Triphenylethylene Compounds Useful as Selective Estrogen Modulators
First Claim
Patent Images
1. A compound of Formula I or a pharmaceutically acceptable salt or solvate thereof, whereinR1 is selected from the group consisting of C1-C6 alkyl and C1-C6 haloalkyl;
- each R2 is the same and selected from the group consisting of —
OH, halogen, C1-C4 alkoxy, —
S—
R6, —
SO—
R6, and —
SO2—
R6;
each R3 is the same and selected from hydrogen, —
OH, C1-C6 alkyl, halogen, C1-C6 alkoxy, and C1-C6 haloalkyl;
R4 is selected from —
O—
Ra—
R8;
R5 is selected from hydrogen, —
OH, C1-C6 alkyl, halogen, C1-C6 alkoxy, and C1-C6 haloalkyl;
Ra is selected from C1-C6 alkylene;
R6 is a substituted or unsubstituted C1-C6 alkyl group;
R8 is selected from NR9R10; and
R9 and R10 are independently selected from H, C1-C6 alkyl, hydroxy (C1-C6) alkyl, and methoxy (C1-C6) alkyl, or R9 and R10 together with the nitrogen atom to which they are attached form a 4-8 membered heterocycle, optionally substituted with one or more halogen and/or one or more C1-C6 alkyl;
with the proviso that R4 is —
O—
CH2—
CH2—
NCH3CH3 only if R5 is C1-C6 alkoxy.
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Abstract
Triphenylethylene compounds of formula (I) are provided. The compounds are particularly useful for selective estrogen receptor modulation.
49 Citations
18 Claims
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1. A compound of Formula I
or a pharmaceutically acceptable salt or solvate thereof, wherein R1 is selected from the group consisting of C1-C6 alkyl and C1-C6 haloalkyl; -
each R2 is the same and selected from the group consisting of —
OH, halogen, C1-C4 alkoxy, —
S—
R6, —
SO—
R6, and —
SO2—
R6;each R3 is the same and selected from hydrogen, —
OH, C1-C6 alkyl, halogen, C1-C6 alkoxy, and C1-C6 haloalkyl;R4 is selected from —
O—
Ra—
R8;R5 is selected from hydrogen, —
OH, C1-C6 alkyl, halogen, C1-C6 alkoxy, and C1-C6 haloalkyl;Ra is selected from C1-C6 alkylene; R6 is a substituted or unsubstituted C1-C6 alkyl group; R8 is selected from NR9R10; and R9 and R10 are independently selected from H, C1-C6 alkyl, hydroxy (C1-C6) alkyl, and methoxy (C1-C6) alkyl, or R9 and R10 together with the nitrogen atom to which they are attached form a 4-8 membered heterocycle, optionally substituted with one or more halogen and/or one or more C1-C6 alkyl; with the proviso that R4 is —
O—
CH2—
CH2—
NCH3CH3 only if R5 is C1-C6 alkoxy. - View Dependent Claims (2, 3, 4, 5, 6, 9, 14, 17, 18)
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7. A compound of Formula I
or a pharmaceutically acceptable salt or solvate, or physiologically thereof, wherein R1 is selected from the group consisting of C1-C6 alkyl and C1-C6 haloalkyl; -
each R2 is —
OH;each R3 is hydrogen; R4 is selected from —
O—
Ra—
R8;R5 is selected from hydrogen and C1-C6 alkoxy; Ra is selected from C1-C6 alkylene; R8 is selected from NR9R10; and R9 and R10 are independently selected from H and C1-C6 alkyl, or R9 and R10 together with the nitrogen atom to which they are attached form a 4-8 membered heterocycle; with the proviso that R4 is —
O—
CH2—
CH2—
NCH3CH3 only if R5 is C1-C6 alkoxy.
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8. A compound selected from the group consisting of:
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4,4′
-[2-(3-{[2-(Dimethylamino)ethyl]oxy}phenyl)-1-butene-1,1-diyl]diphenol;4,4′
-[2-(3-{[2-(1-Piperidinyl)ethyl]oxy}phenyl)-1-hexene-1,1-diyl]diphenol;4,4′
-[2-(3-{[2-(1-Pyrrolidinyl)ethyl]oxy}phenyl)-1-butene-1,1-diyl]diphenol;4,4′
-[2-(3-{[2-(1-Piperidinyl)ethyl]oxy}phenyl)-1-butene-1,1-diyl]diphenol;4,4′
-[2-(3-{[2-(Hexahydro-1H-azepin-1-yl)ethyl]oxy}phenyl)-1-butene-1,1-diyl]diphenol;4,4′
-[2-(3-{[2-(dimethylamino)ethyl]oxy}phenyl)-1-pentene-1,1-diyl]diphenol;4,4′
-[2-(3-{[2-(1-pyrrolidinyl)ethyl]oxy}phenyl)-1-pentene-1,1-diyl]diphenol;4,4′
-[2-(3-{[2-(1-piperidinyl)ethyl]oxy}phenyl)-1-pentene-1,1-diyl]diphenol;4,4′
-[2-(3-{[2-(dimethylamino)ethyl]oxy}phenyl)-1-hexene-1,1-diyl]diphenol;4,4′
-[2-(3-{[2-(1-pyrrolidinyl)ethyl]oxy}phenyl)-1-hexene-1,1-diyl]diphenol;4,4′
-[2-(3-{[2-(Hexahydro-1H-azepin-1-yl)ethyl]oxy}phenyl)-1-pentene-1,1-diyl]diphenol;4,4′
-[2-(3-{[2-(Hexahydro-1H-azepin-1-yl)ethyl]oxy}phenyl)-1-hexene-1,1-diyl]diphenol;4,4′
-[2-(3-{[2-(Dimethylamino)ethyl]oxy}phenyl)-1-heptene-1,1-diyl]diphenol;4,4′
-[2-(3-{[2-(1-Pyrrolidinyl)ethyl]oxy}phenyl)-1-heptene-1,1-diyl]diphenol;4,4′
-[2-(3-{[2-(1-Piperidinyl)ethyl]oxy}phenyl)-1-heptene-1,1-diyl]diphenol;4,4′
-[2-(3-{[2-(Hexahydro-1H-azepin-1-yl)ethyl]oxy}phenyl)-1-heptene-1,1-diyl]diphenol;4,4′
-{2-[3-{[2-(Dimethylamino)ethyl]oxy}-4-(methyloxy)phenyl]-1-butene-1,1-diyl}diphenol;4,4′
-{2-[3-{[2-(Dimethylamino)ethyl]oxy}-4-(methyloxy)phenyl]-1-pentene-1,1-diyl}diphenol;4,4′
-{2-[3-{[2-(Dimethylamino)ethyl]oxy}-4-(methyloxy)phenyl]-1-hexene-1,1-diyl}diphenol;4,4′
-{2-[3-({2-[(3S)-3-Fluoro-1-pyrrolidinyl]ethyl}oxy)phenyl]-1-heptene-1,1-diyl}diphenol;4,4′
-[2-(3-{[2-(3,3-Difluoro-1-pyrrolidinyl)ethyl]oxy}phenyl)-1-heptene-1,1-diyl]diphenol;4,4′
-[2-(3-{[2-(1-Pyrrolidinyl)propyl]oxy}phenyl)-1-heptene-1,1-diyl]diphenol;and, 4,4′
-[2-(3-{[2-(2-Methyl-1-pyrrolidinyl)ethyl]oxy}phenyl)-1-heptene-1,1-diyl]diphenolor a pharmaceutically acceptable salt or solvate thereof.
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10. (canceled)
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11. (canceled)
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12. (canceled)
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13. (canceled)
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15. (canceled)
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16. (canceled)
Specification