Compounds for the treatment and/or care of the skin and/or mucous membranes and their use in cosmetic or pharmaceutical compositions

Patent metadata

Field	Value
Publication number	US-9725483-B2
Application number	US-201314391472-A
Country	US
Kind code	B2
Filing date	Apr 16, 2013
Priority date	Apr 16, 2012
Publication date	Aug 8, 2017
Grant date	Aug 8, 2017

Abstract

Compounds of general formula (I): R i —W n —X m -AA i -AA 2 -AA 3 -AA 4 -AA 5 -AA 6 -Y p —Z q —R 2 (I) their stereoisomers, mixtures thereof and/or their cosmetically or pharmaceutically acceptable salts, preparation processes, cosmetic and/or pharmaceutical compositions which contain them and their use in medicine, particularly in the treatment and/or prevention of pain, inflammation, itching, pigmentation disorders and angiogenic skin disorders, and in processes of treatment and/or care of the skin and/or mucous membranes.

First claim

The invention claimed is:

1. A compound of general formula (I),
R 1 —W n —X m -AA 1 -AA 2 -AA 3 -AA 4 -AA 5 -AA 6 -Y p —Z q —R 2   (I)

its stereoisomers, mixtures thereof and/or its cosmetically or pharmaceutically acceptable salts, wherein:
AA 1 is selected from the group consisting of -Ser- and a bond;
AA 2 is selected from the group consisting of -Val- and -Ala-;
AA 3 is selected from the group consisting of -Arg- and -Thr-;
AA 4 is -Asn-;
AA 5 is selected from the group consisting of -Ala- and -Thr-;
AA 6 is selected from the group consisting of -Val- and a bond;
W, X, Y, Z are amino acids and are independently selected from amongst themselves;
n, m, p and q are independently selected from amongst themselves and have a value of 0 or 1;
n+m+p+q is smaller than or equal to 2;
with the condition that if AA 1 is a bond, AA 2 is -Val-, AA 3 is -Thr-, AA 4 is -Asn-, and AA 6 is -Val-, then AA 5 is -Ala-;
with the condition that if AA 1 is a bond, AA 2 is -Val-, AA 3 is -Thr-, AA 4 is -Asn-, AA 5 is -Ala- and AA 6 is a bond, then n+m+p+q is equal to 0;
with the condition that if AA 1 is a bond, AA 2 is -Ala-, AA 3 is -Thr-, AA 4 is -Asn-, AA 5 is -Thr- and AA 6 is a bond, then n+m+p+q is smaller than or equal to 1;
with the condition that if AA 1 is a bond, AA 2 is -Ala-, AA 3 is -Thr-, AA 4 is -Asn-, AA 6 is a bond, X is -Gly- and W is -Leu-, then AA 5 is -Thr-;

R 1 is selected from the group consisting of H, a polymer derived from polyethylene glycol, substituted or unsubstituted non-cyclic aliphatic groups, substituted or unsubstituted alicyclyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted heteroarylalkyl, substituted or unsubstituted aryl, substituted or unsubstituted aralkyl, and R 5 —CO—, wherein R 5 is selected from the group consisting of H, substituted or unsubstituted non-cyclic aliphatic groups, substituted or unsubstituted alicyclyl, substituted or unsubstituted aryl, substituted or unsubstituted aralkyl, substituted or unsubstituted heterocyclyl, and substituted or unsubstituted heteroarylalkyl;
R 2 is selected from the group consisting of —NR 3 R 4 , —OR 3 , and —SR 3 , wherein R 3 and R 4 are independently selected from the group consisting of H, a polymer derived from polyethylene glycol, substituted or unsubstituted non-cyclic aliphatic groups, substituted or unsubstituted alicyclyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted heteroarylalkyl, substituted or unsubstituted aryl, and substituted or unsubstituted aralkyl;
at least one of:
R 1 is not H, and
R 2 is not OH; and

R 1 and R 2 are not α-amino acids.

2. The compound according to claim 1 , wherein R 1 is selected from the group consisting of H, a polymer derived from polyethylene glycol, and R 5 —CO—, wherein R 5 is selected from the group consisting of substituted or unsubstituted C 1 -C 24 alkyl radicals, substituted or unsubstituted C 2 -C 24 alkenyls, substituted or unsubstituted C 2 -C 24 alkynyls, substituted or unsubstituted C 3 -C 24 cycloalkyls, substituted or unsubstituted C 5 -C 24 cycloalkenyls, substituted or unsubstituted C 8 -C 24 cycloalkynyls, substituted or unsubstituted C 6 -C 30 aryls, substituted or unsubstituted C 7 -C 24 aralkyl, substituted or unsubstituted heterocyclyl rings of 3-10 members, and substituted or unsubstituted heteroarylalkyls of 2 to 24 carbon atoms and 1 to 3 atoms other than carbon and an alkyl chain of 1 to 6 carbon atoms, and R 5 —CO— is not an α-amino acid.

3. The compound according to claim 2 , wherein R 1 is selected from the group consisting of H, acetyl, tert-butanoyl, hexanoyl, 2-methylhexanoyl, cyclohexanecarboxyl, octanoyl, decanoyl, lauroyl, myristoyl, palmitoyl, stearoyl, oleoyl, and linoleoyl.

4. The compound according to claim 1 , wherein R 2 is selected from the group consisting of —NR 3 R 4 , —OR 3 , —SR 3 , wherein R 3 and R 4 are independently selected from the group consisting of H, a polymer derived from polyethylene glycol, substituted or unsubstituted C 1 -C 24 alkyls, substituted or unsubstituted C 2 -C 24 alkenyls, substituted or unsubstituted C 2 -C 24 alkynyls, substituted or unsubstituted C 3 -C 24 cycloalkyls, substituted or unsubstituted C 5 -C 24 cycloalkenyls, substituted or unsubstituted C 8 -C 24 cycloalkynyls, substituted or unsubstituted C 6 -C 30 aryls, substituted or unsubstituted C 7 -C 24 aralkyls, substituted or unsubstituted heterocyclyl rings of 3-10 members, and substituted or unsubstituted heteroarylalkyl of 2 to 24 carbon atoms and 1 to 3 atoms other than carbon where the alkyl chain is of 1 to 6 carbon atoms and where —NR 3 R 4 is not an α-amino acid.

5. The compound according to claim 4 , wherein R 3 and R 4 are independently selected from the group consisting of H, methyl, ethyl, hexyl, dodecyl and hexadecyl.

6. The compound according to claim 1 , wherein R 1 is selected from the group consisting of acetyl, lauroyl, myristoyl and palmitoyl.

7. A compound of general formula (I),
R 1 —W n —X m -AA 1 -AA 2 -AA 3 -AA 4 -AA 5 -AA 6 -Y p —Z q —R 2   (I)

its stereoisomers, mixtures thereof and/or its cosmetically or pharmaceutically acceptable salts, wherein:
AA 1 is a bond;
AA 2 is -Ala-;
AA 3 is -Thr-;
AA 4 -Asn-;
AA 5 is -Thr-;
AA 6 is a bond;
W, X, Y, Z are amino acids and are independently selected from amongst themselves;
n, m, p and q are independently selected from amongst themselves and have a value of 0 or 1;
n+m+p+q is smaller than or equal to 2;

R 1 is selected from the group consisting of acetyl, lauroyl, myristoyl and palmitoyl;
R 2 is selected from the group consisting of —NR 3 R 4 and —OR 3 , wherein R 3 and R 4 are independently selected from H, methyl, ethyl, hexyl, dodecyl and hexadecyl; and
R 1 and R 2 are not α-amino acids.

8. A cosmetic or pharmaceutical composition which comprises a cosmetically or pharmaceutically effective amount of at least one compound of general formula (I), its stereoisomers, mixtures thereof and/or its cosmetically or pharmaceutically acceptable salts, according to claim 1 , and at least one cosmetically or pharmaceutically acceptable excipient or adjuvant.

9. The composition according to claim 8 , wherein the compound of general formula (I), its stereoisomers, mixtures thereof and/or its cosmetically or pharmaceutically acceptable salts, is incorporated into a cosmetic or pharmaceutical delivery system or sustained release system selected from the group consisting of liposomes, mixed liposomes, oleosomes, niosomes, ethosomes, millicapsules, microcapsules, nanocapsules, nanostructured lipid carriers, sponges, cyclodextrins, vesicles, micelles, mixed micelles of surfactants, surfactant-phospholipid mixed micelles, millispheres, microspheres, nanospheres, lipospheres, microemulsions, nanoemulsions, miniparticles, milliparticles, microparticles, nanoparticles and solid lipid nanoparticles or is adsorbed on a cosmetically or pharmaceutically acceptable solid organic polymer or solid mineral support selected from the group consisting of talc, bentonite, silica, starch and maltodextrin.

10. The composition according to claim 8 , wherein the composition is present in a formulation selected from the group consisting of creams, multiple emulsions, anhydrous compositions, aqueous dispersions, oils, milks, balsams, foams, lotions, gels, cream gels, hydroalcoholic solutions, hydroglycolic solutions, hydrogels, liniments, sera, soaps, shampoos, conditioners, serums, ointments, mousses, pomades, powders, bars, pencils, sprays, aerosols, capsules, gelatin capsules, soft capsules, hard capsules, tablets, sugar coated tablets, granules, chewing gum, solutions, s

Assignees

• Lubrizol Advanced Mat Inc
• Lipotec Sa

Inventors

• García Antón José María
• Ferrer Montiel Antonio Vicente
• Carreño Serraïma Cristina
• Delgado González Raquel
• Cebrián Puche Juan

Classifications

• A61P7/02

  Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors · CPC title

• A61P9/10

  for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis · CPC title

• A61P9/00

  Drugs for disorders of the cardiovascular system · CPC title

• A61P37/02

  Immunomodulators · CPC title

• A61P43/00

  Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00 · CPC title