Claims
- 1. A compound represented by the formula: ##STR9## in which: X is H, Cl, Br, F, I, CF.sub.3, C.sub.1-6 alkyl, COR.sup.10, CO.sub.2 R.sup.10, CONR.sup.16 R.sup.11, CN, NO.sub.2, NR.sup.12 R.sup.13, OR.sup.12, SC.sub.1-4 alkyl, S(CH.sub.2).sub.0-6 aryl, SCF.sub.3, or any accessible combination thereof of up to three substituents;
- R is H, C.sub.1-6 alkyl, or C.sub.3-5 alkenyl;
- R.sup.1 is H or C.sub.1-6 alkyl;
- R.sup.10 is C.sub.1-6 alkyl or (CH.sub.2).sub.0-6 aryl;
- R.sup.11 and R.sup.16 independently are H, C.sub.1-6 alkyl, or (CH.sub.2).sub.0-6 aryl;
- R.sup.12 is H, C.sub.1-6 alkyl, COR.sup.14, or SO.sub.2 R.sup.15 ;
- R.sup.13 is H or C.sub.1-6 alkyl;
- R.sup.14 and R.sup.15 independently are C.sub.1-6 alkyl or (CH.sub.2).sub.0-6 aryl;
- Y and Z independently are H, NO.sub.2, C.sub.1-6 alkyl, CH.sub.2 CH.sub.2 OH, CN, CH.sub.2 OR.sup.2, CH.sub.2 SR.sup.2, COR.sup.2, CO.sub.2 R.sup.2, CONR.sup.3 R.sup.4, SO.sub.2 NR.sup.3 R.sup.4, SO.sub.3 R.sup.2, SO.sub.2 R.sup.5, SOR.sup.5, P(O)(OR.sup.3)(OR.sup.4), P(O)R.sup.5 (OR.sup.3), P(O)R.sup.5 R.sup.6, P(O)(OR.sup.2)NR.sup.3 R.sup.4, P(O)(NR.sup.3 R.sup.4).sub.2, P(O)R.sup.5 (NR.sup.3 R.sup.4), halo, CF.sub.3, or (CH.sub.2).sub.0-6 aryl;
- R.sup.2, R.sup.3, and R.sup.4 independently are H, C.sub.1-6 alkyl, C.sub.3-5 alkenyl, or (CH.sub.2).sub.0-6 aryl; and
- R.sup.5 and R.sup.6 independently are C.sub.1-6 alkyl, C.sub.3-5 alkenyl, or (CH.sub.2).sub.0-6 aryl; or a pharmaceutically acceptable salt thereof.
- 2. A compound of claim 1 having the formula: ##STR10## in which: X is H, Cl, Br, F, I, CF.sub.3, C.sub.1-6 alkyl, COR.sup.10, CO.sub.2 R.sup.10, CONR.sup.16 R.sup.11, CN, NO.sub.2, NR.sup.12 R.sup.13, OR.sup.12, SC.sub.1-46 alkyl, S(CH.sub.2).sub.0-6 aryl, or SCF.sub.3 ;
- R is H, C.sub.1-6 alkyl, or C.sub.3-5 alkenyl;
- R.sup.1 is H or C.sub.1-6 alkyl;
- R.sup.10 is C.sub.1-6 alkyl or (CH.sub.2).sub.0-6 aryl;
- R.sup.11 and R.sup.16 independently are H, C.sub.1-6 alkyl, or (CH.sub.2).sub.0-6 aryl;
- R.sup.12 is H, C.sub.1-6 alkyl, COR.sup.14, or SO.sub.2 R.sup.15 ;
- R.sup.13 is H or C.sub.1-6 alkyl;
- R.sup.14 and R.sup.15 independently are C.sub.1-6 alkyl or (CH.sub.2).sub.0-6 aryl;
- Y and Z independently are H, NO.sub.2, C.sub.1-6 alkyl, CH.sub.2 CH.sub.2 OH, CN, CH.sub.2 OR.sup.2, CH.sub.2 SR.sup.2, COR.sup.2, CO.sub.2 R.sup.2, CONR.sup.3 R.sup.4, SO.sub.2 NR.sup.3 R.sup.4, SO.sub.3 R.sup.2, SO.sub.2 R.sup.5, SOR.sup.5, P(O)(OR.sup.3)(OR.sup.4), P(O)R.sup.5 (OR.sup.3), P(O)R.sup.5 R.sup.6, P(O)(OR.sup.2)NR.sup.3 R.sup.4, P(O)(NR.sup.3 R.sup.4).sub.2, P(O)R.sup.5 (NR.sup.3 R.sup.4), halo, CF.sub.3, or (CH.sub.2).sub.0-6 aryl;
- R.sup.2, R.sup.3, and R.sup.4 independently are H, C.sub.1-6 alkyl, C.sub.3-5 alkenyl, or (CH.sub.2).sub.0-6 aryl; and
- R.sup.5 and R.sup.6 independently are C.sub.1-6 alkyl, C.sub.3-5 alkenyl, or (CH.sub.2).sub.0-6 aryl; or a pharmaceutically acceptable salt thereof.
- 3. A compound of claim 2 wherein X is Cl, Br, F, or I.
- 4. A compound of claim 3 wherein R is CH.sub.3 or H.
- 5. A compound of claim 4 that is 7-chloro-2-ethenyl-3,4,5,6-tetrahydro-4-methylthieno[4,3,2-ef][3]benzazepine, or a pharmaceutically acceptable salt thereof.
- 6. A compound of claim 4 that is:
- ethyl (E)-3-(7-chloro-3,4,5,6-tetrahydro-4-methylthieno[4,3,2-ef][3]benzazepin-2-yl)-2-propenoate;
- ethyl (E)-3-(7-chloro-3,4,5,6-tetrahydro-4-methylthieno[4,3,2-ef][3]benzazepin-2-yl)-2-methyl-2-propenoate;
- (E)-3-(7-chloro-3,4,5,6-tetrahydro-4-methylthieno[4,3,2-ef][3]benzazepin-2-yl)-2-propenamide;
- (E)-3-(7-chloro-3,4,5,6-tetrahydro-4-methylthieno[4,3,2-ef][3]benzazepin-2-yl)-N-methyl-2-propenamide;
- (E)-3-(7-chloro-3,4,5,6-tetrahydro-4-methylthieno[4,3,2-ef][3]benzazepin-2-yl)-N,N-dimethyl-2-propenamide;
- (E)-3-(7-chloro-3,4,5,6-tetrahydro-4-methylthieno[4,3,2-ef][3]benzazepin-2-yl)-2-propen-1-ol;
- 7-chloro-2-ethenyl-3,4,5,6-tetrahydrothieno[4,3,2-ef][3]benzazepine;
- ethyl (E/Z)-3-(7-chloro-3,4,5,6-tetrahydro-4-methylthieno[4,3,2-ef][3]benzazepin-2-yl)-2-phenyl-2-propenoate;
- (E)-3-(7-chloro-3,4,5,6-tetrahydro-4-methylthieno[4,3,2-ef][3]benzazepin-2-yl)-2-phenyl-2-propenenitrile;
- 7-chloro-3,4,5,6-tetrahydro-4-methyl-2-(1-methylethenyl)thieno[4,3,2 -ef][3]benzazepine; or
- 7-chloro-2-propenyl-3,4,5,6-tetrahydrothieno[4,3,2-ef][3]benzazepine;
- or a pharmaceutically acceptable salt thereof.
- 7. A pharmaceutical composition comprising a compound of claim 1 and a suitable pharmaceutical carrier.
- 8. A pharmaceutical composition of claim 7 wherein the compound is 7-chloro-2-ethenyl-3,4,5,6-tetrahydro-4-methylthieno[4,3,2-ef][3]benzazepine.
- 9. A pharmaceutical composition of claim 7 wherein the compound is:
- ethyl (E)-3-(7-chloro-3,4,5,6-tetrahydro-4-methylthieno[4,3,2-ef][3]benzazepin-2-yl)-2-propenoate;
- ethyl (E)-3-(7-chloro-3,4,5,6-tetrahydro-4-methylthieno[4,3,2-ef][3]benzazepin-2-yl)-2-methyl-2-propenoate;
- (E)-3-(7-chloro-3,4,5,6-tetrahydro-4-methylthieno[4,3,2-ef][3]benzazepin-2-yl)-2-propenamide;
- (E)-3-(7-chloro-3,4,5,6-tetrahydro-4-methylthieno[4,3,2-ef][3]benzazepin-2-yl)-N-methyl-2-propenamide;
- (E)-3-(7-chloro-3,4,5,6-tetrahydro-4-methylthieno[4,3,2-ef][3]benzazepin-2-yl)-N,N-dimethyl-2-propenamide;
- (E)-3-(7-chloro-3,4,5,6-tetrahydro-4-methylthieno[4,3,2-ef][3]benzazepin-2-yl)-2-propen-1-ol;
- 7-chloro-2-ethenyl-3,4,5,6-tetrahydrothieno[4,3,2-ef][3]benzazepine;
- ethyl (E/Z)-3-(7-chloro-3,4,5,6-tetrahydro-4-methylthieno[4,3,2-ef][3]benzazepin-2-yl)-2-phenyl-2-propenoate;
- (E)-3-(7-chloro-3,4,5,6-tetrahydro-4-methylthieno[4,3,2-ef][3]benzazepin-2-yl)-2-phenyl-2-propenenitrile;
- 7-chloro-3,4,5,6-tetrahydro-4-methyl-2-(1-methylethenyl)thieno[4,3,2-ef][3]benzazepine; or
- 7-chloro-2-propenyl-3,4,5,6-tetrahydrothieno[4,3,2-ef][3]benzazepine.
- 10. A method of antagonizing .alpha.-adrenergic receptors in mammals that comprises administering to a subject in need thereof an effective amount of a compound of claim 1.
- 11. A method of claim 10 wherein the compound is 7-chloro-2-ethenyl-3,4,5,6-tetrahydro-4-methylthieno[4,3,2-ef][3]benzazepine.
- 12. A method of claim 10 wherein the compound is:
- ethyl (E)-3-(7-chloro-3,4,5,6-tetrahydro-4-methylthieno[4,3,2-ef][3]benzazepin-2-yl)-2-propenoate;
- ethyl (E)-3-(7-chloro-3,4,5,6-tetrahydro-4-methylthieno-[4,3,2-ef][3]benzazepin-2-yl)-2-methyl-2-propenoate;
- (E)-3-(7-chloro-3,4,5,6-tetrahydro-4-methylthieno[4,3,2-ef][3]benzazepin-2-yl)-2-propenamide;
- (E)-3-(7-chloro-3,4,5,6-tetrahydro-4-methylthieno[4,3,2-ef][3]benzazepin-2-yl)-N-methyl-2-propenamide;
- (E)-3-(7-chloro-3,4,5,6-tetrahydro-4-methylthieno[4,3,2-ef][3]benzazepin-2-yl)-N,N-dimethyl-2-propenamide;
- (E)-3-(7-chloro-3,4,5,6-tetrahydro-4-methylthieno[4,3,2-ef][3]benzazepin-2-yl)-2-propen-1-ol;
- 7-chloro-2-ethenyl-3,4,5,6-tetrahydrothieno[4,3,2-ef][3]benzazepine;
- ethyl (E/Z)-3-(7-chloro-3,4,5,6-tetrahydro-4-methylthieno[4,3,2-ef][3]benzazepin-2-yl-2-phenyl-2-propenoate;
- (E)-3-(7-chloro-3,4,5,6-tetrahydro-4-methylthieno[4,3,2-ef][3]benzazepin-2-yl-2-phenyl-2-propenenitrile;
- 7-chloro-3,4,5,6-tetrahydro-4-methyl-2-(1-methylethenyl)thieno[4,3,2-ef][3]benzazepine; or
- 7-chloro-2-propenyl-3,4,5,6-tetrahydrothieno[4,3,2-ef][3]benzazepine.
- 13. A method of reducing blood pressure in mammals that comprises administering to a subject in need thereof an effective amount of a compound of claim 1.
- 14. A method of treating benign prostatic hypertrophy in mammals that comprises administering to a subject in need thereof an effective amount of a compound of claim 1.
- 15. A method of treating peripheral vascular disease in mammals that comprises administering to a subject in need thereof an effective amount of a compound of claim 1.
- 16. A method of treating congestive heart failure in mammals that comprises administering to a subject in need thereof an effective amount of a compound of claim 1.
Parent Case Info
This application is a continuation-in-part of U.S. Ser. No. 07/201,004, filed on June 1, 1988, abandoned.
US Referenced Citations (8)
Foreign Referenced Citations (3)
Number |
Date |
Country |
2194786 |
Mar 1988 |
EPX |
0144286 |
Sep 1982 |
JPX |
8700522 |
Jan 1987 |
WOX |
Continuation in Parts (1)
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Number |
Date |
Country |
Parent |
201004 |
Jun 1988 |
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