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 .
Information Disclosure Statement
The information disclosure statements (IDS) submitted on April 19th, 2023; and October 12th, 2023 are in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statements are being considered by the examiner.
Status of the Claims
Claims 1-13 are pending in this application.
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.
Claim 13 is 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 regards as the invention.
Claim 13 speaks to the method wherein the methane sulfonyl chloride (MsCl) used in step-(i) is separated, recovered, and recycled.
Applicant is directed to Example 1 of the instant specification (page 7) wherein a total of 12 g (about 105 mmol) of MsCl is used to mesylate 31 g (about 103 mmol) of 3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxylic acid (hereafter compd. 4). Theoretically, for every 1 mol of compd. 4, 1 mol of MsCl is needed. Therefore, the instant conditions use a very small excess of about 2 mmol of MsCl.
Similar to what was described above, for every 1 mol of 2-amino-5-chloro-3 methyl benzoic acid added (hereafter compd. 3), 1 additional mol of MsCl is needed for the reaction to go to completion. In the second part of step-(i), 19 g of compd. 3 (about 102 mmol) are added, followed by another 12 g MsCl (second portion, about 105 mmol), resulting in another small theoretical excess of about 3 mmol of MsCl.
Thus, theoretically, a total of about 5 mmol excess MsCl (about 2.3% of the total MsCl added) is leftover after the reaction is complete. The remaining about 97.6% of the MsCl is used (reacted), and is therefore rendered inseparable, unrecoverable, and unrecyclable.
It is unclear from the claim language and the disclosure how applicant intends to separate, recover, or recycle the used MsCl, when most of it has been reacted and hydrolyzed during the reaction.
Does applicant intend to: (i) somehow regenerate the MsCl after it has reacted during the process, thus allowing for the “MsCl used in step-(i) to be separated, recovered, and recycled;” or (ii) separate, recover, and recycle that small excess that is theoretically left in the reaction mixture after the transformation is complete?
For the purposes of applying art, it will be assumed that applicant intends to separate, recover, and recycle the small excess leftover after the reaction is complete. If this was the Applicant’s intention, examiner suggests amending claim to read “wherein excess methane sulfonyl chloride used in step-(i) is separated, recovered, and recycled.”
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.
Claims 1-8 and 10-13 are rejected under 35 U.S.C. 103 as being unpatentable over Lahm et al. (US 7,232,836 B2).
Regarding claims 1 and 4, Lahm discloses a process for the preparation of the compounds of Formula I below (col. 2), anticipating the instant compound of Formula I (chlorantraniliprole) when R1 is -CH3; R2 and R5 are -Cl; R3 is -Br; R4a is C1-alkyl; and R4b is H. Lahm specifically discloses these variables for chlorantraniliprole in Table 1, col. 34, line 46.
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Lahm teaches chlorantraniliprole can be synthesized from the reaction of benzoxazinone intermediate 2 below with the desired amine (R4aR4bNH) (col. 5, Scheme 1), reading on step-(ii) of claim 1.
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Intermediate 2 (with variables as defined above) can be prepared from 3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxlic acid (4) and 2-amino-5-chloro-3-methylbenzoic acid (3), using methane sulfonyl chloride and an organic base (tertiary amine) such as triethylamine (col. 5, Scheme 2), reading on step-(i) of claim 1.
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Further regarding claims 1 and 4, while Lahm does not teach use of an inorganic base for this particular step, Lahm discloses a different step which utilizes a base (alkylation of 17a to 17b below) (col. 14, Scheme 12). Lahm teaches suitable bases can be inorganic bases, such as lithium/ sodium/ potassium carbonates or hydroxides; or organic bases, such as triethylamine. Lahm further teaches the alkylation below can be carried out in solvents like acetonitrile, etc. (col. 14, para. 2, lines 9-18).
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The key to supporting any rejection under 35 U.S.C. 103 is the clear articulation of the reasons why the claimed invention would have been obvious. The Supreme Court in KSR noted that the analysis supporting a rejection under 35 U.S.C. 103 should be made explicit. The Court quoting In re Kahn, 441 F.3d 977, 988, 78 USPQ2d 1329, 1336 (Fed. Cir. 2006), stated that "‘[R]ejections on obviousness cannot be sustained by mere conclusory statements; instead, there must be some articulated reasoning with some rational underpinning to support the legal conclusion of obviousness.’" KSR, 550 U.S. at 418, 82 USPQ2d at 1396. See also Adapt Pharma Operations Ltd. v. Teva Pharms. USA, Inc., 25 F.4th 1354, 1365, 2022 USPQ2d 144 (Fed. Cir. 2022) (stating that a determination of obviousness "requires ‘identify[ing] a reason that would have prompted a person of ordinary skill in the relevant field to combine the elements in the way the claimed new invention does’" (quoting KSR, 550 U.S. at 418, 82 USPQ2d at 1395). Examples of rationales that may support a conclusion of obviousness include:
(A) Combining prior art elements according to known methods to yield predictable results;
(B) Simple substitution of one known element for another to obtain predictable results;
(C) Use of known technique to improve similar devices (methods, or products) in the same way;
(D) Applying a known technique to a known device (method, or product) ready for improvement to yield predictable results;
(E) "Obvious to try" – choosing from a finite number of identified, predictable solutions, with a reasonable expectation of success;
(F) Known work in one field of endeavor may prompt variations of it for use in either the same field or a different one based on design incentives or other market forces if the variations are predictable to one of ordinary skill in the art;
(G) Some teaching, suggestion, or motivation in the prior art that would have led one of ordinary skill to modify the prior art reference or to combine prior art reference teachings to arrive at the claimed invention.
In view of prong B above, the instant invention speaks to a mere substitution of triethylamine (an organic base, as taught by Lahm, used to quench hydrochloric acid produced after mesylation of the carboxylic acid) for an inorganic base, as disclosed by Lahm, such as sodium/ potassium hydroxide or sodium/ potassium carbonate, leading to a predictable similar quenching of the HCl produced after mesylation of the carboxylic acid.
Regarding claims 2-3, Lahm discloses their first fluid medium, for the reaction of 4 and 3 to yield the benzoxazinone intermediate 2 (as shown above) in acetonitrile (Example 1, Step D, col. 17, lines 35-56).
Regarding claim 6, Lahm discloses addition of an amine R4aR4bNH to their intermediate 2, wherein R4a can be C1-alkyl and R4b can be H, reading on methylamine.
Regarding claim 7, Lahm discloses purification of their benzoxazine intermediate by column chromatography prior to reaction with the organic amine (Example 3, Step E, col. 19, lines 64-66), wherein the organic amine can be R4aR4bNH, wherein R4a can be C1-alkyl and R4b can be H, reading on methylamine. Lahm discloses the reaction can be run neat or in a variety of solvents, including tetrahydrofuran (THF), diethyl ether (Et2O), dichloromethane (DCM), or chloroform, with optimum temperatures ranging from room temp. to reflux (col. 5, lines 30-35).
Regarding claim 8, Lahm discloses benzoxazinone 2 stirring with methylamine in THF, at room temperature, for 5 minutes (Example 2, col. 18, lines 20-26).
Regarding claim 5, Lahm discloses their reaction mixture was allowed to stir at room temperature overnight (Example 1, Step D, col. 17, lines 35-56; or Example 3, Step E, col. 19, lines 60-64).
Regarding the instantly claimed temperature and time ranges in claims 5 and 8, Applicant is advised that the courts have stated where the claimed ranges overlap or lie inside the ranges disclosed by the prior art and even when the claimed ranges and prior art ranges do not overlap but are close enough that one skilled in the art would have expected them to have similar properties, a prima facie case of obviousness exists. See In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976); In re Woodruff, 919 F.2d 1575, 16 USPQ2d 1934 (Fed. Cir. 1990); Titanium Metals Corp. of America v. Banner, 778 F2d 775. 227 USPQ 773 (Fed. Cir. 1985) (see MPEP 2144.05.01). The courts have also found that where the general conditions of a claim are disclosed in the prior art, it is not inventive to discover the optimum or workable ranges by routine experimentation. See In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955). See MPEP 2144.05-II.
Therefore, the claimed ranges merely represent an obvious variant and/or routine optimization of the values of the cited prior art.
Regarding claim 10, Lahm discloses dropwise addition of methane sulfonyl chloride as an acetonitrile solution (reading on addition in portions) (Example 1, Step D, col. 17, lines 37-40). Lahm also discloses dropwise addition of a pyridine (organic base) solution in acetonitrile to the reaction mixture (reading on addition in portions) (Example 13, col. 32, lines 25-30).
Regarding claim 11, Lahm discloses their process wherein the weight ratio of base to carboxylic acid is 5.88 g/ 15.0 g (in Example 3, Step E, col. 19, lines, lines 50-52), which equates a weight ratio of about 0.4:1.
Regarding claim 12, Lahm discloses their process wherein the weight ratio of carboxylic acid to methane sulfonyl chloride is 15.0 g/ 6.96 g (in Example 3, Step E, col. 19, lines, lines 48-52), which equates a weight ratio of about 2.2: 1.
Further regarding claims 11-12, Applicant is reminded that the courts have stated where the claimed ranges overlap or lie inside the ranges disclosed by the prior art and even when the claimed ranges and prior art ranges do not overlap but are close enough that one skilled in the art would have expected them to have similar properties, a prima facie case of obviousness exists. The courts have also found that where the general conditions of a claim are disclosed in the prior art, it is not inventive to discover the optimum or workable ranges by routine experimentation.
Therefore, the claimed ranges merely represent an obvious variant and/or routine optimization of the values of the cited prior art.
Regarding claim 13, Applicant is advised that the subject matter of a properly construed claim is defined by the terms that limit its scope. It is this subject matter that must be examined. As a general matter, the grammar and intended meaning of terms used in a claim will dictate whether the language limits the claim scope. Language that suggests or makes optional but does not require steps to be performed or does not limit a claim to a particular structure does not limit the scope of a claim or claim limitation. “Wherein” clauses are examples of language that may raise a question as to the limiting effect of the language in a claim. See MPEP 2103 I.C. and MPEP § 2111.04.
It is also noted that a “wherein” clause, such as that in claim 13, must give “meaning and purpose to the manipulative steps.” See, MPEP § 2111.04.
Claim 9 is rejected under 35 U.S.C. 103 as being unpatentable over Lahm et al. (US 7,232,836 B2); as applied to claims 1-8 and 10-13, in view of Allendörfer et al. (Tetrahedron Letters, 53, 2012, 388–391).
The teachings of Lahm et al. are disclosed above and incorporated herein.
Lahm discloses opening of their intermediate 2 by an amine can be run in a variety of suitable solvents including THF, Et2O, DCM, or chloroform (col. 5, lines 31-35) (corresponding to instantly claimed second fluid medium).
While Lahm does not specifically teach their process wherein the solvent corresponding to the instantly claimed second fluid medium is acetonitrile, the teachings of Allendörfer et al. are relied upon for these disclosures.
Allendörfer discloses a solvent screen for the opening of benzoxazinones similar to Lahm’s intermediate 2 (disclosed above) (Scheme 2 and Table 2, page 389). Allendörfer discloses the reaction being performed in Et2O, THF, and acetonitrile (MeCN) (shown in the table below) resulted in similar yields of 68, 76, and 65%, respectively, for their product 4a.
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Although Allendörfer’s reaction doesn’t involve addition of an amine to their benzoxazinone derivative of formula 2, Applicant is advised that a person with ordinary skill has good reason to pursue known options within his or her technical grasp. Note: MPEP 2141 [R-6] KSR International CO. v. Teleflex Inc. 82 USPQ 2d 1385 (Supreme Court 2007).
Therefore, it would have been prima facie obvious to one of ordinary skill prior to the effective filing date of the instant application to try Lahm’s benzoxazinone 2 ring opening reaction with amines HNR4aR4b in acetonitrile, in view of Allendörfer. One of ordinary skill would have been motivated to do so with a reasonable expectation of success in view of Lahm’s teachings that opening of their intermediate 2 by an amine can be run in a variety of suitable solvents including THF, Et2O, DCM, or chloroform; and Allendörfer’s disclosure that THF, Et2O, and MeCN led to similar results in a similar transformation.
Therefore, the claimed invention, as a whole, would have been prima facie obvious to one of ordinary skill in the art before the effective filing date of the instant invention, because the combined teachings of the prior art references is fairly suggestive of the claimed invention.
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 1-12 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claim 1-8 of copending Application No. 17/782,807 (Copending ‘807).
Regarding instant claims 1-12, Copending ‘807 speaks to a process for the preparation of chlorantraniliprole (Copending ‘807 claims 1-8) with 3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxylic acid, 2 amino-5-chloro-N-3-dimethylbenzamide, an inorganic base, and RSO-2Cl, wherein R can be C1 alkyl (methyl).
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This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Claims 1-13 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1 and 14-15 of copending Application No. 18/284,735 (Copending ‘735).
Regarding instant claims 1-12, Copending ‘735 speaks to a process for the preparation of chlorantraniliprole (Copending ‘735 claim 1, step-iii) comprising reacting intermediate with 3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxylic acid (intermediate B), 2-amino-5-chloro-3-methylbenzoic acid (intermediate A), an inorganic base, and methane sulfonyl chloride, and methyl amine (Copending ‘735 claim 14).
Regarding instant claims 13, Copending ‘735 speaks to their process wherein the methanesulfonyl chloride is recovered and reused.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to JACKSON J HERNANDEZ whose telephone number is (571)272-5382. The examiner can normally be reached Mon - Thurs 7:30 to 5.
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/JACKSON J HERNANDEZ/Examiner, Art Unit 1627
/Kortney L. Klinkel/Supervisory Patent Examiner, Art Unit 1627