Prosecution Insights
Last updated: April 19, 2026
Application No. 18/250,012

PYRROLIDINE-3-CARBOXAMIDE DERIVATIVES AND RELATED USES

Non-Final OA §102§103§112
Filed
Apr 21, 2023
Examiner
MCANANY, JOHN D
Art Unit
1625
Tech Center
1600 — Biotechnology & Organic Chemistry
Assignee
Chulalongkorn University
OA Round
1 (Non-Final)
67%
Grant Probability
Favorable
1-2
OA Rounds
3y 2m
To Grant
99%
With Interview

Examiner Intelligence

Grants 67% — above average
67%
Career Allow Rate
33 granted / 49 resolved
+7.3% vs TC avg
Strong +51% interview lift
Without
With
+51.0%
Interview Lift
resolved cases with interview
Typical timeline
3y 2m
Avg Prosecution
39 currently pending
Career history
88
Total Applications
across all art units

Statute-Specific Performance

§101
0.7%
-39.3% vs TC avg
§103
30.6%
-9.4% vs TC avg
§102
21.8%
-18.2% vs TC avg
§112
30.3%
-9.7% vs TC avg
Black line = Tech Center average estimate • Based on career data from 49 resolved cases

Office Action

§102 §103 §112
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 . 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. Current Status of 18/250,012 This Office Action is responsive to the election received 23 December 2025. Claims 1-8, 10-15, 21, 23-24, 26, 28, and 32 are currently pending. Election/Restrictions Applicant’s election without traverse of compound 149 (shown below and found on page 150 of the instant specification), in the reply filed on 23 December 2025, is acknowledged. PNG media_image1.png 262 405 media_image1.png Greyscale The elected species has been determined to read on claims 1-5, 7-8, 10, 12-13, 21, 23-24, 26, 28, and 32. Claims 6, 11, and 14-15 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention, there being no allowable generic or linking claim. A search for Applicant’s elected species did not retrieve applicable prior art or double patent art. The search was expanded until the references below, which are the basis for the rejections herein, were found. MPEP 803.02; Ex parte Ohsaka, 2 USPQ2d 1460, 1461 (Bd. Pat. App. lnt. 1987). Priority Applicant’s claim for the benefit of the prior-filed patent applications PCT/US2021/056267 (filed 22 October 2021), 63/194,497 (filed 28 May 2021), and 63/104,103 (filed 22 October 2020) under 35 U.S.C. 119(e), 120, 121, 365(c), or 386(c) is acknowledged. Information Disclosure Statement As of 13 February 2026, Applicant has not filed an Information Disclosure Statement. Claim Objections Claim 2 is objected to because of the following informalities: There appears to be a typographical error in the phrase “Ring A is substituted by at least on RA”. Applicant may choose to amend the quoted phrase as follows “Ring A is substituted by at least one RA”. Appropriate correction is required. Claim Rejections - 35 USC § 112 The following is a quotation of the first paragraph of 35 U.S.C. 112(a): (a) IN GENERAL.—The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor or joint inventor of carrying out the invention. The following is a quotation of the first paragraph of pre-AIA 35 U.S.C. 112: The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor of carrying out his invention. Claims 28 and 32 are rejected under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, as failing to comply with the enablement requirement. The claims contain subject matter which was not described in the specification in such a way as to enable one skilled in the art to which it pertains, or with which it is most nearly connected, to make and/or use the invention. Factors to be considered in making this determination include: (A) The breadth of the claims; (B) The nature of the invention; (C) The state of the prior art; (D) The level of one of ordinary skill; (E) The level of predictability in the art; (F) The amount of direction provided by the inventor; (G) The existence of working examples; and (H) The quantity of experimentation needed to make or use the invention based on the content of the disclosure. While all of these factors are considered, a sufficient number for a prima facie case are discussed below. Instant claim 28 recites a method of preventing viral infection. The instant specification states that the compounds therein act to modulate the HBV replication cycle. The specification does not claim that the compounds therein act as viral entry inhibitors. The Examiner argues that a viral infection occurs as soon as a portion of a virus moves inside of the cell membrane of a host cell. One of ordinary skill in the art would not know how to use a compound provided by the instant specification, being a compound without the ability to inhibit viral entry, to stop viral entry into a host cell. This represents an insufficient amount of direction provided by the inventor. Claim 32, being dependent upon claim 28, does not correct the lack of enablement or narrow that claim to a scope wherein the lack of enablement does not apply. The Examiner determines that claims 28 and 32 are not properly enabled. 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 1-5, 7-8, 10, 12-13, 21, 23-24, 26, 28, and 32 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. Claim 1 recites the following phrases “(5- to 10-membered heteroaryl)” and “(C3-C7 cycloalkyl)”. It is not clear why these phrases are inside of parentheses, and the parentheses make it unclear if these are exemplary or required limitations of the claim. This renders claims 1-5, 7-8, 10, 12-13, 21, 23-24, 26, 28, and 32 indefinite. Applicant may choose to remove the parentheses around the items quoted above. Claim 24 is determined to be indefinite, because it unnecessarily incorporates a list of compounds from the specification. This type of reference is permitted only “in exceptional circumstances where there is no practical way to define the invention in words and where it is more concise to incorporate by reference than duplicating a drawing or table into the claim”. The specific compounds numbered 1-175 can be shown in the claims, and so this incorporation by reference is not necessary. See MPEP 2173.05(s). 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, 3-5, 7, 13, 26, 28, and 32 are rejected under 35 U.S.C. 102(a)(2) as being anticipated by: NEUBIG 2011 (WO 2011/035143 A2, International Publication Date 24 March 2011). NEUBIG teaches the following compound as compound 7 on page 86 therein. PNG media_image2.png 129 250 media_image2.png Greyscale This compound can be shown to fall within the scope of instant claim 1. Defining the variables of instant claim 1 as follows yields the compound of NEUBIG above: X is -N(Rx)-, Y is absent, Rx is H, ring A is a C6 aryl ring with one RA substituent, RA is a halogen, ring B is a C6 aryl ring with two RB substituents, each RB substituent is a C1 alkyl group substituted by three RB4 substituents, each RB4 group is a halogen, and R1 is H. Page 24 of NEUBIG teaches pharmaceutical formulations of the compounds therein, including compounds “in a pharmaceutically acceptable carrier or aqueous medium”. Together, claims 8, 10, and 12 teach the use of pharmaceutical formulations of the compounds therein for the treatment of “Hepatitis B surface antigen disease”. One of ordinary skill in the art would read this as being synonymous with “Hepatitis B”. 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. 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 1-5, 7, 10, 12-13, 21, and 26 are rejected under 35 U.S.C. 103 as being unpatentable over: GERLACH 2012 (US 8,309,542 B2, Date of Patent 13 November 2012) in view of: PATANI (Patani, G. A.; LaVoie, E. J. “Bioisosterism: A Rational Approach in Drug Design” Chem. Rev. 1996, 96, 3147-3176.). GERLACH teaches the following compound as Example 45 in column 53. This compound of GERLACH does not, in itself, anticipate any of the instant claims. The amide hydrogen appears to be omitted in the structure in column 53 (shown below), but one of ordinary skill in the art would understand a hydrogen to be present at that location, as shown in the structures in column 85 and 86 of GERLACH. GERLACH teaches medicaments of the compounds therein containing one or more inert carriers (claim 9). PNG media_image3.png 253 384 media_image3.png Greyscale PATANI generally teaches bioisosteres that were well-known in the chemical arts at the time. Table 48 of PATANI teaches common bioisosteres of amides, wherein the first bioisostere listed is the reversed amide. One of ordinary skill in the art, before the instant effective filing date, would have read the disclosure of GERLACH and seen the compounds there and would have at once envisaged the compounds therein with the opposite orientation of the amide bond, as taught by PATANI. This would have yielded the reversed amide version of Example 45 of GERLACH, as drawn below. This compound can be shown to fall within the scope of instant claim 1. Defining the variables of instant claim 1 as follows yields the compound rendered obvious by GERLACH below: X is -N(Rx)-, Y is absent, Rx is H, ring A is a 5-membered heteroaryl ring with one RA substituent, RA is a halogen, ring B is a 10-membered heteroaryl ring with one RB substituent, RB is a C1 alkyl group, and R1 is a C1 alkyl group. The artisan would have expected success in this change, because reversing the orientation of an amide was a well-known within the chemical arts, as shown by PATANI. PNG media_image4.png 288 485 media_image4.png Greyscale Regarding claim 21: Instant claim 21 narrows the definition of RB4, but does not require its presence. Therefore, as the compound rendered obvious above does not violate this narrower definition of RB4, it renders instant claim 21 obvious. Claims 1-5, 7-8, 10, 13, 21, 23, and 26 are rejected under 35 U.S.C. 103 as being unpatentable over: LINDSLEY 2013 (WO 2013/126856 A1, International Publication Date 29 August 2013) in view of: PATANI (Patani, G. A.; LaVoie, E. J. “Bioisosterism: A Rational Approach in Drug Design” Chem. Rev. 1996, 96, 3147-3176.). LINDSLEY teaches the following compound as the first compound on page 350 therein. LINDSLEY teaches pharmaceutical compositions of the compounds therein that include a pharmaceutically acceptable carrier (paragraph [00806]). This compound of LINDSLEY does not, in itself, anticipate any of the instant claims. PNG media_image5.png 206 440 media_image5.png Greyscale PATANI generally teaches bioisosteres that were well-known in the chemical arts at the time. Table 48 of PATANI teaches common bioisosteres of amides, wherein the first bioisostere listed is the reversed amide. One of ordinary skill in the art, before the instant effective filing date, would have read the disclosure of LINDSLEY and seen the compounds there and would have at once envisaged the compounds therein with the opposite orientation of the amide bond, as taught by PATANI. This would have yielded the reversed amide version of the compound of LINDSLEY copied above, as drawn below. This compound can be shown to fall within the scope of instant claim 1. Defining the variables of instant claim 1 as follows yields the compound rendered obvious by LINDSLEY below: X is -N(Rx)-, Y is absent, Rx is H, ring A is a C6 aryl ring with two RA substituents, each RA is a halogen, ring B is a 9-membered heteroaryl ring with three RB substituents, one RB is -(CH2)n-N(RB1)(RB2) wherein n is 0 and the other two RB substituents are C1 alkyl groups, RB1 is H, RB2 is H, and R1 is H. The artisan would have expected success in this change, because reversing the orientation of an amide was a well-known within the chemical arts, as shown by PATANI. PNG media_image6.png 190 581 media_image6.png Greyscale Regarding claim 21: Instant claim 21 narrows the definition of RB4, but does not require its presence. Therefore, as the compound rendered obvious above does not violate this narrower definition of RB4, it renders instant claim 21 obvious. Conclusion No claims are currently allowable. Any inquiry concerning this communication or earlier communications from the examiner should be directed to JOHN D MCANANY whose telephone number is (571)270-0850. The examiner can normally be reached 8:30 AM - 5:30 PM. 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, ANDREW D KOSAR can be reached at (571)272-0913. 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. /JDMc/Examiner, Art Unit 1625 /Andrew D Kosar/Supervisory Patent Examiner, Art Unit 1625
Read full office action

Prosecution Timeline

Apr 21, 2023
Application Filed
Feb 17, 2026
Non-Final Rejection — §102, §103, §112 (current)

Precedent Cases

Applications granted by this same examiner with similar technology

Patent 12583853
1H-PYRROLO[2,3-B]PYRIDINE DERIVATIVES AND RELATED COMPOUNDS AS BCL-2 INHIBITORS FOR THE TREATMENT OF NEOPLASTIC AND AUTOIMMUNE DISEASES
2y 5m to grant Granted Mar 24, 2026
Patent 12559497
IMIDAZOPIPERAZINE INHIBITORS OF TRANSCRIPTION ACTIVATING PROTEINS
2y 5m to grant Granted Feb 24, 2026
Patent 12552768
PYRIDINYLPYRAZOLE DERIVATIVE OR PHARMACEUTICALLY ACCEPTABLE SALT THEREOF AND USE THEREOF
2y 5m to grant Granted Feb 17, 2026
Patent 12545682
Heterocyclic Derivatives as P2X7 Receptor Antagonists
2y 5m to grant Granted Feb 10, 2026
Patent 12535735
Modified Thioxanthone Photoinitiators
2y 5m to grant Granted Jan 27, 2026
Study what changed to get past this examiner. Based on 5 most recent grants.

AI Strategy Recommendation

Get an AI-powered prosecution strategy using examiner precedents, rejection analysis, and claim mapping.
Powered by AI — typically takes 5-10 seconds

Prosecution Projections

1-2
Expected OA Rounds
67%
Grant Probability
99%
With Interview (+51.0%)
3y 2m
Median Time to Grant
Low
PTA Risk
Based on 49 resolved cases by this examiner. Grant probability derived from career allow rate.

Sign in with your work email

Enter your email to receive a magic link. No password needed.

Personal email addresses (Gmail, Yahoo, etc.) are not accepted.

Free tier: 3 strategy analyses per month