Claims
- 1. Compound, optionally in the form of a pure optical isomer or a mixture of such isomers, corresponding to the general formula (I) in whichR1 represents a hydrogen atom or a (C1-C4)alkyl or cyclo(C3-C7)alkylmethyl group, X1 represents a hydrogen or halogen atom or a (C1-C4)alkoxy group, or alternatively OR1 and X1 together represent a group of formula —OCH2O—, —O(CH2)2—, —O(CH2)3—, —O(CH2)2O— or —O(CH2)3O—, X2 represents a hydrogen atom, an amino group or a group of general formula —NHCO2R in which R represents a (C1-C4)alkyl or phenyl(C1—C2)alkyl group, X3 represents a hydrogen or halogen atom, and R2 represents a hydrogen atom or a (C1-C6)alkyl group, or a phenyl(C1-C4)alkyl or [(4-dimethylamino)piperid-1-ylcarbonyl] (C2-C4) alkyl group, in the form of a base or an addition salt with an acid.
- 2. Process for the preparation of a compound according to claim 1, wherein an ester of general formula (II) in which R1, X1, X2 and X3 are as defined in claim 1 and R3 represents a methyl or ethyl group, is reacted with hydrazine hydrate, in order to obtain a hydrazide of general formula (III) which is cyclized into an oxadiazole of general formula either using phosgene, in an aprotic solvent, or using phenyl chloroformate, in an aprotic solvent, after which the oxadiazole of general formula (IV) is reacted with an alcohol of general formula (V) in which Boc represents a (1,1-dimethylethoxy)carbonyl group, in the presence of triphenylphosphine and ethyl azodicarboxylate, in an aprotic solvent, in order to obtain a compound of general formula (I) in which R2 represents a hydrogen atom, and, finally, the latter compound is subjected to an alkylation using a derivative of general formula R2-X, in which X represents a leaving group, and R2 is as defined in claim 1, but is other than a hydrogen atom.
- 3. Pharmaceutical composition, which contains a compound according to claim 1, combined with an excipient.
- 4. A method for treating an amenable disorder in which a 5-HT4 receptor is involved, which comprises administering an effective amount of a pharmaceutically acceptable compound according to claim 1 to a subject in need of such therapy.
- 5. A method for treating an amenable disorder in which a 5-HT4 receptor is involved, which comprises administering an effective amount of a pharmaceutically acceptable compound according to claim 3 to a subject in need of such therapy.
Priority Claims (1)
Number |
Date |
Country |
Kind |
97 05539 |
May 1997 |
FR |
|
Parent Case Info
This application is a 371 of PCT/FR98/00887 filed May 4, 1998.
PCT Information
Filing Document |
Filing Date |
Country |
Kind |
102e Date |
371c Date |
PCT/FR98/00887 |
|
WO |
00 |
11/4/1999 |
11/4/1999 |
Publishing Document |
Publishing Date |
Country |
Kind |
WO98/50381 |
11/12/1998 |
WO |
A |
US Referenced Citations (1)
Number |
Name |
Date |
Kind |
5525619 |
Koenig et al. |
Jun 1996 |
|
Foreign Referenced Citations (3)
Number |
Date |
Country |
WO9316072 |
Aug 1993 |
WO |
WO9532965 |
Dec 1995 |
WO |
WO9717345 |
May 1997 |
WO |