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US 6,914,074 B2Granted
Substituted phenyl naphthalenes as estrogenic agents
AssigneeWyeth
InventorsRichard E. Mewshaw, Richard J. Edsall, Cuijian Yang, Heather A. Harris, James C. Keith, Jr., Leo M. Albert, Eric S. Manas
Life of this patent
Estimating the term…
Abstract
This invention provides estrogen receptor modulators of formula I, having the structure wherein R1, R2, R3, R4, R5, R6, R7, R8, R9, and R10, are as defined in the specification, or a pharmaceutically acceptable salt thereof.
Claims8
A compound of formula I, having the structure
- wherein
- R1 and R2 are each, independently, selected from hydrogen, hydroxyl, alkyl of 1-6 carbon atoms, alkenyl of 2-7 carbon atoms, and alkynyl of 2-7 carbon atoms, alkoxy of 1-6 carbon atoms, or halogen;
- R5, R6, R7, R8, and R9 are each, independently, hydrogen, alkyl of 1-6 carbon atoms, alkenyl of 2-7 carbon atoms, alkynyl of 2-7 carbon atoms, halogen, alkoxy of 1-6 carbon atoms, —CN, trifluoromethyl, phenylalkyl of 7-12 carbon atoms, phenyl, wherein the alkyl or alkenyl moieties of R5, R6, R7, R8, or R9 may be optionally substituted with hydroxyl, —CN, halogen, trifluoroalkyl, trifluoroalkoxy, —NO2, or phenyl;
- wherein the phenyl moiety of R5, R6, R7, R8, or R9 may be optionally mono-, di-, or tri-substituted with alkyl of 1-6 carbon atoms, alkenyl of 2-7 carbon atoms, halogen, hydroxyl, alkoxy of 1-6 carbon atoms, halogen, —CN, —NO2, amino, alkylamino of 1-6 carbon atoms, dialkylamino of 1-6 carbon atoms per alkyl group, thio, alkylthio of 1-6 carbon atoms, alkylsufinyl of 1-6 carbon atoms, alkylsulfonyl of 1-6 carbon atoms, alkoxycarbonyl of 2-7 carbon atoms, alkylcarbonyl of 2-7 carbon atoms, or benzoyl;
- with the proviso that at least one of R5 or R9 is not hydrogen, or a pharmaceutically acceptable salt thereof.
2 more elements
A compound which is
- a) 7-(4-hydroxyphenyl)-2-naphthol;
- b) 7-(3-hydroxyphenyl)-2-naphthol;
- c) 6-(4-hydroxyphenyl)-1-naphthol;
- d) 6-phenyl-2-naphthol;
- e) 6-(3-hydroxylphenyl)-2-naphthol;
- f) 6-(3-chlorophenyl)-2-naphthol;
- g) 2-fluoro-4-(2-naphthyl)phenol;
- h) 6-(3-fluoro-4-hydroxyphenyl)-2-naphthol;
- i) 6-(3-chloro-4-hydroxyphenyl)-2-naphthol;
- j) 1-chloro-6-phenyl-2-naphthol;
- k) 1-bromo-6-(4-hydroxyphenyl)-2-naphthol;
- l) 1-chloro-6-(4-hydroxyphenyl)-2-naphthol;
- m) 1-fluoro-6-(4-hydroxyphenyl)-2-naphthol;
- n) 2-hydroxy-6-(4-hydroxyphenyl)-2-naphthonitrile;
- o) 6-(4-hydroxyphenyl)-1-phenyl-2-naphthol;
- p) 6-(4-hydroxyphenyl)-1-methyl-2-naphthol;
- q) 1-chloro-6-(3-fluoro-4-hydroxyphenyl)-2-naphthol;
- r) 1-chloro-6-(3-chloro-4-hydroxyphenyl-2-naphthol;
- s) 6-(4-hydroxyphenyl)-1-nitro-2-naphthol;
- t) 1-chloro-6-(4-hydroxy-2-methylphenyl)-2-naphthol;
- u) 6-(4-hydroxy-2-methylphenyl)-2-naphthol;
- v) 6-(4-hydroxy-2-methoxyphenyl)-2-naphthol;
- w) 6-(2-chloro-4-hydroxyphenyl)-2-naphthol;
- x) 1-chloro-6-(2-chloro-4-hydroxyphenyl)-2-naphthol;
- y) 6-(2-fluoro-4-hydroxyphenyl)-2-naphthol;
- z) 6-(2,5-difluoro-4-hydroxyphenyl)-2-naphthol;
- aa) 6-(2,6-difluoro-4-hydroxyphenyl)-2-naphthol;
- bb) 1-chloro-6-(2-fluoro-4-hydroxyphenyl)-2-naphthol;
- cc) 1-chloro-6-(2,5-difluoro-4-hydroxyphenyl)-2-naphthol;
- dd) 1-chloro-6-(2,6-difluoro-4-hydroxyphenyl)-2-naphthol;
- ee) 8-fluoro-6-(4-hydroxyphenyl)-2-naphthol;
- ff) 1-chloro-8-fluoro-6-(4-hydroxyphenyl)-2-naphthol;
- gg) 8-chloro-6-(4-hydroxyphenyl)-2-naphthol;
- hh) 1,5-dichloro-8-fluoro-6-(4-hydroxyphenyl-2-naphthol;
- ii) 2-chloro-4-(2-naphthyl)phenol;
- jj) 3-bromo-8-chloro-6-(4-hydroxyphenyl)-2-naphthol;
- kk) 1,8-dichloro-6-(4-hydroxyphenyl)-2-naphthol;
- ll) 3-bromo-1,8-dichloro-6-(4-hydroxyphenyl)-2-naphthol;
- mm) 7-hydroxy-3-(4-hydroxyphenyl)-1-naphthonitrile;
- nn) 8-chloro-3-(4-hydroxyphenyl)-7-hydroxy-1-naphthonitrile;
- oo) 8-chloro-3-(3-fluoro-4-hydroxyphenyl)-7-hydroxy-1-naphthonitrile;
- pp) 6-(3,5-difluoro-4-hydroxyphenyl)-2-naphthol;
- qq) 1-chloro-6-(3,5-difluoro-4-hydroxyphenyl)-2-naphthol;
- rr) 8-bromo-7-hydroxy-3-(4-hydroxyphenyl)-1-naphthonitrile or a pharmaceutically acceptable salt thereof.
41 more elements
A method of treating arthritis in a mammal in need thereof, which comprises providing to said mammal an effective amount of a compound of formula I, having the structure
- wherein
- R1 and R2 are each, independently, selected from hydrogen, hydroxyl, alkyl of 1-6 carbon atoms, alkenyl of 2-7 carbon atoms, and alkynyl of 2-7 carbon atoms, alkoxy of 1-6 carbon atoms, or halogen;
- R5, R6, R7, R8, and R9 are each, independently, hydrogen, alkyl of 1-6 carbon atoms, alkenyl of 2-7 carbon atoms, alkynyl of 2-7 carbon atoms, halogen, alkoxy of 1-6 carbon atoms, —CN, —CHO, trifluoromethyl, phenylalkyl of 7-12 carbon atoms, phenyl, wherein the alkyl or alkenyl moieties of R5, R6, R7, R8, or R9 may be optionally substituted with hydroxyl, —CN, halogen, trifluoroalkyl, trifluoroalkoxy, —NO2, or phenyl;
- wherein the phenyl moiety of R5, R6, R7, R8, or R9 may be optionally mono-, di-, or tri-substituted with alkyl of 1-6 carbon atoms, alkenyl of 2-7 carbon atoms, halogen, hydroxyl, alkoxy of 1-6 carbon atoms, halogen, —CN, —NO2, amino, alkylamino of 1-6 carbon atoms, dialkylamino of 1-6 carbon atoms per alkyl group, thio, alkylthio of 1-6 carbon atoms, alkylsufinyl of 1-6 carbon atoms, alkylsulfonyl of 1-6 carbon atoms, alkoxycarbonyl of 2-7 carbon atoms, alkylcarbonyl of 2-7 carbon atoms, or benzoyl;
- with the proviso that at least one of R5 or R9 is not hydrogen, or a pharmaceutically acceptable salt thereof.
2 more elements
A pharmaceutical composition which comprises a compound of formula 1, having the structure
- wherein
- R1 and R2 are each, independently, selected from hydrogen, hydroxyl, alkyl of 1-6 carbon atoms, alkenyl of 2-7 carbon atoms, and alkynyl of 2-7 carbon atoms, alkoxy of 1-6 carbon atoms, or halogen;
- R5, R6, R7, R8, and R9 are each, independently, hydrogen, alkyl of 1-6 carbon atoms, alkenyl of 2-7 carbon atoms, alkynyl of 2-7 carbon atoms, halogen, alkoxy of 1-6 carbon atoms, —CN, —CHO, trifluoromethyl, phenylalkyl of 7-12 carbon atoms, phenyl, wherein the alkyl or alkenyl moieties of R5, R6, R7, R8, or R9 may be optionally substituted with hydroxyl, —CN, halogen, trifluoroalkyl, trifluoroalkoxy, —NO2, or phenyl;
- wherein the phenyl moiety of R5, R6, R7, R8, or R9 may be optionally mono-, di-, or tri-substituted with alkyl of 1-6 carbon atoms, alkenyl of 2-7 carbon atoms, halogen, hydroxyl, alkoxy of 1-6 carbon atoms, halogen, —CN, —NO2, amino, alkylamino of 1-6 carbon atoms, dialkylamino of 1-6 carbon atoms per alkyl group, thio, alkylthio of 1-6 carbon atoms, alkylsufinyl of 1-6 carbon atoms, alkylsulfonyl of 1-6 carbon atoms, alkoxycarbonyl of 2-7 carbon atoms, alkylcarbonyl of 2-7 carbon atoms, or benzoyl;
- with the proviso that at least one of R5 or R9 is not hydrogen, or a pharmaceutically acceptable salt thereof, and a pharmaceutical carrier.
2 more elements
Dependencies are inferred from the claim text.