Prosecution Insights
Last updated: April 19, 2026
Application No. 18/018,884

PYRAZINE COMPOUND, AND METHOD OF PREPARATION AND USE THEREOF

Non-Final OA §102§103§112
Filed
May 04, 2023
Examiner
HAVLIN, ROBERT H
Art Unit
1626
Tech Center
1600 — Biotechnology & Organic Chemistry
Assignee
Shenzhen Olive Biopharmaceuticals Co. Ltd.
OA Round
1 (Non-Final)
53%
Grant Probability
Moderate
1-2
OA Rounds
2y 11m
To Grant
80%
With Interview

Examiner Intelligence

Grants 53% of resolved cases
53%
Career Allow Rate
534 granted / 1016 resolved
-7.4% vs TC avg
Strong +27% interview lift
Without
With
+27.2%
Interview Lift
resolved cases with interview
Typical timeline
2y 11m
Avg Prosecution
99 currently pending
Career history
1115
Total Applications
across all art units

Statute-Specific Performance

§101
1.0%
-39.0% vs TC avg
§103
30.8%
-9.2% vs TC avg
§102
24.8%
-15.2% vs TC avg
§112
28.2%
-11.8% vs TC avg
Black line = Tech Center average estimate • Based on career data from 1016 resolved cases

Office Action

§102 §103 §112
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 . Priority This application is a 371 of PCT/CN2021/109564 (07/30/2021), and claims foreign priority to CHINA 202010759402.5 (07/31/2020), and CHINA 202010759405.9 (07/31/2020). 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 1-21 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 1 has the language: PNG media_image1.png 29 701 media_image1.png Greyscale PNG media_image2.png 24 69 media_image2.png Greyscale which is unclear as to whether all of the recited forms are required in the product claim. One of skill in the art would find the language confusing because the “and” implies that all must be present, however, dependent claims and the specification do not make this clear. Claims 2-8, 13, 15-21 share the indefiniteness for the same reason, thus claims 1-8, 13, 15-21 are rejected. For purposes of examination, the claim is interpreted as though the “and” is replaced with “or”. Claim 1 uses the phrase “derivative thereof” which is not defined in the specification and does not have a single clear accepted meaning in the art. Use of the term “derivative” would be ambiguous and confusing to one of skill in the art due to the term’s vague meaning. In addition, “The Dictionary of Chemistry,” 2nd edition, McGraw Hill, 2003, page 105, defines the term as follows: PNG media_image3.png 24 665 media_image3.png Greyscale Based on the available definition, one of skill in the art would not be apprised of the scope of what is and what is not a “derivative” in the claim. For example, the claim is ambiguous as to whether metabolites are included in the scope or whether the scope is only to deuterium substitutions. Claims 2-8, 13, 15-21 share the indefiniteness for the same reason, thus claims 1-8, 13, 15-21 are rejected. Claim 2 uses the term “substituted” and the specification does not provide a clear definition of what is intended within the scope. Use of the term “substituted” would be ambiguous and confusing to one of skill in the art due to the term’s vague meaning and lack of guidance as to whether the term was structurally limiting. Thus, the claim is indefinite. Claims 9-10 are to a “method of preparation of a compound, comprising the following steps” but does not recite any steps and instead uses figures and diagrams without any associated description or reference to particular steps. Claims 11-12 are to compounds with a structure that is not described in the claims or specification, for example “O-Protecting group” and “OTBS”. One of skill in the art would thus find the claim ambiguous as to what the structure of the compound is. Thus the claims are indefinite as is claim 14 depending therefrom and incorporating the indefiniteness. Claim 19 refers to “The use according to claim 18” which lacks an antecedent basis. Claim Rejections - 35 USC § 102 The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action: A person shall be entitled to a patent unless – (a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention. (a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention. Claims 1-5 are rejected under 35 U.S.C. 102(a)(1) as being anticipted by Liu et al. (Chinese Journal of Pharmaceutical Chemistry, Vol. 17, No. 5, pp. 283-287, 313; cited in IDS 1/18/24). Liu teaches compound 1g in Table 1: PNG media_image4.png 92 156 media_image4.png Greyscale PNG media_image5.png 208 319 media_image5.png Greyscale Which anticipates claim 1 when: R1-3 are Me (alkyl); R4 is H; X and Y are O; n and m are 1. Claims 2-5 also read on Liu’s compound 1g. Thus, the claims are anticipated. 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 1-7 are rejected under 35 U.S.C. 103 as being unpatentable over Liu et al. (Chinese Journal of Pharmaceutical Chemistry, Vol. 17, No. 5, pp. 283-287, 313; cited in IDS 1/18/24). Liu teaches pharmaceutical optimization of structures of liqustrazine derivatives by varying the structure of the “R” group of the TMP structure showin in Table 1 (Abstract, p. 283-284). Liu teaches as in the 35 USC 102 rejection of claims 1-5 supra and incorporated herein. Liu also renders these claims obvious. Regarding claims 6-7, Liu does not specifically teach the structures recited in, for example claim 7 where there is a 4-hydroxyl substituent on the phenyl ring. However, Liu does teach compound 1g (phenyl) and identifies 1c (comprising a 4-hydroxyphenyl) and compound 1l (4-methoxyphenyl) as highly active. One of ordinary skill in the art following the teaching of Liu would have had a reasonable expectation of success in modifying compound 1g with a 4-hydroxyl substituent and arrive at the claimed invention. One of ordinary skill in the art would have had a reasonable expectation of success in view of Liu’s teaching of the closely structurally related compound also showing high levels of activity as well as Liu’s models predicting activity (p. 285-287). Therefore, the claims are prima facie obvious. Regarding claims 13, 15-17 to a pharmaceutical composition and claims 18-21, Liu teaches the compounds are pharmaceuticals useful in cardiovascular and cerebrovascular disease (p. 283) such that one of ordinary skill in the art would have considered formulating the resulting compound as a pharmaceutical composition and administering it to treat the corresponding diseases and arrive at the claimed invention. With each of the claims, the level of skill in the art is very high such that one of ordinary skill in the art would consider routine the combination of elements from the teaching of the art. One of ordinary skill in the art would have recognized that the results of the combination would be predictable due to the well-known nature and optimizations routinely performed in the art. Thus, one of ordinary skill in the art would have arrived at the invention as claimed with a reasonable expectation of success. Conclusion No claims allowed. Any inquiry concerning this communication or earlier communications from the examiner should be directed to ROBERT H HAVLIN whose telephone number is (571)272-9066. The examiner can normally be reached 9am - 6pm. 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, Joseph McKane can be reached at 571-272-0699. 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. /ROBERT H HAVLIN/Primary Patent Examiner, Art Unit 1626
Read full office action

Prosecution Timeline

May 04, 2023
Application Filed
Sep 11, 2025
Non-Final Rejection — §102, §103, §112 (current)

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Study what changed to get past this examiner. Based on 5 most recent grants.

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Prosecution Projections

1-2
Expected OA Rounds
53%
Grant Probability
80%
With Interview (+27.2%)
2y 11m
Median Time to Grant
Low
PTA Risk
Based on 1016 resolved cases by this examiner. Grant probability derived from career allow rate.

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