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 .
Continued Examination Under 37 CFR 1.114
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on 29 May 2026 has been entered.
Response to Amendment
Amendments to the claims filed on 29 May 2026 are acknowledged. Claims 1 and 30 are amended; and claims 4 and 18 are newly canceled. Claims 1, 6, 10, 11, 14, 17, 21, 30, 59, 67, 79, 81, 84, 88, 91, 93, and 95 are pending; claims 79, 81, 84, 88, and 91 are withdrawn; and claims 1, 6, 10, 11, 14, 17, 21, 30, 59, 67, 93, and 95 are examined herein on the merits.
In response to the amendments filed on 29 May 2026, an objection to the claims is added; a rejection under 35 USC 112(b) is added; and the rejections over the prior art are partially withdrawn and modified. Claims 1, 6, 10, 11, 14, 17, 21, 59, 67, 93, and 95 are drawn to allowable subject matter.
Election/Restrictions
Claim 1 is directed to an allowable product. Pursuant to the procedures set forth in MPEP § 821.04(b), claims 67 and 93, directed to the process of making or using the allowable product, previously withdrawn from consideration as a result of a restriction requirement, are hereby rejoined and fully examined for patentability under 37 CFR 1.104. Claims 79, 81, 84, 88, and 91, directed to the invention(s) of Groups III-VI, do not require all the limitations of an allowable product claim, and have NOT been rejoined.
Because a claimed invention previously withdrawn from consideration under 37 CFR 1.142 has been rejoined, the restriction requirement among groups I, II, and VII, as set forth in the Office action mailed on 19 July 2024 is hereby withdrawn. In view of the withdrawal of the restriction requirement as to the rejoined inventions, applicant(s) are advised that if any claim presented in a divisional application is anticipated by, or includes all the limitations of, a claim that is allowable in the present application, such claim may be subject to provisional statutory and/or nonstatutory double patenting rejections over the claims of the instant application.
Once the restriction requirement is withdrawn, the provisions of 35 U.S.C. 121 are no longer applicable. See In re Ziegler, 443 F.2d 1211, 1215, 170 USPQ 129, 131-32 (CCPA 1971). See also MPEP § 804.01.
Claim Objections
Claim 93 is objected to because of the following informalities: The hyphen within the limitation "metal-ion" must be removed. Appropriate correction is required.
Claim Interpretation
Independent claim 1 recites a compound comprising a dye, a polymer, and a recognition motif that is attached to the dye. The instant specification discloses the following special definition of "recognition motif" (page 13):
A "recognition motif" as used herein refers to a molecular entity that can bind to a binding entity and such binding alters the absorption spectrum of the dye and/or turns on fluorescence for the dye.
The specification further teaches that examples of recognition motifs can include crown ethers, cryptands, pincers, and/or chelating motifs (page 13).
Sufficient written description support for a compound comprising both a dye and a recognition motif attached to the dye is found in the disclosure of at least a recognition motif that is a crown ether or a cryptand.
The specification, including the working examples, disclose compounds that include a dye that is a tetrapyrrole macrocycle. A tetrapyrrole macrocycle includes heteroaryl ring nitrogen atoms that can serve as chelating motifs and bind to a binding entity to alter an absorption spectrum of the dye and/or turn on fluorescence for the dye. However, given that these heteroaryl ring nitrogen atoms are an essential part of the chromophore of the tetrapyrrole macrocycle dye, these heteroaryl ring nitrogen atoms cannot be reasonably interpreted as the recognition motif of claim 1 that is in addition to the dye. Likewise, these heteroaryl ring nitrogen atoms cannot be reasonably interpreted as being "attached to the dye" given that these nitrogen atoms are part of the dye.
Independent claim 1 recites "a polymer backbone that is a random copolymer."
The specification does not provide a special definition of a random copolymer, so "random copolymer" is interpreted according to its customary definition. The definition of "random copolymer" provided by IUPAC (previously cited) is reproduced below, with added annotation:
A copolymer consisting of macromolecules [plural] in which the probability of finding a given monomeric unit at any given site in the chain is independent of the nature of the adjacent units.
Note: In a random copolymer, the sequence distribution [which requires plural sequences] of monomeric units follows Bernoullian statistics.
Accordingly, the conventional meaning of "random copolymer" requires a plurality of macromolecules that are characterized by a sequence distribution (i.e., not all of the plurality of macromolecules have the same sequence of monomers).
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 67 is rejected under 35 U.S.C. 112(b) 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.
Dependent claim 67 is indefinite because it uses the terms "the first terminal end" and "the second terminal end" to refer to something different than how the terms are used in claim 1. In independent claim 1, these terms each refer to a part of the compound. However, in claim 67, these terms each refer to a part of a synthetic precursor to the compound, which is expected to be different (e.g., the synthetic precursor having an activated ester versus the compound having an amide).
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
Claim 30 is rejected under 35 U.S.C. 102(a)(1) as being anticipated by Morishima ("Characterization of Unimolecular Micelles of Random Copolymers of Sodium 2-(Acrylamido)-2-methylpropanesulfonate and Methacrylamides Bearing Bulky Hydrophobic Substituents," Macromolecules 1995; IDS of 3/29/2021; previously relied upon).
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Regarding claim 30, Morishima discloses poly(A/CD/Py) (Chart 1, annotated above) and poly(A/CD/2-Np) (Chart 2), each of which is a compound comprising:
a dye (pyrene, Chart 1; 2-naphthalene, Chart 2); and
a polymer having a polymer backbone (see annotation above, where backbone includes monomer(s) having a dye substituent) comprising one or more hydrophobic unit(s) (units of methacrylamides bearing cyclododecyl groups) and one or more hydrophilic unit(s) [units of sodium 2-(acrylamido)-2-methylpropane-sulfonate], wherein the polymer backbone comprises a first terminal end (first or left-most monomer position of backbone) and a second terminal end (last or right-most monomer position of backbone), wherein the first terminal end and the second terminal end are opposing ends of the polymer backbone (left-most versus right-most); and
wherein the dye is covalently attached to the first terminal end or the second terminal end of the polymer backbone (those polymer units randomly having a dye-bearing monomer unit as the first monomer position and/or the last monomer position of the polymer chain);
wherein the one or more hydrophobic unit(s) and the one or more hydrophilic unit(s) are present in the polymer in a ratio of about 1:1 to about 1:10 [in poly(A/CD/Py), Chart 1, the ratio is 49:50; in poly(A/CD/2-Np), Chart 2, the ratio is 27:70]; and
wherein the one or more hydrophobic unit(s) has a structure represented by Formula III [cyclododecyl(CD) unit of poly(A/CD/Py) or poly(A/CD/2-Np)], wherein R is C1 alkyl; R1 is -NH-; R' is a C12 cycloalkyl; R2 is hydrogen; and p is an integer from 1 to 100,000 (x=49, Chart 1; x=27, Chart 2).
Morishima discloses that poly(A/CD/Py) and poly(A/CD/2-Np) are random copolymers in which a free-radical terpolymerization is performed in the presence of all three monomer precursors (title; abstract; page 2875, para. bridging columns). This means that the dye-bearing monomer units are randomly positioned on the polymer backbone, including at the first monomer position and/or at the last monomer position of the polymer chain.
Given that 1 mol% 1PyMAm is used to prepare poly(A/CD/Py), approximately 1% of poly(A/CD/Py) molecules have pyrene dye attached to the first terminal end and approximately 1% of poly(A/CD/Py) molecules have pyrene dye attached to the second terminal end (Chart 1). These molecules anticipate the claimed compound.
Given that 3 mol% 2NpMAm is used to prepare poly(A/CD/2-Np), approximately 3% of poly(A/CD/2-Np) molecules have naphthalene dye attached to the first terminal end and approximately 3% of poly(A/CD/2-Np) molecules have naphthalene dye attached to the second terminal end (Chart 2). These molecules anticipate the claimed compound.
Allowable Subject Matter
Claims 1, 6, 10, 11, 14, 17, 21, 59, and 95 are allowed.
Claim 67 would be allowable if rewritten or amended to overcome the rejection under 35 U.S.C. 112(b) set forth in this Office action.
Claim 93 would be allowable if rewritten or amended to overcome the objection set forth in this Office action.
The compound of independent claim 1 is not disclosed or suggested by the prior art of record.
The amendments to claim 1 have overcome the rejections based upon Le Bohec ("Sol–gel reversible metallo-supramolecular hydrogels based on a thermoresponsive double hydrophilic block copolymer," Polym. Chem., 2016), which discloses a 192:28 ratio of NIPAM (hydrophobic units of N-isopropylacrylamide) to VDM (2-vinyl-4,4-dimethylazlactone, formed from hydrophilic precursor N-acryloyl-2-methylalanine, NAMA) monomers (page 6837).
The amendments to claim 1 have overcome the rejections based upon Janssen ("Screening a combinatorial peptide library to develop a human glandular kallikrein 2–activated prodrug as targeted therapy for prostate cancer," Mol Cancer Ther 2004), which discloses random amino acid residues rather than one or more hydrophobic units of Formula III.
The amendments to claim 1 have overcome the rejections based upon Yuan ("Amphiphilic block copolymer terminated with pyrene group: from switchable CO2-temperature dual responses to tunable fluorescence," RSC Adv., 2015) in view of York (WO 2018/044688 A1; IDS). Yuan discloses a mol% feed ratio of 96:4 of NIPAM (hydrophobic units of N-isopropylacrylamide) to DMAEMA (hydrophilic units of N,N-dimethylaminoethyl methacrylate) (page 13147, right col.).
Regarding the prior art of Trigo-López ("Colorimetric detection and determination of Fe(III), Co(II), Cu(II) and Sn(II) in aqueous media by acrylic polymers with pendant terpyridine motifs," Sensors and Actuators B 2016; cited 12/05/2024), the limitation that the polymer backbone of claim 1 is a "random copolymer" excludes an interpretation based upon those subset of sequences of a polymer of Trigo-López having a terpyridine-bearing monomer unit at the first monomer position and/or at the last monomer position of the polymer chain. This subset of sequences, being non-randomly selected, does not satisfy the ordinary and customary of a random copolymer (refer to claim interpretation section above).
Newly made of record are the post-dated reviews to Kar ("End-/side-chain fluorescent polymer conjugates: Stimuli-responsiveness and biological applications," J Polym Sci. 2024) and She ("Design strategy and recent progress of fluorescent probe for noble metal ions (Ag, Au, Pd, and Pt)," Coordination Chemistry Reviews 2021).
Response to Arguments
Applicant's arguments filed 29 May 2026 have been considered and are not fully persuasive and/or are moot in view of the new grounds of rejection.
Regarding the rejection of claim 30 for anticipation by Morishima, Applicant argues that Morishima fails to disclose a polymer having a ratio of about 1:1 to about 1:10 of hydrophobic unit(s) to hydrophilic unit(s). This argument is not persuasive. In Morishima's poly(A/CD/Py), the ratio is 49:50 (Chart 1). In Morishima's poly(A/CD/2-Np, the ratio is 27:70 (Chart 2).
Further regarding the rejection of claim 30 for anticipation by Morishima, Applicant argues the following:
Further, Morishima does not teach a dye that is covalently attached to the first terminal end or the second terminal end of the polymer backbone. Instead, the dye of Morishima is attached as a pendant functional group of a unit. As previously described, "terminal end" refers to one of the two ends of the polymer backbone, which are not a pendant functional group of a hydrophilic unit or hydrophobic unit.
In response, the Examiner disagrees that the broadest reasonable interpretation of a "terminal end" of a polymer backbone excludes a terminal end that is also a pendant group. Likewise, there is nothing in the claim that excludes attachment of a dye to a pendent group of a hydrophilic unit or hydrophobic unit.1 Applicant has not cited any evidence that the ordinary and customary meaning of "terminal end" excludes a pendant group. The phrase "terminal end" is not a term of art, as would be the case for the "N-terminus" or "C-terminus" of a peptide, which one of ordinary skill in the art would understand to exclude the "side chain" of an amino acid residue, where the terms "N-terminus," "C-terminus," and "side chain" of an amino acid each has a well-understood meaning as a term of art.
The specification provides a special definition of "terminal functional groups" that excludes pendant functional groups. However, as noted in a previous office action, the disclosed "terminal functional groups" are synthetic precursors to the disclosed compound comprising a dye and a biomolecule. If applicant wishes to exclude pendant-group-attachment of the dye of claim 30, the desired compound of claim 30 could be described as being prepared by reaction of a "terminal functional group" with a dye precursor (product-by-process language).
Alternatively, a limitation that the polymer backbone of claim 30 is a "random copolymer" would exclude an interpretation based upon those subset of sequences of poly(A/CD/Py) [or poly(A/CD/2-Np)] having a dye-bearing monomer unit at the first monomer position and/or at the last monomer position of the polymer chain. This subset of sequences, being non-randomly selected, does not satisfy the ordinary and customary of a random copolymer (refer to claim interpretation section above). For the same reason, claim 1 has not been rejected over Trigo-López ("Colorimetric detection and determination of Fe(III), Co(II), Cu(II) and Sn(II) in aqueous media by acrylic polymers with pendant terpyridine motifs," Sensors and Actuators B 2016; cited 12/05/2024).
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 on (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
1 The rejection is not based upon interpreting the monomer to which Morishima's is attached as being a claimed hydrophilic unit or hydrophobic unit.
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