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Generated: November 18, 2017

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Title:2-phenyl-1-[4-(2-aminoethoxy)-benzyl]-indoles as estrogenic agents
Abstract: The present invention relates to new 2-Phenyl-1-[4-(2-Aminoethoxy)-Benzyl]-Indole compounds having the general structures below: ##STR00001## which are useful in treating vaginal and skin atrophy.
Inventor(s): Miller; Chris P. (Stafford, PA), Collini; Michael D. (Clifton Heights, PA), Tran; Bach D. (Baltimore, MD), Santilli; Arthur A. (Havertown, PA)
Assignee: Wyeth (Madison, NJ)
Filing Date:May 19, 2005
Application Number:11/133,113
Claims:1. A method of treating vaginal and skin atrophy in a mammal in need thereof, which comprises administering to said mammal an effective amount of a compound of formula I or II, having the structures ##STR00196## wherein: R.sub.1 is selected from H, OH or the C.sub.1 C.sub.12 esters (straight chain or branched) or C.sub.1 C.sub.12 (straight chain or branched or cyclic) alkyl ethers thereof, or halogens; or C.sub.1 C.sub.4 halogenated ethers including triflouromethyl ether and trichloromethyl ether; R.sub.2, R.sub.3, R.sub.4, R.sub.5, and R.sub.6 are independently selected from H, OH or the C.sub.1 C.sub.12 esters (straight chain or branched) or C.sub.1 C.sub.12 alkyl ethers (straight chain or branched or cyclic) thereof, halogens, or C.sub.1 C.sub.4 halogenated ethers including triflouromethyl ether and trichloromethyl ether, cyano, C.sub.1 C.sub.6 alkyl (straight chain or branched), or trifluoromethyl, with the proviso that, when R.sub.1 is H, R.sub.2 is not OH; X is selected from H, C.sub.1 C.sub.6 alkyl, cyano, nitro, trifluoromethyl, halogen; n is 2 or 3; Y is selected from: a) the moiety: ##STR00197## wherein R.sub.7 and R.sub.8 are independently selected from the group of H, C.sub.1 C.sub.6 alkyl, or phenyl optionally substituted by CN, C.sub.1 C.sub.6 alkyl(straight chain or branched), C.sub.1 C.sub.6 alkoxy (straight chain or branched), halogen, --OH, --CF.sub.3, or --OCF.sub.3; b) a five-membered saturated, unsaturated or partially unsaturated heterocycle containing up to two heteroatoms selected from the group consisting of --O--, --NH--, --N(C.sub.1C.sub.4 alkyl)-, --N.dbd., and --S(O).sub.m--, wherein m is an integer of from 0 2, optionally substituted with 1 3 substituents independently selected from the group consisting of hydrogen, hydroxyl, halo, C.sub.1 C.sub.4 alkyl, trihalomethyl, C.sub.1 C.sub.4 alkoxy, trihalomethoxy, C.sub.1 C.sub.4 acyloxy, C.sub.1 C.sub.4 alkylthio, C.sub.1 C.sub.4 alkylsulfinyl, C.sub.1 C.sub.4 alkylsulfonyl, hydroxy (C.sub.1 C.sub.4)alkyl, --CO.sub.2H--, --CN--, --CONHR.sub.1--, --NH.sub.2--, C.sub.1 C.sub.4 alkylamino, di(C.sub.1 C.sub.4)alkylamino, --NHSO.sub.2R.sub.1--, --NHCOR.sub.1--, --NO.sub.2, and phenyl optionally substituted with 1 3 (C.sub.1 C.sub.4)alkyl; c) a six-membered saturated, unsaturated or partially unsaturated heterocycle containing up to two heteroatoms selected from the group consisting of --O--, --NH--, --N(C.sub.1C.sub.4 alkyl)-, --N.dbd., and --S(O).sub.m--, wherein m is an integer of from 0 2, optionally substituted with 1 3 substituents independently selected from the group consisting of hydrogen, hydroxyl, halo, C.sub.1 C.sub.4 alkyl, trihalomethyl, C.sub.1 C.sub.4 alkoxy, trihalomethoxy, C.sub.1 C.sub.4 acyloxy, C.sub.1 C.sub.4 alkylthio, C.sub.1 C.sub.4 alkylsulfinyl, C.sub.1 C.sub.4 alkylsulfonyl, hydroxy (C.sub.1 C.sub.4)alkyl, --CO.sub.2H--, --CN--, --CONHR.sub.1--, --NH.sub.2--, C.sub.1 C.sub.4 alkylamino, di(C.sub.1 C.sub.4)alkylamino, --NHSO.sub.2R.sub.1--, --NHCOR.sub.1--, --NO.sub.2, and phenyl optionally substituted with 1 3 (C.sub.1 C.sub.4)alkyl; d) a seven-membered saturated, unsaturated or partially unsaturated heterocycle containing up to two heteroatoms selected from the group consisting of --O--, --NH--, --N(C.sub.1C.sub.4 alkyl)-, --N.dbd., and --S(O).sub.m--, wherein m is an integer of from 0 2, optionally substituted with 1 3 substituents independently selected from the group consisting of hydrogen, hydroxyl, halo, C.sub.1 C.sub.4 alkyl, trihalomethyl, C.sub.1 C.sub.4 alkoxy, trihalomethoxy, C.sub.1 C.sub.4 acyloxy, C.sub.1 C.sub.4 alkylthio, C.sub.1 C.sub.4 alkylsulfinyl, C.sub.1 C.sub.4 alkylsulfonyl, hydroxy (C.sub.1 C.sub.4)alkyl, --CO.sub.2H--, --CN--, --CONHR.sub.1--, --NH.sub.2--, C.sub.1 C.sub.4 alkylamino, di(C.sub.1 C.sub.4)alkylamino, --NHSO.sub.2R.sub.1--, --NHCOR.sub.1--, --NO.sub.2, and phenyl optionally substituted with 1 3 (C.sub.1 C.sub.4)alkyl; or e) a bicyclic heterocycle containing from 6 12 carbon atoms either bridged or fused and containing up to two heteroatoms selected from the group consisting of --O--, --NH--, --N(C.sub.1C.sub.4 alkyl)-, and --S(O).sub.m--, wherein m is an integer of from 0 2, optionally substituted with 1 3 substituents independently selected from the group consisting of hydrogen, hydroxyl, halo, C.sub.1 C.sub.4 alkyl, trihalomethyl, C.sub.1 C.sub.4 alkoxy, trihalomethoxy, C.sub.1 C.sub.4 acyloxy, C.sub.1 C.sub.4 alkylthio, C.sub.1 C.sub.4 alkylsulfinyl, C.sub.1 C.sub.4 alkylsulfonyl, hydroxy (C.sub.1 C.sub.4)alkyl, --CO.sub.2H--, --CN--, --CONHR.sub.1--, --NH.sub.2--, C.sub.1 C.sub.4 alkylamino, di(C.sub.1 C.sub.4)alkylamino, --NHSO.sub.2R.sub.1--, --NHCOR.sub.1--, --NO.sub.2, and phenyl optionally substituted with 1 3 (C.sub.1 C.sub.4) alkyl; and the pharmaceutically acceptable salts thereof.

2. The method according to claim 1 wherein: R.sub.1 is selected from H, OH or the C.sub.1 C.sub.4 esters or alkyl ethers thereof, halogen; R.sub.2, R.sub.3, R.sub.4, R.sub.5, and R.sub.6 are independently selected from H, OH or the C.sub.1 C.sub.4 esters or alkyl ethers thereof, halogen, cyano, C.sub.1 C.sub.6 alkyl, or trifluoromethyl, with the proviso that, when R.sub.1 is H, R.sub.2 is not OH; X is selected from H, C.sub.1 C.sub.6 alkyl, cyano, nitro, triflouromethyl, halogen; Y is the moiety ##STR00198## R.sub.7 and R.sub.8 are selected independently from H, C.sub.1 C.sub.6 alkyl, or combined by --(CH.sub.2)p-, wherein p is an integer of from 2 to 6, so as to form a ring, the ring being optionally substituted by up to three substituents selected from the group of hydrogen, hydroxyl, halo, C.sub.1 C.sub.4 alkyl, trihalomethyl, C.sub.1 C.sub.4 alkoxy, trihalomethoxy, C.sub.1 C.sub.4 alkylthio, C.sub.1 C.sub.4 alkylsulfinyl, C.sub.1 C.sub.4 alkylsulfonyl, hydroxy (C.sub.1 C.sub.4)alkyl, --CO.sub.2H, --CN, --CONH(C.sub.1 C.sub.4), --NH.sub.2, C.sub.1 C.sub.4 alkylamino, di(C.sub.1 C.sub.4)alkylamino, --NHSO.sub.2(C.sub.1 C.sub.4), --NHCO(C.sub.1 C.sub.4), and --NO.sub.2; or a pharmaceutically acceptable salt thereof.

3. The method according to claim 1 wherein: R.sub.1 is OH; R.sub.2, R.sub.3, R.sub.4, R.sub.5, and R.sub.6 are independently selected from H, OH or the C.sub.1 C.sub.4 esters or alkyl ethers thereof, halogen, cyano, C.sub.1 C.sub.6 alkyl, or trifluoromethyl, with the proviso that, when R.sub.1 is H, R.sub.2 is not OH; X is selected from the group of Cl, NO.sub.2, CN, CF.sub.3, or CH.sub.3; Y is the moiety ##STR00199## and R.sub.7 and R.sub.8 are concatenated together as --(CH.sub.2).sub.r--, wherein r is an integer of from 4 to 6, to form a ring optionally substituted by up to three subsituents selected from the group of hydrogen, hydroxyl, halo, C.sub.1 C.sub.4 alkyl, trihalomethyl, C.sub.1 C.sub.4 alkoxy, trihalomethoxy, C.sub.1 C.sub.4 alkylthio, C.sub.1 C.sub.4 alkylsulfinyl, C.sub.1 C.sub.4 alkylsulfonyl, hydroxy (C.sub.1 C.sub.4)alkyl, --CO.sub.2H, --CN, --CONH(C.sub.1 C.sub.4), --NH.sub.2, C.sub.1 C.sub.4 alkylamino, di(C.sub.1 C.sub.4)alkylamino, --NHSO.sub.2(C.sub.1 C.sub.4), --NHCO(C.sub.1 C.sub.4), and --NO.sub.2; or a pharmaceutically acceptable salt thereof.

4. A method of treating vaginal and skin atrophy in a mammal in need thereof, which comprises administering to said mammal an effective amount of a compound of formula I or II, having the structures ##STR00200## wherein: R.sub.1 is selected from H, OH or the C.sub.1 C.sub.4 esters or alkyl ethers thereof, halogen; R.sub.2, R.sub.3, R.sub.4, R.sub.5, and R.sub.6 are independently selected from H, OH or the C.sub.1 C.sub.4 esters or alkyl ethers thereof, halogen, cyano, C.sub.1 C.sub.6 alkyl, or trifluoromethyl, with the proviso that, when R.sub.1 is H, R.sub.2 is not OH; X is selected from H, C.sub.1 C.sub.6 alkyl, cyano, nitro, triflouromethyl, halogen; n is 2 or 3; and Y is the moiety ##STR00201## R.sub.7 and R.sub.8 are selected independently from H, C.sub.1 C.sub.6 alkyl, or combined by --(CH.sub.2)p-, wherein p is an integer of from 2 to 6, so as to form a ring, the ring being optionally substituted by up to three substituents selected from the group of hydrogen, hydroxyl, halo, C.sub.1 C.sub.4 alkyl, trihalomethyl, C.sub.1 C.sub.4 alkoxy, trihalomethoxy, C.sub.1 C.sub.4 alkylthio, C.sub.1 C.sub.4 alkylsulfinyl, C.sub.1 C.sub.4 alkylsulfonyl, hydroxy (C.sub.1 C.sub.4)alkyl, --CO.sub.2H, --CN, --CONH(C.sub.1 C.sub.4), --NH.sub.2, C.sub.1 C.sub.4 alkylamino, di(C.sub.1 C.sub.4)alkylamino, --NHSO.sub.2(C.sub.1 C.sub.4), --NHCO(C.sub.1 C.sub.4), and --NO.sub.2; or a pharmaceutically acceptable salt thereof.

5. The method according to claim 4 wherein: R.sub.1 is OH; R.sub.2, R.sub.3, R.sub.4, R.sub.5, and R.sub.6 are independently selected from H, OH or the C.sub.1 C.sub.4 esters or alkyl ethers thereof, halogen, cyano, C.sub.1 C.sub.6 alkyl, or trifluoromethyl, with the proviso that, when R.sub.1 is H, R.sub.2 is not OH; X is selected from the group of Cl, NO.sub.2, CN, CF.sub.3, or CH.sub.3; Y is the moiety ##STR00202## and R.sub.7 and R.sub.8 are concatenated together as --(CH.sub.2).sub.r--, wherein r is an integer of from 4 to 6, to form a ring optionally substituted by up to three subsituents selected from the group of hydrogen, hydroxyl, halo, C.sub.1 C.sub.4 alkyl, trihalomethyl, C.sub.1 C.sub.4 alkoxy, trihalomethoxy, C.sub.1 C.sub.4 alkylthio, C.sub.1 C.sub.4 alkylsulfinyl, C.sub.1 C.sub.4 alkylsulfonyl, hydroxy (C.sub.1 C.sub.4)alkyl, --CO.sub.2H, --CN, --CONH(C.sub.1 C.sub.4), --NH.sub.2, C.sub.1 C.sub.4 alkylamino, di(C.sub.1 C.sub.4)alkylamino, --NHSO.sub.2(C.sub.1 C.sub.4), --NHCO(C.sub.1 C.sub.4), and --NO.sub.2; or a pharmaceutically acceptable salt thereof.

6. The method according to claim 4, wherein the compound is 1-[4-(2-azepan-1-yl-ethoxy)-benzyl]-2-(4-hydroxy-phenyl)-3-methyl-1H-indo- l-5-ol or a pharmaceutically acceptable salt thereof.

7. The method according to claim 4, wherein the compound is 2-(4-hydroxy-phenyl)-3-methyl-1-[4-(2-piperidin-1-yl-ethoxy)-benzyl]-1H-i- ndol-5-ol or a pharmaceutically acceptable salt thereof.
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