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 .
Response to Amendment
An amendment filed on 25 June 2026 is acknowledged. Claims 1-3, 10, 13, 16, 44, and 46 are amended; claims 5 and 45 are newly canceled; and claims 47 and 48 are newly added. Claims 1-4, 10-23, 25, 28, 29, and 44, and 46-48 are pending; claims 14-23, 25, 28, and 29 are withdrawn; and claims 1-4, 10-13, 44, and 46-48 are examined herein on the merits.
In response to the amendments filed on 25 June 2026, an objection to the claims is added; the rejections under 35 USC 112(b) are changed; and the rejections over the prior art are changed. Claims 2, 10, 11, and 47 are drawn to allowable subject matter.
Claim Interpretation
Regarding the term "targeting moiety" recited in claims 2 and 10, the specification provides the following special definition ([0116], pages 22-23):
A targeting moiety as used herein refers to a chemical moiety that can recognize and bind to a receptor on a target such as an organelle in a cell or a specific cell type. Typically, the binding of a targeting moiety to a receptor on a target is a high affinity binding interaction. A targeting moiety can be a small molecule, a nucleic acid, a polypeptide, glycopeptide, proteoglycan, carbohydrate, lipid, or others identifiable to a person skilled in the art.
Claim Objections
Claim 1 is objected to because of the following informalities: In line 2, "Formula I" must be changed to "Formula II". 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.
Claims 10, 11, 44, and 47 are rejected under 35 U.S.C. 112(b) second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor regards as the invention.
Claim 10 recites the limitation "the targeting moiety." There is insufficient antecedent basis for this limitation in the claim. The examiner suggests replacing the limitation "the targeting moiety" with "a targeting moiety". Claims 11 and 47 are rejected for depending from claim 11.
Claim 44 is "The photoactivatable vibrational probe of claim 1, wherein R1 and R2 independently represent an aromatic or heteroaromatic ring." It is unclear how this claim further limits claim 1, which recites the limitation "wherein R1 and R2 independently represent a monocyclic or polycyclic, aromatic or heteroaromatic ring." The examiner interprets this limitation of claim 1 as follows: "wherein R1 and R2 independently represent a monocyclic aromatic ring, a monocyclic heteroaromatic ring, a polycyclic aromatic ring, or a polycyclic heteroaromatic ring."
Claim 47 recites the limitation "the at least one vibrational probe" in the last line of the claim. There is insufficient antecedent basis for this limitation because the claim previously introduces both "at least one photoactivatable vibrational probe of claim 11" and "at least one vibrational probe" (that is generated). The examiner suggests replacing the limitation "the at least one vibrational probe" in the last line with "the generated at least one vibrational probe".
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, 12, 13, 44, 46, and 48 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Dehmlow ("Die Addition von "Dichlorcarben" an Acetylene," Tetrahedron Letters 1965; refer to machine translation and SciFinder® abstract).
Regarding claims 1, 44, and 48, Dehmlow discloses synthesis of 2-phenyl-3-phenylethynylcyclopropenone (2) from diphenylbutadiyne (1) (page 2317/first page of translation; scheme on page 2319, copied below), thereby disclosing a compound having the formula of claims 1 and 48.
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Regarding the limitation of "a photoactivatable vibrational probe" and forming a "vibrational probe" of the given structure upon photoactivation, Dehmlow does not explicitly disclose this intended use and this functionality of 2-phenyl-3-phenylethynylcyclopropenone (2). However, because this compound is the same as the specific compound of claim 48 and the instant disclosure, Dehmlow's 2-phenyl-3-phenylethynylcyclopropenone (2) is interpreted as being inherently capable of being used for this purpose and having this functionality. Regarding composition claims, if the composition is the same, it must have the same properties (see MPEP § 2112.01, II.). The Courts have held that it is well settled that the recitation of a new intended use, for an old product, does not make a claim to that old product patentable. See In re Schreiber, 128 F.3d 1473, 1477, 44 USPQ2d 1429, 1431 (Fed. Cir. 1997) (see MPEP § 2114).
It is noted that a preamble is generally not accorded any patentable weight where it merely recites the intended use of a structure, and where the body of the claim does not depend on the preamble for completeness but, instead, the structural limitations are able to stand alone. See In re Hirao, 535 F.2d 67, 190 USPQ 15 (CCPA 1976) and Kropa v. Robie, 187 F.2d 150, 152, 88 USPQ 478, 481 (CCPA 1951).
Regarding claims 12 and 13, Dehmlow does not explicitly mention carbon isotopes. However, because the natural isotopic abundance of 13C is about 1.1% of carbon, for Dehmlow's 2-phenyl-3-phenylethynylcyclopropenone (2), 1.1% of molecules have 13C as X1, and 1.1% of molecules have 13C as X2, thereby anticipating the claims.
Regarding claim 46, Dehmlow discloses a composition comprising at least one photoactivatable vibrational probe of claim 1, as set forth above.
Regarding claim 46 and the limitation "for Raman imaging," while Dehmlow does not explicitly discloss these intended uses of the cyclopropenone compound, 2-phenyl-3-phenylethynylcyclopropenone is capable of being used for this purpose. Regarding composition claims, if the composition is the same, it must have the same properties (see MPEP § 2112.01, II.). The Courts have held that it is well settled that the recitation of a new intended use, for an old product, does not make a claim to that old product patentable. See In re Schreiber, 128 F.3d 1473, 1477, 44 USPQ2d 1429, 1431 (Fed. Cir. 1997) (see MPEP § 2114).
It is noted that a preamble is generally not accorded any patentable weight where it merely recites the intended use of a structure, and where the body of the claim does not depend on the preamble for completeness but, instead, the structural limitations are able to stand alone. See In re Hirao, 535 F.2d 67, 190 USPQ 15 (CCPA 1976) and Kropa v. Robie, 187 F.2d 150, 152, 88 USPQ 478, 481 (CCPA 1951).
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 3 and 4 are rejected under 35 U.S.C. 103 as being unpatentable over Dehmlow.
Regarding claims 3 and 4, Dehmlow does not disclose a compound having a structure according to Formula II, where each R1 and R2 is a substituted phenyl group (claim 3), or where one or more carbon atoms of one or both phenyl groups are substituted with a substituent selected from the claimed group, which includes alkoxyl.
However, Dehmlow investigated the addition of dichlorocarbene to variously substituted acetylenes (page 1 of translation), including the following substituted acetylene having a phenyl group substituted with an alkoxyl group (Table 1, page 2321), which is electron donating:
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Dehmlow further teaches that 2-phenyl-3-phenylethynylcyclopropenone (2) was formed from diphenylbutadiyne (1) "alongside 75–80% unreacted 1 and small amounts of other products" (page 2317/first page of translation), and that "alkynes substituted with electron-withdrawing groups do not react" (page 2 of translation). Accordingly, one of ordinary skill in the art would expect that increasing the electron density of the alkyne by modifying each phenyl group of 2-phenyl-3-phenylethynylcyclopropenone (2) with an electron-donating substituent (e.g., alkoxyl) would increase the yield of the cyclopropenone.
For the benefit of increasing the yield of cyclopropenone, it would have been obvious to one of ordinary skill in the art before the time of filing to modify the disclosure of Dehmlow such that each phenyl group of 2-phenyl-3-phenylethynylcyclopropenone (2) is substituted with an alkoxyl substituent to thereby provide the probe of claim 3 or 4.
Allowable Subject Matter
Claim 2 is objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the non-redundant limitations of claim 1 and overcoming the objection to claim 1.
Claims 10, 11, and 47 would be allowable if rewritten or amended to overcome the rejection(s) under 35 U.S.C. 112(b) set forth in this Office action.
The prior art of record does not disclose the formulae of claims 2 and 10 or the structures of claim 11.
Response to Amendment
Applicant's arguments filed on 25 June 2026 have been considered and are not fully persuasive or are moot in view of the new grounds of rejection.
The amendments to the claims have overcome the rejections under 35 U.S.C. 102(a)(1) based on Popik (US 2010/0210854) and Poloukhtine ("Highly Efficient Photochemical Generation of a Triple Bond: Synthesis, Properties, and Photodecarbonylation of Cyclopropenones," J. Org. Chem, 2003, IDS).
Applicant states "Applicant has amended claim 1 to include the features previously recited in claim 44 that is indicated as being allowable." In response, the previous version of claim 44 that was indicated as being allowable subject matter now matches the scope of dependent claim 2, which is now indicated to be allowable subject matter. Independent claim 1, which has been broadened with respect to the requirement that R1 or R2 comprises a targeting moiety, is rejected over the newly cited prior art of Dehmlow.
Conclusion
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to MICHELLE ADAMS whose telephone number is (571)270-5043. The examiner can normally be reached M, T, Th, and F, 12-4 P.M.
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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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/MICHELLE ADAMS/ Examiner, Art Unit 1797 /JENNIFER WECKER/Primary Examiner, Art Unit 1797
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