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 .
Applicant’s amendments and remarks filed October 6, 2025 have been received and reviewed. Claims 13-29 are now pending in this application.
Claim Rejections - 35 USC § 112
Claims 13-29 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.
i) It is noted that R1 is now limited to C2-C12 alkyl groups, optionally substituted, to overcome the prior art rejections of the previous office action. The group “alkenyl (C1-C12)” should also be amended to have at least two carbons (C2-C12) because al alkenyl cannot be made up only one carbon. The smallest alkenyl is ethenyl.
ii) The term “(hetero)aryl,” as well as, “carboxyl (hetero) aryl” are still indefinite because it is not known how many atoms are present, how many and what kind of heteroatoms are involved, what size ring is intended and how many rings are present. It is unclear what the purpose of the parentheses represents, are groups, such as a carboxyl substituted heteroaryl intended? A clarification is still required.
iii) Claim 14 depends from claim 13 but includes compounds not embraced by claim 13. Thus, the compounds “(18),” “(25)” and “(49)” lack antecedent basis in claim 13. Claim 14 is improperly dependent from claim 13.
Thousands of compounds still on the compound of claim 13. Thus, a complete search of the entire genus could not be performed. The compound of formula (I) can be reduced to compounds wherein R1 is ethyl, R2 is H and R3 is H.
Below are exemplary prior art rejections of formula (I).
Claim Rejections - 35 USC § 102
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
Claim 13 is rejected under 35 U.S.C. 102(a)(1) as being anticipated by Shin et al. (Chemistry Letters (1976), (10), 1063-6). The claim reads on the compounds depicted below. See Abstract.
RN 62317-56-0 CAPLUS
CN 2H-Azirine-2-carboxylic acid, 3-ethyl-, ethyl ester (CA INDEX NAME)
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143
265
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RN 62317-57-1 CAPLUS
CN 2H-Azirine-2-carboxylic acid, 3-propyl-, ethyl ester (CA INDEX NAME)
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143
298
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RN 62317-58-2 CAPLUS
CN 2H-Azirine-2-carboxylic acid, 3-(1-methylethyl)-, ethyl ester (CA INDEX
NAME)
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143
265
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.
Claim 13 is again rejected under 35 U.S.C. 102(a)(1) as being anticipated by Sakamoto et al. Organic Letters (2011), 13(24), 6374-6377). The claim reads on the compounds depicted below. See Abstract.
RN 1346635-64-0 CAPLUS
CN 2H-Azirine-2-carboxylic acid, 3-(2-phenylethyl)-, ethyl ester, (2S)-
(CA INDEX NAME)
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209
370
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RN 1346635-70-8 CAPLUS
CN 2H-Azirine-2-carboxylic acid, 3-[(1E)-2-phenylethenyl]-, ethyl ester,
(2S)- (CA INDEX NAME)
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228
370
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RN 1346635-71-9 CAPLUS
CN 2H-Azirine-2-carboxylic acid, 3-[(1E)-2-(4-methoxyphenyl)ethenyl]-,
ethyl ester, (2S)- (CA INDEX NAME)
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226
428
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RN 1346635-73-1 CAPLUS
CN 2H-Azirine-2-carboxylic acid, 3-[(1E)-2-(4-fluorophenyl)ethenyl]-, ethyl
ester, (2S)- (CA INDEX NAME)
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226
399
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.
Claim 13 is rejected under 35 U.S.C. 102(a)(1) as being anticipated by Hassner et al. (Journal of the American Chemical Society (1968), 90(11), 2869-75). The claim reads on the compound depicted below. See Abstract.
RN 18709-39-2 CAPLUS
CN 2H-Azirine, 3-(2-phenylethyl)- (CA INDEX NAME)
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131
250
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.
Claim 13 is rejected under 35 U.S.C. 102(a)(1) as being anticipated by Qi et al. (
Chemical Communications (Cambridge, United Kingdom) (2011), 47(27),7848-7850). The claim reads on the compound depicted below. See Abstract.
RN 1318796-75-6 CAPLUS
CN 2H-Azirine-2-carboxylic acid, 3-(2-phenylethyl)-, methyl ester (CA
INDEX NAME)
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159
338
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.
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.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to BRUCK KIFLE whose telephone number is (571)272-0668. The examiner can normally be reached 8 AM - 6 PM, M-F.
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October 24, 2025
/BRUCK KIFLE/Primary Examiner, Art Unit 1624
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