Notice of Pre-AIA or AIA Status
The present application is being examined under the pre-AIA first to invent provisions.
Claims 1-11, are pending in this application.
Claim Rejections - 35 USC § 103
The following is a quotation of pre-AIA 35 U.S.C. 103(a) which forms the basis for all obviousness rejections set forth in this Office action:
(a) A patent may not be obtained though the invention is not identically disclosed or described as set forth in section 102 of this title, if the differences between the subject matter sought to be patented and the prior art are such that the subject matter as a whole would have been obvious at the time the invention was made to a person having ordinary skill in the art to which said subject matter pertains. Patentability shall not be negatived by the manner in which the invention was made.
Claim 1, is rejected under pre-AIA 35 U.S.C. 103(a) as being unpatentable over Numata et al., EP 2674423 A1, which teaches the following reaction:
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, pp. 48, [0152], wherein the definitions of Ra, R3, R4, R7 embraced instant compound
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. The prior art also teaches compound
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, pp. 59, 7th formula, table 2, wherein Ra is H and Rb-1 is -CH(Me)S(O)2Me, pp. 68, line 15. See also the entire publication.
Having known that the definitions of Ra, R3, R4, R7, embraced compound S2b, that S2b is useful for making S3b, and knowing that S3b has “pesticidal utility against pests in phyla arthropoda, mollusca, and nematoda” (WO2019/236274, abstract), a POSA would have known and be motivated to claim compound S2b, at the time the invention was made, with reasonable expectation of success. Therefore, the claim is not allowable over the prior art.
Claims 2-11, are rejected under pre-AIA 35 U.S.C. 103(a) as being unpatentable over Yang et al., US 2015/0112075 A1, which teaches the following reaction:
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. In claims 2-4, 10, applicant claims the process of step b above, while in claims 5-9, 10-11, applicant claims step c. In step b, the prior art teaches Xl is Cl, OC(=O)-C1-4-alkyl, or a group that forms an activated carboxylic acid. The reaction is performed in the presence of a base, preferably, sodium bicarbonate, optionally in the presence of, e.g. a mixture of THF and water as solvent, etc. See [0011]-[0112].
In step c, compound 3a is preferably 3-bromopyridine, and the step is performed in the presence of copper(I) chloride, copper(II) chloride, or copper(I) iodide and a base selected from, e.g. potassium phosphate, potassium carbonate, NN’-dimethylethane-1,2-diamine, optionally in the presence of a polar solvent, e.g. selected from acetonitrile, dioxane or NN-dimethylformamide, etc. See [0014].
The starting reagents Sib (instant) and the thioether (prior art) are analogous starting materials.
However, the replacement of analogous starting material in a well-known process is prima facie obvious. In re Durden, 226 USPQ 359 (1985). See also In re Farkas, 152 USPQ 109 (1966). “Employing a different compound in a generally old reaction is prima facie obvious. Applicant must show evidence reaction would not be expected to take place or that the new substituents would behave in a manner different from those of the reference.” The reactions are the same: acylation of amino group (claims 1-4, 10), and substitution reaction of 3-bromo-pyridine with pyrazole (Br the leaving group), claims 5-11. According to the invention, and the prior art, the mechanisms of the reactions are the same, and no other parts of the starting materials are involved in the reactions. It is clear from the prior art that the structure of the starting material varies, e.g. the length of the alkyl chain and Rl.
Having known that analogous starting reagents are expected to have similar chemical reaction, and substituting one for another is a routine practice in the art, one of ordinary skill in the art would have known and be motivated to try an analogous starting reagent in the process by the prior art, at the time the invention was made with reasonable expectation of success. Therefore, the invention is not allowable over the combination of the prior art and knowledge well-known in the art.
Claims 5-9, 11, are rejected under pre-AIA 35 U.S.C. 103(a) as being unpatentable over Yang et al., US 2015/0112075 A1, further in view of Numata et al., EP 2674423 A1.
Yang et al., teaches the reaction scheme set forth above.
Numata et al., teaches similar reaction scheme set forth above.
Numata et al., further teaches a base is selected from pyridine (chemical properties of lutidine and 2-picoline resemble pyridine), diisopropylethylamine, triethylamine, sodium hydroxide, potassium hydroxide, sodium carbonate, cesium carbonate and sodium hydrogen carbonate; solvent is further selected from polar solvent, DMSO, THF, water, xylene, toluene, halo hydrocarbon: methylene chloride, dichloromethane. The solvents can be used alone or in combination of two or more, [0156]-[0157]. The instant starting material and the prior art are analogous compounds. See above 35 USC 103 rejection for further explanations. A POSA would have known and be motivated to use the bases and solvents by Numata et al., in the process by Yang et al, at the time the invention was made with reasonable expectation of success.
Telephone Inquiry
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Taofiq A. Solola, whose telephone number is (571) 272-0709.
If attempts to reach the examiner by telephone are unsuccessful, the examiner's supervisor, Andrew Kosar, can be reached on (571) 272-0913. The fax phone number for this Group is (571) 273-8300.
Any inquiry of a general nature or relating to the status of this application or proceeding should be directed to the Group receptionist whose telephone number is (571) 272-1600.
/TAOFIQ A SOLOLA/Primary Examiner, Art Unit 1625
October 21 2025