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 .
Current Status
This action is responsive to the amended claims of 07/14/2026. Claims 3-5, 7, 9, 11, 13, 15, 17, 19-20, 22, 26, 28, 30, 32, and 34-37 are pending. Claims 1-2 are canceled. Claims 3-5, 7, 9, 11, 13, 15, 17, 19-20, 22, 26, 28, 30, 32, and 34-37 have been examined on the merits.
Priority
The effective filing date is 08/03/2021.
Response to Arguments
Examiner acknowledges receipt of and has reviewed the amended claims and remarks of 07/14/2026; no new matter is found.
The objection to claims 4-5, 7, 9, 11, 13, 15, 17, 19-20, 22, 26, 28, 30, and 32 is withdrawn; Applicant has amended as suggested by Examiner.
The 112(a)-enablement rejection over claims 1-3 and 34-35 is maintained over claims 3 and 34-35. Claims 1-2 have been canceled. Claim 3 is now drawn to a crystalline form of the instant compound wherein the crystalline form is anhydrous or solvent-free. Claims 34-35 now depend from claim 3.
Claim 3, under the broadest reasonable interpretation (BRI), is drawn to any crystalline form (salt, co-crystal, polymorph, etc.) of the instant compound that is anhydrous or solvent-free. The specification and prior art do not provide enough guidance to enable formation of such breadth of polymorph forms of the instant compound. The previously applied rejection is modified below to account for the amendments to the claims.
Note, Applicant has not provided any arguments against the rejection’s merits.
The 112(b) rejection of claim 3 is withdrawn. The claim is now recast an independent.
The 112(b) rejection of claim 26 and 28 is withdrawn. The claims are now dependent from claim 22.
The 112(d) rejection of claim 3 is withdrawn for the same reason in ¶7.
The 112(d) rejection of claims 5, 7, 9, 11, 13, 15, 17, 20, 22, 26, 28, 30, and 32 is maintained. Applicant has amended parent claims 4 and 19 to strike “Form A” and “Form B,” respectively. However, claims 4 and 19 are still drawn to polymorphs defined by XRPD peaks/physicochemical properties inherent to Forms A and B. Since the dependent claims only add further XRPD peaks, the polymorph claimed in the parent claims is not truly further limited. A polymorph is a very specific form of the claimed compound, thus, the act of defining the polymorph by even 1 XRPD peak is the same as calling the polymorph by “Form A” or “Form B”. The crux of the issue is that a polymorph defined by physicochemical data cannot be further limited by additional physicochemical data. Thus, the rejection is maintained with modification to account for the amendments.
The 112(d) rejection of claims 26 and 28 is withdrawn for the same reason in ¶8.
The 102(a)(1) and 102(a)(2) rejections of claims 1-2 and 34-35 over DAVIES (WO 2021/113419; provided 04/17/2026) are withdrawn. Claims 1-2 have been canceled and claims 34-35 now depend from claim 3. DAVIES does not teach the crystalline forms of the pending claims (see prior action Pg. 14 ¶25).
Response to Amendment – Necessitated by Amendment
Claim Objections
Claims 5, 7, 9, 11, 13, 15, 17, 20, 22, 26, 28, 30, 32, and 36-37 are objected to because of the following informalities. Appropriate correction is required.
Claims 5, 7, 9, 11, 13, 15, 17, 20, 22, 26, 28, 30, and 32 each recite “the crystalline polymorph form” of either independent claim 4 or 19. The independent claims 4 and 19 use the term “crystalline polymorph” but do not use the word “form.” While it is clear that “crystalline polymorph form” is equivalent to the “crystalline polymorph” of the independent claims, it is preferred if the language used is consistent between independent and dependent claims.
Claims 36-37 recite “the crystalline form” of claim 4. Claim 4 recites “crystalline polymorph”. Similar to the above objection, while it is clear the crystalline polymorph of claim 4 is “the crystalline form” recited in claims 36-37, it is preferred if the language used between independent and dependent claims is consistent.
To overcome: please align the claim language used so that the phrase used to refer to the crystalline polymorph is consistent between independent and dependent claims.
Claim Rejections - 35 USC § 112
The following is a quotation of the first paragraph of 35 U.S.C. 112(a):
(a) IN GENERAL.—The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor or joint inventor of carrying out the invention.
The following is a quotation of the first paragraph of pre-AIA 35 U.S.C. 112:
The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor of carrying out his invention.
Claims 3 and 34-35 are rejected under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, because the specification, while being enabling for polymorph Form A and Form B, does not reasonably provide enablement for any and all polymorph forms of the claimed compound N-[4-chloro-2-(pyridin-3-yl)-1,3-thiazol-5-yl]-N-ethyl-3-(methylsulfonyl)propanamide. The specification does not enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to practice the invention commensurate in scope with these claims. This is a scope of enablement rejection.
The Wands Factors used in a scope of enablement rejection include (per MPEP 2164.01(a)):
The breadth of the claims:
The claims 3 and 34-35 are drawn to anhydrous/solvent-free crystalline forms of the compound N-[4-chloro-2-(pyridin-3-yl)-1,3-thiazol-5-yl]-N-ethyl-3-(methylsulfonyl)propenamide, a composition thereof, and a method of use thereof. The “crystalline form” is understood to be drawn to any and all crystal forms (inclusive of salts, amorphous, co-crystals, polymorphs, etc.) of the compound as long as they are anhydrous or solvent-free. The claims are narrow in the recited compound; however, they are broad concerning the crystalline forms thereof, specifically any and all anhydrous/solvent-free polymorph forms.
The nature of the invention:
The invention belongs to agrochemical technology, more specifically, crystalline forms of N-[4-chloro-2-(pyridin-3-yl)-1,3-thiazol-5-yl]-N-ethyl-3-(methylsulfonyl)propanamide including generic, anhydrous/solvent-free polymorphs (claim 3), a composition thereof (claim 34), and a process of use as a pesticide (claim 35).
The state of the prior art & predictability of the art:
Examiner cites LAIRD (Laird, T., Organic Process Research & Development, 2010, 14, 1; provided by Examiner 04/17/2026), BUCAR (Bucar, D.K. et al., Angew. Chem. Int. Ed., 2015, 54, 6972-6993; provided by Examiner 04/17/2026), DAVIES (WO 2021/113419; provided by Examiner 04/17/2026) as representative of the state of the prior art and predictability thereof.
LAIRD teaches: “Prediction of crystal structure from a given chemical substance, and hence its polymorphism, is a desired goal which has not been routinely achieved, despite one or two successes with specific molecules. Periodically, blind tests are organized where scientists are challenged to predict crystal structures of specific molecules, and the results are compared to the actual experimental results. Such a blind test in 2001 for the molecule shown below ended in failure, with none of the participants being able to predict the structure correctly.” (¶2).
BUCAR teaches thousands of experimental attempts may be needed to search for stable crystal forms of compounds, with new crystal forms possibly emerging unexpectedly even after carefully designed and executed experiments are completed (Pg. 9673 Left Col. ¶2). “Unfortunately, our current understanding of the mechanisms and processes involved in nucleation and growth of crystals is still insufficient for precise control over the formation or disappearance of a polymorph (or any other crystal form)” (Pg. 6973 Left Col. ¶3). BUCAR further teaches known polymorphs may disappear and some crystal forms are elusive; methods that provide control over crystal nucleation and growth are still an art rather than routine procedure (Pg. 6973 Right Col. ¶1). Moreover, “the mere existence of polymorphs and polymorphic transformations is virtually impossible to predict” (Pg. 6987 Right Col. ¶5) and “there is no standard strategy or foolproof recipe for the search for crystal forms” (Pg. 6988 Left Col. ¶3).
Thus, LAIRD and BUCAR disclose a lack of predictability in the art of crystal and polymorph formation. These two references establish the need for knowledge of controlled conditions and a burdensome level of experimentation to achieve creation of any one defined polymorphic form of a compound. The lack of a “foolproof” or “standard” method for crystal formation underlines the need for experimental examples (either in the art or the instant disclosure) to enable the artisan to practice the full scope of the instant invention (i.e., any anhydrous/solvent-free polymorphs).
DAVIES teaches the generic class of polymorphs of the instant compound N-[4-chloro-2-(pyridin-3-yl)-1,3-thiazol-5-yl]-N-ethyl-3-(methylsulfonyl)propanamide (Pg. 63-64 claims 1-2). However, DAVIES does not provide any guidance in the disclosure as to how such polymorphs are made. DAVIES does not provide conditions under which crystalline polymorph forms are created and thus cannot provide enablement for creation of any anhydrous/solvent-free polymorphs of the instant compound.
Due to the lack of predictability in the art regarding formation of polymorphs, the prior art cannot be relied upon to supplement the enablement of any and all anhydrous/solvent-free polymorphs of the instant compound.
The level of one of ordinary skill:
The relative skill of those in the art is high, generally that of a Ph.D. The artisan using Applicant's invention would generally have several years of experience. This factor is outweighed, however, by the unpredictable nature of the art. It is well established in the relevant art (above) that polymorph formation is an art, not a predictable and routine practice.
The level of one of ordinary skill includes the knowledge/skill to engage in a reasonable amount of experimentation to make and use the polymorph Forms A and B based on the synthetic methods disclosed in the Specification at Pg. 52-60. However, the skill of the artisan, especially in view of the relevant prior art, does not overcome the undue burdensome level of experimentation required to provide enablement for formation and use of any and all polymorphic forms of the instant compound.
The amount of direction provided by the inventor and the existence of working examples:
Inventors have provided direction for synthesis and formation of the claimed Forms A and B. The Specification discloses synthesis of the claimed compound (Pg. 52+) wherein the final step culminates in isolation of the compound as a crystalline solid (Pg. 54 ¶206). The Specification further provides a method for recrystallization of Form A utilizing the crystalline solid of Pg. 54 ¶206 as a seed under defined conditions (Pg. 59 ¶224-228 & Pg. 60 ¶229-231). Further, using the same seed crystal under different defined conditions, the Specification provides details for formation of the Form B (Pg. 60 ¶232-237). The Specification also provides variable crystallization parameters for both Forms A & B (Pg. 60-61 Table 4) and characterization data of each of the Forms A (Pg. 37 Table 1) and B (Pg. 40 Table 3). The Forms A and B are anhydrous/solvent-free (Pg. 34-35 ¶116-122).
For use as pesticides, the Forms A and B were tested for their pesticidal activity (Pg. 65-66 Table 5-7 & Pg. 68-69 Table 8-10). The polymorph forms were found to have pesticidal activity similar to or better than the oil-form of the instant compound.
Thus, Applicants have guidance/enablement in their Specification for formation and use of polymorphic forms of the instant compound Form A and Form B. However, this guidance does not support formation of all anhydrous/solvent-free polymorph forms, especially in view of the relevant prior art.
The quantity of experimentation needed to make or use the invention:
Applicants’ agrochemical invention comprising a crystalline form of the compound N-[4-chloro-2-(pyridin-3-yl)-1,3-thiazol-5-yl]-N-ethyl-3-(methylsulfonyl)propanamide requires a high level/quantity of experimentation to formulate the invention as any and all possible anhydrous/solvent-free polymorphic forms, aside from disclosed Forms A and B. While Applicants have provided guidance in their Specification for making and using polymorph Forms A and B, they have not provided enough guidance for the formation of any polymorphic form of the instant compound per the BRI of instant claims 3 and 34-35.
Therefore, claims 3 and 34-35 are rejected under 35 USC 112(a) for lacking scope of enablement for the full genus of polymorphs of the instant compound. Claims 4 and 19 and their dependent claims are not rejected here since they are drawn to forms defined by XRPD peaks of Forms A and B which are enabled by the specification.
To render moot this scope of enablement rejection: Applicants could cancel claim 3 and import the limitations of “anhydrous” and “solvent-free” into independent claims 4 and 19. This amendment is supported by the Forms A and B disclosed in the specification (see Pg. 34-35 ¶116-122). Further, if Applicant cancels claim 3, please adjust the dependency of claims 34-35.
Claim Rejections - 35 USC § 112(d)
The following is a quotation of 35 U.S.C. 112(d):
(d) REFERENCE IN DEPENDENT FORMS.—Subject to subsection (e), a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
The following is a quotation of pre-AIA 35 U.S.C. 112, fourth paragraph:
Subject to the following paragraph [i.e., the fifth paragraph of pre-AIA 35 U.S.C. 112], a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
Claims 5, 7, 9, 11, 13, 15, 17, 20, 22, 26, 28, 30, and 32 are rejected under 35 U.S.C. 112(d) or pre-AIA 35 U.S.C. 112, 4th paragraph, as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends. As drafted, independent claims 4 and 19 recite polymorph forms defined by XRPD/physicochemical data. These polymorphs inherently contain all the elements found in the dependent claims 5, 7, 9, 11, 13, 15, 17, 20, 22, 26, 28, 30, and 32, such as, XRPD, DSC, and spectroscopic data. If claims 4 and 19 did not contain the inherent limitations of claims 5, 7, 9, 11, 13, 15, 17, 20, 22, 26, 28, 30, and 32, the claims 4 and 19 would technically not be reciting polymorph forms comprising the XRPD peaks recited in claims 4 and 19, respectively. Thus, claims 5, 7, 9, 11, 13, 15, 17, 20, 22, 26, 28, 30, and 32 do not truly further limit what is already (inherently) disclosed within claims 4 and 19. Note, the dependent claims also depend from each other (i.e., claim 7 depends from claim 5, etc.). The same logic applies to each dependent claim.
Applicant may cancel the claim(s), amend the claim(s) to place the claim(s) in proper dependent form, rewrite the claim(s) in independent form, or present a sufficient showing that the dependent claim(s) complies with the statutory requirements.
Conclusion
Claims 3, 5, 7, 9, 11, 13, 15, 17, 20, 22, 26, 28, 30, 32, and 34-35 are rejected
Claims 36-37 are objected to.
Claims 4 and 19 are allowable.
Note: the close art is discussed on Pg. 14 ¶25 of the action mailed 04/17/2026.
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.
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/S.E.B./Examiner, Art Unit 1625
/JOHN S KENYON/Primary Patent Examiner, Art Unit 1625
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