DETAILED ACTION
Status of Claims
Claims 1-4 and 6-25 are currently pending. Claims 9-12 and 21-25 are currently under consideration and are the subject of this Office Action. This is the first Office Action on the merits of the claims. Non-elected claims 1-4, 6-8 and 13-20 are withdrawn from consideration. The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Status of Office Action: Non-Final.
Election/Restrictions
Applicant’s election of the claims of Group III (claims 9-12 plus newly added claims 21-25)] in the response filed on May 08, 2026 (to the March 11, 2026 Requirement for Restriction) is acknowledged. In response to applicant’s election, the claims of Group I (claims 1-4, 6-7 and 15-20), Group II (claim 8), and Group IV (claims 13-14) are withdrawn from further consideration pursuant to 37 C.F.R. § 1.142(b) as being drawn to a nonelected invention, there being no allowable generic or linking claim. Applicant has elected the claims of Group III with traverse. The traverse is based on applicant’s argument:
However, pursuant to 37 C.F.R. §§1.111 and 1.143, Applicant hereby traverses the requirement for restriction. A requirement for restriction presupposes an analysis of the subject application in light of the rules governing this practice, i.e., 37 C.F.R. § 1.499 and PCT Rules 13.1 and 13.2. PCT Rule 13.1, first sentence, states: "The international application shall relate to one invention only or to a group of inventions so linked as to form a single general inventive concept ('requirement of unity of invention')." (Emphasis added.) PCT Rule 13.2 states: "The expression 'special technical features' shall mean those technical features that define a contribution which each of the claimed inventions, considered as a whole, makes over the prior art." (Emphasis added.)
Contrary to the allegations in the Office Action, Applicant respectfully asserts that Groups I-IV represent a single inventive concept warranting examination in a single application. Particularly in view of the present amendments, at least Groups I, Ill, and IV all include the method for polymerizing amino acid N-carboxyanhydrides as recited in claim 1. Thus, at least Groups I, Ill, and IV are related to each other as aspects of a single inventive concept. Significantly, in view of this commonality, a search for a conjugate composition as delineated in claim 9 (Group III) would also function to search for art pertaining to methods of producing and using the conjugate composition (Groups I and IV, respectively). As provided, the search burden is substantially minimized by the existing overlap in at least Groups I, III, and IV.
Moreover, Applicant respectfully submits that the PCT Rules, which are the governing provisions in the instant case, specifically permit product claims and process of manufacture and process of use claims to be examined together in one application. See, for example, the provisions of 37 C.F.R. § l.475(b)(3) as also cited by the Examiner.
In addition, the Courts have recognized the advantages to the public interest to permit patentees to claim all aspects of their invention, as the applicant has done herein, so as to encourage the patentees to make a more detailed disclosure of all aspects of their invention. […].
May 08, 2026 Remarks, pp. 14-16. In response: it is noted that since the instant claims are indefinite and not patentable over LECOMMANDOUX (WO 2021/043865 A1, Publ. Mar. 11, 2021, as evidenced by US 2022/0325043 A1), as discussed below, restriction is still deemed proper.
Accordingly, the March 11, 2026 Requirement for Restriction is made FINAL, and claims 9-12 and 21-25 are examined as follows.
Claim Objections
The following claims are objected to because of the following informalities: Claim 23 is objected to because the claim should read:
23. (New) The conjugate of claim 22, wherein the amino acid is selected from methionine, valine, leucine, isoleucine, praline, hydroxyproline and alanine or derivatives of these amino acids; and/or
the polyamino acid is a homopolymer of the amino acids, a[[or]] copolymer of the amino acids, or a random copolymer of the amino acids; and/or
the protein is selected from the group consisting of enzymes, antibodies, cytokines and marker proteins; and/or
the small molecule is selected from the group consisting of benzylamine, ethylenediamine, p-methylaniline, lysine, glucosamine, p-methylthiophenol, mercaptan, doxorubicin, and gemcitabine.
Appropriate correction is required.
Claim Rejections – 35 U.S.C. § 112 - Indefiniteness
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 9-12 and 21-25 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 pre-AIA , that applicant regards as the invention.
A. Claim 9 is drawn to:
9. ([…]) A conjugate produced by a method for polymerizing amino acid N-carboxyanhydrides, wherein the method includes adding one or more amino acid N-carboxyanhydrides in water or a mixed solution of water and an organic solvent in the presence of an initiator to react to produce an initiator-polyamino acid conjugate, wherein the organic solvent is selected from the group consisting of: acetonitrile, pyridine, N,N-dimethylformamide, tetrahydrofuran and dimethyl sulfoxide,
wherein the initiator is a small molecule or large molecule containing a nucleophilic group selected from amino, imino, guanidyl, hydroxyl, and sulfuydryl; wherein the large molecule is a protein, a polypeptide or a nucleic acid, and/or wherein the small molecule is a small molecule drug, probe or dye.
wherein the recitation, “wherein the initiator is a small molecule or large molecule containing a nucleophilic group selected from amino, imino, guanidyl, hydroxyl, and sulfuydryl,” is indefinite for being on clear as to whether only the “large molecule” is limited to a “nucleophilic group selected from amino, imino, guanidyl, hydroxyl, and sulfuydryl,” or whether this limitations also applies to the “small molecule.” In this regard, it is noted that the Board has held: “if a claim is amenable to two or more plausible claim constructions, the USPTO is justified in requiring the applicant to more precisely define the metes and bounds of the claimed invention by holding the claim unpatentable under 35 U.S.C. §112, second paragraph, as indefinite.” Ex parte Miyazaki, 89 USPQ2d 1207, 1211 (BPAI 2008) (expanded panel). To the extent applicant intends the latter, examiner suggests amending claim 9 to read:
9. ([…]) A conjugate produced by a method for polymerizing amino acid N-carboxyanhydrides, wherein the method includes adding one or more amino acid N-carboxyanhydrides in water or a mixed solution of water and an organic solvent in the presence of an initiator to react to produce an initiator-polyamino acid conjugate, wherein the organic solvent is selected from the group consisting of: acetonitrile, pyridine, N,N-dimethylformamide, tetrahydrofuran and dimethyl sulfoxide,
wherein the initiator is a small molecule and/or a large molecule;
wherein the initiator contains[[ing]] a nucleophilic group selected from amino, imino, guanidyl, hydroxyl, and sulfuydryl;
wherein the large molecule is a protein, a polypeptide or a nucleic acid;[[,]] and[[/or]]
wherein the small molecule is a small molecule drug, probe or dye.
Subsequent claims 12 and 21-24 depend on claim 9 and are thus, indefinite as well.
B. Claim 10 is drawn to:
10. ([…]) A conjugate, which contains the following formula:
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wherein R1 is NH, CH2, S, O or Se; R2, R3, R4 and R5 are each independently hydrogen, optionally substituted C1-C12 alkyl, optionally substituted C2-6 alkenyl, optionally substituted C2-6 alkynyl, optionally substituted C1-C12 heteroalkyl, C2-6 heteroalkenyl, C2-6 heteroalkynyl, halogen, hydroxyl, C6-C12 aryl, C6-C12 heteroaryl, -OC(=O)-optionally substituted C1-6 alkyl, - OC(=O)-optionally substituted C2-6 alkenyl, -OC(=O)-optionally substituted C2-6 alkynyl, -OC(=O)-optionally substituted C1-6 heteroalkyl, -OC(=O)-C2-6 heteroalkenyl, -OC(=O)-C2-6 heteroalkynyl, -S-C(=O)-optionally substituted C1-6 alkyl, -S-C(=O)-optionally substituted C2-6 alkenyl, -S-C(=O)-optionally substituted C2-6 alkynyl, -S-C(=O)-optionally substituted C1-6 heteroalkyl, -S-C(=O)-C2-6 heteroalkenyl, -S-C(=O)-C2-6 heteroalkynyl, -N3, -C1-6 alkyl-N3, -C1-6 heteroalkyl-N3, -NHCOR', -NHCOOR' or -NR1R2, optionally substituted C6-C12 aryl, or optionally substituted C6-C12 heteroaryl, wherein R' is hydrogen, halogen, optionally substituted C1-6 alkyl, optionally substituted C2-6 alkenyl, optionally substituted C2-6 alkynyl, optionally substituted C1-6 heteroalkyl or optionally substituted C6-C12 aryl, R1 and R2 are each independently hydrogen, halogen, optionally substituted C1-6 alkyl, optionally substituted C2-6 alkenyl, optionally substituted C2-6 alkynyl, optionally substituted C1-6 alkoxy or optionally substituted C6-C12 aryl or optionally substituted C6-C12 heteroaryl; the protein is selected from enzymes, antibodies, cytokines and marker proteins; wherein n is 1-200, and m is 1-X, wherein X is the number of reactive lysines on the protein, and/or the degree of dispersion of the polymer is 1-1.5.
wherein the use of “and/or” in the requirements “wherein n is 1-200, and m is 1-X, wherein X is the number of reactive lysines on the protein, and/or the degree of dispersion of the polymer is 1-1.5” renders the metes and bounds of the claim unclear. The use of “and/or” suggests at least one of the embodiments:
(1) “n is 1-200,”
(2) “m is 1-X, wherein X is the number of reactive lysines on the protein”
(3) “the degree of dispersion of the polymer is 1-1.5,”
is required, potentially making the remaining two not required. For instance, if (3) is met, then (1) or (2) would not be required, whereby the valines of “n” and “m” in the formula of claim 10 would be undefined, and therefore, indefinite. In this regard, examiner suggests amending claim 10 to read:
10. ([…]) A conjugate, which contains the following formula:
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wherein
R1 is NH, CH2, S, O or Se;
R2, R3, R4 and R5 are each
independently hydrogen,
optionally substituted C1-C12 alkyl,
optionally substituted C2-6 alkenyl, optionally substituted C2-6 alkynyl,
optionally substituted C1-C12 heteroalkyl, C2-6 heteroalkenyl, C2-6 heteroalkynyl, halogen, hydroxyl, C6-C12 aryl, C6-C12 heteroaryl, -OC(=O)-optionally substituted C1-6 alkyl, - OC(=O)-optionally substituted C2-6 alkenyl, -OC(=O)-optionally substituted C2-6 alkynyl, -OC(=O)-optionally substituted C1-6 heteroalkyl, -OC(=O)-C2-6 heteroalkenyl, -OC(=O)-C2-6 heteroalkynyl, -S-C(=O)-optionally substituted C1-6 alkyl, -S-C(=O)-optionally substituted C2-6 alkenyl, -S-C(=O)-optionally substituted C2-6 alkynyl, -S-C(=O)-optionally substituted C1-6 heteroalkyl, -S-C(=O)-C2-6 heteroalkenyl, -S-C(=O)-C2-6 heteroalkynyl, -N3, -C1-6 alkyl-N3, -C1-6 heteroalkyl-N3, -NHCOR', -NHCOOR' or -NR1R2,
optionally substituted C6-C12 aryl, or
optionally substituted C6-C12 heteroaryl,
wherein R' is hydrogen, halogen, optionally substituted C1-6 alkyl, optionally substituted C2-6 alkenyl, optionally substituted C2-6 alkynyl, optionally substituted C1-6 heteroalkyl or optionally substituted C6-C12 aryl,
wherein R1 and R2 are each independently hydrogen, halogen, optionally substituted C1-6 alkyl, optionally substituted C2-6 alkenyl, optionally substituted C2-6 alkynyl, optionally substituted C1-6 alkoxy or optionally substituted C6-C12 aryl or optionally substituted C6-C12 heteroaryl;
the protein is selected from enzymes, antibodies, cytokines and marker proteins;
wherein n is 1-200, and m is 1-X, wherein X is the number of reactive lysines on the protein, and[[/or]] the degree of dispersion of the polymer is 1 to [[-]]1.5.
If applicant intends a requirement for “degree of dispersion of the polymer” to be optional, then this requirement should be recited as a separate, dependent claim. Subsequent claims 11 and 25 depend on claim 1 and are thus, indefinite as well.
C. Claim 22 is drawn to:
22. ([…]) The conjugate of claim 21, wherein the water or the mixed solution of water and an organic solvent has a buffer salt; and/or wherein the amino acid comprises glycine, alanine, valine, leucine, isoleucine, methionine, praline, tryptophan, serine, tyrosine, cysteine, phenylalanine, asparagine, glutamine, threonine, aspartic acid, sarcosine, glutamic acid, lysine, arginine, histidine, £-nitrogenbenzyloxycarbonyl lysine, glutamic acid benzyl ester, hydroxyproline, (S)-2-amino-4-((3-(benzylamino )-3-oxypropyl)seleno )butyric acid, penicillamine, oxy-tert-butyl-serine, £-nitrogentrifluoroacetyl L-lysine, or homocysteine or derivatives of these amino acids or a homocysteine derivative in which the sulfuydryl group in homocysteine is replaced by a selenoalkoxy group.
wherein the use of “these” in the recitation, “or homocysteine or derivatives of these amino acids or a homocysteine derivative in which the sulfuydryl group in homocysteine is replaced by a selenoalkoxy group,” renders the metes and bounds of the claim unclear whether of not “these” refers to the previously recited “the amino acid” or some other grouping because of term inconsistency. In this regard, examiner suggests amending claim 22 and adding a further dependent claim for a “homocysteine derivative in which the sulfuydryl group in homocysteine is replaced by a selenoalkoxy group”:
22. ([…]) The conjugate of claim 21, wherein the water or the mixed solution of water and an organic solvent has a buffer salt; and/or wherein the amino acid comprises glycine, alanine, valine, leucine, isoleucine, methionine, praline, tryptophan, serine, tyrosine, cysteine, phenylalanine, asparagine, glutamine, threonine, aspartic acid, sarcosine, glutamic acid, lysine, arginine, histidine, £-nitrogenbenzyloxycarbonyl lysine, glutamic acid benzyl ester, hydroxyproline, (S)-2-amino-4-((3-(benzylamino )-3-oxypropyl)seleno )butyric acid, penicillamine, oxy-tert-butyl-serine, £-nitrogentrifluoroacetyl L-lysine, , combinations thereof or derivatives thereof
[…]
X. (New) The conjugate of claim 22, wherein the amino acid comprises a homocysteine derivative in which the sulfuydryl group in homocysteine is replaced by a selenoalkoxy group.
Subsequent claim 23 depend on claims 22 and is thus, indefinite as well.
Further clarification is required.
Claim Rejections – 35 U.S.C. § 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)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention.
Claims 9, 12 and 21-23 are rejected under 35 U.S.C. § 102(a)(2) as being anticipated by LECOMMANDOUX (WO 2021/043865 A1, Publ. Mar. 11, 2021, Filed Sep. 3, 2019; as evidenced by as evidenced by US 2022/0325043 A1, Publ. Oct. 13, 2022, for English language translation; on 02/05/2024 IDS).
Paragraph numbers for Lecommandoux refer to US 2022/03250453 A1 as an English language translation of WO 2021/043865 A1. Lecommandoux is directed to:
Title: METHOD FOR PREP ARING CONTROLLED PEPTIDE-BASED POLYMERS AND COPOLYMERS IN AN AQUEOUS SOLUTION
Abstract: The present invention relates to a "one-pot" method for preparing an aqueous solution of nanoparticles with amphiphilic block copolymers and comprising polypeptide units, the method comprising at least one step (El), in an aqueous solvent, consisting of bringing together: - at least one hydrophilic polymer (PI) comprising at least one amine function, and - at least one hydrophobic α-amino acid N-carboxyanhydride monomer.
Lecommandoux, title & abstract. In this regard, Lecommandoux discloses claim embodiments drawn to a “‘one pot’ method for preparing an aqueous solution of nanoparticles of amphiphilic block copolymers and comprising polypeptide units”:
1. A “one pot” method for preparing an aqueous solution of nanoparticles of amphiphilic block copolymers and comprising polypeptide units, said method comprising at least one step (E1) in an aqueous solvent free of organic solvent, consisting of bringing together:
at least one hydrophilic polymer (P1) comprising at least one amine function, and
at least one hydrophobic α-amino acid N-carboxyanhydride monomer.
2. The method according to claim 1 wherein the hydrophobic α-amino acid N-carboxyanhydride monomer has the following formula (I):
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where R is the side chain of an optionally protected, natural or modified, hydrophobic α-amino acid.
3. The method according to claim 1, wherein the polymer (P1) is selected from the group consisting of: polyethers, polyesters, poly(meth)acrylates, polysaccharides, polypeptides, polypeptoids, DNA and protein derivatives.
Lecommandoux, claims 1-3.
Regarding claim 9 and the requirements:
9. (Currently amended) A conjugate produced by a method for polymerizing amino acid N-carboxyanhydrides, wherein the method includes adding one or more amino acid N-carboxyanhydrides in water or a mixed solution of water and an organic solvent in the presence of an initiator to react to produce an initiator-polyamino acid conjugate, wherein the organic solvent is selected from the group consisting of: acetonitrile, pyridine, N,N-dimethylformamide, tetrahydrofuran and dimethyl sulfoxide,
wherein the initiator is a small molecule or large molecule containing a nucleophilic group selected from amino, imino, guanidyl, hydroxyl, and sulfuydryl; wherein the large molecule is a protein, a polypeptide or a nucleic acid, and/or wherein the small molecule is a small molecule drug, probe or dye.
Lecommandoux clearly teaches a “‘one pot’ method for preparing an aqueous solution of nanoparticles of amphiphilic block copolymers and comprising polypeptide units” (Lecommandoux, claims 1-3), WHEREBY it is noted:
“at least one hydrophobic α-amino acid N-carboxyanhydride monomer” (Lecommandoux, claims 1-3), reads on “one or more amino acid N-carboxyanhydrides” of claim 9; and
“at least one hydrophilic polymer (P1) comprising at least one amine function” (Lecommandoux, claim 1), wherein “wherein the polymer (P1) is selected from the group consisting of: polyethers, polyesters, poly(meth)acrylates, polysaccharides, polypeptides, polypeptoids, DNA and protein derivatives” (Lecommandoux, claim 3) reads on an “initiator,” wherein “wherein the initiator is a […] large molecule containing a nucleophilic group selected from amino, […]; wherein the large molecule is a protein, a polypeptide or a nucleic acid, and/or […]” of claim 9;
wherein “bringing together: at least one hydrophilic polymer (Pl) comprising at least one amine function, and at least one hydrophobic a-amino acid N-carboxyanhydride monomer” (Lecommandoux, claim 1) results in an “initiator-polyamino acid conjugate” of claim 9.
It is noted that the requirements of claim 9 for “wherein the method includes adding one or more amino acid N-carboxyanhydrides in water or a mixed solution of water and an organic solvent in the presence of an initiator to react to produce an initiator-polyamino acid conjugate,” as well as the requirements of claims 21-22 for “wherein the water or the mixed solution of water and an organic solvent has a salt” and “wherein the water or the mixed solution of water and an organic solvent has a buffer salt”:
21. ([…]) The conjugate of claim 9, wherein the water or the mixed solution of water and an organic solvent has a salt; and/or wherein the amino acid is selected from natural amino acids and unnatural amino acids.
22. ([…]) The conjugate of claim 21, wherein the water or the mixed solution of water and an organic solvent has a buffer salt; and/or wherein the amino acid comprises glycine, alanine, valine, leucine, isoleucine, methionine, praline, tryptophan, serine, tyrosine, cysteine, phenylalanine, asparagine, glutamine, threonine, aspartic acid, sarcosine, glutamic acid, lysine, arginine, histidine, £-nitrogenbenzyloxycarbonyl lysine, glutamic acid benzyl ester, hydroxyproline, (S)-2-amino-4-((3-(benzylamino )-3-oxypropyl)seleno )butyric acid, penicillamine, oxy-tert-butyl-serine, £-nitrogentrifluoroacetyl L-lysine, or homocysteine or derivatives of these amino acids or a homocysteine derivative in which the sulfuydryl group in homocysteine is replaced by a selenoalkoxy group.
are product-by-process limitations. Product-by-process claims are not limited to the manipulations of the recited steps, only the structure implied by the steps. “[E]ven though product-by-process claims are limited by and defined by the process, determination of patentability is based on the product itself. The patentability of a product does not depend on its method of production. If the product in the product-by-process claim is the same as or obvious from a product of the prior art, the claim is unpatentable even though the prior product was made by a different process.” The substance and structure of the claimed “initiator-polyamino acid conjugate” of claim 9, as discussed above, is not affected by this limitation, which merely reflects one version of a process that could be used to make the product. Therefore, the product-by-process limitations of claim 9 do not add patentable weight to the claim. Nonetheless, Lecommandoux discloses claim embodiments drawn to a “‘one pot’ method for preparing an aqueous solution of nanoparticles of amphiphilic block copolymers and comprising polypeptide units,” which relates to “wherein the method includes adding one or more amino acid N-carboxyanhydrides in water” of claim 9. Further, Lecommandoux discloses claim embodiments drawn to
5. The method according to claim 1, wherein the aqueous solvent is water or a buffer.
6. The method according to claim 1, wherein the aqueous solvent also comprises a buffer solution comprising an inorganic salt at concentrations ranging from 0.01 M to 1 M.
7. The method according to claim 1, wherein the pH of the aqueous solvent is from 2 to 12.
(Lecommandoux, claims 5-6), which relates to the requirements of claims 21-22 for “wherein the water or […] has a salt” and “wherein the water or […] has a buffer salt.”
Thus, Lecommandoux anticipates claims 9 and 21-22.
Regarding claim 12 and the requirements:
12. ([…]) A pharmaceutical composition comprising the conjugate of claim 9 and a pharmaceutically acceptable carrier.
Lecommandoux discloses “[a]n aqueous composition of nanoparticles of amphiphilic block copolymers comprising polypeptide units obtained with the method according to claim 1”:
11. An aqueous composition of nanoparticles of amphiphilic block copolymers comprising polypeptide units obtained with the method according to claim 1, said nanoparticles having a core-shell structure and particle size of 2 nm to 1 μm, the weight content of said nanoparticles being at least 2% by weight relative to the weight of said aqueous composition.
(Lecommandoux, claim 11), which reads on a “pharmaceutical composition” and “pharmaceutically acceptable carrier” of claim 12.
Thus, Lecommandoux anticipates claim 12.
Regarding claim 23 and the requirements:
23. (New) The conjugate of claim 22, wherein the amino acid is selected from methionine, valine, leucine, isoleucine, praline, hydroxyproline and alanine or derivatives of these amino acids; and/or
the polyamino acid is a homopolymer or copolymer of the amino acids or a random copolymer; and/or
the protein is selected from the group consisting of enzymes, antibodies, cytokines and marker proteins; and/or
the small molecule is selected from the group consisting of benzylamine, ethylenediamine, p-methylaniline, lysine, glucosamine, p-methylthiophenol, mercaptan, doxorubicin, and gemcitabine.
Lecommandoux embodies a “Synthesis of an Amphiphilic Peptide Diblock Copolymer poly(ethylene glycol)5k-block-poly(L-leucine) and of their Corresponding Nanoparticles” (Lecommandoux, par. [0103]-[0106], Ex. 10), which reads on:
“wherein the amino acid comprises […], leucine” of claim 22, and
“wherein the amino acid is selected from […], leucine” of claim 23.
Thus, Lecommandoux anticipates claim 23.
Allowable Subject Matter
Claims 10-11 and 25 are drawn to allowable subject matter pending address of the issues pertaining to 35 U.S.C. § 112(b), discussed above.
Conclusion
Claims 9-12 and 21-25 are rejected. No claims are allowed.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to DOMINIC LAZARO whose telephone number is (571)272-2845. The examiner can normally be reached on Monday through Friday, 8:30am to 5:00pm EST; alternating Fridays out.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, BETHANY BARHAM can be reached on (571)272-6175. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/DOMINIC LAZARO/Primary Examiner, Art Unit 1611
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