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
The amendments to the claims filed December 14, 2023 are acknowledged and entered. Claims 1-15 are pending.
Priority
This application is a 371 of PCT/EP2022/068443, filed July 4, 2022, which claims priority of EP21184514.4, filed July 8, 2021.
Information Disclosure Statement
Acknowledgement is made of the Information Disclosure Statement filed on February 7, 2025. All references have been considered except where marked with a strikethrough.
Specification
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 of the errors of which applicant may become aware of in the specification.
Election/Restriction
Applicant’s election without traverse of Group I (claims 1-6, drawn to chiral 3-sulfinylbenzoic acids of the respective absolute configuration given in formulae (I-R) and (I-S)) in the reply filed on April 23, 2026 is acknowledged. Claims 7-15 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention, there being no allowable generic or linking claim. Election was made without traverse in the reply filed on April 23, 2026.
Claim Objections
Claim 2 is objected to because of the following informalities:
Claim 2 is objected to for reciting duplicate definitions of R’. The claim recites R’ is methyl, ethyl, c-Pr, CH2-cPr, CH2CH2OMe, c-Pr, CH2-cPr or CH2CH2OMe. It appears that c-Pr, CH2-cPr and CH2CH2OMe are written twice. It is suggested that the duplicate definitions be deleted from the claim.
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.
Claim(s) 1-6 is/are rejected under 35 U.S.C. 103 as being unpatentable over Ahrens et al. (US 7,932,211)(hereinafter “Ahrens”).
The claims are drawn to chiral 3-sulfinylbenzoic acids of the respective absolute configuration given in formulae (I-R) and (I-S).
Ahrens teaches compounds of Formula (IIIb) which correspond to racemic mixtures of the claimed compounds (See Table E; compounds No. 5-9 to 5-16 and 5-33 to 5-40). For instance, compound No. 5-9 (see first entry of Table E; pictured below for convenience) corresponds to the claimed compounds wherein X is Me; R’ is Me; and Z is CF3. The compounds of Ahrens contain the chiral sulfinyl group of the claims and therefore consist of both formulae (I-R) and (I-S) stereoisomers of the claims. Ahrens teaches the compounds are useful in the synthesis of compounds of formula (I) which have herbicidal activity (Schemes 1 and 2; col 6, lines 1-5, formula (III) is prepared from formula (IIIb); col 6, lines 25-30, compounds of formula (I)…have excellent herbicidal activity; Table A, compounds No. 1-9 to 1-16, 1-33 to 1-40). Ahrens teaches compounds of formula (I) exist as stereoisomers and that stereoisomers may be prepared selectively by using stereoselective reactions employing optically active starting materials and/or auxiliaries (col 3, lines 15-30). According to the synthetic methods for preparing formula (I) (see Schemes 1 and 2 as noted above, formula (III) is prepared from formula (IIIb)), the optically active starting materials referred to by Ahrens would correspond to compounds of instant formula (I-R) and (I-S) for the reason that these are the only optically active (chiral) starting material taught by Ahrens for synthesizing formula (I). Regarding enantiomeric excess, the selective preparation of a stereoisomer of formula (I) would require that the ee of the optically active starting material is high, including at least as high as 99% as required by claims (see claims 5-6).
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The difference between the prior art and the instant claims is that the instant claims recite the individual stereoisomers of formulae (I-R) and (I-S) which are present in the prior art as a racemic mixture. However, the claimed stereoisomers would have been prima facie obvious to one having ordinary skill in the art before the effective filing date of the instant application because Ahrens had disclosed that stereoisomers of formula (I) could be prepared from optically active (chiral) starting materials, and these optically active starting materials would have corresponded to the presently claimed compounds of formulae (I-R) and (I-S). The only optically active starting material in the preparation of formula (I) according to Scheme 1 or 2 would have been a starting material prepared from racemic formula (IIIb). Optically active starting materials prepared from formula (IIIb) would have been formulae (I-R) and (I-S) of the claims.
One would have been motivated as a matter of preparing specific stereoisomers of the herbicidal compounds of formula (I) disclosed by Ahrens.
One would have had a reasonable expectation of success because Ahrens had disclosed that stereoisomers of formula (I) could be prepared from optically active (chiral) starting materials. In the preparation of stereoisomers of formula (I) according to Schemes 1 or 2 one skilled in the art would have possessed a compound of formulae (I-R) or (I-S) as is claimed.
Note: Numerous other prior art references have been identified which collectively teach hundreds of compounds that are racemic mixtures of the claimed compounds and therefore render the claims obvious for similar reasons to those discussed in the above rejection. In the present cast, the Examiner has rejected the claims in view of the oldest reference.
Conclusion
No claim is allowed.
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May 20, 2026
/KEVIN S MARTIN/Examiner, Art Unit 1624
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