# US 11,077,069 B2 · Adhesive polymer and medical adhesive patch

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- Number: US 11,077,069 B2
- Document ID: US11077069B2
- Status: Granted
- Kind: B2
- Application number: 15/764,422
- Filed: 2016-09-30
- Published: 2018-10-04
- Granted: 2021-08-03
- Earliest claimed: 2015-09-30
- Assignees: Teikoku Seiyaku Co., Ltd.; Nippon Shokubai Co., Ltd.
- Applicants: Teikoku Seiyaku Co., Ltd.; Nippon Shokubai Co., Ltd.
- Inventors: Satoshi Kawakami; Manabu Sogabe; Taiki Shibata; Yasushi Horikawa; Hiroaki Hasegawa
- Web page: https://patentgrep.com/patent/US11077069B2

## CPC

- A61K 9/7061: {Polyacrylates}
- A61K 9/0014: {Skin, i.e. galenical aspects of topical compositions (non-active ingredients are additionally classified in A61K47/00; A61K9/0009, A61K9/0021, A61K9/7015, A61K9/7023 take precedence; cosmetic preparations A61K8/00, A61Q; preparations for wound dressings or bandages A61L26/00)}
- A61K 9/7084: {Transdermal patches having a drug layer or reservoir, and one or more separate drug-free skin-adhesive layers, e.g. between drug reservoir and skin, or surrounding the drug reservoir; Liquid-filled reservoir patches}
- A61K 31/135: having aromatic rings {, e.g. ketamine, nortriptyline (methadone A61K31/137)}
- A61K 31/167: having the nitrogen of a carboxamide group directly attached to the aromatic ring, e.g. lidocaine, paracetamol
- A61K 31/18: Sulfonamides (compounds containing a para-N-benzene-sulfonyl-N- group A61K31/63)
- A61K 31/215: of carboxylic acids
- A61K 31/4045: Indole-alkylamines; Amides thereof, e.g. serotonin, melatonin
- A61K 31/4468: having a nitrogen directly attached in position 4, e.g. clebopride, fentanyl
- A61K 31/48: Ergoline derivatives, e.g. lysergic acid, ergotamine
- A61K 31/485: Morphinan derivatives, e.g. morphine, codeine
- A61K 45/00: Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K 47/32: Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers {, poly(meth)acrylates, or polyvinyl pyrrolidone}
- C08F 293/00: Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule (on to polymers modified by introduction of unsaturated end groups C08F290/02)
- C09J 7/20: characterised by their carriers
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C09J: ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES (preparation of glue or gelatine C09H)

## Abstract

The present invention provides a star-shaped acrylic block polymer having a star-shaped structure in which at least three chain polymer portions radiate from a mercapto group situated at the center, wherein (meth)acrylic acid alkyl ester structural units having 7-17 carbon atoms account for 30-99.9% by mass of whole structural units of the star-shaped acrylic block polymer, and at least one of the chain polymer portions has a copolymer structure of polymerizable monomers containing a (meth)acrylic acid alkyl ester having 7-17 carbon atoms and a weakly basic monomer; and a medical patch containing an adhesive composition containing a salt of a basic drug and the star-shaped acrylic block polymer as an adhesive that exhibits high drug efficacy, that does not cause a decrease in adhesive property of an adhesive base due to an additive, and that causes less skin irritation.

## Claims

### Claim 1

A medical patch comprising an adhesive composition comprising at least one salt of a basic drug and an adhesive,
wherein the adhesive is a star-shaped acrylic block polymer having a star-shaped structure in which at least three chain polymer portions radiate from a polyvalent mercaptan residue situated at the center, wherein (meth)acrylic acid alkyl ester structural units having 7-17 carbon atoms account for 30-99.9% by mass of whole structural units of the star-shaped acrylic block polymer, and at least one of the chain polymer portions has a structural unit having a copolymer structure of polymerizable monomers comprising at least one (meth)acrylic acid alkyl ester having 7-17 carbon atoms and at least one weakly basic monomer selected from the group consisting of dimethylaminoethyl (meth)acrylate, diethylaminoethyl (meth)acrylate, dimethylaminoethyl (meth)acrylate quaternary ammonium salt, dimethylaminopropyl acrylamide, diethylaminopropyl acrylamide, (meth)acrylamide, N-methyl(meth)acrylamide and N-propyl(meth)acrylamide;
wherein the at least one salt of the basic drug is at least one selected from the group consisting of fentanyl citrate, morphine sulfate, oxycodone hydrochloride, buprenorphine hydrochloride, oxybutynin hydrochloride, tamsulosin hydrochloride, tolterodine tartrate, rasagiline mesylate, pergolide mesylate, amantadine hydrochloride, trihexyphenidyl hydrochloride, ropinirole hydrochloride, lidocaine hydrochloride, procaine hydrochloride, donepezil hydrochloride, memantine hydrochloride, tandospirone citrate, methylphenidate hydrochloride, lurasidone hydrochloride, chlorpromazine hydrochloride, imipramine hydrochloride, asenapine maleate, salbutamol sulfate, clenbuterol hydrochloride, tulobuterol hydrochloride, procaterol hydrochloride, butorphanol tartrate, perisoxal citrate, enalapril maleate, propranolol hydrochloride, bisoprolol hydrochloride, clonidine hydrochloride, diltiazem hydrochloride, verapamil hydrochloride, isosorbide dinitrate, ketotifen fumarate, chlorpheniramine maleate, azelastine hydrochloride, diphenhydramine hydrochloride, granisetron hydrochloride, ramosetron hydrochloride, palonosetron hydrochloride and ondansetron hydrochloride; and
wherein the adhesive composition does not comprise an additive used for converting the at least one salt of the basic drug into a free base.

### Claim 2 (depends on 1)

The medical patch according to claim 1, wherein the content of the at least one weakly basic monomer relative to a non-volatile content in the adhesive is 0.1-39% by mass.

### Claim 3 (depends on 1)

The medical patch according to claim 1, wherein the content of the at least one salt of the basic drug is 0.1-50% by mass, and the content of the adhesive is 50-99.9% by mass in the adhesive composition.

### Claim 4 (depends on 1)

The medical patch according to claim 1, wherein the at least one (meth)acrylic acid alkyl ester having 7-17 carbon atoms is at least one selected from the group consisting of (meth)acrylic acid butyl ester, (meth)acrylic acid t-butyl ester, (meth)acrylic acid pentyl ester, (meth)acrylic acid hexyl ester, (meth)acrylic acid heptyl ester, (meth)acrylic acid octyl ester, (meth)acrylic acid isooctyl ester, (meth)acrylic acid nonyl ester, (meth)acrylic acid isononyl ester, (meth)acrylic acid decyl ester, (meth)acrylic acid undecyl ester, (meth)acrylic acid dodecyl ester and (meth)acrylic acid 2-ethylhexyl ester.

### Claim 5 (depends on 1)

The medical patch according to claim 1, wherein the at least one salt of the basic drug is at least one selected from the group consisting of rasagiline mesylate and asenapine maleate.

### Claim 6 (depends on 1)

The medical patch according to claim 1, wherein the at least one weakly basic monomer is selected from the group consisting of dimethylaminoethyl methacrylate and dimethylaminopropyl acrylamide.