Prosecution Insights
Last updated: April 19, 2026
Application No. 17/926,763

SUBSTITUTED PYRAZINE COMPOUND, PHARMACEUTICAL COMPOSITION COMPRISING SAME, AND USE THEREOF

Final Rejection §103
Filed
Nov 21, 2022
Examiner
VISHNYAKOVA, ELENA VLADIMIROVNA
Art Unit
1691
Tech Center
1600 — Biotechnology & Organic Chemistry
Assignee
Sichuan Kelun-Biotech Biopharmaceutical Co. Ltd.
OA Round
2 (Final)
60%
Grant Probability
Moderate
3-4
OA Rounds
3y 0m
To Grant
99%
With Interview

Examiner Intelligence

Grants 60% of resolved cases
60%
Career Allow Rate
12 granted / 20 resolved
At TC average
Strong +73% interview lift
Without
With
+72.7%
Interview Lift
resolved cases with interview
Typical timeline
3y 0m
Avg Prosecution
32 currently pending
Career history
52
Total Applications
across all art units

Statute-Specific Performance

§101
0.8%
-39.2% vs TC avg
§103
42.6%
+2.6% vs TC avg
§102
17.2%
-22.8% vs TC avg
§112
18.4%
-21.6% vs TC avg
Black line = Tech Center average estimate • Based on career data from 20 resolved cases

Office Action

§103
DETAILED ACTION This office action is in response to applicant’s filing dated January 21, 2026. 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 Claims 1, 7, 14 - 18, 21, 25, 27, 29 and 30 are pending in the instant application. Receipt and consideration of Applicants' amended claim set and remarks/arguments filed on January 21, 2026 are acknowledged. Claims 21, 29 and 30 remain withdrawn, as being drawn to an unelected invention or specie. Acknowledgement is made of Applicant's amendment of claims 1, 7 and 14 - 16; and cancelation of claims 2 – 6, 8-13, 23-24, 26, and 28. Claims under consideration in the instant office action are claims 1, 7, 14 – 18, 25 and 27. Objections and/or Rejections and Response to Arguments Applicants' arguments, filed on January 21, 2026, have been fully considered. Acknowledgement is made of the Applicant’s cancellation of claims 2 - 6, 9 and 10. Accordingly, the rejection of claims 2 - 6, 9 and 10 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second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter is withdrawn. Rejections and/or objections not reiterated from previous office actions are hereby withdrawn. The following rejections and/or objections are either reiterated (Maintained Objections and/or Rejections) or newly applied (New Objections and/or Rejections, Necessitated by Amendment or New Objections and/or Rejections, NOT Necessitated by Amendment). They constitute the complete set presently being applied to the instant application. 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 (i.e., changing from AIA to pre-AIA ) 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, 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. 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. Claims 1, 7, 14 – 18, 25 and 27 are rejected under 35 U.S.C. 103 as being unpatentable over Koltun et al (WO 2018/013597 A1, cited in IDS, filed 11/21/2022, hereinafter Koltun) in view of Liu et al (US 2021/0355105 A1, with priority date October 10, 2019, hereinafter Liu). Instant claims are drawn to a compound of formula I: PNG media_image1.png 113 205 media_image1.png Greyscale , such as compound of formula: PNG media_image2.png 110 195 media_image2.png Greyscale where ring A is pyridinylene substituted by F or Cl, B is PNG media_image3.png 32 93 media_image3.png Greyscale , where C is pyrrolidylidene or azetidinylene optionally substituted by F, Cl, -Me, -CH2F; Y is -CH2- or -C(=O)-CH2-; Rd is F, -NH2, -OH, -CN, such as B is PNG media_image4.png 61 16 media_image4.png Greyscale , PNG media_image5.png 57 75 media_image5.png Greyscale , PNG media_image6.png 64 87 media_image6.png Greyscale or PNG media_image7.png 51 67 media_image7.png Greyscale ; and PNG media_image8.png 74 93 media_image8.png Greyscale is PNG media_image9.png 60 1 media_image9.png Greyscale , PNG media_image9.png 60 1 media_image9.png Greyscale or PNG media_image10.png 67 61 media_image10.png Greyscale e.g. compounds: 12, PNG media_image11.png 196 140 media_image11.png Greyscale , 67 PNG media_image12.png 243 187 media_image12.png Greyscale , or 73 PNG media_image13.png 212 183 media_image13.png Greyscale , where the compounds or the pharmaceutically acceptable salts stereoisomers, tautomers act as SHP2 inhibitors. The instant claims are further drawn to a pharmaceutical composition comprising compound of formula I and a pharmaceutically acceptable carrier, and a drug comprising a compound of formula I held in the container. Koltun teaches compounds of formula I-W: PNG media_image14.png 169 268 media_image14.png Greyscale (page 179, [0322]) such as compound A-283 PNG media_image15.png 77 44 media_image15.png Greyscale (page 128, Table). The difference in structure between compounds A-283 of Koltun and instantly claimed compound 12 is methyl group in pyrazine ring and -CH2- group in fragment: PNG media_image15.png 77 44 media_image15.png Greyscale (compound of Koltun) or PNG media_image4.png 61 16 media_image4.png Greyscale (instant compounds). The compounds of Koltun act as SHP2 inhibitors (abstract). Koltun further teaches pharmaceutical compositions comprising one or more compounds of formula I-W or pharmaceutically acceptable salts, prodrugs, solvates, hydrates, tautomers, or isomers thereof, and a pharmaceutically acceptable carrier (page 22, [0018]). In addition Koltun teaches pharmaceutical package or kit comprising one or more containers filled with at least one compound of formula I-W (page 149, [0239]). Koltun does not teach where R2 is hydrogen and group B is PNG media_image4.png 61 16 media_image4.png Greyscale , PNG media_image5.png 57 75 media_image5.png Greyscale or PNG media_image6.png 64 87 media_image6.png Greyscale and group PNG media_image8.png 74 93 media_image8.png Greyscale is PNG media_image9.png 60 1 media_image9.png Greyscale or PNG media_image10.png 67 61 media_image10.png Greyscale . However, Liu teaches compounds, acting as SHP2 inhibitors (abstract) and having structure according to formula VIII: PNG media_image16.png 23 4 media_image16.png Greyscale , where L2 is sulfur (page 5, [0100]), ring A is 5 to 12 membered heteroaryl (page 5, [0101]) (e.g. pyridyl (page 36, [0235]); R1 is C1-6 alkyl further substituted by hydroxy (page 5, [0102]); R2 is halogen or 3 to 12 membered heterocyclyl further substituted with C1-6 hydroxyalkyl (where alkyl is methyl or isopropyl (page 32, [0219])) and x is an integer of 2 (page 6, [0103]); R3 is hydrogen (page 6, [0104]); R5 is hydrogen or C1-6 alkyl (page 6, [0105]); R8 and R9 are bonded to form a 3 to 12 membered heterocyclyl, wherein 3 to 12 membered heterocyclyl is optionally further substituted by one or more substituent(s) selected from hydrogen, amino or C1-6 alkyl (page 6, [0107]). For example, fragment PNG media_image16.png 23 4 media_image16.png Greyscale is PNG media_image17.png 95 131 media_image17.png Greyscale , (page 60, [0597]). Thus, compound of formula VIII is equivalent to a compound 67 of instant claims if: L2 is sulfur; Ring A is pyridyl; R1 is C1 alkyl (methyl) further substituted by hydroxy; R2 are Cl (halogen) and azetidinyl (4 membered heterocyclyl) further substituted with 2-hydroxyisopropyl (C3 hydroxyalkyl) and x is an integer of 2; R3 and R5 is hydrogen, and fragment PNG media_image16.png 23 4 media_image16.png Greyscale is PNG media_image17.png 95 131 media_image17.png Greyscale . The compound of formula VIII is equivalent to a compound 12 of instant claims if: L2 is sulfur; Ring A is pyridyl; R1 is C1 alkyl (methyl) further substituted by hydroxy; R2 are Cl (halogen) and azetidinyl (4 membered heterocyclyl) further substituted with hydroxymethyl (C1 hydroxyalkyl) and x is an integer of 2; R3 and R5 is hydrogen, and fragment PNG media_image16.png 23 4 media_image16.png Greyscale is PNG media_image17.png 95 131 media_image17.png Greyscale , . Liu further teaches compounds of formula IX PNG media_image18.png 156 338 media_image18.png Greyscale (page 6, [0111]), where M is nitrogen, L2 is sulfur, R1 is C1-6 hydroxyalkyl, R5 is hydrogen or C1-6 alkyl, R12 is halogen and R13 is 3 to 12 membered heterocyclyl (such as pyrrolidinyl or azetidinyl) further substituted with halogen, amino, cyano, C1-6 hydroxyalkyl (where alkyl is methyl or isopropyl) (page 6, [0121]), and fragment PNG media_image19.png 98 163 media_image19.png Greyscale is PNG media_image20.png 121 134 media_image20.png Greyscale (Page 61, [0609]), such as compound of formula XII-A: PNG media_image21.png 160 304 media_image21.png Greyscale The compound of formula XII-A is equivalent to a compound of formula 73 of instant claims if: R1 is hydroxymethyl (C1 hydroxyalkyl); R5 is hydrogen; R12 is Cl (halogen); R13 is azetidinyl (4 membered heterocyclyl) further substituted with 2-hydroxyisopropyl (C3 hydroxyalkyl), and fragment PNG media_image19.png 98 163 media_image19.png Greyscale is PNG media_image20.png 121 134 media_image20.png Greyscale . Thus, since prior art teaches compounds, inhibiting SHP2, and having the same core structure and substituents as claimed compounds, it would have been prima facie obvious to one of ordinary skill in the art before the effective filing date of the present invention to combine teachings of prior art and make various compounds acting as SHP2 inhibitors, to arrive at claimed compounds. The one of ordinary skills would be motivated to do so in search of an active agent capable to inhibit SHP2, with improved desired properties with the reasonable expectation of success. Therefore, taking all together, taught by prior art, the invention as a whole is prima facie obvious to one of ordinary skill in the art at the time the invention was made, as evidenced by the references, especially in the absence of evidence to the contrary. Response to Arguments Applicant argues: after an amendment of claim 1 the compound of formula I has a structure: PNG media_image22.png 110 307 media_image22.png Greyscale , where: PNG media_image23.png 537 634 media_image23.png Greyscale . Compounds taught by Koltun do not have a methylene (Compound 12) or isopropylene group (Compound 67 or 73, etc.) between azetidinyl and hydroxyl groups; There are other alternatives of fragment PNG media_image8.png 74 93 media_image8.png Greyscale , e.g. PNG media_image9.png 60 1 media_image9.png Greyscale , which Koltun does not teach; Liu teaches compounds of formula IX: PNG media_image18.png 156 338 media_image18.png Greyscale , however specific compounds of Liu have -CH2-OH as R1 and R5 is methyl; although some compounds of Liu could be regarded as the compounds of close structure to present application, it still lacks the fragment PNG media_image3.png 32 93 media_image3.png Greyscale , as recited by amended claim 1; the results in Experimental Examples 1-11 of the present application demonstrate advanced pharmacological properties of instantly claimed compounds compared to control compound 1, control compound 2, or TNO-155 ( PNG media_image24.png 165 373 media_image24.png Greyscale ). Examiner’s response: Applicant's arguments have been fully considered but they are not persuasive because: as set forth above in the rejection section, Koltun and Liu teach compounds, which compounds have all the structural features and the same practicality as instantly claimed compounds. Although Koltun does not disclose some of the structural elements required by instant claims, however, compounds of Liu such as compound of formula XII-A: PNG media_image21.png 160 304 media_image21.png Greyscale , where R1 is -CH2-OH, R5 is hydrogen, R12 is halogen and R13 is pyrrolidinyl or azetidinyl further substituted with halogen, amino, cyano, C1-6 hydroxyalkyl (where alkyl is methyl or isopropyl) and where variable R13 corresponds to the fragment PNG media_image3.png 32 93 media_image3.png Greyscale of instant claims, have all the structural elements of the compounds of formula I of instant claims. Moreover, Liu teaches fragment PNG media_image16.png 23 4 media_image16.png Greyscale alternatively having a structure: PNG media_image17.png 95 131 media_image17.png Greyscale or PNG media_image25.png 94 115 media_image25.png Greyscale (page 26, ex. 154). Regarding the arguments that exemplary compounds of Liu have methyl group as R5 variable, it is not persuasive, because Liu still teaches R5 to be a hydrogen (see the rejection section). MPEP 2123 states: "The use of patents as references is not limited to what the patentees describe as their own inventions or to the problems with which they are concerned. They are part of the literature of the art, relevant for all they contain." In re Heck, 699 F.2d 1331, 1332-33, 216 USPQ 1038, 1039 (Fed. Cir. 1983) (quoting In re Lemelson, 397 F.2d 1006, 1009, 158 USPQ 275, 277 (CCPA 1968)). Furthermore, "[t]he prior art’s mere disclosure of more than one alternative does not constitute a teaching away from any of these alternatives because such disclosure does not criticize, discredit, or otherwise discourage the solution claimed…." In re Fulton, 391 F.3d 1195, 1201, 73 USPQ2d 1141, 1146 (Fed. Cir. 2004). Thus, since teachings of Liu describe variable R5 as a hydrogen, which is relevant to the compounds of instant claims, they constitute a prior art regardless that exemplary compounds have a methyl in the R5 position. Regarding the argument about pharmacological activities of instantly clamed compounds, it is not persuasive, because, since Liu teaches compounds of the same structure, all the properties of such compounds are inherently present. MPEP 2112.01 states: "Products of identical chemical composition cannot have mutually exclusive properties." In re Spada, 911 F.2d 705, 709, 15 USPQ2d 1655, 1658 (Fed. Cir. 1990). A chemical composition and its properties are inseparable. Therefore, if the prior art teaches the identical chemical structure, the properties applicant discloses and/or claims are necessarily present. Id. (Applicant argued that the claimed composition was a pressure sensitive adhesive containing a tacky polymer while the product of the reference was hard and abrasion resistant. "The Board correctly found that the virtual identity of monomers and procedures sufficed to support a prima facie case of unpatentability of Spada’s polymer latexes for lack of novelty."). Thus, since prior art teaches compounds where all the structural features are relevant to those of instantly claimed compounds, the compounds of instant invention are considered to be obvious variants of compounds taught by prior art. Therefore, Applicant’s arguments are not persuasive, and the rejection of claims 1, 7, 14 – 18, 25 and 27 as obvious over teachings of Koltun and Liu is maintained. Conclusion Claims 1, 7, 14 – 18, 25 and 27 are rejected. No claim is allowed. Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a). A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action. Any inquiry concerning this communication or earlier communications from the examiner should be directed to ELENA V VISHNYAKOVA whose telephone number is (571)272-3781. The examiner can normally be reached 7:30am - 5pm ET. 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, RENEE CLAYTOR can be reached at (571)272-8394. 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. /E.V.V./Examiner, Art Unit 1691 /SAVITHA M RAO/Primary Examiner, Art Unit 1691
Read full office action

Prosecution Timeline

Nov 21, 2022
Application Filed
Oct 17, 2025
Non-Final Rejection — §103
Jan 21, 2026
Response Filed
Mar 10, 2026
Final Rejection — §103 (current)

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Prosecution Projections

3-4
Expected OA Rounds
60%
Grant Probability
99%
With Interview (+72.7%)
3y 0m
Median Time to Grant
Moderate
PTA Risk
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