DETAILED ACTION
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 .
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.
Claims 1, 6, and 19 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Shchepochkin et al. (RSC Adv. 2016, 6, 77834-77840).
Considering Claims 1, 6, and 19: Shchepochkin et al. teaches a compound of the formula
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146
104
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, where R is CN (Scheme 3) and the counter ion is BF4- (Scheme 4).
Claim 4 is rejected under 35 U.S.C. 102(a)(1) as being anticipated by Shchepochkin et al. (RSC Adv. 2016, 6, 77834-77840).
Considering Claim 4: Shchepochkin et al. teaches a compound of the formula
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146
104
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, where R is CN (Scheme 3) and the counter ion is BF4- (Scheme 4).
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.
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.
Claim 3 are rejected under 35 U.S.C. 103 as being unpatentable over Rumble et al. (The Journal of Chemical Physics, 148, 193801, 2018).
Considering Claims 3: Rumble et al. teaches a compound of the formula
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306
156
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where the anion is hexafluorophosphate (pg. 193801-1-2).
Rumble et al. does not teach the phenyl group as being substituted at the position of R1 in formula II. However, a prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities. "An obviousness rejection based on similarity in chemical structure and function entails the motivation of one skilled in the art to make a claimed compound, in the expectation that compounds similar in structure will have similar properties." In re Payne, 606 F.2d 303, 313, 203 USPQ 245, 254 (CCPA 1979). Compounds which are position isomers (compounds having the same radicals in physically different positions on the same nucleus) or homologs (compounds differing regularly by the successive addition of the same chemical group, e.g., by -CH2- groups) are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties. In re Wilder, 563 F.2d 457, 195 USPQ 426 (CCPA 1977). See MPEP § 2144.09. It would have been obvious to a person of ordinary skill in the art to have prepared a compound with the phenyl substituent at the R3 position based on the compound of Rumble et al., and the motivation to do so would have been, a person of ordinary skill in the art would expect the compounds to function similarly based on the close structural similarity.
Claim 3 is rejected under 35 U.S.C. 103 as being unpatentable over Chupakhin et al. (Chemistry of Heterocyclic Compounds, 2019, 55(1), 956-963).
Considering Claim 3: Chupakhin et al. teaches a compound of the formula
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82
104
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, where X is
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56
76
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and R is F (Figure 1, Abstract).
Chupakhin et al. does not teach the phenyl group as being substituted at the position of R1 in formula II. However, a prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities. "An obviousness rejection based on similarity in chemical structure and function entails the motivation of one skilled in the art to make a claimed compound, in the expectation that compounds similar in structure will have similar properties." In re Payne, 606 F.2d 303, 313, 203 USPQ 245, 254 (CCPA 1979). Compounds which are position isomers (compounds having the same radicals in physically different positions on the same nucleus) or homologs (compounds differing regularly by the successive addition of the same chemical group, e.g., by -CH2- groups) are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties. In re Wilder, 563 F.2d 457, 195 USPQ 426 (CCPA 1977). See MPEP § 2144.09. It would have been obvious to a person of ordinary skill in the art to have prepared a compound with the fluorine substituent at the R3 position based on the compound of Chupakhin et al., and the motivation to do so would have been, a person of ordinary skill in the art would expect the compounds to function similarly based on the close structural similarity.
Allowable Subject Matter
Claim 5 is allowed.
The following is an examiner’s statement of reasons for allowance: The prior art of record does not teach or suggest the claimed structure where the compound is substituted with the specific substituents at the two claimed positions on the phenyl group. The closest prior art is Rumble et al. and Chupakhin et al., discussed above. Neither reference teaches the phenyl group as being disubstituted and there is no suggestion or teaching in the art to modify the reference to add a second subsituent. As such, the instant claimed structure is non-obvious over the closest prior art of record.
Any comments considered necessary by applicant must be submitted no later than the payment of the issue fee and, to avoid processing delays, should preferably accompany the issue fee. Such submissions should be clearly labeled “Comments on Statement of Reasons for Allowance.”
Response to Arguments
Applicant's arguments filed June 4, 2026 have been fully considered but they are not persuasive, because:
A) The applicant’s argument that there is no motivation to modify Rumble et al. or Chupakhin et al. to arrive at the structure of claim 3 is not persuasive. The claimed structure is a position isomer of the structures disclosed in the prior art. a prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities. "An obviousness rejection based on similarity in chemical structure and function entails the motivation of one skilled in the art to make a claimed compound, in the expectation that compounds similar in structure will have similar properties." In re Payne, 606 F.2d 303, 313, 203 USPQ 245, 254 (CCPA 1979). Compounds which are position isomers (compounds having the same radicals in physically different positions on the same nucleus) or homologs (compounds differing regularly by the successive addition of the same chemical group, e.g., by -CH2- groups) are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties. In re Wilder, 563 F.2d 457, 195 USPQ 426 (CCPA 1977). See MPEP § 2144.09.
Conclusion
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). 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.
Correspondence
Any inquiry concerning this communication or earlier communications from the examiner should be directed to LIAM J HEINCER whose telephone number is (571)270-3297. The examiner can normally be reached M-F 7:30-5:00.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Mark Eashoo can be reached at 571-272-1197. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/LIAM J HEINCER/Primary Examiner, Art Unit 1767
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