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
Claims 1, 9, 13-17, 20-21, 26, and 30 are pending in the instant application.
Claims 2-8, 10-12, 18-19, 22-25, 27-29, and 31-35 have been canceled.
Withdrawn Rejections/Objections
Claims 1, 17, and 30 stand rejected under 35 U.S.C. 103 as being unpatentable over Sard et. al. (“SAR of psilocybin analogs: Discovery of a selective 5-HT2C agonist”, Bioorganic & Medicinal Chemistry Letters, 15, 4555-4559, 2005; cited on Applicant’s Information Disclosure Statement filed August 8th, 2024; cited in non-final rejection mailed June 13th, 2025; hereinafter referred to as Sard 2) in view of Pirali et. al. (“Applications of Deuterium in Medicinal Chemistry”, Journal of Medicinal Chemistry, 62, 5276-5297, 2019; cited in non-final rejection mailed June 13th, 2025; hereinafter referred to as Pirali).
Applicant traverses this rejection on the basis that the claimed compounds are structurally distinct from those cited in Sard 2.
The examiner finds this argument persuasive.
Sard 2 teaches the following group of compounds:
PNG
media_image1.png
245
180
media_image1.png
Greyscale
To arrive at the instantly claimed compounds, both the R substituent linker length as defined by n require modification. As Applicant notes in the remarks filed June 9th, 2026, Sard 2 demonstrates minor modifications substantially impact the activity and selectivity of the disclosed compounds. Sard 2 is absent of any teaching or motivation that would instruct a person having ordinary skill in the art to modify the variable n, above, to 2, and modify the R group, above, to one of the R3 groups instantly recited.
This rejection is hereby withdrawn.
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.
Claim 1 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by CAS Registry File 1525499-21-1 (entered into STN January 20th, 2014; hereinafter referred to as CAS Registry File).
CAS Registry File teaches the following compound:
PNG
media_image2.png
201
273
media_image2.png
Greyscale
This compound reads on a compound of Formula I as recited at instant Claim 1 when R1 and R3 are methyl and R3 and Z are each H.
Claim Rejections - 35 USC § 103
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
Claims 1, 9, 13, 14, and 30 stand rejected under 35 U.S.C. 103 as being unpatentable over Sard et. al. (WO 2006/047032 A1; cited on Applicant’s Information Disclosure Statement filed August 8th, 2024; cited in non-final rejection mailed June 13th, 2025; hereinafter referred to as Sard 1) in view of Meanwell (“Fluorine and Fluorinated Motifs in the Design and Application of Bioisosteres for Drug Design”, J. Med. Chem., 61, 5822-5880, 2018; cited in non-final rejection mailed June 13th, 2025). This rejection is maintained.
Applicant traverses this rejection in the remarks filed June 9th, 2026 on the basis that the instantly claimed compounds are structurally distinct from those taught in Sard-1, and that Sard-1 teaches away from the instantly claimed compounds due to the teaching of Sard 1 that “explicitly teaches the benefits of fluorine-substituted compounds related to improving the selectivity for 5-HT2c over 5-HT2A” at Page 5 of the remarks filed June 9th, 2026, and further, at Page 6 asserts that Sard 1’s teaching excludes unsubstituted compounds and a person having ordinary skill in the art would have been cautioned against replacing the fluorine with hydrogen to arrive at the presently claimed compounds.
The examiner does not find this argument persuasive.
As noted previously, Sard-1 teaches compounds of the following formula:
PNG
media_image3.png
157
176
media_image3.png
Greyscale
Sard 1 teaches compound 13 as a compound of this formula wherein R is CH2CH2CH3. This compound differs from a compound instantly claimed only in the presence of the fluorine atom.
Applicant asserts that Sard 1’s teaching cautions against replacement of the fluorine atom with a hydrogen atom. The specific quote applicant pulls from Sard 1 states that “Certain N-unsubstituted psilociix derivative containing fluorine substitution at the 5-,6-, or 7-position have been reported (…), and some of these compounds were shown to have reduced activity at the 5-HT2A receptor as compared to psilocin itself.”
This is not pertinent here, as this comment is directed toward substitution at a nitrogen atom, which is conserved.
At Page 5, Paragraph 0014 of the instant specification, Applicant states “there is an unmet need for safer drugs and analogs of psilocin that maintain 5-HT2A receptor agonist activity but that lack cardiotoxic 5-HT2B agonist activity.”
Sard 1, then, provides the motivation for replacing the fluorine atom taught by Sard 1 with a hydrogen atom to arrive at the instantly claimed compounds. Applicant acknowledges at Page 5 of the remarks filed June 9th, 2026 that “Sard-1 explicitly teaches the benefits of fluorine-substituted compounds related to improving the selectivity for 5-HT2c over 5-HT2A …” Therefore, a person having ordinary skill in the art would be motivated by this teaching to generate the instantly claimed compound, replacing the fluorine taught by Sard 1, for a hydrogen to address the established need of compounds with 5-HT2A activity.
Allowable Subject Matter
Claims 15-17, 20-21, and 26 are objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims.
Conclusion
Due to the newly raised rejection under 35 U.S.C. 102(a)(1), this rejection is non-final.
Claims 1, 9, 13, 14, and 30 are rejected.
Claims 15-17, 20-21, and 26 are objected to.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to DANIEL JOHN BURKETT whose telephone number is (703)756-5390. The examiner can normally be reached Monday - Friday.
Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Jeffrey Murray can be reached at (571) 272-9023. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
/D.J.B./Examiner, Art Unit 1624
/JEFFREY H MURRAY/Supervisory Patent Examiner, Art Unit 1624
Prosecution Insights