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
Election/Restriction
Applicant elected Group I invention, and nitrate salt of (R)-MDMA as the species, without traverse in the reply filed on 04/23/2026. Claims 1, 15-17, 28, 29, 51, and 53-59 read on the elected species. Claims drawn to non-elected salt species are cancelled.
Claim Status
Claims 1,15-17, 28-29, 51, and 53-59 are pending and currently under examination in this office action.
Priority
This instant application 18/401,401, filed on12/30/2023, claims benefit of US provisional application No. 63/436,531 filed 12/31/2022.
Information Disclosure Statement
The information disclosure statement filed 12/30/2025 and 04/23/2026 are in compliance with the provisions of 37 CFR1.97. The reference listed in IDS except cross-out are being considered by the Examiner.
Applicant filed about 40 pages of reference in IDS dated 08/07/2025 and IDS size fee is paid accordingly. However, the applicant has an obligation to call the most pertinent prior art to the attention of the U.S. Patent and Trademark Office in a proper fashion. Burying one reference in hundreds other IDS references is like citing nothing. PENN YAN BOATS, INC. v. SEA LARK BOATS, INC., et. al. 175 USPQ 260 (S.D. Fla. 1972). Golden Valley Microwave Foods, Inc. v. Weaver Popcorn Co. Inc., 24 USPQ2d 1801 (U.S. District Court Northern District of Indiana, July 22, 1992).
Claim Objections
Claims 55 and 56 are objected as being significantly duplicative claims. Claims 55 and 56 are not identical, but they are not patentably distinct from each other. Claim 55 recites the crystalline (R)-MDMA nitrate salt exhibits a DSC thermogram comprising an exothermic peak at 135±5 ºC. Claim 56 recites the crystalline (R)-MDMA nitrate salt exhibits a DSC thermogram comprising an endothermic peak at 136±5 ºC. Both claims 55 and 56 are directed to the same Differential Scanning Calorimetry (DSC) analysis of (R)-MDMA nitrate comprising the same endothermic peak.
The crystalline form of R-MDMA nitrate recited in claims 55 and 56 are not patentably distinct from each other in the absence of supporting evidence. Applicant is advised that should claim 55 be found allowable, claim 56 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).
Drawings
The amended drawings filed on 04/23/2026 is objected to under 37 CFR 1.83(a) because any amended replacement drawing sheet should include all of the figures appearing on the immediate prior version of the sheet, even if only one figure is being amended. Each drawing sheet submitted after the filing date of an application must be labeled in the top margin as either “Replacement Sheet” or “New Sheet” pursuant to 37 CFR 1.121(d). If the changes are not accepted by the examiner, the applicant will be notified and informed of any required corrective action in the next Office action. The objection to the drawings will not be held in abeyance.
Claim Interpretation
According to structural search, instant claimed (R)-3,4-methylenedioxymethamphetamine ((R)-MDMA) nitrate (CAS #3048205-90-6, entered in STN database on July 22, 2024).
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Please note the limitation of X-ray powder diffraction pattern peaks, DSC, TGA, melting point, etc. are properties of the crystalline form which are inseparable from the product itself. Once the crystalline salt form is obtained, XRPD, DSC and TGA of the crystalline form could be easily measured by a person of ordinary skilled in the art through routine method and general knowledge of crystallography.
Claim Rejections - 35 USC § 112
The following is a quotation of the first paragraph of 35 U.S.C. 112(a):
(a) IN GENERAL.—The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor or joint inventor of carrying out the invention.
The following is a quotation of the first paragraph of pre-AIA 35 U.S.C. 112:
The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor of carrying out his invention.
Claim 57 is rejected under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, as failing to comply with the written description requirement. The claim(s) contains subject matter which was not described in the specification in such a way as to reasonably convey to one skilled in the relevant art that the inventor or a joint inventor, or for applications subject to pre-AIA 35 U.S.C. 112, the inventor(s), at the time the application was filed, had possession of the claimed invention.
Claim 57 recites the crystalline (R)-MDMA nitrate salt exhibits a DSC thermogram comprising an exothermic peak at 136±5 ºC. There is no exothermic peak around 136±5 ºC as recited in claim 57 according to Fig. 14. Claim 56 and claim 57 reciting the crystalline (R)-MDMA nitrate salt exhibits a DSC thermogram comprising both endothermic peak and exothermic peak at 136±5 ºC is contradictory . Instant Spec(See PGPUB [0019] [0099], [0156]) discloses Nitrate Form A exhibits a DSC thermogram comprising an endothermic peak at 136±5° C. In embodiments, Nitrate Form A exhibits a DSC thermogram comprising an exothermic peak at 153±5° C. Instant specification does NOT support crystalline (R)-MDMA nitrate salt exhibit exothermic peak at 136±5 ºC.
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.
Claim 16 is rejected under 35 U.S.C. 112(b) as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor, regards as the invention.
Claim 16 recites crystalline salt having X-ray diffraction pattern “substantially similar to that shown in FIG. 4”. It is well recognized in the art that X-ray diffraction patterns may have different appearance due to artifacts and small differences in X-ray diffraction may be due to solvent, thus must be carefully evaluated for true new polymorphs. Without specifying the peak value, it is unclear what thresholds of each peak are used to determine whether a XRD pattern is “substantially similar to that shown in FIG. 4”. As stated in MPEP § 2173.05(s): “Where possible, claims are to be complete in themselves. Incorporation by reference to a specific figure or table "is permitted only in exceptional circumstances where there is no practical way to define the invention in words and where it is more concise to incorporate by reference than duplicating a drawing or table into the claim. Incorporation by reference is a necessity doctrine, not for applicant’s convenience." Ex parte Fressola, 27 USPQ2d 1608, 1609 (Bd. Pat. App. & Inter. 1993) (citations omitted)”.
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.
Claims 16-17, and 53-59 are rejected under 35 U.S.C. 112(d), 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. The claims recite properties of the R-MDMA nitrate crystalline in claim 15, e.g. XRPD peaks, DSC, etc. that do not further contribute to the structural limitation of a product or compound. See In re Best, 562 F.2d 1252; 195 USPQ 430 (CCPA, 1977), Titanium Metals Corp. v Banner, 778 F.2d 775 (Fed. Cir. 1985), Continental Can Co. v Monsanto Co., 948 F.2d 1264 (Fed. Cir. 1991), In re Cruciferous Sprout Litig., 301 F.3d 1343 (Fed. Cir. 2002), In re Crish, 393 F.3d 1253 (Fed. Cir. 2004). Therefore, they are improper dependent claims for failing to further limit the subject matter of claim 15.
Applicant may cancel the claim(s), amend the claim(s) to place the claim(s) in proper dependent 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 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 1,15, 28-29 and 51 are rejected under 35 U.S.C. 102(a)(2) as being anticipated by Duncton et al.( WO 2023092044 A2, Applicant’s IDS dated 12/30/2025, Cite # 022).
Regarding MDMA salt, Duncton discloses salts and solid forms (e.g. crystalline form/polymorph) of MDMA, (R)-MDMA, (S)-MDMA, etc., composition comprising aforementioned crystalline salt forms, and method for treating neurological disease and/or a psychiatric disorder in a subject (See abstract, page 2-3, page 4, para 2; Example 1-9; claims 1-110, 342-400). Duncton teaches variety salt for MDMA, (R)-MDMA, e.g. HCl, fumarate, tartrate, malate, etc. (See page 3, para 2; page 18, lines 9-26; page 21-49; Example 1-9 ;Tables 1-15; claims 1-110, 342-400). Duncton teaches (R)-MDMA salt may be formed from nitric acid which reads on instant (R)-MDMA nitrate salt (See page 18, line 22). Duncton teaches solid form of a (R)-MDMA salt may be a crystalline form /polymorph (See page 20, line 17-23). Duncton teaches the crystalline salt embodiments exhibit improved property, e.g. thermal stability, shelf life, solubility in water and/or organic solvents, bioavailability, absorption, etc. (See page 3, lines 1-5, 21-32).
Regarding claim 28-29 and 51, Duncton teaches pharmaceutical composition, comprising a solid form of a disclosed compound or a salt thereof, and a pharmaceutically acceptable excipient (See page 3, para 1; page 117-121; claims 367-368 and 391-392). Duncton teaches oral dosage form for oral administration (See page 117, line 11; page 121, line 10; claim 375).
Duncton collectively teaches composition comprising variety of crystalline forms salt (e.g. nitrate salt) of (R)-MDMA, thus, Duncton anticipates instant claimed invention.
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 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.
Claims 1,15-17, 28-29, 51,and 53-59 are rejected under 35 U.S.C. 103 as being unpatentable over Duncton et al.( WO 2023092044 A2, Applicant’s IDS dated 12/30/2025, Cite # 022).
The collective teaching of Duncton is elaborated in preceding 102 rejection and applied as before. Duncton collectively teaches variety of crystalline forms salt (e.g. nitrate salt) of (R)-MDMA, (S)-MDMA characterized by XRPD pattern, unit crystal cell parameter, DSC, TGA, etc.
Regarding limitations of claims 16-17 and 53, and 53-59, Duncton teaches property MDMA crystalline salt characterized by variety of spectrum, e.g. XRPD, DSC, TGA analysis (See Figures 1-116, Tables 2-15) . For example, Duncton teaches a solid crystalline form of MDMA tartrate Form I characterized by three or more XRPD signals (See Table 6, page 31), wherein 13.8, 15.7, 16.0, 18.0 ±0.2 θ read on XRPD peaks recited by instant claim 17 . Duncton teaches a solid crystalline form of MDMA tosylate characterized by three or more XRPD signals (See Table 11, page 41, lines 15-21), wherein 13.6, 15.4, 16.0, 18.1 ±0.2 θ also read on XRPD peaks recited by instant claim 17 .
Regarding claims 54-59, Duncton also teaches DSC, TGA analysis for MDMA salt and crystalline salt form(See page 596, lines 20-28; Figures 1-128): DSC data is used to evaluate melting point, thermal stability, and crystalline form conversion. TG data is used to evaluate if the API is a solvate or hydrate, and to evaluate thermal stability. DVS data is used to evaluate hygroscopicity of the API and if hydrates can be formed at high relative humidity, etc.. Duncton teaches single crystal X-ray structure determination technique to evaluate the monoclinic cell parameters of a crystalline form (See page 608, line 10-30; Table Ex 19-20; page 615). Please note the XRPD pattern, unit cell parameter, DSC, TGA, melting point, etc. are the properties of the crystalline salt which are inseparable from the product itself. Once the crystalline salt from is obtained, XRPD pattern, melting point, DSC, and other properties of the crystalline form could be easily measured by a person of ordinary skilled in the art through routine method and general knowledge of crystallization.
It is common practice for a skilled artisan to explore different salt form and crystalline form of active compound for purpose of stability, solubility and bioavailability etc. It would have been prima facie obvious to one of the ordinary skilled in the art before the effective filing date of instant invention to explore more crystalline salt forms of MDMA, (R)-MDMA taught by Duncton, together with experimentation/ optimization including salt screening, solvent selection, etc. based on general knowledge of crystallization and pharmaceutical formulation, and arrive at instantly claimed invention with reasonable expectation of success. A skilled artisan would be motivated to further explore different crystalline salt form of (R)-MDMA with reasonable expectation that alternative crystalline salt form of (R)-MDMA might provide improved chemical and physical properties, e.g. storage stability and solubility, etc.
It is a settled principle of law that a mere carrying forward of an original patented conception involving only change of form, proportions, or degree, or the substitution of equivalents doing the same thing as the original invention, by substantially the same means, is not such an invention as will sustain a patent, even though the changes of the kind may produce better results than prior inventions, See MPEP 2144.05 IIA. Instant claimed MDMA crystalline salt is considered as an obvious variation of MDMA salt taught by prior art.in the absence of evidence demonstrating the claimed crystalline form exhibits unexpected property/result relative to the MDMA salt taught by prior art.
One of ordinary skill in the art would have had reasonable expectation of success in producing the claimed invention based on the combined teachings of prior art and optimization based on general knowledge of crystalline/polymorph and pharmaceutical formulation. Therefore, the invention as a whole is prima facie obvious to one of ordinary skill in the art before the effective filing date of instant invention, as evidenced by the references, especially in the absence of evidence to the contrary.
Claims 1,15-17, 28-29, 51,and 53-59 are rejected under 35 U.S.C. 103 as being unpatentable over Schneider et al. (US20230416219A1, Applicant’s IDS dated 12/30/2025, Cite #012).
Regarding R-MDMA salt, Schneider discloses crystalline form salt or polymorphs of (R)-MDMA., composition comprising aforementioned crystalline salt forms, and method for treating neurological disease and/or a psychiatric disorder in a subject (See abstract; [0003], [0057], Example 1-22; claims 1- 50). Schneider teaches variety salt for (R)-MDMA, e.g. HCl, citrate, tartrate, malate, etc. (See [0058], Table 1, Example 1-22).
Regarding limitations of claims 16-17, and 53-59, Schneider teaches property R-MDMA crystalline salt characterized by variety of analysis, e.g. XRPD, DSC, TGA analysis (See Example 1-22, Figures 1-46). For example, Schneider teaches a solid crystalline form of R-MDMA tartrate characterized by XRPD signals, e.g. 13.3, 15.4, 17.8, 26.4, etc. (±0.2 °2θ , Cu Kα1 radiation) (See Example 12, [0093], Table 11 ) that read on XRPD peaks recited by instant claims. Schneider also teaches DSC, TGA analysis for R-MDMA crystalline salt form(See Figure 3, 4, 9, etc.). Schneider teaches single crystal X-ray structure determination technique to evaluate the monoclinic cell parameters of a crystalline form (See Example 8, [0089]). Please note the XRPD pattern, unit cell parameter, DSC, TGA, melting point, etc. are the properties of the crystalline salt which are inseparable from the product itself. Once the crystalline salt from is obtained, XRPD pattern, melting point, DSC, and other properties of the crystalline form could be easily measured by a person of ordinary skilled in the art through routine method and general knowledge of crystallization.
Regarding claims 28-29 and 51 , Schneider teaches pharmaceutical composition, comprising a crystalline form of R-MDMA salt, and a pharmaceutically acceptable excipient (See [0008], claim 7). Schneider teaches oral dosage form for oral administration (See [0068]).
Schneider collectively teaches variety of crystalline salt forms of R-MDMA characterized by XRPD pattern, unit crystal cell parameter, DSC, TGA, etc.
It would have been prima facie obvious to one of the ordinary skilled in the art before the effective filing date of instant invention to explore more crystalline salt forms of R-MDMA taught by Schneider, together with experimentation/ optimization including salt screening based on general knowledge of crystallization and pharmaceutical formulation, and arrive at instantly claimed invention with reasonable expectation of success. A skilled artisan would be motivated to further explore different crystalline salt form of R-MDMA with reasonable expectation that alternative crystalline salt form of R-MDMA might provide improved chemical and physical properties, e.g. storage stability and solubility, etc.
It is a settled principle of law that a mere carrying forward of an original patented conception involving only change of form, proportions, or degree, or the substitution of equivalents doing the same thing as the original invention, by substantially the same means, is not such an invention as will sustain a patent, even though the changes of the kind may produce better results than prior inventions, See MPEP 2144.05 IIA.
One of ordinary skill in the art would have had reasonable expectation of success in producing the claimed invention based on the combined teachings of prior art and optimization based on general knowledge of crystalline/polymorph and pharmaceutical formulation. Therefore, the invention as a whole is prima facie obvious to one of ordinary skill in the art before the effective filing date of instant invention, as evidenced by the references, especially in the absence of evidence to the contrary.
Double Patenting
The nonstatutory double patenting rejection is based on a judicially created doctrine grounded in public policy (a policy reflected in the statute) so as to prevent the unjustified or improper timewise extension of the “right to exclude” granted by a patent and to prevent possible harassment by multiple assignees. A nonstatutory double patenting rejection is appropriate where the conflicting claims are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg, 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); In re Goodman, 11 F.3d 1046, 29 USPQ2d 2010 (Fed. Cir. 1993); In re Longi, 759 F.2d 887, 225 USPQ 645 (Fed. Cir. 1985); In re Van Ornum, 686 F.2d 937, 214 USPQ 761 (CCPA 1982); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); In re Thorington, 418 F.2d 528, 163 USPQ 644 (CCPA 1969).
A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) or 1.321(d) may be used to overcome an actual or provisional rejection based on nonstatutory double patenting provided the reference application or patent either is shown to be commonly owned with the examined application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. See MPEP § 717.02 for applications subject to examination under the first inventor to file provisions of the AIA as explained in MPEP § 2159. See MPEP § 2146 et seq. for applications not subject to examination under the first inventor to file provisions of the AIA . A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b).
The filing of a terminal disclaimer by itself is not a complete reply to a nonstatutory double patenting (NSDP) rejection. A complete reply requires that the terminal disclaimer be accompanied by a reply requesting reconsideration of the prior Office action. Even where the NSDP rejection is provisional the reply must be complete. See MPEP § 804, subsection I.B.1. For a reply to a non-final Office action, see 37 CFR 1.111(a). For a reply to final Office action, see 37 CFR 1.113(c). A request for reconsideration while not provided for in 37 CFR 1.113(c) may be filed after final for consideration. See MPEP §§ 706.07(e) and 714.13.
The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The actual filing date of the application in which the form is filed determines what form (e.g., PTO/SB/25, PTO/SB/26, PTO/AIA /25, or PTO/AIA /26) should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission. For more information about eTerminal Disclaimers, refer to www.uspto.gov/patents/apply/applying-online/eterminal-disclaimer.
Claims 1,15-17, 28-29, 51,and 53-59 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-11 of U.S. Patent No. 12492178B2, in view of Duncton et al.( WO 2023092044 A2, Applicant’s IDS dated 12/30/2025, Cite # 022).
Reference claims are directed to a crystalline form of (R)-3,4-methylenedioxymethamphetamine (R)-MDMA HCl, characterized by X-ray Powder Diffraction (XRPD) peaks, DSC, TGA analysis, etc.
The difference between reference claims and instant claims are hydrochloride salt versus nitrate salt form.
The collective teaching of Duncton is elaborated in preceding 102 and 103 rejection and applied as before. Duncton collectively teaches variety of crystalline forms salt (e.g. nitrate salt) of (R)-MDMA, (S)-MDMA characterized by XRPD pattern, unit crystal cell parameter, DSC, TGA, etc.
It is common practice in the pharmaceutical industry to explore different salt form and crystalline forms of active compound for purpose of stability, solubility and bioavailability, etc. as shown in Duncton . It would have been prima facie obvious to one of the ordinary skilled in the art to explore different crystalline salt form of (R)-MDMA based on the teaching of reference claims and Duncton , together with experimentation/ optimization based on general knowledge of crystallization/formulation. Once the crystalline is obtained, XRPD, melting point, DSC, and other properties of the crystalline salt could be easily measured by a person of ordinary skilled in the art through routine method and general knowledge of crystallization.
The instant application shares at least one common inventor and applicant with the reference patent. Further, the instant application is not related to the reference application thus no 35 USC 121 shield exists.
Claims 1,15-17, 28-29, 51,and 53-59 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-16 of copending U.S. application No. 19/431,012, in view of Duncton et al.( WO 2023092044 A2, Applicant’s IDS dated 12/30/2025, Cite # 022). This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Reference claims are directed to a composition comprising (R)-3,4-methylenedioxymethamphetamine (R)-MDMA O-methyl mandelate salt form characterized by X-ray Powder Diffraction (XRPD) , DSC, TGA, etc.
The difference between reference claims and instant claims are O-methyl mandelate salt versus nitrate salt form.
The collective teaching of Duncton is elaborated in preceding 102 and 103 rejection and applied as before. Duncton collectively teaches variety of crystalline forms salt (e.g. nitrate salt) of (R)-MDMA, (S)-MDMA characterized by XRPD pattern, unit crystal cell parameter, DSC, TGA, etc.
It is common practice in the pharmaceutical industry to explore different salt form and crystalline forms of active compound for purpose of stability, solubility and bioavailability, etc. as shown in Duncton. It would have been prima facie obvious to one of the ordinary skilled in the art to explore different crystalline salt form of (R)-MDMA based on the teaching of reference claims and Duncton, together with experimentation/ optimization based on general knowledge of crystallization/formulation. Once the crystalline is obtained, XRPD, melting point, DSC, and other properties of the crystalline salt could be easily measured by a person of ordinary skilled in the art through routine method and general knowledge of crystallization.
Reference application is a continuation of instant application, no 35 USC 121 shield exists.
Claims 1,15-17, 28-29, 51,and 53-59 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 24-36 of copending U.S. application No. 19/366,168, in view of in view of Duncton et al.( WO 2023092044 A2, Applicant’s IDS dated 12/30/2025, Cite # 022) . This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Reference claims are directed to a crystalline form of (R)-3,4-methylenedioxymethamphetamine (R)-MDMA HCl, characterized by X-ray Powder Diffraction (XRPD) peaks, DSC, TGA analysis, etc.
The difference between reference claims and instant claims are hydrochloride salt versus nitrate salt form.
The collective teaching of Duncton is elaborated in preceding 102 and 103 rejection and applied as before. Duncton collectively teaches variety of crystalline forms salt (e.g. nitrate salt) of (R)-MDMA, (S)-MDMA characterized by XRPD pattern, unit crystal cell parameter, DSC, TGA, etc.
It is common practice in the pharmaceutical industry to explore different salt form and crystalline forms of active compound for purpose of stability, solubility and bioavailability, etc. as shown in Duncton . It would have been prima facie obvious to one of the ordinary skilled in the art to explore different crystalline salt form of (R)-MDMA based on the teaching of reference claims and Duncton, together with experimentation/ optimization based on general knowledge of crystallization/formulation. Once the crystalline is obtained, XRPD, melting point, DSC, and other properties of the crystalline salt could be easily measured by a person of ordinary skilled in the art through routine method and general knowledge of crystallization.
The instant application shares at least one common inventor and applicant with the reference patent. Further, the instant application is not related to the reference application thus no 35 USC 121 shield exists.
Conclusion
No claim is allowed.
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure.
Bachliński et al. Issues Of Forensic Science 296(2) 2017, MDMA (3,4-methylenedioxymethamphetamine) nitrate – an atypical salt form or a new trend in the drug market?
Pitts et al. Psychopharmacology, 235, 377–392 (2018). https://doi.org/10.1007/s00213-017-4812-5, (±)-MDMA and its enantiomers: potential therapeutic advantages of R (−)-MDMA.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to LIYUAN MOU whose telephone number is (571)270-1791. The examiner can normally be reached Mon-Fri 9:00-5:30.
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/LIYUAN MOU/Examiner, Art Unit 1628
/JARED BARSKY/Primary Examiner, Art Unit 1628
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