Claims
- 1-41. (cancelled).
- 42: A method of lightening skin or reducing the pigmentation of skin in a human, comprising administering to said human a skin-lightening or skin pigmentation-reducing effective amount of a compound of formula I:
- 43. The method of claim 42, wherein R1 of the compound is a cyclohexyl or cyclohexenyl ring substituted at the 3- or 4-position, or a cyclopentyl or cyclopentenyl ring substituted at the 3-position.
- 44. The method of claim 42, wherein R1 of the compound is monosubstituted.
- 45. The method of claim 42, wherein R1 of the compound is disubstituted.
- 46. The method of claim 42, wherein R1 of the compound is substituted by at least one of R3C(O)O— or R3C(O)O—(C1-C6)alkyl-.
- 47. The method of claim 42, wherein R1 of the compound is substituted by at least one of R2ON═, R2ON═(C1-C6)alkyl-, or R2ON═CR2(C1-C6)alkyl-.
- 48. The method of claim 42, wherein R1 of the compound is substituted by at least one of —NR2(OR2).
- 49. The method of claim 42 wherein R1 of the compound is substituted by at least one of R4R5NS(O)2—, R4R5NS(O)2(C1-C6)alkyl-, R4S(O)2R5N—, or R4S(O)2R5N(C1-C6)alkyl-.
- 50. The method of claim 42, wherein R1 of the compound is substituted by at least one of R4S(O)2R5N— or R4S(O)2R5N(C1-C6)alkyl-.
- 51. The method of claim 42, wherein R1 of the compound is a (C3-C8)cycloalkyl ring or (C5-C8)cycloalkenyl ring, wherein either the cycloalkyl ring or cycloalkenyl ring is substituted by one of R3C(O)O—, R3C(O)O—(C1-C6)alkyl-, R2ON═, R2ON═(C1-C6)alkyl-, R2ON═CR2(C1-C6)alkyl-, —NR2(OR2), R4R5NS(O)2—, R4R5NS(O)2(C1-C6)alkyl-, R4S(O)2R5N—, or R4S(O)2R5N(C1-C6)alkyl-.
- 52. The method of claim 51, wherein R1 of the compound is a (C3-C8)cycloalkyl ring or (C5-C8)cycloalkenyl ring, wherein either the cycloalkyl ring or cycloalkenyl ring is substituted by one of R3C(O)O—, R3C(O)O—(C1-C6)alkyl-, R2ON═, or R4S(O)2R5N—.
- 53. The method of claim 51, wherein R1 of the compound is substituted by R3C(O)O— or R3C(O)O—(C1-C6)alkyl-.
- 54. The method of claim 51, wherein R1 of the compound is substituted by R2ON═, R2ON═(C1-C6)alkyl-, or R2ON═CR2(C1-C6)alkyl-.
- 55. The method of claim 51, wherein R1 of the compound is substituted by R2ON═.
- 56. The method of claim 51, wherein R1 of the compound is substituted by —NR2(OR2).
- 57. The method of claim 51, wherein R1 of the compound is substituted by R4R5NS(O)2—, R4R5NS(O)2(C1-C6)alkyl-, R4S(O)2R5N— or R4S(O)2R5N(C1-C6)alkyl-.
- 58. The method of claim 51, wherein R1 of the compound is substituted by R4S(O)2R5N— or R4S(O)2R5N(C1-C6)alkyl-.
- 59. The method of claim 42, wherein the (C2-C9)heterocycloalkyl substituent is a group of the formula:
- 60. The method of claim 46, wherein R1 is a group of the formula:
- 61. The method of claim 60, wherein R1 of the compound is substituted by ═O, ═NOH, CH2OH,
- 62. The method of claim 42, wherein the compound is selected from the group consisting of:
4-(2,4-Dihydroxyphenyl)cyclohexanone; 4-(2,4-Dihydroxyphenyl)cyclohexanone oxime; O-Methyl-4-(2,4-dihydroxyphenyl)cyclohexanone oxime; O-Benzyl-4-(2,4-dihydroxyphenyl)cyclohexanone oxime; 3-(2,4-dihydroxyphenyl)-2-cyclohexen-1-one; (±)-3-(2,4-Dihydroxyphenyl)cyclohexanone; 3-(2,4-Dihydroxyphenyl)-2-cyclohexen-1-one oxime; (±)-3-(2,4-Dihydroxyphenyl)cyclohexanone oxime; (±)-4-[3-(1-Piperazinyl)cyclohexyi]-1,3-benzenediol; (±)-N-[3-(2,4-Dihydroxyphenyl)cyclohexyl]methanesulfonamide; (±)-4-[3-(Hydroxymethyl)cyclohexyl]-1,3-benzenediol; (±)-4-[3-(Hydroxyamino)cyclohexyl]-1,3-benzenediol; cis/trans-4-[4-(Hydroxymethyl)cyclohexyl]-1,3-benzenediol; cis/trans-4-(4-Hydroxy-4-methylcyclohexyl)-1,3-benzenediol; (±)-O-Methyl-3-(2,4-dihydroxyphenyl)cyclohexanone oxime; (±)-3-(2,4-Dihydroxyphenyl)-1-methylcyclohexanol; (±)-O-Benzyl-3-(2,4-dihydroxyphenyl)cyclohexanone oxime; 3-(2,4-Dihydroxyphenyl)-2-cyclopentenone oxime; (±)-3-(2,4-Dihydroxyphenyl)cyclopentanone; (±)-3-(2,4-Dihydroxyphenyl)cyclopentanone oxime; and a pharmaceutically acceptable salt thereof.
- 63. The method of claim 42, wherein the compound is selected from the group consisting of:
4-(2,4-Dihydroxyphenyl)-3-cyclohexen-1-one; cis/trans-N-[4-(2,4-Dihydroxyphenyl)cyclohexyl]acetamide; cis-N-[4-(2,4-Dihydroxyphenyl)cyclohexyl]-1-butanesulfonamide; trans-N-[4-(2,4-Dihydroxyphenyl)cyclohexyl]methanesulfonamide; cis-N-[4-(2,4-Dihydroxyphenyl)cyclohexyl]methanesulfonamide; 4-[4-(4-Hydroxyphenyl)cyclohexyl]-1,3-benzenediol; cis/trans-Methyl[4-(2,4-dihydroxyphenyl)cyclohexyl]acetate; trans-Methyl[4-(2,4-dihydroxyphenyl)cyclohexyl]acetate; cis-Methyl[4-(2,4-dihydroxyphenyl)cyclohexyl]acetate; trans-[4-(2,4-Dihydroxyphenyl)cyclohexyl]acetic acid; cis-[4-(2,4-Dihydroxyphenyl)cyclohexyl]acetic acid; cis/trans-[4-(2,4-Dihydroxyphenyl)cyclohexyl]acetic acid; cis/trans-[4-(2,4-Dihydroxyphenyl)cyclohexyl]acetonitrile; cis/trans-4-[4-(2-Aminoethyl)cyclohexyl]-1,3-benzenediol; (±)-4-(3,3-Difluorocyclohexyl)-1,3-benzenediol; (±)-3-(2,4-Dihydroxyphenyl)cyclohexanecarboxamide; (±)-3-(2,4-Dihydroxyphenyl)-N-hydroxycyclohexanecarboxamide; (±)-3-(2,4-Dihydroxyphenyl)-N-ethylcyclohexanecarboxamide; (±)-4-[3-Hydroxy-3-(hydroxymethyl)cyclohexyl]-1,3-benzenediol; (±)-N-[3-(2,4-dihydroxyphenyl)cyclohexyl]acetamide; trans-4-(2,4-Dihydroxyphenyl)cyclohexyl) 4-(dimethylamino)benzoate; cis/trans-4-(2,4-Dihydroxyphenyl)cyclohexanecarboxylic acid; trans-4-(2,4-Dihydroxyphenyl)cyclohexyl ethylcarbamate; trans-4-(2,4-Dihydroxyphenyl)cyclohexyl cyclohexylcarbamate; trans-4-(2,4-Dihydroxyphenyl)cyclohexyl 4-tert-butylbenzoate; trans-4-(2,4-Dihydroxyphenyl)cyclohexyl 4-fluorobenzoate; trans-4-(2,4-Dihydroxyphenyl)cyclohexyl 4-trifluoromethylbenzoate; trans-4-(2,4-Dihydroxyphenyl)cyclohexyl 4-methoxybenzoate; trans-4-(2,4-Dihydroxyphenyl)cyclohexyl 4-methylbenzoate; trans-4-(2,4-Dihydroxyphenyl)cyclohexyl 4-chlorobenzoate; trans-4-(2,4-Dihydroxyphenyl)cyclohexyl 3,4-dimethylbenzoate; trans-4-(2,4-Dihydroxyphenyl)cyclohexyl 3,4-dichlorobenzoate; trans-4-[4-(PhenylsuIfanyl)cyclohexyl]-1,3-benzenediol; trans-4-[4-(Phenylsulfonyl)cyclohexyl]-1,3-benzenediol; [4-(2,4-Dihydroxyphenyl)cyclohexyl]methyl propionate; ethyl 4-(2,4-dihydroxyphenyl)-1-hydroxycyclohexane carboxylate; cis/trans-4-[4-(hydroxyamino)cyclohexyl]-1,3-benzenediol; trans-4-[4-(methoxyamino)cyclohexyl]-1,3-benzenediol; and a pharmaceutically acceptable salt thereof.
- 64. The method of claim 42, wherein the skin-lightening or pigmentation-reducing effective amount of a compound of formula I is a tyrosinase-inhibiting effective amount of the compound.
Parent Case Info
[0001] This application is a continuation-in-part of U.S. application Ser. No. 09/526,287, filed Mar. 15, 2000, which claims priority from U.S. provisional application Serial No. 60/125,534, filed Mar. 22, 1999.
Provisional Applications (1)
|
Number |
Date |
Country |
|
60125534 |
Mar 1999 |
US |
Divisions (1)
|
Number |
Date |
Country |
Parent |
10020037 |
Dec 2001 |
US |
Child |
10839432 |
May 2004 |
US |
Continuation in Parts (1)
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Number |
Date |
Country |
Parent |
09526287 |
Mar 2000 |
US |
Child |
10020037 |
Dec 2001 |
US |