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 of 12/12/2023, claims 1-15 are pending and have been examined on the merits.
Priority
Applicants identify the instant application as 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 statements (IDS) submitted on 12/12/2023, 06/06/2024, and 08/13/2024 are in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statement is being considered by the examiner.
Drawings
The drawings are objected to because the figures are all grainy and difficult to interpret. Figures 48, 49, 51, 56-58, and 67-68 are especially bad and the axis labels are unreadable. The examiner suggests replacing ALL figures with clear legible figures. Corrected drawing sheets in compliance with 37 CFR 1.121(d) are required in reply to the Office action to avoid abandonment of the application. Any amended replacement drawing sheet should include all of the figures appearing on the immediate prior version of the sheet, even if only one figure is being amended. The figure or figure number of an amended drawing should not be labeled as “amended.” If a drawing figure is to be canceled, the appropriate figure must be removed from the replacement sheet, and where necessary, the remaining figures must be renumbered and appropriate changes made to the brief description of the several views of the drawings for consistency. Additional replacement sheets may be necessary to show the renumbering of the remaining figures. Each drawing sheet submitted after the filing date of an application must be labeled in the top margin as either “Replacement Sheet” or “New Sheet” pursuant to 37 CFR 1.121(d). If the changes are not accepted by the examiner, the applicant will be notified and informed of any required corrective action in the next Office action. The objection to the drawings will not be held in abeyance.
Claim Objections
Claim 5 is objected to because of the following informalities: the phrase “according to any claim 1” is improper, as claim 1 is singular and the term “any” implies multiple antecedent claims. The dependency is therefore unclear. This objection can be rendered moot but the removal of the word “any” from the claim. Appropriate correction is required.
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 10 and 12-14 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.
Claim 12 recites the limitation "said pest" in line 1. There is insufficient antecedent basis for this limitation in the claim. The phrase above lacks proper antecedent basis because neither claim 1 nor 3 introduces or defines “pests”. It is therefore unclear what the term “said pests” refers.
Claim 10 recites the limitation “wherein the crystalline form makes up 80% or more of a total amount of the compound of Formula 1 in the pharmaceutical composition.” It is unclear whether the limitation requires (a) at least 80% of the compound of Formula 1 present in the composition is in the claimed crystalline form, or (b) the crystalline form constitutes at least 80% of the total pharmaceutical composition. These interpretations define materially different scopes. The claim fails to clearly define the metes and bounds of the claims and is therefore indefinite.
Regarding claim 13, the phrase "more optionally" renders the claim indefinite because it is unclear whether the limitation(s) following the phrase are part of the claimed invention. See MPEP § 2173.05(d).
Regarding claim 14, the phrases "preferably" and “more preferably” render the claim indefinite because it is unclear whether the limitation(s) following the phrase are part of the claimed invention. See MPEP § 2173.05(d).
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 and 11 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
PNG
media_image1.png
158
296
media_image1.png
Greyscale
and defines the variables on [1]-11 on page 189, line 39 as being
PNG
media_image2.png
53
625
media_image2.png
Greyscale
. 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 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.
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..
Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Andrew Kosar can be reached at (571)272-0913. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
/C.K.E./ Examiner, Art Unit 1625 /Andrew D Kosar/Supervisory Patent Examiner, Art Unit 1625