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
Claims 1-49 are currently pending in the application.
Priority
Applicant’s claim for the benefit of a prior-filed application under 35 U.S.C. 119(e) or under 35 U.S.C. 120, 121, or 365(c) is acknowledged. The earliest application that provides adequate support or enablement in the manner provided by the first paragraph of 35 U.S.C. 112 for one or more claims of this application is the provisional application 63/596,060. Thus, the priority date of the instant invention is November 3rd, 2023.
IDS
The information disclosure statement (IDS) submitted on 12/04/25 and 04/04/26 are acknowledged and have been entered. The submission is in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statements have been considered by the examiner.
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 primary purpose of this requirement of definiteness of claim language is to ensure that the scope of the claims is clear so the public is informed of the boundaries of what constitutes infringement of the patent. A secondary purpose is to provide a clear measure of what applicant(s) regard as the invention so that it can be determined whether the claimed invention meets all the criteria for patentability and whether the specification meets the criteria of 35 U.S.C. 112, first paragraph with respect to the claimed invention.", (see MPEP § 2173).
Claims 13-17 and 37-41 are rejected under 35 U.S.C. 112, second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which applicant regards as the invention.
Specifically, claim 13-17 and 37-41 recites that the compound of formula (VI) contains moieties R1 and R2 that are combined to form a ring. Independent claim 1 however teaches that R1 and R2 are “independently” inter alia “…a cycloalkyl, an aryl, or a heteroaryl” (see claim 1, lines 6-7). Nowhere in claim 1 is it recited that R1 and/or R2 can be combined together to form a ring, let alone a 3, 4, 5, or 6-membered ring. Consequently, such claims are vague and indefinite as the metes and bounds of the claims are not clearly delineated.
As a result of the above inconsistencies, the aforementioned claims are unable to be examined as disclosed given that the scope of the claimed subject matter would not be able to be determined by one of ordinary skill in the art. For the sake of compact prosecution, the examiner will construe that R1 and/or R2 can be inter alia “a cycloalkyl, an aryl ring, or a heteroaryl ring”.
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(d):
(d) REFERENCE IN DEPENDENT FORMS.—Subject to subsection (e), a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
The following is a quotation of pre-AIA 35 U.S.C. 112, fourth paragraph:
Subject to the following paragraph [i.e., the fifth paragraph of pre-AIA 35 U.S.C. 112], a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
Claims 13-17 and 37-41 are rejected under 35 U.S.C. 112(d) or pre-AIA 35 U.S.C. 112, 4th paragraph, as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends.
Specifically claims 13-17 and 37-41 recite that the compound of formula (VI) contains moieties R1 and R2 that are combined to form a ring. Independent claim 1 however teaches that R1 and R2 are “independently” inter alia “…a cycloalkyl, an aryl, or a heteroaryl” (see claim 1, lines 6-7). Nowhere in claim 1 is it recited that R1 and/or R2 can be combined together to form a ring, let alone a 3, 4, 5, or 6-membered ring. Consequently, such claims are not further limiting as they broaden the scope of the claims.
Since claim 1 does not provide any alternative definition for R1 and R2, the examiner contends that R1 and R2 is only defined by what is provided in claim 1 and therefore the aforementioned claims failed to further limit the scope of claims 1 and 25. Applicant may therefore cancel the claim(s), amend the claim(s) to place the claim(s) in proper dependent form, rewrite the claim(s) in independent form, or present a sufficient showing that the dependent claim(s) complies with the statutory requirements.
Claim Rejections - 35 USC § 112 – 1st Paragraph, Written Description
The following is a quotation of the first paragraph of 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.
Claims 13-17 and 37-41 are rejected under 35 U.S.C. 112, first paragraph, as failing to comply with the written description requirement. The claims 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 inventors, at the time the application was filed, had possession of the claimed invention. This is a written description rejection, rather than an enablement rejection under 35 U.S.C. 112, first paragraph. Applicant is directed to the Guidelines for the Examination of Patent Applications Under the 35 U.S.C. 112, 1st "Written Description" Requirement, Federal Register, Vol. 66, No. 4, pages 1099-1111, Friday January 5, 2001.
The claims are drawn to the compound of formula (VI) or to the composition comprising the compound of formula (VI), wherein R1 and R2 are combined to form a 3-6 membered ring.
Vas-Cath Inc. V. Mahurkar, 19 USPQ2d 1111, states that Applicant must convey with reasonable clarity to those skilled in the art that, as of the filing date sought, he or she was in possession of the invention. The invention, for purposes of the written description inquiry, is whatever is now claimed (see page 1117).
To provide adequate written description and evidence of possession of a claimed genus, the specification must provide sufficient distinguishing characteristics of the genus. The factors to be considered include disclosure of complete or partial structure, physical and/or chemical properties, functional characteristics, structure/function correlation, methods of making the claimed product, or any combination thereof.
A description of a genus may be achieved by means of a recitation of a representative number of species falling within the scope of the genus or of a recitation of structural features common to the members of the genus, which features constitute a substantial portion of the genus. Regents of the University of California v. Eli Lilly & Co., 119 F3d 1559, 1569, 43 USPQ2d 1398, 1406 (Fed. Cir. 1997). In Regents of the University of California v. Eli Lilly (43 USPQ2d 1398-1412), the court held that a generic statement which defines a genus of nucleic acids by only their functional activity does not provide an adequate written description of the genus. The court indicated that, while applicants are not required to disclose every species encompassed by a genus, the description of the genus is achieved by the recitation of a representative number of species falling within the scope of the claimed genus. At section B(i), the court states, "An adequate written description of a DNA ... requires a precise definition, such as by structure, formula, chemical name, or physical properties, not a mere wish or plan for obtaining the claimed chemical invention."
In this instance, the specification failed to delineate any compound whose R1 and R2 moieties are combined to form a ring. Importantly, the specification teaches synthesis of 12 compounds (see pg.41, table 1) wherein none of them are taught to be a ring, let alone a ring that is formed by the combination of R1 and R2. Examples of the synthesized compounds are as followed:
PNG
media_image1.png
68
849
media_image1.png
Greyscale
(Prodrug 7, pg. 39) which clearly defined R1 and R2 as hydrogen with no ring moiety present. In fact, all of the synthesized compounds failed to recite a ring at position R1 or R2 and no combination of R1 or R2 is taught in the specification.
Consequently, the claims encompass species, ranging from a compound that contains a cycloalkyl ring to rings such as naphthalene or pyridine. Since the specification provides no support for any compound that contains a ring, then the claims lack written
description as currently recited.
In addition, claims 37-41 recite a composition comprising said compounds that lack support and further contributing to the lack of written description. The disclosure fails to provide support for species wherein Rent an1 and R2 are combined to form a 3, 4, 5, or a 6-membered ring. Thus the present claims encompasses numerous species that are not further described.
All of the disclosed species are very closely related R1 and R2 are hydrogen and there is no evidence of record of other species that are structurally representative of the broadly claimed genus in claims 13-17 and 37-41. As a result, the genus as disclosed is very limited in scope.
As discussed in the Guidelines for the Examination of Patent Applications Under the 35 U.S.C. 112, 1st “Written Description” Requirement, Federal Register, Vol. 66, No. 4, pages 1099-1111, Friday January 5, 2001 (“the Written Description Guidelines”), the examination of patent claims for compliance with the Written Description Requirement should include:
1. A determination as to what the claim as a whole covers
2. A full review of the application to understand how the applicant provides support for the claimed invention including each element and/or step
3. A determination as to whether one skilled in the art would recognize that the applicant was in possession of the claimed invention as a whole at the time of filing. This determination should include the following considerations:
a. Actual reduction to practice
b. Disclosure of drawings or structural chemical formula
c. Sufficient relevant identifying characteristics, such as:
i. Complete structure
ii. Partial structure
iii. Physical and/or chemical properties
iv. Functional characteristics when coupled with a known or disclosed correlation between function and structure
d. Method of making the claimed invention
e. Level of skill and knowledge in the art
f. Predictability in the art
4. For each claim drawn to a single embodiment of species, consider the above factors in regard to that embodiment or species to determine whether one of ordinary skill in the art would recognize that the applicant was in possession of the species or embodiment at the time of filing
5. For each claim drawn to a genus, consider the above factors to determine whether there is disclosure of a representative number of species which would lead one skilled in the art to conclude that the applicant was in possession of the claimed invention. The number of species required to represent a genus will vary, depending on the level of skill and knowledge in the art and variability among the claimed genus. For instance, fewer species will be required where the skill and knowledge in the art is high, and more species will be required where the claimed genus is highly variable.
As to (1) above, the claims encompass any compound that may or may not contain a ring ranging from cycloalkyl to aryl and to heteroaryl, which is a genus encompassing millions of possible species. As discussed above, the specification discloses 12 structurally related species that are limited in scope to a very limited number of closely related compounds having the same substituents thereon.
As to (2) above, Applicants provide support for the claimed compounds by disclosure of general schemes and 12 specific species that fall within the scope of claims.
As to (3) above, the Specification only discloses twelve possible species encompassed by the aforementioned generic formula in claims 2-3. Actual reduction to practice is limited to a few species. The only relevant identifying characteristic disclosed in the Specification for the claimed compounds is the broadly described genus delineated in claims 13-17 and 37-41. The Specification does not disclose any methods of making said compounds of the generic Formula.
In view of the above, the skilled artisan would not recognize that Applicants were in possession of the broad scope of the claimed compounds encompassed by the general formula.
As to (5) above, the genus in the instant case is the claimed genus of the generic formula of claims 13-17 and 32-41. This genus is clearly "highly variable", encompassing any and all compounds that fall within the scope of the described Formula VI. As discussed above, this genus encompasses the aforementioned species, which are clearly highly variable.
Applicant’s disclosure of 12 species that appear to fall within the scope of the generic Formula VI as listed in table 1.
In view of the above, the Specification does not provide written support for the vast scope of compounds encompassed by the generic formula as presently claimed.
The specification does not clearly allow persons of ordinary skill in the art to recognize that he or she invented what is claimed (see Vas-Cath at page 1116). Applicant is reminded that Vas-Cath makes clear that the written description provision of 35 U.S.C. 112 is severable from its enablement provision (see page 1115).
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)(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, 12, 23-25, 35-36, and 47-49 are rejected under 35 U.S.C. 102(a) as being anticipated by Clark et al. (WO 2023/283323 A1, filed on an IDS 1449 and filed by Applicant).
Specifically, Clark et al. teach 3,4-methylenedioxymethamphetamie compounds as prodrugs that can be used for psychedelics and useful in disorders in which increased MDMA is beneficial (see abstract). Clark et al. further teach compounds of formula (I) wherein selected compounds include:
PNG
media_image2.png
167
628
media_image2.png
Greyscale
wherein R2, R3, and R4 are H; R1 is C1-alkyl or methyl; R6 is C1 alkyl or methyl; X1 and X2 are O and R5 is C2 or C3 alkyl (see paragraph 0082). Clark et al. further teach that the compounds of the invention can be formulated as pharmaceutical compositions comprising the compound of the invention and a pharmaceutically acceptable excipient or carriers such as lactose (i.e. a bulky agent; see paragraphs 0083 and 000305).
Clark et al. do not teach that the compound persists through a first pass metabolism of a mammal or that the compound acts as a partial agonist of CNS serotonin receptor. However given that Clark teaches the exact same compound encompass by the instant invention, such characteristic will be inherent to the compound. It is noted that "Products of identical chemical composition cannot have mutually exclusive properties." In re Spada, 911 F.2d 705, 709, 15 USPQ2d 1655, 1658 (Fed. Cir. 1990). A chemical composition and its properties are inseparable. Therefore, if the prior art teaches the identical chemical structure, the properties applicant discloses and/or claims are necessarily present.
Accordingly, the teachings of Clark et al. anticipate claims 1, 12, 23-25, 35-36j, and 47-49.
Claims 1, 5-6, 21, 23-25, 29-30, 46, and 47-48 are rejected under 35 U.S.C. 102(a) as being anticipated by Manaka et al. (Helvetica Chimica Acta, 2007, Vol. 90, pgs. 128-142).
Manaka et al. teach ring opening reactions of benzylaziridines-2-carboxylate that lead to asymmetric synthesis of an amphetamine type compounds (see abstract and pg. 128). Manaka et al. further teach scheme 6 which led to compound 14 produced at a 41% over all yield (see scheme 6, pg. 136):
PNG
media_image3.png
642
874
media_image3.png
Greyscale
Additionally, Manaka et al. specifically recites compound 14 as: (=(+)-tert-Butyl[(1R)-2-(1,3-Benzodioxol-5-yl)-1-methylethyl]carbamate; (+)-14))-i.e. the R-enantiomer wherein R1 is a methyl; R2, R3, R4 are H; R6 is H; X1 and X2 are O and R5 is t-butyl or C4 alkyl and mixed in THF (i.e. a composition and see pg. 141).
Manaka et al. do not teach that the compound persists through a first pass metabolism of a mammal or that the compound acts as a partial agonist of CNS serotonin receptor. However given that Clark teaches the exact same compound encompass by the instant invention, such characteristic will be inherent to the compound. It is noted that "Products of identical chemical composition cannot have mutually exclusive properties." In re Spada, 911 F.2d 705, 709, 15 USPQ2d 1655, 1658 (Fed. Cir. 1990). A chemical composition and its properties are inseparable. Therefore, if the prior art teaches the identical chemical structure, the properties applicant discloses and/or claims are necessarily present.
Accordingly, the teachings of Manaka et al. anticipate claims 1, 5-6, 21, 23-25, 29-30, 46, and 47-48.
Claims 1-2, 4-5, 23-26, 28-29, and 47-48 are rejected under 35 U.S.C. 102(a) as being anticipated by Buck et al. (American Chemical Society (ACS), 1931, Vol. 53, pgs. 2688-2692).
Buck et al. teach Rhodanine derivatives of β-phenylethylamines which possess similar pharmacological properties to adrenaline, epinine but due to the rhodamine ring may also possess properties similar to barbituric acid derivatives (see pg. 2688). The compounds are directed to an unsubstituted ether benzene ring and a non-alkylated rhodamine ring (see pg. 2688). Such compound would typically have low solubility but modifying said compound on the rhodamine ring would lead to higher solubility and thus become more suitable as pharmaceutical composition (see pg. 2689). Importantly, Buck et al. teach the making of dithiocarbamates including the following compound (see pg. 2689-2692):
PNG
media_image4.png
287
573
media_image4.png
Greyscale
wherein R1-R4 are H; R6 is H; X1 and X2 are S and R5 is H.
Johannes et al. do not teach that the compound persists through a first pass metabolism of a mammal or that the compound acts as a partial agonist of CNS serotonin receptor. However given that Clark teaches the exact same compound encompass by the instant invention, such characteristic will be inherent to the compound. It is noted that "Products of identical chemical composition cannot have mutually exclusive properties." In re Spada, 911 F.2d 705, 709, 15 USPQ2d 1655, 1658 (Fed. Cir. 1990). A chemical composition and its properties are inseparable. Therefore, if the prior art teaches the identical chemical structure, the properties applicant discloses and/or claims are necessarily present.
Accordingly, the teachings of Buck et al. anticipate claims 1-2, 4-5, 23-26, 28-29, and 47-48.
Objections
Claims 3, 7-11, 18-20,22, 27,31-34, and 42-45 are objected to because of the following informalities: Claims are dependent upon rejected claims. Applicant is required to incorporate all of the limitations of said claims into the independent claims. Appropriate correction is required.
Conclusion
No claims are allowed.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Director Bonnie Eyler whose telephone number is 571-272-1200. The Supervisory Primary Examiner can normally be reached on 12:00-8:00 PM EST M-F at 571-270-3503. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
Information regarding the status of an application may be obtained from the Patent Application Information Retrieval (PAIR) system. Status information for published applications may be obtained from either Private PAIR or Public PAIR. Status information for unpublished applications is available through Private PAIR only. For more information about the PAIR system, see http://pair-direct.uspto.gov. Should you have questions on access to the Private PAIR system, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative or access to the automated information system, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
/SAMIRA J JEAN-LOUIS/Supervisory Patent Examiner, Art Unit 1642
Prosecution Insights