DETAILED ACTION
STATUS OF THE APPLICATION
Receipt is acknowledged of Applicants’ Amendments and Remarks, filed 4 December 2023, in the matter of Application No. 18/566,689. Said documents have been entered on the record. The Examiner further acknowledges the following:
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Claims 1-20 are pending.
Claims 5-7, 9-10, 12-14, 18, and 20 have been amended.
No claims have been cancelled.
Thus, claims 1-20 represent all claims currently under consideration.
Priority
The Examiner acknowledges US Provisional Application No. 63/202,547, filed on 16 June 2021.
Domestic Priority data as claimed by Applicant:
This application is a 371 of PCT/IB2022/054699 (05/19/2022)
PCT/IB2022/054699 has PRO 63/202,547 (06/16/2021)
Information Disclosure Statement (IDS)
The information disclosure statements submitted on 26 February 2024 and 11 August 2025 are in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statements are being considered by the Examiner.
Claim Objections
Claim 2 is objected to because of the following informalities:
In line 7, the phrase “…X1 is -O-;…” should be deleted.
In line 8, the phrase “…n is equal to 1;…” should be deleted.
In line 11, the phrase “…Q1 is -NH-(C=O)-X2;…” should be deleted.
Claim 3 is objected to because of the following informalities:
In line 7, the phrase “…X1 is -NH-;…” should be deleted.
In line 8, the phrase “…n is equal to 1;…” should be deleted.
In line 10, the phrase “…Q1 is -(C=O)-X2;…” should be deleted.
Claim 4 is objected to because of the following informalities:
In line 8, the phrase “…n is equal to 0;…” should be deleted.
Claim 15 is objected to because of the following informalities:
In line 3, “…derived form…” should read “derived from…”
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.
Claim 14 is 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 14 recites “…wherein the polymer comprises 0.1 to 50 mole percent first monomeric unit based on a total weight of monomeric units in the polymer.” However, mole percent is defined as a unit of concentration that expresses the percentage of total moles in a mixture that belong to a single component, and is not based on a total weight as recited in the instant claim. This ambiguity renders the instant claim indefinite. Further clarification is required. For examination purposes, the term “mole percent” will be interpreted in a manner consistent with the written description as a concentration based on the total moles of monomeric units in the polymer (Specification; page 10, lines 35-36).
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.
Claims 1, 4-5, 8, and 12-14 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Mespouille et al. (“Synthesis of Adaptive and Amphiphilic Polymer Model Conetworks by Versatile Combination of ATRP, ROP, and “Click Chemistry””; J. Polym. Sci. A. Polym. Chem. 2008, 46, 4997-5013; IDS of 08-11-2025; NPL Cite No. 2; hereinafter “Mespouille”).
Regarding claim 1, claims 4-5 depending from claim 1, and claim 8, Mespouille discloses an azido-containing poly(N,N-dimethylamino-2-ethyl methacrylate) (PDMAEMA)-based copolymer obtained from the copolymerization of DMAEMA with newly synthesized 2-(2-azidoethoxy)ethyl methacrylate (AEEMA) monomer (Mespouille; Abstract). The structure of the disclosed AEEMA monomer is as follows (Mespouille; page 5005, Scheme 3):
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444
170
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The structure of AEEMA monomer and the copolymer comprising AEEMA as a first monomeric unit disclosed by Mespouille anticipates Formula (I) of instant claims 1 and 8 when R1 methyl, X1 is -O-, n is equal to 0, and R3 is an ether group terminated with an azido group. The structure of AEEMA disclosed by Mespouille anticipates Formula (I-C) of instant claim 4 when R1 is methyl, X1 is -O-, and R3 is an ether group terminated with an azido group. In addition, the structure of AEEMA disclosed by Mespouille anticipates the monomer of instant claim 5 when R4 is methylene or ethylene (i.e., a C1 or C2 alkylene) and m is 1.
Regarding claims 12-13 depending from claim 8, Mespouille discloses the preparation of an azido-containing poly(N,N-dimethylamino-2-ethyl methacrylate) (PDMAEMA)-based copolymer obtained from the copolymerization of DMAEMA with newly synthesized 2-(2-azidoethoxy)ethyl methacrylate (AEEMA) monomer, wherein the copolymer has the following structure (Mespouille; Abstract; page 5009, Scheme 4):
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517
724
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The copolymer of Mespouille further comprises a second monomeric unit derived from N,N-dimethylamino-2-ethyl methacrylate (DMAEMA) that comprises a tertiary amino group and therefore anticipates instant claim 12. Furthermore, the ester group (–(C=O)-O–) can function as a hydrogen bond acceptor and the tertiary amino group can provide a hydrogen bond acceptor depending on the pH in a manner consistent with the written description (Specification; page 3, lines 4-6; page 8, lines 24-26), and therefore the copolymer of Mespouille anticipates instant claim 13.
Regarding claim 14 depending from claim 8, Mespouille discloses the synthesis of P(DMAEMA-co-AEEMA), wherein the polymer comprises 0.5 mmol of AEEMA and 9.5 mmol of DMAEMA (Mespouille; page 5000, Col. 2, final paragraph, ‘Synthesis of P(DMAEMA-co-AEEMA’). This corresponds to 5 mole percent first monomeric unit (i.e., AEEMA) based on the total moles of monomeric units in the polymer. Mespouille further discloses copolymerization studies of AEEMA and DMAEMA comprising a molar fraction of 3.40%, 3.5%, 3.6%, 3.88%, 4%, 4.59%, 5.05%, 5.1%, 10.8%, 11.3%, and 12.8% AEEMA (Mespouille; page 5006, Table 1; page 5007, Table 2; page 5008, Table 3). These values resides within the range recited in instant claim 14 and therefore anticipate the instant claim.
Claims 1 and 4-5 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Breitenkamp et al. (US 2008/0207913 A1; hereinafter “Breitenkamp”).
Regarding claim 1 and claim 4 depending from claim 1, Breitenkamp discloses monomers comprising poly(ethylene glycol) containing chemically disparate endgroups to provide bifunctional polymers, methods of preparing the same, and intermediates thereto (Breitenkamp; Title; Abstract). These compounds are useful in a variety of applications including the PEGylation of biologically active molecules (Breitenkamp; Title; Abstract).
Of particular note, Breitenkamp discloses azide-containing monomers 304-305 and 308-309 as exemplary compounds of general the following general formula use in the preparation of polymers, wherein n is selected in a range of from 50 ± 10 to 225 ± 10, and Ra and Rb are detailed below (Breitenkamp; Table 12):
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156
280
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59
842
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288
589
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331
646
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Thus, compounds 304-305 and 308-309 of Breitenkamp correspond to the following structures, wherein n is selected in a range of from 50 ± 10 to 225 ± 10 (Breitenkamp; Table 12):
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301
1022
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Compounds 304-305 of Breitenkamp anticipate Formula (I) of instant claim 1 when R1 is hydrogen (as in compound 304) or methyl (as in compound 305), X1 is -O-, n is equal to 0, and R3 is a polyether group terminated with an azido group. Compounds 304-305 of Breitenkamp also anticipate Formula (I-C) of instant claim 4 when R1 is hydrogen (as in compound 304) or methyl (as in compound 305), X1 is -O-, and R3 is a polyether group terminated with an azido group.
In addition, compounds 308-309 of Breitenkamp anticipate Formula (I) of instant claim 1 when R1 is hydrogen (as in compound 308) or methyl (as in compound 309), X1 is -NH-, n is equal to 0, and R3 is a polyether group terminated with an azido group. Compounds 308-309 of Breitenkamp also anticipate Formula (I-C) of instant claim 4 when R1 is hydrogen (as in compound 308) or methyl (as in compound 309), X1 is -NH-, and R3 is a polyether group terminated with an azido group.
Regarding claim 5 depending from claim 1, compounds 308-309 of Breitenkamp anticipate the instant claim when R4 is ethyl (i.e., a C2 alkylene) and m is 40 (Breitenkamp; Table 12, compounds 308 and 309 when n is 40).
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.
Claims 1, 8, and 10-13 are rejected under 35 U.S.C. 103 as being unpatentable over Breitenkamp et al. (US 2008/0207913 A1; hereinafter “Breitenkamp”).
Regarding claim 1, the teachings of Breitenkamp are incorporated herein as detailed above.
Regarding claim 8, although compounds 304-305 and 308-309 of Breitenkamp anticipate Formula (I) of instant claims 1 and 8, as detailed above, Breitenkamp not does explicitly disclose a polymer comprising a first monomeric unit derived from a monomer of Formula (I), as recited in instant claim 8.
However, Breitenkamp does teach that certain embodiments of the present invention provide a block or graft copolymer comprising a compound of the present invention to synthesize block copolymers for use as micellar therapeutic carriers (Breitenkamp; paragraph [0224]). As such, the skilled artisan would recognize from the teachings of Breitenkamp alone that any of the compounds 304-305 and 308-309 of Breitenkamp could be used as a first monomeric unit to obtain a polymer in a manner consistent with instant claim 8 to pursue a micellar therapeutic carrier with a reasonable expectation of success.
Therefore, it would have been prima facie obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to have obtained a polymer comprising one of compounds 304-305 or 308-309 as a first monomeric unit based on the teachings of Breitenkamp to arrive at the claimed invention. The motivation to do so would permit the skilled artisan to pursue, with a reasonable expectation of success, a block copolymer for use as micellar therapeutic carriers, as described above.
Regarding claims 10 and 13 depending from claim 8 and claim 11 depending from claim 10, Breitenkamp teaches that certain embodiments of the present invention provide a block or graft copolymer comprising a compound of the present invention to synthesize block copolymers for use as micellar therapeutic carriers, as detailed above (Breitenkamp; paragraph [0224]). Breitenkamp further teaches carboxylic acid containing compounds that can be used in the synthesis of copolymers, including carboxylic acid containing compounds with functionalities that can be used to initiate or mediate the growth of additional polymer blocks such as vinyl monomers (e.g. acrylate, styrene) (Breitenkamp; Table 1, Compounds 8 and 13-14; Table 3, Compounds 44, 49-54, 71, and 76-81; Table 4, Compounds 98, 103-108; Table 23, Compound 579; Table 24; Compound 583; paragraph [0224]):
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156
280
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153
658
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305
691
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191
835
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785
870
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410
894
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157
825
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954
861
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240
886
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159
849
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933
878
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244
916
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209
548
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218
591
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Thus, the skilled artisan could arrive at a polymer comprising a first monomer of comprising one of compounds 304-305 or 308-309 as a first monomeric unit, as detailed above, and further comprising a second monomeric unit comprising one of compounds (e.g., 8, 13-14, 44, 49-54, 71, 76-81, 98, 103-108, 579, or 583) that further comprises a carboxylic acid group, in a manner consistent with instant claims 10-11. Furthermore, the skilled artisan would recognize that the carboxylic acid group (–(C=O)-OH) can function as a hydrogen bond donating group or a hydrogen bond acceptor group, in a manner consistent with instant claim 13 and the written description (Specification; page 8, lines 33-34). Therefore, as with claim 8, it would have been prima facie obvious to arrive at the claimed invention based on the teachings of Breitenkamp.
Regarding claim 12 depending from claim 8 and further regarding claim 13 depending from claim 8, Breitenkamp teaches that certain embodiments of the present invention provides a block or graft copolymer comprising a compound of the present invention to synthesize block copolymers for use as micellar therapeutic carriers, as detailed above (Breitenkamp; paragraph [0224]). Breitenkamp further teaches primary amino group containing compounds that can be used in the synthesis of copolymers, including primary amino group containing compounds with functionalities that can be used to initiate or mediate the growth of additional polymer blocks such as vinyl monomers (e.g. acrylate, styrene) (Breitenkamp; Table 10, Compounds 237-242 and 244; Table 23, Compound 578; Table 24, Compound 582; paragraph [0224]):
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280
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334
608
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794
690
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169
643
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85
524
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187
560
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Thus, the skilled artisan could arrive at a polymer comprising a first monomer of comprising one of compounds 304-305 or 308-309 as a first monomeric unit, as detailed above, and further comprising a second monomeric unit comprising one of compounds (e.g., 237-242, 244, 578, or 582) that further comprises a primary amino group, in a manner consistent with instant claim 12. Furthermore, the skilled artisan would recognize that the amino group (-NH group, such as those not bonded to a carbonyl) can function as a hydrogen bond donating group or a hydrogen bond acceptor group, in a manner consistent with instant claim 13 and the written description (Specification; page 8, lines 32-34). Therefore, as with claim 8, it would have been prima facie obvious to arrive at the claimed invention based on the teachings of Breitenkamp.
Claims 15-20 are rejected under 35 U.S.C. 103 as being unpatentable over Mespouille et al. (“Synthesis of Adaptive and Amphiphilic Polymer Model Conetworks by Versatile Combination of ATRP, ROP, and “Click Chemistry””; J. Polym. Sci. A. Polym. Chem. 2008, 46, 4997-5013; IDS of 08-11-2025; NPL Cite No. 2; hereinafter “Mespouille”), in view of Oz et al. (“Modular Fabrication of Polymer Brush Coated Magnetic Nanoparticles: Engineering the Interface for Targeted Cellular Imaging”; ACS Appl. Mater. Interfaces 2016, 8, 19813-19826; hereinafter “Oz”).
Regarding claim 15, Mespouille teaches amphiphilic polymer conetworks comprising an azido-containing poly(N,N-dimethylamino-2-ethyl methacrylate) (PDMAEMA)-based copolymer obtained from the copolymerization of DMAEMA with newly synthesized 2-(2-azidoethoxy)ethyl methacrylate (AEEMA) monomer, and the structure of the disclosed AEEMA monomer anticipates the genus of Formula (I) of instant claims 1, 8, and 15, as detailed above (Mespouille; Abstract; page 5005, Scheme 3; page 5009, Scheme 4). In addition, Mespouille teaches that amphiphilic polymer conetworks have diverse applications, including the elaboration of nanoreactors, medical implants and immunoisolation devices, controlled drug delivery matrices, thermoresponsive gels, cell culture surfaces, contact lens materials, pervaporation membranes, solid-phase extractions, antifouling surfaces, promoted release hosts, etc. (Mespouille; page 4998; Col. 1, paragraph 1). Mespouille further teaches that the amphiphilic polymer conetworks of the present invention can be assembled into layered structures and crosslinked via “Click Chemistry” (Mespouille; page 4998, Col. 2, paragraphs 1-2; page 4999, Col. 1, paragraph 1 and Scheme 1):
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Although Mespouille teaches one or more layers of different polymers wherein at least one layer comprises a first polymer comprising a first monomeric unit derived from an azido-containing monomer of Formula (I), Mespouille fails to explicitly teach a first article comprising a substrate and a coating positioned on the substrate, wherein the coating comprises one or more layers of different polymers and wherein at least one layer comprises a first polymer comprising a first monomeric unit derived from an azido-containing monomer of Formula (I), as recited in instant claim 15.
However, Oz teaches the modular fabrication of polymer brush coated magnetic nanoparticles with functional attributes for various applications such as targeted drug delivery (Oz; Title; Abstract; page 19813, Col. 1, paragraph 1). Oz further teaches that a variety of polymeric coatings ranging from ultrathin coatings of amphiphilic copolymers to block copolymers have been utilized toward the fabrication of MNPs (Oz; page 19813, Col. 2, paragraph 1). Furthermore, Oz teaches that a functional polymer based coating should be antibiofouling in nature to minimize nonspecific attachment of proteins and comprise stable reactive groups for facile and efficient attachment of functional moieties such as imaging agents, drugs, and targeting groups (Oz; page 19815, Col. 1, paragraph 2). In addition, Oz teaches the preparation of surface-functionalized MNPs coated with chain-end “clickable” polymer brushes comprising azide “clickable” groups that can be functionalized with alkyne-containing molecules (Oz; page 19815; Col. 1, paragraph 3 and Col. 2, paragraph 1; page 19820, Scheme 4; page 19821, Figure 4c).
The prior art as taught by Mespouille and Oz reside in the overlapping technical field of azido-containing polymers with applications to drug delivery and as antifouling surfaces. In addition, Oz teaches that amphiphilic copolymers, such as those taught by Mespouille are suitable as polymeric coatings for magnetic nanoparticles. Therefore, the prior art is deemed analogous art, as described in MPEP § 2141.01(a). As such, the skilled artisan would be sufficiently motivated to incorporate the teachings of Oz into the method of Mespouille to pursue a polymeric-coated magnetic nanoparticle utilizing the amphiphilic copolymer of Mespouille for applications in drug delivery with a reasonable expectation of success. Such an endeavor would result in combining prior art elements according to known methods to yield predictable results, as described in MPEP § 2143(I)(A).
Therefore, it would have been prima facie obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to have modified Mespouille to incorporate the teachings of Oz to arrive at the claimed invention. The motivation to do so would permit the skilled artisan to pursue, with a reasonable expectation of success, a polymer coated magnetic nanoparticle with an antifouling surface and applications to drug delivery, as described above.
Regarding claim 16 depending from claim 15 and claim 17 depending from claim 16, the skilled artisan could arrive at bilayers comprising a first layer and a second layer adjacent to the first layer based on the amphiphilic copolymers of Mespouille (Mespouille; page 4998, Col. 2, paragraphs 1-2; page 4999, Col. 1, paragraph 1 and Scheme 1). Furthermore, the copolymer of Mespouille comprises 2-(2-azidoethoxy)ethyl methacrylate (AEEMA) monomer, whose structure anticipates the genus of Formula (I) of 15, as detailed above (Mespouille; Abstract; page 5005, Scheme 3; page 5009, Scheme 4). Finally, the P(DMAEMA-co-AEEMA) polymer of Mespouille comprises ester groups (–(C=O)-O–) that can function as hydrogen bond acceptors and tertiary amino groups that can provide a hydrogen bond acceptor or donor depending on the pH in a manner consistent with the written description (Specification; page 3, lines 4-6; page 8, lines 24-26). Thus, the skilled artisan would recognize that the second layer comprises a second polymer having a monomeric unit that can interact with the first polymer electrostatically or through hydrogen bonding between the adjacent polymer layers, in a manner consistent with instant claim 16. Thus, the skilled artisan could arrive at a coating comprising one or more bilayers, wherein the first and second polymers comprise first monomeric units derived from the azido-containing monomer of Formula (I), in a manner consistent with instant claims 16 and 17. Therefore, as with claim 15, it would have been prima facie obvious to arrive at the claimed invention based on the teachings of Mespouille in view of Oz.
Regarding claim 18 depending from claim 15 and claims 19-20 depending from claim 18, Oz teaches that an embodiment wherein terminal azido groups are functionalized with an alkyne-tethered BODIPY-derived fluorescent compound (Oz; page 19821, Figure 4c):
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The skilled artisan would recognize that Click reaction product of Oz is the result of an alkyne-containing (i.e., unsaturated compound) fluorescent dye and the azido group of the monomeric unit. Therefore, as with claim 15, it would have been prima facie obvious to arrive at the claimed invention based on the teachings of Mespouille in view of Oz.
Allowable Subject Matter
Claims 2-3, 6-7, and 9 are 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:
The prior art of record does not teach or suggest the monomer of Formula (I-A) of instant claim 2; the monomer of Formula (I-B) of instant claim 3; the monomer of claim 1 wherein R3 comprises a polyether-containing branched amino group according to the formula of instant claim 6; the monomer of claim 1 wherein R3 comprises a polyether-containing branched acrylamide group according to the formula of instant claim 7; and the polymer of claim 8, wherein the first monomeric unit of Formula (I) is derived from the monomers of claim 2, as recited in instant claim 9.
The closest prior art to the claimed invention is Breitenkamp. Breitenkamp discloses monomers comprising poly(ethylene glycol) containing chemically disparate endgroups to provide bifunctional polymers, methods of preparing the same, and intermediates thereto (Breitenkamp; Title; Abstract). These compounds are useful in a variety of applications including the PEGylation of biologically active molecules (Breitenkamp; Title; Abstract).
Although compounds 304-305 and 308-309 of Breitenkamp reside within the genus of Formula (I) of instant claims 1, 8, and 15, as detailed above (Breitenkamp; Table 12), Breitenkamp fails to teach monomers that reside within the genus of instant claims 2-3 and 6-7, and also fails to teach a polymer that comprises a monomer of claim 2, as recited in instant claim 9. Therefore, these 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.
Any inquiry concerning this communication or earlier communications from the Examiner should be directed to Derek Rhoades whose telephone number is (703)-756-5321. The Examiner can normally be reached Monday–Thursday, 7:30 am–5:00 pm EST; Friday, 7:30 am–4:00 pm EST.
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/D.R./Examiner, Art Unit 1692
/AMY C BONAPARTE/Primary Examiner, Art Unit 1692
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