DETAILED ACTION
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 Claims
Claims 1-8 are pending.
Priority
Instant application 18/707,089, filed 05/02/2024 claims priority as follows:
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Information Disclosure Statement
All references from IDS(s) received 08/21/2025, 02/13/2026, and 08/14/2026 have been considered unless marked with a strikethrough.
Election/Restrictions
Applicant’s election without traverse of Group I, claims 1-8 in the reply filed on 08/14/2026 is acknowledged. Non-elected claims 9, 11, 12, 14, 18-21, 29, and 31-33 have been canceled.
Claim Objections
Applicant is advised that should claim 1 be found allowable, claim 5 will be objected to under 37 CFR 1.75 as being a substantial duplicate thereof. Should claim 2 be found allowable, claim 6 will be objected to under 37 CFR 1.75 as being a substantial duplicate thereof. When two claims in an application are duplicates or else are so close in content that they both cover the same thing, despite a slight difference in wording, it is proper after allowing one claim to object to the other as being a substantial duplicate of the allowed claim. See MPEP § 608.01(m).
Claims 1 and 5 differ only by the preamble recitation “isolated” in claim 5. The preamble recitation “isolated” in claim 5 is not considered to meaningfully distinguish the content of claim 1 from claim 5, because the body of the claims recite the same compound of Formula (I) or a pharmaceutically acceptable salt thereof. Similarly, claim 2 depends from claim 1 and claim 6 depends from claim 5; both claims recite the compound of Formula (I) substantially free of a compound of Formula (II).
Claim Rejections - 35 USC § 112(b)
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 2 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.
The term “substantially” in claims 2 and 5 is a relative term which renders the claim indefinite. The term “substantially” 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.
The specification does not define the term “substantially” and does not provide sufficient guidance to indicate to the person of ordinary skill what level of purity renders a compound of Formula (I) “substantially free” of a compound of Formula (II). For example, if the compound of Formula (I) contains 40% of the compound of Formula (II), is it “substantially free” of Formula (II)? Or is a lower percentage of Formula (II) required? The person having ordinary skill cannot answer such questions because the specification and claims do not define the term and the specification does not provide a standard for ascertaining the requisite degree of the term “substantially”.
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.
Claims 1-8 are rejected under 35 U.S.C. 102(a)(2) as being anticipated by DONG (WO 2022081631 A1; cited in IDS, filed 13 October 2021).
The applied reference has a common applicant (THE REGENTS OF THE UNIVERSITY OF CALIFORNIA) and joint inventor (OLSON) with the instant application, but also names other joint inventors (DONG, LY, TIAN) not listed on the instant application. Based upon the earlier effectively filed date of the reference, it constitutes prior art under 35 U.S.C. 102(a)(2). This rejection under 35 U.S.C. 102(a)(2) might be overcome by: (1) a showing under 37 CFR 1.130(a) that the subject matter disclosed in the reference was obtained directly or indirectly from the inventor or a joint inventor of this application and is thus not prior art in accordance with 35 U.S.C. 102(b)(2)(A); (2) a showing under 37 CFR 1.130(b) of a prior public disclosure under 35 U.S.C. 102(b)(2)(B) if the same invention is not being claimed; or (3) a statement pursuant to 35 U.S.C. 102(b)(2)(C) establishing that, not later than the effective filing date of the claimed invention, the subject matter disclosed in the reference and the claimed invention were either owned by the same person or subject to an obligation of assignment to the same person or subject to a joint research agreement.
The instant claims are drawn to compounds of Formula I and Formula II, which are the (R)- and (S)-enantiomers of the compound 3,4-methylenedioxydimethylamphetamine, respectively.
Dong discloses a GPCR screening method to identify non-hallucinogenic compounds (title, abstract). In Example 2, Dong discloses the compounds screened. Dong discloses that “All enantiopure…methylenedioxymethamphet-amines (i.e., MDA, MDMA, MDDMA) were prepared using methodology described by Nenajdenko” (page 55, lines 5-7). Dong additionally discloses that “All amphetamine and methylenedioxyamphet-amine derivatives were prepared as the 1:1 fumarate salts with the exception of R- and S-MDMA, which were prepared as the 2:1 fumarate salts” (page 55, lines 12-15). Dong also discloses the definition of the abbreviations (R)-MDDMA and (S)-MDDMA on page 53 as referring to (R)- 3,4-methylenedioxydimethylamphetamine and (S)-3,4-methylenedioxydimethylamphetamine, respectively. Finally, Dong provides evidence that the individual enantiomers (R)-MDDMA and (S)-MDDMA were prepared and tested (as the 1:1 fumarate salts, as explained on page 55, lines 12-15). See the test data for each of (R)-MDDMA and (S)-MDDMA in Dong’s FIG. 2.
With respect to claims 1-6, Dong anticipates these claims because Dong discloses the preparation and testing of enantiopure (R)-MDDMA as the fumarate salt (see page 55, lines 5-7; page 55, lines 12-15; and FIG. 2).
With respect to claims 7-8, Dong anticipates these claims because Dong discloses the preparation and testing of enantiopure (R)-MDDMA as the fumarate salt (see page 55, lines 5-7; page 55, lines 12-15; and FIG. 2). With respect to the limitations reciting that Formula II is present in an amount of less than 10% or 1%, Dong discloses that the methylenedioxymethamphetamines prepared (which includes the (R)-MDDMA prepared in Dong) were determined to be enantiomerically pure (>99% ee) by chiral HPLC (page 55, lines 10-11).
Therefore, Dong anticipates claims 1-8.
Claims 1-2 and 5-6 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by HUANG (Electrophoresis, vol. 26, no. 20, Oct. 2005, pp. 3904–09; cited in IDS).
The instant claims are drawn to compounds of Formula I and Formula II, which are the (R)- and (S)-enantiomers of the compound 3,4-methylenedioxydimethylamphetamine, respectively.
Huang discloses the compound of Formula I, referred to in Huang as (R)-DMMDA (see FIG. 1A, showing the structure of DMMDA; and page 3908, left side, first para., disclosing (R)-DMMDA).
With respect to claims 1-2 and 5-6, Huang anticipates these claims because Huang discloses the preparation and isolation of (R)-DMMDA from its (S)-enantiomer.
Claims 1-8 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by DONG (Cell, vol. 184, no. 10, May 2021, pp. 2779-2792.e18; cited in IDS, published online 28 April 2021).
The instant claims are drawn to compounds of Formula I and Formula II, which are the (R)- and (S)-enantiomers of the compound 3,4-methylenedioxydimethylamphetamine, respectively.
Dong discloses a GPCR screening method to identify non-hallucinogenic compounds (title, abstract). In Example 2, Dong discloses the compounds screened. Dong discloses that “All enantiopure…methylenedioxymethamphet-amines (i.e., MDA, MDMA, MDDMA) were prepared using methodology described by Nenajdenko” (page e5, lines 3-5). Dong additionally discloses that “All amphetamine and methylenedioxyamphet-amine derivatives were prepared as the 1:1 fumarate salts with the exception of R- and S-MDMA, which were prepared as the 2:1 fumarate salts” (page e5, lines 8-10). Dong also discloses the definition of the abbreviations (R)-MDDMA and (S)-MDDMA on page e4 as referring to (R)- 3,4-methylenedioxydimethylamphetamine and (S)-3,4-methylenedioxydimethylamphetamine, respectively. Finally, Dong provides evidence that the individual enantiomers (R)-MDDMA and (S)-MDDMA were prepared and tested (as the 1:1 fumarate salts, as explained on page e5, lines 8-10). See the test data for each of (R)-MDDMA and (S)-MDDMA in Dong’s FIG. 4E and FIG. S4B.
With respect to claims 1-6, Dong anticipates these claims because Dong discloses the preparation and testing of enantiopure (R)-MDDMA as the fumarate salt (page e5, lines 3-5; page e5, lines 8-10; FIG. 4; and FIG. S4B).
With respect to claims 7-8, Dong anticipates these claims because Dong discloses the preparation and testing of enantiopure (R)-MDDMA as the fumarate salt (see page e5, lines 3-5; page e5, lines 8-10; FIG. 4; and FIG. S4B). With respect to the limitations reciting that Formula II is present in an amount of less than 10% or 1%, Dong discloses that the methylenedioxymethamphetamines prepared (which includes the (R)-MDDMA prepared in Dong) were determined to be enantiomerically pure (>99% ee) by chiral HPLC (page e5, lines 6-7).
Therefore, Dong anticipates claims 1-8.
Conclusion
Claims 1-8 are rejected.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Kyle Nottingham whose telephone number is (571)270-0640. The examiner can normally be reached M-F from 10:00 am - 6:00 pm.
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/K.N./Examiner, Art Unit 1621
/CLINTON A BROOKS/Supervisory Patent Examiner, Art Unit 1621
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