US2003139471A1PendingUtilityA1
Compositions which contain triterpenes for regulating hair growth
Assignee: UNIV TEXAS SOUTHWESTERN MED CTPriority: Jul 17, 1998Filed: Nov 18, 2002Published: Jul 24, 2003
Est. expiryJul 17, 2018(expired)· nominal 20-yr term from priority
A61K 31/506A61K 45/06A61K 31/65A61K 8/63A61Q 7/00
54
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Claims
Abstract
The present invention relates to compositions containing i) from about 0.0001% to about 99.9% of certain compounds 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, and ii) a vehicle.
Claims
exact text as granted — not AI-modifiedWhat is claimed is:
1 . A composition which comprises:
a) a pharmaceutically or cosmetically acceptable vehicle; and b) from about 0.00001% to about 99.9% of a lupane triterpene having the structure: Where R 1 is connected to the ring system via a single bond, α-configuration, and is selected from the group consisting of H and OH; Where R 2 is selected from the group consisting of: CH 3 , CH 2 OH, CH 2 OR 4 , CHO, CO 2 H, CO 2 R 4 , COHNR 4 , CON(R 4 ) 2 , and CH 2 OCOR 4 , where R 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 and sulfur, where the aryl group, if substituted, is substituted with a substituent selected from the group consisting of halogens, alkyl groups, OH, OR 4 , OCOR 4 , OCOOR 4 , OCONHR 4 , and OCON(R 4 ) 2 , iii) OH, iv)OR 4 , v) OCOR 4 , vi) OCOOR 4 , vii) OCONHR 4 , and viii) OCON(R 4 ) 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 and sulfur, where the aryl group, if substituted, is substituted with a substituent selected from the group consisting of halogens, alkyl groups, OH, OR 4 , OCOR 4 , OCOOR 4 , OCONHR 4 , and OCON(R 4 ) 2 ; And where R 3 is selected from the group consisting of COCH 3 , CH(OH)CH 3 , C(R 5 )(CH 3 )CH 2 R 5 , C(CH 3 ) 2 R 5 , and CH(CH 3 )CH 2 R 5 , where R 5 is selected from the group consisting of OH and a halogen, wherein the compound is not comprised solely of betulinic acid.
2 . A composition which comprises:
a) a pharmaceutically or cosmetically acceptable vehicle; and b) from about 0.00001% to about 99.9% of a lupane triterpene having the structure: Where R 1 is connected to the ring system via a single bond, α-configuration, and is selected from the group consisting of H and OH, Where R 2 is selected from the group consisting of: CH 3 , CH 2 OR 4 , COHNR 4 , CON(R 4 ) 2 , and CH 2 OCOR 4 , where R 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 and sulfur, where the aryl group, if substituted, is substituted with a substituent selected from the group consisting of halogens, alkyl groups, OH, OR 4 , OCOR 4 , OCOOR 4 , OCONHR 4 , and OCON(R 4 ) 2 iii) OH, iv) OR 4 , v) OCOR 4 , vi) OCOOR 4 , vii) OCONHR 4 , and viii) OCON(R 4 ) 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 and sulfur, where the aryl group, if substituted, is substituted with a substituent selected from the group consisting of halogens, alkyl groups, OH, OR 4 , OCOR 4 , OCOOR 4 , OCONHR 4 , and OCON(R 4 ) 2 ; And where R 3 is selected from the group consisting of C(CH 3 )═CH 2 , CH(CH 3 ) 2 , COCH 3 , CH(OH)CH 3 , CH 2 CH 3 , C(R 5 )(CH 3 )CH 2 R 5 , and C(CH 3 ) 2 R 5 , CH(CH 3 )CH 2 R 5 , where R 5 is selected from the group consisting of OH and a halogen, wherein the compound is not comprised solely of betulinic acid.
3 . A composition which comprises:
a) a pharmaceutically or cosmetically acceptable vehicle; and b) from about 0.00001% to about 99.9% of a lupane triterpene having the structure: Where R 1 is connected to the ring system via a single bond, α-configuration, and is selected from the group consisting of: R 4 , OR 4 , OCOR 4 , OCOOR 4 , OCONHR 4 , and OCON(R 4 ) 2 , where R 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 and sulfur, where the aryl group, if substituted, is substituted with a substituent selected from the group consisting of halogens, alkyl groups, OH, OR 4 , OCOR 4 , OCOOR 4 , OCONHR 4 , and OCON(R 4 ) 2 iii) OH, iv) OR 4 , v) OCOR 4 , vi) OCOOR 4 , vii) OCONHR 4 , and viii) OCON(R 4 ) 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 and sulfur, where the aryl group, if substituted, is substituted with a substituent selected from the group consisting of halogens, alkyl groups, OH, OR 4 , OCOR 4 , OCOOR 4 , OCONHR 4 , and OCON(R 4 ) 2 ), and Where R 2 is selected from the group consisting of: CH 3 , CH 2 OH, CH 2 OR 4 , CHO, CO 2 H, CO 2 R 4 , COHNR 4 , CON(R 4 ) 2 , and CH 2 OCOR 4 , where R 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 and sulfur, where the aryl group, if substituted, is substituted with a substituent selected from the group consisting of halogens, alkyl groups, OH, OR 4 , OCOR 4 , OCOOR 4 , OCONHR 4 , and OCON(R 4 ) 2 iii) OH, iv) OR 4 , v) OCOR 4 , vi) OCOOR 4 , vii) OCONHR 4 , and viii) OCON(R 4 ) 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 and sulfur, where the aryl group, if substituted, is substituted with a substituent selected from the group consisting of halogens, alkyl groups, OH, OR 4 , OCOR 4 , OCOOR 4 , OCONHR 4 , and OCON(R 4 ) 2 ; And where R 3 is selected from the group consisting of C(CH 3 )═CH 2 , CH(CH 3 ) 2 , COCH 3 , CH(OH)CH 3 , CH 2 CH 3 , C(R 5 )(CH 3 )CH 2 R 5 , and C(CH 3 ) 2 R 5 , CH(CH 3 )CH 2 R 5 , where R 5 is selected from the group consisting of OH and a halogen.
4 . A composition which comprises:
a) a pharmaceutically or cosmetically acceptable vehicle; and b) from about 0.00001% to about 99.9% of a lupane triterpene having the structure: Where R 1 is connected to the ring system via a single bond, β-configuration, and is selected from the group consisting of: R 4 , OCOOR 4 , OCONHR 4 , and OCON(R 4 ) 2 , where R 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 and sulfur, where the aryl group, if substituted, is substituted with a substituent selected from the group consisting of halogens, alkyl groups, OH, OR 4 , OCOR 4 , OCOOR 4 , OCONHR 4 , and OCON(R 4 ) 2 iii) OH, iv) OR 4 , v) OCOR 4 , vi) OCOOR 4 , vii) OCONHR 4 , or viii) OCON(R 4 ) 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 and sulfur, where the aryl group, if substituted, is substituted with a substituent selected from the group consisting of halogens, alkyl groups, OH, OR 4 , OCOR 4 , OCOOR 4 , OCONHR 4 , and OCON(R 4 ) 2 ), Where R 2 is selected from the group consisting of: CH 3 , CH 2 OH, CH 2 OR 4 , CHO, CO 2 H, CO 2 R 4 , COHNR 4 , CON(R 4 ) 2 , and CH 2 OCOR 4 , where R 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 and sulfur, where the aryl group, if substituted, is substituted with a substituent selected from the group consisting of halogens, alkyl groups, OH, OR 4 , OCOR 4 , OCOOR 4 , OCONHR 4 , and OCON(R 4 ) 2 iii) OH, iv) OR 4 , v) OCOR 4 , vi) OCOOR 4 , vii) OCONHR 4 , and viii) OCON(R 4 ) 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 and sulfur, where the aryl group, if substituted, is substituted with a substituent selected from the group consisting of halogens, alkyl groups, OH, OR 4 , OCOR 4 , IS OCOOR 4 , OCONHR 4 , and OCON(R 4 ) 2 ; And where R 3 is selected from the group consisting of C(CH 3 )═CH 2 , CH(CH 3 ) 2 , COCH 3 , CH(OH)CH 3 , CH 2 CH 3 , C(R 5 )(CH 3 )CH 2 R 5 , and C(CH 3 ) 2 R 5 , CH(CH 3 )CH 2 R 5 , where R 5 is selected from the group consisting of OH and a halogen.
5 . A composition which comprises:
a) a pharmaceutically or cosmetically acceptable vehicle; and b) from about 0.00001% to about 99.9% of a lupane triterpene having the structure: Where R 1 is connected to the ring system via a single bond, β-configuration, and where R1 is H Where R 2 is selected from the group consisting of: CH 3 , CH 2 OH, CH 2 OR 4 , CHO, CO 2 H, CO 2 R 4 , COHNR 4 , CON(R 4 ) 2 , and CH 2 OCOR 4 , where R 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 and sulfur, where the aryl group, if substituted, is substituted with a substituent selected from the group consisting of halogens, alkyl groups, OH, OR 4 , OCOR 4 , OCOOR 4 , OCONHR 4 , and OCON(R 4 ) 2 iii) OH, iv) OR 4 , v) OCOR 4 , vi) OCOOR 4 , vii) OCONHR 4 , and viii) OCON(R 4 ) 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 and sulfur, where the aryl group, if substituted, is substituted with a substituent selected from the group consisting of halogens, alkyl groups, OH, OR 4 , OCOR 4 , OCOOR 4 , OCONHR 4 , and OCON(R 4 ) 2 ; And where R 3 is selected from the group consisting of COCH 3 , CH(OH)CH 3 , C(R 5 )(CH 3 )CH 2 R 5 , C(CH 3 ) 2 R 5 , and CH(CH 3 )CH 2 R 5 , where R 5 is selected from the group consisting of OH and a halogen.
6 . A composition which comprises:
a) a pharmaceutically or cosmetically acceptable vehicle; and b) from about 0.00001% to about 99.9% of a lupane triterpene having the structure: Where R 1 is connected to the ring system via a single bond, β-configuration, and where R 1 is H; Where R 2 is selected from the group consisting of: CH 3 , CH 2 OR 4 , COHNR 4 , CON(R 4 ) 2 , and CH 2 OCOR 4 , where R 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 and sulfur, where the aryl group, if substituted, is substituted with a substituent selected from the group consisting of halogens, alkyl groups, OH, OR 4 , OCOR 4 , OCOOR 4 , OCONHR 4 , and OCON(R 4 ) 2 iii) OH, iv), OR 4 , v) OCOR 4 , vi) OCOOR 4 , vii) OCONHR 4 , and viii) OCON(R 4 ) 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 and sulfur, where the aryl group, if substituted, is substituted with a substituent selected from the group consisting of halogens, alkyl groups, OH, OR 4 , OCOR 4 , OCOOR 4 , OCONHR 4 , and OCON(R 4 ) 2 ; And where R 3 is selected from the group consisting of C(CH 3 )═CH 2 , CH(CH 3 ) 2 , COCH 3 , CH(OH)CH 3 , CH 2 CH 3 , C(R 5 )(CH 3 )CH 2 R 5 , and C(CH 3 ) 2 R 5 , CH(CH 3 )CH 2 R 5 , where R 5 is selected from the group consisting of OH and a halogen.
7 . A composition which comprises:
a) a pharmaceutically or cosmetically acceptable vehicle; and b) from about 0.00001% to about 99.9% of lupane triterpene having the structure: Where R 1 is connected to the ring system via a single bond, β-configuration, and where R 1 is OH; Where R 2 is selected from the group consisting of: CH 3 , CH 2 OH, CH 2 OR 4 , CHO, CO 2 H, CO 2 R 4 , COHNR 4 , CON(R 4 ) 2 , and CH 2 OCOR 4 where R 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 and sulfur, where the aryl group, if substituted, is substituted with a substituent selected from the group consisting of halogens, alkyl groups, OH, OR 4 , OCOR 4 , OCOOR 4 , OCONHR 4 , and OCON(R 4 ) 2 iii) OH, iv) OR 4 , v) OCOR 4 , vi) OCOOR 4 , vii) OCONHR 4 , and viii) OCON(R 4 ) 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 and sulfur, where the aryl group, if substituted, is substituted with a substituent selected from the group consisting of halogens, alkyl groups, OH, OR 4 , OCOR 4 , OCOOR 4 , OCONHR 4 , and OCON(R 4 ) 2 ; And where R 3 is selected from the group consisting of COCH 3 , CH(OH)CH 3 , C(R 5 )(CH 3 )CH 2 R 5 , and C(CH 3 ) 2 R 5 , where R 5 is a halogen, wherein the compound is not comprised solely of betulinic acid.
8 . A composition which comprises:
a) a pharmaceutically or cosmetically acceptable vehicle; and b) from about 0.00001% to about 99.9% of lupane triterpene having the structure: Where R 1 is connected to the ring system via a single bond, β-configuration, and where R 1 is OH; Where R 2 is selected from the group consisting of CH 2 OR 4 , COHNR 4 , and CON(R 4 ) 2 , where R 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 and sulfur, where the aryl group, if substituted, is substituted with a substituent selected from the group consisting of halogens, alkyl groups, OH, OR 4 , OCOR 4 , OCOOR 4 , OCONHR 4 , and OCON(R 4 ) 2 iii) OH, iv) OR 4 , v) OCOR 4 , vi) OCOOR 4 , vii) OCONHR 4 , or viii) OCON(R 4 ) 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 and sulfur, where the aryl group, if substituted, is substituted with a substituent selected from the group consisting of halogens, alkyl groups, OH, OR 4 , OCOR 4 , OCOOR 4 , OCONHR 4 , and OCON(R 4 ) 2 ; And where R 3 is C(CH 3 )═CH 2 .
9 . A composition which comprises:
a) a pharmaceutically or cosmetically acceptable vehicle; and b) from about 0.00001% to about 99.9% of a lupane triterpene having the structure: Where R 1 is connected to the ring system via a single bond, β-configuration, and where R1 is OH; Where R 2 is selected from the group consisting of: CH 3 , CH 2 OR 4 , COHNR 4 , CON(R 4 ) 2 , and CH 2 OCOR 4 where R 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 and sulfur, where the aryl group, if substituted, is substituted with a substituent selected from the group consisting of halogens, alkyl groups, OH, OR 4 , OCOR 4 , OCOOR 4 , OCONHR 4 , and OCON(R 4 ) 2 iii) OH, iv) OR 4 , v) OCOR 4 , vi) OCOOR 4 , vii) OCONHR 4 , and viii) OCON(R 4 ) 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 and sulfur, where the aryl group, if substituted, is substituted with a substituent selected from the group consisting of halogens, alkyl groups, OH, OR 4 , OCOR 4 , OCOOR 4 , OCONHR 4 , and OCON(R 4 ) 2 ; And where R 3 is selected from the group consisting of CH(CH 3 ) 2 and CH 2 CH 3 .
10 . A composition which comprises:
a) a pharmaceutically or cosmetically acceptable vehicle; and b) from about 0.00001% to about 99.9% of a lupane triterpene having the structure: Where R 1 is connected to the ring system via a single bond, β-configuration, and where R 1 is OH; Where R 2 is selected from the group consisting of: CH 3 , CH 2 OR 4 , CHO, CO 2 H, CO 2 R 4 , COHNR 4 , CON(R 4 ) 2 , and CH 2 OCOR 4 , where R 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 and sulfur, where the aryl group, if substituted, is substituted with a substituent selected from the group consisting of halogens, alkyl groups, OH, OR 4 , OCOR 4 , OCOOR 4 , OCONHR 4 , or OCON(R 4 ) 2 iii) OH, iv) OR 4 , v) OCOR 4 , vi) OCOOR 4 , vii) OCONHR 4 , and viii) OCON(R 4 ) 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 and sulfur, where the aryl group, if substituted, is substituted with a substituent selected from the group consisting of halogens, alkyl groups, OH, OR 4 , OCOR 4 , OCOOR 4 , OCONHR 4 , and OCON(R 4 ) 2 ; And where R 3 is CH(CH 3 )CH 2 R 5 , where R 5 is selected from the group consisting of OH and a halogen, wherein the compound is not comprised solely of betulinic acid.
11 . A composition which comprises:
a) a pharmaceutically or cosmetically acceptable vehicle; and b) from about 0.00001% to about 99.9% of a lupane triterpene having the structure: Where R 1 is connected to the ring system via a single bond, β-configuration, and where R 1 is OH, Where R 2 is selected from the group consisting of: CH 3 , CH 2 OH, CH 2 OR 4 , CHO, CO 2 H, CO 2 R 4 , COHNR 4 , CON(R 4 ) 2 , and CH 2 OCOR 4 where R 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 and sulfur, where the aryl group, if substituted, is substituted with a substituent selected from the group consisting of halogens, alkyl groups, OH, OR 4 , OCOR 4 , OCOOR 4 , OCONHR 4 , and OCON(R 4 ) 2 iii) OH, iv) OR 4 , v) OCOR 4 , vi) OCOOR 4 , vii) OCONHR 4 , and viii) OCON(R 4 ) 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 and sulfur, where the aryl group, if substituted, is substituted with a substituent selected from the group consisting of halogens, alkyl groups, OH, OR 4 , OCOR 4 , OCOOR 4 , OCONHR 4 , and OCON(R 4 ) 2 ; And where R 3 is selected from the group consisting of COCH 3 , CH(OH)CH 3 , and C(R 5 )(CH 3 )CH 2 R 5 , where R 5 is OH, wherein the compound is not comprised solely of betulinic acid.
12 . A composition which comprises:
a) a pharmaceutically or cosmetically acceptable vehicle; and b) from about 0.00001% to about 99.9% of a lupane triterpene having the structure: Where R 1 is connected to the ring system via a single bond, β-configuration, and where R 1 is OH, Where R 2 is selected from the group consisting of: CH 2 OH, CH 2 OR 4 , CHO, CO 2 H, CO 2 R 4 , COHNR 4 , CON(R 4 ) 2 , and CH 2 OCOR 4 where R 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 and sulfur, where the aryl group, if substituted, is substituted with a substituent selected from the group consisting of halogens, alkyl groups, OH, OR 4 , OCOR 4 , OCOOR 4 , OCONHR 4 , and OCON(R 4 ) 2 iii) OH, iv) OR 4 , v) OCOR 4 , vi) OCOOR 4 , vii) OCONHR 4 , and viii) OCON(R 4 ) 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 and sulfur, where the aryl group, if substituted, is substituted with a substituent selected from the group consisting of halogens, alkyl groups, OH, OR 4 , OCOR 4 , OCOOR 4 , OCONHR 4 , and OCON(R 4 ) 2 ; And where R 3 is C(CH 3 ) 2 R 5 , where R 5 is OH, wherein the compound is not comprised solely of betulinic acid.
13 . A composition which comprises:
a) a pharmaceutically or cosmetically acceptable vehicle; and b) from about 0.00001% to about 99.9% of a lupane triterpene having the structure: Where R 1 is connected to the ring system via a single bond, β-configuration, and where R 1 is OR 4 , where R 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 and sulfur, where the aryl group, if substituted, is substituted with a substituent selected from the group consisting of halogens, alkyl groups, OH, OR 4 , OCOR 4 , OCOOR 4 , OCONHR 4 , and OCON(R 4 ) 2 iii) OH, iv) OR 4 , v) OCOR 4 , vi) OCOOR 4 , vii) OCONHR 4 , and viii) OCON(R 4 ) 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 and sulfur, where the aryl group, if substituted, is substituted with a substituent selected from the group consisting of halogens, alkyl groups, OH, OR 4 , OCOR 4 , OCOOR 4 , OCONHR 4 , and OCON(R 4 ) 2 ), Where R 2 is selected from the group consisting of: CH 3 , CH 2 OH, CH 2 OR 4 , CHO, COHNR 4 , CON(R 4 ) 2 , and CH 2 OCOR 4 where R 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 and sulfur, where the aryl group, if substituted, is substituted with a substituent selected from the group consisting of halogens, alkyl groups, OH, OR 4 , OCOR 4 , OCOOR 4 , OCONHR 4 , and OCON(R 4 ) 2 iii) OH, iv) OR 4 , v) OCOR 4 , vi) OCOOR 4 , vii) OCONHR 4 , or viii) OCON(R 4 ) 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 and sulfur, where the aryl group, if substituted, is substituted with a substituent selected from the group consisting of halogens, alkyl groups, OH, OR 4 , OCOR 4 , OCOOR 4 , OCONHR 4 , and OCON(R 4 ) 2 ; And where R 3 is selected from the group consisting of C(CH 3 )═CH 2 , CH(CH 3 ) 2 , COCH 3 , CH(OH)CH 3 , CH 2 CH 3 , C(R 5 )(CH 3 )CH 2 R 5 , C(CH 3 ) 2 R 5 , and CH(CH 3 )CH 2 R 5 , where R 5 is selected from the group consisting of OH and a halogen.
14 . A composition which comprises:
a) a pharmaceutically or cosmetically acceptable vehicle; and b) from about 0.00001% to about 99.9% of a lupane triterpenes having the structure: Where R 1 is connected to the ring system via a single bond, β-configuration, and where R 1 is OCOR 4 ; Where R 2 is selected from the group consisting of: CH 3 , CH 2 OH, and CH 2 OCOR 4 , where R 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 and sulfur, where the aryl group, if substituted, is substituted with a substituent selected from the group consisting of halogens, alkyl groups, OH, OR 4 , OCOR 4 , OCOOR 4 , OCONHR 4 , and OCON(R 4 ) 2 iii) OH, iv) OR 4 , v) OCOR 4 , vi) OCOOR 4 , vii) OCONHR 4 , and viii) OCON(R 4 ) 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 and sulfur, where the aryl group, if substituted, is substituted with a substituent selected from the group consisting of halogens, alkyl groups, OH, OR 4 , OCOR 4 , OCOOR 4 , OCONHR 4 , and OCON(R 4 ) 2 ; And where R 3 is selected from the group consisting of CH(CH 3 ) 2 , COCH 3 , CH(OH)CH 3 , CH 2 CH 3 , C(R 5 )(CH 3 )CH 2 R 5 , C(CH 3 ) 2 R 5 , and CH(CH 3 )CH 2 R 5 , where R 5 is selected from the group consisting of OH and a halogen.
15 . A composition which comprises:
a) a pharmaceutically or cosmetically acceptable vehicle; and b) from about 0.00001% to about 99.9% of a lupane triterpene having the structure: Where R 1 is connected to the ring system via a single bond, β-configuration, and where R 1 is OCOR 4 , where R 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 and sulfur, where the aryl group, if substituted, is substituted with a substituent selected from the group consisting of halogens, alkyl groups, OH, OR 4 , OCOR 4 , OCOOR 4 , OCONHR 4 , and OCON(R 4 ) 2 iii) OH, iv) OR 4 , v) OCOR 4 , vi) OCOOR 4 , vii) OCONHR 4 , and viii) OCON(R 4 ) 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 and sulfur, where the aryl group, if substituted, is substituted with a substituent selected from the group consisting of halogens, alkyl groups, OH, OR 4 , OCOR 4 , OCOOR 4 , OCONHR 4 , and OCON(R 4 ) 2 ), Where R 2 is selected from the group consisting of: CHO, COHNR 4 , CON(R 4 ) 2 , and CH 2 OR 4 , where R 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 and sulfur, where the aryl group, if substituted, is substituted with a substituent selected from the group consisting of halogens, alkyl groups, OH, OR 4 , OCOR 4 , OCOOR 4 , OCONHR 4 , and OCON(R 4 ) 2 iii) OH, iv) OR 4 , v) OCOR 4 , vi) OCOOR 4 , vii) OCONHR 4 , and viii) OCON(R 4 ) 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 and sulfur, where the aryl group, if substituted, is substituted with a substituent selected from the group consisting of halogens, alkyl groups, OH, OR 4 , OCOR 4 , OCOOR 4 , OCONHR 4 , and OCON(R 4 ) 2 ; And where R 3 is selected from the group consisting of C(CH 3 )═CH 2 , CH(CH 3 ) 2 , COCH 3 , CH(OH)CH 3 , CH 2 CH 3 , C(R 5 )(CH 3 )CH 2 R 5 , C(CH 3 ) 2 R 5 , and CH(CH 3 )CH 2 R 5 , where R 5 is selected from the group consisting of OH and a halogen.
16 . A composition which comprises:
a) a pharmaceutically or cosmetically acceptable vehicle; and b) from about 0.00001% to about 99.9% of a lupane triterpene having the structure: Where R 1 is connected to the ring system via a double bond and is selected from the group consisting of sulfur and R 4 , Where R 2 is selected from the group consisting of: CH 3 , CH 2 OH, CH 2 OR 4 , CHO, CO 2 H, CO 2 R 4 , COHNR 4 , CON(R 4 ) 2 , and CH 2 OCOR 4 , where R 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 and sulfur, where the aryl so group, if substituted, is substitured with a substituent selected from the group consisting of halogens, alkyl groups, OH, OR 4 , OCOR 4 , OCOOR 4 , OCONHR 4 , and OCON(R 4 ) 2 iii) OH, iv) OR 4 , v) OCOR 4 , vi) OCOOR 4 , vii) OCONHR 4 , and viii) OCON(R 4 ) 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 and sulfur, where the aryl group, if substituted, is substituted with a substituent selected from the group consisting of halogens, alkyl groups, OH, OR 4 , OCOR 4 , OCOOR 4 , OCONHR 4 , and OCON(R 4 ) 2 ; And where R 3 is selected from the group consisting of C(CH 3 )═CH 2 , CH(CH 3 ) 2 , COCH 3 , CH(OH)CH 3 , CH 2 CH 3 , C(R 5 )(CH 3 )CH 2 R 5 , C(CH 3 ) 2 R 5 , and CH(CH 3 )CH 2 R 5 , where R 5 is selected from the group consisting of OH and a halogen.
17 . A composition which comprises:
a) a pharmaceutically or cosmetically acceptable vehicle; and b) from about 0.00001% to about 99.9% of a lupane triterpene having the structure: Where R 1 is connected to the ring system via a double bond and is oxygen, Where R 2 is selected from the group consisting of: CH 3 , CH 2 OR 4 , CHO, CO 2 H, CO 2 R 4 , COHNR 4 , CON(R 4 ) 2 , and CH 2 OCOR 4 where R 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 and sulfur, where the aryl group, if substituted, is substituted with a substituent selected from the group consisting of halogens, alkyl groups, OH, OR 4 , OCOR 4 , OCOOR 4 , OCONHR 4 , and OCON(R 4 ) 2 iii) OH, iv) OR 4 , v) OCOR 4 , vi) OCOOR 4 , vii) OCONHR 4 , and viii) OCON(R 4 ) 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 and sulfur, where the aryl group, if substituted, is substituted with a substituent selected from the group consisting of halogens, alkyl groups, OH, OR 4 , OCOR 4 , OCOOR 4 , OCONHR 4 , and OCON(R 4 ) 2 ; And where R 3 is selected from the group consisting of C(CH 3 )═CH 2 , CH(CH 3 ) 2 , COCH 3 , CH(OH)CH 3 , CH 2 CH 3 , C(R 5 )(CH 3 )CH 2 R 5 , C(CH 3 ) 2 R 5 , and CH(CH 3 )CH 2 R 5 , where R 5 is selected from the group consisting of OH and a halogen.
18 . A composition which comprises:
a) a pharmaceutically or cosmetically acceptable vehicle; and b) from about 0.00001% to about 99.9% of a lupane triterpene having the structure: Where R 1 is connected to the ring system via a double bond and is oxygen, Where R 2 is selected from the group consisting of: CH 3 , CH 2 OH, CH 2 OR 4 , CHO, CO 2 H, CO 2 R 4 , COHNR 4 , CON(R 4 ) 2 , and CH 2 OCOR 4 where R 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 and sulfur, where the aryl group, if substituted, is substituted with a substituent selected from the group consisting of halogens, alkyl groups, OH, OR 4 , OCOR 4 , OCOOR 4 , OCONHR 4 , and OCON(R 4 ) 2 iii) OH, iv) OR 4 , v) OCOR 4 , vi) OCOOR 4 , vii) OCONHR 4 , and viii) OCON(R 4 ) 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 and sulfur, where the aryl group, if substituted, is substituted with a substituent selected from the group consisting of halogens, alkyl groups, OH, OR 4 , OCOR 4 , OCOOR 4 , OCONHR 4 , and OCON(R 4 ) 2 ; And where R 3 is selected from the group consisting of C(CH 3 )═CH 2 , CH(CH 3 ) 2 , COCH 3 , CH(OH)CH 3 , CH 2 CH 3 , C(R 5 )(CH 3 )CH 2 R 5 , C(CH 3 ) 2 R 5 , and CH(CH 3 )CH 2 R 5 , where R 5 is selected from the group consisting of OH and a halogen.
19 . A composition which comprises:
a) a pharmaceutically or cosmetically acceptable vehicle; and b) from about 0.00001% to about 99.9% of a compound selected from the group consisting of:
i) compounds having the structure:
where R 1 is selected from the group consisting of CH 3 , CH 2 OH, CH 2 OR 4 , CHO, CO 2 H, CO 2 R 4 , COHNR 4 , CON(R 4 ) 2 , and CH 2 OCOR 4 , where R 4 is independently selected from the group consisting of 1) 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: a) halogens, b) substituted or unsubstituetd aryl groups comprising from 1 to 5 rings with or without heteroatoms, which heteroatoms are selected from the group consisting of nitrogen, oxygen and sulfur, where the aryl group, if substituted, is substituted with a substituent selected from the group consisting of halogens, alkyl groups, OH, OR 4 , OCOR 4 , OCOOR 4 , OCONHR 4 , and OCON(R 4 ) 2 c) OH, d), OR 4 , e) OCOR 4 , f) OCOOR 4 , g) OCONHR 4 , and h) OCON(R 4 ) 2 and 2) 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 and sulfur, where the aryl group, if substituted, is substituted with a substituent selected from the group consisting of halogens, alkyl groups, OH, OR 4 , OCOR 4 , OCOOR 4 , OCONHR 4 , and OCON(R 4 ) 2 ); where R 2 =CH 3 or H, where R 3 =CH 3 or H, and where R 4 =CH 3 or H; and
ii) derivatives of taraxastane triterpenes having the structure:
Where R 1 is either
1) connected to the ring system via a single bond, either α- or β-configuration, and is selected from the group consisting of H, OH, OR 4 , R 4 , OCOR 4 , OCOOR 4 , OCONHR 4 , and OCON(R 4 ) 2 , where R 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 and sulfur, where the aryl group, if substituted, is substituted with a substituent selected from the group consisting of halogens, alkyl groups, OH, OR 4 , OCOR 4 , OCOOR 4 , OCONHR 4 , and OCON(R 4 ) 2 iii) OH, iv) OR 4 , v) OCOR 4 , vi) OCOOR 4 , vii) OCONHR 4 , and viii) OCON(R 4 ) 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 and sulfur, where the aryl group, if substituted, is substituted with a substituent selected from the group consisting of halogens, alkyl groups, OH, OR 4 , OCOR 4 , OCOOR 4 , OCONHR 4 , and OCON(R 4 ) 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 4 —, and
Where R 2 is selected from the group consisting of: CH 3 , CH 2 OH, CH 2 OR 4 , CHO, CO 2 H, CO 2 R 4 , COHNR 4 , CON(R 4 ) 2 , and CH 2 OCOR 4 where R 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 4 , OCOR 4 , OCOOR 4 , OCONHR 4 , and OCON(R 4 ) 2 iii) OH, iv) OR 4 , v) OCOR 4 , vi) OCOOR 4 , vii) OCONHR 4 , and viii) OCON(R 4 ) 2 ; and
iii) salts of the acid forms of (i), (ii) or (iii); and
iv) mixtures of (i), (ii), or (iii).
20 . A composition which comprises a pharmaceutically or cosmetically acceptable vehicle and from 0.00001% to about 99.9% of betulonic acid.
21 . The composition of claim 20 which additionally comprises minoxidil.
22 . A composition which comprises a pharmaceutically or cosmetically acceptable vehicle and from 0.00001% to about 99.9% of a salt of betulonic acid.
23 . A composition which comprises:
a) a pharmaceutically or cosmetically acceptable vehicle; b) 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 in a concentration ranging from about 0.0001% to about 99.9%; and c) a second hair growth agent selected from the group consisting of vasodilators, antiandrogens, immunosuppressants, antiinflammatories, antimicrobials, thyroid hormones, prostoglandins, retinoids, vitamin D analogs, andparathyroid hormone analogs.
24 . The composition of claim 23 which is a topical composition.
25 . The composition of claim 24 wherein the pharmaceutically or cosmetically acceptable vehicle is present at a level ranging from about 50% to about 99.99% by weight of the composition.
26 . The composition of claim 8 wherein the compound is selected from the group consisting of betulinic acid, betulonic acid and mixtures thereof.
27 . The composition of claim 9 wherein the second hair growth agent is present at a level ranging from about 0.01% to about 10% by weight of the composition.Join the waitlist — get patent alerts
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