# US 5,710,177 A · Synergistic combinations of active substance for the cosmetic or dermatological care of the skin, hair & nails

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- Number: US 5,710,177 A
- Document ID: US5710177A
- Status: Granted
- Kind: A
- Application number: 08/448,620
- Filed: 1995-08-11
- Granted: 1998-01-20
- Earliest claimed: 1992-12-18
- Assignees: Beiersdorf AG
- Inventors: Gerhard Sauermann; Uwe Schonrock; Volker Schreiner; Franz Stab
- Web page: https://patentgrep.com/patent/US5710177A

## CPC

- A61K 8/67: Vitamins
- A61K 8/365: Hydroxycarboxylic acids; Ketocarboxylic acids
- A61P 17/00: Drugs for dermatological disorders
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A61Q 3/00: Manicure or pedicure preparations
- A61Q 5/00: Preparations for care of the hair
- A61Q 19/00: Preparations for care of the skin
- A61Q 19/08: Anti-ageing preparations
- A61K 2800/59: Mixtures
- A61Q 19/007: {Preparations for dry skin}
- 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

## Abstract

Cosmetic and/or dermatological active compound combinations comprising a) an active amount of biotin and/or biotin esters, b) an active amount of one or more .alpha.-hydroxycarboxylic acids of the formula R'(R")(OH)C COOH and/or an active amount of one or more .alpha.-ketocarboxylic acids of the formula R'C(O) COOH or their physiologically acceptable salts or esters wherein R' and R" represent H-; branched or unbranched C.sub.1-25 -alkyl- or C.sub.1-25 -alkyl-substituted by one or more carboxyl groups and/or hydroxyl groups and/or a aldehyde groups and/or oxo groups (keto groups); phenyl- or phenyl substituted by one or more carboxyl groups and/or hydroxyl groups and/or branched and/or unbranched C.sub.1-25 -alkyl groups; or wherein the .alpha.-carbon atom of the .alpha.-hydroxycarboxylic acid, together with R' and R", forms a cycloalkyl group having 3 to 7 ring atoms or the cycloalkyl substituted by one or more carboxyl groups and/or hydroxyl groups and/or oxo groups (keto groups) and/or branched and/or unbranched C.sub.1-25 -alkyl groups; and c) an active amount of one or more antioxidants.

## Claims

### Claim 1

Cosmetic and/or dermatologically active compound combinations comprising
a) an active amount of biotin and/or biotin esters,
b) an active amount of one or more .alpha.-hydroxycarboxylic acids of the general formula ##STR12## and/or an active amount of one or more .alpha.-keto-carboxylic acids of the general formula ##STR13## wherein R' and R" independently of one another are chosen from the group consisting of
(b1) H--,
(b2) branched or unbranched C.sub.1-25 -alkyl-,
(b3) branched or unbranched C.sub.1-25 -alkyl- which is substituted by one or more carboxyl groups and/or hydroxyl groups and/or aldehyde groups and/or oxo groups (keto groups),
(b4) phenyl- and
(b5) phenyl- which is substituted by one or more carboxyl groups and/or hydroxyl groups and/or branched and/or unbranched C.sub.1-25 -alkyl groups, or wherein the .alpha.-carbon atom of the .alpha.-hydroxycarboxylic acid, together with R' and R", forms a
(b6) unsubstituted cycloalkyl group having 3 to 7 ring atoms or a
(b7) cycloalkyl group having 3 to 7 ring atoms which is substituted by one or more carboxyl groups and/or hydroxyl groups and/or oxo groups (keto groups) and/or branched and/or unbranched C.sub.1-25 -alkyl groups,
and
where the .alpha.-hydroxycarboxylic acid or the .alpha.-hydroxycarboxylic acids or the .alpha.-keto-carboxylic acid or the .alpha.-keto-carboxylic acids can optionally be present in the form of their physiologically tolerated salts and/or ethyl esters and/or methyl esters,
and
c) an active amount of one or more antioxidants.

### Claim 2 (depends on 1)

Active compound combinations according to claim 1, wherein the weight ratio of biotin and/or esters thereof to the .alpha.-hydroxycarboxylic acid or acids and/or the .alpha.-keto-carboxylic acid or acids is in the range from 1:500 to 20:1.

### Claim 3 (depends on 1)

Active compound combinations according to claim 1, wherein the biotin esters are compounds of the structure: ##STR14## wherein R is H, branched or unbranched C.sub.1-18 -alkyl- or branched or unbranched C.sub.1-18 -alkenyl-.

### Claim 4 (depends on 1)

Active compound combinations according to claim 1, wherein the .alpha.-hydroxy acids are chosen from the group consisting of
(b2) .alpha.-hydroxy-fatty acids,
(b3) .alpha.-hydroxy-sugar acids or aliphatic .alpha.-hydroxy-fruit acids,
(b4) unsubstituted aromatic .alpha.-hydroxycarboxylic acids and
(b5) substituted aromatic .alpha.-hydroxycarboxylic acids.

### Claim 5 (depends on 4)

Active compound combinations according to claim 4, wherein the .alpha.-hydroxy acids are chosen from the group consisting of
(b2) .alpha.-hydroxycarboxylic acids according to the formula ##STR15## .alpha.-hydroxy-isocarboxylic acids according to the formula ##STR16## .alpha.-hydroxy-anteisocarboxylic acids according to the formula ##STR17## wherein n in each case is a number from 7 to 31, and (b3) aldonic acids, aldaric acids, uronic acids, glyceric acid, malic acid, lactic acid, hydroxy acetic acid and citric acid.

### Claim 6 (depends on 1)

Active compound combinations according to claim 1, wherein the antioxidants are chosen from the group consisting of ascorbic acid, ascorbic acid derivatives, tocopherols, tocopheryl esters and other tocopherol derivatives, folic acid, phytic acid, ubiquinones, bile extract, cis-urocanic acid, trans-urocanic acid, carnosine, histidine, flavones, flavonoids, cysteine, cysteine, cysteine derivatives, tyrosine, carotenes and lycopene (psi-carotene), .alpha.-liponic acid, glutathione, glutathione esters, zinc oxide and zinc salts. salts.

### Claim 7 (depends on 1)

Cosmetic and/or dermatological formulations comprising an active amount of an active compound combination according to claim 1.

### Claim 8 (depends on 7)

Cosmetic and/or dermatological formulations according to claim 7, wherein the active amount ranges from
0.001-0.20% by weight of biotin and/or biotin esters,
0.001-5.00% by weight of one or more .alpha.-hydroxy-carboxylic acids and/or one or more .alpha.-keto-carboxylic acids and
0.001-10.00% by weight of an antioxidant or several antioxidants.

### Claim 9 (depends on 7)

Process for the preparation of the cosmetic or dermatological formulations according to claim 7, wherein the biotin and/or biotin esters, preferably in an amount corresponding to 0.001-0.20% by weight, one or more .alpha.-hydroxycarboxylic acids and/or one or more .alpha.-keto-carboxylic acids in an amount corresponding to 0.001-5.0% by weight, and an antioxidant or several antioxidants in an amount corresponding to 0.001-5.00% by weight, in each case based on the total weight of the formulations, are incorporated into cosmetic or dermatological formulations in a known manner.

### Claim 10 (depends on 1)

A method of caring for at least one of the skin and an integumentary appendages which comprises applying thereto an amount effective therefor of a combination according to claim 1.

### Claim 11 (depends on 1)

A method of improving the appearance of dry skin which comprises applying thereto an amount effective therefor of a combination according to claim 1.

### Claim 12 (depends on 1)

A method of improving the appearance of aged skin which comprises applying thereto an amount effective therefor of a combination according to claim 1.

### Claim 13 (depends on 1)

A method of stimulating the endogenous capacity for the synthesis of skin fats or biochemical precursors thereof which comprises applying thereto an amount effective therefor of a combination according to claim 1.

### Claim 14 (depends on 1)

A method of treating the skin of a patient with the manifestation of a topic dermatitis or seborrhoeic eczema which comprises applying thereto an amount effective therefor of a combination according to claim 1.

### Claim 15 (depends on 6)

Active compounds according to claim 6, wherein the cysteine derivative is N-acetylcysteine.

### Claim 16 (depends on 6)

Active compounds according to claim 6, wherein the carotene is .beta.-carotene.