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Generated: August 24, 2017

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Title: Imidazo[1,2-a] pyridine derivatives and their application as pharmaceuticals
Abstract:Imidazo[1,2-a] pyridines of the formula: ##STR1## and their acid addition salts in which Y represents a hydrogen or halogen atom or a C.sub.1-4 alkyl radical, Z represents a naphthyl radical or a radical ##STR2## in which each of X.sub.1 and X.sub.2 independently of one another is a hydrogen or halogen atom, a C.sub.1-4 alkoxy radical, a C.sub.1-6 alkyl radical or CF.sub.3, CH.sub.3 S--, CH.sub.3 SO.sub.2 --, --NO.sub.2, --NH.sub.2 or --NHCOCH.sub.3, and each of R.sub.1 and R.sub.2 independently of one another represents a hydrogen atom, a straight or branched C.sub.1-5 alkyl radical which is unsubstituted or substituted by one or more halogen atoms or hydroxyl, --N(C.sub.1-4 alkyl).sub.2, carbamoyl or C.sub.1-4 alkoxy radicals, allyl, propargyl, a C.sub.3-6 cycloalkyl radical, benzyl, or phenyl, not both R.sub.1 and R.sub.2 being hydrogen, or --NR.sub.1 R.sub.2 represents a heterocyclic ring containing from 3 to 6 carbon atoms, or a heterocyclic ring of the formula ##STR3## in which X is O, S, CHOR' or >N--R, R' being hydrogen or benzyl and R being hydrogen, a C.sub.1-4 alkyl radical, or phenyl which is unsubstituted or substituted by methoxy or a halogen atom, which may be made from the corresponding acids, have valuable pharmacological properties, especially anxiolytic, anti-anoxic, sleep-inducing, hypnotic and anticonvulsant properties.
Inventor(s): Kaplan; Jean-Pierre (Bourg la Reine, FR), George; Pascal (Vitry sur Seine, FR)
Assignee: Synthelabo (Paris, FR)
Application Number:06/313,601
Patent Claims: 1. A compound of the formula ##STR39## wherein X.sub.1 is halogen or methyl;

Y is hydrogen, halogen or methyl;

R.sub.1 is hydrogen, C.sub.1-5 alkyl or hydroxy (C.sub.1-5 alkyl); and

R.sub.2 is C.sub.1-5 alkyl or hydroxy (C.sub.1-5 alkyl)

or a pharmaceutically acceptable salt thereof.

2. An imidazo[1,2-a]pyridine according to claim 1, in which R.sub.1 and R.sub.2 are both alkyl radicals.

3. An imidazo[1,2-a]pyridine according to claim 2, in which Y is chlorine or methyl.

4. A method of providing a patient with a hypnotic effect which comprises administerinng to said patient a hypnotically-effective amount of a compound of the formula: ##STR40## wherein X.sub.1 is halogen or methyl;

Y is hydrogen, halogen or methyl;

R.sub.1 is hydrogen, C.sub.1-5 alkyl or hydroxy (C.sub.1-5 alkyl); and

R.sub.2 is C.sub.1-5 alkyl or hydroxy (C.sub.1-5 alkyl)

or a pharmaceutically acceptable salt thereof.

5. A method of claim 4 wherein R.sub.1 and R.sub.2 are alkyl.

6. A method of claim 5 wherein Y is chlorine or methyl.

7. A method of providing a patient with an anxiolytic effect which comprises administering to said patient an anxioloytically-effective amount of a compound of the formula: ##STR41## wherein X.sub.1 is halogen or methyl;

Y is hydrogen, halogen or methyl;

R.sub.1 is hydrogen, C.sub.1-5 alkyl or hydroxy (C.sub.1-5 alkyl); and

R.sub.2 is C.sub.1-5 alkyl or hydroxy (C.sub.1-5 alkyl) or a pharmaceutically acceptable salt thereof.

8. A method of claim 7 wherein R.sub.1 and R.sub.2 are alkyl.

9. A method of claim 8 wherein Y is chlorine or methyl.

10. A method of providing a patient with an anticonvulsive effect which comprises administering to said patient an anticonvulsive dosage of a compound of the formula: ##STR42## wherein X.sub.1 is halogen or methyl;

Y is hydrogen, halogen or methyl;

R.sub.1 is hydrogen, C.sub.1-5 alkyl or hydroxy (C.sub.1-5 alkyl); and

R.sub.2 is C.sub.1-5 alkyl or hydroxy (C.sub.1-5 alkyl) or a pharmaceutically acceptable salt thereof.

11. A method of claim 10 wherein R.sub.1 and R.sub.2 are alkyl.

12. A method of claim 11 wherein Y is chlorine or methyl.
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