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 .
Claim Status
Claims 1-7 and 12-24 have been withdrawn.
Claim 29 has been amended.
Claims 8-11 and 25-28 have been cancelled.
Claims 31-38 have been added.
No new matter has been added.
Applicant’s election of Group III (claims 29-30), without traverse, is acknowledged.
Election/Restrictions
Applicant’s election without traverse of Group III (claims 29-30) and new claims 31-38 that read on the elected inventive group in the reply filed on 6/22/2026 is acknowledged.
Claims 1-7 and 12-24 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention, there being no allowable generic or linking claim. Election was made without traverse in the reply filed on 6/22/2026. Thus, claims 29-38 are presented and represent all claims currently under consideration.
Claims 29-38 are directed to an allowable compound. The restriction requirement between claims 1-7 and 12-23 (group I), drawn to a method of making a functionalized biomolecule, and claim 24 (group II), drawn to a method for using a linker compound for multiplexed analysis of a target biomolecule, as set forth in the Office action mailed on 4/22/2026, has been reconsidered in view of the allowability of claims to the elected invention pursuant to MPEP § 821.04(a). The restriction requirement is maintained because the nonelected claims do not require all the limitations of an allowable claim.
Claim Objections
Claim 35 is objected to because of the following informalities:
In line 3, “atom,” should read “atom.”
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 29-38 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 29 recites the limitation “wherein, R1 is an alkyl group or an aromatic ring having 1 to 12 carbon atoms” in line 4. The specification defines the term “aromatic” as referring to a hydrocarbon having a conjugated cyclic molecular structure and therefore suggests a distinction between a heterocyclic aromatic ring, which the specification defines as a ring that can include one or more N, O, or S atom (Specification; 0054). Thus, when interpreting the limitation “R1 is… an aromatic ring having 1 to 12 carbon atoms” in view of the specification, it is unclear how one could obtain an aromatic ring having 1-5, 7-9 or 11 carbon atoms, and this ambiguity renders the instant claim indefinite.
Regarding claims 30-38, these dependent claims do not resolve the indefiniteness of claim 30 detailed above.
Claim 30 recites the limitation “The compound of claim 29, wherein R1 is –CH2– and R2 is –CH–.” However, a compound of the formula of claim 29 wherein R2 is –CH– would result in a compound with a hexavalent carbon atom. This is not chemically possible, and this discrepancy renders the instant claim indefinite.
Claim 32 recites the limitation “wherein, R1 is an alkyl group or an aromatic ring having 1 to 6 carbon atoms” in lines 1-2. The specification defines the term “aromatic” as referring to a hydrocarbon having a conjugated cyclic molecular structure and therefore suggests a distinction between a heterocyclic aromatic ring, which the specification defines as a ring that can include one or more N, O, or S atom (Specification; 0054). Thus, when interpreting the limitation “R1 is… an aromatic ring having 1 to 6 carbon atoms” in view of the specification, it is unclear how one could obtain an aromatic ring having 1-5 carbon atoms, and this ambiguity renders the instant claim indefinite.
Claim 36 recites structural formulae comprising the variable “Cn”. However, there is no clear definition for the variable “Cn” in the instant claim or in the specification, and this ambiguity renders the instant claim indefinite.
Regarding claim 37, this dependent claim does not resolve the indefiniteness of claim 36 detailed above.
The following is a quotation of 35 U.S.C. 112(d):
(d) REFERENCE IN DEPENDENT FORMS.—Subject to subsection (e), a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
The following is a quotation of pre-AIA 35 U.S.C. 112, fourth paragraph:
Subject to the following paragraph [i.e., the fifth paragraph of pre-AIA 35 U.S.C. 112], a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
Claim 30 is rejected under 35 U.S.C. 112(d) or pre-AIA 35 U.S.C. 112, 4th paragraph, as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends.
Claim 30 recites “The compound of claim 29, wherein R1 is –CH2– and R2 is –CH–.” However, the formula of claim 29 on which the instant claim depends defines the variable R2 as P or S. Therefore, claim 30 broadens the scope of the formula of claim 29.
Applicant may cancel the claim, amend the claim to place the claim in proper dependent form, rewrite the claim in independent form, or present a sufficient showing that the dependent claim complies with the statutory requirements.
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 29-38 are rejected under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, as failing to comply with the written description requirement. The claim(s) contains subject matter which was not described in the specification in such a way as to reasonably convey to one skilled in the relevant art that the inventor or a joint inventor, or for applications subject to pre-AIA 35 U.S.C. 112, the inventor(s), at the time the application was filed, had possession of the claimed invention.
Claim 29 recites the following formula:
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324
651
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Wherein R2 is P or S. However, for instances wherein R2 is S, this structure would correspond to a tetravalent S(V) functional group that is inconsistent with the written description which shows a tetravalent S(VI) sulfonate functional group (Specification; 0031, Fig. 4):
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180
172
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Furthermore, the S(V) oxygen functional group corresponding to the claimed formula when R2 is S does not appear to be a chemically feasible compound, as taught by Bouillaud, who reviews the oxidation states of oxygenated sulfur compounds (see p. 3, Figure 2 in “Sulfide Oxidation Evidences the Immediate Cellular Response to a Decrease in the Mitochondrial ATP/O2 Ratio”; Biomolecules 2022, 12, 361, pages 1-19; published 02-24-2022). Since Applicant is in possession of a compound comprising a tetravalent S(VI) sulfonate functional group (Specification; 0031, Fig. 4), and is not in possession of the embodiment of recited formula of claim 29 wherein R2 is S (i.e., a tetravalent S(V) functional group), the instant claim is not adequately supported by the written description.
Regarding claims 30-38, these dependent claims do not resolve the written description requirement issue of claim 29 detailed above.
Subject Matter Free From the Prior Art
Claims 29-38, if interpreted correctly, appear to be free from the prior art and could be allowable if rewritten or amended to overcome the objection to claim 35, the rejections of claims 29-38 under 35 U.S.C. 112(b)/35 U.S.C. 112 (pre-AIA ), second paragraph, the rejection of claim 30 under 35 U.S.C. 112(d)/35 U.S.C. 112 (pre-AIA ), fourth paragraph, and the rejections of claims 29-38 under 35 U.S.C. 112(a)/35 U.S.C. 112 (pre-AIA ), first paragraph, set forth in this Office Action.
The following is a statement of reasons for the indication of allowable subject matter:
The prior art of record does not teach or suggest a compound comprising the formula recited in instant claim 29.
Exemplary prior art includes:
Deng et al. (“Synthesis of N-methoxy-1 phosphoryloxy imidates through a copper-catalyzed cross-dehydrogenative coupling of N-methoxylamides with phosphites”; Tetrahedron Lett. 2022, 105, 154049, pages 1-5; published 07-29-2022), who teaches the preparation of the following compound (page 3, Table 2, compound 3b):
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185
262
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Compound 3b of Deng is structurally similar to the genus of claim 29 when R1 is an aromatic ring having 6 carbon atoms, R2 is P, and R3 and R4 are linear hydrocarbon (i.e., ethyl groups).
Deng fails to teach a compound with a methylene group in between the P-O atom and the oxime group, and Deng also fails to teach R5 is a tagging reagent, as recited in instant claim 29.
Park et al. (WO 2021/187748 A1; published 09-23-2021), who teaches a method for selectively modifying nucleotides at the O6 position of guanine with diazoacetone (Abstract):
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457
1250
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Park further teaches that the labelled adducts can be further modified with a fluorophore via oxime conjugation, such as adducts 13b, 13c, 14, and 14a (Figure 9):
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These oxime adducts of Park correspond to the genus of claim 29 when R1 is an alkyl group and R5 is a tagging reagent.
Park fails to teach a terminal group that is at least an ethyl group (i.e., Park teaches methyl group instead), and Park also fails to teach the -O-R2O(OR3)(OR4) group (Park teaches an O-linked guanine residue instead), as recited in instant claim 29.
Tepe et al. (US 2006/0014234 A1; published 01-19-2006) teaches a method for the enrichment and characterization of phosphorylated peptides or proteins using a diazo moiety linked by an organic group to a substrate (Abstract). Example 4 of Tepe teaches an embodiment wherein small linkers can be introduced prior to resin binding (0220-0224; Example 4; Scheme 12):
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1061
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The adduct of Tepe when X = CH2 corresponds to the genus of claim 29 when R1 is an alkyl group, R2 is P, R3 is H, and R4 comprises a polar functional group.
Tepe fails to teach a compound with an oxime functional group connected to an R5 tagging reagent, as recited in instant claim 29. Instead, Tepe teaches a ketone functional group wherein the tagging reagent (i.e., biotin) is functionalized to the R1 side chain.
Although Deng, Park, and Tepe teach structural features of the genus of claim 29, none of the cited prior art teach each and every feature of the claimed genus. Furthermore, the skilled artisan would not be sufficiently motivated to modify or combine the cited prior art to arrive a compound comprising the formula of claim 29 with a reasonable expectation of success. Therefore, the claims are free from the prior art for the reasons of record and the reasons set forth above.
Conclusion
The prior art made of record and not relied upon is considered pertinent to Applicant’s disclosure.
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/D.R./Examiner, Art Unit 1692
/AMY C BONAPARTE/Primary Examiner, Art Unit 1692
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