DETAILED ACTION
This Office action in in response to amendments filed June 22, 2026. Claims 1-17, 19-27 and 32-33 are pending. Claims 1-14 and 19 are withdrawn. Claim 15-17, 20-27 and 32-33 are drawn to the elected species.
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 . 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.
Withdrawn Rejections
The rejection of claims 15-18 and 20-28 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or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention is withdrawn in light of applicant’s amendments.
The rejection of claims 15-17 and 20-27 under 35 U.S.C. 103 as being unpatentable over Matinkhoo et al (WO 2023173229; cited in PTO-892 herein) is withdrawn in light of applicant’s amendments to claim 15.
Modified Rejection Necessitated by Applicant’s Amendments
Claim Rejections - 35 USC § 103
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.
Claims 15-17, 20-27 and 32-33 are rejected under 35 U.S.C. 103 as being unpatentable over Gilles et al (WO 2023122320; cited in PTO-892 dated 3/19/26).
Gilles et al teach polypodal compounds and prodrugs of serotonergic compounds for treating and preventing a variety of human conditions (pg. 1, lines 10-12). One of the compounds disclosed is:
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(pg. 115, compound 1F, wherein n and q can be 0 and L3 can be chosen from cycloalkyl including cyclopropyl (pg. 9, lines 17-23; pg. 18, lines 14-18; pg. 19, lines 8-9 and lines 12-13), which meets the compound of Formula II, wherein A is cycloalkyl, R’ and R’’ are independently methyl and each Rx is independently hydrogen.
However, the compound of Formula II is not immediately envisaged within the teachings of Gilles et al.
Nevertheless, it would have been obvious to select and use the compound of Formula II within the teachings of Gilles et al for the intended use of treating brain neurological disorders. In this case, it would have been obvious to start with compound 1F of Gilles et al and only further select from the variables of L2, L3, L4 as well as n and q. In KSR v. Telefex, 82 USPQ2d 1385, 1397 (U.S. 2007), the Supreme Court has held that when there is market pressure to solve a problem and there are a finite number of identified, predictable solutions, a person has good reason to pursue known options within his or her technical grasp. The court has reasoned a reasonable expectation of success in the art by stating that reading a list and selecting a known compound to meet known requirements is no more ingenious than selecting the last piece to put in the last opening in a jig-saw puzzle. Sinclair & Carroll Co., 325 U.S. at 335, 65 USPQ at 301.
Regarding claim 16, Gilles et al teach the compound according to Formula II wherein R’ and R’’ are each methyl.
Regarding claim 17, Gilles et al teach the compound according to Formula II wherein Rx is independently hydrogen.
Regarding claim 20, Gilles et al teach the compound according to Formula II wherein A is C3-C12 cycloalkyl.
Regarding claim 21, Gilles et al teach the compound, bis(3-(2-(dimethylamino) ethyl-1H-indol-4-yl) (1S,2S)-cyclopropane-1,2-dicarboxylate (pg. 115, compound 1F, wherein n and q can be 0 and L3 can be chosen from cycloalkyl including cyclopropyl (pg. 9, lines 17-23; pg. 18, lines 14-18; pg. 19, lines 8-9 and lines 12-13).
Regarding claim 22, Gilles et al teach the compound according to Formula II in pharmaceutical compositions with a pharmaceutically acceptable carrier (pg. 60, lines 22-31).
Regarding claims 23-26 and 33, Gilles et al teach the compounds according to Formula II are contained within compositions that are used to treat brain neurological disorders including anxiety disorders (conditions responsive to serotonin receptor activation), like posttraumatic stress disorder among many others, etc. (pg. 58, line 35—pg. 59, line 13).
Regarding claim 27, Gilles et al teach the compounds according to Formula II are used to treat pain and diseases associated with pain (pg. 59, lines 29-31).
Regarding claim 32, Gilles et al teach the compound, bis(3-(2-(dimethylamino) ethyl-1H-indol-4-yl) (1S,2S)-cyclopropane-1,2-dicarboxylate (pg. 115, compound 1F, wherein n and q can be 0 and L3 can be chosen from cycloalkyl including cyclopropyl (pg. 9, lines 17-23; pg. 18, lines 14-18; pg. 19, lines 8-9 and lines 12-13), which is the compound having the structure of claim 32.
Response to Arguments
Applicant's arguments filed 6/22/26 have been fully considered but they are not persuasive.
With respect to Gilles et al, applicant argues that the reference does not provide any preference or motivation that would direct a skilled artisan to make this specific series of selections from the many available subgenera to arrive at the subgenera recited in the pending claims. Because the claimed compounds can only be envisioned from the references using impermissible hindsight, applicant respectfully submits the claims are not obvious.
In response to applicant’s arguments, it is noted that the 103 rejection over Gilles above is modified due to applicant’s amendments. In this case, it would have been obvious to start with the compound 1F of Gilles and only further select from the variables of L2, L3, L4 as well as n and q and envision the compound of Formula II recited in the instant claims. There are a finite number of variables and thus, a skill artisan would have good reason to pursue known options within his or her technical grasp. Further, there does not appear to be any criticality with respect to selecting these variables according to applicant’s specification (see additional discussion below). In response to applicant's argument that the examiner's conclusion of obviousness is based upon improper hindsight reasoning, it must be recognized that any judgment on obviousness is in a sense necessarily a reconstruction based upon hindsight reasoning. But so long as it takes into account only knowledge which was within the level of ordinary skill at the time the claimed invention was made, and does not include knowledge gleaned only from the applicant's disclosure, such a reconstruction is proper. See In re McLaughlin, 443 F.2d 1392, 170 USPQ 209 (CCPA 1971).
Applicant further submits that the claimed compounds (i.e., the compound of claim 32) exhibit unexpectedly superior biological activity that would not have been predicted from the teachings of Gilles. Applicant argues that the claimed compounds exhibited 5-HT2A radioligand displacement activity rated higher than psilocin itself (Example 6, Table 3), demonstrating superior activation of the 5-HT2A receptor at a level exceeding that of psilocin.
However, Table 3 in the specification appears to compare i.) dimer compounds of psilocin to ii.) compounds with one monomer of psilocin. Gilles clearly demonstrate dimer compounds of psilocin bridged via ester bonds. The difference between the compounds of Gilles and the compounds of the claimed invention is the A moiety or linker between the dimer compounds of psilocin. In this case, applicant has not provided any data or evidence that the A moiety or linker between the dimer compounds of psilocin is critical or results in a compound with unexpectedly superior biological activity. Further, Applicant is reminded that any objective evidence presented must be commensurate in scope with the claims which the evidence is offered to support. Since properties of chemical compounds can be highly variant, any results must be extended to the full range of compounds claimed including the broadest scope of independent claim 15.
As such, the modified 103 rejection over Giles is maintained for the reasons stated above.
Conclusion
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). 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 RACHAEL E BREDEFELD whose telephone number is (571)270-5237. The examiner can normally be reached 8:00-5:00 Monday-Friday.
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/RACHAEL E BREDEFELD/Supervisory Patent Examiner, Art Unit 3786
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