Prosecution Insights
Last updated: April 19, 2026
Application No. 18/114,979

AMINO ACID COMPOUNDS AND METHODS OF USE

Non-Final OA §DP
Filed
Feb 27, 2023
Examiner
REILLY, SOPHIA JANE
Art Unit
1627
Tech Center
1600 — Biotechnology & Organic Chemistry
Assignee
Pliant Therapeutics Inc.
OA Round
1 (Non-Final)
57%
Grant Probability
Moderate
1-2
OA Rounds
3y 6m
To Grant
99%
With Interview

Examiner Intelligence

Grants 57% of resolved cases
57%
Career Allow Rate
31 granted / 54 resolved
-2.6% vs TC avg
Strong +51% interview lift
Without
With
+51.1%
Interview Lift
resolved cases with interview
Typical timeline
3y 6m
Avg Prosecution
36 currently pending
Career history
90
Total Applications
across all art units

Statute-Specific Performance

§101
2.7%
-37.3% vs TC avg
§103
33.2%
-6.8% vs TC avg
§102
15.4%
-24.6% vs TC avg
§112
26.1%
-13.9% vs TC avg
Black line = Tech Center average estimate • Based on career data from 54 resolved cases

Office Action

§DP
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 . Priority The instant application is a CON of 16/894,712 filed June 5, 2020 and 16/471,521 filed June 19, 2019, a 371 National Stage Entry of PCT/PCT/US2017/067622 filed on December 20, 2017 which claims benefit to domestic application Nos. 62/538,564 filed on July 28, 2017 and 62/438,951 filed December 23, 2016. Status of Claims Acknowledgement is made of cancelled (1-33) and new (34-42) claims filed on June 23, 2023. Claims 34-42 are pending in instant application. Information Disclosure Statement The information disclosure statement filed on June 23, 2023 has been considered except where lined through. Specification The title of the invention is not descriptive. A new title is required that is clearly indicative of the invention to which the claims are directed. The following title is suggested: NAPHTHYRIDINYL COMPOUNDS FOR TREATING FIBROTIC DISEASES. Double Patenting The nonstatutory double patenting rejection is based on a judicially created doctrine grounded in public policy (a policy reflected in the statute) so as to prevent the unjustified or improper timewise extension of the “right to exclude” granted by a patent and to prevent possible harassment by multiple assignees. A nonstatutory double patenting rejection is appropriate where the conflicting claims are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg, 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); In re Goodman, 11 F.3d 1046, 29 USPQ2d 2010 (Fed. Cir. 1993); In re Longi, 759 F.2d 887, 225 USPQ 645 (Fed. Cir. 1985); In re Van Ornum, 686 F.2d 937, 214 USPQ 761 (CCPA 1982); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); In re Thorington, 418 F.2d 528, 163 USPQ 644 (CCPA 1969). A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) or 1.321(d) may be used to overcome an actual or provisional rejection based on nonstatutory double patenting provided the reference application or patent either is shown to be commonly owned with the examined application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. See MPEP § 717.02 for applications subject to examination under the first inventor to file provisions of the AIA as explained in MPEP § 2159. See MPEP § 2146 et seq. for applications not subject to examination under the first inventor to file provisions of the AIA . A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b). The filing of a terminal disclaimer by itself is not a complete reply to a nonstatutory double patenting (NSDP) rejection. A complete reply requires that the terminal disclaimer be accompanied by a reply requesting reconsideration of the prior Office action. Even where the NSDP rejection is provisional the reply must be complete. See MPEP § 804, subsection I.B.1. For a reply to a non-final Office action, see 37 CFR 1.111(a). For a reply to final Office action, see 37 CFR 1.113(c). A request for reconsideration while not provided for in 37 CFR 1.113(c) may be filed after final for consideration. See MPEP §§ 706.07(e) and 714.13. The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The actual filing date of the application in which the form is filed determines what form (e.g., PTO/SB/25, PTO/SB/26, PTO/AIA /25, or PTO/AIA /26) should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission. For more information about eTerminal Disclaimers, refer to www.uspto.gov/patents/apply/applying-online/eterminal-disclaimer. Claims 34, 36-37 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 59, 62, 64-68, 78-79, 86, of copending Application No. 18/140,5201 (reference application). Although the claims at issue are not identical, they are not patentably distinct from each other. Regarding instant claims 34, 36-37 and treating a fibrotic disease with a claimed compound, App’520 claims a method of treating a fibrotic disease (including instant pulmonary fibrosis, liver fibrosis, skin fibrosis, cardiac fibrosis, kidney fibrosis, gastrointestinal fibrosis, primary sclerosing cholangitis, and biliary fibrosis) in an individual comprising administering a compound of Formula I (App’520 claim 59), including compound 28 (+/-)-2-(2,6-dichlorobenzamido)-3-(3-(3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propoxy)azetidin-1-yl)propanoic acid (see App’520 claim 86 and spec. at p. 73 for structure), structurally similar to instant compound (S)-2-(2,6-dichlorobenzamido)-4-(3-(2-(5,6,7, 8-tetrahydro-1, 8-naphthyridin-2- yl)ethoxy)azetidin-1-yl)butanoic acid, CAS# 2231182-04-8. App’520 Formula I corresponds to instantly claimed compounds. For example, instant compound CAS# 2231182-04-8 corresponds to App’520 Formula I when R1 is C6-14 aryl specifically phenyl substituted by R10 and R10 is R9 and R9 is halogen specifically chlorine (see also App’520 claims 62), R2 is a 3 to 12 membered heterocyclyl containing at least 2 nitrogen atoms specifically PNG media_image1.png 87 110 media_image1.png Greyscale (see also App’520 claim 78-79) and A-L is A1-L1 (see also App’520 claim 64), A1 is 3-12 membered heterocyclclylene, specifically azetidinylene PNG media_image2.png 45 54 media_image2.png Greyscale (see also App’520 claim 65), L1 is O-(CH2)3 (see also App’520 claims 66-68). App’520 Claim 59 Formula I PNG media_image3.png 82 167 media_image3.png Greyscale App’520 Claim 86 Compound 28 Instant Claim 34 CAS# 2231182-04-8 PNG media_image4.png 172 374 media_image4.png Greyscale PNG media_image5.png 116 135 media_image5.png Greyscale App’520 claims treating specific fibrotic diseases (App’520 claim 59). The copending claims differ as follows: instant CAS# 2231182-04-8 differs from App’520 compound 28 by a difference of -(CH2)-. However, Regarding a change of -(CH2)-, per MPEP § 2144.09(I)-(II), “[a] prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities” because compounds which are homologs, compounds differing e.g. by -CH2- groups, are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties (see, e.g., MPEP § 2144.09(I)-(II)). Therefore it would have been obvious to one skilled in the art to arrive at the instant invention based on the genus and similar species claimed by App’520 with a reasonable expectation of success because the compounds are structurally similar (differ only by -CH2-) and have the same utility (treating fibrotic disease). This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented. Claims 34-42 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1 - 34 of re-issue patent RE050554, corresponding to Application No. 18/211,0222. The Examiner notes that an NSDP rejection over US 10,696,672 was not included due to it’s re-issue. Although the claims at issue are not identical, they are not patentably distinct from each other. Regarding instant claim 34 and a compound, App’022 claims exact compounds also instantly claimed (compare App’022 claim 27 with instant claim 34) (see e.g., (S)-2-benzamido-4-((R)-3-fluoro-3-(2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethyl)piperidin-1-yl)butanoic acid, CAS# 2231178-27-9). App’022 also generically claims a genus that encompasses instant compounds (see App’022 claims 1-26). For example, instantly claimed CAS# 2231178-27-9 reads on App’022 Formula I when n is 2, q and p are 0, X is C1-C3 alkylene specifically ethylene, R1 is C6-14 aryl specifically phenyl, m is 1 and R5 is halogen specifically fluorine. App’022 Claim 1 Formula I App’022 Claim 27 and Instant Application Claim 34 Exemplary Compound CAS# 2231178-27-9 PNG media_image6.png 91 242 media_image6.png Greyscale PNG media_image7.png 224 231 media_image7.png Greyscale Regarding instant claim 35 and a pharmaceutical composition, App’022 claims a pharmaceutical composition comprising a compound of Formula I (App’022 claim 28). Regarding instant claims 36-37 methods of treating fibrotic disease, App’022 claims methods of treating fibrotic diseases including those specifically claimed comprising administering compounds of Formula I (App’022 claims 29-30). Regarding instant claims 38-40 and a kit, App’022 claims kits comprising compounds of Formula I and instructions for treatment of fibrotic diseases (App’022 claims 31-32). Regarding instant claims 41-42 and methods of inhibiting αvβ6 or TGFβ, App’022 claims methods of inhibiting αvβ6 or TGFβ (App’022 claims 33-34). Claim 34-42 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-41 of U.S. Patent No. US 11,634,418 B23. Although the claims at issue are not identical, they are not patentably distinct from each other. Regarding instant claim 34 and a compound, US’418 claims exact compounds also instantly claimed (compare US’418 claim 30 with instant claim 34) (see e.g., (S)-2-benzamido-4-((R)-3-fluoro-3-(2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethyl)piperidin-1-yl)butanoic acid, CAS# 2231178-27-9). US’418 also generically claims a genus that encompasses instant compounds (see US’418 claims 1-29). For example, instantly claimed CAS# 2231178-27-9 reads on US’418 Formula I-A when n is 2, q and p are 0, X is C1-C3 alkylene specifically ethylene, R1 is C6-14 aryl specifically phenyl, m is 1 and R5 is halogen specifically fluorine, and ---- is absent. US’418 Claim 1 Formula I-A App’022 Claim 30 and Instant Application Claim 34 Exemplary Compound CAS# 2231178-27-9 PNG media_image8.png 101 289 media_image8.png Greyscale PNG media_image7.png 224 231 media_image7.png Greyscale Other exemplary compounds claimed include (S)-2-benzamido-4-((R)-3-((5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)methoxy)pyrrolidin-1yl)butanoic acid (compare US’418 claim 32 with instant claim 27), (S)-2-(4,4-difluorocyclohexane-1-carboxamido)-4-(4-(((5,6,7, 8-tetrahydro-1,8- naphthyridin-2-yl)methyl)amino)piperidin-1-yl)butanoic acid (compare US’418 claim 33 with instant claim 27), and (S)-2-(3-fluoro-5-(trifluoromethyl)benzamido)-4-((1 R,2R,4S)-2-(2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethyl)-7-azabicyclo[2.2.1]heptan-7-yl)butanoic acid (compare US’418 claim 34 with instant claim 34). US’418 Claim 32 and Instant Application Claim 34 US’418 Claim 33 and Instant Application Claim 34 PNG media_image9.png 110 282 media_image9.png Greyscale PNG media_image10.png 123 288 media_image10.png Greyscale US’418 Claim 34 Instant Application Claim 34 PNG media_image11.png 119 283 media_image11.png Greyscale Regarding instant claim 35 and a pharmaceutical composition, US’418 claims a pharmaceutical composition comprising a compound of Formula I-A (US’418 claim 35). Regarding instant claims 36-37 methods of treating fibrotic disease, US’418 claims methods of treating fibrotic diseases including those specifically claimed comprising administering compounds of Formula -AI (US’418 claims 38-39). Regarding instant claims 38-40 and a kit, US’418 claims kits comprising compounds of Formula I-A and instructions for treating fibrotic disease (US’418 claims 36-37). Regarding instant claims 41-42 and methods of inhibiting αvβ6 or TGFβ, US’418 claims methods of inhibiting αvβ6 or TGFβ (US’418 claims 40-41). Conclusion The title is objected to. Claims 34-42 are rejected. Any inquiry concerning this communication or earlier communications from the examiner should be directed to SOPHIA J REILLY whose telephone number is (703)756-5669. The examiner can normally be reached 9:00 am - 5:00 pm EST M-F. 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 KLINKEL can be reached at 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. /S.R./Examiner, Art Unit 1627 /JENNIFER A BERRIOS/ Primary Examiner, Art Unit 1613 1 CON of 16/809,244 filed March 4, 2020, CON of 15/698,435 filed September 7, 2017, PRO 62/384,682 filed September 7, 2016. Hereinafter App’520. 2 REI of 16/471,521 filed June 19, 2019, a 371 of PCT/US2017/067622 filed December 20, 2017. Hereinafter App’022. 3 Filed June 5, 2020 and patented April 25, 2023. Hereinafter US’418.
Read full office action

Prosecution Timeline

Feb 27, 2023
Application Filed
Sep 11, 2025
Non-Final Rejection — §DP (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
57%
Grant Probability
99%
With Interview (+51.1%)
3y 6m
Median Time to Grant
Low
PTA Risk
Based on 54 resolved cases by this examiner. Grant probability derived from career allow rate.

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