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 present application claims priority to the applications 63/186,497 and PCT/CA2022/050753, with effective filing dates of 10 May 2021 and 10 May 2022, respectively.
Claim Status
This Office Action is in response to Applicant’s Response to Restriction Requirement filed, 24 July 2026.
Applicant’s election of
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(Formula 1a) in the reply filed on 24 July 2026 is acknowledged. Because applicant did not distinctly and specifically point out the supposed errors in the restriction requirement, the election has been treated as an election without traverse (MPEP § 818.01(a)).
Claims 2-61 and 66-67 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected species, there being no allowable generic or linking claim. Claim 2 recites that the PS is psilocybin, which does not read on the elected species. Claim 3 depends upon claim 2, which does not read on the elected species. Claims 4-11 recite a compound that is Formula 1b – 1i, which does not read on the elected species. Claim 12 recites that the PS is psilocybin, which does not read on the elected species. Claims 13-21 recite a compound that is Formula 2a – 2i, which does not read on the elected species. Claim 22 recites that the PS is psilocybin, which does not read on the elected species. Claims 23-31 recite a compound that is Formula 3a – 3i, which does not read on the elected species. Claim 32 recites that the PS is psilocybin, which does not read on the elected species. Claims 33-41 recite a compound that is Formula 4a – 4i, which does not read on the elected species. Claim 42 recites that the PS is psilocybin, which does not read on the elected species. Claims 43-51 recite a compound that is Formula 5a – 5i, which does not read on the elected species. Claim 52 recites that the PS is psilocybin, which does not read on the elected species. Claims 53-61 recite a compound that is Formula 6a – 6i, which does not read on the elected species. Claim 66 recites one or more halogen groups are added to the carbon backbone of the spacer, which does not read on the elected species. Claim 67 recites that one or more alkyl groups are added to the carbon are added to the carbon backbone of the space, which does not read on the elected species.
Claims 1 and 62-65 are under consideration in the instant office action.
Claim Interpretation
The Examiner notes that claim 1 recites that DR is an additive or synergistic compound. Because “DR” and “additive or synergistic compound” is not further defined in the specification, the Examiner interprets an additive or synergistic compound to be any chemical matter.
Claim Objections
1. Claim 1 is objected to because of the following informalities: “or a relate phosphorylated mushroom alkaloid,” which should be “or a related phosphorylated mushroom alkaloid.”
Appropriate correction is required.
Claim Rejections - 35 USC § 112
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.
2. Claim 1 and 62-65 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 1 recites “DR is an additive or synergistic compound,” which is a relative term and renders the claim indefinite. The term “additive or synergistic compound” is not defined by the claim, the specification does not provide a standard for ascertaining the requisite degree, and one of ordinary skill in the art would not be reasonably apprised of the scope of the invention. Accordingly, it is ambiguous as to the exact scope that Applicant considers part of the claim invention and what degree of similarity would infringe. However, the Examiner notes that the application identifies a listing of additive or synergistic compounds in an embodiment ([0011]). Accordingly, Applicant can overcome this rejection by explicitly reciting one or more of these compounds from paragraph [0011] in claim 1.
Additionally, claim 1 recites “a related phosphorylated mushroom alkaloid,” which is a relative term and renders the claim indefinite. The term “a related phosphorylated mushroom alkaloid” is not defined by the claim, the specification does not provide a standard for ascertaining the requisite degree, and one of ordinary skill in the art would not be reasonably apprised of the scope of the invention. Accordingly, it is ambiguous as to the exact scope that Applicant considers part of the claim invention and what degree of similarity would infringe. However, the Examiner notes that the application identifies a listing of related mushroom alkaloids in an embodiment ([0009]; [0010]). Accordingly, Applicant can overcome this rejection by explicitly reciting one or more of these compounds from paragraphs [0009] or [0010] in claim 1.
Dependent claims 62-65 are included for depending on a rejected claim and not reciting limitations that resolve the ambiguity.
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.
3. Claim(s) 1* is rejected under 35 U.S.C. 102(a)(1) and 102(a)(2) as being anticipated by Londesbrough (U.S. Patent No. 10,519,175, issued 31 Dec 2019; of record, see PTO-892 mailed 24 Feb 2026).
*While Applicant elected a compound of Formula (I) (
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), Londesbrough applies to the broader genus, and thus the rejection over the broader genus is made in favor of compact prosecution. However, the Examiner notes that the full genus was not searched.
Londesbrough teaches psilocybin derivatives, such as the compound
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(Table 7, column 15). Mapping shown below:
18/560,206 Formula 4 components
18/560,206 Formula 4
Compound (Londesbrough)
PS
psilocin
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X
phosphate
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spacer
Unsubstituted linear chain
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18
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DR
An additive or synergistic compound
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The Examiner notes that benzyl is -CH2-phenyl (-spacer-DR).
Regarding claim 1, Londesbrough teaches
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(Table 7, column 15), which falls into Formula 4.
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.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
4. Claim(s) 1 and 62-65 are rejected under 35 U.S.C. 103 as being unpatentable over Kucuksen (US 2019/0350949, published 21 Nov 2019) in view of Lowe (“Two! Two! Two Drugs in One!” In the Pipeline, 2009, <www.science.org/content/blog-post/two-two-two-drugs-one>, accessed 26 Aug 2026), Zuravka (Bioorg. Med. Chem., 2015, 23, 1241-1250), and Ghosh (J. Med. Chem.¸2015, 658, 2895-2940).
Kucuksen teaches combining cannabinoids and/or terpenes with psilocybin and/or psilocin to treat or prevent psychological or brain disorders (abstract). Kucuksen specifically teaches cannabidiol (CBD) as one of the cannabinoids (abstract). Kucuksen teaches that people with a depressed mood can feel sad, anxious, empty, hopeless, helpless, worthless, guilty, irritable, angry, ashamed, or restless and that depressed mood is a feature and main symptom of some psychiatric syndromes ([0004]; [0006]). Kucuksen teaches that psilocybin is a naturally occurring psychedelic compound and is rapidly metabolized to psilocin in situ, which then acts on serotonin receptors in the brain ([0036]; [0037]). Kucuksen teaches that psilocybin and derivatives are serotonergic psychedelic substances and that both psilocin and psilocybin are present in psychedelic mushrooms together ([0038]). Kucuksen teaches that cannabinoids activate cannabinoid receptors in cells, such as CBD, and that cannabinoids have been suggested to be neuroprotective agents via antagonism of NMDA or reducing the influx of calcium ions into the cell ([0041]; [0044]; [0045]). Kucuksen teaches treating 50 subjects suffering from diverse medical conditions with a daily oral dose of combined treatment of pure psilocybin (30 mg) + pure CBD (30 mg), which then would be metabolized to psilocin in situ (Example 1, [0192]-[0195]; [0036]).
Regarding claim 1, Kucuksen fails to teach a psilocin and CBD conjugate.
Lowe teaches that combining two drugs into one conjugate in the field of drug discovery (page 1, paragraphs 1-2). Lowe teaches that one of the ideas underscoring creating a conjugate of two drugs is that two different agents will have different absorption and PK, whereas the conjugate will be coming on all at the same time, which is an advantage (page 1, paragraph 3). Lowe also teaches that compounds with the established SAR (e.g. psilocin and CBD) have an advantage as to inactive moieties in the compounds, which are primed to act as anchors for the linker between the two compounds (page 1, paragraph 5). Additionally, Lowe teaches the possibility of a conjugate of two known drugs being able to dodge resistance (page 1, paragraph 4).
Zuravka teaches linking known anticancer drugs to circumvent emerging resistance to the antitumor drugs (page 1241, column 1, paragraph 1). Zuravka teaches that alkylating agents, such as nitrogen mustards, are still commonly used chemotherapeutics and are prime for nucleophilic attack by DNA (page 1241, column 1, paragraph 1). Zuravka teaches that there is the emergence of resistance to this class of drugs and that there are efforts to develop more effective antitumor drugs (page 1241, column 1, paragraph 1). Zuravka teaches that the amino acid, lysine, is a suitable, flexible linker and that the carboxylic acid functionality of lysine provides a position at which the side chain can be modified (page 1242, column 1, paragraphs 3-4).
Ghosh teaches incorporation of carbamates (urethane) in medicinal chemistry (abstract). Ghosh specifies that carbamates are a key structural motif in many approved drugs and prodrugs and that drugs that utilize the carbamates functionality are designed as peptide surrogates (page 2895, column 1, paragraph 1).
It would have been prima facie obvious to one of ordinary skill in the art, prior to the effective filing date of the instantly claimed invention to simply combine CBD and psilocin in one compound as taught by Kucuksen, Lowe, and Zuravka with a lysine linker that connects via a carbamate as taught by Zuravka and Ghosh in order to simplify PK and circumvent potential acquired resistance to CBD or psilocin. One of ordinary skill in the art would have been motivated to make such a selection, with a reasonable expectation of success, because:
-Kucuksen teaches combining cannabinoids and/or terpenes with psilocybin and/or psilocin to treat or prevent psychological or brain disorders,
-Kucuksen specifically teaches cannabidiol (CBD) as one of the cannabinoids (abstract). Kucuksen teaches that people with a depressed mood can feel sad, anxious, empty, hopeless, helpless, worthless, guilty, irritable, angry, ashamed, or restless and that depressed mood is a feature and main symptom of some psychiatric syndromes,
-Kucuksen teaches that psilocybin is a naturally occurring psychedelic compound and is rapidly metabolized to psilocin in situ, which then acts on serotonin receptors in the brain,
-Kucuksen teaches that psilocybin and derivatives are serotonergic psychedelic substances and that both psilocin and psilocybin are present in psychedelic mushrooms together,
-Kucuksen teaches that cannabinoids activate cannabinoid receptors in cells, such as CBD, and that cannabinoids have been suggested to be neuroprotective agents via antagonism of NMDA or reducing the influx of calcium ions into the cell,
-Kucuksen teaches treating 50 subjects suffering from diverse medical conditions with a daily oral dose of combined treatment of pure psilocybin (30 mg) + pure CBD (30 mg), which then would be metabolized to psilocin in situ,
-Lowe teaches that combining two drugs into one conjugate in the field of drug discovery,
-Lowe teaches that one of the ideas underscoring creating a conjugate of two drugs is that two different agents will have different absorption and PK, whereas the conjugate will be coming on all at the same time, which is an advantage,
-Lowe also teaches that compounds with the established SAR (e.g. psilocin and CBD) have an advantage as to inactive moieties in the compounds, which are prime to act as anchors for the linker between the two compounds,
-Lowe teaches the possibility of a conjugate of two known drugs being able to dodge resistance,
-Zuravka teaches linking known anticancer drugs to circumvent emerging resistance to the antitumor drugs,
-Zuravka teaches that alkylating agents, such as nitrogen mustards, are still commonly used chemotherapeutics and are prime for nucleophilic attack by DNA,
-Zuravka teaches that there is the emergence of resistance to this class of drugs and that there are efforts to develop more effective antitumor drugs,
-Zuravka teaches that the amino acid, lysine, is a suitable, flexible linker and that the carboxylic acid functionality of lysine provides a position at which the side chain can be modified,
-Ghosh teaches incorporation of carbamates (urethane) in medicinal chemistry, and
-Ghosh specifies that carbamates are a key structural motif in many approved drugs and prodrugs and that drugs that utilize the carbamates functionality are designed as peptide surrogates.
Accordingly, the combination of Kucuksen, Lowe, Zuravka, and Ghosh teaches the compound,
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.
Regarding claim 62, Kucuksen teaches CBD, which is a cannabinoid (abstract; Example 1, [0192]-[0195]).
Regarding claim 63, Kucuksen teaches CBD, which is a cannabinoid (abstract; Example 1, [0192]-[0195]).
Regarding claim 64, Kucuksen teaches CBD, which is a cannabinoid (abstract; Example 1, [0192]-[0195]).
Regarding claim 65, Kucuksen teaches that the PS is psilocin ([0036]; Example 1, [0192]-[0195]).
Conclusion
No claim is allowed.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Madeline M Dekarske whose telephone number is (571)272-1789. The examiner can normally be reached Monday - Thursday 10am - 4pm.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, James 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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/MADELINE M. DEKARSKE/Examiner, Art Unit 1622
/JAMES H ALSTRUM-ACEVEDO/Supervisory Patent Examiner, Art Unit 1622
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