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 .
DETAILED ACTION
Claims 1-17 are currently pending in the application.
Priority
Applicant’s claim for the benefit of a prior-filed application under 35 U.S.C. 119(e) or under 35 U.S.C. 120, 121, or 365(c) is acknowledged. The earliest application that provides adequate support or enablement in the manner provided by the first paragraph of 35 U.S.C. 112 for one or more claims of this application is the Indian application No. 202121030667. Thus, the priority date of the instant invention is July 08, 2021.
IDS
The information disclosure statement (IDS) submitted on 01/4/24 is acknowledged and has been entered. The submission is in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statement has been considered by the examiner.
Objections
Claims 1 and 6 are objected to because of extra spaces in the claims. Specifically, claim 1 contains an extra space between “atoms” and “of the…” and claim 6, line 2 has an extra space between “contain” and equal. 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 primary purpose of this requirement of definiteness of claim language is to ensure that the scope of the claims is clear so the public is informed of the boundaries of what constitutes infringement of the patent. A secondary purpose is to provide a clear measure of what applicant(s) regard as the invention so that it can be determined whether the claimed invention meets all the criteria for patentability and whether the specification meets the criteria of 35 U.S.C. 112, first paragraph with respect to the claimed invention.", (see MPEP § 2173).
Claim 10 is rejected under 35 U.S.C. 112, second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which applicant regards as the invention.
Firstly, claim 10 recites that the variables have specific meaning for n; R, R1, and R2. However, it is unclear which formula is applicant referring to. Are the definitions to be applied to the nitrile compound of Formula (IIb) or to the amidoxime yield product of Formula (Ib)?
As a result of the above inconsistencies, the aforementioned claims are unable to be examined as disclosed given that the scope of the claimed subject matter would not be able to be determined by one of ordinary skill in the art.
Claim Rejections - 35 USC § 103
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
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 of this title, 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 set forth in Graham v. John Deere Co., 383 U.S. 1, 148 USPQ 459 (1966), that are applied 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 1-9 are rejected under pre-AIA 35 U.S.C. 103(a) as being unpatentable over Voros et al. (Organic & Biomolecular Chemistry, 2014, Vol. 12, No. 2399, pgs. 8036-8047; cited and filed on an IDS 1449).
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Voros et al. teach a study of reaction mechanism between nitriles and hydroxylamines (see abstract). Specifically, Voros et al. teach a scheme 4 wherein benzonitrile (instant formula IIb with no Ra and n as 0; instant claim 8) is reacted with ethanol to yield BAO or benzamidoxime at 96% product yield (see scheme 4, pg. 8041).
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Additionally, Voros et al. teach substituents on the phenyl group did not affect the reaction while in a protic solvent (i.e. ethanol) at a temperature of 50 ºC and wherein substituents such as halogen and nitro led to increased product yield (see pg. 8039, right col., last paragraph). Voros et al. also teach scheme 7 with a protic solvent (ethanol) and an organic base Et3N wherein the ratio is one molecule of EtOH, one molecule of Et3N, and one Et3NH+ (see pg. 8041-8042) resulting in a benzamidoxime product as shown in scheme 4 (i.e. BAO; see figure 2). While Voros et al. is silent on the metering step, the experimental section of Voros et al. clearly teaches 1 equivalent of benzonitrile (51.5mg or 0.5g or 0.5mmol) was added to 0.5ml (i.e. 4x10-4 kg) of EtOH resulting in a 1:1 stoichiometry at 50ºC, stirred, and checked by HPLC method at 30 minutes (see pg. 8045 and table 2). This suggests that Voros et al. did indeed practice metering of the reaction as the goal of Voros et al. was to minimize side products yield.
Voros et al. do not specifically teach a benzonitrile substituted with a methyl group; do not teach the exact amount of benzonitrile to solvent; or failed to teach the exact reaction time of 1hour or more than 1 hour.
The examiner however contends that such amounts and reaction time would be optimized during routine experimentation as the goal of Voros et al. is to yield the major product, BAO, while minimizing any other side products. Additionally, Voros et al. teach that when low yield came about, a change to longer reaction time increased the yield somewhat.
While the exact compound of formula I (benzamidoxime) is not disclosed by Voros et al. and is not substituted by a methyl group, it is generally noted that the substitution of methyl for hydrogen on a known compound is not a patentable modification absent unexpected or unobvious results. In re Lincoln, 126 U.S.P.Q. 477, 53 U.S. P.Q. 40 (C.C.P.A. 1942); In re Druey, 319 F.2d 237, 138 U.S.P.Q. 39 (C.C. P.A. 1963); In re Lohr, 317 F.2d 388, 137 U.S.P.Q. 548 (C.C.P.A. 1963); In re Hoehsema, 399 F.2d 269, 158 U.S.P.Q. 598 (C.C.P.A. 1968); In re Wood, 582 F.2d 638, 199 U.S. P.Q. 137 (C.C.P.A. 1978); In re Hoke, 560 F.2d 436, 195 U.S.P.Q. 148 (C.C.PA.A. 1977); Ex parte Fauque, 121 U.S.P.Q. 425 (P.O.B.A. 1954); Ex parte Henkel, 130 U.S.P.Q. 474, (P.O.B.A. 1960). Given that applicant did not provide unexpected or unobvious results of the invention, it is concluded that the normal desire of scientists or artisans to improve upon what is already generally known would provide the motivation to substitute the “H” group to a “methyl”.
Thus, to one of ordinary skill in the art at the time of the invention would have found it obvious to follow the teachings of Voros et al. since Voros et al. teach the study was conducted in order to determine the best mechanisms of reaction between nitriles and hydroxylamine that could lead to decreased by-products and purification issues. Given the teachings of Voros et al., one of ordinary skill would have been motivated to utilize the method of Voros et al. to formulate benzamidoxime with the reasonable expectation of providing a method that is useful in lowering purification issues as well as a method that leads to a high yield of amidoxime product.
Claims 11-17 are rejected under pre-AIA 35 U.S.C. 103(a) as being unpatentable over Voros et al. (Organic & Biomolecular Chemistry, 2014, Vol. 12, No. 2399, pgs. 8036-8047; cited and filed on an IDS 1449) as applied to claims 1-9 in view of Koradin et al. (WO 2019/020451A1).
The Voros et al. reference is as discussed above and is incorporated by reference herein. However, Voros et al. do not teach converting the benzamidoxime into a 1,2,4-oxadiazole.
Koradin et al. teach method of preparing formula I (i.e. instant formula IV; instant claim 11) wherein R2 can be H and R1 can be a methyl group (instant claim 17; see pg.3):
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via reaction of an amidoxime and TFAA wherein A1 & A2 are CH; RA is H; and R is methyl (see abstract and pgs. 1 & 3). Additionally, Koradin et al. teach that this method is cost-efficient eco-friendly (see pg. 3). Koradin et al. further teach that formula I can further be converted into chemical products and intermediates (see pgs. 8-9) including formula Ib (i.e. instant formula IVa; instant claim 12) when R is a methyl group and said compound is further fluorinated:
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.
Koradin et al. also teach hydrolysis of formula Ib to yield formula III (i.e. instant formula V; instant claim 14; see pg. 9):
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. Koradin et al. also teach hydrolysis of formula Ib with a trichloromethyl group which would lead to (COOH; instant claim 13; see pg. 9). Additionally, Formula III can be reacted with an amine (R1-N-R2) to yield formula Ic (see pg. 10; instant formula VII; instant claim 15):
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.
Koradin et al. also teach the use of formula Ic to obtain formula Id:
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(see pg. 10; instant formula VIII; instant claim 16).
Thus, to one of ordinary skill in the art at the time of the invention would have found it obvious to follow the teachings of Voros et al. and Koradin since Voros et al. teach the study was conducted in order to determine the best mechanisms of reaction between nitriles and hydroxylamine that could lead to decreased by-products and purification issues and in light of Koradin who teaches that such method is cost-efficient and friendly to the environment. Given the teachings of Voros and Koradin et al., one of ordinary skill would have been motivated to utilize the modified method of Voros and Koradin et al. to formulate derivatives of 1,2,4-oxadiazole with the reasonable expectation of providing a method that is useful in lowering purification issues and a method useful in reducing cost.
Conclusion
Claims are not allowed.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Director Bonnie Eyler whose telephone number is 571-272-1200. The Supervisory Primary Examiner can normally be reached on 12:00-8:00 PM EST M-F at 571-270-3503. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/SAMIRA J JEAN-LOUIS/Supervisory Patent Examiner, Art Unit 1642