Prosecution Insights
Last updated: April 19, 2026
Application No. 18/571,754

Strained bi-functionalized trans-cyclooctenes

Non-Final OA §112
Filed
Dec 19, 2023
Examiner
PIHONAK, SARAH
Art Unit
1627
Tech Center
1600 — Biotechnology & Organic Chemistry
Assignee
Stichting Radboud Universiteit
OA Round
1 (Non-Final)
61%
Grant Probability
Moderate
1-2
OA Rounds
2y 11m
To Grant
99%
With Interview

Examiner Intelligence

Grants 61% of resolved cases
61%
Career Allow Rate
900 granted / 1477 resolved
+0.9% vs TC avg
Strong +44% interview lift
Without
With
+43.7%
Interview Lift
resolved cases with interview
Typical timeline
2y 11m
Avg Prosecution
47 currently pending
Career history
1524
Total Applications
across all art units

Statute-Specific Performance

§101
1.7%
-38.3% vs TC avg
§103
39.9%
-0.1% vs TC avg
§102
11.0%
-29.0% vs TC avg
§112
20.5%
-19.5% vs TC avg
Black line = Tech Center average estimate • Based on career data from 1477 resolved cases

Office Action

§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, filed 12/19/2023 is a National Stage entry of PCT/EP2022/069029, International Filing Date: 07/08/2022. PCT/EP2022/069029 claims foreign priority to 21184908.8, filed 07/09/2021. A certified copy of the foreign priority application is of record. Status of Claims Claims 1-10, 12-13, and 16-19 are currently pending. Claims 11 and 14-15 have been canceled. Claims 1-10, 12-13, and 16-19 were examined and are rejected. 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 1-10, 12-13, and 16-19 are rejected under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, because the specification, while being enabling for select compounds of formula (I), does not reasonably provide enablement for the full scope of compounds of formula (I). The specification does not enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to practice the invention commensurate in scope with these claims. See MPEP 2164. The factors to be considered in determining whether a disclosure meets the enablement requirements of 35 U.S.C. 112, first paragraph, have been described in In re Wands, 858 F.2d 731, 8 USPQ2d 1400 (Fed. Cir., 1988). The court in Wands states, “Enablement is not precluded by the necessity for some experimentation, such as routine screening. However, experimentation needed to practice the invention must not be undue experimentation. The key word is ‘undue’, not ‘experimentation’” (Wands, 8 USPQ2sd 1404). Clearly, enablement of a claimed invention cannot be predicated on the basis of quantity of experimentation required to make or use the invention. “Whether undue experimentation is needed is not a single, simple factual determination, but rather is a conclusion reached by weighing many factual considerations” (Wands, 8 USPQ2d 1404). Among these factors are: (1) the nature of the invention; (2) the breadth of the claims; (3) the state of the prior art; (4) the predictability or unpredictability of the art; (5) the relative skill of those in the art; (6) the amount of direction or guidance presented; (7) the presence or absence of working examples; and (8) the quantity of experimentation necessary. While all of these factors are considered, a sufficient amount for a prima facie case is discussed below. (1) The nature of the invention and (2) the breadth of the claims: Claim 1 is drawn to a compound of formula (I), wherein one of X1 and X2 is -Ra or -Z1-C(=Z2)-Rb, and the other is hydrogen; Z1, Z2, and Z3 are independently O, S, or NQN; Ra, Rb, Rc, and Rd are independently -O-Pr, -S-Pr, NQN1QN2, a leaving group, a pharmaceutically active substance, or a targeting moiety. The breadth of the claims is extensive, due to the nearly endless functional groups, moieties, and pharmaceutical agents encompassed for Ra, Rb, Rc, and Rd. (3) The state of the prior art and (4) the predictability or unpredictability of the art: The compounds of formula (I) are strained trans-cyclooctene (TCO) derivatives and the art acknowledges such compounds have applications in chemical biology, molecular diagnostics, and material science. The art also teaches the availability of such compounds can be limited for numerous reasons, including challenges with synthesis of TCO derivatives. Longo et. al., Bioconjugate Chem., 2020, 31, 2201-2210 teaches TCO as a highly reactive dienophile useful in bio-orthogonal reactions (pp. 2201-2202, 1st para). Additionally, TCO derivatives with a fused cyclopropyl ring exhibit enhanced stability as well as high reactivity (pp. 2201-2202, 1st para; p. 2202, Fig. 1). Longo further teaches that despite their diverse applicability, accessibility of these derivatives remains limited because of notable challenges with synthesis and structural modification (abstract; p. 2201-2202, in particular the right para on p. 2202 above Results & Discussion). Therefore, significant challenges and unpredictability exists in the art regarding the derivation of TCO compounds, such as those of formula (I). (5) The relative skill of those in the art: The relative skill of those in the art is expected to be high, such as that of a medicinal chemist or material scientist having an advanced degree. (6) The amount of direction or guidance presented and (7) the presence or absence of working examples: The specification provides examples showing the synthesis of the following select compounds of formula (I): PNG media_image1.png 200 400 media_image1.png Greyscale PNG media_image2.png 200 400 media_image2.png Greyscale PNG media_image3.png 200 400 media_image3.png Greyscale PNG media_image4.png 200 400 media_image4.png Greyscale PNG media_image5.png 200 400 media_image5.png Greyscale PNG media_image6.png 200 400 media_image6.png Greyscale PNG media_image7.png 200 400 media_image7.png Greyscale . As discussed previously, compounds of formula (I) as claimed are considerably broader in scope, particularly as Ra, Rb, Rc, and Rd are independently -O-Pr, -S-Pr, NQN1QN2, a leaving group, a pharmaceutically active substance, or a targeting moiety. Many millions of moieties and agents are included within the groups of “a pharmaceutically active substance” and “a targeting moiety”, and the specification only provides the above examples of compounds of formula (I). Thus, there is limited guidance and direction for arriving at the full scope of compounds of formula (I). Moreover, given the teachings by Longo regarding the limited availability of TCO derivatives due to noted challenges with synthesis and structural modification, a person of ordinary skill in the art would face undue experimentation in arriving at the full scope of compounds of formula (I). (8) The quantity of experimentation necessary: Considering the state of the art as discussed by the references above, particularly with regards to teachings of the prior art and the high unpredictability in the art as evidenced therein, and the lack of guidance provided in the specification, one of ordinary skill in the art would be burdened with undue experimentation to practice the invention commensurate in the scope of the claims. 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 1-10, 12-13, and 16-19 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 Ra, Rb, Rc, and Rd to be selected from various groups including “a pharmaceutically active substance, or a targeting moiety”. However, given the enormous breadth of agents included within these categories, the metes and bounds of the compounds of formula (I) wherein Ra, Rb, Rc, and Rd are selected from “a pharmaceutically active substance, or a targeting moiety” is unclear. Literally millions of structurally unrelated agents and moieties are potentially included within the categories of “a pharmaceutically active substance, or a targeting moiety”. Moreover, it is unclear how “a pharmaceutically active substance, or a targeting moiety” for Ra, Rb, Rc, and Rd would be connected to the rest of formula (I); would it be through a specific linker or common functional group? As such, claim 1 is indefinite. Claims 2-10, 12-13, and 16-19 are similarly rejected as they depend directly or indirectly from claim 1 and don’t provide further clarity. Regarding claim 5, the phrase "such as" renders the claim indefinite because it is unclear whether the limitations following the phrase are part of the claimed invention. See MPEP § 2173.05(d). The claim recites “silyls” followed by “such as ….”. It is uncertain if the limitation of the claim is broadly “silyls” or the narrower limitations following “such as”. Claim 8 recites the compound of general formula (III-a), (III-c), or (III-e), but then provides chemical structures only for formula (III-a). The other two shown chemical structures are labeled formula (IV-c) and (IV-e); since the body of the claim is not drawn to a compound of formula (IV-c) or (IV-e), and as the claim doesn’t provide chemical structures for (III-c) or (III-e), the metes and bounds aren’t clear, and the claim is indefinite. Claim 12 is drawn to a method of producing a conjugate comprising the steps of providing a compound as defined in claim 1; providing a second compound; and reacting the compound of claim 1 with the second compound to form a conjugate. The number of potential agents included within the scope of “a second compound” is substantial, in the tens of millions, encompassing any class of agent, possessing any chemical structure. The step of “reacting” a compound as defined in claim 1 with “a second compound” without any additional limitations of a specific reaction, type of reagents, or specific chemical transformations involved renders the claim indefinite, as the metes and bounds are vague and unclear. Claims 16-17 and 19 are similarly rejected as these claims depend from claim 12 and don’t provide further clarity. Information Disclosure Statement The IDS filed on 12/19/23 has been considered. Correspondence Any inquiry concerning this communication or earlier communications from the examiner should be directed to SARAH PIHONAK whose telephone number is (571)270-7710. The examiner can normally be reached Monday-Friday 9:00-5:30 EST. 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. SARAH . PIHONAK Primary Examiner Art Unit 1627 /SARAH PIHONAK/Primary Examiner, Art Unit 1627
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Prosecution Timeline

Dec 19, 2023
Application Filed
Feb 10, 2026
Non-Final Rejection — §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
61%
Grant Probability
99%
With Interview (+43.7%)
2y 11m
Median Time to Grant
Low
PTA Risk
Based on 1477 resolved cases by this examiner. Grant probability derived from career allow rate.

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