reference claim 2 recites the elected compound species (I-10) (5-(4-chlorophenyl)-5-isobutoxy-2,5-dihydro-3H-imidazo[2,1-a]isoindole), as recited by examined claims 1-4, 16, 38, and 40-51.
It is implicit in the methods for treating a central nervous system disorder in a subject in need thereof comprising administering a therapeutically effective amount of a compound of Formula I, as recited by the reference claims, that the compound is formulated in a composition together with a pharmaceutically acceptable excipient, as recited by examined claim 33.
For the foregoing reasons, the reference claims would anticipate the examined claims.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Conclusion
No claims are allowed.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to SARA E. TOWNSLEY whose telephone number is 571-270-7672. The examiner can normally be reached on Mon-Fri from 10:00 am to 6:00 pm (EST). If attempts to reach the examiner by telephone are unsuccessful, the examiner's supervisor, Jeff S. Lundgren, can be reached at 571-272-5541. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/SARA E. TOWNSLEY/Examiner, Art Unit 1629
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