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
Response to Amendment
Acknowledgment is made of the receipt and entry of the amendment filed on 07/06 /2026.
Claim Status
Claims 1-16 are pending and currently under examination in this office action.
Priority
This instant application 19/431,012, filed on 12/23/2025, is a continuation of 18/401,401 filed 12/30/2023, which claims benefit of US provisional application No. 63/436,531 filed 12/31/2022.
Information Disclosure Statement
The information disclosure statement filed 07/02/2026 is in compliance with the provisions of 37 CFR1.97. Accordingly, the reference listed in IDS are being considered by the Examiner.
Applicant filed over 400 references in IDS dated 12/31/2025 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 one hundred 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).
Response to Arguments
Applicant's remarks filed 07/06/2026 have been fully considered. Any objection and rejection found in the previous Office Action and not repeated herein has been withdrawn in view of amendment and Applicant’s remarks .The text of those objection/rejections not included in this action can be found in the prior office action.
Claim Objections
Claims 5 and 6 remain objected to because of the following informalities:
Claims 5 and 6 are objected as being significantly duplicative claims. Claims 5 and 6 are not identical, but they are not patentably distinct from each other. Both claims 5 and 6 are directed to the same Differential Scanning Calorimetry (DSC) analysis of (R)-MDMA o-methyl mandelate.
Response to Arguments
Applicant argues the scope of claim 5 and 6 are different.
RESPONSE: Applicant’s argument is NOT persuasive. Both claims 5 and 6 are directed to the same DSC thermogram comprising the same endothermic peak at 142±5ºC, and the onset at 141ºC is within the range of 142±5ºC. Thus, the scope of claim 5 and 6 drawn to the same DSC endothermic peak are considered as duplicate.
Claim Interpretation
As disclosed by instant specification (See [0078]),
PNG
media_image1.png
186
556
media_image1.png
Greyscale
According to structural search, instant claimed (R)-3,4-methylenedioxymethamphetamine ((R)-MDMA) o-methyl mandelate has following structure and is entered in STN database on July 22, 2024.
PNG
media_image2.png
851
995
media_image2.png
Greyscale
Please note the limitation of X-ray powder diffraction pattern peaks, DSC, TGA, 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 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.
Claims 1-12 are 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 1 recites (R)-3,4-methylenedioxymethamphetamine ((R)-MDMA) o-methyl mandelate without an article . It’s not clear if claim 1 is referring to a compound, or a composition comprising the compound (R)-3,4-methylenedioxymethamphetamine (R)-MDMA o-methyl mandelate. Thus, claim 1 does not clearly set forth the metes and bounds of the patent protection desired. See MPEP § 2173.05(c).
Claims 2-12 are also rejected due to their dependency on claim 1.
Response to Arguments
Applicant argues that composition is not mentioned in the claim and the skilled person would recognize claim 1 was directed to a compound, in particular the acid addition salt of (R)-MDMA and o-methyl mandelic acid.
RESPONSE: Applicant’s argument is NOT persuasive. Claim 1 merely recites compound name without indicating whether it is intended to be a compound or a composition. Thus, claim 1 fails to define the metes and bounds of claimed subject matter with reasonable certainty. Please note a composition is not limited to combination of an active compound and excipients as instant claim 13, it may also encompass different forms of the same compound, e.g. hydrate, solvate, etc.
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 1-16 are rejected under 35 U.S.C. 103 as being unpatentable over Duncton et al.( WO 2023092044 A2, Applicant’s IDS dated 12/31/2025, Cite #125), in view of Sessa (WO2022150525A1, Applicant’s IDS dated 12/31/2025, Cite #111) and Zapata-Torres et al.(Journal of Molecular Graphics and Modelling 2008, 26(8): 1296-1305, Applicant’s IDS dated 12/31/2025, Cite #402, "Quantum-chemical, NMR and X-ray diffraction studies on (±)-1-[3, 4-(methylenedioxy) phenyl]-2-methylaminopropane").
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; 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; Tables 1-15; claims 1-110, 342-400). 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 limitations of claims 3-12, 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 fumarate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 16.7, 17.3, 18.6, 19.2, 21.9, 23.6(±0.2 °2θ , Cu Kα1 radiation) (See page 22, lines 1-22; page 23, Table 2; Figure 1, claims 5-10), wherein 16.7 ±0.2 θ , 18.6 ±0.2 θ, 23.6 ±0.2 θ read on XRPD peaks recited by instant claims 3 and 4. Duncton also teaches DSC, TGA analysis for MDMA fumarate and crystalline salt form(See page 21, Figure 45). Duncton teaches single crystal X-ray structure determination technique to evaluate the monoclinic cell parameters of a crystalline form (See page 608, line 10-; Table Ex 19-20). 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 13-16, 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 variety of crystalline salt forms of MDMA, (R)-MDMA, (S)-MDMA characterized by XRPD pattern, unit crystal cell parameter, DSC, TGA, etc.
Duncton is silent about o-methyl mandelate salt of MDMA.
Sessa teaches MDMA in variety of salt form, including mandelate salt for treating MDMA-assisted psychotherapy, e.g. PTSD, etc. (See abstract, [0016], [0190]).
MDMA (also known as 'ecstasy') is widely used as recreational drug which has been reported as relatively selective dopaminergic neurotoxin and MDMA hydrochloride crystalline has been studied extensively. Zapata-Torres teaches quantum-chemical, NMR and X-ray diffraction studies on (±)-1-[3,4-(methylenedioxy) phenyl]-2-methylaminopropane (i.e. MDMA) (See whole article). Zapata-Torres teaches the crystal structure of 3,4-methylenedioxymethamphetamine hydrochloride has been determined by X-ray diffraction, including the monoclinic system with cell parameters (See page 1302, Crystallographic results) (which is similar to instant claim 12).
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 in the absence of evidence demonstrating the claimed salt and/or crystalline form thereof 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.
Response to Arguments
Applicant argues the Office has not identified o-methyl mandelic acid in the prior art nor articulated a rationale why the skilled person would have been motivated to make an (R)-MDMA salt with it...(Remarks, page 8).
RESPONSE: Applicant’ argument is fully considered, but NOT persuasive. Please note the obviousness rejection is based on prior art as a whole and general knowledge of POSA, including the genera knowledge of salt screening for crystalline salt/polymorphs and structural similarity. Duncan teaches the salt forms of MDMA, (R)-MDMA, etc. may be formed from a suitable pharmaceutically acceptable acid, including, without limitation, inorganic acids such as hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, phosphoric acid, and the like, as well as organic acids such as formic acid, acetic acid, trifluoroacetic acid, propionic acid, glycolic acid, pyruvic acid, oxalic acid, maleic acid, malonic acid, succinic acid, fumaric acid, tartaric acid, citric acid, benzoic acid, cinnamic acid, mandelic acid, benzene sulfonic acid, isethionic acid, methanesulfonic acid, ethanesulfonic acid, p-toluenesulfonic acid, salicylic acid, xinafoic acid and the like (See page 18, lines 18-26). Sessa also teaches organic acid could form salt with R-MDMA, e.g. mandelate. Preparation of different crystalline salt and optimization thereof for desirable solubility, stability, etc. is a routine and well-established practice as illustrated by Duncan and Sessa. MDMA has a chiral center and mandelic acid is a commonly used chiral resolving agent via diastereomeric salt crystallization, as illustrated by Zingg (1988) and He (2012). Although Duncan and Sessa are silent about specific o-methyl mandelic acid salt, structural similarity provides the rationale to explore o-methyl mandelic acid because mandelic acid and o-methyl mandelic acid are closely related α-hydroxy phenylacetic acid differing only by a methyl substitute on the benzene ring which is finite number of variation on the ring. A skilled artisan would reasonably expect o-methyl mandelic acid would behave similar as mandelic acid forming a salt with R-MDMA based on the close structural similarity. It’s noted instant specification explored about 23 salt screen experiment for R-MDMA free base with different acids, including nitric acid, tartaric acid, mandelic acid, etc. taught by Duncan and Sessa (See [0138]. [0166], Table 1, Table 14). Instant claimed R-MDMA o-methyl mandelate salt is considered as obvious variation/ optimization based on the prior art and general knowledge of crystalline /polymorph and structural similarity in pharmaceutical industry. Applicant does not provide evidence demonstrating instantly claimed (R)-MDMA o-methyl mandelate and/or crystalline form thereof exhibit unexpected property/result relative to the R-MDMA salt taught by prior art.
Applicant argues Duncan teaches 8 crystalline salts of MDMA made from fumaric acid, L-malic acid, maleic acid, mucic acid, phosphoric acid, succinic acid, tartaric acid, and p-toluenesulfonic acid, but could not formed crystalline salt from other acids... Duncton's less than 50% success rate in
forming a crystalline salt is evidence the skilled person would not have a reasonable expectation
of success in forming a crystalline salt of (R)-MDMA with o-methyl mandelic acid. Applicant further argues about XRPD peaks at 16.0 ± 0.2, 16.8 ±0.2, and 18.2 ± 0.2 °28, as required by claim 3 different from Duncton' s MDMA fumarate.
RESPONSE: Please note "the expectation of success need only be reasonable, not absolute”. See MPEP 2143.02.I : “Conclusive proof of efficacy is not required to show a reasonable expectation of success. OSI Pharm., LLC v. Apotex Inc., 939 F.3d 1375, 1385, 2019 USPQ2d 379681 (Fed. Cir. 2019) ("To be clear, we do not hold today that efficacy data is always required for a reasonable expectation of success. Nor are we requiring ‘absolute predictability of success.' "); Acorda Therapeutics, Inc. v. Roxane Lab., Inc., 903 F.3d 1310, 1333, 128 USPQ2d 1001, 1018 (Fed. Cir. 2018) ("This court has long rejected a requirement of ‘[c]onclusive proof of efficacy' for obviousness." (citing to Hoffmann-La Roche Inc. v. Apotex Inc., 748 F.3d 1326, 1331 (Fed. Cir. 2014); PharmaStem Therapeutics, Inc. v. ViaCell, Inc., 491 F.3d 1342, 1364 (Fed. Cir. 2007); Pfizer, Inc. v. Apotex, Inc., 480 F.3d 1348, 1364, 1367–68 (Fed. Cir. 2007) (reasoning that "the expectation of success need only be reasonable, not absolute"))”.
It's noted instant claim 1 is drawn to R-MDMA o-methyl mandelate salt in any form. Forming a salt between R-MDMA amine and an acid would be reasonably expected to succeed by a skilled artisan. Instant claim 2 reciting a crystalline without any characterization is also broad. As for claim 3 reciting three XRPD peaks, a skilled artisan would not be able to distinguish different R-MDMA salt based on the three recited peaks because it’s well recognized in the art that X-ray diffraction patterns may have different appearance due to artifacts/solvents and even the same crystalline form might exhibit different pattern.
Most importantly, 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. MDMA is wildly-known compound in its salt form, e.g. hydrochloride. In the absence of evidence demonstrating unexpected property/result, instant claimed o-methyl mandelate and crystalline form thereof is considered as obvious salt form variation of MDMA taught by prior art. Thus, the 103 rejection is maintained.
Claims 1-16 are rejected under 35 U.S.C. 103 as being unpatentable over Schneider et al. (US20230416219A1, Applicant’s IDS dated 12/31/2025, Cite #061), in view of Sessa (WO2022150525A1, Applicant’s IDS dated 12/31/2025, Cite #111).
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 3-12, 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 hemi-napthylene-1,5-disulfonate characterized by XRPD signals, e.g. 16.0, 16.8, 18.5, 22.8, 23.3(±0.2 °2θ , Cu Kα1 radiation) (See Example 16, [0097], Table 15 ), wherein 16.0 ±0.2 θ, 16.8, 18.5 ±0.2 θ, etc. read on XRPD peaks recited by instant claims 3 and 4. 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 13-16, 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.
Schneider is silent about o-methyl mandelate salt of MDMA.
Sessa teaches MDMA in variety of salt form, including mandelate salt for treating MDMA-assisted psychotherapy, e.g. PTSD, (See abstract, [0016], [0190]).
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.
Response to Arguments
Applicant’s argument is similar to the rejection over Duncton, Sessa, and Zapata-Torres. The examiner’s response is similar to preceding response.
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 1-16 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 Sessa (WO2022150525A1, Applicant’s IDS dated 12/31/2025, Cite #111).
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 o-methyl mandelate salt form. Sessa teaches MDMA in variety of salt form, including mandelate salt for treating MDMA-assisted psychotherapy.
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. 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, 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. See MPEP 804.01.
Claims 1-16 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1, 15, 28 and 51-52 of copending U.S. application No. 18/401,401.
Instant application is a continuation of reference application. Although the claims at issue are not identical, they are not patentably distinct from each other. This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Reference claims are amended to recite a composition comprising (R)-3,4-methylenedioxymethamphetamine (R)-MDMA nitrate salt. Although reference claims are amended to remove instant o-methyl mandelate salt, reference specification expressly discloses crystalline MDMA o-methyl mandelate salt and characterization thereof. Thus, a POSA would have understood that reference application teaches instant salt.
Further, 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. 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, 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.
Claims 1-16 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 Sessa (WO2022150525A1, Applicant’s IDS dated 12/31/2025, Cite #111).
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 o-methyl mandelate salt form. Sessa teaches MDMA in variety of salt form, including mandelate salt for treating MDMA-assisted psychotherapy
It is well-known practice in the pharmaceutical industry to explore different salt form and crystalline forms 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 to explore different crystalline salt form of (R)-MDMA based on the teaching of reference claims, together with experimentation/ optimization based on general knowledge of crystallization. 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. See MPEP 804.01.
Conclusion
No claim is allowed.
THIS ACTION IS MADE FINAL. Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
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.
Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Amy L Clark can be reached on (571)272-1310. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
/LIYUAN MOU/Examiner, Art Unit 1628
/JARED BARSKY/Primary Examiner, Art Unit 1628
Prosecution Insights