Non-steroidal modulators of estrogen receptors
OwnerMary Jane Meegan, Rosario Bridget Hughes +2inventors
InventorsMary Jane Meegan, Rosario Bridget Hughes, Daniela Maria Zisterer, David George Lloyd
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Abstract
Estrogen receptor modulators, compositions comprising the compounds and methods relating to the use thereof are described. The compounds may be used in inhibiting the proliferation of and/or induces apoptosis in human breast cancer cells.
Claims44
A compound of the formula I
- 31
- wherein R1=H, OH, Br, NH2 or R4 wherein R4 is O(CH2)2NRaRb or NH(CH2)xNRaRb or NH(CH2)xRa-Rb or O(CH2)xRa-Rb and Ra and Rb are independently H, O, CH3, C2 H5, C3 H7 or optionally part of a heterocyclic ring system of the structure:
- 32
- wherein n4 and n5 are independently 0 or 1 and both are not 0, and
- A is CH2 or O;
- and x is 2 or 3,
- R2 is independently one of H, OH, OPiv, OAc, OCONHMe, OMe R3 is independently one of H, OH, OPiv OMe or para O(CH2)2NRaRb wherein Ra and Rb are as defined above,
- n1, n2 and n3=0 or 1 independently, and n1, n2 and n3 are such that only one n=1 at any one time where n1, n2 and n3 are not all equal to 0,
- and isomers, prodrugs and pharmaceutically acceptable salts thereof.
A compound selected from
- 2-Benzyl-1-phenyl-1-[4-(dimethylaminoethoxy)phenyl]but-1-ene
- 2-Benzyl-1-phenyl-1-[4-(diethylaminoethoxy)phenyl]but-1-ene
- 2-Benzyl-1-phenyl-1-[4-(pyrrolidinylethoxy)phenyl]but-1-ene
- 2-Benzyl-1-phenyl-1-[4-(pipyridinylethoxy)phenyl]but-1-ene
- 2-Benzyl-1-phenyl-1-[4-(morpholinylethoxy)phenyl]but-1-ene
- 1-Benzyl-2-phenyl-[(4-dimethyleaminoethoxy)phenyl]but-1-ene
- 1-Benzyl-2-phenyl-[1-(4-diethylaminoethoxy)phenyl]-but-1-ene
- 1-Benzyl-2-phenyl-[1-(4-pyrrolidinylethoxy)phenyl]-but-1-ene
- 1-Benzyl-2-phenyl-[1-(4-pipyridinylethoxy)phenyl]-but-1-ene
- 1-Benzyl-2-phenyl[1-(5-morpholinylethoxy)phenyl]but-1-ene
- 1-Benzyl-1-phenyl-2-[(4-dimethylaminoethoxy)phenyl]but-1-ene
- 1-Benzyl-1-phenyl-2-[(4-diethylaminoethoxy)phenyl]but-1-ene
- 1-Benzyl-1-phenyl-2-[(4-pyrrolidinylethoxy)phenyl]but-1-ene
- 1-Benzyl-1-phenyl-2-[(4-pipyridinylethoxy)phenyl]but-1-ene
- 1-Benzyl-1-phenyl-2-[(4-morpholinylethoxy)phenyl]but-1-ene
- 1,2-Diphenyl-2-[2-(dimethylaminoethoxy)benzyl]but-1-ene
- 1,2-Diphenyl-2-[2-(diethylaminoethoxy)benzyl]but-1-ene
- 1,2-Diphenyl-2-[(4-pyrrolidinylethoxy)benzyl]but-1-ene
- 1,2-Diphenyl-2-[(4-pipyridinylethoxy)benzyl]but-1-ene
- 1,2-Diphenyl-2-[(4-morpholinylethoxy)benzyl]but-1-ene
- 2,2-Dimethyl-propionic acid 4-{2-benzyl-1-[4-(2-pyrrolidin-1-yl-ethoxy-phenyl]-but-1-enyl}-phenyl ester
- 2,2-Dimethyl-propionic acid 4-{2-benzyl-1-[4-(2-dimethylamino-ethoxy-phenyl]-but-1-enyl}-phenyl ester
- 2,2-Dimethyl-propionic acid 4-{2-benzyl-1-[4-(2-morpholin-4-yl -ethoxy-phenyl]-but-1-enyl}-phenyl ester
- 4-{2-Benzyl-1-[4-(2-dimethylamino-ethoxy)-phenyl]-but-1-enyl}-phenol
- 4-{2-Benzyl-1-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-but-1-enyl}-phenol
- 2,2-Dimethyl-propionic acid 4-{2-(2-methoxybenzyl)-1-[4-(2-pyrrolidin-1 -yl-ethoxy)-phenyl]-but-1-enyl}-phenyl ester
- [4-(2-Benzyl-1-phenylbut-1-enyl)-phenyl]-(2-methoxyethyl)-amine
- [4-(2-Benzyl-1-phenylbut-1-enyl)-phenyl]-(2-ethoxyethyl)-amine
- [4-(2-Benzyl-1-phenylbut-1-enyl)-phenyl]-(2-prop oxyethyl)-amine
- [4-(2-Benzyl-1-phenylbut-1-enyl)-phenyl]-(3-methoxypropyl)-amine
- [4-(2-Benzyl-1-phenylbut-1-enyl)-phenyl]-(3-ethoxypropyl)-amine
- [4-(2-Benzyl-1-phenylbut-1-enyl)-phenyl]-(3-propoxypropyl)-amine
- 2-[4-(2-Benzyl-1-phenylbut-1-enyl)-phenylamino]-ethanol
- 3-[4-(2-Benzyl-1-phenylbut-1-enyl)-phenylamino]-propan-1-ol
- 2-[4-(2-Benzyl-1-phenylbut-1-enyl)-phenoxy]-ethanol
- 3-[4-(2-Benzyl-1-phenylbut-1-enyl)-phenoxy]-propan-1-ol
- {4-[2-Benzyl-1-(4-methoxyphenyl)-but-1-enyl]-phenyl}-(2-methoxyethyl)-amine
- {4-[2-(4-methoxybenzyl)-1-(4-methoxyphenyl)-but-1-enyl]-phenyl}-(2-methoxyethyl)-amine
- {4-[2-(4-methoxybenzyl)-1-phenylbut-1 -enyl]-phenyl} -(2-methoxyethyl)-amine
- 1-(2-Benzyl-1-phenylbut-1-enyl)-4-(2-methoxyethoxy)-benzene
- 4-{2-Ethyl-3-[4-(2-methoxyethylamino)-phenyl]-3-phenylallyl}-phenol
- N′-[4-(2-Benzyl-1-phenylbut-1-enyl)-phenyl]-N,N-dimethylethane-1,2-diamine.
2-Benzyl-1-phenyl-1-[4-(pyrrolidinylethoxy)phenyl]but-1-ene.
2-Benzyl-1-phenyl-1-[4-(pipyridinylethoxy)phenyl]but-1 -ene.
1-Benzyl-2-phenyl[1-(5-morpholinylethoxy)phenyl]but-1-ene.
2,2-Dimethyl-propionic acid 4-{2-benzyl-1-[4-(2-pyrrolidin-1-yl-ethoxy-phenyl]-but-1-enyl}-phenyl ester.
4-{2-Benzyl-1-[4-(2-dimethylamino-ethoxy)-phenyl]-but-1-enyl}-phenol.
4-{2-Benzyl-1-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-but-1-enyl}-phenol.
[4-(2-Benzyl-1-phenylbut-1-enyl)-phenyl]-(3-ethoxypropyl)-amine.
3-[4-(2-Benzyl-1-phenylbut-1-enyl)-phenoxy]-propan-1-ol.
N′-[4-(2-Benzyl-1-phenylbut-1-enyl)-phenyl]-N,N-dimethylethane-1,2-diamine.
A compound as claimed in any preceding claim wherein the compound is antiosteoporotic.
A compound selected from
- 4-(2-benzyl-1-phenylbut-1-enyl)phenyl-amine
- N-[4-(2-benzyl-1-phenylbut-1 -enyl)-phenyl]-2,2,2-trifluoroacetamide
- N-[4-(2-benzyl-1-phenylbut-1-enyl)-phenyl]-2,2,2-trifluoro-N-[3-(tetrahydropyran-2-yloxy)-propyl]-acetamide
- [4-(2-Benzyl-1-phenylbut-1-enyl)-phenyl]-[3-(tetrahydropyran-2-yloxy)-propyl]-amine
- [4-(2-benzyl-1-phenylbut-1-enyl)-phenyl]-[3-(tetrahydropyran-2-yloxy)-propyl]-carbamic acid ethyl ester
- [4-(2-benzyl-1-phenylbut-1-enyl)-phenyl]-(3-hydroxypropyl)-carbamic acid ethyl ester.
A compound substantially as hereinbefore described with reference to the examples.
Dependencies are inferred from the claim text.