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 .
Status of the Application
Claims 1-11, 14 and 16-17 are pending in the application as of the preliminary amendment submitted 07/08/2024. Claims 12-13 and 15 are cancelled. Claims 1-11, 14 and 16-17 are examined herein.
In view of the pending claims, the following objections and rejections are made, as discussed below.
Priority
This application 371 of PCT/EP2022/064903 filed 06/01/2022, and claims foreign priority to UNITED KINGDOM 2107932.2 filed 06/03/2021.
Acknowledgment is made of applicant's claim for priority under 35 U.S.C. 119(a)-(d) or (f), 365(a) or (b), or 386(a) based upon an application filed in UNITED KINGDOM on 06/03/2021. Receipt is acknowledged of a certified copy of foreign application 2107932.2.
The subject matter of claims 1-11, 14 and 16-17 are supported by the foreign priority application and accordingly, have an effective filing date of 06/03/2021.
Information Disclosure Statement
The information disclosure statement submitted on 07/08/2024 is in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statement is being considered by the examiner.
Claim Objections
Claims 1-9, 11 and 16-17 are objected to because of the following informalities:
Replace all instances of “the formula” with “formula” for consistency of claim language.
Claim 1 - replace “the formula (14)” with “formula (14)”
Claim 2 - replace “the formula (14)” with “formula (14)”
Claim 3 - replace “the formula (13)” with “formula (13)”
Claim 4 - replace “the formula (12)” with “formula (12)”
Claim 5 - replace “the formula (18)” with “formula (18)” and “the formula (17)” with “formula (17)”
Claim 6 - replace “the formula (17)” with “formula (17)”
Claim 7 - replace “the formula (17)” with “formula (17)”
Claim 8 - replace “the formula (17)” with “formula (17)”, “the formula (15)” with “formula (15)” and “the formula (16)” with “formula (16)”
Claim 9, subsection e) - replace “the formula (17)” with “formula (17)”, “the formula (15)” with “formula (15)” and “the formula (16)” with “formula (16)”
Claim 11 - replace “the formula (14)” with “formula (14)”, “the formula (13)” with “formula (13)” and “the formula (12)” with “formula (12)”
Claim 16, subsection A) - replace “the formula (14)” with “formula (14)”
Claim 16, subsection B) - replace “the formula (14)” with “formula (14)”
Claim 16, subsection C) - replace “the formula (13)” with “formula (13)”
Claim 16, subsection D) - replace “the formula (12)” with “formula (12)”
Claim 16, subsection E) - replace “the formula (18)” with “formula (18)” and “the formula (17)” with “formula (17)”
Claim 17, subsection E) - replace “the formula (18)” with “formula (18)” and “the formula (17)” with “formula (17)”
In claim 11, it being an independent claim, the claim should read “A compound selected from
[[the]]a compound of [[the ]]formula (14): …;
[[the]]a compound of [[the ]]formula (13): …;
[[the]]a compound of [[the ]]formula (12): …”.
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 6-7, 9-10, 14 and 17 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.
Regarding claim 6, the claim recites “which process comprises reacting a compound of the formula (17) with an alkylsilyl halide (such as TMSI)”. The use of exemplary claim language “such as” and recitation of limitations in parentheses renders the claim indefinite because it is unclear whether the limitations following the phrase are part of the claimed invention. See MPEP 2173.05(d).
For the purpose of applying prior art, claim 6 has been interpreted to read “which process comprises reacting a compound of the formula (17) with an alkylsilyl halide” without the limitations in parentheses.
Regarding claim 7, the claim recites “which process comprises reacting a compound of the formula (17) with a sulphonic acid (such as benzene sulphonic acid)”. The use of exemplary claim language “such as” and recitation of limitations in parentheses renders the claim indefinite because it is unclear whether the limitations following the phrase are part of the claimed invention. See MPEP 2173.05(d).
For the purpose of applying prior art, claim 7 has been interpreted to read “which process comprises reacting a compound of the formula (17) with a sulphonic acid” without the limitations in parentheses.
Regarding claim 9, the claim recites “interconverting a product obtained from step i) into 5-[[5-[4-(4-fluoro-1-methyl-4-piperidyl)-2-methoxy-phenyl]-1H-pyrazol-3-yl]amino]pyrazine-2-carbonitrile, for example by reacting a compound of formula (18) with a methylating agent (such as HCHO in the presence of a reducing agent such as (AcO3)BH)”. The use of exemplary claim language “for example”, “such as” and recitation of limitations in parentheses renders the claim indefinite because it is unclear whether the limitations following the phrase are part of the claimed invention. See MPEP 2173.05(d).
For the purpose of applying prior art and correcting some antecedent basis issues, claim 9 has been interpreted to read “interconverting a product obtained from step i) into 5-[[5-[4-(4-fluoro-1-methyl-4-piperidyl)-2-methoxy-phenyl]-1H-pyrazol-3-yl]amino]pyrazine-2-carbonitrile, [[for example ]]by reacting[[ a]]the compound of formula (18) with a methylating agent” without the exemplary language “for example” and limitations in parentheses.
Regarding claim 10, the claim recites “interconverting a product obtained from step ii) into 5-[[5-[4-(4-fluoro-1-methyl-4-piperidyl)-2-methoxy-phenyl]-1H-pyrazol-3-yl]amino]pyrazine-2-carbonitrile, for example by reacting a compound of formula (18) with a methylating agent (such as HCHO in the presence of a reducing agent such as (AcO3)BH)”. The use of exemplary claim language “for example”, “such as” and recitation of limitations in parentheses renders the claim indefinite because it is unclear whether the limitations following the phrase are part of the claimed invention. See MPEP 2173.05(d).
For the purpose of applying prior art and correcting some antecedent basis issues, claim 10 has been interpreted to read “interconverting a product obtained from step ii) into 5-[[5-[4-(4-fluoro-1-methyl-4-piperidyl)-2-methoxy-phenyl]-1H-pyrazol-3-yl]amino]pyrazine-2-carbonitrile, [[for example ]]by reacting[[ a]]the compound of formula (18) with a methylating agent” without the exemplary language “for example” and limitations in parentheses.
Regarding claim 14, the claim recites “A compound according to claim 11 …”. There is insufficient antecedent basis for this limitation in the claim.
For the purpose of applying prior art, claim 14 has been interpreted to read ““[[A]]The compound according to claim 11 …” to provide sufficient antecedent basis to the limitation “A compound”.
Regarding claim 17, the claim depends from claim 9 and recites “which process comprises reacting a compound of the formula (17) with an alkylsilyl halide or a sulphonic acid, said process further comprising:
reacting a compound of the formula (17) with an alkylsilyl halide (such as TMSI); and/or
reacting a compound of the formula (17) with a sulphonic acid (such as benzene sulphonic acid)”.
The use of exemplary claim language “such as” and recitation of limitations in parentheses renders the claim indefinite because it is unclear whether the limitations following the phrase are part of the claimed invention. See MPEP 2173.05(d).
For the purpose of applying prior art and correcting some antecedent basis issues, claim 17 has been interpreted to read “a process for the preparation of the compound of[[ the]] formula (18): … which process comprises reacting[[ a]]the compound of[[ the ]]formula (17): … with an alkylsilyl halide or a sulphonic acid,[[ said process further comprising:
reacting a compound of the formula (17) with an alkylsilyl halide (such as TMSI); and/or
reacting a compound of the formula (17) with a sulphonic acid (such as benzene sulphonic acid)]]
wherein the alkylsilyl halide is TMSI and/or wherein the sulphonic acid is benzene sulphonic acid”.
Allowable Subject Matter
The intermediate compounds of instant claim 11 used in the process of preparation of 5-[[5-[4-(4-fluoro-1-methyl-4-piperidyl)-2-methoxy-phenyl]-1H-pyrazol-3-yl]amino]pyrazine-2-carbonitrile are novel and non-obvious. The process of instant claim 8 is free of prior art. Except for the claim objections and rejections discussed above, all claims would be allowable.
The closest prior art of record is Soltani et al. (WO 2021/119236 A1, filing date 10 December 2020, hereinafter Soltani, in the IDS) (Soltani qualifies as 35 U.S.C. 102(a)(2) prior art with different Applicant and inventive entity) and Boyle et al. (WO 2015/120390 A1, 13 August 2015, hereinafter Boyle, in the IDS).
Soltani teaches a synthetic route for the preparation of the CHK1 inhibitor compound shown below (Abstract).
PNG
media_image1.png
137
194
media_image1.png
Greyscale
The above compound is 5-[[5-[4-(4-fluoro-1-methyl-4-piperidyl)-2-methoxy-phenyl]-1H-pyrazol-3-yl]amino]pyrazine-2-carbonitrile, the same final product of the instant claims.
Soltani teaches the general Scheme 1 (Pg. 4, Lns. 1-6) and Scheme 2 (Pg. 11, Lns. 4-10) shown below for the preparation of 5-[[5-[4-(4-fluoro-1-methyl-4-piperidyl)-2-methoxy-phenyl]-1H-pyrazol-3-yl]amino]pyrazine-2-carbonitrile.
PNG
media_image2.png
502
798
media_image2.png
Greyscale
PNG
media_image3.png
354
702
media_image3.png
Greyscale
While Soltani uses the same final step of reductive alkylation as the instant claims to arrive at the final product, both schemes use different intermediates than the instant claims. The instant intermediates of formula (12), formula (13) and formula (14) are not taught in Soltani.
Boyle teaches Chk-1 kinase inhibitor compounds and methods of preparation of the same (Pg. 1, Lns. 1-5). Boyle teaches the exemplary compound of example 64 (Pg. 81, Table 1).
PNG
media_image4.png
170
341
media_image4.png
Greyscale
Example 64 of Boyle is 5-[[5-[4-(4-fluoro-1-methyl-4-piperidyl)-2-methoxy-phenyl]-1H-pyrazol-3-yl]amino]pyrazine-2-carbonitrile, the same final product of the instant claims.
Boyle teaches the synthetic route L with respect to the synthesis of the compound of example 64 (Pg. 154, Ln. 12 – Pg. 157, Ln. 19).
PNG
media_image5.png
310
742
media_image5.png
Greyscale
While Boyle uses the same final step of reductive alkylation as the instant claims to arrive at the final product, the synthetic route of Boyle uses different intermediates than the instant claims. The instant intermediates of formula (12), formula (13) and formula (14) are not taught in Boyle.
The instant specification teaches the process avoids the use of Dess-Martin periodinane as an oxidizing agent which is advantageous with respect to scale-up and cost effectiveness, that is used in the process of Scheme 2 of Soltani and method L of Boyle (Pg. 9, Lns. 24-28 of the instant specification). The instant specification teaches the process as an improvement by avoiding the production of genotoxic impurities (Pg. 6, Lns. 1-10 of instant specification).
Therefore, the instant process of preparation which depends from the novel intermediates in the preparation of 5-[[5-[4-(4-fluoro-1-methyl-4-piperidyl)-2-methoxy-phenyl]-1H-pyrazol-3-yl]amino]pyrazine-2-carbonitrile, is novel and non-obvious.
Conclusion
Claims 6-7, 9-10, 14 and 17 are rejected.
Claims 1-9, 11 and 16-17 are objected to.
No claims are allowed.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to PADMAJA S RAO whose telephone number is (571)272-9918. The examiner can normally be reached 9:00-5:30pm EDT.
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, Kortney L Klinkel can be reached on (571) 270-5239. 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.
/PADMAJA S RAO/Examiner, Art Unit 1627
Prosecution Insights