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 .
Status of Claims
The amendments to the claims filed November 3, 2023 are acknowledged and entered. Claims 1-24 are pending.
Priority
This application is a 371 of PCT/US2022/027862, filed May 5, 2022, which claims the benefit of 63/184,433, filed May 5, 2021.
Information Disclosure Statement
Examiner kindly reminds applicant of the following: Applicants and other individuals substantially involved with the preparation and/or prosecution of the application have a duty to disclose to the office all information known to that individual to be material to patentability as defined in 37 CFR §1.56.
Specification
The specification has not been checked to the extent necessary to determine the presence of all possible minor errors. Applicant’s cooperation is requested in correcting any of the errors of which applicant may become aware of in the specification.
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 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 1-11 and 20 are rejected under 35 U.S.C. 103 as being unpatentable over Davis et al. (Journal of Psychopharmacology 32(7) 2018, 779-792)(hereinafter “Davis”) in view of Meanwell (Journal of Medicinal Chemistry 61, 2018, 5822-5880)(hereinafter “Meanwell”).
Davis teaches 5-Methoxy-N,N-dimethyltryptamine (5-MeO-DMT) is a psychoactive substance (Introduction, col 1; structure pictured below for convenience) that is a known agonist of the 5-HT receptor (page 780, col 1). Davis teaches a composition comprising 5-MeO-DMT and a carrier (page 783, col 1, plant extracts or other botanical preparation containing 5-MeO-DMT). Davis teaches there is evidence for the use of 5-MeO-DMT in treating psychiatric conditions, including mood disorders of the instant claims (page 780, col 1-2, people use 5-MeO-DMT for the purpose of treating conditions…including symptoms related to depression, anxiety symptoms post-traumatic stress disorder). Davis teaches the symptoms of mood disorders of the claims were reportedly better after 5-MeO-DMT use (page 784, col 2, reported symptoms associated with these medical conditions were better after 5-MeO-DMT use…disorders in the sample included anxiety, depression, drug use disorder, alcoholism or hazardous drinking, attention deficit hyperactivity disorder, post-traumatic stress disorder, eating disorder… comparatively larger proportions reported that their psychiatric conditions were improved following 5-MeO-DMT use). Davis teaches large proportions of respondents in this study reported that 5-MeO-DMT use contributed to improvements in symptoms related to several psychiatric conditions and problematic substance use (page 790, col 1) which includes mood disorders. Davis further teaches that 5-MeO-DMT use is illegal in the USA (page 780, col 1).
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The difference between prior art reference Davis and the instant claims is that the instant claims require a compound with a CF3 group in place of the CH3 group attached to oxygen in 5-MeO-DMT.
Davis does not teach wherein the CH3 group attached to oxygen in 5-MeO-DMT is replaced with a CF3 group. However, Meanwell teaches fluorine is a bioisostere of the hydrogen atom and that substitution of H for F can influence drug potency, conformation, metabolism and membrane permeability (Abstract). Meanwell teaches replacing hydrogen atoms with fluorine has been explored extensively in drug design in the context of a CF3 for CH3 replacement where these substitutions can modulate potency or interfere with metabolic modification (page 5823, col 1). Meanwell thus teaches it is common practice in drug design to exchange CH3 for CF3 as a way to optimize compound activity (e.g. potency) and metabolism.
It would have been prima facie obvious to a person of ordinary skill in the art before the effective filing date of the instant application to modify 5-MeO-DMT into the claimed compound to treat mood disorders as claimed because F was a known bioisostere of hydrogen, and, in particular, substituting CH3 for CF3 was a well-known strategy in the art for compound optimization.
One of ordinary skill in the art would have been motivated to make such a modification because at the time 5-MeO-DMT use was known to be illegal in the USA and this legal status would have hindered the use of 5-MeO-DMT as a therapeutic agent for treating psychiatric disorders including mood disorders. Modifying 5-MeO-DMT into the claimed compound by exchanging CH3 for CF3 would have resulted in a new compound that would not likely have the known legal restrictions of 5-MeO-DMT and therefore may be more useful in the treatment of conditions like mood disorders.
One would have had a reasonable expectation of success because exchanging CH3 for CF3 was a known strategy for optimizing compound potency. Therefore the modification would have been expected to result in a compound with similar activity and reported use in treating mood disorders as 5-MeO-DMT. In the present case, the instant compound is no more than the result of modifying the prior art compound 5-MeO-DMT according to well-known methods (exchanging CH3 for CF3) to produce a predicable result.
Claim(s) 1, 3, 12-19 and 21-24 is/are rejected under 35 U.S.C. 103 as being unpatentable over Davis et al. (Journal of Psychopharmacology 32(7) 2018, 779-792)(hereinafter “Davis”) and Meanwell (Journal of Medicinal Chemistry 61, 2018, 5822-5880)(hereinafter “Meanwell”) as applied to claims 1 and 3 above, and further in view of Olson et al. (WO2020/176599 A1) (hereinafter “Olson”).
The teachings of Davis and Meanwell with regard to claims 1 and 3 were discussed above and are incorporated herein by reference. Davis and Meanwell are silent regarding the claimed doses of administration (claims 12-19), route of administration (claim 21) and frequency of administration (claims 22-24); however, Olson teaches compounds of Formula (I) which are similar in structure to 5-MeO-DMT (see [0006]; Formula (I) and 5-MeO-DMT both require an optionally substituted indolyl ring; however, Formula (I) requires an additional ring formed between variable R2 and R3b or R3c). Olson teaches Formula (I) and 5-MeO-DMT are agonists of 5-HT2A (see [0025] Figure 14; [0150] compounds of the present invention have activity as 5-HT2A modulators…Hallucinogens (e.g….5-MeO-DMT) activate a 5HT2A sensor assay in agonist mode). Olson teaches Formula (I) treats brain diseases which includes mood disorders (see [0033] compounds described herein…produce antidepressant-like effects; [0147] compounds of the present invention can be used to treat any brain disease). Olson teaches suitable dosages of Formula (I) include about 1 mg, 5, 10, 20, 30, 40, 50, 60, 70, 80, 90, 100, 200, 300, 400, 500, 600, 700, 800, 900 or 1000 mg (see [0141]) which includes the claimed dosage ranges. Olson teaches Formula (I) may be administered orally (see [0139]). Olson teaches Formula (I) may be administered one to four times per day, from one to ten times per month, and from one to six times per year (see [0142] the compound of the present invention can be administered…three or more times per day…administered once, twice or three or more times…for a month, for a year).
The difference between Olson and the instant claims is that the instant claims are drawn to the treatment of mood disorders comprising administration of a different 5-HT2A agonist (compound of instant claim 1). However, it would have been prima facie obvious to one having ordinary skill in the art before the effective filing date of the instant application to combine the teachings of Davis and Meanwell with the dosages, routes of administration and frequency of administration disclosed in Olson into the claimed invention because Olson taught a method of treating mood disorders by administration of a 5-HT2A agonist.
One would have been motivated to use the teachings of Olson because the teachings illustrated dosages, routes and administration and frequency of administration of a 5-HT2A agonist that were required to treat mood disorders. Given the structural similarity between Formula (I) and 5-MeO-DMT (see [0006] and comment above) and that both compounds were disclosed agonists of 5-HT2A ([0025] and [0150] of Olson, also noted above), one would have been motivated to use the teachings of Olson as a framework for treating mood disorders with other 5-HT2A agonists such as 5-MeO-DMT and compounds, such as the instant compound, which are structurally related to 5-MeO-DMT. The teachings would have served as logical basis for treating mood disorders with a structurally similar 5-HT2A agonist.
One would have had a reasonable expectation of success because Olson had already disclosed
the claimed dosages, routes of administration and frequency of administration of a 5-HT2A agonist required to treat a mood disorder.
Conclusion
No claim is allowed.
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February 18, 2026
/KEVIN S MARTIN/Examiner, Art Unit 1624