Claims
- 1. A compound of the formula ##STR9## wherein: R is hydrogen or lower alkyl;
- R.sub.1, R'.sub.1, R.sub.2, R'.sub.2, R.sub.3, R'.sub.3, R.sub.4, R'.sub.4, R.sub.5, R'.sub.5 are each independently hydrogen, hydroxy, formylamino, aminocarbonyl, (aminocarbonyl)amino, aminosulfonyl, or halo; and
- n and m are each independently an integer from 1 to 10, or its S stereoisomer, or a racemic mixture of isomers thereof,
- or a pharmaceutically acceptable salt of the compound, of its S stereoisomer, or of a racemic or non-racemic mixture of isomers thereof.
- 2. The compound of claim 1 wherein
- R.sub.1, R'.sub.1, R.sub.4, R'.sub.4, R.sub.5, and R'.sub.5 are hydrogen; and
- R is lower alkyl of 1 to 4 carbon atoms,
- or its S stereoisomer, or a racemic or non-racemic mixture of isomers thereof,
- or a pharmaceutically acceptable salt of the compound, its S stereoisomer, or a racemic or non-racemic mixture of isomers thereof.
- 3. The compound of claim 2 wherein
- each of R.sub.2, R'.sub.2, R.sub.3, R'.sub.3 is independently hydrogen or hydroxy,
- or its S stereoisomer, or a racemic or non-racemic mixture of isomers thereof,
- or a pharmaceutically acceptable salt of the compound, its S stereoisomer, or a racemic or non-racemic mixture of isomers thereof.
- 4. The compound of claim 3 wherein
- n is an integer from 3 to 8; and
- m is an integer from 1 to 3,
- or its S stereoisomer, or a racemic or non-racemic mixture of isomers thereof,
- or a pharmaceutically acceptable salt of the compound, its S stereoisomer, or a racemic or non-racemic mixture of isomers thereof.
- 5. The compound of claim 4 wherein
- R is propyl;
- n is 4 or 5; and
- m is 1,
- or its S stereoisomer, or a racemic or non-racemic mixture of isomers thereof,
- or a pharmaceutically acceptable salt of the compound, its S stereoisomer, or a racemic or non-racemic mixture of isomers thereof.
- 6. The compound of claim 5 wherein
- R.sub.2, R'.sub.2, R.sub.3, and R'.sub.3 are hydroxy; and
- n is 4, namely,
- R)-2-(3,4-dihydroxybenzyl)-1-[5-(N-(2-(3,4-dihydroxyphenyl)-ethyl)-N-propylamino)pentyl]pyrrolidine
- or its S stereoisomer, or a racemic or non-racemic mixture of isomers thereof,
- or a pharmaceutically acceptable salt of the compound, its S stereoisomer, or a racemic or non-racemic mixture of isomers thereof.
- 7. The compound of claim 6 which is
- (R)-2-(3,4-dihydroxybenzyl)-1-[5-(N-(2-(3,4-dihydroxyphenyl)-ethyl)-N-propylamino)pentyl]pyrroline,
- or a pharmaceutically acceptable salt thereof.
- 8. The compound of claim 7 which is a pharmaceutically acceptable salt of (R)-2-(3,4-dihydroxybenzyl)-1-[5-(N-(2-(3,4-dihydroxyphenyl)ethyl)-N-propylamino) pentyl]-pyrrolidine.
- 9. The compound of claim 5 wherein
- R.sub.2, R'.sub.2, R.sub.3, and R'.sub.3 are hydroxy; and
- n is 5, namely,
- (R)-2-(3,4-dihydroxybenzyl)-1]6-(N-(2-(3,4-dihydroxyphenyl)ethyl)-N-propylamino)hexyl]-pyrrolidine,
- or its S stereoisomer, or a racemic or non-racemic mixture of isomers thereof,
- or a pharmaceutically acceptable salt of the compound, its S stereoisomer, or a racemic or non-racemic mixture of isomers thereof.
- 10. The compound of claim 9 which is (R)-2-(3,4-dihydroxybenzyl)-1-[6-(N-(2-(3,4-dihydroxyphenyl)ethyl-N-propylamino)hexyl]pyrrolidine, or a pharmaceutically acceptable salt thereof.
- 11. The compound of claim 10 which is a pharmaceutically acceptable salt of (R)-2-(3,4-dihydroxybenzyl)-1-[6-(N-(2-(3,4-dihydroxyphenyl)ethyl)-N-propylamino)hexyl]-pyrrolidine.
- 12. The compound of claim 5 wherein
- R.sub.2, R.sub.3, and R'.sub.3 are hydroxy;
- R'.sub.2 is hydrogen; and
- n is 4, namely,
- (R)-2-(3,4-dihydroxybenzyl)-1-[5-(N-(2-(4-hydroxyphenyl)ethyl)-N-propylamino)pentyl]-pyrrolidine,
- or its S stereoisomer, or a racemic or non-racemic mixture of isomers thereof,
- or a pharmaceutically acceptable salt of the compound, its S stereoisomer, or a racemic or non-racemic mixture of isomers thereof.
- 13. The compound of claim 12 which is (R)-2-(3,4-dihydroxybenzyl)-1-[5-(N-(2-(4-hydroxyphenyl)ethyl)-N-propylamino)pentyl]pyrrolidine, or a pharmaceutically acceptable salt thereof.
- 14. The compound of claim 12 which is a pharmaceutically acceptable salt of (R)-2-(3,4-dihydroxybenzyl)-1-[5-(N-(2-(4-hydroxyphenyl)ethyl)-N-propylamino)pentyl]-pyrrolidine.
- 15. The compound of claim 5 wherein
- R.sub.2, R.sub.3, and R'.sub.3 are hydroxy;
- R'.sub.2 is hydrogen; and
- n is 5, namely,
- (R)-2-(3,4-dihydroxybenzyl)-1[6-(N-(2-(4-hydroxyphenyl)ethyl)-N-propylamino)hexyl]-pyrrolidine,
- or its S stereoisomer, or a racemic or non-racemic mixture of isomers thereof,
- or a pharmaceutically acceptable salt of the compound, its S stereoisomer, or a racemic or non-racemic mixture of isomers thereof.
- 16. The compound of claim 15 which is (R)-2-(3,4-dihydroxybenzyl)-1-[6(N-(2(4-hydroxyphenyl)ethyl)-N-propylamino)hexyl]pyrrolidine, or a pharmaceutically acceptable salt thereof.
- 17. The compound of claim 16 which is a pharmaceutically acceptable salt of (R)-2-(3,4-dihydroxybenzyl)-1-[6(N-(2(4-hydroxyphenyl)ethyl)-N-propylamino)hexyl]pyrrolidine.
- 18. A composition, comprising:
- a pharmaceutically acceptable carrier; and
- a compound of the formula ##STR10## wherein: R is hydrogen or lower alkyl;
- R.sub.1, R'.sub.1, R.sub.2, R'.sub.2, R.sub.3, R'.sub.3, R.sub.4, R'.sub.4, R.sub.5, and R'.sub.5 are each independently hydrogen, hydroxy, formylamino, aminocarbonyl, (aminocarbonyl)amino, aminosulfonyl, or halo; and
- n and m are each independently an integer from 1 to 10,
- or its S stereoisomer, or a racemic or non-racemic mixture of isomers thereof, or a pharmaceutically acceptable salt of the compound, its S stereoisomer, or a racemic or non-racemic mixture of isomers thereof.
- 19. The composition of claim 18 wherein
- R.sub.1, R'.sub.1, R.sub.4, R'.sub.4, R.sub.5 and R'.sub.5 are hydrogen;
- each of R.sub.2, R'.sub.2, R.sub.3 and R'.sub.3 is independently hydrogen or hydroxy;
- R is lower alkyl of 1 to 4 carbon atoms;
- n is an integer form 3 to 8; and
- m is an integer from 1 to 3.
- 20. The composition of claim 19 wherein
- R is propyl;
- n is 4 or 5; and
- m is 1.
- 21. The composition of claim 20 wherein the compound is (R)-2-(3,4-dihydroxybenzyl)-1-[5-(N-(2(3,4-dihydroxyphenyl)ethyl)-N-propylamino)pentyl[pyrrolidine, or a pharmaceutically acceptable salt thereof.
- 22. The composition of claim 20 wherein the compound is (R)-2-(3,4-dihydroxybenzyl)-1-[6-(N-(2-(4-hydroxyphenyl)ethyl)-N-propylamino)hexyl]pyrrolidine, or a pharmaceutically acceptable salt thereof.
- 23. A method of treating cardiovascular disorders comprising administering to a mammal in need thereof a pharmaceutically effective amount of a compound of the formula ##STR11## wherein: R is hydrogen or lower alkyl;
- R.sub.1, R'.sub.1, R.sub.2, R'.sub.2, R.sub.3, R'.sub.3, R.sub.4, R'.sub.4, R.sub.5, and R'.sub.5 are each independently hydrogen, hydroxy, formylamino, aminocarbonyl, (aminocarbonyl)amino, aminosulfonyl, or halo; and
- n and m are each independently an integer from 1 to 10,
- or its S stereoisomer, or a racemic or non-racemic mixture of isomers thereof,
- or a pharmaceutically acceptable salt of the compound, its S stereoisomer, or a racemic or non-racemic mixture of isomers thereof.
- 24. The method of claim 23 wherein
- R.sub.1, R'.sub.1, R.sub.4, R'.sub.4, R.sub.5 and R'.sub.5 are hydrogen;
- each of R.sub.2, R'.sub.2, R.sub.3 and R'.sub.3 is independently hydrogen or hydroxy;
- R is lower alkyl of 1 to 4 carbon atoms;
- n is an integer form 3 to 8; and
- m is an integer from 1 to 3.
- 25. The method of claim 24 wherein
- R is propyl;
- n is 4 or 5; and
- m is 1.
- 26. The method of claim 25 wherein the compound is
- (R)-2-(3,4-dihydroxybenzyl)-1-[5-(N-(2-(3,4-dihydroxyphenyl)ethyl)-N-propylamino)pentyl]pyrrolidine,
- or a pharmaceutically acceptable salt thereof.
- 27. The method of claim 25 wherein the compound is (R)-2-(3,4-dihydroxybenzyl)-1-[6(N-(2-(4-hydroxyphenyl)ethyl)-N-propylamino)hexyl]pyrrolidine, or a pharmaceutically acceptable salt thereof.
- 28. A method of treating hypertension in a mammal, comprising administering to the mammal a pharmaceutically effective amount of a compound of the formula ##STR12## wherein: R is hydrogen or lower alkyl;
- R.sub.1, R'.sub.1, R.sub.2, R'.sub.2, R.sub.3, R'.sub.3, R.sub.4, R'.sub.4, R.sub.5, and R'.sub.5 are each independently hydrogen, hydroxy, formylamino, aminocarbonyl, (aminocarbonyl)amino, aminosulfonyl, or halo; and
- n and m are each independently an integer from 1 to 10,
- or its S stereoisomer, or a racemic or non-racemic mixture of isomers thereof, or a pharmaceutically acceptable salt of the compound, its S stereoisomer, or a racemic or non-racemic mixture of isomers thereof.
- 29. The method of claim 28 wherein
- R.sub.1, R'.sub.1, R.sub.4, R'.sub.4, R.sub.5 and R'.sub.5 are hydrogen;
- each of R.sub.2, R'.sub.2, R.sub.3 and R'.sub.3 is independently hydrogen or hydroxy;
- R is lower alkyl of 1 to 4 carbon atoms;
- n is an integer form 3 to 8; and
- m is an integer from 1 to 3.
- 30. The method of claim 29 wherein
- R is propyl;
- n is 4 or 5; and
- m is 1.
- 31. The method of claim 30 wherein the compound is (R)-2-(3,4-dihydroxybenzyl)-1-[5-(N-(2-(3,4-dihydroxyphenyl)ethyl)-N-propylamino)pentyl]pyrrolidine, or a pharmaceutically acceptable salt thereof.
- 32. The method of claim 30 wherein the compound is (R)-2-(3,4-dihydroxybenzyl)-1-[6(N-(2-(4-hydroxyphenyl)ethyl)-N-propylamino)hexyl]pyrrolidine, or a pharmaceutically acceptable salt thereof.
Parent Case Info
This is a continuation of our co-pending application Ser. No. 07/428,577, filed Oct. 30, 1989, now abandoned.
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4342692 |
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DEX |
Continuations (1)
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Number |
Date |
Country |
Parent |
428577 |
Oct 1989 |
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