Estrogen receptor modulators

1. A compound of the formula:

wherein X is O;

Y is CR 1 R 2 , CH 2 CH 2 CR 1 R 2 ;

Z is CH 2 or CH 2 CH 2 ;

R 1 is hydrogen, C 1-3 alkyl;

R 2 is hydrogen, hydroxy or C 1 ;

R 3 is chloro, bromo, cyano, C 1-10 alkyl, C 3-7 cycloalkyl, aryl or heteroaryl, wherein said alkyl, cycloalkyl, aryl and heteroaryl groups are either unsubstituted or independently substituted with 1, 2 or 3 groups selected from fluoro, chloro, cyano, OR a , LR d or MLR d ;

R 4 is hydrogen;

R 5 is hydrogen or fluoro;

R 6 is OR a or O(C═O)R c ;

R 7 is hydrogen, chloro or methyl;

R 8 and R 9 are each hydrogen;

or R 8 and R 9 , when taken together with the carbon atom to which they are attached, form a carbonyl group;

R 10 is C 1-10 alkyl, or (cycloalkyl)alkyl wherein said alkyl and (cycloalkyl)alkyl groups are unsubstituted or substituted with 1-5 fluoro;

R a is hydrogen, C 1-10 -alkyl and phenyl, wherein said alkyl group is optionally substituted with a group selected from hydroxy, amino, O(C 1-4 alkyl), NH(C 1-4 alkyl), N(C 1-4 alkyl) 2 , phenyl, or 1-5 fluoro, and wherein said phenyl groups can either be unsubstituted or substituted with 1-3 substituents independently selected from C 1-4 alkyl, OH, O(C 1-4 alkyl), NH 2 , NH(C 1-4 alkyl), N(C 1-4 alkyl) 2 , halo, CN, NO 2 , CO 2 H, CO 2 (C 1-4 alkyl), C(O)H or C(O)(C 1-4 alkyl);

R b is hydrogen, C 1-10 alkyl, benzyl or phenyl, wherein said phenyl group can either be unsubstituted or substituted with 1-3 substituents independently selected from C 1-4 alkyl, OH, O(C 1-4 alkyl), NH 2 , NH(C 1-4 alkyl), N(C 1-4 alkyl) 2 , halo, CN, NO 2 , CO 2 H, CO 2 (C 1-4 alkyl), C(O)H or C(O)(C 1-4 alkyl);

R c is hydrogen, C 1-10 alkyl or phenyl, wherein said phenyl group can either be unsubstituted or substituted with 1-3 substituents independently selected from C 1-4 alkyl, OH, O(C 1-4 alkyl), NH 2 , NH(C 1-4 alkyl), N(C 1-4 alkyl) 2 , halo, CN, NO 2 , CO 2 H, CO 2 (C 1-4 alkyl), C(O)H or C(O)(C 1-4 alkyl);

or R a and R c , whether or not on the same atom, can be taken together with any attached and intervening atoms to form a 4-7 membered ring;

R d is NR b R c , OR a , CO 2 R a , O(C═O)R a , CN, NR c (C═O)R b , CONR a R c , SO 2 NR a R c or a 4-9 membered mono- or bi-cyclic N-heterocycloalkyl ring that can be optionally substituted with 1-3 C 1-3 alkyl and can be optionally interrupted by O, S, NR c , or C═O;

R e is hydrogen, C 1-6 alkyl, C 2-6 alkenyl, phenyl or phenylalkyl, wherein said alkyl, alkenyl, or phenyl group can either be unsubstituted or substituted with 1-3 substituents independently selected from C 1-3 alkyl, OH, O(C 1-4 alkyl), NH 2 , NH(C 1-4 alkyl), N(C 1-4 alkyl) 2 , halo, CN, NO 2 , CO 2 H, CO 2 (C 1-4 alkyl), C(O)H or C(O)(C 1-4 alkyl);

L is CR b R c , C 2-6 alkylene or C 2-6 alkenylene, wherein said alkylene and alkenylene linkers can be optionally interrupted by O, S, or NR c ;

M is O, S, NR c , C═O, O(C═O), (C═O)O, NR c (C═O) or (C═O)NR c ;

or a pharmaceutically acceptable salt thereof.

2. The compound of claim 1 wherein;

Y is CH 2 or CH 2 CH 2 CH 2 ;

R 1 is hydrogen;

R 2 is hydrogen;

R 3 is chloro, bromo, cyano, methyl, ethyl, trifluoromethyl, cyclopropyl, phenyl, furyl or thienyl;

R 6 is hydroxy;

R 8 and R 9 are each hydrogen;

an or a pharmaceutically acceptable salt thereof.

3. The compound of claim 1 selected from the group consisting of:

3-bromo-8a-butyl-6-hydroxy-8,8a-dihydrocyclopenta[a]inden-2(1H)-one;

(rac)-(1S,8aR)-3-bromo-8a-butyl-6-hydroxy-1-propyl-8,8a-dihydrocyclopenta[a]inden-2(1H)-one;

1,3a-diethyl-7-hydroxy-3,3a,4,5-tetrahydro-2H-cyclopenta[a]naphthalen-2-one;

3a-butyl-7-hydroxy-3,3a,4,5-tetrahydro-2H-cyclopenta[a]naphthalen-2-one;

1,6-dibromo-3a-butyl-7-hydroxy-3,3a,4,5-tetrahydro-2H-cyclopenta[a]naphthalen-2-one;

1-bromo-3a-butyl-7-hydroxy-3,3a,4,5-tetrahydro-2H-cyclopenta[a]naphthalen-2-one;

6-bromo-3a-butyl-7-hydroxy-1-methyl-3,3a,4,5-tetrahydro-2H-cyclopenta[a]naphthalen-2-one;

3a-butyl-7-hydroxy-1,6-dimethyl-3,3a,4,5-tetrahydro-2H-cyclopenta[a]naphthalen-2-one;

3a-butyl-7-hydroxy-1-methyl-3,3a,4,5-tetrahydro-2H-cyclopenta[a]naphthalen-2-one;

1-bromo-3a-butyl-6-chloro-8-fluoro-7-hydroxy-3,3a,4,5-tetrahydro-2H-cyclopenta[a]naphthalen-2-one;

10a-butyl-7-hydroxy-1,9,10,10a-tetrahydro-3(2H)-phenanthrenone;

4-bromo-10a-butyl-7-hydroxy-1,9,10,10a-tetrahydro-3(2H)-phenanthrenone;

9a-butyl-2-hydroxy-5-methyl-8,9,9a,10-tetrahydrobenzo[a]azulen-6(7H)-one;

1-bromo-7-hydroxy-3a-methyl-3,3a,4,5-tetrahydro-2H-cyclopenta[a]naphthalen-2-one;

7-hydroxy-1,3a-dimethyl-3,3a,4,5-tetrahydro-2H-cyclopenta[a]naphthalen-2-one;

1,6-dibromo-7-hydroxy-3a-methyl-3,3a,4,5-tetrahydro-2H-cyclopenta[a]naphthalen-2-one;

6-bromo-7-hydroxy-1,3a-dimethyl-3,3a,4,5-tetrahydro-2H-cyclopenta[a]naphthalen-2-one;

1-bromo-3a-ethyl-7-hydroxy-3,3a,4,5-tetrahydro-2H-cyclopenta[a]naphthalen-2-one;

3a-ethyl-7-hydroxy-1-methyl-3,3a,4,5-tetrahydro-2H-cyclopenta[a]naphthalen-2-one;

1,6-dibromo-3a-ethyl-7-hydroxy-3,3a,4,5-tetrahydro-2H-cyclopenta[a]naphthalen-2-one;

1-bromo-7-hydroxy-3a-propyl-3,3a,4,5-tetrahydro-2H-cyclopenta[a]naphthalen-2-one;

7-hydroxy-1-methyl-3a-propyl-3,3a,4,5-tetrahydro-2H-cyclopenta[a]naphthalen-2-one;

1,6-dibromo-7-hydroxy-3a-propyl-3,3a,4,5-tetrahydro-2H-cyclopenta[a]naphthalen-2-one;

1-bromo-6-chloro-3a-ethyl-7-hydroxy-3,3a,4,5-tetrahydro-2H-cyclopenta[a]naphthalen-2-one;

1-bromo-3a-butyl-6-chloro-7-hydroxy-3,3a,4,5-tetrahydro-2H-cyclopenta[a]naphthalen-2-one;

and the pharmaceutically acceptable salts thereof.

4. A pharmaceutical composition comprising a compound according to claim 1 and a pharmaceutically acceptable carrier.

5. A pharmaceutical composition made by combining a compound according to claim 1 and a pharmaceutically acceptable carrier.

6. A process for making a pharmaceutical composition comprising combining a compound according to claim 1 and a pharmaceutically acceptable carrier.