Claims
- 1. A compound of formula (I): whereinR1 is OR7; R2 is aryl or aryl(C1-C4)alkyl; R3 is hydrogen, (C1-C4)alkyl, (C2-C4)alkenyl or (C2-C4)alkynyl; R4 and R5 are independently hydrogen, halo, CN, OR9, COOR10, arylSO2—, or —CH2NHR11; R6 is hydrogen, (C1-C4)alkyl, (C1-C4)alkenyl, (C1-C4)alkynyl, aryl, or aryl(C1-C4)alkyl; R7 is hydrogen, (C1-C4)alkyl, (C1-C5)alkanoyl, arylcarbonyl, or aryl (C1-C5)alkanoyl; each R8 is independently hydrogen, (C1-C4)alkyl, (C1-C4)alkanoyl, aryl, aryl(C1-C4)alkyl, or arylcarbonyl; R9 is hydrogen, (C1-C4)alkyl, (C1-C5)alkanoyl, or arylcarbonyl; R10 is hydrogen or (C1-C4)alkyl; and R11 is hydrogen or (C1-C4)alkyl; wherein any aryl in R1, R2, and R6-R9 may optionally be substituted with 1, 2, or 3 substituents independently selected from the group consisting of halo, CF3, (C1-C4)alkoxy, (C1-C4)alkyl, (C1-C4)alkenyl, (C1-C4)alkynyl, amino, nitro, cyano, and aryl; or a pharmaceutically acceptable salt thereof.
- 2. A compound of formula (I): whereinR1 is hydrogen, OR7, or N(R8)2; R2 is aryl or aryl(C1-C4)alkyl; R3 is hydrogen, (C1-C4)alkyl, (C2-C4)alkenyl or (C2-C4)alkynyl; R4 and R5 are independently hydrogen, halo, CN, OR9, COOR10, arylSO2—, or —CH2NHR11;s R6 is hydrogen, (C1-C4)alkyl, (C1-C4)alkenyl, (C1-C4)alkynyl, aryl, or aryl(C1-C4)alkyl; R7 is hydrogen, (C1-C4)alkyl, (C1-C5)alkanoyl, arylcarbonyl, or aryl (C1-C5)alkanoyl; each R8 is independently hydrogen, (C1-C4)alkyl, (C1-C4)alkanoyl, aryl, aryl(C1-C4)alkyl, or arylcarbonyl; R9 is hydrogen, (C1-C4)alkyl, (C1-C5)alkanoyl, or arylcarbonyl; R10 is hydrogen or (C1-C4)alkyl; and R11 is hydrogen or (C1-C4)alkyl; wherein any aryl in R1, R2, and R6-R9 may optionally be substituted with 1, 2, or 3 substituents independently selected from the group consisting of halo, CF3, (C1-C4)alkoxy, (C1-C4)alkyl, (C1-C4)alkenyl, (C1-C4)alkynyl, amino, nitro, cyano, and aryl; or a pharmaceutically acceptable salt thereof.
- 3. A compound of formula (I): whereinR1 is OR7, or N(R8)2; R2 is aryl or aryl(C1-C4)alkyl; R3 is hydrogen, (C1-C4)alkyl, (C2-C4)alkenyl or (C2-C4)alkynyl; R4 and R5 are independently hydrogen, halo, CN, OR9, COOR10, arylSO2—, or —CH2NHR11; R6 is hydrogen, (C1-C4)alkyl, (C1-C4)alkenyl, (C1-C4)alkynyl, aryl, or aryl(C1-C4)alkyl; R7 is hydrogen, (C1-C4)alkyl, (C1-C5)alkanoyl, arylcarbonyl, or aryl (C1-C5)alkanoyl; each R8 is independently hydrogen, (C1-C4)alkyl, (C1-C4)alkanoyl, aryl, aryl(C1-C4)alkyl, or arylcarbonyl; R9 is hydrogen, (C1-C4)alkyl, (C1-C5)alkanoyl, or arylcarbonyl; R10 is hydrogen or (C1-C4)alkyl; and R11 is hydrogen or (C1-C4)alkyl; wherein any aryl in R1, R2, and R6-R9 may optionally be substituted with 1, 2, or 3 substituents independently selected from the group consisting of halo, CF3, (C1-C4)alkoxy, (C1-C4)alkyl, (C1-C4)alkenyl, (C1-C4)alkynyl, amino, nitro, cyano, and aryl; or a pharmaceutically acceptable salt thereof.
- 4. A compound of formula (I): whereinR1 is hydrogen, OR7, or N(R8)2; R2 is aryl or aryl(C1-C4)alkyl; wherein the aryl is substituted with 1, 2, or 3 substituents independently selected from the group consisting of halo, CF3, (C1-C4)alkoxy, (C1-C4)alkenyl, (C1-C4)alkynyl, amino, nitro and cyano; R3 is hydrogen, (C1-C4)alkyl, (C2-C4)alkenyl or (C2-C4)alkynyl; R4 and R5 are independently hydrogen, halo, CN, OR9, COOR10, arylSO2—, or —CH2NHR11; R6 is hydrogen, (C1-C4)alkyl, (C1-C4)alkenyl, (C1-C4)alkynyl, aryl, or aryl(C1-C4)alkyl; R7 is hydrogen, (C1-C4)alkyl, (C1-C5)alkanoyl, arylcarbonyl, or aryl (C1-C5)alkanoyl; each R8 is independently hydrogen, (C1-C4)alkyl, (C1-C4)alkanoyl, aryl, aryl(C1-C4)alkyl, or arylcarbonyl; R9 is hydrogen, (C1-C4)alkyl, (C1-C5)alkanoyl, or arylcarbonyl; R10 is hydrogen or (C1-C4)alkyl; and R11 is hydrogen or (C1-C4)alkyl; wherein any aryl in R2, and R6-R9 may optionally be substituted with 1, 2, or 3 substituents independently selected from the group consisting of halo, CF3, (C1-C4)alkoxy, (C1-C4)alkyl, (C1-C4)alkenyl, (C1-C4)alkynyl, amino, nitro, cyano, and aryl; or a pharmaceutically acceptable salt thereof.
- 5. A compound of formula (I): whereinR1 is hydrogen, aryl, aryl(C1-C4)alkyl, (C1-C4)alkyl, OR7, or N(R8)2; R2 is aryl or aryl(C1-C4)alkyl; R3 is (C1-C4)alkyl, (C2-C4)alkenyl or (C2-C4)alkynyl; R4 and R5 are independently hydrogen, halo, CN, OR9, COOR10, arylSO2—, or —CH2NHR11; R6 is hydrogen, (C1-C4)alkyl, (C1-C4)alkenyl, (C1-C4)alkynyl, aryl, or aryl(C1-C4)alkyl; R7 is hydrogen, (C1-C4)alkyl, (C1-C5)alkanoyl, arylcarbonyl, or aryl (C1-C5)alkanoyl; each R8 is independently hydrogen, (C1-C4)alkyl, (C1-C4)alkanoyl, aryl, aryl(C1-C4)alkyl, or arylcarbonyl; R9 is hydrogen, (C1-C4)alkyl, (C1-C5)alkanoyl, or arylcarbonyl; R10 is hydrogen or (C1-C4)alkyl; and R11 is hydrogen or (C1-C4)alkyl; wherein any aryl in R1, R2, and R6-R9 may optionally be substituted with 1, 2, or 3 substituents independently selected from the group consisting of halo (preferably I or Cl), CF3, (C1-C4)alkoxy, (C1-C4)alkyl, (C1-C4)alkenyl, (C1-C4)alkynyl, amino, nitro, cyano, and aryl; or a pharmaceutically acceptable salt thereof.
- 6. The compound of claim 5 wherein R3 is (C2-C4)alkenyl or (C2-C4)alkynyl.
- 7. The compound of claim 5 wherein R3 is (C1-C4)alkyl or (C2-C4)alkynyl.
- 8. A compound of formula (I): whereinR1 is OR7; R2 is aryl or aryl(C1-C4)alkyl; R3 is hydrogen, (C1-C4)alkyl, (C2-C4)alkenyl or (C2-C4)alkynyl; R4 and R5 are independently hydrogen, halo, CN, OR9, COOR10, arylSO2—, or —CH2NHR11; R6 is hydrogen, (C1-C4)alkyl, (C1-C4)alkenyl, (C1-C4)alkynyl, aryl, or aryl(C1-C4)alkyl; R7 is (C1-C5)alkanoyl, arylcarbonyl, or aryl (C1-C5)alkanoyl, each R8 is independently hydrogen, (C1-C4)alkyl, (C1-C4)alkanoyl, aryl, aryl(C1-C4)alkyl, or arylcarbonyl; R9 is hydrogen, (C1-C4)alkyl, (C1-C5)alkanoyl, or arylcarbonyl; R10 is hydrogen or (C1-C4)alkyl; and R11 is hydrogen or (C1-C4)alkyl; wherein any aryl in R1, R2, and R6-R9 may optionally be substituted with 1, 2, or 3 substituents independently selected from the group consisting of halo, CF3, (C1-C4)alkoxy, (C1-C4)alkyl, (C1-C4)alkenyl, (C1-C4)alkynyl, amino, nitro, cyano, and aryl; or a pharmaceutically acceptable salt thereof.
- 9. A compound of formula (I): whereinR1 is hydrogen, aryl, aryl(C1-C4)alkyl, (C1-C4)alkyl, OR7, or N(R8)2; R2 is aryl or aryl(C1-C4)alkyl; R3 is hydrogen, (C1-C4)alkyl, (C2-C4)alkenyl or (C2-C4)alkynyl; one of R4 and R5 is hydrogen, and the other is halo, CN, OR9, COOR10, arylSO2—, or —CH2NHR11; R6 is hydrogen, (C1-C4)alkyl, (C1-C4)alkenyl, (C1-C4)alkynyl, aryl, or aryl(C1-C4)alkyl; R7 is hydrogen, (C1-C4)alkyl, (C1-C5)alkanoyl, arylcarbonyl, or aryl (C1-C5)alkanoyl; each R8 is independently hydrogen, (C1-C4)alkyl, (C1-C4)alkanoyl, aryl, aryl(C1-C4)alkyl, or arylcarbonyl; R9 is hydrogen, (C1-C4)alkyl, (C1-C5)alkanoyl, or arylcarbonyl; R10 is hydrogen or (C1-C4)alkyl; and R11 is hydrogen or (C1-C4)alkyl; wherein any aryl in R1, R2, and R6-R9 may optionally be substitited with 1, 2, or 3 substituents independently selected from the group consistng of halo (preferably I or Cl), CF3, (C1-C4)alkoxy, (C1-C4)alkyl, (C1-C4)alkenyl, (C1-C4)alkynyl, amino, nitro cyano, and aryl; or a pharmaceutically acceptable salt thereof.
- 10. The compound of any one of claims 1-9, wherein the carbon designated “a” has the (R) stereochemistry and the carbon designated “b” has the (S) stereochemistry.
- 11. The compound (1R,5S)-2β-phenyl-3α-(p-tolyl)tropane; or a pharmaceutically acceptable salt thereof.
- 12. A pharmaceutical composition comprising an effective amount of a compound of formula (I) or a pharmaceutically acceptable salt thereof as defined in any one of claims 1-9 in combination with a pharmaceutically acceptable diluent or carrier.
- 13. A compound of formula (XI): whereinR1 is OR7 where R7 is H, (C1-C4)alkyl, (C1-C4)alkylC(O)—, (C5-C7)arylC(O)—, or NHR8 where R8 is H, (C1-C4)alkyl, (C1-C4)alkyl(CO)— or (C5-C7)arylC(O)—; R2 is phenyl or benzyl, each optionally substituted with halo, CF3, (C1-C4)alkoxy, (C1-C4)alkyl, (C1-C4)alkenyl, (C1-C4)alkynyl, amino, nitro or (C5-C7)aryl; R5 is (C1-C4)alkyl, (C1-C4)alkenyl or (C1-C4)alkynyl; R4 and R5 are independently H, halo, CN, OR9 where R9 is H, (C1-C4)alkyl, (C1-C4)alkylC(O)—, (C5-C7)arylC(O)—; COOR10 where R10 is H or (C1-C4)alkyl; or CH2NHR11 where R11 is H or (C1-C4)alkyl; and R6 is H, (C1-C4)alkyl, (C1-C4)alkenyl, (C1-C4)alkynyl or benzyl; or a stereoisomer thereof; or a pharmaceutically acceptable salt thereof.
- 14. A compound of formula (XI): whereinR1 is H, OR7 where R7 is H, (C1-C4)alkyl, (C1-C4)alkylC(O)—, (C5-C7)arylC(O)—; or NHR8 where R8 is H, (C1-C4)alkyl, (C1-C4)alkyl(CO)— or (C5-C7)arylC(O)—; R2 is phenyl or benzyl, each optionally substituted with halo, CF3, (C1-C4)alkoxy, (C1-C4)alkyl, (C1-C4)alkenyl, (C1-C4)alkynyl, amino, nitro or (C5-C7)aryl; R3 is (C1-C4)alkenyl or (C1-C4)alkynyl; R4 and R5 are independently H, halo, CN, OR9 where R9 is H, (C1-C4)alkyl, (C1-C4)alkylC(O)—, (C5-C7)arylC(O)—; COOR10 where R10 is H or (C1-C4)alkyl; or CH2NHR11 where R11 is H or (C1-C4)alkyl; and R6 is H, (C1-C4)alkyl, (C1-C4)alkenyl, (C1-C4)alkynyl or benzyl; or a stereoisomer thereof; or a pharmaceutically acceptable salt thereof.
- 15. The compound of claim 14 wherein R2 is phenyl.
- 16. The compound of claim 15 wherein the phenyl is substituted with I or Cl.
- 17. The compound of claim 14 wherein R6 is (C1-C4)alkyl.
Parent Case Info
This application claims benefit of Provisional application No. 60/032,231, filed Dec. 2, 1996.
PCT Information
Filing Document |
Filing Date |
Country |
Kind |
PCT/US97/21706 |
|
WO |
00 |
Publishing Document |
Publishing Date |
Country |
Kind |
WO98/24788 |
6/11/1998 |
WO |
A |
US Referenced Citations (1)
Number |
Name |
Date |
Kind |
5935953 |
Kuhar et al. |
Aug 1999 |
A |
Provisional Applications (1)
|
Number |
Date |
Country |
|
60/032231 |
Dec 1996 |
US |