FINAL REJECTION
Receipt is acknowledged of Applicants' Amendments and Remarks, filed Feb. 5, 2020.
Rejections and/or objections not reiterated from previous Office Actions are hereby withdrawn. The rejections and/or objections set forth below are either maintained or newly applied, and constitute the complete set presently applied to the instant claims.
STATUS OF THE CLAIMS
Claim 2 has been canceled.
Claims 1, 7-9, and 12 have been amended and incorporate no new matter.
New claims 21-25 have been added.
Claims 3, 5, 6, and 16-20 stand withdrawn as drawn to nonelected inventions and/or species.
Thus, claims 1, 4, 7-15, and 21-25 now represent all claims currently pending and under consideration.
INFORMATION DISCLOSURE STATEMENT
No new Information Disclosure Statements (IDS) have been submitted.
MAINTAINED REJECTIONS
The following rejection is maintained from the previous Office Action dated Nov. 5, 2025, on the ground that the references cited therein continue to read on the limitations of the amended claims.
Claim Rejections - 35 USC § 103
Claims 1, 4, and 7-15 stand rejected under pre-AIA 35 U.S.C. 103(a) as being unpatentable over Tashiro et al. (WO2020/171077, as evidenced by English equivalent EP 3 928 607 A1) in view of Fischer et al. (WO2018/050825) and Kudo et al. (WO2017/155103). In addition, this rejection is extended to new claims 21-25.
Tashiro et al. disclose compounds of formula (I) in compositions and methods for controlling harmful arthropods (abstract), such as insects, mites, nematodes, and mollusks (paras. [0072]-[0086]).
In particular, Tashiro et al. disclose compounds of formula (II-2O) (paras. [0026], [0028]), having the structural formula,
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wherein A3-A6 are N or CR6c, CR6d, CR6c, or CR6f, respectively, where CR6c, CR6d, and CR6f are, e.g., hydrogen or C1-6 alkyl substituted by, e.g., halo;
A7 is NR6g, CR6hR6i, or O, where R6h and R6i are, e.g., hydrogen;
G1-G4 are N or CR3a-d, where R3a-d are, e.g., hydrogen or C1-6 alkyl substituted by, e.g., halo; and R2 is C1-6 alkyl (para. [0005]; claim 1).
Formula (II-2O) of Tashiro et al. differs from formula (I) as recited by claim 1 in the position of the ring nitrogens in the alkylsulfonyl-substituted bicyclic ring system: the compounds of Tashiro et al. are imidazo-pyridines rather than pyrazolo-pyridines.
However, alkylsulfonyl-substituted pyrazolo-pyridines were known in the art as insecticides, acaricides, miticides, molluscicides, and/or nematicides.
For example, Fischer et al. disclose compounds of formula (XIX) (p. 30),
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wherein Aa-Ad are N or CR10-13, respectively, wherein CR10-13 are hydrogen, C1-6 alkyl, or C1-6 haloalkyl; R1 is, e.g., C1-6 alkyl; and n is 0, 1, or 2 (p. 1, line 21 to p. 2, line 3; p. 3, lines 1-3; p. 5, line 9); and Q is selected from various 5-6 ring systems, such as Q17 or Q18, having the structural formulae,
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which are bonded to the pyrazolo[1,5-a]pyridine ring system at # via a nitrogen.
Further, Fischer et al. exemplify compound (I-11), having the structural formula,
Fischer et al. Compound (I-11)
Claimed Formula (I)
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which reads on formula (I) as recited by claim 1 to the extent that G1 is N; G2 is CH; R1 is ethyl; R2 is CF3; R3 is methyl (which can be modified to haloalkyl); and R4 is hydrogen.
Compound (I-11) differs from claimed formula (I) in that the 5-membered ring attached to the pyrazole is imidazole rather than pyrrolidin-2-one, which is taught by Tashiro.
In addition, Kudo et al. disclose compounds of formula (I) as pest control agents, e.g., pesticides or miticides (abstract). For example, Kudo et al. exemplify compound 1-1-004a (p. 121), having the structural formula,
Kudo et al. Compound (1-1-004a)
Claimed Formula (I)
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which reads on formula (I) as recited by claim 1 to the extent that G1 is N; G2 is CH; R1 is ethyl; R2 is CF3; R3 is hydrogen (which can be modified to haloalkyl); and R4 is CF3.
Compound (1-1-004a) differs from claimed formula (I) in that the 5-membered ring attached to the pyrazole is imidazole rather than pyrrolidin-2-one, which is taught by Tashiro.
The examples of both Fischer et al. and Kudo et al. have an ethylsulfonyl-pyrazolo-[1,5a]pyridine ring, with a substituent (methyl or trifluoromethyl), which fall within the scope of compound (II-2O) of Tashiro et al., wherein G1, G2, G3, and G4 are CH; and R2 is ethyl.
Replacing the imidazo-pyridine moiety in the compounds of formula (II-2O) of Tashiro et al. with the 3-ethylsulfonyl-pyrazolo[1,5-a]pyridin-2-yl moiety exemplified by Fischer et al. and Kudo et al. yields compounds having the structural formula,
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wherein A3 is nitrogen, A4 is CH, A5 is C-CF3, and A6 is CH, as in the compounds exemplified by Fischer et al. and Kudo et al.
Formula (II-2O) of Tashiro et al., as modified by Fischer et al. and Kudo et al., reads on claims 1, 4, 7-13, and 21-25 wherein X is SO2 and R1 is ethyl; one of G1 and G2 is N and one is CH; R2 is trifluoromethyl; and one of R3 and R4 is hydrogen and one is methyl or trifluoromethyl.
Where A3 is nitrogen, A4 is CH, A5 is C-CF3, A6 is CH, R3 is CF3, and R4 is hydrogen, this reads on the elected compound species (compound P5),
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as recited by claims 14 and 24.
The compounds of Tashiro et al. are disclosed in compositions with an inert carrier, surfactant, and/or other auxiliary agent(s) for use in pest control, and for application to soil, roots, or plants for controlling harmful arthropods (paras. [0087]-[0104]). Similarly, the compounds of Fischer et al. are disclosed in pest-control agrochemical formulations with excipients, solvents, carriers, and/or other excipients (p. 45, line 16 to p. 48, line 16; claims 9-10). The compounds of Kudo et al. are exemplified in formulations for use as insecticidal pest control agents (Test Examples 1-17), as recited by claims 15 and 25.
It would have been predictable to one of ordinary skill in the art as of the filing date to modify the compounds of Tashiro et al. as taught by Fischer et al. and Kudo et al. to arrive at the claimed compounds with a reasonable expectation of success, because the close structural similarity of the prior art compounds, and their disclosure for the same use as the claimed compounds, as insecticides or pesticides, create the expectation that combining closely similar moieties would yield compounds exhibiting similar properties, functions, and utilities.
The closer the chemical similarities between the claimed species or subgenus and any exemplary species or subgenus disclosed in the prior art, the greater the expectation that the claimed subject matter will function in an equivalent manner to the genus. See, e.g., In re Dillon, 919 F.2d at 693, 696, 16 USPQ2d at 1901, 1904 (and cases cited therein); and In re Deuel, 51 F.3d 1552, 1558, 34 USPQ2d 1210, 1214 (Fed. Cir. 1995).
As recognized by MPEP § 2144.09, a prima facie case of obviousness may be made when chemical compounds have (1) very close structural similarities and (2) similar utilities. "An obviousness rejection based on similarity in chemical structure and function entails the motivation of one skilled in the art to make a claimed compound, in the expectation that compounds similar in structure will have similar properties." In re Payne, 606 F.2d 303, 313, 203 USPQ 245, 254 (CCPA 1979).
RESPONSE TO ARGUMENTS
Applicant's arguments filed Feb. 5, 2026 have been fully considered but they are not persuasive.
First, Applicant argues that the three-way combination of Tashiro, Fischer, and Kudo, does not render obvious elected compound P5, because the fabricated structure from the three-way combination of Tashiro, Fischer, and Kudo does not contain a CF3 on the pyrazolo:
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(Remarks, pp. 11-13). Applicant argues that the specific compounds of Fischer and Kudo relied upon do not support incorporating the missing CF3, as shown in the table below.
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Thus, Applicant contends that the rejection fails to address the missing CF3 on the pyrazolopyridine, and therefore, fails to establish a prima facie case of obviousness (Remarks, pp. 13-14).
Additionally, regarding Tashiro et al., Applicant argues that simply considering A3-A7 and Z, there are 2x2x2x3x2x2 = 96 distinct possible structures for Q2. From among these 96 different structures, Tashiro favors some of these more than others. For example, Tashiro discloses certain groups Q11-Q60, the majority of which belong to the Q1 formula and are not relevant to the instant claims. Twenty options for Q2 have a nitrogen at A7; and no specific compounds having a carbon atom at the A7 position are disclosed (Remarks, p. 14).
Thus, Applicant argues that, while Tashiro includes a general teaching of a group Q2 that may encompass the corresponding substructure of the instant claims, the more specific teachings lead away from the claimed substructure (Remarks, p. 14).
Applicant argues that it is wholly unclear how a person of ordinary skill in the art arrives at the elected species from the general disclosure of Tashiro, in view of Fischer and Kudo, based on the apparently 19 compounds tested in Tashiro with about 14 meeting threshold activity in the reported testing. Neither Fischer nor Kudo remedy this defect, as neither teaches the corresponding substructure of the instant claims (Remarks, pp. 14-15).
However, Applicant's reading of the cited references is impermissibly narrow. As recognized by MPEP § 2123, a reference may be relied upon for all that it would have reasonably suggested to one having ordinary skill the art, including non-preferred embodiments. Merck & Co. v. Biocraft Laboratories, 874 F.2d 804, 10 USPQ2d 1843 (Fed. Cir. 1989). Disclosed examples and preferred embodiments do not constitute a teaching away from a broader disclosure or non-preferred embodiments. In re Susi, 440 F.2d 442, 169 USPQ 423 (CCPA 1971).
The rejection is premised upon the subgenus of formula (II-2O) of Tashiro et al.,
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wherein A7 is defined as NR6g, CR6hR6i, or O, where R6h and R6i are, e.g., hydrogen (see claim 1). Thus, while it is acknowledged that Tashiro et al. do not exemplify compounds wherein A7 is CH2, Tashiro et al. expressly contemplate and claim compounds wherein A7 is CH2, and A3-A6 are N or CH, such that a skilled artisan could readily envisage the left-hand moiety of formula (II-2O) as pyrrolidin-2-one fused to, e.g., benzene or pyridine, as in the claimed compounds.
Moreover, the cited references do, in fact, teach a trifluoromethyl group at position 5 of the pyrazolo-pyridine ring, although it is not depicted in the rejection set forth above.
For reference, a pyrazolo-pyridine ring with IUPAC ring numbering is shown below:
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As noted in the rejection set forth above, Formula (II-2O) of Tashiro et al. encompasses compounds in which G1-G4 are N or CR3a-d, respectively, where R3a-d are, e.g., hydrogen or C1-6 alkyl substituted by, e.g., halo; (i.e., haloalkyl) (para. [0005]). This includes G2, which is selected from N or CR3b, wherein R3b is, e.g., C1-6-alkyl, which may be substituted by Group B (para. [0007]), which includes halogen (i.e., haloalkyl) (p. 5, lines 37-43).
Further, Tashiro et al. exemplify compound 55, having close structural similarity including CF3 in the same positions as the elected compound (Example 55, p. 69):
Tashiro et al. Example 55
Elected compound species (P5)
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Thus, Tashiro et al. expressly contemplate and exemplify CF3 at the 5-position of the analogous imidazo-pyridine ring.
Similarly, formula (XIX) of Fischer et al. encompasses compounds in which Aa-Ad are N or CR10-13, respectively, wherein CR10-13 are hydrogen, C1-6 alkyl, or C1-6 haloalkyl (claim 1). This includes Ac, which is selected from nitrogen or CR12, wherein R12 includes, e.g., C1-4-haloalkyl (claim 4):
Fischer et al. Formula (XIX)
Elected compound species (P5)
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Thus, Fischer et al. expressly contemplate CF3 at the 5-position of the pyrazolo-pyridine ring.
Similarly, Kudo et al. exemplify compounds of the formula of Example 43, wherein Y2 is trifluoromethyl (e.g., compounds 1-1-012a and 1-1-012b; para. [0183], p. 121):
Kudo et al. Example 43
Elected compound species (P5)
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Thus, Kudo et al. expressly contemplate CF3 at the 5-position of the pyrazolo-pyridine ring.
Therefore, all three cited references expressly disclose compounds wherein position 5 of the pyrazolo-pyridine (or analogous) ring is substituted by CF3.
Furthermore, as discussed in the rejection set forth above, the compounds of all three cited references are disclosed as pesticides, insecticides, and/or miticides, which is also the disclosed utility of the claimed compounds. The rationale to combine Tashiro et al., Fischer et al., and Kudo et al. is premised upon this shared utility: one of ordinary skill in the art would have been motivated to combine the cited references to arrive at the elected compound species (P5) with a reasonable expectation of success, because the compounds of the cited references share close structural similarity and are disclosed to have the same properties and uses.
As recognized by MPEP § 2144.09, if the claimed invention and the structurally similar prior art compounds share any useful property, that will generally be sufficient to motivate an artisan of ordinary skill to make the claimed species.
A prima facie case of obviousness based on structural similarity is rebuttable by proof that the claimed compounds possess unexpectedly advantageous or superior properties. In re Papesch, 315 F.2d 381, 137 USPQ 43 (CCPA 1963).
Finally, it is noted that the obviousness-type double patenting rejection is withdrawn because co-pending application 18/043,707 was abandoned on Mar. 5, 2026.
CONCLUSION
No claims are allowed.
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.
CORRESPONDENCE
Any inquiry concerning this communication or earlier communications from the examiner should be directed to SARA E. TOWNSLEY whose telephone number is 571-270-7672. The examiner can normally be reached on Mon-Fri from 10:00 am to 6:00 pm (EST). If attempts to reach the examiner by telephone are unsuccessful, the examiner's supervisor, Jeff S. Lundgren, can be reached at 571-272-5541. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/SARA ELIZABETH TOWNSLEY/Examiner, Art Unit 1629
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