DETAILED ACTION
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 the Claims
Claims 1, 3, 5, 7, 9, 15, 17, 22-24, 31, 39, 41, 43, 67, 83, 85, 86, 104, and 117 are pending. Claims 2, 4, 6, 8, 10-14, 16, 18-21, 25-30, 32-38, 40, 42, 44-66, 68-82, 84, 87-103, 105-116, and 118-123 are cancelled.
Status of Priority
The present application is a 35 U.S.C. § 371 national stage patent application of International patent application PCT/US2022/052695, filed on December 13, 2022. This application also claims the benefits of priority to U.S. Provisional Application No. 63/289,368, filed on December 14, 2021.
Specification - Abstract
The abstract of the disclosure is objected to because it is not in compliance with 37 C.F.R. 1.72 (b). Specifically, the sheet presenting the abstract includes other parts of the application or other material. 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).
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.
Specification - Disclosure
The specification has not been checked to the extent necessary to determine the presence of all possible minor errors. Applicant’s cooperation is requested in correcting any errors of which applicant may become aware in the specification.
Claim Objections
Claims 1 and 67 are objected to because of the following informalities:
For consistency, in claim 1:
“said forming the compound of formula (VII) comprising reacting the compound of formula (VII) under Simmons-Smith reaction conditions”should read“said forming the compound of formula (VIII) comprising reacting the compound of formula (VII) under Simmons-Smith reaction conditions”
Currently, claim 67 states:
“X3 is N or CH3”
However, X3 = CH3 is not an option. X3 can be C(CH3) or CH.
Please correctly identify what X3 can be.
For the remainder of this office action, Examiner is assuming that “X3 is… CH3” was intended to read as “X3 is… CH.”
Appropriate correction is required.
Note on 35 USC § 102 and § 103 Rejections
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.
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, 3, 5, 7, 9, 15, 17, 22, 23, 31, 39, 41, 43, 67, 83, 85, 86, 104, and 117 are rejected under 35 U.S.C. 102(a)(1) and 102(a)(2) as being anticipated by:
Phadke (WO2020051538A1; published March 12, 2020).
Phadke discloses the synthesis of the following compound:
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(herein, referred to as Phadke-compound-2; structure can be found in Phadke, abstract; Note: Phadke-compound-2 is also recited in instant claim 117). The synthetic steps required to prepare Phadke-compound-2 is reproduced below:
Converting compound of instant formula (III) [Wingdings font/0xE0] formula (IV) [Wingdings font/0xE0] formula (V) [Wingdings font/0xE0] formula (VI) [Wingdings font/0xE0] formula (VII)
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This scheme can be found on pg. 96 of Phadke.
The details of steps 3D through 6D can be found on pg. 97 and 98 of Phadke.
Step 3D anticipates instant claim 9.
Even though the product of step 3D in the scheme above is not shown, it can be inferred that the structure of that product would be a compound of instant formula (IV) (i.e.,
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) by looking at scheme 3, step 1B on pg. 92 of Phadke.
Step 4D anticipates instant claim 7.
Step 5D anticipates instant claim 5.
Even though the product of step 5D in the scheme above is not shown, it can be inferred that the structure of that product would be a compound of instant formula (VI) (i.e.,
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) by looking at scheme 3, step 3B on pg. 92 of Phadke.
Step 6D anticipates instant claim 3.
Converting compound of instant formula (VII) [Wingdings font/0xE0] formula (VIII) [Wingdings font/0xE0] formula (IX) [Wingdings font/0xE0] formula (I)
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This scheme can be found on pg. 92 of Phadke.
The details of steps 7B through 9B can be found on pg. 94.
Step 7B anticipates instant claim 1.
Step 8B anticipates instant claim 15.
Step 9B anticipates instant claim 17.
Converting compound of instant formula (I) [Wingdings font/0xE0] formula (XI) [Wingdings font/0xE0] formula (XII)
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This scheme can be found on pg. 98.
The details of steps 1E and 2E can be found on pg. 98-99.
Steps 1E and 2E both anticipate instant claims 22, 31, 39, 41, and 43.
Compound 30 of Phadke is a compound of instant formula X wherein:
R1 = H, m = 0, and B = a 6-membered heterocyclyl (specifically, a pyridyl ring) substituted with Br and Me.
Converting compound of instant formula (XII) [Wingdings font/0xE0] formula (XIV)
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This scheme can be found on pg. 99.
The details of step 1F can be found on pg. 99.
Step 1F anticipates instant claim 23, 67, 83, 85, 86, 104, and 117.
Compound 16 of Phadke is a compound of instant formula XIII wherein:
R5 = R6 = H,
X1 = N,
X2 = CRd (wherein Rd = C1 alkyl),
X3 = X5 = CH,
X4 = CRf (wherein Rf = substituted 6-membered heteroaryl; specifically, Me-substituted pyrimidinyl),
R4 = -C(O)Rb (wherein Rb = C1 alkyl).
Claim Rejections - 35 USC § 103
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.
Rejection Part 1:
Claims 1, 3, 5, 7, 9, 15, 17, 22, 23, 31, 39, 41, 43, 67, 83, 85, 86, 104, and 117 are rejected under 35 U.S.C. 103 as being unpatentable over:
Phadke (WO2020051538A1; published March 12, 2020).
Phadke discloses the synthesis of the following compound:
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(herein, referred to as Phadke-compound-2; structure can be found in Phadke, abstract; Note: Phadke-compound-2 is also recited in instant claim 117). The synthetic steps required to prepare Phadke-compound-2 is detailed above in the “Claim Rejections - 35 USC § 102” section.
Phadke does not explicitly disclose the synthesis of the following compound:
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(i.e., the third compound recited in instant claim 117; herein, referred to as compound-117-3). Note: The only difference between compound-117-3 and Phadke-compound-2 is that in compound-117-3, X1 = CH, whereas in Phadke-compound-2, X1 = N.
Although Phadke does not explicitly disclose the synthetic procedure for preparing compound-117-3, a POSITA would have found it prima facie obvious before the effective filing date of the claimed invention to prepare compound-117-3 using the synthetic procedure disclosed by Phadke for preparing Phadke-compound-2 (as discussed above in the “Claim Rejections - 35 USC § 102” section). Given the close structural similarity between compound-117-3 and Phadke-compound-2 (differing only in the substitution of CH for N at the X1 position), a POSITA would have had a reasonable expectation that the reaction conditions disclosed by Phadke for preparing Phadke-compound-2 would likewise be suitable for preparing compound 117-3.
Furthermore, the synthetic route disclosed by Phadke comprises a sequence of well-known organic transformations (e.g., Simmons-Smith reaction, dehydration reaction, hydrogenation reaction, etc.). A POSITA would have understood that such established synthetic reactions are routinely applied to structurally related compounds bearing different substituents and are not limited to a single, specifically exemplified substrate. Accordingly, absent evidence that the CH-for-N substitution at the X1 position would significantly alter the chemical reactivity of the intermediates to the point that it renders the reaction conditions disclosed by Phadke unsuitable, a POSITA would have reasonably expected the synthetic sequence disclosed by Phadke to be applicable to the preparation of compound-117-3.
Rejection Part 2:
Claim 24 is rejected under 35 U.S.C. 103 as being unpatentable over:
Phadke (WO2020051538A1; published March 12, 2020) in view of
Sabatino et al. (Sabatino) (Sabatino, G. et al. Assessment of new 6-Cl-HOBt based coupling reagents for peptide synthesis. Part 1: Coupling efficiency study. Letters in Peptide Science 2002, 9, 119-123.)
Phadke discloses the synthesis of the following compound:
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(herein, referred to as Phadke-compound-2; structure can be found in Phadke, abstract; Note: Phadke-compound-2 is also recited in instant claim 117). The synthetic steps required to prepare Phadke-compound-2 is detailed above in the “Claim Rejections - 35 USC § 102” section. The last few steps in preparing Phadke-compound-2 are also detailed above in the “Claim Rejections - 35 USC § 102” section and reiterated below for convenience:
Converting compound of instant formula (I) [Wingdings font/0xE0] formula (XI) [Wingdings font/0xE0] formula (XII)
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This scheme can be found on pg. 98.
The details of steps 1E and 2E can be found on pg. 98-99.
Here, the N-protecting-group-removing agent is hydrogen chloride (as recited in instant claim 24)
Converting compound of instant formula (XII) [Wingdings font/0xE0] formula (XIV)
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This scheme can be found on pg. 99.
The details of step 1F can be found on pg. 99.
The reagents used to couple compound 16 of Phadke (i.e., a compound of instant formula [XIII]) and compound 33 of Phadke (i.e., a compound of instant formula [XII]) is TBTU and DIPEA.
Note: Instant claim 24 recites using HATU as the coupling reagent instead of TBTU.
Besides TBTU, Phadke does not disclose other coupling reagents for carrying out the coupling reaction. However, Sabatino discloses that HATU (i.e., 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate as recited in instant claim 24) and TBTU are both well-known coupling reagents routinely employed for peptide bond formation (see Sabatino, abstract, 1st sentence). Thus, Sabatino recognizes HATU and TBTU as alternative reagents capable of performing the same coupling transformation.
Therefore, one of ordinary skill in the art would have found it prima facie obvious before the effective filing date of the claimed invention to substitute TBTU coupling reagent employed by Phadke with the HATU coupling reagent taught by Sabatino in order to perform the same peptide coupling reaction. Because Sabatino teaches that both HATU and TBTU are conventional peptide coupling reagents used for the same purpose, a POSITA would have reasonably expected HATU to function as a suitable alternative to TBTU in the reaction disclosed by Phadke with a reasonable expectation of success.
Note: The substitution of one known peptide coupling reagent for another known peptide coupling reagent capable of performing the same chemical transformation constitutes the predictable use of prior art knowledge. Such a substitution is merely a selection of one known equivalent reagent from a finite number of identified, predictable alternatives to achieve the expected result of amide bond formation.
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, 3, 5, 7, 9, 15, 17, 22-24, 31, 39, 41, 43, 67, 83, 85, 86, 104, and 117 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over:
claims 1-5, 10, 21, 23, 25, 30, 39, 41, 43, 73, 89, 91, 92, 110, 123, and 132 of U.S. Patent Application No. 18/719,261,
claims 1, 2, 8, 14, 21-23, 31, 33, 38, 41, 52, 68, 71, 88, 102, 103, 106, and 110 of U.S. Patent Application No. 19/138,289,
claims 1-66 of U.S. Patent Application No. 19/492,352,
claims 1-15 of U.S. Patent No. US 11,814,363 B2,
claims 1-11 of U.S. Patent No. US 11,084,800 B2,
claims 1-17 of U.S. Patent No. US 11,708,351 B2,
claims 1-20 of U.S. Patent No. US 12,162,860 B2,
claims 1-8 of U.S. Patent No. US 11,447,465 B2, and
claims 1-7 of U.S. Patent No. US 12,006,307 B2.
Although the claims at issue are not identical, they are not patentably distinct from each other because there is significant overlap between the instant claims and the claim sets from the issued patents and the co-pending applications.
Note: The prior art relied upon in the rejections under 35 USC § 102 and 35 USC § 103 includes PCT publication WO 2020/051538, which corresponds to U.S. patent No. 11,814,363 B2.
The cited applications and issued patents are directed either to:
methods of preparing compounds encompassed by instant claim 117 or methods of preparing compounds sharing the same core structural scaffold as those encompassed by instant claim 117OR
compounds sharing the same core structural scaffold as those encompassed by instant claim 117.
The co-pending applications and/or the issued patents directed to methods of preparation disclose synthetic routes that generally follow the synthetic strategy described in the instant application/instant claims (which have been anticipated and rendered obvious by WO 2020/051538 as explained above). Likewise, the co-pending applications and/or the issued patents directed to the compound claims necessarily rely upon synthetic methods consistent with the general synthetic approach disclosed in the instant application/instant claims to prepare the claimed compounds.
Although certain co-pending applications and/or issued patents may employ different reagents or reaction conditions in particular synthetic steps, they nevertheless utilize the same core intermediates and overall synthetic framework disclosed in WO 2020/051538 and in the instant claims. Selection of alternative reagents or routine modification of reaction conditions to prepare the same core intermediates would have been within the ordinary level of skill in the art and represents no more than routine optimization by a POSITA in the art. Accordingly, the instantly claimed subject matter does not define a patentably distinct invention over the cited co-ending applications and patents.
Conclusion
No claims are allowed. Any inquiry concerning this communication or earlier communications from the examiner should be directed to KRISTEN ROMERO whose telephone number is (571)272-6478. The examiner can normally be reached M-F 9:30 AM - 6:00 PM ET.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, JEFFREY H. 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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/KRISTEN W ROMERO/Examiner, Art Unit 1624
/JEFFREY H MURRAY/Supervisory Patent Examiner, Art Unit 1624
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