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Claims for Patent: 5,223,510

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Claims for Patent: 5,223,510

Title: Alkylaminoalkyl derivatives of benzofuran, benzothiophene, indole and indolizine, process for their preparation and compositions containing them
Abstract:The subject of the invention is benzofuran, benzothiophene, indole or indolizine compounds of general formula: ##STR1## in which: Het represents one of the groups: ##STR2## in which T,T' and T"represent particularly a group: ##STR3## R and R.sub.a, identical or different, represent X represent --O-- or --S-- Y represents a radical ##STR4## These compounds are useful as medecines particularly for the treatment of pathological syndroms of the cardio-vascular system.
Inventor(s): Gubin; Jean (Brussels, BE), Chatelain; Pierre (Brussels, BE), Lucchetti; Jean (Chastre, BE), Rosseels; Gilbert (Wemmel, BE), Inion; Henri (Wemmel, BE)
Assignee: Sanofi (Paris, FR)
Application Number:07/736,580
Patent Claims: 1. A benzofuran, benzothiophene, indole or indolizine compound of formula: ##STR118## in which: Het represents one of: ##STR119## in which: T represents: ##STR120## in which: R and R.sub.a, identical or different, represent:

hydrogen,

C.sub.1 -C.sub.4 alkyl

SO.sub.2 R' in which R' represents a linear or branched C.sub.1 -C.sub.6 alkyl, trifluoromethyl, phenyl, phenyl substituted by a C.sub.1 -C.sub.4 alkyl, benzyl, benzyl substituted by C.sub.1 -C.sub.4 alkyl, benzoyl or benzoyl substituted by C.sub.1 -C.sub.4 alkyl, and R.sub.a and R' forming with the nitrogen atom to which they are attached a ring bearing from 3 to 6 carbon atoms,

T' represents:

hydrogen

nitro ##STR121## as previously defined, T" represents:

benzyloxycarbonylamino ##STR122## in which T".sub.1 represents hydrogen or C.sub.1 -C.sub.4 alkyl ##STR123## in which T".sub.2 and T".sub.3, identical or different, represent hydrogen or C.sub.1 -C.sub.4 alkyl or T".sub.2 and T".sub.3 form with the nitrogen atom to which they are attached a ring having from 4 to 6 carbon atoms ##STR124## as defined previously X represents --O-- or --S--

Y represents ##STR125## in which R.sub.5 represents hydrogen, C.sub.1 -C.sub.4 alkyl or an acyl of formula ##STR126## in which R'.sub.4 represents C.sub.1 -C.sub.4 alkyl R.sub.1 represents C.sub.1 -C.sub.6 alkyl, phenyl, phenyl substituted by C.sub.1 -C.sub.4 alkyl or halogenophenyl

R.sub.2 represents:

hydrogen

a linear or branched C.sub.1 -C.sub.6 alkyl

R.sub.3 represents:

a linear or branched C.sub.1 -C.sub.6 alkyl

Alk--R.sub.6 in which Alk represents a simple bond or a linear or branched C.sub.1 -C.sub.5 alkylene and R.sub.6 represents pyridyl, phenyl, phenoxy, 3,4-methylenedioxy phenyl or phenyl or phenoxy substituted by one or more substituents, identical or different, selected from halogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy, R.sub.2 and R.sub.3, when they are taken together, represent C.sub.3 -C.sub.6 alkylene or alkenylene or C.sub.3 -C.sub.6 alkylene or alkenylene substituted by phenyl, 3-oxo-1,5-pentamethylene, 3-aza 1,5-pentamethylene, 3-methylaza 1,5-pentamethylene, 3-phenylaza 1,5-pentamethylene or --CH--CH--N.dbd.CH--,

R.sub.4 represents:

hydrogen

C.sub.1 -C.sub.4 alkyl

--SO.sub.2 R'.sub.1 in which R'.sub.1 represents C.sub.1 -C.sub.4 alkyl, phenyl, phenyl substituted by C.sub.1 -C.sub.4 alkyl, benzyl, or benzyl substituted by C.sub.1 -C.sub.4 alkyl ##STR127## in which R'.sub.4 and R".sub.4, identical or different, represent C.sub.1 -C.sub.4 alkyl and m represents an integer from 1 to 3

A represents --O--, --S-- or ##STR128## W, W' and Z are such that: when identical, W and W' represent ##STR129## or N, Z represents --O-- or --S-- when W represents ##STR130## and W' represents ##STR131## Z represents --CH.dbd.C'--R'.sub.8 R.sub.8 and R'.sub.8 being identical or different and representing hydrogen, a halogen atom, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy, n represents an integer from 1 to 5 provided that when R.sub.4 represents --SO.sub.2 R'.sub.1, T' represents hydrogen, nitro or cyclised ##STR132## or a pharmaceutically acceptable salt thereof.

2. A compound according to claim 1 in which R represents --SO.sub.2 R' and R.sub.a represents hydrogen.

3. A compound according to claim 1 in which Y represents ##STR133##

4. A compound according to claim 1 in which the moiety ##STR134## represents benzoyl.

5. A compound according to claim 1 in which the moiety ##STR135## represents 4-benzoyl oxy.

6. A compound according to claim 1 in which R.sub.1, R.sub.2 and R.sub.3 represent n-butyl and n represents 3.

7. A compound according to claim 1 in which X represents --O--.

8. A compound according to claim 1 in which the chain ##STR136## is at position 4.

9. A compound according to claim 1 in which the pharmaceutically acceptable salt is the oxalate, fumarate, hydrochloride or p-toluenesulfonate.

10. A compound according to claim 1 selected from:

2-n-butyl 3-[4-(3-di-n-butylamino-propoxy)benzoyl]5-methylsulfonamido benzofuran,

2-n-butyl 3-{4-[3-(N-methyl N-3,4-dimethoxy-.beta.-phenethyl)aminopropoxy]benzoyl} 5-methylsulfonamido benzofuran,

2-isopropyl 3-[4-(3-di-n-butylamino-propoxy)benzoyl]5-methylsulfonamido benzofuran,

5-amino 3-[4-(3-di-n-butylamino-propoxy)benzoyl]2-n-butyl 1-methyl indole,

or pharmaceutically acceptable salts thereof.

11. A pharmaceutical composition containing as active ingredient at least one derivative of benzofuran, benzothiophene, indole or indolizine according to claim 1, in combination with a pharmaceutical vehicle or excipient.

12. A pharmaceutical composition containing as active ingredient at least one derivative according to claim 10, in combination with a pharmaceutical vehicle or excipient.

13. A method for the treatment of angina pectoris comprising administering to an animal in need thereof a pharmaceutical composition according to claim 11 containing from 50 to 500 mg of active ingredient.

14. A method of using at least one derivative of benzofuran, benzothiophene, indole or indolizine according to claim 1 comprising combining the derivative with a pharmaceutical vehicle or a suitable excipient for the production of a medicine designed for the treatment of angina pectoris.

15. A method for the treatment of hypertension comprising administering to an animal in need thereof a pharmaceutical composition according to claim 11 containing from 50 to 500 mg of active ingredient.

16. A method for the treatment of arrhythmias comprising administering to an animal in need thereof a pharmaceutical composition according to claim 11 containing from 50 to 500 mg of active ingredient.

17. A method for the treatment of cerebral circulatory insufficiency comprising administering to an animal in need thereof a pharmaceutical composition according to claim 11 containing from 50 to 500 mg of active ingredient.

18. A method of using at least one derivative of benzofuran, benzothiophene, indole or indolizine according to claim 1 comprising combining the derivative with a pharmaceutical vehicle or a suitable excipient for the production of a medicine designed for the treatment of hypertension.

19. A method of using at least one derivative of benzofuran, benzothiophene, indole or indolizine according to claim 1 comprising combining the derivative with a pharmaceutical vehicle or a suitable excipient for the production of a medicine designed for the treatment of arrhythmias.

20. A method of using at least one derivative of benzofuran, benzothiophene, indole or indolizine according to claim 1 comprising combining the derivative with a pharmaceutical vehicle or a suitable excipient for the production of a medicine designed for the treatment of cerebral circulatory insufficiency.

21. A veterinary composition containing as active ingredient at least one derivative of benzofuran, benzothiophene, indole or indolizine according to claim 1, in combination with a pharmaceutical vehicle or excipient.

22. A method for the treatment of angina pectoris comprising administering to an animal in need thereof a veterinary composition according to claim 11 containing from 50 to 500 mg of active ingredient.

23. A method for the treatment of hypertension comprising administering to an animal in need thereof a veterinary composition according to claim 11 containing from 50 to 500 mg of active ingredient.

24. A method for the treatment of arrhythmias comprising administering to an animal in need thereof a veterinary composition according to claim 11 containing from 50 to 500 mg of active ingredient.

25. A method for the treatment of cerebral circulatory insufficiency comprising administering to an animal in need thereof a veterinary composition according to claim 11 containing from 50 to 500 mg of active ingredient.

26. A veterinary composition containing as active ingredient at least one derivative according to claim 10, in combination with a pharmaceutical vehicle or excipient.
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