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
This office action is in response to Applicant’s Remarks filed on 27 February 2026, for application 18/337,253 filed on 19 June 2023, with PRO 63/353,673 filed on 20 June 2022. Claims 1-16 are canceled. Claims 17-36 are new. Currently, claims 17-36 are pending.
Information Disclosure Statement
The information disclosure statement (IDS) submitted on 27 February 2026 was filed after the mailing date of the application on 19 June 2023. The submission is in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statement is being considered by the examiner.
Election/Restrictions
Applicant’s election of new claims 17-36 which read upon Group I of the restriction requirement, originally directed to compounds of previous claims 1-6, 15 and 16, is acknowledged.
Applicant’s election of compound 16b or a pharmaceutically acceptable salt thereof, illustrated below, is acknowledged:
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Applicant informs that claims 17-19, 21, 24-26, 28, and 35 read upon this election.
Claims 20, 22-23, 27, 29-34 and 36 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a non-elected invention or species, there being no allowable generic or linking claim. Election was made without traverse (prejudice) in the reply filed on 27 February 2026.
The elected species was searched and found to be free of the prior art.
The closest match are structures described by Ručman et al. (Ergoline derivatives of 1-propinylamine, a process for the manufacture thereof and the use thereof for medicaments, 5,480,885, 1996), M. Grill (Improved method for the production of lysergic acid diethylamide (LSD) and novel derivatives thereof, WO 2022/008627 A2, 13 January 2022; entered into the IDS on 27 February 2026), and Niwaguchi et al. (Studies on lysergic acid diethylamide and related compounds. IV. Syntheses of various amide derivatives of norlysergic acid and related compounds, Yakugaku Zasshi 1976, 96, 5, 673-678) as described by structure IV- example 1, L2, and 34, respectively:
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Claim Objections
Claim 19 objected to because of the following informalities: R8’ is mistakenly included after R8 is H as R8’ appears after this initial section. Alkyl is inappropriately used twice in the section C4-C7 cylcoalkylalkyl. Appropriate correction is required.
Claim 26 is objected to because of the following informality: the chemical structures are illegible and should be replaced. Appropriate correction is required.
Claim Rejections - 35 USC § 102
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)(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.
Claims 17-19 and 24-25 is rejected under 35 U.S.C. 102(a)(1) and 35 U.S.C. 102(a)(2) as being anticipated by Ručman et al. (Ergoline derivatives of 1-propinylamine, a process for the manufacture thereof and the use thereof for medicaments, 5,480,885, 1996).
Ručman discloses structure IV that reads on class 2 where R6 = CH3, R8 = Et, and R8’=C3 alkynyl, 9,10-didehydro-N-(2’-propinyl)-6-methylergoline-8β-carboxamide D-lysergic acid though only the general structure is illustrated (pg. 3, col. 4 – example 1):
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As such, Ručman anticipates claim 17, class 3.
Concerning the limitation of claim 18, wherein the compound is of Class 3, or a pharmaceutically acceptable salt thereof, is met as Ručman discloses structure IV, 9,10-didehydro-N-(2’-propinyl)-6-methylergoline-8β-carboxamide D-lysergic acid, which reads on Class 3 compounds.
Regarding the limitations of claim 19, wherein R8 is H, C1-C5 alkyl, C3-C5 cycloalkyl, C4-C7 cycloalkyl, C2-C5 alkenyl, or C2-C5 alkynyl; and R8’ is C3-C7 alkynyl optionally substituted with one or more F, further optionally substituted with one or more CN, OH, and/or = O, wherein the C≡C triple bond is not adjacent to N, are met as the structure disclosed by Ručman reads upon this limitation where R8 = Et, and R8’=C3 alkynyl (pg. 3, col. 4 – example 1).
With regards to the limitations of claim 24, wherein the compound is a pharmaceutically acceptable acid addition salt of a compound of Class 2 or Class 3, are met as Ručman discloses obtaining crystals of the tartrate salt from fractions 20 to 30 in their crystallization efforts, an acid salt, instead of the free base (col. 4, lines 51-53).
Concerning the limitations of claim 25, wherein the compound is a salt of a compound of Class 2 or Class 3, are met as stated above in para. 15.
Claim Rejections - 35 USC § 103
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 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 non-obviousness.
Claim 26 is rejected under 35 U.S.C. 103 as being unpatentable over Ručman et al. (Ergoline derivatives of 1-propinylamine, a process for the manufacture thereof and the use thereof for medicaments, 5,480,885, 1996) in view of M. Grill (Improved method for the production of lysergic acid diethylamide (LSD) and novel derivatives thereof, WO 2022/008627 A2, 13 January 2022).
Ručman discloses 9,10-didehydro-N-(2’-propinyl)-6-methylergoline-8β-carboxamide D-lysergic acid.
Ručman does not, however, disclose structures listed in claim 26.
Grill teaches the structure L2, which reads on compound 12a, a novel derivative for the purposes of metabolite identification in a human liver microsome assay (pg. 41):
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While Grill illustrates the racemic structure, they also describe optimizing the isomer output (pg. 32 – Example 2: isomer optimization). It is therefore reasonable to conclude that all isomers could have been obtained, including 12a, by their described means or by more traditional means such as chiral HPLC separation.
As such, it would have been prima facie obvious, to a person of ordinary skill in the art, before the effective filing date, to have been informed about structure 12a, as taught by Grill.
Allowable Subject Matter
Claims 21, 28 and 35 would be allowable if rewritten to overcome the rejection(s) under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), 2nd paragraph, set forth in this Office action and to include all of the limitations of the base claim and any intervening claims.
Reasons For Allowance
The following is an examiner’s statement of reasons for allowance: the following is a statement of reason for the indication of allowable subject matter: structure as defined by 16b were not taught in the prior art in a 100% embodiment The closest matches are structures as disclosed by Ručman et al. (Ergoline derivatives of 1-propinylamine, a process for the manufacture thereof and the use thereof for medicaments, 5,480,885, 1996), M. Grill (Improved method for the production of lysergic acid diethylamide (LSD) and novel derivatives thereof, WO 2022/008627 A2, 13 January 2022), and Niwaguchi et al. (Studies on lysergic acid diethylamide and related compounds. IV. Syntheses of various amide derivatives of norlysergic acid and related compounds, Yakugaku Zasshi 1976, 96, 5, 673-678) as described by structure IV- example 1, L2, and 34, respectively:
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Furthermore, the art does not read upon the limitations of claim 21, where R6 is C3-C7 alkenyl substituted with one or more F, further optionally substituted with one or more CN, OH and/or =O, wherein the C=C double bond is not adjacent to N, as no art was found to contain the geminal-F substitution on the pendant alkene.
Therefore, the prior art neither anticipates nor reasonably makes obvious the claimed invention and therefore, the claimed invention is deemed novel and unobvious over the prior art.
Any comments considered necessary by applicant must be submitted no later than the payment of the issue fee and, to avoid processing delays, should preferably accompany the issue fee. Such submissions should be clearly labeled “Comments on Statement of Reasons for Allowance.”
Summary
Claims 19 and 26 are objected to. Claims 21, 28 and 35 are objected as being allowable but dependent upon a rejected base claim. Claims 17-19 and 24-25 are rejected under 35 U.S.C. 102(a)(1) and 35 U.S.C. 102(a)(2). Claim 26 is rejected under 35 U.S.C. 103.
Conclusion
Claims 19, 21, 26, 28 and 35 are objected to. Claims 17-19 and 24-26 are rejected.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Allen Chao whose telephone number is (571)272-7001. The examiner can normally be reached Monday - Friday 0700-1300.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, James H Alstrum-Acevedo can be reached at 571-272-5548. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/ALLEN CHAO/Examiner, Art Unit 1622
/JAMES H ALSTRUM-ACEVEDO/Supervisory Patent Examiner, Art Unit 1622