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 the Claims
Claims 19-32 are pending. Claims 27-30 are withdrawn. Claims 19-26 and 31-32 are rejected.
Response to Remarks/Arguments
Applicant remarks filed on 8/21/2025 have been fully considered and are addressed below:
Election/Restriction
Applicant’s election of Group I (claims 19-26, 31 and 32) without traverse in the reply filed on 8/21/2025 is acknowledged. Claims 27-30 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention, there being no allowable generic or linking claim.
Prior Art Rejections
Applicant’s remarks regarding the anticipation rejection of claim 32 and the obviousness rejection of claims 19-26 and 31-32 over Narine et al. WO 2014/167084 A1 are persuasive. Applicant noted that the claimed compound is structurally distinct from compound C-38 taught by Narine due to different double bond positionings. Remarks 5.
Double Patenting Rejections
Applicant’s remarks pertaining to the double patenting rejection of claims 19-26 and 31-32 over US 11,124,528 in view of Narine, US 11,034,703 in view of Narine, US 9,730,451 in view of Narine, and US 12,144,349 in view of Narine are persuasive for the same reasons discussed above regarding Narine’s compound having a different double bond positioning. Remarks 5.
Applicant’s remarks regarding the provisional double patenting rejection of claims 19-26 and 31-32 over US 18/272,884, 18/272,820 and 17/274,909 are not persuasive. However, the provisional rejections have been reconsidered and are withdrawn (and reasserted under new grounds) with respect to claims 24-26 and 31. The provisional rejections are maintained for claims 19-23 and 32.
Claim Rejections - 35 USC § 102
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.
Claim 32 is rejected under 35 U.S.C. 102(a)(1)/102(a)(2) as being anticipated by Narine et al. WO 2014/167084A1.
Narine teaches compound no. A-1 of formula (III-12),
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, wherein R1 is methyl and ZR2 is Ph. See Table 12 (p. 27), referring to Table A (p. 38). Compound A-1 of Table 12 is inherently a 1:1 mixture that comprises the claimed I-R-1 compound,
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. Since claim 32 reads on any mixture comprising the claimed compound, Narine anticipates the claim.
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 19-26 and 31-32 are rejected under 35 U.S.C. 103 as being unpatentable over Narine et al. WO 2014/167084A1.
Narine teaches compounds of formula (I),
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, are useful for “combating animal pests” and “protecting crops [] from attack or infestation by invertebrate pests.” See, e.g., claims 10 and 11. Narine teaches compound no. A-1 of formula (III-12),
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, wherein R1 is methyl and ZR2 is Ph, as an example of a compound of formula (I). See Table 12 (p. 27), referring to Table A (p. 38).
Compound A-1 of Table 12 is inherently a 1:1 mixture that comprises the claimed I-R-1 compound,
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.
Narine does not separate the enantiomers of compound A-1 (of Table 12); however, Narine discloses “both single pure enantiomers or pure diastereomers of the compounds of formula (I) and their mixtures and the use according to the invention of the pure enantiomers or pure diastereomers of the compound of formula (I) or its mixtures.” Narine 7:1-4.
Narine successfully separated racemic compounds by HPLC, such as enantiomers C-25
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and C-28
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, enantiomers C-18
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and C-29
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, and enantiomers C-39
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and C-42
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. See pages 84-92.
A PHOSITA would have been motivated to separate compound A-1 of Table 12 into its individual enantiomers because:
(1) Narine teaches how to separate structurally similar racemates,
(2) Narine teaches excellent insecticidal activity for structurally similar compounds, such as racemic C-38,
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, which is a double bond isomer of compound A-1 of Table 12, and
(3) Narine teaches that pure enantiomers of formula (I) can be obtained and used for the same applications as their racemates.
Therefore, since Narine teaches the use of pure enantiomers of formula (I) for combating animal pests and protecting crops, a PHOSITA would have been motivated to use compounds of formula (I), such as compound A-1 of Table 12, in racemic form and in enantiopure form, for combating animal pests and protecting crops. The PHOSITA would have had a reasonable expectation that compound A-1 of Table 12 in racemic form and in enantiopure form would have been capable of combating animal pests and protecting crops because Narine teaches that structurally similar compounds had insecticidal activity and structurally similar compounds are expected to have similar properties. (See, e.g., racemic C-38
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, enantiomer C-28,
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, and enantiomer C-42,
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which “showed over 75% mortality in comparison with untreated controls” against various pests. Narine 92:24 to 94:37.)
Claims 19-23 and 32 read on the pure (R)-enantiomer of compound no. A-1 of formula (III-12),
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, wherein R1 is methyl and ZR2 is Ph (wherein the (S)-enantiomer is not present).
Claims 24-25 encompass a mixture comprising the pure (R)-enantiomer of A-1 Table 12 in combination with another pesticidal compound. This mixture is obvious over Narine’s disclosure that mixtures of the pesticidal compounds of formula (I) with additional pesticides “can be used and with which potential synergistic effects might be produced” (p. 53:24-30). Furthermore, the component ratio “1000:1 to 1:1000” recited by claim 25 would have been obvious, because a PHOSITA would have been motivated to optimize the ratio of the two pesticidal compounds as a matter of routine experimentation in search of the most effective pesticidal combination. Additionally, Narine suggests a “weight ratio of 1:100 to 100:1, preferably 1:10 to 10:1” of the active compound compared to the additional agent, which includes an added pesticide.
“Various types of oils, wetters, adjuvants, fertilizer, or micronutrients, and other pesticides (e.g. herbicides, insecticides, fungicides, growth regulators, safeners) may be added to the active substances or the compositions comprising them as premix or, if appropriate not until immediately prior to use (tank mix). These agents can be admixed with the compositions according to the invention in a weight ratio of 1 :100 to 100:1, preferably 1:10 to 10:1.” Narine 52:39-53:2.
Claim 26 requires a liquid or solid carrier, which is rendered obvious by Narine’s composition examples that include, e.g., water, solvent, emulsifiers, dispersants, wetting agents, or thickeners. See, e.g., p. 48:7-14 and 50:9 to 52:10. See also Narine’s claims 9-10:
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Regarding claim 31, drawn to a seed comprising 0.1 g to 10 kg per 100 kg of seeds of the enantiomer of claim 19, Narine teaches an identical range:
“Seed comprising a compound of formula (I) and/or stereoisomers or agriculturally or veterinary acceptable salts or tautomers or N-oxides thereof as defined in any one of the claims 1 to 8 in an amount of from 0.1 g to 10 kg per 100 kg of seed.” (claim 14).
Given Narine’s disclosure of the same amount of a compound of formula (I), and given that compound no. A-1 of formula (III-12) is expected to be pesticidally active (due to its structural similarity to other highly active pesticides) a PHOSITA would have been motivated to prepare a seed comprising an enantiomer of compound no. A-1 of formula (III-12) in the amount(s) claimed.
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 19-26 and 31-32 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 3 and 19 of U.S. Patent No. 11,124,528 B2 in view of Narine et al. WO 2014/167084A1.
Although the claims at issue are not identical, they are not patentably distinct from each other because ‘528, claims 3 and 19, teach a compound of formula (X),
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, in the S- or R-configuration, which encompasses a tautomer of the claimed enantiomers.
Narine teaches compounds of formula (I),
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, are useful for “combating animal pests” and “protecting crops [] from attack or infestation by invertebrate pests.” See, e.g., claims 10 and 11. As an example of formula (I), Narine teaches compound no. A-1 of formula (III-12),
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, wherein R1 is methyl and ZR2 is Ph. Table 12 (p. 27), referring to Table A (p. 38). Narine suggests separating and isolating the enantiomers of formula (I), including those of A1 of formula III-12, as discussed above in the obviousness rejection over Narine, which discussion is incorporated by reference.
In view of Narine, a PHOSITA would have found the (S)-enantiomer
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of instant claims 19-23 and 32 to be an obvious species of the genus claimed by ‘528, since Narine teaches the claimed compound. The ‘528 claims do not teach the limitations of instant claims 24-26 and 31; however, Narine renders obvious the instant claims (as discussed in the obviousness rejection, which discussion was incorporated above).
Claims 19-26 and 31-32 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-14 of U.S. Patent No. 11,034,703 B2 in view of Narine et al. WO 2014/167084A1.
Although the claims at issue are not identical, they are not patentably distinct from each other because claims 1-14 of ‘703 disclose a process of making compounds of formula (X),
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in the S- or R-configuration, which encompasses a tautomer of the claimed enantiomers.
Narine teaches compounds of formula (I),
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, are useful for “combating animal pests” and “protecting crops [] from attack or infestation by invertebrate pests.” See, e.g., claims 10 and 11. As an example of formula (I), Narine teaches compound no. A-1 of formula (III-12),
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, wherein R1 is methyl and ZR2 is Ph. Table 12 (p. 27), referring to Table A (p. 38). Narine suggests separating and isolating the enantiomers of formula (I), including those of A1 of formula III-12, as discussed above in the obviousness rejection over Narine, which discussion is incorporated by reference.
In view of Narine, a PHOSITA would have found the (S)-enantiomer
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of instant claims 19-23 and 32 to be an obvious species of the genus claimed by ‘703, since Narine teaches the claimed compound. The ‘703 claims do not teach the limitations of instant claims 24-26 and 31; however, Narine renders obvious the instant claims (as discussed in the obviousness rejection, which discussion was incorporated above).
Claims 19-26 and 31-32 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-23 of U.S. Patent No. 9,730,451 in view of Narine et al. WO 2014/167084A1.
Although the claims at issue are not identical, they are not patentably distinct from each other because the patented claims disclose a compound of formula (I),
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, tautomers, stereoisomers thereof, and a composition thereof comprising at least one inert liquid/solid carrier. Additionally, the claims teach a seed treated with the compound in an amount of from 0.1 g to 10 kg per 100 kg of seed. See, e.g., claims 1-5 and 9-11. The claims do not explicitly teach the compound or a mixture of the compound with another pesticide compound, nor do the claims teach the claimed (R)-enantiomer as an isolated compound or as an enriched mixture.
Narine teaches compounds of formula (I),
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, are useful for “combating animal pests” and “protecting crops [] from attack or infestation by invertebrate pests.” See, e.g., claims 10 and 11. As an example of formula (I), Narine teaches compound no. A-1 of formula (III-12),
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, wherein R1 is methyl and ZR2 is Ph. Table 12 (p. 27), referring to Table A (p. 38). Narine suggests separating and isolating the enantiomers of formula (I), including those of A1 of formula III-12, as discussed above in the obviousness rejection over Narine, which discussion is incorporated by reference.
The enantiomers of A1 (III-12) are identical to the claimed enantiomers. Therefore, a PHOSITA would have found the (S)-enantiomer of instant claims 19-23 and 32, and the composition and seed thereof (claims 26 and 31) to be an obvious species of the genus claimed by ‘451. The ‘451 claims do not teach the limitations of instant claims 24-25; however, Narine renders obvious the instant claims (as discussed in the obviousness rejection, which discussion was incorporated above).
Claims 19-26 and 31-32 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-16 of U.S. Patent No. 12,144,349.
Although the claims at issue are not identical, they are not patentably distinct from each other because the patented claims disclose a mixture comprising compound I-R-1,
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, preferably at least 90% ee per claim 4, with another pesticide in a ratio of 10000:1 to 1:10000, preferably 20:1 to 1:20, according to claim 7. Claim 8 discloses a composition thereof comprising an inert liquid/solid carrier. The compound I-R-1 is identical to instant I-R-1. Therefore, this patented mixture anticipates instant claims 19, 24-26 and 32.
Instant claims 20-23, drawn to higher %ee limitations, would have been obvious since the %ee ranges of ‘349 overlap with the instant ranges, because a PHOSITA would have been motivated to increase the enantiopurity of the composition to optimize its properties.
Regarding the seed of instant claim 31, patented claim 15 teaches a seed comprising compound A of formula (I), which is an obvious variant of compound I-R-1. Since compound A and compound I-R-1 are obvious variants, and claim 15 discloses the claimed amounts, a PHOSITA would have found the instantly claimed seed obvious.
Claims 19-23 and 32 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claim 22 of copending Application No. 18/272,884 (reference application).
Although the claims at issue are not identical, they are not patentably distinct from each other because claim 22 of ‘884 discloses the compound
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, which is a tautomer of the instant compound I-R-1 (labelled as I-R) with at least a 90% ee. This anticipates instant claims 19 and 32. Instant claims 20-23, drawn to higher %ee limitations, would have been obvious since the %ee ranges of ‘884 overlap with the instant ranges, because a PHOSITA would have been motivated to increase the enantiopurity of the composition to optimize its properties.
Claims 24-26 and 31 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claim 22 of copending Application No. 18/272,884 (reference application), as applied above to claims 19-23 and 32, in view of Narine et al. WO 2014/167084A1.
Narine suggests isolating the enantiomers of A1 (III-12), one of which is identical to instant I-R-1 (i.e., 100% ee), and teaches mixtures, compositions and seeds thereof, which render obvious instant claims 24-26 and 31 as discussed above in the obvious rejection (which discussion is incorporated here by reference), since a PHOSITA would have been motivated to make the claimed invention starting from the reference application.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Claims 19-23 and 32 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-16 of copending Application No. 18/272,820 (reference application).
Although the claims at issue are not identical, they are not patentably distinct from each other because ‘820 discloses an enantioenriched tautomer of the instant compound I-R-1 (labelled as I-R) with at least a 55% ee. See, e.g., claim 15. This anticipates instant claim 32. Instant claims 19-23, drawn to higher %ee limitations, would have been obvious since the %ee range of ‘820 overlaps with the instant ranges, because a PHOSITA would have been motivated to increase the enantiopurity of the composition to optimize its properties.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Claims 24-26 and 31 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claim 22 of copending Application No. 18/272,820 (reference application), as applied above to claims 19-23 and 32, in view of Narine et al. WO 2014/167084A1.
Narine suggests isolating the enantiomers of A1 (III-12), one of which is identical to instant I-R-1 (i.e., 100% ee), and teaches mixtures, compositions and seeds thereof, which render obvious instant claims 24-26 and 31 as discussed above in the obvious rejection (which discussion is incorporated here by reference), since a PHOSITA would have been motivated to make the claimed invention starting from the reference application.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Claims 19-23 and 32 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1, 4-10 and 13-15 of copending Application No. 17/274,909 (reference application).
Although the claims at issue are not identical, they are not patentably distinct from each other because ‘909 discloses an enantioenriched compound identical to instant I-R-1 with at least a 98% ee according to claim 15. This anticipates instant claims 19-23 and 32.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Claims 24-26 and 31 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1, 4-10 and 13-15 of copending Application No. 17/274,909 (reference application), as applied to claims 19-23 and 32 above, in view of Narine et al. WO 2014/167084A1.
Narine suggests isolating the enantiomers of A1 (III-12), one of which is identical to instant I-R-1 (i.e., 100% ee), and teaches mixtures, compositions and seeds thereof, which render obvious instant claims 24-26 and 31 as discussed above in the obvious rejection (which discussion is incorporated here by reference), since a PHOSITA would have been motivated to make the claimed invention starting from the reference application.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Contact Information
Any inquiry concerning this communication or earlier communications from the examiner should be directed to AMANDA L AGUIRRE whose telephone number is (571)272-5592. The examiner can normally be reached 10 am-6 pm EDT.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, JOSEPH K McKANE can be reached on 571-272-0699. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/AMANDA L. AGUIRRE/ Primary Examiner, Art Unit 1626
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