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 18/002,928
Claims 1-16 are currently pending.
Priority
Instant application 18/002,928, filed 12/22/2022, claims priority as follows:
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Receipt of the foreign priority application is acknowledged.
Information Disclosure Statement
All references from the IDS’s submitted on 12/22/2022 and 1/4/2024 have been considered unless marked with a strikethrough.
Objection to the Specification
The disclosure is objected to because it contains an embedded hyperlink and/or other form of browser-executable code. Specifically, the hyperlinks on page 59, line 18 and page 91, line 24 are objected to. Applicant is required to delete the embedded hyperlink and/or other form of browser-executable code; references to websites should be limited to the top-level domain name without any prefix such as http:// or other browser-executable code. See MPEP § 608.01.
Election/Restriction
Applicant’s election of Group I, claims 1-11, drawn to compounds and compositions of formula (I), with traverse, in the reply filed 10/23/2025 is acknowledged. Applicant’s election of (rac)-3-Chloro-5-(methylsulfonyl)-N-{1-[3-(2H-1,2,3-triazol-2-yl)pyrazin-2-yl]ethyl}benzamide, compound I-1:
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without traverse, in the reply filed 10/23/2025, is also acknowledged. The Examiner notes though the image depicts incorrect valency in the central amide, the nitrogen should have a hydrogen to complete valency as per the chemical name.
The traversal is on the grounds that the essential technical feature is the core of Formula (I), and thus all groups have unity of invention. Further, Applicant argues that the compounds of the instant invention are novel and nonobvious over the prior art Syngenta Participations AG (WO 20208/070049 A1, cited in the IDS of 12/22/2022) of the Restriction/Election of Species Requirement of 7/16/2025. Applicant’s arguments have been considered, and have been found persuasive. Thus, the restriction requirement has been withdrawn.
Claim Interpretation
Claim 11 recites, “A composition comprising the compound of claim 1 or a formulation thereof”. However, the instant specification does not define the term, “composition”, and more particularly does not define the difference between a “composition” and “formulation”, as a skilled artisan may interpret those as synonyms. One of ordinary skill in the art would define a composition as a combination of a compound of the instant invention and a diluent, excipient, adjuvant, carrier, etc., which would most likely overlap with the extenders, surface-active substances, auxiliaries, excipients, solvents, and/or additional pharmaceutically active agents recited in claim 10. Thus, the limitation “composition" is currently being interpreted in accordance with the broadest reasonable interpretation of a skilled artisan as a compound of the instant invention and a diluent, excipient, adjuvant, or carrier.
Claim Objections
Claims 12 and 13 recite the term, “and ectoparasite”, but should read “an ectoparasite”. Appropriate correction is required.
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.
Claims 9 and 16 are 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 9 recites the limitations R81 and R82, but does not define them in the claim. Additionally, R81 and R82 are not defined in claim 1, the claim from which claim 9 depends. There is insufficient antecedent basis for this limitation in the claim. Appropriate correction is required.
Claim 16 recites the variable R2 and definitions thereof. However, claim 16 is directed to formulas IX-1, X, XIII, or XXII, which do not recite the variable R2. Thus, the limitation is indefinite and unclear. Appropriate correction is required.
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.
(a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention.
Claims 1-5, 8, and 10-15 are rejected under 35 U.S.C. 102(a)(2) as being anticipated by Syngenta Crop Protection AG (WO 2021/037614, cited in the IDS of 12/22/2022, herein after “Syngenta ‘614”).
The reference Syngenta ‘614 discloses pesticidally active compounds (abstract), and with respect to claims 1-5, 8, and 10-11, specifically discloses compound P1 (page 100, Table):
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Which anticipates a compound of instant formula (I):
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When R1 is H, R2 is phenyl substituted with C1 haloalkyl, R3 is C1 alkyl, R4 is a monocyclic 5-membered heteroaryl containing three nitrogens that is substituted by a C1 alkyl group, R5 is H, and R6 is H. Compound P1 was placed in DMSO, indicating a formulation and composition, and was used in a method of treating Chilo suppressalis (Striped rice stemborer) (page 136, Example B3).
Regarding claims 1-2 and 10-15, Syngenta ‘614 teaches compound P2 (page 100, Table):
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Which anticipates a compound of instant formula (I):
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When R1 is H, R2 is a phenyl substituted with a halogen and a C1 haloalkyl, R3 is C1 alkyl, R4 is a monocyclic 5-membered heteroaryl containing three nitrogens, R5 is H, and R6 is H. Compound P2 was placed in DMSO to generate a formulation and a composition, and was applied to a seed that was then obtained in a method of treating Spodoptera littoralis (Egyptian cotton leaf worm) (page 137, Example B7).
Claim 16 is rejected under 35 U.S.C. 102(a)(1) as being anticipated by ACS (American Chemical Society. Chemical Abstract Service. RN 1247614-35-2, Entered into STN 27 Oct 2010). The instant claim is drawn to intermediate compounds according to formulas IX-1, X, XIII, or XXII.
The reference ACS teaches the following compound:
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Which anticipates a compound of instant formula X:
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When R3 is H, R4 is monocyclic 5-membered heteroaryl containing 3 nitrogens, R5 is H, and R6 is H. Thus, ACS anticipates claim 16.
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, 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 1-3 and 10-15 are rejected under 35 U.S.C. 103 as being unpatentable over Syngenta Crop Protection AG (WO 2021/037614, cited in the IDS of 12/22/2022, herein after “Syngenta ‘614”). This rejection applies to the elected species.
Determining the scope and contents of the prior art
The reference Syngenta ‘614 teaches as disclosed above, and at least those teachings are incorporated herein. Specifically, Syngenta ‘614 teaches compounds of formula I:
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Of which the instant elected species is a compound of when R1 is H, R2a is C1 alkylsulfonyl, R2b is a halogen, A is C-R2c, R2c is H, R3 is C1 alkyl, R4 is
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, where R4b is H and R4c is H, R5a is H, and R5b is H (page 139, claim 1).
In addition to the genus above, Syngenta ‘614 teaches compounds that would direct a skilled artisan to the elected species. Specifically, Syngenta ‘614 teaches compounds such as P33 and P35, both active in pesticide assays (Examples B1, B3, B4, B6, B9, and B10), that differ by a single substituent on the R2 phenyl from the elected species (page 105, Table). The elected species contains a chloro substituent and a methylsulfonyl substituent at the meta positions of the ring, whereas the compound P33 contains a chloro and a C1haloalkoxy at the meta positions, and P35 contains a chloro and a bromo at those same positions. Not only would one of ordinary skill immediately recognize a methylsulfonyl as an additional electron-withdrawing substituent to try on the ring, Syngenta ‘614 also teaches a methylsulfonyl at the meta position of the phenyl ring as variable K17 in preferred embodiments of the invention (page 10).
Further, compounds of Syngenta ‘614 were placed in DMSO to generate formulations and compositions (Examples B1-B10), and are useful for treating insects such as corn root worms, diamond back moths, and green peach aphids. With respect to claims 14 and 15, lettuce seeds were coated with the compounds of Syngenta ‘614 to treat Egyptian cotton leaf worms (page 137, Example B7).
Ascertaining the differences between the prior art and the claims at issue
The reference Syngenta ‘614 fails to teach the elected specie as an anticipatory specie.
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 the development of pesticides. An artisan possess the technical knowledge necessary to make adjustments to the pesticides to enhance their effectiveness. Said artisan has also reviewed the problems in the art as regards to use of said pesticides and understands the solutions that are widely known in the art.
Considering objective evidence present in the application indicating obviousness or nonobviousness
It would have been prima facie obvious to arrive at the limitations of the instant claims because Syngenta ‘614 teaches the genus formula I, which anticipates the elected species, and treatment of pests with compounds of formula I. Additionally, Syngenta ‘614 teaches compounds active in pesticide assays that differ by a single substituent from the elected species, and further directs a skilled artisan to the substituent by highlighting a phenyl ring with a meta-methylsulfonyl as a preferred embodiment. A skilled artisan would be motivated to synthesize the elected species because structurally similar compounds would be expected to have structurally similar properties. According to MPEP § 2144.08:
In fact, similar properties may normally be presumed when compounds are very close in structure. Dillon, 919 F.2d at 693, 696, 16 USPQ2d at 1901, 1904. See also In re Grabiak, 769 F.2d 729, 731, 226 USPQ 870, 871 (Fed. Cir. 1985) (“When chemical compounds have ‘very close’ structural similarities and similar utilities, without more a prima facie case may be made.”). Thus, evidence of similar properties or evidence of any useful properties disclosed in the prior art that would be expected to be shared by the claimed invention weighs in favor of a conclusion that the claimed invention would have been obvious. Dillon, 919 F.2d at 697-98, 16 USPQ2d at 1905; In re Wilder, 563 F.2d 457, 461, 195 USPQ 426, 430 (CCPA 1977); In re Lintner, 458 F.2d 1013, 1016, 173 USPQ 560, 562 (CCPA 1972).
One of ordinary skill in the art would have reasonably predicted that the elected species would result in a compound capable of treating pesticides in view of the teachings of Syngenta ‘614. The Examiner notes this argument can be expanded to encompass multiple compounds of the instant invention.
Claims 6 and 7 are rejected under 35 U.S.C. 103 as being unpatentable over Syngenta Crop Protection AG (WO 2021/037614, cited in the IDS of 12/22/2022, herein after “Syngenta ‘614”).
Determining the scope and contents of the prior art
The reference Syngenta ‘614 teaches as disclosed above, and at least those teachings are incorporated herein. Furthermore, formula I of Syngenta ‘614:
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Allows for R2a to be H, R2b to be H, and A to be N or C-R2c, where R2c can be H, which is also known as phenyl or pyridyl rings. This aryl ring overlaps with instant variable R2, and claim 6 recites that R2 can be phenyl or pyridyl, and claim 7 recites that R2 can be phenyl.
Ascertaining the differences between the prior art and the claims at issue
The reference Syngenta ‘614 fails to teach an anticipatory specie where the aryl ring that maps to instant R2 is an unsubstituted phenyl or pyridyl.
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 the development of pesticides. An artisan possess the technical knowledge necessary to make adjustments to the pesticides to enhance their effectiveness. Said artisan has also reviewed the problems in the art as regards to use of said pesticides and understands the solutions that are widely known in the art.
Considering objective evidence present in the application indicating obviousness or nonobviousness
It would have been prima facie obvious to arrive at the limitations of the instant claims because Syngenta ‘614 teaches the genus formula I, and specifically teaches that the aryl ring that maps to instant R2 can be an unsubstituted phenyl or pyridyl, and treatment of pests with compounds of formula I. A skilled artisan would be motivated to synthesize the compounds with an unsubstituted phenyl or unsubstituted pyridyl because structurally similar compounds have structurally similar properties. According to MPEP § 2144.08:
In fact, similar properties may normally be presumed when compounds are very close in structure. Dillon, 919 F.2d at 693, 696, 16 USPQ2d at 1901, 1904. See also In re Grabiak, 769 F.2d 729, 731, 226 USPQ 870, 871 (Fed. Cir. 1985) (“When chemical compounds have ‘very close’ structural similarities and similar utilities, without more a prima facie case may be made.”). Thus, evidence of similar properties or evidence of any useful properties disclosed in the prior art that would be expected to be shared by the claimed invention weighs in favor of a conclusion that the claimed invention would have been obvious. Dillon, 919 F.2d at 697-98, 16 USPQ2d at 1905; In re Wilder, 563 F.2d 457, 461, 195 USPQ 426, 430 (CCPA 1977); In re Lintner, 458 F.2d 1013, 1016, 173 USPQ 560, 562 (CCPA 1972).
One of ordinary skill in the art would have reasonably predicted that the compounds with an unsubstituted phenyl or unsubstituted pyridyl would result in a compound capable of treating pesticides in view of the teachings of Syngenta ‘614.
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 1-16 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-11 and 15-20 of Application No. 17/766,151 (herein after “’151 Application”). The Examiner acknowledges the application has been allowed; however, no U.S. Patent No. has been issued as of 2/14/2026. Although the claims at issue are not identical, they are not patentably distinct from each other because the claims of the ‘151 Application teach compounds of formula (I):
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Which overlaps with formula I of the instant claims. Further, the claims of the ‘151 Application are drawn to formulations of compounds of formula I, methods of controlling one or more pests with compounds of formula I, and intermediates en route to compounds of formula I. However, formula I of the ‘151 Application differs from the instant claims by the variable R4. The variable R4 of the ‘151 Application can be a monocyclic heterocycle selected from the group consisting of a 5-membered heteroaryl, a 6-membered heteroaryl, and a 3-6 membered heterocycle, each of which containing 1 or 2 heteroatoms selected from the group consisting of N, O, and S. The instant claims require R4 to be a monocyclic 5-membered heteroaryl, containing 3 or 4 heteroatoms selected from the group consisting of N, O, and S.
Though the claims of the ‘151 Application differ by the fact that the 5-membered heteroaryl contains 1 or 2 heteroatoms, whereas the instant claims require 3 or 4 heteroatoms, it would have been prima facie obvious to one of ordinary skill in the art to arrive at a 3 or 4 heteroatom 5-membered heteroaryl from the teachings of the ‘151 Application because according to MPEP § 2144.09, second paragraph, “Compounds which are position isomers or homologs are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties.” In re Wilder, 563 F 2d 457, 195 USPQ426 (CCPA 1997). The 5-membered heteroaryl with 3 or 4 heteroatoms is expected to be preparable by the same method as the 5-membered heteroaryl with 1 or 2 heteroatoms and is expected to generally have the same properties. The expectation is then deemed the motivation for preparing the 5-membered heteroaryl with 3 or 4 heteroatoms.
Issue of Note
Claim 15 recites, “Seed obtained by a method according to claim 14”, which has been evaluated under the subject matter eligibility test for products and processes. Though the claim is directed to a seed, which is a natural phenomenon (product of nature), the claim recites additional elements that amount to significantly more than the judicial exception because the seed is a seed obtained by a method of treating a plant pest with a compound according to claim 1, or a formulation thereof, by contact with a seed or germinating plant. Thus, the subject matter is considered eligible under 35 U.S.C. 101.
Close Prior Art Not Cited Under 35 U.S.C. 102 or 103
Additional close prior art not cited is Syngenta Crop Protection AG (WO 2020/201398, herein after “Syngenta ‘398”) which discloses compounds as insecticides (abstract), and specifically teaches compounds such as P26 (page 93):
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Which solely differs from the elected species by the presence of an additional pyrazine instead of a triazole substituted at the ortho position of the core pyrazine. Compound P26 was found to have at least 80% control against Corn root worm, Striped rice stemborer, Diamond back moth, and Egyptian cotton leaf worm (pages 174-176). However, there is no motivation, teaching, or suggestion, in Syngenta ‘398 alone or in view of the prior art, to substitute the terminal pyrazine for the triazole of the elected species or a 5-membered heteroaryl of the instant claims at the same position.
Conclusion
Claims 1-16 are rejected.
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.
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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