# US 6,124,362 A · Method for regulating hair growth

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- Number: US 6,124,362 A
- Document ID: US6124362A
- Status: Granted
- Kind: A
- Application number: 09/353,408
- Filed: 1999-07-15
- Granted: 2000-09-26
- Earliest claimed: 1999-07-15
- Assignees: The Procter & Gamble Company
- Inventors: Barton James Bradbury; Shari Joy Soper; Joseph Robert Kaczvinsky, Jr.; Dorothy Limerick Bailey; Celeste Dawn Gale
- Web page: https://patentgrep.com/patent/US6124362A

## CPC

- A61K 31/19: Carboxylic acids, e.g. valproic acid (salicylic acid A61K31/60)
- A61K 8/27: Zinc; Compounds thereof
- A61K 8/37: Esters of carboxylic acids
- A61K 8/44: Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
- A61K 8/4946: {Imidazoles or their condensed derivatives, e.g. benzimidazoles}
- A61K 8/4953: {containing pyrimidine ring derivatives, e.g. minoxidil}
- A61K 8/63: Steroids; Derivatives thereof
- A61K 8/64: Proteins; Peptides; Derivatives or degradation products thereof
- A61K 8/9789: Magnoliopsida [dicotyledons]
- A61K 45/06: Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- A61P 17/14: for baldness or alopecia
- A61Q 7/00: Preparations for affecting hair growth
- A61Q 7/02: Preparations for inhibiting or slowing hair growth
- A61K 2800/782: Enzyme inhibitors; Enzyme antagonists
- 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

A method for regulating the growth and loss of hair via the use of compositions containing a compound selected from the group consisting of lupane triterpenes, derivatives of lupane triterpenes, derivatives of oleanane triterpenes, derivatives of ursane triterpenes, and salts and mixtures thereof.

## Claims

### Claim 1

A method for regulating hair growth comprising the administration to a human of a composition comprising about 0.00001% to about 99.9% of a compound selected from the group consisting of:
a) lupane triterpenes having the structure: ##STR18## Where R.sup.1 is either 1) connected to the ring system via a single bond, either .alpha.- or .beta.-configuration, and is selected from the group consisting of: H, OH, R.sup.4, OR.sup.4, OCOR.sup.4, OCOOR.sup.4, OCONHR.sup.4, or OCON(R.sup.4).sub.2 : halogen where R.sup.4 is independently selected from the group consisting of a) cyclic, straight chain or branched chain, saturated or unsaturated, substituted or unsubstituted alkyl groups containing from 1-20 carbons, where the alkyl group, if substituted, is substituted with a substituent selected from the group consisting of: i) halogens, ii) substituted or unsubstituted aryl groups comprising from 1 to 5 rings with or without heteroatoms, which heteroatoms are selected from the group consisting of nitrogen, oxygen or sulfur, where the aryl group, if substituted, is substituted with a substituent selected from the group consisting of halogens, alkyl groups, OH, OR.sup.4, OCOR.sup.4, OCOOR.sup.4, OCONHR.sup.4, or OCON(R.sup.4).sub.2 iii) OH, iv) OR.sup.4, v) OCOR.sup.4, vi) OCOOR.sup.4, vii) OCONHR.sup.4, or viii) OCON(R.sup.4).sub.2 and b) substituted or unsubstituted aryl groups comprising from 1 to 5 rings with or without heteroatoms, which heteroatoms are selected from the group consisting of nitrogen, oxygen or sulfur, where the aryl group, if substituted, is substituted with a substituent selected from the group consisting of halogens, alkyl groups, OH, OR.sup.4, OCOR.sup.4, OCOOR.sup.4, OCONHR.sup.4, or OCON(R.sup.4).sub.2), or
2) connected to the ring system via a double bond and is selected from the group consisting of a) oxygen, b) sulfur and c) R.sup.4,
Where R.sup.2 is selected from the group consisting of: CH.sub.3, CH.sub.2 OH, CH.sub.2 OR.sup.4, CHO, CO.sub.2 H, CO.sub.2 R.sup.4, COHNR.sup.4, CON(R.sup.4).sub.2, CH.sub.2 OCOR.sup.4 where R.sup.4 is independently selected from the group consisting of a) cyclic, straight chain or branched chain, saturated or unsaturated, substituted or unsubstituted alkyl groups containing from 1-20 carbons, where the alkyl group, if substituted, is substituted with a substituent selected from the group consisting of: i) halogens, ii) substituted or unsubstituted aryl groups comprising from 1 to 5 rings with or without heteroatoms, which heteroatoms are selected from the group consisting of nitrogen, oxygen or sulfur, where the aryl group, if substituted, is substituted with a substituent selected from the group consisting of halogens, alkyl groups, OH, OR.sup.4, OCOR.sup.4, OCOOR.sup.4, OCONHR.sup.4, or OCON(R.sup.4).sub.2 iii) OH, iv) OR.sup.4, v) OCOR.sup.4, vi) OCOOR.sup.4, vii) OCONHR.sup.4, or viii) OCON(R.sup.4).sub.2; and b) substituted or unsubstituted aryl groups comprising from 1 to 5 rings with or without heteroatoms, which heteroatoms are selected from the group consisting of nitrogen, oxygen or sulfur, where the aryl group, if substituted, is substituted with a substituent selected from the group consisting of halogens, alkyl groups, OH, OR.sup.4, OCOR.sup.4, OCOOR.sup.4, OCONHR.sup.4, or OCON(.sup.4).sub.2;
And where R.sup.3 is selected from the group consisting of C(CH.sub.3).dbd.CH.sub.2, CH(CH.sub.3).sub.2, COCH.sub.3, CH(OH)CH.sub.3, CH.sub.2 CH.sub.3, C(R.sup.5)(CH.sub.3)CH.sub.2 R.sup.5, or C(CH.sub.3).sub.2 R.sup.5, CH(CH.sub.3)CH.sub.2 R.sup.5, where R.sup.5 is selected from the group consisting of OH and a halogen.

### Claim 2 (depends on 1)

The method of claim 1 wherein the composition is administered via the topical application of the composition to the scalp.

### Claim 3 (depends on 2)

The method of claim 2 wherein the compound is selected from the group consisting of betulinic acid, betulonic acid and mixtures thereof.

### Claim 4 (depends on 3)

The method of claim 3 wherein the compound is betulinic acid.

### Claim 5 (depends on 3)

The method of claim 3 wherein the compound is betulonic acid.

### Claim 6 (depends on 1)

The method of claim 1 wherein the composition additionally comprises a cosmetically or pharmaceutically acceptable vehicle.

### Claim 7 (depends on 6)

The method of claim 6 wherein the cosmetically or pharmaceutically acceptable vehicle is present at a level ranging from about 50% to about 99.999% by weight of the composition.

### Claim 8 (depends on 7)

The method of claim 7 which additionally comprises a second hair growth agent selected from the group consisting of zinc salts of carboxylic acids, saponins, other triterpenes such as oleanolic acid and ursolic acid, crataegolic acid, celastrol, asiatic acid, inhibitors of 5-.alpha.-reductase such as progesterone, 1,4-methyl-4-azasteroids, in particular 17-.beta.-N,N-diethylcarbamoyl-4-methyl-4-aza-5-.alpha.-androstan-3-one, androgen receptor antagonists such as cyproterone acetate, Minoxidil.RTM., azelaic acid and its derivatives, cyclosporin, triiodothyronine, diazoxide, potassium channel openers such as cromakalin, phenytoin and mixtures thereof.

### Claim 9 (depends on 2)

The method of claim 2 wherein the composition is applied to the scalp where the hair is bald or balding.

### Claim 10 (depends on 9)

The method of claim 9 wherein the composition is topically applied from 1 to about 10 times per day.