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 .
DETAILED ACTION
Status of the Claims
Claims 1-15 are pending. Claims 6-8 are withdrawn from further consideration as being directed towards nonelected species until a generic claim has been found allowable (note that claim 8 requires that R2 and R3 form a cycloalkyl group). Claims 1-5 and 9-15 are examined on their merits.
Information Disclosure Statement
The Information Disclosure Statement filed on July 1st 2026 is in compliance with the provisions of 37 CFR 1.97 and has been considered in full. A signed copy of references cited from the IDS is included with this Office Action.
35 U.S.C. § 112(b) Rejections Overcome by Amendment
Applicant’s amendments in the response filed on July 1st 2026 are acknowledged. Applicant has amended claims 13-15 to no longer recite the indefinite condition of “a disease associated with pain.” Claims 13-15 are thereby definite and the 112(b) rejections over the claims are withdrawn.
35 U.S.C. § 102(a)(2) Rejections Maintained
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)(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.
The rejection of claims 1-4 and 10-14 under 35 U.S.C. 102(a)(2) as being anticipated by Hagel (WO 2023/173227 published on September 21st 2023, effectively filed on March 18th 2022) is maintained.
Applicant’s amendments in the response filed on July 1st 2026 are acknowledged. Applicant has amended the claims so the R1 position no longer encompasses C=O. While this amendment removes Hagel’s compound D(IV) from the genus of Formula (I), further anticipatory compounds remain. See Hagel’s compound D(II), which is anticipatory of claims 1-4:
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Claim 10 is directed to pharmaceutical compositions comprising the compound of claim 1. Hagel teaches pharmaceutical compositions (Hagel, paragraph [00403]), anticipating claim 10.
Claim 11 is directed to the treatment of conditions that are responsive to serotonin receptor activation. Hagel teaches treatment of depressive disorders (Hagel, paragraph [00408]) and that such disorders are responsive to serotonin activation (Hagel, paragraph [00152]). Hagel therefore anticipates claim 11.
Claims 12-14 are directed to the treatment of psychiatric disorders, such as borderline personality disorder, via administration of the compound of claim 1. Hagel teaches the treatment of psychiatric disorders including borderline personality disorder (Hagel, paragraph [00408]), anticipating claims 12-14.
The 102 rejections over Hagel are thereby maintained.
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.
The rejection of claim 15 is rejected under 35 U.S.C. 103 as being unpatentable over Hagel (WO 2023/173227 published on September 21st 2023, effectively filed on March 18th 2022) is maintained.
The 103 rejection of claim 15 is maintained for the same reasons as the above 102 rejections.
The rejection of claims 5, and 9 under 35 U.S.C. 103 as being unpatentable over Hagel in view of Brown (Brown, Bioisosteres in Medicinal Chemistry (2012)).
Applicant argues in the response filed on July 1st 2026 that
One of ordinary skill in the art would not have reasonably chosen Hagel’s compound D(I) to modify.
One of ordinary skill in the art would not have reasonably chosen the H[Wingdings font/0xE0]Me modification.
Applicant’s compounds constitute a case of unexpected results, because applicant’s compounds exhibit significantly higher 5-HT2A receptor activity than psilocin, for which applicant’s compounds serve as a prodrug.
Applicant’s arguments are found not persuasive.
Regarding applicant’s first argument, Hagel teaches just 19 compounds to choose from. This represents a small, finite number of compounds to choose from. See MPEP § 2143(I)(E). One of ordinary skill in the art would therefore have a reasonable expectation of success in choosing Hagel’s compound D(I) to modify.
Regarding applicant’s second argument, while Brown does indeed present a large variety of possible bioisosteric substitutions, the H[Wingdings font/0xE0]Me substitution is extremely common and has been used in the field of drug development for over 70 years (See Brown, pg. 7, where classical bioisosterism is described). One of ordinary skill in the art would reasonably expect applicant’s compound to have similar properties to Hagel’s, which varies only in this single substitution.
As a preliminary note, as described above, the extremely close structural similarity between Hagel’s compound D(I) and applicant’s elected compound renders the compounds obvious variants, absent the case of unexpected results. Regarding applicant’s claim of unexpected results, applicant’s arguments are found not persuasive for the following reasons:
Applicant has not provided a comparison with the closest prior art.
Applicant’s beneficial results are expected.
Applicant argues that the modifications that result in applicant’s elected species are nonobvious because they provide unexpectedly better pharmokinetic properties than psilocin itself, in that there is significantly higher 5-HT2A receptor radioligand displacement activity. Applicant supports this argument with a comparison between applicant’s compounds, and psilocin itself.
However, as demonstrated above, Hagel’s compounds share far more structural similarity to applicant’s compounds than psilocin. Thus, a proper comparison would demonstrate that applicant’s compounds are significantly better than compounds which share a similar polyether chain.
As demonstrated by Hagel, compounds of this class would be expected to give such an increase in 5-HT2A binding and psilocin release (see Hagel, Figures 10D, 11D, 12D, 13D, 10F, 11F, 12F, 13F). Such improvements are not surprising, but are expected for compounds of this class.
Applicant’s arguments that claims 5 and 9 are nonobvious on the grounds of unexpected results are found not persuasive and the 103 rejections for claims 5 and 9 are maintained.
35 U.S.C. § 103 Rejection of Claim 15 Reiterated.
Claim 15 is rejected under 35 U.S.C. 103 as being unpatentable over Hagel (WO 2023/173227 published on September 21st 2023, effectively filed on March 18th 2022).
Claim 15 requires that the neurological disease treated in the method of claim 13 is pain or associated with pain. Hagel teaches modulation of the 5-HT2A receptor (Hagel, claim 61) and that the modulation of such a receptor is a treatment for migraines (Hagel, paragraph [00156]). One of ordinary skill in the art would therefore have a reasonable expectation of success in treating migraines with Hagel’s compounds, and claim 15 is prima facie obvious.
35 U.S.C. § 103 Rejection of Claims 5 and 9 Reiterated.
Claims 5, and 9 are rejected under 35 U.S.C. 103 as being unpatentable over Hagel in view of Brown (Brown, Bioisosteres in Medicinal Chemistry (2012)).
Claims 5 and 9 are directed towards applicant’s elected species of:
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Hagel teaches the substantially similar compound D(I):
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(Hagel, pg. 180).
Applicant has provided a proviso in claim 1, that the compound is not compound D(I). Therefore, compound D(I) is not anticipatory of applicant’s claims. However, compound D(I) differs from applicant’s elected species only in the replacement of a single hydrogen atom with a methyl group. This replacement is one of the most common bioisosteric substitutions performed in the field of drug discovery (Brown, pg. 17). One of ordinary skill in the art would therefore have a reasonable expectation of success in developing applicant’s elected species from Hagel’s compound D(I), and claims 5 and 9 are prima facie obvious.
Conclusion
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 Anthony Seitz whose telephone number is (703)756-4657. The examiner can normally be reached 7:30 AM ET - 5:00 PM ET M-F.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Jeffrey 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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/A.J.S./Examiner, Art Unit 1629
/JEFFREY S LUNDGREN/Supervisory Patent Examiner, Art Unit 1629
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