DETAILED ACTION
This Office action details a first action on the merits for the above referenced application No. Claims 1-16 are pending in this application.
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 is a 35 USC 371 National Stage filing of international application No. PCT/SG2022/050572 filed on 11 Aug. 2022, and claims benefit under 35 USC 119(a)-(d) for foreign application No. SINGAPORE 10202108747Q filed on 11 Aug. 2021.
Information Disclosure Statement
The information disclosure statements (IDSs) submitted on 1 Dec. 2023 and 26 Jun. 2026 has been considered by the examiner.
Election/Restrictions
Applicant’s election without traverse of Group I, claims 1-11 and 16 in the reply filed on 15 Jun. 2026 is acknowledged.
Claims 12-15 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected Groups II-IV, there being no allowable generic or linking claim. Election was made without traverse in the reply filed on 15 Jun. 2026.
Applicant’s election without traverse of species BOPDsu in the reply filed on 15 Jun. 2026 is acknowledged.
Claims 2-10, and 16 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected species, there being no allowable generic or linking claim. Election was made without traverse in the reply filed on 15 Jun. 2025.
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Claim Objections
Claims 1 and 11 are objected to because of the following informalities: in claim 1, each instance of “represents” should be “is” and in claim 11, a period should be placed at the end of the claim. Appropriate correction is required.
Claim Rejections - 35 USC § 112
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 and 11 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.
Regarding claim 1, the phrase "more particularly" renders the claim indefinite because it is unclear whether the limitation(s) following the phrase are required. See MPEP § 2173.05(d).
The dependent claims fall therewith.
Claim Rejections - 35 USC § 102
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 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.
Claim(s) 1 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Huang et al. (Adv. Func. Mater.; published 12 Aug. 2020; see IDS filed on 1 Dec. 2023).
Regarding claim 1, Huang et al. disclose GCR1
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, and NCR1 and NCR2
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(Scheme 1; Fig. 3). GCR1 and NCR1 read on a compound of instant formula I
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wherein R1=CF3S(O)2, R2= H and R3= electron withdrawing group.
Claim(s) 1 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Cheng et al. (J. Am. Chem. Soc.; published 2019; see IDS filed on 1 Dec. 2023).
Regarding claim 1, Cheng et al. disclose the CFR compound
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(see scheme 1). CFR reads on a compound of instant formula I wherein R1=CF3S(O)2, R2= H and R3= electron withdrawing group.
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.
Claim(s) 1 and 11 is/are rejected under 35 U.S.C. 103 as being unpatentable over Cheng et al. (J. Am. Chem. Soc.; published 2019; see IDS filed on 1 Dec. 2023), in view of Matsumoto et al. (Tetrahedron Lett.; published 2005; see IDS filed on 26 Jun. 2026).
Cheng et al. teach as discussed above. Cheng et al. teach unimolecular chemo-fluoro-luminescent reporter for crosstalk-free duplex imaging of hepatotoxicity (see title). Cheng et al. teach a unimolecular chemo-fluoro-luminescent reporter (CFR) for crosstalk-free duplex imaging of drug induced hepatotoxicity (DIH). Because oxidative stress and cellular apoptosis have been found to be upregulated at the early stage of DIH prior to inflammatory response and liver failure, superoxide anion (O2.-) was chosen as an early biomarker for design of CFR. The CHL moiety is derived from a CHL dioxetane whose activity is inhibited by caging the phenol with a O2.- cleavable TF group. Differently, O2.- attacks the sulfonate ester of CFR and induces deprotection of Tf group leading to a highly unstable phenolate-dioxetane derivative. This intermediated undergoes spontaneous decomposition and releases photons as one of its products (pgs 10581-10582). Cheng et al. teach that CFR sensitively and specifically detected O2.-. CFR holds great promise for both preclinical drug screening and clinical diagnosis of DIH (pg. 10583).
Cheng et al. do not teach the compound of instant formula I wherein R3 is
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and X is O or the compound BOPDsu.
Matsumoto et al. teach bicyclic dioxetanes bearing 4-(benzoazol-2-yl)-3-hydroxyophenylm moiety: chemiluminescence profiled for base induced decomposition in aprotic medium and in aqueous solution (see title). Matsumoto et al. teach that adamantylidenedioxetane (1a) and bicyclic dioxetane (2a) are typical examples of dioxetanes (pg. 6075; scheme 1). Matsumoto et al. teach compounds 3a and 3b
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(scheme 2). The results in table 1 reveal that (a) dioxetanes (3a) and (3b) exhibit chemiluminescence with markedly high ΦCL even in aqueous systems (pg. 6076). The CT-induced decomposition rate of dioxetanes may vary in balance between the hydration of phenoxy anion and the hydrogen bonding of H2O molecules to O-O of an intermediary dioxetane in aqueous solution (pg. 6077).
It would have been obvious to a person of ordinary skill in the art before the effective filing date to modify the compound of Cheng et al. (CRF) by substituting the acrylamide group linked to the NIRF dye with a benzoazole such as a benzoxazole to arrive at BOPDsu as taught by Matsumoto et al. because the benzoxazole group would have been expected to advantageously enable a chemiluminescence probe capable of detecting superoxide anion (O2.-) with high ΦCL even in aqueous systems.
Claim(s) 1 and 11 is/are rejected under 35 U.S.C. 103 as being unpatentable over Huang et al. (Adv. Func. Mater.; published 12 Aug. 2020; see IDS filed on 1 Dec. 2023), in view of Matsumoto et al. (Tetrahedron Lett.; published 2005; see IDS filed on 26 Jun. 2026).
Huang et al. teach as discussed above. Huang et al. teach near infrared chemiluminescent reporters for in vivo imaging of reactive oxygen and nitrogen species (see title). Huang et al. teach GCR1
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and chemiluminescence imaging of GCR1 and NCR1 (see Fig. 3). (GCR1 reads on a compound of instant formula I
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wherein R1=CF3S(O)2, R2= H and R3=
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(electron withdrawing group)). As shown in Fig. S, the green reporter GCR1 showed 3596-fold chemiluminescence intensity enhancement at 540 nm upon addition of O2.- and ONOO- (pg. 5; Fig. S5).
Huang et al. do not teach the compound of instant formula I wherein R3 is
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and X is O or the compound BOPDsu.
Matsumoto et al. teach as discussed above.
It would have been obvious to a person of ordinary skill in the art before the effective filing date to modify the compound of Huang et al. (GCR1) by substituting the acrylate methyl ester with a benzoxazole to arrive at BOPDsu as taught by Matsumoto et al. because the benzoxazole group would have been expected to advantageously enable a probe suitable for detecting O2.- and ONOO- by chemiluminescence with high ΦCL even in aqueous systems.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to SEAN R DONOHUE whose telephone number is (571)270-7441. The examiner can normally be reached on Monday - Friday, 8:00 - 5:00 EST.
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/Michael G. Hartley/Supervisory Patent Examiner, Art Unit 1618
/SEAN R. DONOHUE/
Examiner, Art Unit 1618
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