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 of 18/569,414
This Office Action is responsive to the amended claims and Applicant remarks of 05/12/2026. Claims 1-9 and 11-21 are pending and have been examined on the merits.
Priority
The instant application is a national stage entry of PCT/US22/33662, filed 06/15/2022, which claims priority to PCT/CN2021/100305, filed 06/16/2021.
Information Disclosure Statement
The information disclosure statement (IDS) submitted on 02/23/2026 is in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statement is being considered by the examiner.
Response to Arguments
Objections:
Applicants have amended claim 5, removing “any” from the claim. This amendment renders the previous object to the claim moot. The objection is withdrawn.
35 U.S.C. §112(b)
Applicants have cancelled claim 10, corrected claim dependency issues in claim 12, removed “more” from claim 13, and replaced “preferably” and “more preferably” with “optionally” in claim 14. These amendments are sufficient to overcome the previous rejections for claims 10 and 12. However, claims 13 and 14 remain indefinite. As written, the claims do not clearly define the metes and bounds of the solvents listed after the phrase “optionally.” It is unclear whether the listed solvents are required alternatives for A, optional additional components, non-limiting examples of suitable organic solvents, or merely preferred embodiments.
35 U.S.C. §103
Applicants allege that the claimed compound and method of preparing the compound of Formula I are known, but that the methods are directed to amorphous solids, not crystalline forms. Applicants argue that Nissan is not concerned with large-scale production of crystalline forms or crystalline properties, such as hygroscopicity. The arguments regarding large-scale production and crystalline properties are not persuasive because these limitations are not recited in the claims and are therefore not required by the claims. These arguments are not commensurate with the claimed scope of the invention.
Synthetic Example 21 of Nissan [0264] teaches that compounds within the same disclosed class are amenable to isolation as crystalline solids using conventional organic solvent conditions. The instant claims do not require a particular solvent or solvent system in a specified ratio. Instead, the claims are drawn to one or more components of A, wherein A is an organic solvent suitable for dissolving the compound of Formula 1. In view of Nissan’s disclosure that compounds of this class are obtainable as crystalline solids using conventional organic solvents, and given the routine use of organic solvents in crystallization and isolation of small molecule compounds, the artisan would reasonably expect that a crystalline solid of the claimed compound could be obtained using a suitable organic solvent.
Applicants allege that Caira does not teach or suggest methods of preparing crystalline forms of compounds, including methods for producing the crystalline forms of compounds of Formula 1. These arguments are not persuasive. The reference expressly teaches that recrystallization of compounds from solvents or solvent mixtures spanning a wide polarity range is effective at producing polymorphs suitable for complete characterization. The reference also teaches that most substances, when thoroughly investigated will reveal one or more polymorphs.
Based on the combined teachings of the references discussed above, the artisan would have been motivated to screen suitable organic solvents or solvent mixtures to crystallize and characterize the compound. The artisan would have reasonably expected to obtain at least one crystalline polymorph from. The specifically claimed crystalline forms merely characterize solid forms obtained through routine polymorph screening of a compound class known to be amenable to organic solvent crystallization. Because the claims do not require a specific solvent system, the recited XRPD values of the claimed compounds represent the expected products of routine screening rather than a patentable distinction over the prior art.
Applicants argue that Vogel is directed to general recrystallization techniques and does not specifically teach or suggest the claimed compound or process for obtaining the compound. Applicants further argue that Vogel does not teach or suggest the specific solvent, temperature, time, or other conditions of the instant claims. These arguments are not persuasive.
The claims do not require the specific recrystallization conditions Applicants allege in their arguments. Rather, the claims only require that the recrystallization process use an organic solvent suitable for dissolving the compound. The claims do not recite or require any particular solvent, solvent mixture, temperature, time, or any other process parameter. Applicants’ arguments rely on limitations drawn from the specification that are not present in the claims.
Claim Rejections - 35 USC § 112
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 13 and 14 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.
Claims 13 and 14 do not clearly define the metes and bounds of the solvents listed after the phrase “optionally.” It is unclear whether the listed solvents are required alternatives for A, optional additional components, non-limiting examples of suitable organic solvents, or merely preferred embodiments.
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.
Claims 1-3, 6-9, 11, 17-18, and 20-21 are rejected under 35 U.S.C. 103 as being unpatentable over Nissan (EP 1731512 A1, found in IDS filed 12/12/2023) in view of Caira (“Crystalline Polymorphism of Compounds” Topics in Current Chemistry, Vol 198, pgs. 163-208 (1998), found in IDS filed 12/12/2023).
Nissan discloses the same compound of Formula 1 of the instant application and teaches methods of using the compound for controlling pests (see Abstract and [0001]). Page 61, line 20 of the reference discloses the scaffold [1]-11
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and defines the variables on [1]-11 on page 189, line 39 as being
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. These substitutions define the same compound of the instant claims 1 and 7. [0176] teaches that these compounds can be mixed with suitable carriers, reading on instant claims 3 and 9. The reference describes structurally related compounds prepared by similar synthetic routes and isolated as crystalline solids (Synthetic Examples 1-28, [0202-0269]). This teaching supports that crystallization of compounds within this class is routine and expected. The artisan would be motivated to investigate and characterize crystalline forms of the known compound using conventional methods. Nissan does not expressly disclose crystalline polymorphs of the claimed compound, does not provide XRPD data, and does not describe a recrystallization procedure for obtaining specific crystal forms. However, as recognized in the art, crystalline polymorphs of pharmaceutical compounds are routinely identified and characterized using standard solid-state techniques such as XRPD. Likewise, recrystallization procedures for obtaining crystalline forms are well known and within the ordinary skill of the art.
Caira teaches that the systematic investigation of a compound’s propensity for polymorphism is routine in the art (pg. 165, final para). The reference further teaches that most substances, when investigated sufficiently, will reveal one or more polymorphs (pg. 165-166). Additionally, Caira teaches that the methods for screening polymorphs are well known in the art, and that recrystallization is a frequently employed technique for obtaining crystalline forms, using a wide range of solvents or solvent mixtures to afford the products in sufficient quantities for complete characterization (see Chapter 3.1).
The artisan would have experience in the development and characterization of small-molecule pharmaceutical compounds, including synthesizing known compound, purifying them, isolating solid forms, investigating polymorphism, and evaluating physical properties of pharmaceutically relevant compounds.
The prior art teaches the claimed compound and its application to pest control, and the compound has been known in the art for an extended period of time. As taught by Caira, compounds that are investigated sufficiently often reveal multiple crystalline polymorphs, and the systematic investigation and screening of polymorphs is a routine aspect of pharmaceutical development.
The artisan would have been motivated to isolate and screen crystalline forms of the known compound using routine methods. Although the artisan would not have expected to obtain the specific XRPD values recited in the claims in advance, routine polymorph screening would reasonably lead to the identification of one or more crystalline forms of the compound.
Once such crystalline forms were identified, it would have been routine to evaluate their physical properties and select form with the most desirable properties for pharmaceutical development. The claimed crystalline forms of instant claims 1 and 7 therefore represent the results of routine investigation and selection.
Instant claims 2 and 7 further limit the compound to a specified purity. However, the references teach the compound and disclose methods of purification such as chromatography and recrystallization, that are routinely employed in the art. The selection of a particular purity level represents optimization of a results-effective variable within the ordinary skill in the art and does not patentably distinguish the claimed compound absent a showing of criticality or unexpected results.
Claim 6 does not further limit the crystalline form beyond what is already recited in claim 1. The recited method of preparation does not impart any structural or functional distinction to the claimed crystalline form. Accordingly, claim 6 is coextensive with instant claim 1 and is unpatentable for the same reasons as claim 1.
Claim 11 is an intended use claim that does not meaningfully limit the pharmaceutical composition of claim 3. Therefore, claim 11 is coextensive with instant claim 3 and is unpatentable for the same reasons as claim 3.
Claims 17 and 20 are rejected for the reasons set forth with respect to claims 1 and 7. The additionally claimed XRPD peaks merely provide further characterization of the crystalline forms and do not require a solvent system that distinguishes them from the crystalline forms expected from routine polymorph screening.
Claims 18 and 21 are rejected for the reasons set forth above for claims 1 and 7. The additionally claimed DSC exothermic peaks merely provide further analytical characterization of the claimed crystalline forms that would have been obtained and characterized through routine polymorph screening.
Claims 1 and 4-5 are rejected under 35 U.S.C. 103 as being unpatentable over Nissan and Caira in view of Vogel (Furniss, B., Hannaford, A., Smith, P., & Tatchell, A. (1989). Vogel’s textbook of Practical Organic Chemistry. Longman).
The teachings of Nissan and Caira are discussed above and are incorporated by reference into this rejection. They teach claim 1. The references do not expressly disclose the recrystallization process of instant claims 4 and 5. However, the claimed processes represent conventional recrystallization techniques within the ordinary skill of the art as taught by Vogel.
Claims 4 and 5 are directed to methods of preparing the crystalline form of the compound of Formula 1 by dissolving the compound in one or more organic solvents and optionally adding an antisolvent to reduce solubility, followed by isolation of the resulting compound. These steps are conventional recrystallization techniques. It is well-known in the art that solvent selection is key variable in recrystallization and that mixed-solvent systems are routinely used (see Vogel pg. 135-139). It is similarly well-known that these mixed-solvent systems can include a secondary solvent that reduces solubility and induces crystallization of the desired product (see Vogel pg. 138 second para). Routine screening of solubility across solvents and use of a mixed solvent system when a single solvent is not appropriate is also established in the art (see Vogel pg. 135-139). The breadth of claims 4 and 5, which permit recrystallization using essentially any of a wide range of conventional solvents or solvent systems, supports the conclusion that the claimed methods reflect routine experimentation rather than a nonobvious process. Where no critical parameter or unexpected result is demonstrated, such broad claims do not rise above the ordinary skill in the art.
Conclusion
No claims are allowed.
Claims 16 and 19 are objected to for being dependent upon a rejected base claim.
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 CONNOR KENNEDY ENGLISH whose telephone number is (571)270-0813. The examiner can normally be reached Monday Friday, 8 a.m. 5 p.m. ET..
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/C.K.E./ Examiner, Art Unit 1625 /Andrew D Kosar/Supervisory Patent Examiner, Art Unit 1625
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