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US 2002/0161041 A1Published application
Resorcinol derivatives
AssigneePfizer Inc.
InventorsAndrew Francis Browning, Eric William Collington, Martin James Procter, Joanna Victoria Geden
Life of this patent
Estimating the term…
Abstract
The present invention relates to the use of certain resorcinol derivatives as skin lightening agents.
Claims64
A compound of formula l:
- 27
- or a pharmaceutically acceptable salt thereof, wherein:
- R1 is a (C3-C8)cycloalkyl ring or (C5-C8)cycloalkenyl ring, wherein either the cycloalkyl ring or cycloalkenyl ring is substituted by one to three substituents independently selected from the group consisting of cyano;
- halo;
- (C1-C6)alkyl;
- aryl;
- (C2-C9)heterocycloalkyl;
- (C2-C9)heteroaryl;
- aryl(C1-C6)alkyl-;
- ═O;
- ═CHO(C1-C6)alkyl;
- amino;
- hydroxy;
- (C1-C6)alkoxy;
- aryl(C1-C6)alkoxy-;
- (C1-C6)acyl;
- (C1-C6)alkylamino-;
- aryl(C1-C6)alkylamino-;
- amino(C1-C6)alkyl-;
- (C1-C6)alkoxy-CO—NH—;
- (C1-C6)alkylamino-CO—;
- (C2-C6)alkenyl;
- (C2-C6)alkynyl;
- hydroxy(C1-C6)alkyl-;
- (C1-C6)alkoxy(C1-C6)alkyl-;
- (C1-C6)acyloxy(C1-C6)alkyl-;
- nitro;
- cyano(C1-C6)alkyl-;
- halo(C1-C6)alkyl-;
- nitro(C1-C6)alkyl-;
- trifluoromethyl;
- trifluoromethyl(C1-C6)alkyl-;
- (C1-C6)acylamino-;
- (C1-C6)acylamino(C1-C6)alkyl-;
- (C1-C6)alkoxy(C1-C6)acylamino-;
- amino(C1-C6)acyl-;
- amino(C1-C6)acyl(C1-C6)alkyl-;
- (C1-C6)alkylamino(C1-C6)acyl-;
- ((C1-C6) alkyl)2amino(C1-C6)acyl-;
- —CO2R2;
- —(C1-C6)alkyl-CO2R2;
- —C(O)N(R2)2;
- —(C1-C6)alkyl-C(O)N(R2)2;
- R2ON═;
- R2ON═(C1-C6)alkyl-;
- R2ON═CR2(C1-C6)alkyl-;
- —NR2(OR2);
- —(C1-C6)alkyl-NR2(OR2);
- —C(O)(NR2R2);
- —(C1-C6)alkyl-C(O)(NR2OR2);
- —S(O)mR2;
- wherein each R2 is independently selected from hydrogen, (C1-C6)alkyl, aryl, or aryl(C1-C6)alkyl-;
- R3C(O)O—, wherein R3 is (C1-C6)alkyl, aryl, or aryl(C1-C6)alkyl-;
- R3C(O)O—(C1-C6)alkyl-;
- R4R5N—C(O)—O—;
- R4R5NS(O)2—;
- R4R5NS(O)2(C1-C6)alkyl-;
- R4S(O)2R5N—;
- R4S(O)2R5N(C1-C6)alkyl-;
- wherein m is 0, 1 or 2, and R4 and R5 are each independently selected from hydrogen or (C1-C6)alkyl;
- —C(═NR6)(N(R4)2);
- or —(C1-C6)alkyl-C(═NR6)(N(R4)2) wherein R6 represents OR2 or R2 wherein R2 is defined as above;
- with the proviso that the cycloalkenyl ring is not aromatic;
- with the proviso that R1 must be substituted by at least one of R3C(O)O—, R3C(O)O—(C1-C6)alkyl-, R2ON═, R2ON═(C1-C6)alkyl-, R2 ON═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-;
- with the proviso that when R1 is only substituted by one of R 20N═, then R cannot be hydrogen.
62 more elements
A topical pharmaceutical composition for lightening skin or reducing the pigmentation of skin in a human, comprising a pharmaceutically acceptable carrier, and a skin-lightening or pigmentation-reducing amount of a compound of formula I:
- 29
- or a pharmaceutically acceptable salt thereof, wherein:
- R1 is a (C3-C8)cycloalkyl ring or (C5-C8)cycloalkenyl ring, wherein either the cycloalkyl ring or cycloalkenyl ring is substituted by one to three substituents independently selected from the group consisting of cyano;
- halo;
- (C1-C6)alkyl;
- aryl;
- (C2-C9)heterocycloalkyl;
- (C2-C9)heteroaryl;
- aryl(C1-C6)alkyl-;
- ═O;
- ═CHO(C1-C6)alkyl;
- amino;
- hydroxy;
- (C1-C6)alkoxy;
- aryl(C1-C6)alkoxy-;
- (C1-C6)acyl;
- (C1-C6)alkylamino-;
- aryl(C1-C6)alkylamino-;
- amino(C1-C6)alkyl-;
- (C1-C6)alkoxy-CO—NH—;
- (C1-C6)alkylamino-CO—;
- (C2-C6)alkenyl;
- (C2-C6)alkynyl;
- hydroxy(C1-C6)alkyl-;
- (C1-C6)alkoxy(C1-C6)alkyl-;
- (C1-C6)acyloxy(C1-C6)alkyl-;
- nitro;
- cyano(C1-C6)alkyl-;
- halo(C1-C6)alkyl-;
- nitro(C1-C6)alkyl-;
- trifluoromethyl;
- trifluoromethyl(C1-C6)alkyl-;
- (C1-C6)acylamino-;
- (C1-C6)acylamino(C1-C6)alkyl-;
- (C1-C6)alkoxy(C1-C6)acylamino-;
- amino(C1-C6)acyl-;
- amino(C1-C6)acyl(C1-C6)alkyl-;
- (C1-C6)alkylamino(C1-C6)acyl-;
- ((C1-C6) alkyl)2amino(C1-C6)acyl-;
- —CO2R2;
- —(C1-C6)alkyl-CO2R2;
- —C(O)N(R2)2;
- —(C1-C6)alkyl-C(O)N(R2)2;
- R2ON═;
- R2ON═(C1-C6)alkyl-;
- R2ON═CR2(C1-C6)alkyl-;
- —NR2(OR2);
- —(C1-C6)alkyl-NR2(OR2);
- —C(O)(NR2R2);
- —(C1-C6)alkyl-C(O)(NR2OR2);
- —S(O)mR2;
- wherein each R2 is independently selected from hydrogen, (C1-C6)alkyl, aryl, or aryl(C1-C6)alkyl-;
- R3C(O)O—, wherein R3 is (C1-C6)alkyl, aryl, or aryl(C1-C6)alkyl-;
- R3C(O)O—(C1-C6)alkyl-;
- R4R5N—C(O)—O—;
- R4R5NS(O)2—;
- R4R5NS(O)2(C1-C6)alkyl-;
- R4S(O)2R5N—;
- R4S(O)2R5N(C1-C6)alkyl-;
- wherein m is 0, 1 or 2, and R4 and R5 are each independently selected from hydrogen or (C1-C6)alkyl;
- —C(═NR6)(N(R4)2);
- or —(C1-C6)alkyl-C(═NR6)(N(R4)2) wherein R6 represents OR2 or R2 wherein R2 is defined as above;
- with the proviso that the cycloalkenyl ring is not aromatic;
- with the proviso that R1 must be substituted by at least one of R3C(O)O—, R3C(O)O—(C1-C6)alkyl-, R2ON═, R2ON═(C1-C6)alkyl-, R2 ON═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-.
61 more elements
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:
- 31
- or a pharmaceutically acceptable salt thereof, wherein:
- R1 is a (C3-C8)cycloalkyl ring or (C5-C8)cycloalkenyl ring, wherein either the cycloalkyl ring or cycloalkenyl ring is substituted by one to three substituents independently selected from the group consisting of cyano;
- halo;
- (C1-C6)alkyl;
- aryl;
- (C2-C9)heterocycloalkyl;
- (C2-C9)heteroaryl;
- aryl(C1-C6)alkyl-;
- ═O;
- ═CHO(C1-C6)alkyl;
- amino;
- hydroxy;
- (C1-C6)alkoxy;
- aryl(C1-C6)alkoxy-;
- (C1-C6)acyl;
- (C1-C6)alkylamino-;
- aryl(C1-C6)alkylamino-;
- amino(C1-C6)alkyl-;
- (C1-C6)alkoxy-CO—NH—;
- (C1-C6)alkylamino-CO—;
- (C2-C6)alkenyl;
- (C2-C6)alkynyl;
- hydroxy(C1-C6)alkyl-;
- (C1-C6)alkoxy(C1-C6)alkyl-;
- (C1-C6)acyloxy(C1-C6)alkyl-;
- nitro;
- cyano(C1-C6)alkyl-;
- halo(C1-C6)alkyl-;
- nitro(C1-C6)alkyl-;
- trifluoromethyl;
- trifluoromethyl(C1-C6)alkyl-;
- (C1-C6)acylamino-;
- (C1-C6)acylamino(C1-C6)alkyl-;
- (C1-C6)alkoxy(C1-C6)acylamino-;
- amino(C1-C6)acyl-;
- amino(C1-C6)acyl(C1-C6)alkyl-;
- (C1-C6)alkylamino(C1-C6)acyl-;
- ((C1-C6) alkyl)2amino(C1-C6)acyl-;
- —CO2R2;
- —(C1-C6)alkyl-CO2R2;
- —C(O)N(R2)2;
- —(C1-C6)alkyl-C(O)N(R2)2;
- R2ON═;
- R2ON═(C1-C6)alkyl-;
- R2ON═CR2(C1-C6)alkyl-;
- —NR2(OR2);
- —(C1-C6)alkyl-NR2(OR2);
- —C(O)(NR2R2);
- —(C1-C6)alkyl-C(O)(NR2OR2);
- —S(O)mR2;
- wherein each R2 is independently selected from hydrogen, (C1-C6)alkyl, aryl, or aryl(C1-C6)alkyl-;
- R3C(O)O—, wherein R3 is (C1-C6)alkyl, aryl, or aryl(C1-C6)alkyl-;
- R3C(O)O—(C1-C6)alkyl-;
- R4R5N—C(O)—O—;
- R4R5NS(O)2—;
- R4R5NS(O)2(C1-C6)alkyl-;
- R4S(O)2R5N—;
- R4S(O)2R5N(C1-C6)alkyl-;
- wherein m is 0, 1 or 2, and R4 and R5 are each independently selected from hydrogen or (C1-C6)alkyl;
- —C(═NR6)(N(R4)2);
- or —(C1-C6)alkyl-C(═NR6)(N(R4)2) wherein R6 represents OR2 or R2 wherein R2 is defined as above;
- with the proviso that the cycloalkenyl ring is not aromatic;
- with the proviso the when R1 is a (C5-C8)cycloalkyl ring, or when R1 is a (C5-C8)cycloalkenyl ring having the following structure:
- 32
- wherein n is 0, 1, 2 or 3, where such (C5-C8)cycloalkyl ring or (C5-C8)cycloalkenyl ring is substituted by hydroxy, (C1-C6)alkoxy-, aryl(C1-C6)alkoxy-, —OC(O)(C1-C6)alkyl, —OC(O)aryl(C1-C6)alkyl, —OC(O)phenyl, halo, (C1-C6)alkyl-, aryl(C1-C6)alkyl-, —SH, —S(C1-C6)alkyl, aryl(C1-C6)alkyl-S—, —NH2, —NH(C1-C6)alkyl, or aryl(C1-C6)alkyl-HN—;
- then the (C5-C8)cycloalkyl ring or the (C5-C8)cycloalkenyl ring must be di- or tri-substituted.
64 more elements
Dependencies are inferred from the claim text.