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 the Claims
Currently, claims 1-30 are pending in the instant application. Claims 5-6, 14, 16, 18, 22-23, 26-27, and 30 are withdrawn from consideration in accordance with the Election Requirement. Claims 1-4, 7-13, 15, 17, 19-21, 24-25, and 28-29 are pending in the instant application.
Priority
The instant application is a CON of application 19/189,953 filed on 04/25/2025 and PCT/IB2024/000642 filed on 11/12/2024. The instant application claims priority to provisional applications 63/598,671 filed on 11/14/2023 and 63/598,711 filed on 11/14/2023.
Information Disclosure Statement
The information disclosure statement (IDS) submitted on 12/09/2025 and 06/05/2026 are in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statement is being considered by the examiner.
Election/Restrictions
Per the Election Requirement submitted on 04/09/2026, Applicant elected the following species:
A single compound of Formula (I): (R) I74 as recited in claim 21
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A single disease to be treated: Depression
Applicant indicates that the above elected species read on claims 1-4, 7-13, 15, 17, 19-21, 24-25, and 28-29. Accordingly, the aforementioned claims will be pending examination, and claims 5-6, 14, 16, 18, 22-23, 26-27, and 30 are hereby withdrawn from consideration.
Applicant’s elected compound appears to be free of the art. However, rejoinder is not currently appropriate as all claims applicable to the elected species are not in condition for allowance.
Claim Objections
Claim 10 is objected to because of the following informalities: Typographical error. Claim 10 recites “OfH”, but should recite “OH”. Appropriate correction is required.
Claims 19-20 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 § 112 – Second Paragraph
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claims 21 and 29 are rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
Claim 21 is indefinite for reciting the following compound species:
I-71
I-72
I-93
(R) I-94
Because a person of ordinary skill in the art would not reasonably be able to understand the metes and bounds of the claim. The above compounds appear to violate the provisos set forth in claim 1:
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With regards to I-71, R1-R5 and R7-R10 are each H, R6 is C1 alkyl and R11 (or R12) is C1 alkyl. With regards to I-72, R1-R5 and R7-R10 are each H, R6 is C1 alkyl and R11 (or R12) is H. With regards to I-93, R1-R5 and R7-R10 are each H, R6 is C3 alkyl, and R11 (or R12) is C1 alkyl. With regards to (R) I-94, R1-R5 and R7-R10 are each H, R6 is C3 alkyl, and R11 (or R12) is C1 alkyl. Accordingly, the aforementioned compounds provide improper antecedence to claim 1.
Claim 29 is indefinite for reciting the following provisos:
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Because a person of ordinary skill in the art would not reasonably be able to understand the metes and bounds of the claim. The instant claim provides that variables R11 and R12 combine to form a heterocyclic ring. Unlike in claim 1, the instant claim recites no limitations regarding variables R11 and R12 being individual moieties. Accordingly, the instant claim provides improper antecedence. This rejection may be overcome by removing the provisos.
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(s) 1-4 and 7-8 is/are rejected under 35 U.S.C. 102(a)(2) as being anticipated by Rashid (US 2024/0254081 A1).
Claim 1 recites a compound of Formula (I):
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Rashid teaches tryptamine analogs and methods of synthesizing such compounds. Among the compounds taught by Rashid is the following compound Example 32(v), 4-(2-(5-methoxy-1H-indol-3-yl)ethyl)morpholine (specification [0378]):
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The compound of Rashid anticipates a compound of Formula (I) wherein:
X is O
R1 is H
R2-R5 and R7-R10 are each H
R6 is C1 alkyl
R11 and R12 are come together with the intervening nitrogen to form a 6-membered heterocycle comprising an additional oxygen atom
Claim 2 further limits the compound of claim 1 wherein R6 is selected from C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₁-C₆alkyleneZR¹⁴, C₂-C₆alkenyleneZR¹⁴, C₂-C₆alkynyleneZR¹⁴, C₃-C₇cycloalkyl, C₃-C₁₀heterocycloalkyl, and C₁-C₄alkyleneC-C7cycloalky. the latter three groups being optionally substituted with one to four substituents independently selected from halo, C1-C₆alkyl, OR¹⁵, and C(O)R¹⁵, and wherein available hydrogen atoms of R², R⁴, R⁵, R⁶, R⁷ R⁸, R9, R¹⁰, R¹¹, R¹², R¹⁴, R¹⁵, R¹⁶, R¹⁷, R¹⁸, R¹⁹, and R²⁰ are optionally replaced with a fluorine atom and/or a chlorine atom and/or available hydrogen atoms of R¹, R², R³, R⁴, R⁵, R⁶, R⁷ R⁸, R9, R¹⁰, R¹¹, R¹², R¹⁴, R¹⁵, R¹⁶, R¹⁷, R¹⁸, R¹⁹, and R²⁰ are optionally replaced with deuterium.
The compound of Rashid is a compound of claim 1 wherein R6 is C1 alkyl.
Claim 3 further limits the compound of claim 1 wherein:
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The compound of Rashid is a compound of claim 1 wherein R7-R10 are each H.
Claim 4 further limits the compound of claim 1 wherein:
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The compound of Rashid is a compound of claim 1 wherein R7-R10 are each H.
Claim 7 further limits the compound of claim 1 wherein R¹¹ and R¹² are taken together with the nitrogen atom therebetween to form a monocyclic 3- to 7-membered heterocyclic ring optionally comprising 1 to 3 additional ring heteromoieties selected from O, S, S(O), SO₂, N, and NR¹⁸ and/or optionally comprising one or two C=O groups, wherein said monocyclic 3- to 7- membered heterocyclic ring is further optionally substituted with one to four substituents independently selected from halo, C₁-C₆alkyl, OH, OC1-C₆alkyl, C₁-C₆alkyleneOH, and C₁- CęalkyleneOC1-C6alkyl, wherein available hydrogen atoms of R², R⁴, R⁵, R⁶, R⁷ R⁸, R9, R¹⁰, R¹¹, R¹², R¹⁴, R¹⁵, R¹⁶, R¹⁷, R¹⁸, R¹⁹, and R²⁰ are optionally replaced with a halogen atom and/or available hydrogen atoms of R¹, R², R³, R⁴, R⁵, R⁶, R⁷ R⁸, R9, R¹⁰, R¹¹, R¹², R¹⁴, R¹⁵, R¹⁶, R¹⁷, R¹⁸, R¹⁹, and R²⁰ are optionally replaced with deuterium.
The compound of Rashid is a compound of claim 1 wherein R11 and R12 come together with the intervening nitrogen to form a 6-membered heterocycle with an additional oxygen heteroatom.
Claim 8 further limits the compound of claim 1 wherein R¹¹ and R¹² are taken together with the nitrogen atom therebetween to form a monocyclic 3- to 7-membered heterocyclic ring, wherein said monocyclic 3- to 7-membered heterocyclic ring is further optionally substituted with one to four substituents independently selected from halo, C₁-C₆alkyl, OH, OC1-C6alkyl, C1- C₆alkyleneOH, and wherein available hydrogen atoms of R², R⁴, R⁵, R⁶, R⁷ R⁸, R9, R¹⁰, R¹¹, R¹², R¹⁴, R¹⁵, R¹⁶, R¹⁷, R¹⁸, R¹⁹, and R²⁰ are optionally replaced with a halogen atom and/or available hydrogen atoms of R¹, R², R³, R⁴, R⁵, R⁶, R⁷ R⁸, R9, R¹⁰, R¹¹, R¹², R¹⁴, R¹⁵, R¹⁶, R¹⁷, R¹⁸, R¹⁹, and R²⁰ are optionally replaced with deuterium.
Rashid teaches the following compound 32(iv) 5-methoxy-3-(2-(pyrrolidin-1-yl) ethyl)-1H-indole (specification [0377]):
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The above compound meets the limitations of the instant claim wherein R11 and R12 come together to form a 5-membered heterocycle.
Claim(s) 9 and 1 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Klein (JPET 337:860–867, 2011).
Claim 9 further limits the compound of claim 1 wherein R¹¹ and R¹² are taken together with the nitrogen atom therebetween to form a monocyclic 3- to 7-membered heterocyclic ring including at least one substituent selected from OH, OC₁-C₄alkyl, OC₁-C₄deuteroalkyl, OC1-C,fluoroalkyl, OC₁-C4deuterofluoroalkyl, C₁-C₄alkyleneOH, C₁-C₄fluoroalkyleneOH, C₁- C₄deuteroalkyleneOH, C₁-C₄deuterofluoroalkyleneOH, C1-C4alkyleneOC1-Calkyl, C1- C₄alkyleneOC1-C4fluoroalkyl, C₁-C4alkyleneOC₁-C₄deuteroalkyl, C₁-C₄alkyleneOC₁- C₄deuterofluoroalkyl, C₁-C₄fluoroalkyleneOC₁-C4alkyl, C₁-C₄deuteroalkyleneOC1-C4alkyI, C₁-C4deuterofluoroalkyleneOC1-CalkyI, C₁-C₄fluoroalkyleneOC+-C4fluoroalkyl, C1- C₄fluoroalkyleneOC1-C4deuteroalkyl, C₁-C4deuteroalkyleneOC1-C4fluoroalkyl, C₁- C4deuteroalkyleneOC1-C&deuteroalkyl, C-C4deuterofluoroalkyleneOC+-Cafluoroalkyl C1- C4fluoroalkyleneOC-C4deuterofluoroalkyl, and C₁-C4deuterofluoroalkyleneOC- C4deuterofluoroalkyl, and wherein available hydrogen atoms of R², R⁴, R⁵, R⁶, R⁷ R⁸, R9, R¹⁰, R¹¹, R¹², R¹⁴, R¹⁵, R¹⁶, R¹⁷, R¹⁸, R¹⁹, and R²⁰ are optionally replaced with a halogen atom and/or available hydrogen atoms of R¹, R², R³, R⁴, R⁵, R⁶, R⁷ R⁸, R9, R¹⁰, R¹¹, R¹², R¹⁴, R¹⁵, R¹⁶, R¹⁷, R¹⁸, R¹⁹, and R²⁰ are optionally replaced with deuterium.
Klein teaches compounds as tryptamine analogs and methods of making said analogs. Of particular relevance to the instant claims is the following compound 12 (page 862, Fig. 1):
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The above compound anticipates a compound of the instant claim and claim 1 wherein:
X is O
R1-R10 are each H
R11 and R12 come together with the intervening nitrogen to form a 6-membered heterocycle substituted with two methyl groups
Claim(s) 10-13 is/are rejected under 35 U.S.C. 102(a)(2) as being anticipated by Rashid.
Claim 10 further limits the compound of claim 1 wherein R¹¹ and R¹² are taken together with the nitrogen atom therebetween to form a monocyclic 3- to 7-membered heterocyclic ring selected from aziridinyl, azetidinyl, diazetidinyl, pyrrolidinyl, imidazolidinyl, pyrazolidinyl, piperidinyl, piperazinyl, tetrahydropyridinyl, morpholinyl, 2-oxopiperazinyl, 2-oxopiperidinyl, 2- oxopyrrolidinyl, piperidinyl, piperazinyl, thiomorpholinyl, thiomorpholinyl sulfoxide, thiomorpholinyl dioxide, azepanyl, diazepanyl, and 2,5-pyrrolidinedionyl, each of which is optionally substituted with one to four substituents independently selected from halo, C1-C₆alkyl, OH, OC1-C₆alkyl, C₁-C₆alkyleneOH, and wherein available hydrogen atoms of R², R⁴, R⁵, R⁶, R⁷ R⁸, R9, R¹⁰, R¹¹, R¹², R¹⁴, R¹⁵, R¹⁶, R¹⁷, R¹⁸, R¹⁹, and R²⁰ are optionally replaced with a halogen atom and/or available hydrogen atoms of R¹, R², R³, R⁴, R⁵, R⁶, R⁷ R⁸, R9, R¹⁰, R¹¹, R¹², R¹⁴, R¹⁵, R¹⁶, R¹⁷, R¹⁸, R¹⁹, and R²⁰ are optionally replaced with deuterium.
Compound 32(v) of Rashid provides a compound wherein R11 and R12 come together to form a morpholinyl moiety.
Claim 11 further limits the compound of claim 1 wherein R⁶ is selected from H, C₁-C₁₀alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₁-C₆alkyleneZR¹⁴, C₂-C₆alkenyleneZR¹⁴, C₂-C₆alkynyleneZR14, C₃- C₇cycloalkyl, C₃-C₁₀heterocycloalkyl, C₁-CśalkyleneC₃-Ccycloalky. and C₁-CealkyleneC₃- C₁₀heterocycloalkyl, the latter four groups being optionally substituted with one to four substituents independently selected from halo, C₁-C₆alkyl, OR¹⁵, and C(O)R¹⁵.
Compound 32(v) of Rashid is a compound wherein R6 is C1 alkyl.
Claim 12 further limits he compound of claim 1 wherein R6 is selected from:
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Compound 32(v) of Rashid is a compound of Formula (I) wherein R6 is CH3.
Claim 13 further limits the compound of claim 1 wherein R6 is selected from :
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Compound 32(v) of Rashid is a compound of Formula (I) wherein R6 is CH3.
Claim(s) 15 and 1 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by CAS Registry Number 363590-48-1 (Entered 21 Oct 2001).
Claim 15 further limits the compound of claim 1 wherein R11 and R12 form a ring selected from:
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CAS Registry Number 363590-48-1 is represented by the following structure:
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The above compound anticipates a compound of Formula (I) wherein:
X is O
R1-R5 and R7-R10 are each H
R6 is CH3
R11 and R12 come together to form
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Claim(s) 17, 24-25, and 28-29 is/are rejected under 35 U.S.C. 102(a)(2) as being anticipated by Rashid.
Claim 17 further limits the compound of claim 1 wherein:
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Compound 32(v) of Rashid is a compound of Formula (I) wherein:
R2 and R4-R10 are each H
R6 is C1 alkyl
R11 and R12 come together to form an unsubstituted 6-membered heterocycle
Claim 24 recites a pharmaceutical composition comprising one or more compounds of claim 1 and a pharmaceutically acceptable carrier.
The teachings of Rashid are also drawn towards compositions comprising the disclosed compounds (specification [0043])1.
Claim 25 recites a method of treating a mental illness, comprising administering a therapeutically effective amount of one or more compounds of claim 1 to a subject in need thereof, wherein the mental illness is selected from anxiety disorders, generalized anxiety disorder, social anxiety disorder, depression, cancer-related depression, major depressive disorder (MDD), treatment-resistant depression (TRD), postpartum depression (PPD), anxiety, alcohol addiction, drug addiction, opioid addiction, obsessive-compulsive disorder (OCD), post- traumatic stress disorder (PTSD), and combinations thereof.
Rashid indicates the use of tryptamine analogs in the treatment of major depressive disorders (specification [0008])2.
Claim 28 recites a compound of Formula (I):
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Rashid teaches tryptamine analogs and methods of synthesizing such compounds. Among the compounds taught by Rashid is the following compound Example 32(v), 4-(2-(5-methoxy-1H-indol-3-yl)ethyl)morpholine (specification [0378]):
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The compound of Rashid anticipates a compound of Formula (I) wherein:
X is O
R1 is H
R2-R5 and R7-R10 are each H
R6 is C1 alkyl
R11 and R12 are come together with the intervening nitrogen to form a 6-membered heterocycle comprising an additional oxygen atom
Claim 29 recites a compound of Formula (I):
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Rashid teaches tryptamine analogs and methods of synthesizing such compounds. Among the compounds taught by Rashid is the following compound Example 32(v), 4-(2-(5-methoxy-1H-indol-3-yl)ethyl)morpholine (specification [0378]):
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The compound of Rashid anticipates a compound of Formula (I) wherein:
X is O
R1 is H
R2-R5 and R7-R10 are each H
R6 is C1 alkyl
R11 and R12 are come together with the intervening nitrogen to form a 6-membered heterocycle comprising an additional oxygen atom
Allowable Subject Matter
Claims 19-20 appear to provide allowable subject matter. Both claims appear to provide a genus of compounds not taught or suggested in the prior art. While the aforementioned claims may contain allowable subject matter, they are not in condition for allowance as they are dependent upon a rejected base claim (claim 1). As iterated previously, Applicant’s elected compound species (R) I74 appears to also be free of the art. Currently, independent claims 1, 28, and 29 look to encompass a fairly large number of compounds due to the shared structure of tryptamine analogs, in particular, where variable X is O. As allowable subject matter has been identified in the claims, the it is recommended that the claims be amended to focus on compound (R) I74, recited compounds having similar structure, and genus recited in claims 19-20 which encompass (R) I74.
Conclusion
Claims 1-4, 7-13, 15, 17, 21, 24-25, and 28-29 are rejected.
Claims 10 and 19-20 are objected to.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to ERIC TRAN whose telephone number is (571)272-7854. The examiner can normally be reached Mon-Fri 8:00-5:00.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Jeffrey S 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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/ERIC TRAN/Examiner, Art Unit 1629
/JEFFREY S LUNDGREN/Supervisory Patent Examiner, Art Unit 1629
1 “The present disclosure also includes compositions, methods of producing the compounds and compositions comprising the compounds of the invention, kits comprising any one or more of the components of the foregoing, optionally with instructions to make or use same and uses of any of the foregoing.”
2 “Natural and synthetic sources of these compounds and their analogues are used as psychedelic drugs. However, they also have medicinal therapeutic uses, and several are being investigated for treating psychiatric illnesses and disorders, opioid use disorders, alcohol use disorders, sleep deprivation, anxiety disorders, major depressive disorders, and cancer-related psychiatric distress”
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