Prosecution Insights
Last updated: April 19, 2026
Application No. 18/255,855

HETEROARYL-ACETYLENES, PHARMACEUTICAL COMPOSITIONS THEREOF, AND THEIR THERAPEUTIC APPLICATIONS

Non-Final OA §102§112
Filed
Jun 02, 2023
Examiner
SHOWALTER, ALEXANDER KEITH
Art Unit
1629
Tech Center
1600 — Biotechnology & Organic Chemistry
Assignee
Eubulus Biotherapeutics Inc.
OA Round
1 (Non-Final)
54%
Grant Probability
Moderate
1-2
OA Rounds
3y 8m
To Grant
99%
With Interview

Examiner Intelligence

Grants 54% of resolved cases
54%
Career Allow Rate
37 granted / 69 resolved
-6.4% vs TC avg
Strong +52% interview lift
Without
With
+51.6%
Interview Lift
resolved cases with interview
Typical timeline
3y 8m
Avg Prosecution
46 currently pending
Career history
115
Total Applications
across all art units

Statute-Specific Performance

§101
2.5%
-37.5% vs TC avg
§103
34.3%
-5.7% vs TC avg
§102
14.5%
-25.5% vs TC avg
§112
32.6%
-7.4% vs TC avg
Black line = Tech Center average estimate • Based on career data from 69 resolved cases

Office Action

§102 §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 . Priority The present Application, filed June 2, 2023, is a national stage entry under 35 USC § 371 of International Patent Application No. PCT/CN2021/135247, filed December 3, 2022, which claims the benefit of U.S. Provisional Patent Application No. 63/121,300, filed December 4, 2020. Status of the Claims In the amendment filed January 13, 2024, claims 2-26, 29-47, 49-61, 70-76, 79-83, 88-115, and 120-127 are canceled. Claims 1, 27-28, 62, 64, 66, 68, 85, and 117-119 are amended. Claims 1, 27-28, 48, 62-69, 77-78, 84-87, and 116-119 are currently pending. Claim Rejections - 35 USC § 112(b) 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, 84-87, and 117-119 are indefinite: Claims 1, 84-87, and 117-119 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 is indefinite for reciting that U, V, X, and Z are each independently…-A-L1-L2-R3, and that one of U, V, X, and Z is -A-L1-L2-R3, because a person of ordinary skill in the art could not reasonably determine the metes and bounds of these limitations. In particular, since each of U, V, X, and Z is an in-ring component of the heteroaryl ring of Formula (I), it is unclear how it would be possible for any of these to be (as opposed to having as a substituent) -A-L1-L2-R3. For the purpose of examination against the prior art, claim 1 is construed as reciting that any of U, V, X, and Z can have a -A-L1-L2-R3 substituent, and that one of them does so [i.e. one is -C(A-L1-L2-R)-], as this interpretation is consistent with the instant working example compounds (e.g. compound C147), and with the sub-genus Formula (XII) of claim 28. Claims 117-119 are indefinite for depending from claim 1 without fulling curing the indefiniteness of claim 1 described just above. Claim 84 is indefinite because it is duplicative of claim 48 and therefore does not distinctly claim a separate invention. A note on claim interpretation: Claim 1 recites, “the proviso that at least one of U and Z is -N=, and one of U, V, X, and Z is -A-L1-L2-R3.” This is construed as requiring that one, and only one, of U, V, X, and Z is carries a -A-L1-L2-R3 substituent. Claims 66-69 are understood as indicating that the sole -A-L1-L2-R3 substituent is attached at position V, and that neither position U nor Z can have a -A-L1-L2-R3 substituent. Without this understanding, claims 66-69 would be indefinite due to the unclear description of the attachment of -A-L1-L2-R3 in claim 1, as discussed above. Claims 85-87 recite chemical formulae having variable moiety E that is not defined in the claims. It is noted that the specification defines moiety E at paragraphs [0275]-[0277] as being -C(H)= or -N=, and this definition is applied to these claims for examination. It is the examiner’s opinion that express incorporation of this definition into claim 85 would improve clarity, particularly since narrower definitions of moiety E, for “certain embodiments,” are presented in the specification at paragraph [0303]. To reiterate, the broader definition of moiety E at paragraphs [0275]-[0277] is considered controlling herein. Claim Rejections - 35 USC § 112(d) The following is a quotation of 35 U.S.C. 112(d): (d) REFERENCE IN DEPENDENT FORMS.—Subject to subsection (e), a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers. The following is a quotation of pre-AIA 35 U.S.C. 112, fourth paragraph: Subject to the following paragraph [i.e., the fifth paragraph of pre-AIA 35 U.S.C. 112], a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers. Claims 27 and 62-65 do not include all limitations of their base claim: Claims 27 and 62-65 are rejected under 35 U.S.C. 112(d) or pre-AIA 35 U.S.C. 112, 4th paragraph, as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends. In particular, these claims do not include all limitations of claim 1, from which they depend. Claim 27 is formally drafted as depending from claim 1, suggesting that Formula (IX) is a sub-genus of at least one of Formula (XLII) or (I). However, while Formula (IX) resembles Formula (XLII), the substituent at C4 of the thiazole ring in Formula (IX) (-A-L1-L2-R3) is not within the scope of the substituent of C4 of the thiazole ring of Formula (XLII) PNG media_image1.png 101 488 media_image1.png Greyscale Specifically, the -A-L1-L2-R3) substituent of Formula (IX) (claim 27) can include moieties that are outside the scope of the carbonyl diamide moiety of Formula (XLII) (claim 1). As such, Formula (IX) is not properly a sub-genus of Formula (XLII). Formula IX is not a sub-genus of Formula (I) because the thiazole ring of Formula (IX) is outside the scope of the six-membered ring of Formula (I). Therefore the invention of claim 27 does not include all limitations of claim 1 from which it depends. Likewise, claims 62-65 are drafted as depending from claim 1, but recite generic structure that are sub-genera of Formula (IX) (claim 27) and are outside the scope of claim 1. For the purpose of examination against the prior art, claim 27 is construed as being independent and claims 62-64 are construed as depending from claim 27. Applicant may cancel the claims, amend the claims to place the claims in proper dependent form, rewrite the claims in independent form, or present a sufficient showing that the dependent claims comply with the statutory requirements. 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. Claims 1, 28, 66-67, and 117-119 are anticipated by Chaffee: Claims 1, 28, 66-67, and 117-119 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by U.S. Patent No. 8,557,996 to Chaffee et al. (hereinafter, “Chaffee”). Claim 1 recites a compound of Formula (XLII) or (I): PNG media_image2.png 71 273 media_image2.png Greyscale PNG media_image3.png 74 138 media_image3.png Greyscale where the variable groups are as defined. Chaffee teaches compounds having a general Formula I PNG media_image4.png 84 129 media_image4.png Greyscale where the variable groups are as defined, and teaches these compounds are useful for the treatment of kinase mediated diseases (Abstract). In a working example, Chaffee teaches Example No. 76 PNG media_image5.png 261 293 media_image5.png Greyscale (col. 109 and 110, lines ~1-20). Example No. 76 is a compound of instant Formula (I) of instant claim 1, where R1 is pyridinyl (heteroaryl) substituted with Q that is -NRbRc with Rb and Rc each being hydrogen; U is N and V, X, Y, and Z are CH with V being substituted1 with -A-L1-L2-R3; A is -C(O)NR1a- with R1a being hydrogen; L1 is a bond; L2 is phenyl (aryl) substituted with Q that is alkyl that is further substituted with three Qa where each Qa of the three is fluoro (halo); and R3 is hydrogen. With respect to claim 28, Example No. 76 of Chaffee is a compound of Formula (XII) with R1, A, L1, L2 and R3 as defined above; with U being N, Z being CH2, and each R2a being hydrogen. Claim 66 recites a compound of Formula (XXVII) PNG media_image6.png 99 290 media_image6.png Greyscale where the variable groups are as defined. Claim 67, depending from claim 66, recites a compound of Formula (XXVIII) which is the same but requires that R3 be at the para position. Example No. 76 of Chaffee is a compound of Formulae (XXVII) and (XXVIII) where n and m are each zero and R1, R2a, U, Z, A, and R3 are as defined above. With respect to claim 117, Chaffee discloses a pharmaceutical composition containing a compound of the invention (e.g. Example No. 76) in combination with a pharmaceutically acceptable carrier, such as an excipient (col. 269, lines 51-57). With respect to claim 118-119, Chaffee discloses a method of treating a number of diseases, including cancer, comprising administering a disclosed compound (e.g. Example No. 76) to a patient in need thereof (see, e.g. col. 268, lines 28-33 and lines 16-20). Cancer is a proliferative disease (instant claim 118), and the instant specification at paragraph [00250] presents a proliferative disease, generally, as an example of a disorder, disease, or condition mediated by GPX4 (instant claim 119). Claims 27 and 62-63 are anticipated by Schwink: Claims 1, 28 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by U.S. Patent No. 7,968,550 to Schwink et al. (hereinafter, “Schwink”). Claim 27 recites a compound of Formula (IX) PNG media_image7.png 74 220 media_image7.png Greyscale where the variable groups are as defined. Schwink teaches N-aryl heterocycles useful as anorectic agents (Abstract) and having a generic formula I (not shown here). In a working example, Schwink discloses Example 291; 2-phenylethynylthiazole-4-carboxylic acid 4-(3-dimethylaminopyrrolidin-1-yl)phenyl-amide (col. 191, lines 22-35) PNG media_image8.png 88 296 media_image8.png Greyscale Above: Example 291 of Schwink. which is a compound of instant Formula (IX) where R1 is phenyl (aryl); R2a is hydrogen; A is -C(O)NR1a- with R1a being hydrogen; L1 is a bond; L2 is phenyl (aryl); and R3 is pyrrolidine (heterocyclyl) that is substituted with a substituent Q that is -NRbRc where each of Rb and Rc is methyl (C1 alkyl). Claim 62 recites a compound of Formula (XIII) PNG media_image9.png 83 284 media_image9.png Greyscale where the variable groups are as defined. Claim 63, depending from claim 62, recites a compound of Formula XIV which is the same but requires that R3 be at the para position. Schwink Example 291 is a compound of claims 62 and 63 where R1 is phenyl (C6 aryl); R2a is hydrogen; A is -C(O)NR1a- where R1a is hydrogen; n and m are each zero; and R3 is pyrrolididine (heterocyclyl) that is substituted with a substituent Q that is -NRbRc where each of Rb and Rc is methyl (C1 alkyl). Allowable Subject Matter Claims 48, 68-69, 77-78, and 85-87 are objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims. Claim 116 is allowed. Conclusion Any inquiry concerning this communication or earlier communications from the examiner should be directed to ALEXANDER K SHOWALTER whose telephone number is (571)270-0610. The examiner can normally be reached M-F 9:00 am to 5:00 pm, eastern time. 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, Jeffrey S Lundgren can be reached on (571) 272-5541. 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. /ALEXANDER K. SHOWALTER/Examiner, Art Unit 1629 /JEFFREY S LUNDGREN/Supervisory Patent Examiner, Art Unit 1629 1 As noted above, while claim 1 recites that “one of U, V, X, and Z is -A-L1-L2-R3,” it is assumed based on examples from the specification and claim 116 that it is meant to recite that one of U, V, X, and Z is substituted with -A-L1-L2-R3.
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Prosecution Timeline

Jun 02, 2023
Application Filed
Feb 06, 2026
Non-Final Rejection — §102, §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
54%
Grant Probability
99%
With Interview (+51.6%)
3y 8m
Median Time to Grant
Low
PTA Risk
Based on 69 resolved cases by this examiner. Grant probability derived from career allow rate.

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