Claims
- 1. A compound of formula (I) in which:A represents a hydrogen atom, an azido, a halogen, a hydroxyl, a thiol, an amino, a phenyl, a C1-6 akyl, C1-6 alkylamino, di(C1-6 alkyl)amino, hydroxylamine, C1-6 alkylhydroxylamine, N,O—C1-6 dialkylhydroxylamine, C1-6 alkoxy or C1-6 alkylsulphanyl group, B and D represent, independently of each other, a hydrogen atom, a phenyl, a C1-6 alkyl, C2-6 alkenyl, C1-6 fluoroalkyl or C1-2 perfluoroalkyl group, or together form an oxo, R1 represents a hydrogen atom, a halogen, a carbonyl, a hydroxycarbonyl, a cyano, a carboxamide, a C1-6 alkyl, C2-6 alkenyl, C3-6 cycloalkyl, C1-6 alkoxycarbonyl, C1-6 hydroxyalkyl, C1-6 alkoxy, (C1-6)alkoxy(C1-3)alkyl, C1-6 fluoroalkyl, C1-2 perfluoroalkyl or CF3(OH)CH group, or R1 and R2 together form a C3-5 alkylene or C3-5 alkenylene chain or form, with the carbon atoms to which they are attached, a phenyl, R2, R3 and R4 represent, independently of each other, a hydrogen atom, a halogen or a C1-6 alkyl group, or R2 and R3 together form a C3-5 alkylene or C3-5 alkenylene chain or R1 and R2, together, are as defined above, R5 and R6 represent, independently of each other, a hydrogen atom, a C1-6 alkyl, C2-6 alkenyl, C3-6 cycloalkyl, C3-6 cycloalkenyl, C1-6 fluoroalkyl or C1-2 perfluoroalkyl group or R5 and R6 together form a C2-6 alkylene or C3-6 alkenylene chain, to give, with the nitrogen to which they are attached, a heterocycle, this heterocycle optionally being substituted with a C1-4 alkyl group, and salts thereof, with the exception of 8-(1-aminoethyl)quinoline.
- 2. A compound according to claim 1 wherein:A represents a hydroxyl, a phenyl or a C1-3 alkyl, N,O—C1-3 dialkylhydroxylamine or C1-3 alkoxy group; B and D represent, independently of each other, a hydrogen atom, a phenyl or a C1-3 alkyl group or together form an oxo; R1 represents a C1-3 alkyl or C1-2 perfluoroalkyl group or R1 and R2 together form a C3-5 alkylene chain, or R1 and R2 form, with the carbons to which they are attached, a phenyl; R2, R3 and R4 represent, independently of each other, a hydrogen atom, a halogen or a C1-3 alkyl, group, or R2 and R3 together form a C3-C5 alkylene chain, or R1 and R2, together, are as defined above, R5 and R6 represent, independently of each other, a C1-6 alkyl group, or R5 and R6 together form a piperidyl, this piperidyl optionally being substituted with a C1-2 alkyl group.
- 3. 2,3-Dimethyl-8-(1-diethylamino-2-hydroxyethyl)quinoline, or (+)-2-ethyl-3-methyl-8-(1(R)-diethylamino-2-hydroxyethyl)quinoline according to claim 2.
- 4. A process for preparing a compound of formula (I) according to claim 1, in which A is a hydroxyl group wherein a compound of formula II in which R1, R3, R4, B and D are as defined in claim 1 and Pg is a protecting group, is reacted with an amine of formula HNR5R6 in which R5 and R6 are as defined in claim 1, followed by a deprotection.
- 5. A process for preparing a compound of formula (I) according to claim 1, in which A is a C1-6 alkoxy group and B and D together are an oxo group, by reacting a compound of formula XVI in which R1, R2, R3 and R4 are as defined in claim 1, A is a C1-6 alkoxy group and B and D represent an oxo group, with an amine of formula HNR5R6 in which R5 and R6 are as defined in claim 1.
- 6. A process for preparing a compound of formula (I) according to claim 1, in which A is not a hydroxyl group wherein a compound of formula XVII in which R1, R2, R3, R4, R5, R6, B and D are as defined in claim 1 and W is a nucleofugal group, is reacted with a nucleophilic group A as defined in claim 1.
- 7. A method of contracting smooth muscles which comprises administering to a patient in need of such treatment an effective amount of a compound of formula (I) in which:A represents a hydrogen atom, an azido, a halogen, a hydroxyl, a thiol, an amino, a phenyl, a C1-6 alkyl, C1-6 alkylamino, di(C1-6 alkyl)amino, hydroxylamine, C1-6 alkylhydroxylamine, N,O—C1-6 dialkylhydroxylamine, C1-6 alkoxy or C1-6 alkylsulphanyl group, B and D represent, independently of each other, a hydrogen atom, a phenyl, a C1-6 alkyl, C2-6 alkenyl, C1-6 fluoroalkyl or C1-2 perfluoroalkyl group, or together form an oxo, R1 represents a hydrogen atom, a halogen, a carbonyl, a hydroxycarbonyl, a cyano, a carboxamide, a C1-6 alkyl, C2-6 alkenyl, C3-6 cycloalkyl, C1-6 alkoxycarbonyl, C1-6 hydroxyalkyl, C1-6 alkoxy, (C1-6)alkoxy(C1-3)alkyl, C1-6 fluoroalkyl, C1-2 perfluoroalkyl or CF3(OH)CH group, or R1 and R2 together form a C3-5 alkylene or C3-5 alkenylene chain or form, with the carbon atoms to which they are attached, a phenyl, R2, R3 and R4 represent, independently of each other, a hydrogen atom, a halogen or a C1-6 alkyl group, or R2 and R3 together form a C3-5 alkylene or C3-5 alkenylene chain or R1 and R2, together, are as defined above, R5 and R6 represent, independently of each other, a hydrogen atom, a C1-6 alkyl, C2-6 alkenyl, C3-6 cycloalkyl, C3-6 cycloalkenyl, C1-6 fluoroalkyl or C1-2 perfluoroalkyl group or R5 and R6 together form a C2-6 alkylene or C3-6 alkenylene chain, to give, with the nitrogen to which they are attached, a heterocycle, this heterocycle optionally being substituted with a C1-4 alkyl group, and salts thereof.
- 8. A method according to claim 7 wherein:A represents a hydroxyl, a phenyl or a C1-3 alkyl, N,O—C1-3 dialkylhydroxylamine or C1-3 alkoxy group; B and D represent, independently of each other, a hydrogen atom, a phenyl or a C1-3 alkyl group or together form an oxo; R1 represents a C1-3 alkyl or C1-2 perfluoroalkyl group or R1 and R2 together form a C3-5 alkylene chain, or R1 and R2 form, with the carbons to which they are attached, a phenyl; R2, R3 and R4 represent, independently of each other, a hydrogen atom, a halogen or a C1-3 alkyl group, or R2 and R3 together form a C3-C5 alkylene chain, or R1 and R2, together, are as defined, above, R5 and R6 represent, independently of each other, a C1-6 alkyl group, or R5 and R6 together form a piperidyl, this piperidyl optionally being substituted with a C1-2 alkyl group.
- 9. A method according to claim 8 wherein the compound is 2,3-Dimethyl-8-(1-diethylamino-2-hydroxyethyl)quinoline, or (+)-2-ethyl-3-methyl-8-(1(R)-diethylamino-2-hydroxyethyl)quinoline.
- 10. A method according to claim 7 for the treatment of urinary stress incontinence, venous insufficiency, venous ulcers, migraine or gastrointestinal disorders.
- 11. A method according to claim 8 for the treatment of urinary stress incontinence, venous insufficiency, venous ulcers, migraine or gastrointestinal disorders.
- 12. A method according to claim 9 for the treatment of urinary stress incontinence, venous insufficiency, venous ulcers, migraine or gastrointestinal disorders.
- 13. A method according to claim 10 for the treatment of urinary stress incontinence.
- 14. A method according to claim 11 for the treatment of urinary stress incontinence.
- 15. A method according to claim 12 for the treatment of urinary stress incontinence.
- 16. A pharmaceutical composition comprising a compound of the formula (I) in which:A represents a hydrogen atom, an azido, a halogen, a hydroxyl, a thiol, an amino, a phenyl, a C1-6 alkyl, C1-6 alkylamino, di(C1-6 alkyl)amino, hydroxylamine, C1-6 alkylhydroxylamine, N,O—C1-6 dialkylhydroxylamine, C1-6 alkoxy or C1-6 alkylsulphanyl group, B and D represent, independently of each other, a hydrogen atom, a phenyl, a C1-6 alkyl, C2-6 alkenyl, C1-6 fluoroalkyl or C1-2 perfluoroalkyl group, or together form an oxo, R1 represents a hydrogen atom, a halogen, a carbonyl, a hydroxycarbonyl, a cyano, a carboxamide, a C1-6 alkyl, C2-6 alkenyl, C3-6 cycloalkyl, C1-6 alkoxycarbonyl, C1-6 hydroxyalkyl, C1-6 alkoxy, (C1-6)alkoxy(C1-3)alkyl, C1-6 fluoroalkyl, C1-2 perfluoroalkyl or CF3(OH)CH group, or R1 and R2 together form a C3-5 alkylene or C3-5 alkenylene chain or form, with the carbon atoms to which they are attached, a phenyl, R2, R3 and R4 represent, independently of each other, a hydrogen atom, a halogen or a C1-6 alkyl group, or R2 and R3 together form a C3-5 alkylene or C3-5 alkenylene chain or R1 and R2, together, are as defined above, R5 and R6 represent, independently of each other, a hydrogen atom, a C1-6 alkyl, C2-6 alkenyl, C3-6 cycloalkyl, C3-6 cycloalkenyl, C1-6 fluoroalkyl or C1-2 perfluoroalkyl group or R5 and R6 together form a C2-6 alkylene or C3-6 alkenylene chain, to give, with the nitrogen to which they are attached, a heterocycle, this heterocycle optionally being substituted with a C1-4 alkyl group, and salts thereof, together with one or more suitable excipients.
- 17. A pharmaceutical composition according to claim 16 wherein:A represents a hydroxyl, a phenyl or a C1-3 alkyl, N,O—C1-3 dialkylhydroxylamine or C1-3 alkoxy group; B and D represent, independently of each other, a hydrogen atom, a phenyl or a C1-3 alkyl group or together form an oxo; R1 represents a C1-3 alkyl or C1-2 perfluoroalkyl group or R1 and R2 together form a C3-5 alkylene chain, or R1 and R2 form, with the carbons to which they are attached, a phenyl; R2, R3 and R4 represent, independently of each other, a hydrogen atom, a halogen or a C1-3 alkyl group, or R2 and R3 together form a C3-C5 alkylene chain, or R1 and R2, together, are as defined above, R5 and R6 represent, independently of each other, a C1-6 alkyl group, or R5 and R6 together form a piperidyl, this piperidyl optionally being substituted with a C1-2 alkyl group.
- 18. A pharmaceutical composition according to claim 17 wherein the compound is 2,3-Dimethyl-8-(1-diethylamino-2-hydroxyethyl)quinoline, or (+)-2-ethyl-3-methyl-8-(1(R)-diethylamino-2-hydroxyethyl)quinoline.
Priority Claims (1)
Number |
Date |
Country |
Kind |
98/14398 |
Nov 1998 |
FR |
|
Parent Case Info
This is a 371 of PCT/FR99/02760 filed Nov. 10, 1999.
PCT Information
Filing Document |
Filing Date |
Country |
Kind |
102e Date |
371c Date |
PCT/FR99/02760 |
|
WO |
00 |
5/9/2001 |
5/9/2001 |
Publishing Document |
Publishing Date |
Country |
Kind |
WO00/29379 |
5/25/2000 |
WO |
A |
Foreign Referenced Citations (3)
Number |
Date |
Country |
2752840 |
Mar 1998 |
FR |
WO 9732870 |
Sep 1997 |
WO |
WO 9808834 |
Mar 1998 |
WO |
Non-Patent Literature Citations (3)
Entry |
Derwent Patent Abstract No. 230249 (1998). |
Derwent Patent Abstract No. 457482 (1997). |
Derwent Patent Abstract No. 1817401(1998). |