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 .
Priority
This application is a national stage application under 35 U.S.C. § 371 of
International Application No. PCT/US2020/059923, filed 11/11/2020, which claims the priority benefit of PRO Application No. 62/933,553, filed 11/11/2019.
Information Disclosure Statement
The information disclosure statements (IDS) submitted on 07/07/2022, and 09/20/2023 were filed in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statements are being considered by the examiner.
Election/Restrictions
Applicant's election with traverse of selecting the compound of formula II as Ethyl 3-bromo-1-(3-chloro-2-pyridinyl)-lH-pyrazole-5-carboxylate in the reply filed on 03/31/2025 is acknowledged. The traversal is on the ground(s) that that the claims are unified by a common inventive concept, specifically the method of preparation of compounds of Formula II. This is found not persuasive and the restriction requirement has been withdrawn.
Claims 1-20 are pending and are currently under examination.
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 of this title, 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 set forth in Graham v. John Deere Co., 383 U.S. 1, 148 USPQ 459 (1966), that are applied 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.
Claims 1-20 are rejected under 35 U.S.C. 103 as being unpatentable over Fagan et al. (WO 2006/102025 Al) in view of Lahm (Rynaxypyr TM: A new insecticidal anthranilic diamide that acts as a potent and selective ryanodine receptor activator).
The instant claims are directed to a method of preparing a compound of Formula II comprising forming a mixture of formula I, an oxidizing agent, and organic solvent followed by, heating, adding an acid, a second amount of formula I and completing the reaction.
Lahm et al. teach the synthesis of an insecticidal anthranilic diamide in which compound D12 is reacted with 2,3-dichloropyridine, K2C03, and DMF, at 125 °C (scheme 1, page 6275).
However, Lahm et al. fail to disclose the specific steps of forming a mixture of a compound of formula I (Lahm’s D12), heating the mixture, adding a solvent and adding a second amount of a compound of formula I to complete the reaction.
Fagan et al. teach preparation of ethyl 3-bromo-1-(3-chloro-2-pyridinyl)-4,5-dihydro-lH-pyrazole-5- Carboxylate in example 3 and on examples 3-1 to 3-38 on table 1 (page 27-28). Fagan also discloses the yields for examples 3-1 through 3-38 wherein examples 3-30, 3-34 and 3-38 result in a high yield of 100% (table 1, page 28-29). Fagan also discloses hydrogen peroxide and potassium persulfate as preferred oxidants (page 1, lines 15-19). Fagan also teaches a compound of formula I is useful as an intermediate to insecticides (page 1, lines 10-15). Fagan teaches a mole ratio of a bromine oxidant to formula 2 in an amount of 1 to 3 and addition of bromine over a period of 0.5-20 hours (page 20, lines 12-20). Fagan also discloses the use of ethers including and polar aprotic solvents (page 22, lines 17-19). Fagan teaches the use of hydrochloric and sulfuric acids (page 31, line 28 – page 32, line 3). Fagan also teaches a range of solvent to compound ratio of 50:1 to 5:1 and that reaction temperatures range from 80 °C to 180 °C (page 20, lines 1-20). Fagan also teaches the use of a mechanical stirrer and a dropwise addition of bromine dissolved in dichloromethane in example 1 (page 25, lines 10-16). Fagan teaches a second addition of tertiary amine (formula 3) and methane sulfonyl chloride (page 32, lines 4-11 and scheme 7). Fagan also discloses the compound of ethyl 3-bromo-1-(5-broino-3-chloro-2-pyridinyl)-lH-pyrazole-5-carboxylate (Formula 10) and ethyl 3-bromo-1-(3-chloro-2-pyridinyl)-4,5-dihydro-1H-pyrazole-5-carboxylate (Formula 7) in example 1A (Page 26, line 30 to page 27, line 7). Fagan also discloses “Without further elaboration, it is believed that one skilled in the art using the preceding description can utilize the present invention to its fullest extent. The following Examples are focused on the bromination of 3-bromo-l-(3-chloro-2-pyridinyl)-4,5-dihydro-lH-pyrazole-5-carboxylate as outlined in Scheme 6. There are three possible products (Formulae 8, 9 and 10) when bromine is used as oxidant for the oxidation of the 2-pyrazoline of Formula 7. These Examples are to be construed as merely illustrative and not limiting of the disclosure in any way whatsoever.” (page 24, lines 22-28).
Therefore, it would have been prima facie obvious to a person of ordinary skill in the art, prior to the effective filing date of the claimed invention, to combine the teaching of Lahm and Fagan for several reasons beginning with each of the prior art teaching of Lahm and Fagan are within the same general field of insecticides and both Lahm and Fagan teach a reaction wherein the starting material is a compound of formula I and the product is a compound of formula II. A skilled artisan would have recognized that the two methods taught by Lahm and Fagan were useful in producing high yields of products from the reactions.
The compounds of D12 (Applicants formula I) and D13 (applicants formula II) in Lahm satisfy the structural limitations of the instant claims where R1/R8 is H or a C1-C4 alkyl, R2-R7 are H or a Halogen. The compound of ethyl 3-bromo-1-(5-broino-3-chloro-2-pyridinyl)-lH-pyrazole-5-carboxylate (Formula 10) and ethyl 3-bromo-1-(3-chloro-2-pyridinyl)-4,5-dihydro-1H-pyrazole-5-carboxylate (Formula 7) by Fagan also satisfy the structural limitations of the instant claims where R1/R8 is H or a C1-C4 alkyl, R2-R7 are H or a Halogen
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A person having ordinary skill in the art would have been motivated to combine the teachings of Lahm and Fagan because of the high yields demonstrated by the prior art whereby yields of 100% were achieved multiple times. A skilled artisan would have routinely optimized the reactions taught by Lahm and Fagan using traditional methods of improving yields known in the art including addition of an excess of one reactant, adjusting temperature so as to push the reaction to the desired product(s) and achieve desired yield(s). See MPEP 2144.05(II). Fagan also disclosed a second addition of a reactant in scheme 7. Based on scheme 7, a skilled artisan would have been motivated to add a second addition of a reactant with a reasonable expectation of success to prepare a compound of formula I into a compound of formula II. See MPEP 2143.
Conclusion
All claims are rejected. No claims are allowed.
Correspondence
Any inquiry concerning this communication or earlier communications from the examiner should be directed to ERNESTO VALLE JR whose telephone number is (703)756-5356. The examiner can normally be reached 0730-1700 M-F EST, 1st Friday off.
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/E.V./Examiner, Art Unit 1623
/ADAM C MILLIGAN/Supervisory Patent Examiner, Art Unit 1623