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Details for Patent: 5,981,527

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Details for Patent: 5,981,527

Title: Cyclic GMP-specific phosphodiesterase inhibitors
Abstract:A compound having the formula (I) ##STR1## and solvates thereof, wherein: R.sup.0 represents hydrogen, halogen or C.sub.1-6 alkyl; R.sup.1 represents hydrogen or C.sub.1-6 alkyl; R.sup.2 represents the bicyclic ring ##STR2## which may be optionally substituted by one or more groups selected from halogen and C.sub.1-3 alkyl; and R.sup.3 represents hydrogen or C.sub.1-3 alkyl is disclosed. The compounds are potent and selective inhibitors of cGMP-specific PDE, and are useful in a variety of therapeutic areas where such inhibition is beneficial.
Inventor(s): Daugan; Alain Claude-Marie (Les Ulis, FR), Gellibert; Francoise (Les Ulis, FR)
Assignee: ICOS Corporation (Bothell, WA)
Filing Date:May 15, 1998
Application Number:09/000,192
Claims:1. A compound of formula (I) ##STR11## and solvates thereof, in which: R.sup.0 represents hydrogen, halogen or C.sub.1-6 alkyl;

R.sup.1 represents hydrogen or C.sub.1-6 alkyl;

R.sup.2 represents the bicyclic ring; ##STR12## and R.sup.3 represents hydrogen or C.sub.1-3 alkyl.

2. A compound according to claim 1 wherein R.sup.0 represents hydrogen.

3. A compound according to claim 1 wherein R.sup.1 is selected from hydrogen, methyl, and iso-propyl.

4. A compound according to claim 1 wherein R.sup.3 represents hydrogen or methyl.

5. (6R,1 2aR)-2,3,6,7,12,12a-Hexahydro-6-(5-benzofuranyl)-2-methyl-pyrazino[2',1':6, 1]pyrido[3,4-b]indole-1,4-dione;

(6R,12aR)-2,3,6,7,12,12a-Hexahydro-6-(5-benzofuranyl)-pyrazino[2',1':6,1]py rido[3,4-b]indole-1,4-dione;

(3S,6R,12aR)-2,3,6,7,12,12a-Hexahydro-6-(5-benzofuranyl)-3-methyl-pyrazino[ 2',1':6,1]pyrido[3,4-b]indole-1,4-dione;

(3S,6R,12aR)-2,3,6,7,12,12a-Hexahydro-6-(5-benzofuranyl)-2,3-dimethyl-pyraz ino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione;

(6R,12aR)-2,3,6,7,12,12a-Hexahydro-6-(5-benzofuranyl)-2-isopropyl-pyrazino[ 2',1':6,1]pyrido[3,4-b]indole-1,4-dione;

and physiologically acceptable solvates thereof.

6. (6R,12aR)-2,3,6,7,12,1 2a-Hexahydro-6-(5-benzofuranyl)-2-methyl-pyrazino[2',1':6,1]pyrido[3,4-b]i ndole-1,4-dione.

7. A process for preparing a compound according to claim 1 ##STR13## comprising hydrogenating a compound of formula (III) ##STR14## in which Alk is defined as above and Cbz represents a carbobenzyloxy group, in the presence of a catalyst in a suitable solvent such as an alcohol, at elevated temperature; optionally followed by

i) an interconversion step; and/or

iii) solvate formation.

8. A pharmaceutical composition comprising a compound according to claim 1, together with a pharmaceutically acceptable diluent or carrier therefor.

9. A process of preparing a pharmaceutical composition comprising a compound according to claim 1, which process comprises mixing said compound together with a pharmaceutically acceptable diluent or carrier therefor.

10. A method of treating conditions where inhibition of cGMP specific PDE is of therapeutic benefit, in a human or non-human animal body, which comprises administering to said body a therapeutically effective amount of a compound according to claim 1.

11. The method of claim 10 wherein the condition is erectile dysfunction.

12. The method of claim 11 wherein the animal body is human.

13. The method of claim 11 wherein the compound is administered orally.
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