DETAILED ACTION
Claims 1-22 and 26 are pending.
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 .
Priority
The instant application filed 11/10/2023 is a National Stage entry of PCT/US2022/028797, with an International Filing Date of 5/11/2022. PCT/US2022/028797 claims Priority from Provisional Application 63186988, filed 5/11/2021.
Information Disclosure Statement
The Information Disclosure Statement (IDS) submitted on 9/3/2025 is in compliance with the provisions of 37 CFR 1.97. Accordingly, the Information Disclosure Statement is being considered by the Examiner.
Claim Rejections - 35 USC § 112(b) and (d)
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 1 and 5 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 5 recites the limitation "R6." There is insufficient antecedent basis for this limitation in the claim as claim 1 doesn’t include "R6" in the claim. Claim 5 would need to refer to claim 13, in which the "R6" limitation is introduced.
And….
The following is a quotation of 35 U.S.C. 112(d):
(d) REFERENCE IN DEPENDENT FORMS.—Subject to subsection (e), a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
The following is a quotation of pre-AIA 35 U.S.C. 112, fourth paragraph:
Subject to the following paragraph [i.e., the fifth paragraph of pre-AIA 35 U.S.C. 112], a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
Claims 1 and 5 are rejected under 35 U.S.C. 112(d) or pre-AIA 35 U.S.C. 112, 4th paragraph, as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends. Claim 5 cannot further limit a term not introduced, "R6." Applicant may cancel the claim(s), amend the claim(s) to place the claim(s) in proper dependent form, rewrite the claim(s) in independent form, or present a sufficient showing that the dependent claim(s) complies with the statutory requirements.
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.
Claims 1-10, 13, 16, and 18 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Eshleman et al. “Neurochemical pharmacology of psychoactive substituted N-benzylphenethylamines: High potency agonists at 5-HT2A receptors,” Biochemical Pharmacology 158 (2018) 27–34 published 9/25/2018.
Claims 1-10, 12, 16, and 18-19 are directed towards Compound 4, 25N-NBOMe (see instant claim 18 and the Figure below).
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Note: in this Figure, given the symmetrical nature of the Left Ring and its ability to rotate, this molecule is defined as:
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R1 = R5 = OMe
R2 = R4 = H
R3 = R3 = NO2
R4 = R2 = OMe
R5 = R1 = H.
Eshleman teaches this exact compound, see page 28. Eshleman teaches the compound having the same name and same structure, 25N-NBOMe. Eshleman teaches these compounds as having neurochemical pharmacology, and had very high affinity for, and full efficacy at, 5-HT2A and 5-HT2C receptors.
Therefore claims 1-10, 13, 16, and 18 are anticipated.
Claim Rejections - 35 USC § 102
In regards to claim 11 and 12.
Claims 1 and 11-12 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Hansen et al. “Synthesis and pharmacological evaluation of N-benzyl substituted 4-bromo-2,5-dimethoxyphenethylamines as 5-HT2A/2C partial agonists,” Bioorganic & Medicinal Chemistry 23 (2015) 3933–3937 published 2015.
Claim 11 and 12 are drawn to chemical compounds with the general structure of claim 1:
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And where in A is a bicyclic or tricyclic structure.
Hansen teaches:
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These compounds meet the limitations of claims 1, 11, 12 and therefore anticipated the instant claims.
Claim Rejections - 35 USC § 102
In regards to claim 14.
Claims 1 and 13-14 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Mai et al. Eur J Med Chem (1995) 30, 593-601 published in 1995.
Claims 13 and 14 are drawn to chemical compounds with the general structure of claim 1:
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And where in A is:
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And where R6 is a 5-10 membered heteroaryl.
Mai shows structure 8 as:
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When X and W are MeO the compound is 8f, this compound anticipates claims 1 and 13-14.
Claim Rejections - 35 USC § 102
In regards to claim 17.
Claims 1, 13, and 17 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Blaazer et al. “Structure–Activity Relationships of Phenylalkylamines as Agonist Ligands for 5-HT2A Receptors,” Chem Med Chem 2008, 3, 1299 – 1309.
Claims 13 and 17 are drawn to chemical compounds with the general structure of claim 1:
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And where in A is:
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And where R6 and R7 can be H, and R8 is selected from a large group of substituents.
Blaazer teaches:
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Compound 30 meets all the limitations of claims 1, 13, and 17 and are therefore anticipated.
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 nonobviousness.
Claims 1-10, 13, 16, and 18-21 are rejected under 35 U.S.C. 103 as being unpatentable Eshleman et al. “Neurochemical pharmacology of psychoactive substituted N-benzylphenethylamines: High potency agonists at 5-HT2A receptors,” Biochemical Pharmacology 158 (2018) 27–34 published 9/25/2018, in view of Fuentes et al. “Therapeutic Use of LSD in Psychiatry: A Systematic Review of Randomized-Controlled Clinical Trials,” Front Psychiatry 2020 Jan 21;10:943.
Claims 1-10, 12, 16, and 18-19 are directed towards Compound 4, 25N-NBOMe (see instant claim 18 and the Figure below).
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Note: in this Figure, given the symmetrical nature of the Left Ring and its ability to rotate, this molecule is defined as:
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R1 = R5 = OMe
R2 = R4 = H
R3 = R3 = NO2
R4 = R2 = OMe
R5 = R1 = H.
Instant claims 20-22 and 26 are directed to methods of using these compounds as pharmaceutical agents and in the treatment of disease including anxiety disorders.
Eshleman teaches this exact compound, see page 28. Eshleman teaches the compound having the same name and same structure, 25N-NBOMe. Eshleman teaches these compounds as having neurochemical pharmacology, and had very high affinity for, and full efficacy at, 5-HT2A and 5-HT2C receptors.
Fuentes teaches that LSD a 5-HT2A agonist is used in the clinic for several treatments. Fuentes states the evidence to date is strongest for the use of LSD in the treatment of alcoholism. Fuentes also shows positive evidence for the use of LSD in Anxiety, Depression, and Psychosomatic Diseases. Fuentes teaches, “However, LSD remains one of the most stigmatized and legally restricted agents among psychoactive substances.”
A person of ordinary skill in the art would look to substitute LSD with the synthetic drugs of Eshleman to avoid the “recreational” view of LSD in the public thereby providing the same benefits of LSD without the negative stereotype of the recreational drug. Simple substitution of one drug for the other having the same mechanism of action would result in the same effect, as is seen when one substitutes atorvastatin with lovastatin, they both lower cholesterol levels regardless of their different structures. Therefore the claims (claims 1-10, 12, 16, 18-21) directed to a method of using these compounds to treat disease (anxiety) are prima facia obvious at the time of filing.
Claim Rejections - 35 USC § 103
Claims 1-10, 13, 16, 18-22, and 26 are rejected under 35 U.S.C. 103 as being unpatentable Eshleman et al. “Neurochemical pharmacology of psychoactive substituted N-benzylphenethylamines: High potency agonists at 5-HT2A receptors,” Biochemical Pharmacology 158 (2018) 27–34 published 9/25/2018, in view of Fuentes et al. “Therapeutic Use of LSD in Psychiatry: A Systematic Review of Randomized-Controlled Clinical Trials,” Front Psychiatry 2020 Jan 21;10:943 as applied to claims 1-10, 13, 16, and 18-21 above in further view of Nichols US20100016280A1 published 1/21/2010.
Eshleman and Fuentes show the compounds of the instant invention are known in the art as 5-HT2A agonists and that they have similar properties to LSD and would be expected to work in diseases treated with this mechanism of action. They do not teach treatment of an inflammatory disorder as required by instant claim 22, and they so not teach also administering a hallucinogen, instant claim 26.
Nichols teaches the treatment of an inflammatory disorder by administering to a mammal in need of such treatment a therapeutically effective amount of a 5-HT2A receptor agonist in an amount no greater than that required to result in a body fluid concentration no greater than 5 nM in a pharmaceutically acceptable carrier. Nichols also teaches additional use of LSD in the treatment (Claim 8).
A person of ordinary skill in the art would look to use the known 5-HT2A agonist taught by Eshleman in the method of Nichols, as Nichols teaches the entire genus would treat the inflammatory disease. Therefore a prima facia case of obvious at the time of filing.is found as the genus is taught, of which includes the compounds of Eshleman.
Conclusion
No claims allowed.
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/MICHAEL J SCHMITT/Examiner, Art Unit 1629
/JEFFREY S LUNDGREN/Supervisory Patent Examiner, Art Unit 1629