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 .
Status of Claims
Claims 1-19 are pending in the instant application. Claims 1 and 11 are amended and claims 20-21 are cancelled via the amendment filed October 27th, 2025.
Priority
This is a 35 U.S.C. 371 National Stage filing of International Application No. PCT/IB2021/050935 filed February 5th, 2021, which claims priority under 35 U.S.C. 119(a-d) to IN202021056370, filed December 24th, 2020. Receipt is acknowledged of papers submitted under 35 U.S.C. 119(a)-(d).
Withdrawn Rejections
Applicant’s arguments, filed October 27th, 2025, with respect to the 35 U.S.C. 102 rejection of claims 20-21 over Lahm have been fully considered and are persuasive. The 35 U.S.C. 102 rejection of claims 20-21 has been withdrawn.
Applicant has overcome this rejection by cancelling claims 20-21.
Maintained Rejections
Applicant's arguments filed October 27th, 2025, with respect to the 35 U.S.C. 102 rejection claims 1-3 and 5-10 over Shapiro have been fully considered but they are not persuasive. See response to remarks.
Applicant's arguments filed October 27th, 2025, with respect to the 35 U.S.C. 103 rejection claims 1-10 over Shapiro and Li have been fully considered but they are not persuasive. See response to remarks.
Applicant's arguments filed October 27th, 2025, with respect to the 35 U.S.C. 103 rejection claims 11-19 over Lahm and Panchal have been fully considered but they are not persuasive. See response to remarks.
Response to Remarks
On p. 7 of the remarks, Applicant argues that the 35 U.S.C 102 rejection of claims 1-3 and 5-10 over Shapiro is moot in view of the claim amendments.
In response, the amendment is not sufficient to overcome the rejection. Applicant has amended claim 1 to include the limitation that Formula II is converted to the compound of Formula I “by utilizing methylamine”. As stated in the previous Office action, methylamine is used in the reaction of compounds of instant formula III and IV to produce a compound of instant formula I.
On p. 8-9 of the response, Applicant argues that Shapiro teaches an amide coupling mechanism, whereas the instant invention claims a process involving a benzooxazinone ring-opening mechanism using methylamine.
In response to this argument, instant claim 1 only requires reacting formula III and formula IV to form formula II and then utilizing methylamine to form the compound of instant formula I. As stated in the previous Office action, Shapiro teaches a reaction that involves reacting a compound of formula III and IV and methylamine to form a compound of instant formula I. Shapiro does not explicitly teach that the compound of formula II was formed, however, as the same reactants are used in both instant claim 1 and the prior art, it is inherent and necessary that a compound of formula II will also be formed. See MPEP 2112.
On p.11 of the remarks, Applicant argues that the process as claimed in the present application confers key technical advantages.
In response, the Examiner has considered this argument fully but must disagree that the advantages overcome the previous rejection for the following reasons.
Whether the unexpected results are the result of unexpectedly improved results or a property not taught by the prior art, the “objective evidence of nonobviousness must be commensurate in scope with the claims which the evidence is offered to support.” In other words, the showing of unexpected results must be reviewed to see if the results occur over the entire claimed range. In re Clemens, 622 F.2d 1029, 1036, 206 USPQ 289, 296 (CCPA 1980). See MPEP 716.02 (d) and MPEP 716.02 (e).
An affidavit or deceleration under 37 CFR 1.132 must compare the claimed subject matter with the closes prior art to be effective to rebut a prima facie case of obviousness. In re Burckel, 592 F.2d 1175, 201 USPQ 67 (CCPA 1979).
Applicant refers to alleged unexpected, surprising results; however, even if the results were considered unexpected, the results would not be commensurate in cope with the scope of the claims.
Applicant argues on p.11 that the instantly claimed process confers an enhance yield and purity. Applicant argues that the process routinely achieves yields over 85%. Applicant further argues that economic advantages and simplicity in scalability.
In response, the results provided do not occur over the entire claimed range (any amount of Formulas I-IV) of present claim 1. In the instant specification, specific amounts of each compound were used, however, the present claims do not require a specific amount for each compound in the instant reaction.
On p. 12-13 of the response, Applicant argues that Panchal does not constitute proper prior art for assessing inventive step.
In response, while the effective filing date of the instant application is December 24th, 2020, as priority is claimed to IN202021056370, Panchal claims priority to IN 202021006036, filed February 12th, 2020. As Panchal is a WO document, having designated the US, it gains the benefit of priority to a document filed before the instant application’s effective filing date, Panchal qualifies as prior art having priority to Feb. 12, 2020, to be used against the instant application, and is not limited to its publication date.
For the reasons above, the rejections are maintained.
Maintained Claim Rejections - 35 USC § 102
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 the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
Claim(s) 1-3 and 5-10 stand rejected under 35 U.S.C. 102(a)(1) as being anticipated by Shapiro et al (WO 2006/062978, as cited on the IDS).
Shapiro teaches a process for the preparation of the following compound (Example 7):
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, this compound is embraced by Formula I of the instant application, wherein R is Cl.
Shapiro teaches that the process of preparation includes reacting
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to form
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(Example 2).
Shapiro then teaches that
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and aqueous methylamine is used to form
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.
Shapiro then teaches that
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is mixed with
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, acetonitrile, 3-picoline and methanesulfonyl chloride to form
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. See scheme below for clarity.
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Thus, Shapiro teaches a compound of instant formula III (compound 4 in the reaction scheme) and a compound of instant formula IV (compound 1 in the reaction scheme) are used to produce a compound of instant formula I (compound 5 in the reaction scheme.
Shapiro does not explicitly teach that the benzoxazinone of instant Formula II is formed within the reaction, however, as the same reactants as instantly claimed are used to prepare the compound of instant Formula I, it is inherent that the intermediate compound would have formed within the reaction process.
Regarding claims 1 and 9, as such, Shapiro teaches a compound of instant formula III and a compound of instant formula IV are used to produce a compound of instant formula I, without the benzoxazinone compound of instant formula II being isolated after its formation.
Regarding claim 2, as seen above, Shapiro teaches that the process of preparation includes the use of methanesulfonyl chloride.
Regarding claims 3 and 5-6, as seen above, Shapiro teaches that the base in the process of preparation is 3-picoline.
Regarding claims 7-8, as seen above, Shapiro teaches that the solvent used in the process of preparation is acetonitrile.
Regarding claim 10,as seen above, Shapiro teaches that the process of preparation includes the use of aqueous methylamine.
Maintained 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) 1-10 stand rejected under 35 U.S.C. 103 as being unpatentable over Shapiro et al (WO 2006/062978, as cited on the IDS) in view of Li et al (US 2010/0317864, as cited on the IDS).
Determining the scope and contents of the prior art. (See MPEP § 2141.01)
Shapiro teaches a process for the preparation of the following compound (Example 7):
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, this compound is embraced by Formula I of the instant application, wherein R is Cl.
Shapiro teaches that the process of preparation includes reacting
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to form
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(Example 2).
Shapiro then teaches that
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and aqueous methylamine is used to form
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.
Shapiro then teaches that
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is mixed with
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, acetonitrile, 3-picoline and methanesulfonyl chloride to form
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. See scheme below for clarity.
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Thus, Shapiro teaches a compound of instant formula III (compound 4 in the reaction scheme) and a compound of instant formula IV (compound 1 in the reaction scheme) are used to produce a compound of instant formula I (compound 5 in the reaction scheme.
Shapiro does not explicitly teach that the benzoxazinone of instant Formula II is formed within the reaction, however, as the same reactants as instantly claimed are used to prepare the compound of instant Formula I, it is inherent that the intermediate compound would have formed within the reaction process.
Regarding claims 1 and 9, as such, Shapiro teaches a compound of instant formula III and a compound of instant formula IV are used to produce a compound of instant formula I, without the benzoxazinone compound of instant formula II being isolated after its formation.
Regarding claim 2, as seen above, Shapiro teaches that the process of preparation includes the use of methanesulfonyl chloride.
Regarding claims 3 and 5-6, as seen above, Shapiro teaches that the base in the process of preparation is 3-picoline.
Regarding claims 7-8, as seen above, Shapiro teaches that the solvent used in the process of preparation is acetonitrile.
Regarding claim 10,as seen above, Shapiro teaches that the process of preparation includes the use of aqueous methylamine.
Ascertainment of the differences between the prior art and the claims. (See MPEP § 2141.02)
The prior art is deemed to anticipate instant claims 1-3 and 5-10 where anticipation is the epitome of obviousness. In re Pearson, 494 F.2d 1399, 1402 (CCPA 1974)). Shapiro does not teach that the base used in the process of preparation is an organic base.
Finding of prima facie obviousness --- rationale and motivation (See MPEP § 2142-2143)
However, Li teaches the following process of preparation (paragraph [0043]):
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.
This process of preparation includes the same reactants used by Shapiro to produce the compound of instant formula I. Shapiro teaches that the base, sodium bicarbonate is used to produce the compound of instant formula I (paragraph [0044]).
Regarding claims 3-4, one of ordinary skill in the art would have been motivated to use the base, sodium bicarbonate in the process of preparation taught by Shapiro and would have a reasonable expectation of success as Li teaches a process of preparation for a compound of instant formula I with the use of sodium bicarbonate as the base.
Claim(s) 11-19 stand rejected under 35 U.S.C. 103 as being unpatentable over Lahm et al (Bioorganic & Medicinal Chemistry Letters 17 (2007) 6274–6279) in view of Panchal et al (WO 2021/161200 A1, which claims priority to IN 202021006026 filed 02/12/2020, (previously made of record).
Determining the scope and contents of the prior art. (See MPEP § 2141.01)
Lahm teaches a process for the preparation of the following compound, D3 (Table 1):
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, wherein R1 is Cl, R2 is Me and R3 is Br.
This compound is embraced by formula I of the instant application, wherein R is Cl.
Lahm teaches that the process includes the following steps (Scheme 1):
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.
Compound 5 as taught by Lahm is embraced by Formula II of the instant application. Compound 6 as taught by Lahm is embraced by Formula IV of the instant application, wherein R is Cl. Compound 7 as taught by Lahm is embraced by Formula II of the instant application, wherein R is Cl. Compound 8 as taught by Lahm is embraced by Formula I of the instant application, wherein R is Cl.
Further, Lahm teaches that the process includes MeSO2Cl, Et3N and MeCN.
Ascertainment of the differences between the prior art and the claims. (See MPEP § 2141.02)
The prior art does not teach a single embodiment wherein the process of preparation of a compound of instant formula I includes filtering the reaction mixture to yield a wet filter-cake comprising instant formula II and telescoping the wet filter-cake with methylamine to produce the compound of Formula I.
Finding of prima facie obviousness --- rationale and motivation (See MPEP § 2142-2143)
However, Panchal teaches a one pot process for the preparation of anthranilamide compounds. Panchal teaches a one pot process for the preparation of chlorantraniliprole, having the following formula (Example 1, which find support on page 22 of the priority document):
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.
This compound is embraced by formula I of the instant application, wherein R is Cl.
Panchal teaches that the process of preparation includes forming a reaction mixture with the following compounds:
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and
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.
Panchal teaches that the reaction mixture was stirred until the competition of the reaction. Panchal then teaches that the reaction mixture was then purged with methyl amine gas and then filtered. Panchal teaches that after filtering, a wet cake was obtained and then filtered (Example 1, which finds support on page 22 of the priority document).
Further, Panchal teaches that the development of this process was needed as current known methods have processes that lead the purification of the product and handling of effluent to become cumbersome (page 3, paragraph 1; which finds support on page 2, paragraph 3 of the priority document).
Regarding claim 11, as Lahm teaches a process for the preparation of a compound of instant formula I, with a compound of instant formulas III and IV, and methanesulfonyl chloride, one of ordinary skill in the art would have been motivated to filter the reaction mixture to yield a wet filter-cake comprising instant formula II and telescoping the wet filter-cake with methylamine to produce the compound of Formula I and would have a reasonable expectation of success AS Panchal teaches a one pot synthesis of a compound of Formula I that comprises filtering the reaction mixture and telescoping the reaction mixture with methylamine.
Regarding claim 12, as seen above, Lahm teaches that the method includes the use of methanesulfonyl chloride.
Regarding claims 13 and 15, as seen above, Lahm teaches that the base used in triethylamine.
Regarding claims 14 and 16, Panchal teaches that a preferred base in the process for preparing the compound of instant formula I is sodium carbonate or potassium carbonate (page 19, paragraph 4, which finds support on page 12, paragraph 10 of the priority document). As such, one of ordinary skill in the art would have been motivated to use sodium carbonate or potassium carbonate in the method as Panchal teaches them as a preferred base.
Regarding claims 17-18, as seen above, Lahm teaches that the process includes the use of acetonitrile.
Regarding claim 19, Panchal teaches that the process of preparation of a compound of instant formula I is carried out by using methyl amine gas or methyl amine aqueous solution (page 19, which finds support on page 14 of the priority document). As such, one of ordinary skill in the art would have been motivated to use an aqueous solution of methyl amine as Panchal teaches that either can be used to carry out the process.
Correspondence
THIS ACTION IS MADE FINAL. 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.
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/A.G.K./Examiner, Art Unit 1626
/FEREYDOUN G SAJJADI/Supervisory Patent Examiner, Art Unit 1699