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 .
Status of Claims
The amendments to the claims filed July 17, 2024 are acknowledged and entered. Claims 1, 3, 5-6, 8, 10-12, 14-15, 17, 19, 22, 24, 35, 38, 48, 75 and 77-78 are pending.
Priority
This application is a 371 of PCT/US2023/010974, filed January 17, 2023, which claims the benefit of 63/300,473, filed January 18, 2022.
Information Disclosure Statement
Acknowledgement is made of the Information Disclosure Statement filed on March 18, 2026. All references have been considered except where marked with a strikethrough.
Specification
The disclosure is objected to because of the following informalities:
The specification lists Figure 12C (see paragraph [0028]); however, there does not appear to be any Figure 12C in the drawings filed July 17, 2024.
Appropriate correction or clarification is required.
The specification has not been checked to the extent necessary to determine the presence of all possible minor errors. Applicant’s cooperation is requested in correcting any of the errors of which applicant may become aware of in the specification.
Claim Objections
The claims are objected to for the following informalities:
Claim 38 recites “provided…R4 is selected from…-B(R14)3” and should recite “provided…R4 is selected from…-B(R14)3X”.
Appropriate correction is required.
Claim Rejections - 35 USC § 112b
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 12, 15, 19 and 77-78 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. The claims are indefinite for the reasons that follow:
Claims 12, 15, 19 and 77-78 recite “claim 0” which renders the scope of the claims indefinite because there is no “claim 0”. Examiner suggests amending the claim to depend from an existing claim.
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.
Claim(s) 38 and 48 is/are rejected under 35 U.S.C. 103 as being unpatentable over Hert et al. (WO2017/037146 A1)(hereinafter “Hert”).
Hert teaches compounds of generic formula (I) that are useful for treating disease such as cancer (page 1). Hert teaches a method of preparing formula (I) which requires making a borylated amidoxime, or boronate ester, of formula
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wherein the group corresponding to instant R3 is -B(OR12)2 and R12 is a C2 heterocyloalkyl substituted with 4 C1 alkyl groups by reacting an aryl cyanide of formula
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with hydroxylamine (see pages 195-196; steps 1 and 2). Hert does not teach an embodiment wherein the group corresponding to R3 is in the para position relative to the amidoxime group as required by the claims; however, Hert generically teaches that the group corresponding to instant R3 can be located in the para position relative to amidoxime group (see pages 126-127, Scheme 28, intermediates C89 can be transformed into an amidoxime group by methods known in the art, for example by reaction with hydroxylamine; scheme pictured below for convenience).
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The difference between the prior art method and the claimed method is that the claimed method requires R3 to be in the para position relative to the amidoxime group. However, it would have been prima facie obvious to one having ordinary skill in the art before the effective filing date of the claimed invention to modify the prior art method into the claimed method because Hurt disclosed that the group corresponding to instant R3 could be in the para position relative to the amidoxime group as required by the claims.
One would have been motivated as a matter of preparing analogs of formula (I) for treating diseases such as cancer.
One would have had a reasonable expectation of success because Hert already explicitly disclosed a method of preparing a borylated amidoxime of formula
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by reacting an aryl cyanide with hydroxylamine and further taught that this method could be used to prepare borylated amidoximes of the claims.
Claim(s) 75 and 77-78 is/are rejected under 35 U.S.C. 103 as being unpatentable over Hert et al. (WO2017/037146 A1)(hereinafter “Hert”) in view of Molander et al. (Acc. Chem. Res. 2007, 40, 275-286)(hereinafter “Molander”).
Hert teaches a borylated amidoxime, or boronate ester, of formula
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for making compounds of formula (I) as noted in the rejection above, the teachings of which are incorporated herein by reference.
Hert does not teach the required R20 and X groups of the claims; however, Molander teaches trivalent organoboron species (e.g. boronate esters, boronic acids) have numerous disadvantages (e.g. boronate esters have marked decrease in atom economy) in organic synthesis and that if more robust organoboron reagents were available then this would tremendously expand the range of retrosynthetic pathways using Suzuki coupling reactions as key transformations in complex molecule synthesis (Introduction). Molander teaches organotrifluoroborates are compounds comprised of a boron atom bound to three fluorine atoms and a counterion (see Figure 2, ArylBF3K). Molander teaches the trifluoroborate moiety is stable toward numerous reagents that are often problematic for other boron species. Consequently, remote functional groups within the organotrifluoroborates can be manipulated, while retaining the valuable carbon-boron bond (Abstract). Molander teaches the organotrifluoroborates have proven to be extremely versatile in their ability to partake in cross-coupling transformations. In the fullness of time, it would appear that they will be at least as competent as, and in some instances superior to, other organoboron reagents in terms of their ability to undergo cross-coupling with a variety of suitable electrophilic partners (page 281, col 1, paragraph 2).
The difference between formula
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of Hert and the instant claims is that the instant claims require that R20 is a halogen and X is a counterion. However, it would have been prima facie obvious to one having ordinary skill in the art before the effective filing date of the instant application to modify the boronate ester of Hert into the claimed invention because boronate esters and organotrifluoroborates were both known organoboron reagents which were used in cross coupling reactions.
One would have been motivated because organotrifluoroborates where known in some instances to be superior to other organoboron reagents such as boronate esters. One would have modified the boronate ester of Hert into the claimed invention as a matter of optimizing the synthesis of formula (I).
One would have had a reasonable expectation of success because at the time organotrifluoroborates were a known alternative to boronate esters.
Allowable Subject Matter
Claims 1, 3, 5-6, 8, 10-11, 14, 17, 22, 24 and 35 are allowed.
Claims 12, 15 and 19 would be allowable if rewritten to overcome the rejection(s) under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), 2nd paragraph, set forth in this Office action and to include all of the limitations of the base claim and any intervening claims.
The following is an examiner’s statement of reasons for allowance:
The closest reference to the instant claims is Hert et al. (WO2017/037146 A1)(hereinafter “Hert”) which was discussed in the rejections herein. Hert is silent regarding variable R1 of the instant claims. There is no teaching which would have motivated one of ordinary skill in the art before the effective filing date of the instant application to modify Hert into the claimed invention with any reasonable expectation of success.
Any comments considered necessary by applicant must be submitted no later than the payment of the issue fee and, to avoid processing delays, should preferably accompany the issue fee. Such submissions should be clearly labeled “Comments on Statement of Reasons for Allowance.”
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to KEVIN MARTIN whose telephone number is (571)270-0917. The examiner can normally be reached Monday - Friday 8 am - 5 pm.
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July 9, 2026
/KEVIN S MARTIN/Examiner, Art Unit 1624
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