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 1-12, 18, 37, and 45 are pending in the instant application.
Claims 13-17, 19-36, 38-44, and 46-58 have been canceled.
Election/Restrictions
This action is in response to an election from a restriction requirement filed on March 25th, 2026. There are 15 claims pending and 11 claims under consideration. This is the first action on the merits. The present invention relates to a method of preparing a compound of formula (III).
Applicant’s election of Group I, Claims 1-11, without traverse in the reply received June 24th, 2026 is acknowledged. Claims 12, 18, 37, and 45 are withdrawn as claims directed to a non-elected invention. Therefore, this restriction is considered proper and thus made FINAL.
Domestic Benefit
Acknowledgement is made of Applicant’s claim for domestic benefit based on U.S. Provisional Application No. 63/232,757, filed August 13th, 2021. Claims 1-11, presently under examination, are fully supported by this application and will be evaluated with an effective filing date of August 13th, 2021.
Information Disclosure Statement
The Information Disclosure Statement filed November 13th, 2024 has been fully considered by the examiner, except where marked with a strikethrough.
Specification
The abstract of the disclosure is objected to because the abstract is fewer than 50 words in length.
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.
A corrected abstract of the disclosure is required and must be presented on a separate sheet, apart from any other text. See MPEP § 608.01(b).
Claim Rejections - 35 USC § 102
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
(a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention.
Claims 1-8 and 11 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Reardon et. al. (WO 2020/102053; cited on Applicant’s Information Disclosure Statement filed November 13th, 2024; hereinafter referred to as Reardon).
Regarding Claim 1, at Page 8, Reardon teaches a method of preparing a compound of the formula:
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This is the compound of formula (III) as recited at instant Claim 1.
Reardon teaches at Page 16 this synthesis can be achieved by reacting a compound of the formula:
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with a compound or salt thereof of the formula:
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Regarding the term “salt thereof”, Reardon teaches at Page 7, second paragraph, that this includes bisulfate salts.
Reardon further teaches this reaction generates the following compound:
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Reardon teaches this compound is deprotected with a carboxylic acid deprotecting agent to give the target compound, as noted above.
Regarding the stereochemistry recited at instant Claim 2, Reardon teaches this compound can be obtained via the same method, teaching beginning at Page 15 synthesis of a compound:
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Regarding Claim 3, Reardon teaches the aforementioned reaction is undertaken in the presence of an activating agent.
Regarding Claim 4, Reardon teaches at Page 13, Fourth Paragraph, that the activating agent can be 2,4,6-trialkyl-1,3,5,2,4,6-trioxatriphosphorinane 2,4,6-trioxidde, carbodiimide, a uranium, an activated ester, a phosphonium, 2-alkoxy-1-alkoxycarbonyl-1,2-dihydroquinoline, or alkylchloroformate.
Regarding Claim 5, Reardon teaches at Page 13, Fifth Paragraph, that T3P can be used as the activating agent.
Regarding Claims 6-7, at Page 14, Fourth Paragraph, Reardon teaches carrying out the above reaction (corresponding to the reaction of a compound of formula (I) with a compound of formula (b) as recited at instant Claim 1) can be carried out in a base that is triethylamine.
Regarding Claim 8, at Page 15, First Paragraph, Reardon teaches this reaction is carried out in dichloromethane.
Regarding Claim 11, Reardon teaches at Page 6, Last Paragraph, that the carboxylic acid deprotecting agent is trifluoracetic acid.
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 1-5 and 11 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1 and 3-10 of U.S. Patent No. 10,913,713. Although the claims at issue are not identical, they are not patentably distinct from each other because both sets of claims are drawn to a method of producing a compound of the formula:
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Claim 1 of U.S. Patent No. ‘713 is drawn to a method of preparing a compound of the formula:
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The method comprises the steps of reacting a compound of the formula:
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with a compound or salt thereof of the formula:
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While U.S. Patent No. ‘713 does not specify a bisulfate salt of this compound in the claim, “salt” is defined at Column 6, Lines 57-60 to include bisulfate salts.
Further, in claim 1, the resulting compound is reacted with a carboxylic acid deprotecting agent.
Dependent Claims 3-4 define P1, above as -OtBu. Dependent Claims 5-7 define E, above as -OH, and specifies the presence of the same activating agents as instantly recited at instant Claims 4-5. Dependent Claims 8-10 further specify the use of TFA as a carboxylic acid deprotecting agent, as instantly claimed at Claims 2 and 11.
Taken together, claims 1 and 3-10 of U.S. Patent No. ‘713 read on instant Claims 1-5 and 11.
Claims 1-5 and 11 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1 and 3-9 of U.S. Patent No. 11,591,296. Although the claims at issue are not identical, they are not patentably distinct from each other because both sets of claims are drawn to a method of producing a compound of the formula:
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Claim 1 of U.S. Patent No. ‘296 is drawn to a method of preparing a compound of the formula:
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comprising reacting a compound of the formula:
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with a compound or salt thereof of the formula:
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While U.S. Patent No. ‘296 does not specify a bisulfate salt of this compound in the claim, “salt” is defined at Column 6, Lines 57-60 to include bisulfate salts.
Further, in claim 1, the resulting compound is reacted with a carboxylic acid deprotecting agent.
Dependent Claims 3-4 define P1 as -OtBu. Dependent Claims 5-7 define E as -OH, indicate the presence of an activating agent, and recite the same activating agents as those instantly recited at Claims 4-5. Dependent Claims 8-9 specify the carboxylic acid deprotecting group as TFA.
Taken together, Claims 1 and 3-9 of U.S. Patent No. ‘296 read on instant Claims 1-5 and 11.
Allowable Subject Matter
Claims 9-10 are objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims.
Conclusion
Claims 1-8 and 11 are rejected.
Claims 9-10 are objected to.
No claim is allowed.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to DANIEL JOHN BURKETT whose telephone number is (703)756-5390. The examiner can normally be reached Monday - Friday.
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, Jeffrey Murray can be reached at (571) 272-9023. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/D.J.B./ Examiner, Art Unit 1624
/BRENDA L COLEMAN/ Primary Examiner, Art Unit 1624
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