2-Cyano-4-(2-hydroxy-3-substituted-aminopropoxy) indoles

Claim 2

A compound of formula I ##STR38## wherein either (A) R 1 is: (a) a group --B--CO--R h , wherein B is a group (i), (ii) or (iii), groups (i), (ii) and (iii) having the following significances: ##STR39## wherein V and W are hydrogen or together form an additional bond, R i is hydrogen, alkyl of 1 to 4 carbon atoms, phenyl or phenyl monosubstituted or independently disubstituted by alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms or halogen of atomic number of from 9 to 35; ##STR40## wherein R j is hydrogen or alkyl of 1 to 4 carbon atoms; ##STR41## wherein n is 2, 3 or 4, R k has the significance indicated above for R j and R e has the significance indicated above for R i , and R h is phenylalkyl of 7 to 11 carbon atoms or diphenylalkyl of 13 to 17 carbon atoms, any of the phenyl rings of these two radicals optionally being monoor independently disubstituted by alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms or halogen of atomic number of from 9 to 35;

Claim 3

(b) a group ##STR42## wherein R m is --COR n or --R p , wherein R n has the significance indicated above for R h and R p has the significance indicated above for R h or is phenyl independently disubstituted by alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms or halogen of atomic number of from 9 to 35, R 2 is hydroxy and R 3 is hydrogen or (B) R 1 is a group (i'), (ii') or (iii'), groups (i'), (ii') and (iii') having the following significances: ##STR43## wherein Y and Y' are a bond or methylene, and R 1 a to R i j are hydrogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms or halogen of atomic number of from 9 to 35, R 2 is hydrogen, methyl, hydroxymethyl, carboxyl, alkoxycarbonyl of 2 to 5 carbon atoms, carbamoyl or cyano and R 3 is hydrogen or methyl, and physiologically acceptable hydrolyzable derivatives thereof having the hydroxy group in the 2 position of the 3-aminopropoxy side chain in esterified form, or a pharmaceutically acceptable salt form thereof.

Claim 4

(b) a group ##STR42## wherein R m is --COR n or --R p , wherein R n has the significance indicated above for R h and R p has the significance indicated above for R h or is phenyl independently disubstituted by alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms or halogen of atomic number of from 9 to 35, R 2 is hydroxy and R 3 is hydrogen or (B) R 1 is a group (i'), (ii') or (iii'), groups (i'), (ii') and (iii') having the following significances: ##STR43## wherein Y and Y' are a bond or methylene, and R 1 a to R i j are hydrogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms or halogen of atomic number of from 9 to 35, R 2 is hydrogen, methyl, hydroxymethyl, carboxyl, alkoxycarbonyl of 2 to 5 carbon atoms, carbamoyl or cyano and R 3 is hydrogen or methyl, and physiologically acceptable hydrolyzable derivatives thereof having the hydroxy group in the 2 position of the 3-aminopropoxy side chain in esterified form, or a pharmaceutically acceptable salt form thereof.

Claim 5

The compound of claim 1 of formula I, wherein R 1 is 4-(diphenylmethyl)-1-piperazinyl, R 2 is hydroxy and R 3 is hydrogen, or a pharmaceutically acceptable salt form thereof.

Claim 6

A pharmaceutical composition comprising a compound of claim 1 in association with a pharmaceutical carrier or diluent.

Claim 7

A method of treating heart insufficiency, which comprises administering to an animal in need of such treatment a therapeutically effective amount of a compound of claim 1.

Claim 8

A compound of formula I of claim 1 wherein either (A) R 1 is: (a) a group --B--CO--R h , wherein B is a group (i), (ii) or (iii), groups (i), (ii) and (iii) having the following significances: ##STR44## wherein V and W are hydrogen or together form an additional bond, R i is hydrogen, alkyl of 1 to 4 carbon atoms, phenyl or phenyl monosubstituted or independently disubstituted by alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms or halogen of atomic number of from 9 to 35; ##STR45## wherein R j is hydrogen or alkyl of 1 to 4 carbon atoms; ##STR46## wherein n is 2, 3 or 4, R k has the significance indicated above for R j and R e has the significance indicated above for R i , and R h is phenylalkyl of 7 to 11 carbon atoms or diphenylalkyl of 13 to 17 carbon atoms, any of the phenyl rings of these two radicals optionally being mono- or independently disubstituted by alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms or halogen of atomic number of from 9 to 35; (b) a group ##STR47## wherein R m is --COR n or --R p , wherein R n has the significance indicated above for R h and R p has the significance indicated above for R h or is phenyl independently disubstituted by alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon carbon atoms or halogen of atomic number of from 9 to 35, R 2 is hydroxy and R 3 is hydrogen or (B) R 1 is a group (i'), (ii') or (iii'), groups (i'), (ii'), and (iii') having the following significances: ##STR48## wherein Y and Y' are a bond or methylene, and R 1 a to R i j are hydrogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms or halogen of atomic number of from 9 to 35, R 2 is hydrogen, methyl, hydroxymethyl, carboxyl, alkoxycarbonyl of 2 to 5 carbon atoms, carbamoyl or cyano and R 3 is hydrogen or methyl, and physiologically acceptable hydrolyzable derivatives thereof having the hydroxy group in the 2 position of the 3-aminopropoxy side chain in esterified form, or a pharmaceutically acceptable salt form thereof.

Claim 9

A compound of formula I of claim 1 wherein either (A) R 1 is: (a) a group --B--CO--R h , wherein B in a group (i), (ii) or (iii), groups (i), (ii) and (iii) having the following significances: ##STR49## wherein V and W are hydrogen or together form an additional bond, R i is hydrogen, alkyl of 1 to 4 carbon atoms, phenyl or phenyl monosubstituted or independently disubstituted by alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms or halogen of atomic number of from 9 to 35; ##STR50## wherein R j is hydrogen or alkyl of 1 to 4 carbon atoms; ##STR51## wherein n is 2, 3 or 4, R k has the significance indicated above for R j and R e has the significance indicated above for R i , and R h is phenylalkyl of 7 to 11 carbon atoms or diphenylalkyl of 13 to 17 carbon atoms, any of the phenyl rings of these two radicals optionally being mono- or independently disubstituted by alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms or halogen of atomic number of from 9 to 35; (b) a group ##STR52## wherein R m is --COR n or --R p , wherein R n has the significance indicated above for R h and R p has the significance indicated above for R h or is phenyl independently disubstituted by alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon carbon atoms or halogen of atomic number of from 9 to 35, R 2 is hydroxy and R 3 is hydrogen or (B) R 1 is a group (i'), (ii') or (iii'), groups (i'), (ii'), and (iii') having the following significances: ##STR53## wherein Y and Y' are a bond or methylene, and R 1 a to R i j are hydrogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms or halogen of atomic number of from 9 to 35, R 2 is hydrogen, methyl, hydroxymethyl, carboxyl, alkoxycarbonyl of 2 to 5 carbon atoms, carbamoyl or cyano and R 3 is hydrogen or methyl, and physiologically acceptable hydrolyzable derivatives thereof having the hydroxy group in the 2 position of the 3-aminopropoxy side chain in esterified form, or a pharmaceutically acceptable salt form thereof, and or a pharmaceutically acceptable salt form thereof.

Claim 10

A compound of formula is of claim 1 ##STR54## wherein either (A') R 1 s is a group ##STR55## wherein R 1 s is diphenylalkyl of 13 to 17 carbon atoms, any of the phenyl rings of this radical optionally being mono- or independently disubstituted by alkoxy of 1 to 4 carbon atoms or halogen of atomic number of from 9 to 35 and R 2 s is hydroxy, or (B') R 1 s is a group ##STR56## wherein Y and Y' are as defined above, and R 2 s is cyano, or a pharmaceutically acceptable salt form thereof.

Claim 11

A compound of claim 1 where Y and Y' are methylene.

Claim 12

A compound of claim 7 where Y and Y' are methylene.

Claim 13

A compound of claim 8 where Y and Y' are methylene.

Claim 14

A compound of claim 9 where Y and Y' are methylene.