# US 2008/0188558 A1 · Treatment of Acne Using Derivatives of 5-Aminolevulinic Acid

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- Number: US 2008/0188558 A1
- Document ID: US20080188558A1
- Status: Published application
- Kind: A1
- Application number: 11/667,504
- Filed: 2005-11-04
- Published: 2008-08-07
- Earliest claimed: 2004-11-10
- Inventors: Aslak Godal; Jo Klaveness; Hilde Morris
- Web page: https://patentgrep.com/patent/US20080188558A1

## CPC

- A61N 5/0616: {Skin treatment other than tanning}
- A61K 31/197: the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid or pantothenic acid (carnitine A61K31/205)
- A61K 41/0061: {5-aminolevulinic acid-based PDT: 5-ALA-PDT involving porphyrins or precursors of protoporphyrins generated in vivo from 5-ALA}
- A61P 17/00: Drugs for dermatological disorders
- A61P 17/10: Anti-acne agents
- A61N: ELECTROTHERAPY; MAGNETOTHERAPY; RADIATION THERAPY; ULTRASOUND THERAPY (measurement of bioelectric currents A61B; surgical instruments, devices or methods for transferring non-mechanical forms of energy to or from the body A61B18/00; anaesthetic apparatus in general A61M; incandescent lamps H01K; infrared radiators for heating H05B)
- 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

## Abstract

The invention provides use of a photosensitiser, which is a derivative (e.g. an ester) of 5-aminolevulinic acid (5-ALA) or a pharmaceutically acceptable salt thereof, in the manufacture of a medicament for use in the prevention or treatment of acne.

## Claims

### Claim 1

A method of preventing or treating acne comprising administering to an area of skin on a body a photosensitiser which is a derivative of 5-aminolevulinic acid (5-ALA), or a pharmaceutically acceptable salt thereof, and photoactivating said photosensitiser, wherein said photosensitiser is a compound of general formula I:
R22N—CH2COCH2—CH2CO—OR1 (I)
(wherein
R1 represents an unsubstituted alkyl group or an alkyl group substituted by an aryl group; and each R2 independently represents a hydrogen atom or an optionally substituted alkyl group).

### Claim 2 (depends on 1)

The method of claim 1, wherein in formula I each R2 represents a hydrogen atom.

### Claim 3 (depends on 1)

The method of claim 1, wherein in formula 1, R1 represents a C1-2 alkyl group optionally substituted by an aryl group.

### Claim 4 (depends on 3)

The method of claim 3, wherein said compound is selected from methyl ALA ester, benzyl ALA ester or substituted benzyl ALA ester.

### Claim 5 (depends on 1)

The method of claim 1, wherein in formula 1, R1 represents an alkyl group substituted by an aryl group.

### Claim 6 (depends on 1)

The method of claim 1, wherein in formula 1, R1 represents an aryl substituted C1-4 alkyl group wherein said aryl group is itself optionally substituted, and each R2 is as defined in claim 1.

### Claim 7 (depends on 6)

The method of claim 6, wherein said compound is selected from the group consisting of benzyl ALA ester, 4-isopropylbenzyl ALA ester, 4-methylbenzyl ALA ester, 2-methylbenzyl ALA ester, 3-methylbenzyl ALA ester, 4-[t-butyl]benzyl ALA ester, 4-[trifluoromethyl]benzyl ALA ester, 4-methoxybenzyl ALA ester, 3,4-[di-chloro]benzyl ALA ester, 4-chlorobenzyl ALA ester, 4-fluorobenzyl ALA ester, 2-fluorobenzyl ALA ester, 3-fluorobenzyl ALA ester, 2,3,4,5,6-pentafluorobenzyl ALA ester, 3-nitrobenzyl ALA ester, 4-nitrobenzyl ALA ester, 2-phenylethyl ALA ester, 4-phenylbutyl ALA ester, 3-pyridinyl-methyl ALA ester, 4-diphenyl-methyl ALA ester and benzyl-5-[(1-acetyloxyethoxy)-carbonyl]amino levulinate.

### Claim 8 (depends on 5)

The method of claim 5, wherein said compound is selected from benzyl ALA ester or substituted benzyl ALA ester.

### Claim 9 (depends on 1)

The method of claim 1, wherein in formula 1, R1 represents an unsubstituted alkyl group.

### Claim 10 (depends on 9)

The method of claim 9, wherein said compound is selected from methyl ALA ester, ethyl ALA ester, propyl ALA ester, butyl ALA ester, pentyl ALA ester, hexyl ALA ester, octyl ALA ester, 2-methylpentyl ALA ester, 4-methylpentyl ALA ester, 1-ethylbutyl ALA ester, 3,3-dimethyl-1-butyl ALA ester.

### Claim 11 (depends on 9)

The method of claim 9, wherein said compound is selected from methyl ALA ester, hexyl ALA ester and 4-methylpentyl ALA ester.

### Claim 12 (depends on 1)

The method of claim 1, wherein said acne is associated with Propionibacterium acnes, Propionibacterium avidum or Propionibacterium granulosum.

### Claim 13 (depends on 1)

The method of claim 1, wherein said acne is selected from acne vulgaris, acne rosacea, acne conglobate, acne papulosa and premenstrual acne.

### Claim 14 (depends on 1)

The method of claim 1, wherein the photosensitiser is administered together with a second photosensitiser, and the photosensitisers are photoactivated.

### Claim 15 (depends on 1)

A kit or pack containing a photosensitiser as defined in claim 1, or a pharmaceutically acceptable salt thereof, and separately a second photosensitiser for simultaneous, separate or sequential use in a method of treating or preventing acne.

### Claim 16 (depends on 1)

The method of claim 1, wherein the photosensitiser, or a pharmaceutically acceptable salt thereof, is administered together with at least one surface-penetration assisting agent, and optionally one or more chelating agents.

### Claim 17 (depends on 1)

The method of claim 1, wherein the photosensitiser, or a pharmaceutically acceptable salt thereof, is administered together with a non-photosensitising acne treatment agent.

### Claim 18 (depends on 1)

A product or kit for use in a method of treating or preventing acne comprising:
(a) a first container containing a photosensitiser as defined in claim 1, or a pharmaceutically acceptable salt thereof; and
(b) a second container containing a non-photosensitising acne treatment agent.

### Claim 19 (depends on 1)

The method of claim 1, wherein the method is the cosmetic treatment of acne.

### Claim 20

(canceled)

### Claim 21 (depends on 1)

The method of claim 1, optionally entailing the step of waiting for a time period necessary for the photosensitiser to achieve an effective tissue concentration at the desired site prior to photoactivating the photosensitiser at the desired site.

### Claim 22 (depends on 1)

The method of claim 1, wherein R1 represents an unsubstituted C1-8 alkyl.

### Claim 23 (depends on 1)

The method of claim 1, wherein R1 represents a C1-2 alkyl substituted by an aryl group.

### Claim 24 (depends on 3)

The method of claim 3, wherein R1 represents a C1 alkyl group optionally substituted by an aryl group.

### Claim 25 (depends on 5)

The method of claim 5, wherein R1 represents C1 or C2 alkyl substituted by a phenyl group.

### Claim 26 (depends on 6)

The method of claim 6, wherein R1 represents an aryl substituted C1 or C2 alkyl group, wherein said aryl group comprises up to 20 carbon atoms, and each R2 is hydrogen.

### Claim 27 (depends on 8)

The method of claim 8, wherein said compound is selected from benzyl ALA ester, 4-nitrobenzyl ALA ester, and 4-chlorobenzyl ALA ester.

### Claim 28 (depends on 9)

The method of claim 9, wherein in formula 1, R1 represents an unsubstituted C1-8 alkyl.

### Claim 29 (depends on 11)

The method of claim 11, wherein said compound is methyl ALA ester.

### Claim 30 (depends on 13)

The method of claim 13, wherein said acne is acne vulgaris.

### Claim 31 (depends on 19)

The method of claim 19, wherein the acne is on the face.