# US 9,872,842 B2 · Administration of 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphthoic acid for the treatment of dermatological disorders

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- Number: US 9,872,842 B2
- Document ID: US9872842B2
- Status: Granted
- Kind: B2
- Application number: 15/175,188
- Filed: 2016-06-07
- Published: 2016-12-15
- Granted: 2018-01-23
- Earliest claimed: 2002-03-12
- Assignees: Galderma Research & Development
- Applicants: Galderma Research & Development
- Inventors: Michael Graeber; Janusz Czernielewski
- Web page: https://patentgrep.com/patent/US9872842B2

## CPC

- A61K 31/192: having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid {(cannabinoids A61K31/658)}
- A61K 8/36: Carboxylic acids; Salts or anhydrides thereof
- A61K 8/362: Polycarboxylic acids
- A61K 8/368: with carboxyl groups directly bound to carbon atoms of aromatic rings
- 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 9/06: Ointments; Bases therefor; {Other semi-solid forms, e.g. creams, sticks, gels (composition of ointments, creams or gels A61K47/00)}
- A61K 9/08: Solutions {(composition of solutions A61K47/00)}
- A61K 31/07: Retinol compounds, e.g. vitamin A (retinoic acids A61K31/203)
- A61K 47/02: Inorganic compounds
- A61K 47/06: Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K 47/10: Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
- A61K 47/14: Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
- A61K 47/183: {Amino acids, e.g. glycine, EDTA or aspartame}
- A61K 47/22: Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones
- A61K 47/26: Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
- A61K 47/32: Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers {, poly(meth)acrylates, or polyvinyl pyrrolidone}
- A61K 47/34: Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers (A61K47/10 takes precedence)
- A61P 9/06: Antiarrhythmics
- A61P 17/00: Drugs for dermatological disorders
- A61P 17/02: for treating wounds, ulcers, burns, scars, keloids, or the like
- A61P 17/06: Antipsoriatics
- A61P 17/10: Anti-acne agents
- A61P 17/12: Keratolytics, e.g. wart or anti-corn preparations
- A61P 17/18: Antioxidants, e.g. antiradicals (preparations for protection against sunlight A61Q17/00)
- A61Q 17/04: Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
- A61Q 19/007: {Preparations for dry skin}
- A61Q 19/008: {Preparations for oily skin}
- A61K 31/203: Retinoic acids {; Salts thereof}
- A61K 47/6903: {the form being semi-solid, e.g. an ointment, a gel, a hydrogel or a solidifying gel}
- C07C 2603/74: Adamantanes
- 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)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61Q: SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

Dermatological disorders having an inflammatory or proliferative component are treated with pharmaceutical compositions containing on the order of 0.3% by weight of 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphthanoic acid (adapalene) or salt thereof, formulated into pharmaceutically acceptable media therefor, advantageously topically applicable gels, creams or lotions.

## Claims

### Claim 1

A method for eliciting an early onset of action in regression of non-inflammatory lesions in treating common acne afflicting an individual's skin, the individual being in need of such treatment, comprising topically administering daily to said individual an anti-acne effective amount of a pharmaceutical composition which consists essentially of: (1) 0.3% by weight of 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphthoic acid (adapalene) or salt thereof; (2) one or more ingredients selected from the group consisting of carbomer 940, carbomer 934, disodium edetate, methyl paraben, propylene glycol, PEG methyl glucose sesquistearate, PEG 400, methyl glucose sesquistearate, cyclomethicone, perhydrosqualene, propyl paraben, glycerol, sodium hydroxide, ethanol and phenoxyethanol; (3) water; and (4) optionally, one or more additive selected from the group consisting of wetting agents, pH regulators, osmotic pressure modifiers, emulsifiers, UV-A and UV-B screening agents and antioxidants, wherein said composition is formulated into a pharmaceutically acceptable medium therefor, said composition being a gel or a cream, said early onset of action occurring by two weeks after treatment begins and being demonstrated by regression of non-inflammatory lesions after two weeks of treatment greater than that demonstrated by vehicle alone or by a similar composition comprising 0.1% by weight of adapalene after two weeks of treatment.

### Claim 2 (depends on 1)

The method according to claim 1, wherein the common acne is of moderate to moderately severe intensity.

### Claim 3 (depends on 1)

The method according to claim 1, wherein the composition is a gel consisting essentially of adapalene, carbomer 940, disodium edetate, methyl paraben, poloxamer 124, propylene glycol, sodium hydroxide and purified water.

### Claim 4 (depends on 1)

The method according to claim 1, wherein the composition is a gel consisting essentially of adapalene, carbomer 934, disodium edetate, PEG methyl glucose sesquistearate, methyl glucose sesquistearate, glycerol, methyl paraben, cyclomethicone, perhydrosqualene, phenoxyethanol, propyl paraben, sodium hydroxide and purified water.

### Claim 5 (depends on 1)

The method according to claim 1, wherein the composition is a gel consisting essentially of adapalene, PEG 400 and ethanol.