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 .
The applicant's election of Group I and species, claims 1, 6-7, and 9-17, without traverse in their reply dated 8/31/2026 is acknowledged. Claims 2-5, 8, and 18-47 were withdrawn. Claims 1, 6-7, and 9-17 are pending and considered on the merits below.
Information Disclosure Statement
The Information Disclosure Statement filed on 4/22/2024 is in compliance with the provisions of 37 CFR 1.97 and has been considered. An initialed copy of the Form 1449 is enclosed herewith.
Specification
The disclosure is objected to because of the following informalities: it contains references to claims ([00101] and [00104]). The applicant is reminded that in U.S. patent practice, patent claims are interpreted in light of specification, and therefore, specification constructed by referencing the claims is improper. Further, as content of any of the claims is not certain until after that claims has been allowed, said uncertainty leaves the specification indefinite. The portions of the specification containing claim numbers should be edited to include the required text from the original claims and to remove the references to any claim numbers.
Appropriate correction is required. The applicant is reminded that no new matter should be added.
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.
Claim 14 is 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 14, the limitation “R1 to R11” is indefinite because it is unclear the specific scope of the claim. R1 to R11 implies R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, and R11, however there is no R5, R6, R7, or R9 present in the claims. For examination purposes the examiner interprets that the limitation means R1, R2, R3, R4, R8, R10, and R11.
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, 9-13, and 15-16 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Wang et al. (Angew. Chem. Int. Ed. 2006, 45, 5276 –5281).
Regarding claim 1, Wang describes a compound, ,wherein the compound is represented by Formula A or is a salt thereof:
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wherein X is CR1 or N; Z is O, S, N-R8, P-R8, O=P-R8, or O=P-OR8;
Q is N3,
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, alkynyl or substituted alkynyl; X" is R2 or X' -R1;
each X' is independently absent or X,
wherein, when present, I to 4 X' together form Ring B, fused to Ring A;
each of R1 and R2 is independently selected from H, halogen, FG, BDM, L-FG, L-BDM, L, L-BS, FD, L-FD, aliphatic, heteroaliphatic, acyl, ailyl, allenyl, propargyl, carboxy, sulfonate, PEG, WSG, alkoxy, aryloxy, alkylthiol, arylthiol, nitro, nitroso, cyano, amino, hydroxy, phosphonyl, sulfonyl, carbonyl, boronic acid, aryl, heteroaryl, and optionally substituted versions thereof;
each of R8, R10, and R11 is independently selected from H, alkyl, heteroalkyl, FG, BDM, L-FG, L-BDM, L, L-BS, FD, L-FD, acyl, sulfonyl, aryl, heteroaryl and optionally substituted versions thereof;
each of R12, R13, R14, and R15 is selected from independently H, alkyl, FG, BDM, L-FG, L-BDM, L, L-BS, FD, L-FD, acyl, sulfonyl, aryl, heteroaryl, and optionally substituted versions thereof (Table 1 : “
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”, Xs are CR1; R1s are H; Z is N-R8; R8 is H; Q is N3 R10 and R11 are H).
Regarding claims 9, 10, 11, and 16, Wang describes the compound of claim 1, wherein the compound is represented by Formula (II):
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(Table 1 : “
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”, Xs are CR1; R1-4 are H; Z is N-R8; R8 is H; Q is N3 R10 and R11 are H).
Regarding claim 12, Wang describes the compound of claim 9, wherein WSG is selected from sulfonate, PEG, carboxyalkyl, sulfonylalkyl, phosphonylalkyl, hydroxyalkyl, aminoalkyl, and ammoniumylalkyl (Examiner’s note: WSG is “water soluble group”. Additionally claim 12 only limits one member of the list provided in claim 9, thus claim 12 is rejected on the same grounds as claim 9 because claim 12's scope includes the scope of claim 9).
Regarding claim 13, Wang describes the compound of claim 9, wherein FG is selected from an activated ester, aldehyde, maleimide, amino, hydroxylamine, and hydrazine (Examiner’s note: FG is “functional group”. Additionally claim 13 only limits one member of the list provided in claim 9, thus claim 13 is rejected on the same grounds as claim 9 because claim 13's scope includes the scope of claim 9).
Regarding claim 15, Wang describes the compound of claim 9, BS is an antibody, antigen, protein, peptide, oligonucleotide, DNA, RNA, PNA, aptamer, or a cell (Examiner’s note: BS is “biological substrate”. Additionally claim 15 only limits one member of the list provided in claim 9, thus claim 15 is rejected on the same grounds as claim 9 because claim 15's scope includes the scope of claim 9).
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) 6, 7, and 14 is/are rejected under 35 U.S.C. 103 as being unpatentable over Wang et al. (Angew. Chem. Int. Ed. 2006, 45, 5276 –5281) in view of Ditmangklo et al. (Org. Biomol. Chem., 2019, 17, 9712).
Regarding claim 6, Wang describes the compound of claim 1, however is silent to wherein at least one of R1, R2, R8, R10, or R11 is or comprises FD or L-FD (Examiner’s note: FD is “fluorescent dye” and L is “linker”, thus L-FD is “linker and fluorescent dye”).
Ditmangklo describes similar compounds with “alkyne-modified styryl dyes 1–19” (scheme 1). Furthermore Ditmangklo suggests that this type of modification would allow for improved class of fluorescent dyes in biological applications (page 9712 “Styryl dyes are a class of fluorescent dyes that consist of an electron-deficient N-alkylated heterocyclic ring and an electron- rich aromatic ring connected to each other via a double bond to create an extended π-conjugated system.10,11 The excellent fluorescence properties of styryl dyes that are dependent on the environment make them useful as optical sensitizers”). This suggest motivation to incorporate fluorescent dyes into triazole compounds because this would provide for compound with excellent fluorescence properties.
Therefore it would have been obvious for one skilled in the art at the time the invention was filed to incorporate alkyne-modified styryl dyes as suggested by Ditmangklo into the compound of Wang because this would provide for compound with excellent fluorescence properties for used in biological applications.
Regarding claim 7, the combination describes above described the compound of claim 6, wherein FD is selected from coumarin, styryl, fluorescein, rhodamine, cyanine, BODIPY, phthalocyanine, porphyrin, and fluorescent protein (Ditmangklo: scheme 1 “alkyne-modified styryl dyes 1–19”).
Regarding claim 14, Wang describes the compound of claim 9, however is silent to wherein one of R1 to R11 comprises a FD or L-FD.
Ditmangklo describes similar compounds with “alkyne-modified styryl dyes 1–19” (scheme 1). Furthermore Ditmangklo suggests that this type of modification would allow for improved class of fluorescent dyes in biological applications (page 9712 “Styryl dyes are a class of fluorescent dyes that consist of an electron-deficient N-alkylated heterocyclic ring and an electron- rich aromatic ring connected to each other via a double bond to create an extended π-conjugated system.10,11 The excellent fluorescence properties of styryl dyes that are dependent on the environment make them useful as optical sensitizers”). This suggest motivation to incorporate fluorescent dyes into triazole compounds because this would provide for compound with excellent fluorescence properties.
Therefore it would have been obvious for one skilled in the art at the time the invention was filed to incorporate alkyne-modified styryl dyes as suggested by Ditmangklo into the compound of Wang because this would provide for compound with excellent fluorescence properties for used in biological applications.
Allowable Subject Matter
Claim 17 is 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.
The following is a statement of reasons for the indication of allowable subject matter:
References Wang et al. (Angew. Chem. Int. Ed. 2006, 45, 5276 –5281) in view of Ditmangklo et al. (Org. Biomol. Chem., 2019, 17, 9712) describe the limitations of claims 1 and 9, however fail to teach or suggest the specific compounds of claim 17.
None of the prior art discovered describes all the limitations alone or in combination, thus the prior art fails to teach or suggest all the limitations of claim 17.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to EMILY R BERKELEY whose telephone number is (571)272-9831. The examiner can normally be reached M-Th 9-6.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Lyle Alexander can be reached at (571) 272-1254. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/LYLE ALEXANDER/Supervisory Patent Examiner, Art Unit 1797
/EMILY R. BERKELEY/
Examiner
Art Unit 1796
