DETAILED ACTION
This office action is in response to applicant’s filing dated April 1, 2026.
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 1-21 are pending in the instant application. Acknowledgement is made of Applicant's remarks filed April 1, 2026.
Election/Restrictions
Applicant's election with traverse of Group I, claims 1-11, 14, 15, and 17, drawn to a 6bR,10aS)-8-(3-(4-fluorophenoxy)propyl)-6b,7,8,9,10,10a- hexahydro-1H-pyrido[3',4':4,5]pyrrolo[1,2,3-de]quinoxalin-2(3H)-one in solid, crystalline salt form in the reply filed on April 1, 2026 is acknowledged. The traversal is on the grounds that the prior art does not teach a solid, crystalline salt form. This is not found persuasive because as set forth previously on the record, Snyder teaches a solid tosylate salt of 6bR,10aS)-8-(3-(4-fluorophenoxy)propyl)-6b,7,8,9,10,10a- hexahydro-1H-pyrido[3',4':4,5]pyrrolo[1,2,3-de]quinoxalin-2(3H)-one. Each crystalline form is dependent on the orientation and arrangement of the molecules of the compound often measured by XRPD. Thus, crystalline form is a variable and not a technical feature shared by all the species and groups. Moreover, Snyder teaches the tosylate salt is obtained as a solid using acetonitrile [0064]. The instant specification teaches a process for the production of solid, crystalline salt form of Compound A wherein the solvent is acetonitrile, see paragraph [0030], 1.5. Thus, a solid, crystalline tosylate salt of 6bR,10aS)-8-(3-(4-fluorophenoxy)propyl)-6b,7,8,9,10,10a- hexahydro-1H-pyrido[3',4':4,5]pyrrolo[1,2,3-de]quinoxalin-2(3H)-one is taught by the prior art. Therefore, since the technical feature, i.e. a (6bR,10aS)-8-(3-(4-fluorophenoxy)propyl)-6b,7,8,9,10,10a- hexahydro-1H-pyrido[3',4':4,5]pyrrolo[1,2,3-de]quinoxalin-2(3H)-one solid, crystalline salt is taught by the prior art, the technical feature lacks novelty.
The requirement is still deemed proper and is therefore made FINAL.
Claims 12, 13, 16, and 18-21 are withdrawn from further consideration pursuant to 37 CFR 1.142(b), as being drawn to a nonelected invention, there being no allowable generic or linking claim. Applicant timely traversed the restriction (election) requirement in the reply filed on April 1, 2026.
Applicant’s election without traverse of p-toluenesulfonate salt as the elected salt species in the reply filed on April 1, 2026 is acknowledged.
Claims 3, 14 and 15 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected species, there being no allowable generic or linking claim. Election was made without traverse in the reply filed on April 1, 2026.
Claims 1, 2, 4-11 and 17 are presently under examination as the relate to the elected species: (6bR,10aS)-8-(3-(4-fluorophenoxy)propyl)-6b,7,8,9,10,10a- hexahydro-1H-pyrido[3',4':4,5]pyrrolo[1,2,3-de]quinoxalin-2(3H)-one toluenesulfonate salt.
Priority
The present application is a 371 of PCT/US22/72802 filed on June 7, 2022, which claims benefit of U.S. Provisional Application No. 63/197,848 filed on June 7, 2021.
Information Disclosure Statement
The information disclosure statements (IDS) submitted on December 31, 2024; May 30, 2025; and April 1, 2026 are in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statements are being considered by the examiner, except where marked with a strikethrough.
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Drawings
Acknowledgement is made of the drawings received on December 6, 2023. These drawings are accepted.
Specification
Applicant is reminded of the proper content of an abstract of the disclosure.
In chemical patent abstracts for compounds or compositions, the general nature of the compound or composition should be given as well as its use, e.g., “The compounds are of the class of alkyl benzene sulfonyl ureas, useful as oral anti-diabetics.” Exemplification of a species could be illustrative of members of the class. For processes, the type of reaction, reagents and process conditions should be stated, generally illustrated by a single example unless variations are necessary. In the instant case, the abstract fails to provide a general use for the disclosed salts, crystals, or cocrystals. Moreover, the salts, crystals, or cocrystals of the instant application are salts, crystals, or cocrystals:
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and not to substituted heterocycle fused gamma-carbolines generically.
Applicant is reminded of the proper language and format for an abstract of the disclosure.
The abstract should be in narrative form and generally limited to a single paragraph on a separate sheet within the range of 50 to 150 words in length. The abstract should describe the disclosure sufficiently to assist readers in deciding whether there is a need for consulting the full patent text for details.
The language should be clear and concise and should not repeat information given in the title. It should avoid using phrases which can be implied, such as, “The disclosure concerns,” “The disclosure defined by this invention,” “The disclosure describes,” etc. In addition, the form and legal phraseology often used in patent claims, such as “means” and “said,” should be avoided. In the instant case, the abstract contains phrases which can be implied.
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 11 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.
Regarding claims 2 and 11, the phrase e.g., which is the abbreviation for “for example” renders the claim indefinite because it is unclear whether the limitation(s) following the phrase are part of the claimed invention. See MPEP § 2173.05(d).
Claim Rejections - 35 USC § 102
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
Claims 1 and 17 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Snyder et al (WO 2019/237037 A1, cited in a previous Office Action).
Regarding claim 1, Snyder teaches Compound of Formula (I) is Example 1 (page 48 and claim 6):
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wherein the Compound of Formula (I) is in the form of a tosylate salt (claim 7) and partially purified product (Example (1)) is further purified with a semi-preparative HPLC system using a gradient of 0 - 60% acetonitrile in water containing 0.1% formic acid over 16 min to obtain the title product as a solid. The instant specification teaches a process for the production of solid, crystalline salt form of Compound A wherein the solvent is acetonitrile, see paragraph [0030], 1.5. Tosylate salt of Compound A reads on p-toluene sulfonic acid salt. MPEP 2112.01 states:
Where the claimed and prior art products are identical or substantially identical in structure or composition, or are produced by identical or substantially identical processes, a prima facie case of either anticipation or obviousness has been established. In re Best, 562 F.2d 1252, 1255, 195 USPQ 430, 433 (CCPA 1977). "When the PTO shows a sound basis for believing that the products of the applicant and the prior art are the same, the applicant has the burden of showing that they are not." In re Spada, 911 F.2d 705, 709, 15 USPQ2d 1655, 1658 (Fed. Cir. 1990). In the instant case, the solid, tosylate salt of Compound A of prior art is produced by substantially identical process (i.e. using acetonitrile solvent) and thus anticipates the instantly claimed solid, crystalline p-toluenesulfonic salt of the instant claims.
Regarding claim 17, Snyder teaches a unit dosage, for example a tablet or capsule, comprising the compound of formula (I) in tosylate salt form and a pharmaceutically acceptable diluent or carrier (claim 8).
Thus, the teachings of Snyder anticipate the salt and composition of claims 1 and 17.
Claim Rejections - 35 USC § 103
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
Claims 1, 4-11, and 17 are rejected under 35 U.S.C. 103 as being unpatentable over Snyder et al (WO 2019/237037 A1, cited in a previous Office Action).
As set forth in the 102 rejection above, Snyder teaches a solid, crystalline (6bR,10aS)-8-(3-(4-fluorophenoxy)propyl)-6b,7,8,9,10,10a- hexahydro-1H-pyrido[3',4':4,5]pyrrolo[1,2,3-de]quinoxalin-2(3H)-one toluenesulfonate salt and a pharmaceutical composition comprising the solid, crystalline (6bR,10aS)-8-(3-(4-fluorophenoxy)propyl)-6b,7,8,9,10,10a- hexahydro-1H-pyrido[3',4':4,5]pyrrolo[1,2,3-de]quinoxalin-2(3H)-one toluenesulfonate salt and a pharmaceutical carrier.
Snyder does not explicitly teach the salt is at least 98% pure (instant claim 4), comprises less than 1% of the compound in free base form (instant claim 5), comprises less than 1 wt% of any p-toluenesulfonic acid (instant claim 6), less than 0.1 % of synthetic precursor or side-product from the synthetic method (instant claim 7), less than 5000 ppm of all residual solvents (instant claim 8), less than 100 ppm of 1-(3-chloropropoxy)-4-fluorobenzene (instant claim 9), less than 1 wt% of water (instant claim 10), or less than 100 ppm of p-toluenesulfonate alkyl esters (instant claim 11). However, It would have been prima facie obvious to one of ordinary skill in the art before the effective filing date to remove any synthetic precursor of or side-product from the synthetic method used to prepare the salt (i.e. base compound (Compound A), p-toluenesulfonic acid or p-toluenesulfonate alkyl esters, residual solvents, or water) to arrive at the pure solid, crystalline (6bR,10aS)-8-(3-(4-fluorophenoxy)propyl)-6b,7,8,9,10,10a- hexahydro-1H-pyrido[3',4':4,5]pyrrolo[1,2,3-de]quinoxalin-2(3H)-one toluenesulfonate salt having substantially synthetic precursor of or side-product from the synthetic method used to prepare the salt (i.e. base compound (Compound A), p-toluenesulfonic acid or p-toluenesulfonate alkyl esters, residual solvents, or water). The skilled artisan would have been motivated to remove such precursors or side-products to reduce degradation or reduction of efficacy of the active solid, crystalline salt compound due to the presence of such products. Moreover, regarding instant claim 9, the method of producing the pure solid, crystalline (6bR,10aS)-8-(3-(4-fluorophenoxy)propyl)-6b,7,8,9,10,10a- hexahydro-1H-pyrido[3',4':4,5]pyrrolo[1,2,3-de]quinoxalin-2(3H)-one toluenesulfonate salt does not utilize any 1-(3-chloropropoxy)-4-fluorobenzene, thus it is safe to assume that there is no 1-(3-chloropropoxy)-4-fluorobenzene present in the composition.
Taken together, all this would result in the composition of claims 1, 4-11, and 17 with a reasonable expectation of success.
Conclusion
Claims 1, 2, 4-11, and 17 are rejected.
No claim is allowed.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to RAYNA B RODRIGUEZ whose telephone number is (571)272-7088. The examiner can normally be reached 8am-5:00pm, Monday - Thursday.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Amy L Clark can be reached at 571-272-1310. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/Rayna Rodriguez/ Primary Examiner, Art Unit 1628
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