Prosecution Insights
Last updated: April 19, 2026
Application No. 18/747,540

3-PYRROLIDINE-INDOLE DERIVATIVES AS SEROTONERGIC PSYCHEDELIC AGENTS FOR THE TREATMENT OF CNS DISORDERS

Non-Final OA §103
Filed
Jun 19, 2024
Examiner
OH, TAYLOR V
Art Unit
1625
Tech Center
1600 — Biotechnology & Organic Chemistry
Assignee
Mindset Pharma Inc.
OA Round
2 (Non-Final)
81%
Grant Probability
Favorable
2-3
OA Rounds
2y 5m
To Grant
96%
With Interview

Examiner Intelligence

Grants 81% — above average
81%
Career Allow Rate
1415 granted / 1742 resolved
+21.2% vs TC avg
Strong +15% interview lift
Without
With
+15.3%
Interview Lift
resolved cases with interview
Typical timeline
2y 5m
Avg Prosecution
35 currently pending
Career history
1777
Total Applications
across all art units

Statute-Specific Performance

§101
0.4%
-39.6% vs TC avg
§103
33.6%
-6.4% vs TC avg
§102
19.5%
-20.5% vs TC avg
§112
37.3%
-2.7% vs TC avg
Black line = Tech Center average estimate • Based on career data from 1742 resolved cases

Office Action

§103
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 . Continued Examination Under 37 CFR 1.114 A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after allowance or after an Office action under Ex Parte Quayle, 25 USPQ 74, 453 O.G. 213 (Comm'r Pat. 1935). Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, prosecution in this application has been reopened pursuant to 37 CFR 1.114. Applicant's submission filed on 1/21/2026 has been entered. Non-Final Rejection The Status of Claims: Claims 1-18 are pending. Claims 1-4, 6, 9, 11, 14, and 16 are rejected. Claims 5, 7-8, 10, 12-13, 15, and 17-18 are objected. DETAILED ACTION 1. Claims 1-18 are under consideration in this Office Action. Priority 2. It is noted that this application is a continuation of 17879320 08/02/2022 (PAT 12054504), which is a division of 17387864 07/28/2021 (PAT 11453689) ,which is a continuation of PCT/CA2021/050122 (02/04/2021 ) , which has a priority of 62969894 02/04/2020. Drawings 3. The drawings filed on 6/19/24 are accepted by the examiner. IDS 4. The IDS filed on 1/21/26 & 1/27/26 were reviewed by the examiner. Claim Objections Claims 5, 7-8, 10, 12-13, 15, and 17-18 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. 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 set forth in Graham v. John Deere Co., 383 U.S. 1, 148 USPQ 459 (1966), that are applied 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. 5. Claims 1-4, 6, 9, 11, 14, and 16 are rejected under 35 U.S.C. 103 as being unpatentable over Carhart-Harris et al (Lancet Psychiatry, July 2016; vol 3 : 619–27). in view of Gerasimov et al (J. Med. Chem. 1999, 42, 4257-4263). Determination of the scope and content of the prior art Carhart-Harris et al teaches that serotonergic antidepressants have been found to downregulate the primary receptor target of psilocybin (the 5-HT2A receptor) and attenuated subjective responses to psychedelics have previously been reported in individuals chronically medicated with serotonergic antidepressants. In conclusion, the study assessed the safety and tolerability of psilocybin plus psychological support in patients with unipolar treatment-resistant depression. The findings support the feasibility of this approach and the magnitude and duration of the post-treatment reductions in symptom severity motivate further controlled research. Psilocybin has a novel pharmacological action in comparison with currently available treatments for depression (ie, 5-HT2A receptor agonism) and thus could constitute a useful addition to available therapies for the treatment of depression (see page 627, a left col. lines 8-16). The current invention, however, differs from the prior art in that the application of the claimed compound I-47 in the method for treating depression is unspecified in the prior art. Gerasimov et al teaches compounds in the followings: as shown below: PNG media_image1.png 170 242 media_image1.png Greyscale , PNG media_image2.png 207 189 media_image2.png Greyscale ( PNG media_image3.png 21 186 media_image3.png Greyscale (see page 4258, Scheme 2a. (S)-3) see page 4258, left col. ). PNG media_image4.png 356 613 media_image4.png Greyscale The enantiomers with highest affinity for the 5-HT2A receptor were then assessed in the drug discrimination paradigm (DD) in rats trained to discriminate either LSD tartrate from saline or DOI hydrochloride from saline. The affinities of the individual enantiomers are very similar for both 1 and 3. As would be expected for agonists, the affinities of all the compounds are correspondingly lower for the antagonist labeled receptor, although the relative affinity ratios for enantiomeric pairs remain approximately the same. Compounds 4 and 5 have lower affinities than the more active enantiomers (R)-1 and (R)-3, respectively, but still have 2-3-fold higher affinities than the less active S enantiomers of 1 and 3 (see page 4259, table 1, the first paragraph). Ascertainment of the difference between the prior art and the claims The difference between the instant application and the applied Carhart-Harris et al art is that the applied Carhart-Harris et al art does not expressly teach the application of the claimed compound I-47 for the method for treating depression. The deficiency of Carhart-Harris et al is cured partially by the Gerasimov et al. The difference between the instant application and the applied Gerasimov et al art is that the applied Gerasimov et al art does not expressly teach the method for treating depression by using the claimed compound I-47. The deficiency of Gerasimov et al is cured by the Carhart-Harris et al. Resolving the level of ordinary skill in the pertinent art. Regarding the Claims 1-4, 6, 9, 11, 14, and 16, with respect to the lack of disclosing the application of the claimed compound I-47 for the method for treating depression, Carhart-Harris et al is silent about it. However, Gerasimov et al does describe that compounds (R)/(S)-3, and Table 1 show that (R)-3 , which may correspond to the claimed compound I-47 , exhibits better activity than psilocin with respect to [3H]MDL 100907, a highly selective 5-HT2A receptor antagonist (see page 4259, table 1, the first paragraph). In addition, Carhart-Harris et al does teach that psilocybin has the pharmacological action in comparison with currently available treatments for depression (ie, 5-HT2A receptor agonism). Also, it is well-known fact that the chemical structure between psilocybin and psilocin is very similar to each other, thereby possessing a very similar chemical activity. So, if the skilled artisan in the art had desired to treat depression by using (R)-3 compound as an alternative to psilocybin, it would have been obvious to the skilled artisan in the art to be motivated to incorporate the teaching of Gerasimov’s (R)-3 compound into Carhart-Harris’ et al method of treating depression. This is because the skilled artisan in the art would expect such combined prior art to be feasible and successful as shown in the prior art. Considering objective evidence present in the application indicating obviousness or nonobviousness. Carhart-Harris et al expressly teaches that psilocybin has the pharmacological action in comparison with currently available treatments for depression (ie, 5-HT2A receptor agonism). Whereras Gerasimov et al expressly teaches compounds in the followings: as shown below: PNG media_image1.png 170 242 media_image1.png Greyscale , PNG media_image2.png 207 189 media_image2.png Greyscale ( PNG media_image3.png 21 186 media_image3.png Greyscale (see page 4258, Scheme 2a. (S)-3) see page 4258, left col. ). Also, it is well-known fact that the chemical structure between psilocybin and psilocin are very similar to each other, thereby possessing a very similar chemical activity. Furthermore, Gerasimov et al does offer guidance that compounds (R)/(S)-3, and Table 1 show that (R)-3 exhibits better activity than psilocin with respect to [3H]MDL 100907, a highly selective 5-HT2A receptor antagonist ,whereas So, if the skilled artisan in the art had desired to treat depression by using (R)-3 compound as an alternative to psilocybin, it would have been obvious to the skilled artisan in the art before the effective filing date of the claimed invention to be motivated to incorporate the teaching of Gerasimov’s (R)-3 compound into Carhart-Harris’ et al method of treating depression. This is because the skilled artisan in the art would expect such a modification to be feasible and successful as shown in the prior art Conclusion Claims 1-4, 6, 9, 11, 14, and 16 are rejected. Claims 5, 7-8, 10, 12-13, 15, and 17-18 are objected. Any inquiry concerning this communication or earlier communications from the examiner should be directed to TAYLOR V OH whose telephone number is (571)272-0689. The examiner can normally be reached 8:00-5:00. 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, Andrew Kosar can be reached on 571-272-0913. 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. Any inquiry concerning this communication or earlier communications from the examiner should be directed to TAYLOR V OH whose telephone number is (571)272-0689. The examiner can normally be reached 8:00-5:00. 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, Andrew Kosar can be reached at 571-272-0913. 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. /TAYLOR V OH/ Primary Examiner, Art Unit 1625 1/31/2026
Read full office action

Prosecution Timeline

Jun 19, 2024
Application Filed
Feb 18, 2025
Non-Final Rejection — §103
May 20, 2025
Response after Non-Final Action
May 20, 2025
Response Filed
Jun 09, 2025
Response Filed
Jan 21, 2026
Request for Continued Examination
Jan 26, 2026
Response after Non-Final Action
Jan 31, 2026
Non-Final Rejection — §103 (current)

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Study what changed to get past this examiner. Based on 5 most recent grants.

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Prosecution Projections

2-3
Expected OA Rounds
81%
Grant Probability
96%
With Interview (+15.3%)
2y 5m
Median Time to Grant
Moderate
PTA Risk
Based on 1742 resolved cases by this examiner. Grant probability derived from career allow rate.

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