Claims
- 1. A method of lowering cholesterol levels 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 wherein:R1 is selected from H, OH or the C1-C12 esters (straight chain or branched) or C1-C12 (straight chain or branched or cyclic) alkyl ethers thereof, or halogens; or C1-C4 halogenated ethers including triflouromethyl ether and trichloromethyl ether, R2, R3, R4, R5, and R6 are independently selected from H, OH or the C1-C12 esters (straight chain or branched) or C1-C12 alkyl ethers (straight chain or branched or cyclic) thereof, halogens, or C1-C4 halogenated ethers including trifluoromethyl ether and trichloromethyl ether, cyano, C1-C6 alkyl (straight chain or branched), or trifluoromethyl, with the proviso that, when R1 is H, R2 is not OH, X is selected from H, C1-C6 alkyl, cyano, nitro, trifluoromethyl, halogen; n is 2 or 3; Y is selected from: a) the moiety: wherein R7 and R8 are independently selected from the group of H, C1-C6 alkyl, or phenyl optionally substituted by CN, C1-C6 alkyl (straight chain or branched), C1-C6 alkoxy (straight chain or branched), halogen, —OH, —CF3 or —OCF3; b) a five-membered saturated, unsaturated or partially unsaturated heterocycle containing up to two heteroatoms selected from the group consisting of —O—, —NH—, —N(C1C4 alkyl)—, —N═, and —S(O)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, C1-C4 alkyl, trihalomethyl, C1-C4 acyloxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 akylsulfonyl, hydroxy (C1-C4)alkyl, —CO2H—, —CN—, —CONHR1—, —NH2—, C1-C4 alkylamino, di(C1-C4)alkylamino, —NHSO2R1—, —NHCOR1—, —NO2, and phenyl optionally substituted with 1-3 (C1-C4)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(C1C4 alkyl)—, —N═, and —S(O)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, C1-C4 alkyl, trihalomethyl, C1-C4 alkoxy, trihalomethoxy, C1-C4 acyloxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, hydroxy (C1-C4)alkyl, —CO2H—, —CN—, —CONHR1—, —NH2—, C1-C4 alkylamino, di(C1-C4)alkylamino, —NHSO2R1—, —NHCOR1—, —NO2, and phenyl optionally substituted with 1-3 (C1-C4)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(C1C4 alkyl)—, —N═, and —S(O)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, C1-C4 alkyl, trihalomethyl, C1-C4 alkoxy, trihalomethoxy, C1-C4 acyloxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, hydroxy (C1-C4)alkyl, —CO2H—, —CN—, —CONHR1—, —NH2—, C1-C4 alkylamino, di(C1-C4)alkylamino, —NHSO2R1—, —NHCOR1—, —NO2, and phenyl optionally substituted with 1-3 (C1-C4)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(C1C4 alkyl)—, and —S(O)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, C1-C4 alkyl, trihalomethyl, C1-C4 alkoxy, trihalomethoxy, C1-C4 acyloxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, hydroxy (C1-C4)alkyl, —CO2H—, —CN—, —CONHR1—, —NH2—, C1-C4 alkylamino, di(C1-C4)alkylamino, —NHSO2R1—, —NHCOR1—, —NO2, and phenyl optionally substituted with 1-3 (C1-C4) alkyl; or a pharmaceutically acceptable salt thereof.
- 2. The method according to claim 1 wherein:R1 is selected from H, OH or the C1-C4 esters or alkyl ethers thereof, halogen; R2, R3, R4, R5, and R6 are independently selected from H, OH or the C1-C4 esters or alkyl esters thereof, halogen, cyano, C1-C6 alkyl, or trifluoromethyl, with the proviso that, when R1 is H, R2 is not OH; X is selected from H, C1-C6 alkyl, cyano, nitro, triflouromethyl, halogen; Y is the moiety R7 and R8 are selected independently from H, C1-C6 alkyl, or combined by —(CH2)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, C1-C4 alkyl, trihalomethyl, C1-C4 alkoxy, trihalomethoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, hydroxy (C1-C4)alkyl, —CO2H, —CN, —CONH(C1-C4), —NH2, C1-C4 alkylamino, di(C1-C4)alkylamino, —NHSO2(C1-C4), —NHCO(C1-C4), and —NO2; or a pharmaceutically acceptable salt thereof.
- 3. The method according to claim 1 wherein:R1 is OH; R2, R3, R4, R5, and R6 are independently selected from H, OH or the C1-C4 esters or alkyl ethers thereof, halogen, cyano, C1-C6 alkyl, or trifluoromethyl, with the proviso that, when R1 is H, R2 is not OH; X is selected from the group of Cl, NO2, CN, CF3, or CH3; Y is the moiety R7 and R8 are concatenated together as —(CH2)r—, wherein r is an integer of from 4 to 6, to form a ring optionally substituted by up to three substituents selected from the group of hydrogen, hydroxyl, halo, C1-C4 alkyl, trihalomethyl, C1-C4 alkoxy, trihalomethoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, hydroxy (C1-C4)alkyl, —CO2H, —CH, —CONH(C1-C4), —NH2, C1-C4 alkylamino, di(C1-C4)alkylamino, —NHSO2(C1-C4), —NHCO(C1-C4) and —NO2; or a pharmaceutically acceptable salt thereof.
- 4. The method according to claim 1, wherein the compound is 1-[4-(2-azepan-1-yl-ethoxy)-benzyl]-2-(4-hydroxy-phenyl)-3-methyl-1H-indol-5-ol or a pharmaceutically acceptable salt thereof.
- 5. The method according to claim 1, wherein the compound is 2-(4-hydroxy-phenyl)-3-methyl-1-[4-(2-piperidin-1-yl-ethoxy)-benzyl]-1H-indol-5-ol or a pharmaceutically acceptable salt thereof.
Parent Case Info
This application is a continuation application of U.S. Ser. No. 10/617,096, filed Jul. 10, 2003, which is a continuation application of U.S. Ser. No. 10/192,069, filed Jul. 10, 2002 now abandoned, which is a continuation application of U.S. Ser. No. 09/974,416, filed Oct. 10, 2001 now abandoned, which is a divisional application of U.S. Ser. No. 09/388,581, filed Sep. 2, 1999 now U.S. Pat. No. 6,326,367, which is a divisional application of U.S. Ser. No. 08/833,271 (now U.S. Pat. No. 5,998,402) filed Apr. 4, 1997, which claims priority from U.S. Provisional Application No. 60/015,553, filed Apr. 19, 1996.
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Provisional Applications (1)
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Number |
Date |
Country |
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60/015553 |
Apr 1996 |
US |
Continuations (3)
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Number |
Date |
Country |
Parent |
10/617096 |
Jul 2003 |
US |
Child |
10/720504 |
|
US |
Parent |
10/192069 |
Jul 2002 |
US |
Child |
10/617096 |
|
US |
Parent |
09/974416 |
Oct 2001 |
US |
Child |
10/192069 |
|
US |