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 .
Response to Amendment
The amendment to claims 1, 4 – 10, 12, 14 and new claims 17 - 20, submitted June 25, 2026 is acknowledge and entered.
Response to Arguments
Applicant’s arguments, see page 10, filed June 25, 2026, with respect to the objection of claim 2 - 14 have been fully considered and are persuasive in view of the claim amendments. The objection of claim 2 - 14 has been withdrawn.
Applicant’s arguments, see page 11, filed June 25, 2026, with respect to rejection of claims 11 – 14 under 35 USC 112(b) have been fully considered and are persuasive in view of the cancellation of claims 11and 13, amendment to claims 12 and 14, and arguments presented. The rejection of claims 11 – 14 under 35 USC 112(b) has been withdrawn.
Applicant’s arguments, see page 11, filed June 25, 2026, with respect to the rejection of claim 16, dependent on claim 1, under 35 USC 101 and 112(b) have been fully considered and are persuasive in view of the cancellation of claim 16. The rejection of claim 16, dependent on claim 1, under 35 USC 101 and 112(b) has been withdrawn.
Applicant’s arguments, see page 12, filed June 25, 2026, with respect to the rejection of claims 1 – 3 and 8 – 10 under 35 USC 102(a)(a) have been fully considered and are persuasive in view of the claim amendment, cancellation of claims 2 and 3, and arguments presented. The rejection of claims 1 – 3 and 8 – 10 under 35 USC 102(a)(a) has been withdrawn.
Applicant's arguments, see pages 12 – 13, filed June 25, 2026, with respect to the rejection of claim 15 under 35 USC 103 in view of Rendine have been fully considered but they are not persuasive. The claims are rejected for the reasons set out in the previous Office Action and as set out below and is made final.
Applicant’s arguments, see pages 13 - 14, filed June 25, 2026, with respect to the rejection of claims 1 – 10 under 35 USC 103 in view of Kozlov have been fully considered and are persuasive in view of the claim amendment, cancellation of claims 2 and 3, and arguments presented. The rejection of claims 1 – 10 under 35 USC 103 has been withdrawn.
Claim Rejections - 35 USC § 103
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.
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.
Claim(s) 14 is rejected under 35 U.S.C. 103 as being unpatentable over Rendine et al. (WO 2020/183387).
The rejected claim covers, inter alia, a process of converting a compound of formula (V) to a compound of formula (VI).
Rendine discloses the following process on page 13 line 17 to page 14 line 6.
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Formula (XI) is equal to Applicant’s formula (V) and formula (I) is equal to Applicant’s formula (VI). The first step of the claimed process is a product by process step to obtain a known compound that is not structurally different from compound V of the claimed invention. R13 = H, C1 – C6 alkyl (pp. 13), R1 = methyl (pp. 1), R2 & R3 = H (pp. 1) and R4 = C3 – C7 cycloalkyl.
In light of the fact that there are no conversion processes disclosed, the difference between Rendine and the claimed invention is that it does not teach the invention with particularity so as to amount to anticipation (See M.P.E.P. §2131: "[t]he identical invention must be shown in as complete detail as is contained in the claim." Richardson V. Suzuki Motor Co., 868 F.2d 1226, 1236, 9 USPQ2d 1913, 1920 (Fed. Cir. 1989). The elements must be arranged as required by the claim, but this is not an ipsissimis verbis test, i.e., identity of terminology is not required. In re Bond, 910 F.2d 831, 15 USPQ2d 1566 (Fed. Cir. 1990).).
However, based on the above, Rendine teaches the elements of the claimed invention with sufficient guidance, particularity, and with a reasonable expectation of success, that the invention would be prima facie obvious to one of ordinary skill (the prior art reference teaches or suggests all the claim limitations with a reasonable expectation of success. (see M.P.E.P. § 2143).
Claim Rejections - 35 USC § 103
The text of those sections of Title 35, U.S. Code not included in this action can be found in above paragraph 10 - 12.
Claim(s) 15 is rejected under 35 U.S.C. 103 as being unpatentable over Rendine et al. (WO 2020/183387).
Claim 15 covers inter alia, compounds (V-1) to (V-(V).
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However, Rendine is discloses as having the following compound as described on page 8 at lines 10 – 15,
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Additonally, page 11 in Scheme 2, a compound having the above structure is prepared as formula (II) by a method known in prior art teachings.
The difference between Rendine and the claimed invention is that it does not teach the invention with particularity so as to amount to anticipation (See M.P.E.P. §2131: "[t]he identical invention must be shown in as complete detail as is contained in the ...claim." Richardson v. Suzuki Motor Co., 868 F.2d 1226, 1236, 9 USPQ2d 1913, 1920 (Fed. Cir. 1989). The elements must be arranged as required by the claim, but this is not an ipsissimis verbis test, i.e., identity of terminology is not required. In re Bond, 910 F.2d 831, 15 USPQ2d 1566 (Fed. Cir. 1990).).
However, based on the above, Rendine teaches the elements of the claimed invention with sufficient guidance, particularity, and with a reasonable expectation of success, that the invention would be prima facie obvious to one of ordinary skill (the prior art reference teaches or suggests all the claim limitations with a reasonable expectation of success. (see M.P.E.P. § 2143).
Response to Arguments
Applicant respectfully asserts that to arrive at the subject matter of claim 15, the person of ordinary skill would have to make selections from two lists in the disclosure of Rendine (R¹³ and R⁴), without explicit guidance or suggestion to do so.
In response, the Examiner states that the Rendine discloses the compounds of formulae (V-I) and (V-II). Further, compounds of Rendine have fungicidal activity with use in agricultural or horticulture compositions. Obviousness is based on similarity of structure and function entails motivation to make claimed compounds in expectation that compounds with similar structure will have similar properties. In this instance the compounds of claim 15 have similar structure and function.
The only remaining difference is formulae (V-II) and (V-IV). However, the ester formulae (V-I) and (V-II) can be easily converted to the alcohol by known process of reduction. As such, formulae (V-II) and (V-IV) are not considered inventive.
Claim Rejections - 35 USC § 103
Claim(s) 17 is rejected under 35 U.S.C. 103 as being unpatentable over Rendine et al. (WO 2020/183387).
Claim 17 covers, inter alia, compounds (VII-I), (VII-II), (VII-III) and (VII-IV) below:
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However, Rendine is discloses as having the following compound as described on page 8 line 20 to page 9 line 4;
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Additonally, in Rendine’s Scheme 6, a compound of (Xia) which corresponds to Applicant’s Formula (VII-I) and (VII-III). Scheme 6 discloses a process for preparing the compound and further converting the compound to its corresponding ester by methylation with a reagent such as dimethyl sulfate in the presence of a base such as K2CO3. In (Xia) R14 = methyl, R1 = methyl (pp. 1), R2 & R3 = H (pp. 1) and R4 = C3 – C7 cycloalkyl. Applicant’s disclosure teaches that the compounds of formulae (VII-I), (VII-II), (VII-III) and (VII-IV) can be converted to the compounds of formula (VI) with a methylating agent, like dimethyl sulfate in the presence of a base such as potassium carbonate. (Applicant’s specification page 16 line16 – 19).
Obviousness is based on similarity of structure and function entails motivation to make claimed compounds in expectation that compounds with similar structure will have similar properties. In this instance the compounds of claim 17 have similar structure and function.
The difference between Rendine and the claimed invention is that it does not teach the invention with particularity so as to amount to anticipation (See M.P.E.P. §2131: "[t]he identical invention must be shown in as complete detail as is contained in the ...claim." Richardson v. Suzuki Motor Co., 868 F.2d 1226, 1236, 9 USPQ2d 1913, 1920 (Fed. Cir. 1989). The elements must be arranged as required by the claim, but this is not an ipsissimis verbis test, i.e., identity of terminology is not required. In re Bond, 910 F.2d 831, 15 USPQ2d 1566 (Fed. Cir. 1990).).
However, based on the above, Rendine teaches the elements of the claimed invention with sufficient guidance, particularity, and with a reasonable expectation of success, that the invention would be prima facie obvious to one of ordinary skill (the prior art reference teaches or suggests all the claim limitations with a reasonable expectation of success. (see M.P.E.P. § 2143).
Allowable Subject Matter
Claims 1, 4 – 10, 12 and 18 – 20 are allowed.
The following is a statement of reasons for the indication of allowable subject matter: the Examiner has considered the amendment filed by Applicant on June 25, 2026 and the arguments therein. Applicant’s arguments were found persuasive; as such, the Examiner has withdrawn some of the rejections in the previous Office Action.
As it relates to independent claims 1 and 18, the closest prior art is Rendine. The method described in Rendine introduces the cycloalkyl group by Suzuki coupling of aryl bromide and boronic acid or ester in the presence of palladium catalyst. Then an additional step such as hydrogenation is required. However, this differs from the process of the instantly claimed invention, wherein the compound of formula (V) is obtained selective monoalkylation to obtain the meta isomer, formula (I), from otho cresol, followed by alkylation of the phenol moiety.
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.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to YATE' K. CUTLIFF whose telephone number is (571)272-9067. The examiner can normally be reached Monday-Friday (8:30 - 5:30).
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, Scarlett Y. Goon can be reached at (571) 270-5241. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/YATE' K CUTLIFF/Primary Examiner, Art Unit 1692
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