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US 2003/0114683 A1Published application
Novel 1,3-dihydro-2h-indol-2-one derivatives and their use as ligands for v1b and v1a arginine-vasopressin receptors
AssigneeSanofi-Synthelabo
InventorsRichard Roux, Claudine Serradeil-Le Gal, Bernard Tonnerre, Jean Wagnon
Life of this patent
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Abstract
The invention relates to compounds of formula: 1 as well as the possible salts thereof with mineral or organic acids, and the solvates and/or hydrates thereof, which have affinity for and selectivity towards the V1b receptors or towards both the V1b and V1a receptors of arginine-vasopressin. The invention also relates to the process for preparing them, to the intermediate compounds of formula (II) that are useful for preparing them, to pharmaceutical compositions containing them and to their use for the preparation of medicinal products.
Claims11
Compound of formula:
- 28
- in which:
- R1 represents a halogen atom;
- a (C1-C4)alkyl;
- a (C1-C4)alkoxy;
- a trifluoromethyl radical;
- a trifluoromethoxy radical;
- R2 represents a hydrogen atom;
- a halogen atom;
- a (C1-C4) alkyl;
- a (C1-C4) alkoxy;
- a trifluoromethyl radical;
- or R2 is in position -6- of the indol-2-one ring and R1 and R2 together represent a divalent trimethylene radical;
- R3 represents a halogen atom;
- a hydroxyl;
- a (C1-C2)alkyl;
- a (C1-C2)alkoxy;
- a trifluoromethoxy radical;
- R4 represents a hydrogen atom;
- a halogen atom;
- a (C1-C2)alkyl;
- a (C1-C2)alkoxy;
- or R4 is in position -3- of the phenyl and R3 and R4 together represent a methylenedioxy radical;
- R5 represents an ethylamino group;
- a dimethylamino group;
- an azetidin-1-yl radical;
- a (C1-C2)alkoxy;
- R6 represents a hydrogen atom;
- a (C1-C4)alkyl;
- a group —(CH2)n-CO—R9;
- a group —CO—(CH2)n-NR10R11;
- R7 represents a (C1-C4)alkoxy;
- R8 represents a (C1-C4)alkoxy;
- R9 represents a hydroxyl;
- a (C1-C4)alkoxy;
- a group —NR12R13;
- R10 and R11 each independently represent a (C1-C4) alkyl;
- or R10 and R11, together with the nitrogen atom to which they are attached, constitute a heterocyclic radical chosen from:
- azetidin-1-yl, pyrrolidin-1-yl, piperid-1-yl, piperazin-1-yl, morpholin-4-yl or thiomorpholin-4-yl;
- R12 represents a hydrogen or a (C1-C4)alkyl;
- R13 represents a (C1-C4)alkyl;
- a —C(CH3)2CH2OH group;
- a —C(CH3)(CH2OH)2 group;
- a —C(CH2OH)3 group;
- or R12 and R13, together with the nitrogen atom to which they are attached, constitute a heterocyclic radical chosen from:
- azetidin-1-yl, pyrrolidin-1-yl, piperid-1-yl, piperazin-1-yl, morpholin-4-yl or thiomorpholin-4-yl;
- n is 1 or 2;
- the solvates and/or hydrates thereof and the possible salts thereof with mineral or organic acids.
45 more elements
Compound of formula:
- 32
- in which:
- R1 represents a halogen atom;
- a (C1-C4)alkyl;
- a (C1-C4)alkoxy;
- a trifluoromethyl radical;
- a trifluoromethoxy radical;
- R2 represents a hydrogen atom;
- a halogen atom;
- a (C1-C4)alkyl;
- a (C1-C4)alkoxy;
- a trifluoromethyl radical;
- or R2 is in position -6- of the indol-2-one ring and R1 and R2 together represent a divalent trimethylene radical;
- R3 represents a halogen atom;
- a hydroxyl;
- a (C1-C4)alkyl;
- a (C1-C2)alkoxy;
- a trifluoromethoxy radical;
- R4 represents a hydrogen atom;
- a halogen atom;
- a (C1-C2)alkyl;
- a (C1-C2)alkoxy;
- or R4 is in position -3- of the phenyl and R3 and R4 together represent a methylenedioxy radical;
- R5 represents an ethylamino group;
- a dimethylamino group;
- an azetidin-1-yl radical;
- a (C1-C2)alkoxy;
- R6 represents a hydrogen atom;
- a (C1-C4)alkyl;
- a group —(CH2)n-CO—R9;
- a group —CO— (CH2)n-NR10R11;
- R9 represents a hydroxyl;
- a (C1-C4)alkoxy;
- a group —NR12R13;
- R10 and R11 each independently represent a (C1-C4) alkyl;
- or R10 and R11, together with the nitrogen atom to which they are attached, constitute a heterocyclic radical chosen from:
- azetidin-1-yl, pyrrolidin-1-yl, piperid-1-yl, piperazin-1-yl, morpholin-4-yl or thiomorpholin-4-yl;
- R12 represents a hydrogen or a (C1-C4)alkyl;
- R13 represents a (C1-C4)alkyl;
- a —C(CH3)2CH2OH group;
- a —C(CH3)(CH2OH)2 group;
- a —C(CH2OH)3 group;
- or R12 and R13, together with the nitrogen atom to which they are attached, constitute a heterocyclic radical chosen from:
- azetidin-1-yl, pyrrolidin-1-yl, piperid-1-yl, piperazin-1-yl, morpholin-4-yl or thiomorpholin-4-yl;
- n is 1 or 2;
- and the salts thereof with mineral or organic acids, in the form of an optically pure isomer or in the form of a mixture of diastereoisomers.
43 more elements
Dependencies are inferred from the claim text.