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 .
DETAILED ACTION
Status of 18/260,567
Claims 1-23 are currently pending.
Priority
Instant application 18/260,567, filed 7/6/2023, claims priority as follows:
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Receipt of the foreign priority application is acknowledged.
Information Disclosure Statement
All references from the IDS submitted on 7/6/2023 have been considered unless marked with a strikethrough.
Response to Arguments/Amendments
The amendment filed 7/23/2026 has been entered. Claims 1, 2, 10, 12, and 20 have been amended. No claims have been cancelled or added.
In the Non-Final dated 4/23/2026, the abstract was objected to for insufficient length. In response, Applicant submitted a new abstract that meets the requirements, which overcomes the rejection. Thus, the objection is withdrawn.
The drawings were objected to in the Non-Final dated 4/23/2026 for pixelated and illegible images. In response, Applicant has submitted replacement drawings. However, the drawings remain pixelated and illegible, and the objection is maintained.
Claims 1, 2, 10, 12, and 20 were objected to in the Non-Final dated 4/23/2026. Applicant has amended claim 2 to correct a minor informality, which overcomes the objection, and has submitted replacement figures in the claims. Figures 10 and 12 are now legible, which overcome the objection; however, replacement figures of claim 1 and 20 remain pixelated and illegible, and the objection of claims 1 and 20 is maintained. The objections of claims 2, 10, and 12 are withdrawn.
Claims 1-2, 4-8, 10-12, and 20-21 were rejected under 35 U.S.C. 103 in the Non-Final dated 4/23/2026. In response, Applicant argues that the cited combination does not teach or suggest that process wide solvent selection of a halogenated hydrocarbon solvent. Further, Applicant states Comparative Example 4, of the instant disclosure, uses toluene to generate the compound Formula B1 in 88.7% purity and with a 1.13% Formula B3 impurity, and that the cited art does not recognize this impurity problem or suggest the solvent substitutions of the prior art as its solution. The compound Applicant compared Comparative Example 4 to in the response dated 7/23/2026 is the final product chlorantraniliprole, which is not a valid head to head comparison. However Example 1 of the instant disclosure (page 21, lines 4-14), describes the preparation of compound Formula B1 in dichloromethane, which is a valid head to head comparison. Example 1 discloses the synthesis of a compound Formula B1 in a 92% purity with only 0.3% Formula B3, which can be considered an unexpected result and an improvement upon the existing method, which overcomes the rejection of claims 1-2, 4-8, and 11-12. No such data has been identified for the conversion of Formula D to Formula E. Thus, the rejection of claims 1-2, 4-8, and 11-12 is withdrawn, and the rejection of claims 20-21 is maintained.
Claims 1-2, 5-6, 8, and 20-21 were provisionally rejected on the ground(s) of nonstatutory double patenting in the Non-Final dated 4/23/2026. In response, Applicant requested that the double patenting rejection be held in abeyance. This request is acknowledged. However, Applicant is reminded that the Office cannot hold a rejection in abeyance and “[i]n order to be entitled to reconsideration or further examination, the applicant or patent owner must reply to the Office action. The reply by the applicant or patent owner must be reduced to a writing which distinctly and specifically points out the supposed errors in the examiner's action and must reply to every ground of objection and rejection in the prior Office action.” Because Applicant has failed to present an amendment or argument that overcomes the present rejection, the provisional rejection is maintained. Any future submissions that fail to address the merits of the non-statutory double patenting rejection might be deemed to be non-responsive. The Examiner notes that the ‘970 Application has since been issued, and will now be referred to as both the U.S. Patent No. 12,643,874 and the ‘874 Patent.
Additionally, Applicant’s amendments necessitated the new ground(s) of rejection presented in this Office Action.
Election/Restriction
Applicant’s election of Group I, claims 1-12 and 20-21, drawn to a process for the preparation of an anthranilamide compound of Formula E, without traverse in the reply filed 12/10/2025 is acknowledged. Applicant’s election of chlorantraniliprole, with traverse, in the same reply, is also acknowledged. The Examiner notes chlorantraniliprole:
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reads on instant Formula E:
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When X1 is Br, X2 is Cl, X4 is Cl, and R’ is methyl. The traversal is on the grounds that the reference Eurofins Advinus Limited (WO 2021/033172 A1, cited in the IDS of 7/6/2023, herein after “Eurofins”) of the Requirement for Restriction/Election of Species of 11/14/2025 is not valid prior art because it has the publication date of February 26th, 2021, whereas the instant claims have an effective filing date of January 11th, 2021. However, the reference Eurofins qualifies as prior art under 35 U.S.C. 102(a)(2) because the filing date of Eurofins is September 30th, 2020, which is before the effective filing date of the instant claims. Additionally, Applicant argues the election of species requirement is not proper because Eurofins does not disclose the amination step as recited in the instant claims. Applicants arguments have been considered, but are not persuasive because an obviousness argument can be made with Eurofins in view of additional references. See the 103 rejections below. The requirement is still deemed proper and is therefore made FINAL.
Examination will begin with the elected species. In accordance with MPEP § 803.02, if upon examination of the elected species, no prior art is found that would anticipate or render obvious the instant invention based on the elected species, the search of the Markush-type claim will be extended. If prior art is then found that anticipates or renders obvious the non- elected species, the Markush-type claim will be rejected. It should be noted that the prior art search will not be extended unnecessarily to cover all non-elected species. Should Applicant overcome the rejection by amending the claim, the amended claim will be examined again. The prior art search will be extended to the extent necessary to determine patentability of the Markush-type claim. In the event prior art is found during further examination that renders obvious or anticipates the amended Markush-type claim, the claim will be rejected and the action made final.
In the Non-Final dated 4/23/2026, the elected species was searched and prior art was identified. The 103 rejections of claims 1-2, 4-8, and 10-12 were overcome in the amendment filed 7/23/2026. However, the 103 rejection of claims 20-21 is maintained, and the double patenting rejection of the elected species, and thus claims 1-2, 5-6, 8, and 20-21, is maintained. The full scope of the claims has not yet been searched in accordance with Markush search practice. Claims 1-2, 4-8, 10-12, and 20-21 read on the elected species. Claims 3, 9, 13-19, and 22-23 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to nonelected species and/or group, there being no allowable generic or linking claim.
MAINTAINED OBJECTIONS AND REJECTIONS
Objection to Drawings
New corrected drawings in compliance with 37 CFR 1.121(d) are required in this application because Figures 1-3 are not able to be interpreted as they are in pixelated and illegible. It is unclear what values correspond to what peaks in the drawings. Applicant is advised to employ the services of a competent patent draftsperson outside the Office, as the U.S. Patent and Trademark Office no longer prepares new drawings. The corrected drawings are required in reply to the Office action to avoid abandonment of the application. The requirement for corrected drawings will not be held in abeyance.
Claim Objections
Claims 1 and 20 are objected to for pixelated and illegible images. Appropriate correction is required.
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.
Claims 20-21 are rejected under 35 U.S.C. 103 as being unpatentable over Eurofins Advinus Limited (WO 2021/033172 A1, cited in the IDS of 7/6/2023, herein after “Eurofins”) in view of Sugimoto (US 2012/0264738 A1).
Determining the scope and contents of the prior art
The reference Eurofins teaches the following transformation (page 12, Scheme 7.2):
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Compound 14 of Eurofins maps to a compound of instant Formula D:
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When X1 is Br, X2 is Cl, X4 is Cl, and R is lower alkyl, which is converted to chlorantraniliprole, a compound of instant Formula E:
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When X1 is Br, X2 is Cl, X4 is Cl, and R’ is lower alkyl by methylamine, a compound of R’NH2 when R’ is lower alkyl, in acetonitrile at a temperature of 0°C to 10°C followed by warming to room temperature.
The reference Sugimoto teaches the aminolysis of a highly decorated dispiropyrrolidine compound with methylamine, a compound of R’NH2 where R’ is a lower alkyl group, in dichloromethane, a halogenated hydrocarbon solvent (page 32, bottom right and page 33, para [0361]):
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Because this is the same chemical transformation mechanistically on a different chemical backbone, Sugimoto helps teach step iii).
Ascertaining the differences between the prior art and the claims at issue
The reference Eurofins fails to teach the conversion of a compound of Formula D to a compound of Formula E in a halogenated hydrocarbon solvent.
The reference Sugimoto fails to teach the synthesis of chlorantraniliprole, a compound of Formula E.
Resolving the level of ordinary skill in the pertinent art
The level of ordinary skill in the art is represented by an artisan who has sufficient background in processes of preparation of insecticidal anthranilamides. An artisan possess the technical knowledge necessary to make adjustments to the processes to enhance their effectiveness. Said artisan has also reviewed the problems in the art as regards to use of processes of preparation of insecticidal anthranilamides and understands the solutions that are widely known in the art.
Considering objective evidence present in the application indicating obviousness or nonobviousness
Applying KSR prong (B), it would have been prima facie obvious to one of ordinary skill in the art to substitute the acetonitrile of the reaction of Eurofins with the halogenated hydrocarbon solvent dichloromethane of Sugimoto because the aminolysis reaction with methylamine is known to occur in both solvents. A skilled artisan would be motivated to make the substitution to identify additional methods of making chlorantraniliprole and streamline large scale insecticidal anthranilamide synthesis. Further, one of ordinary skill would reasonably predict that the substitution would result in a successful synthesis in light of the teachings of Eurofins and Sugimoto.
Double Patenting
The nonstatutory double patenting rejection is based on a judicially created doctrine grounded in public policy (a policy reflected in the statute) so as to prevent the unjustified or improper timewise extension of the “right to exclude” granted by a patent and to prevent possible harassment by multiple assignees. A nonstatutory double patenting rejection is appropriate where the conflicting claims are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg, 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); In re Goodman, 11 F.3d 1046, 29 USPQ2d 2010 (Fed. Cir. 1993); In re Longi, 759 F.2d 887, 225 USPQ 645 (Fed. Cir. 1985); In re Van Ornum, 686 F.2d 937, 214 USPQ 761 (CCPA 1982); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); In re Thorington, 418 F.2d 528, 163 USPQ 644 (CCPA 1969).
A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) or 1.321(d) may be used to overcome an actual or provisional rejection based on nonstatutory double patenting provided the reference application or patent either is shown to be commonly owned with the examined application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. See MPEP § 717.02 for applications subject to examination under the first inventor to file provisions of the AIA as explained in MPEP § 2159. See MPEP § 2146 et seq. for applications not subject to examination under the first inventor to file provisions of the AIA . A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b).
The filing of a terminal disclaimer by itself is not a complete reply to a nonstatutory double patenting (NSDP) rejection. A complete reply requires that the terminal disclaimer be accompanied by a reply requesting reconsideration of the prior Office action. Even where the NSDP rejection is provisional the reply must be complete. See MPEP § 804, subsection I.B.1. For a reply to a non-final Office action, see 37 CFR 1.111(a). For a reply to final Office action, see 37 CFR 1.113(c). A request for reconsideration while not provided for in 37 CFR 1.113(c) may be filed after final for consideration. See MPEP §§ 706.07(e) and 714.13.
The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The actual filing date of the application in which the form is filed determines what form (e.g., PTO/SB/25, PTO/SB/26, PTO/AIA /25, or PTO/AIA /26) should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission. For more information about eTerminal Disclaimers, refer to www.uspto.gov/patents/apply/applying-online/eterminal-disclaimer.
Claims 1-2, 5-8, and 20-21 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claim 1-3 and 7-10 of U.S. Patent No. 12,643,874 (herein after the ‘874 Patent). The Examiner notes this rejection was based on claims 21-23 and 27-30 of Application No. 17/798,970 at the time of the Non-Final dated 4/23/2026, but has since been updated to reflect the issuance of the patent.
Although the claims at issue are not identical, they are not patentably distinct from each other because the claims of the ‘874 Patent recite a process for preparing anthranilamide compounds of Formula IX:
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Which when m is 2, one R1 is halogen, the other R1 is a lower alkyl, n is 1, R2 is halogen, p is 1, R3 is halogen, q is 1, and R4 is lower alkyl, overlaps with chlorantraniliprole and instant Formula E:
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When X1 is bromo, X2 is chloro, X4 is chloro, and R’ is lower alkyl. The claims of the ‘874 Patent recite the process with the same intermediates with different formula names. For example, when R2 is halogen, n is 1, R3 is halogen, p is 1, and X is halogen of Formula VI of the ‘874 Patent, it maps to instant Formula B when X1 is bromo, X2 is chloro, and X3 is chloro. The same overlaps occur between Formula VII of the ‘874 Patent and Formula C of the instant claims and Formula VIII of the ‘874 Patent and Formula D of the instant claims.
NEW REJECTIONS AND OBJECTIONS NECESSITATED BY AMENDMENT
Claim Objections
Claim 4 is objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims.
Claim Rejections - 35 USC § 112(b)
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claim 11 is rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
Claim 11 recites wherein the compound of formula A is 3-halo-1-(3-halo-2-pyridinyl)-4,5-dihydro-1H-pyrazole-5-carboxylic acid and the compound of formula B is 3-halo-1-(3-halo-2-pyridinyl)-1H-pyrazole-5-carbonyl halide. Claim 11 depends from claim 10, which recites bromine and chlorine as the only halogens available for the compounds of Formula A and Formula B. Thus, the scope of claim 11 is larger than that of claim 10, and there is insufficient antecedent basis for the limitations of 3-halo-1-(3-halo-2-pyridinyl)-4,5-dihydro-1H-pyrazole-5-carboxylic acid and is 3-halo-1-(3-halo-2-pyridinyl)-1H-pyrazole-5-carbonyl halide in the claim. Appropriate correction is required.
Allowable Subject Matter
Claims 10 and 12 are allowed.
Conclusion
Claims 10 and 12 are allowed. Claims 1-2, 5-8, 11, and 20-21 are rejected. Claims 1, 4, and 20 are also objected to. Claims 3, 9, 13-19, and 22-23 are withdrawn.
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 Kendall Heitmeier whose telephone number is (703)756-1555. The examiner can normally be reached Monday-Friday 8:30AM-5:00PM ET.
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, Clinton Brooks can be reached at 571-270-7682. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/K.N.H./Examiner, Art Unit 1621
/CLINTON A BROOKS/Supervisory Patent Examiner, Art Unit 1621
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