Use of 2-amino-4-pyridylmethyl-thiazoline derivatives as inhibitors of inducible NO-synthase
AssigneeAventis Pharma S. A.
InventorsEric Bacque, Antony Bigot, Jean-Christophe Carry, Serge Mignani, Baptiste Ronan, Michel Tabart
Life of this patent
Estimating the term…
Abstract
The present invention relates to the use of 2-amino-4-pyridylmethyl thiazoline derivatives of formula (I) 1 wherein either R1=R2=Cl or (C1-C4)alkyl, or hydroxy; or (C1-C4)alkoxy or at least one of R1 or R2 is a hydrogen and the other is a (C1-C4)alkyl, hydroxy, (C1-C4)alkoxy or chlorine or pharmaceutically acceptable salts thereof as inhibitors of inducible NO-synthase.
Claims25
A compound of formula (I):
- 19
- wherein
- R1 and R2 are the same and are selected from the group consisting of hydroxy, (C1-C4)alkyl, chlorine and (C1-C4)alkoxy;
- or
- at least one of R1 or R2 is a hydrogen and the other is a (C1-C4)alkyl, (C1-C4)alkoxy, hydroxy or chlorine;
- and
- wherein the (C1-C4)alkyl and (C1-C4)alkoxy contain 1 to 4 carbon atoms in straight or branched chain;
- or
- a racemate, an enantiomer, a diastereoisomer thereof or a mixture thereof or a tautomer thereof or a pharmaceutically acceptable salt thereof.
A pharmaceutical composition comprising, as active ingredient, at least one compound of formula (I):
- 20
- wherein
- R1 and R2 are the same and are selected from the group consisting of hydroxy, (C1-C4)alkyl, chlorine and (C1-C4)alkoxy;
- or
- at least one of R1 or R2 is a hydrogen and the other is a (C1-C4)alkyl, (C1-C4)alkoxy, hydroxy or chlorine;
- and
- wherein the (C1-C4)alkyl and (C1-C4)alkoxy contain 1 to 4 carbon atoms in straight or branched chain;
- or
- a racemate, an enantiomer, a diastereoisomer thereof or a mixture thereof or a tautomer thereof or a pharmaceutically acceptable salt thereof, optionally in combination with a pharmaceutically acceptable carrier.
A method of treating an illness, which involves an abnormal production of nitric oxide (NO) by induction of an inducible NO-synthase (NOS-2), comprising administering to a patient in need of such a treatment a therapeutically effective amount of a compound of formula (I):
- 21
- wherein
- R1 and R2 are the same and are selected from the group consisting of hydroxy, (C1-C4)alkyl, chlorine and (C1-C4)alkoxy;
- or
- at least one of R1 or R2 is a hydrogen and the other is a (C1-C4)alkyl, (C1-C4)alkoxy, hydroxy or chlorine;
- and
- wherein the (C1-C4)alkyl and (C1-C4)alkoxy contain 1 to 4 carbon atoms in straight or branched chain;
- or
- a racemate, an enantiomer, a diastereoisomer thereof or a mixture thereof or a tautomer thereof or a pharmaceutically acceptable salt thereof, optionally in combination with a pharmaceutically acceptable carrier.
A process for preparing a compound of formula (I), including a racemic mixture, an enantiomer, a diastereoisomer or a mixture of said enantiomer or said diastereomer, or a tautomer thereof:
- 22
- comprising the step of cyclizing a compound of formula (II) under suitable reaction conditions such that said compound of formula (II) cyclizes to form said compound of formula (I);
- 23
- and isolating said compound of formula (I);
- wherein
- R1 and R2 are the same and are selected from the group consisting of hydroxy, (C1-C4)alkyl, chlorine and (C1-C4)alkoxy;
- or
- at least one of R1 or R2 is a hydrogen and the other is a (C1-C4)alkyl, (C1-C4)alkoxy, hydroxy or chlorine;
- and
- wherein the (C1-C4)alkyl and (C1-C4)alkoxy contain 1 to 4 carbon atoms in straight or branched chain.
Dependencies are inferred from the claim text.