Oxyimino derivatives of thiazole, method of preparation and use

Details Oxyimino derivatives of thiazole, method of preparation and use Oxyimino derivatives of thiazole, method of preparation and use

1988-12-23

1990-10-02

Gerstl, Robert

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

540603, 544 60, 544133, 544367, 546209, 548204, C07D27728, C07D41712

Patent

active

049609009

ABSTRACT:
The present invention relates, by way of novel industrial products, to the ollowing oxyimino derivatives of thiazole: (a) the E and Z diastereoisomers of the formula ##STR1## in which R.sub.1 represents H, F, Cl, Br, CF.sub.3 or CH.sub.3 and R.sub.2 represents a C.sub.1 -C.sub.10 -alkyl group, a benzyl group of the formula CH.sub.2 C.sub.6 H.sub.2 (R.sub.3).sub.3, in which each R.sub.3 identical or different represents H, F,Cl,Br, CF.sub.3, a C.sub.1 -C.sub.4 -alkyl group or a C.sub.1 -C.sub.4 -alkoxy group, a group CH.sub.2 COOR.sub.4, in which R.sub.4 represents H, a C.sub.1 -C.sub.4 -alkyl group or the ammonium group, NH.sub.4.sup.+, a group CH.sub.2 COOM.sub.m, in which M is an alkali metal or alkaline earth metal and m is its valency, or a 2-aminoethyl group of the formula CH.sub.2 CH.sub.2 NR.sub.5 R.sub.6, in which R.sub.5 and R.sub.6, which can be identical or different each represent H or a C.sub.1 -C.sub.4 -alkyl group, it being possible for R.sub.5 and R.sub.6, taken together with the nitrogen atom to which they are bonded, to form a 5-to 7-membered N-heterocyclic group which may contain a second heteroatom selected from N, O and S and may be substituted, it also being possible for R.sub.2 to represent the hydrogen atom when R.sub.1 is other than H, and mixtures of the said E and Z isomers; and (b) the addition salts of the said E and Z isomers and of mixtures thereof.
These novel derivatives, as well as the compound of formula I in which R.sub.1 =R.sub.2 =H, are useful in therapy as anticonvulsants.

REFERENCES:
patent: 4363813 (1982-12-01), Kagaki
Chemical Abstracts, vol. 48, No. 6, 25/03/54, Col. 3294-95.
Suzuki, J. Pharm. Soc. Japan 73 394 (1953).

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