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
Amendments to the drawings, specification and claims filed on 30 January 2026 are acknowledged. Claims 1, 3, 5, 10, 11, 13, and 16 are amended; claims 6, 8, and 9 are newly canceled; and claims 44-46 are newly added. Claims 1-5, 10-23, 25, 28, 29, and 44-46 are pending; claims 14-23, 25, 28, and 29 are withdrawn; and claims 1-5, 10-13, and 44-46 are examined herein on the merits.
In response to the amendments filed on 30 January 2026, the objection to the drawing is withdrawn; the objections to the specification are withdrawn; the objections to the claims are changed; the rejections under 35 USC 112(b) are partially withdrawn; the rejection under 35 USC 112(d) is withdrawn; and the rejections over the prior art are changed. Claims 10, 11, 44, and 45 are drawn to allowable subject matter.
This office action is non-final because the scope of "a targeting moiety" as recited in claim 1 (previously recited in claim 8) has been reconsidered with respect to compound 12 disclosed by Poloukhtine.
Claim Interpretation
Regarding the term "targeting moiety" recited in claims 1 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.
Regarding the term "alkyl" recited in claim 4 and "alkyl group" recited in claim 5, the specification provides the following special definition ([0069], page 13; bolding added):
The term “alkyl group” means a saturated linear or branched monovalent hydrocarbon chain having a specified number of carbon atoms including, for example, methyl, ethyl, n-propyl, isopropyl, tert-butyl, amyl, heptyl, and the like. The term “alkyl” can also refer to the radical of saturated aliphatic groups (i.e., an alkane with one hydrogen atom removed), including straight-chain alkyl groups, branched-chain alkyl groups, cycloalkyl (alicyclic) groups, alkyl-substituted cycloalkyl groups, and cycloalkyl-substituted alkyl groups. The term “alkyl” as used herein can include both “unsubstituted alkyls” and “substituted alkyls,” the latter of which refers to alkyl moieties having one or more substituents replacing a hydrogen on one or more carbons of the hydrocarbon backbone. Such substituents include, but are not limited to, halogen, hydroxyl, carbonyl (such as a carboxyl, alkoxycarbonyl, formyl, or an acyl), thiocarbonyl (such as a thioester, a thioacetate, or a thioformate), alkoxyl, phosphoryl, phosphate, phosphonate, phosphinate, amino, amido, amidine, imine, cyano, nitro, azido, sulfhydryl, alkylthio, sulfate, sulfonate, sulfamoyl, sulfonamido, sulfonyl, heterocycle, aralkyl, or an aromatic or heteroaromatic moiety. In some embodiments, an alkyl used herein can refer to an alkyl group having from one to ten carbons in its backbone structure, preferably one to six carbons (C1-6 alkyl).
Accordingly, the compounds disclosed by Popik (US 2010/0210854) that correspond to R6 and R8 together forming a (divalent) alkylene group do not satisfy the requirements of claim 5.
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.
Claim 13 is 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 13 recites the limitation "wherein one or both of X1 and X2 is a 13C atom." In the case where one of X1 and X2 is a 13C atom, it is unclear whether the formula of claim 13 requires all of the limitations of Formula I of claim 1. The examiner suggests the following limitation: "wherein X1 and X2 are each a carbon atom and one or both of X1 and X2 is a 13C atom."
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 1-4, 12, 13, and 46 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Popik (US 2010/0210854; newly cited).
Regarding claims 1-3, Popik discloses a photoactivatable probe (abstract; Figs. 2 and 3), having a structure according to Formula I, where n1 and n2 are both zero, and where R1 and R2 is each a substituted phenyl group (left compound of Fig. 2, copied below; compound 5, R=b of Fig. 3; compound 18, R=b and compound 19 of Fig. 12, copied below; [0022], structure copied below; [0100]);
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R2 comprises a targeting moiety ("R2 can be a PEGylated group, a biotinylated group," [0022], [0093], [0094], [0100]; compound 5, R=b of Fig. 3; compound 18, R=b and compound 19 of Fig. 12), and
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wherein the photoactivatable probe upon photoactivation is capable of forming a probe having the structure of claim 1, which comprises an alkynyl moiety generated from the cyclopropenone of Formula I, where n1 and n2 are both zero, and where R1 and R2 each is a substituted phenyl group (abstract; Figs. 2 and 3, [0050]).
Regarding the limitation of "a photoactivatable vibrational probe" and forming a "vibrational probe" upon photoactivation, while Popik does not explicitly discloses these intended uses of the cyclopropenone compounds, they are 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).
Regarding claim 4, Popik discloses that one carbon atom of one or both phenyl groups are substituted with a substituent selected from hydroxyl and alkoxy ([0022], [0100]; compound 5, R=b of Fig. 3; compound 18, R=b and compound 19 of Fig. 12).
Regarding claims 12 and 13, Popik does not explicitly mention carbon isotopes. However, because the natural isotopic abundance of 13C is about 1.1% of carbon, for the cyclopropenone compounds of Popik, 1.1% of molecules have 13C as X1, and 1.1% of molecules have 13C as X2, thereby anticipating the claims.
Regarding claim 46, Popik discloses 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 Popik does not explicitly discloses these intended uses of the cyclopropenone compounds, they are 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).
Claims 1-5, 12, 13, and 46 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Poloukhtine ("Highly Efficient Photochemical Generation of a Triple Bond: Synthesis, Properties, and Photodecarbonylation of Cyclopropenones," J. Org. Chem, 2003, IDS; previously relied upon), as evidenced by Popik (US 2010/0210854; newly cited).
Regarding claims 1-5, Poloukhtine discloses a photoactivatable compound (abstract; compound 12, Scheme 6, page 7839), having a structure according to the formula of claim 5, where R4, R5, R7, and R8 are hydrogen, R3 is an alkoxy group, and R6 is alkynyl and comprises a targeting moiety (discussed below).
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Poloukhtine's photoactivatable compound 12 is capable of forming, upon photoactivation, a compound comprising an alkynyl moiety recited in claim 1 (abstract; compound 13, Scheme 6, page 7839).
The alkynyl moiety of compound 12 satisfies the specification's special definition of a targeting moiety as "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" ([0116]), as evidenced by Popik. Popik teaches that "Examples of azide-reactive groups include alkynes" and that "The term 'azide reactive,' as used herein, refers to a material that selectively reacts with an azido modified group on another molecule to form a covalent chemical bond between the azido modified group and the azide reactive group" ([0052]). Popik further teaches that living cells can be labeled to express glycoproteins containing N-azidoacetyl-sialic acid ([0106], Fig. 2). According, the broadest reasonable interpretation of "targeting moiety" in view of the special definition of the instant specification encompasses the alkynyl moiety of Poloukhtine's compound 12.
Regarding the limitation of "a photoactivatable vibrational probe" and forming a "vibrational probe" upon photoactivation, while Poloukhtine does not explicitly discloses these intended uses, the cyclopropenone compound 12 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).
Regarding claims 12 and 13, Poloukhtine does not explicitly mention carbon isotopes. However, because the natural isotopic abundance of 13C is about 1.1% of carbon, for compounds 1i-1n and 12, 1.1% of molecules have 13C as X1, and 1.1% of molecules have 13C as X2, thereby anticipating the claims.
Regarding claim 46, Poloukhtine discloses 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 Poloukhtine does not explicitly discloses these intended uses of the cyclopropenone compound, it 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).
Allowable Subject Matter
Claims 10, 11, 44, and 45 are 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 the base claim and any intervening claims. If put in independent form, claims 10 and 11 should not recite Formula I or the second structure of claim 1, which are broader than the formulas of claim 10 and the structures of claim 11. For allowability of claims 10 and 11 over the prior art, it is not necessary to include the functional limitations recited in claim 1.
The prior art of record does not disclose the formulae of claim 10, the structures of claim 11, or the limitations of claim 44.
Response to Amendment
Applicant's arguments filed on 30 January 2026 have been considered and are not fully persuasive or are moot in view of the new grounds of rejection.
Regarding the rejection of claim 13 under 35 USC 112(b), Applicant's argument that the claim requires all of the limitations of claim 1 because claim 13 depends from claim 1 is unpersuasive because claim 13 does not define both X1 and X2 when only one of X1 and X2 is a 13C atom. The examiner suggests the following limitation: "wherein X1 and X2 are each a carbon atom and one or both of X1 and X2 is a 13C atom."
For the convenience of citing numbered paragraphs, the rejections based upon Popik's patent US 8,541,625 B2 have been changed to Popik's pre-grant publication US 2010/0210854.
Applicant cites Popik's highly generalized formula of [0009], which has not been relied upon in the rejection. Nevertheless, the relied upon embodiments of Popik are compounds that comprise an ethylene bridge connecting two phenyl groups. Applicant argues the following:
As shown in Formula (I) as claimed, R1 and R2 are not connected to one another, but simply attached to the three-membered cyclopropenone ring, i.e., there is no bridge between R1 and R2 …
Applicant's arguments regarding Popik are not persuasive. The scope of Formula I of claim 1 does not exclude being R1 and R2 connected to each other given that R1 and R2 independently represent a monocyclic or polycyclic, aromatic or heteroaromatic ring. Likewise, regarding claim 3, the scope of claim 3 does not exclude R1 and R2 being connected to each other given that R1 and R2 each is a substituted phenyl group. The corresponding moieties of Popik's compounds relied upon in the rejection (e.g., compound 19, Fig. 12) are each a substituted phenyl group. The specification does not set forth any special definitions regarding chemical structures, so the customary conventions have been applied to interpreting the scope of the chemical structures of the claims.
As an example of the customary conventions regarding generic chemical structure containing "R" groups and the possibility of ring formation, the prior art of Yamaguchi (JP 2017-53830 A; newly cited) discloses the following general chemical structure (claim 2, page 2; [0008], page 7; copied below left), that does not explicitly illustrate a bridging between R15 and R16. Nevertheless, as an option for R15 and R16, Yamaguchi teaches that "R15 and R16 together may represent a C1-4 alkylene group." Yamaguchi also provides a more specific example of the general formula that explicitly illustrates the bridging alkylene group that R15 and R16 together represent ([0032], copied below right).
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As shown by Yamaguchi (and as show by Popik's highly generalized formula of [0009] that was cited in Applicant's arguments), a generic moiety, in the absence of an excluding definition, does not exclude further ring formation, even if that further ring formation is not explicitly illustrated.
In contrast to claims 1-4, 8, 9, 12, 13, and 46, claim 5 has not been rejected for anticipation by Popik because the recited choices of R6 and R8 for the formula of claim 5 do not encompass R6 and R8 together forming a (divalent) alkylene group.
Regarding the rejections for anticipation by compound 12 of Poloukhtine, Applicant's arguments do not specifically address the intended interpretation of "a targeting moiety."
Conclusion
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