Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1986-03-13
1988-08-23
Gerstl, Robert
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
548195, 548197, C07D41704, A61K 31425
Patent
active
047661380
DESCRIPTION:
BRIEF SUMMARY
This invention relates to the use of 4-(isoxazolyl)-thiazol-2-oxamic acid derivatives as antiarthritic agents, their preparation, pharmaceutical composition containing them, and new 4-(isoxazolyl)-thiazole compounds.
More particularly, this invention relates to the use of the compounds of formula: ##STR1## wherein
R and R.sub.1 which may be the same or different represent a hydroxy group; a hydrogen or halogen atom; a C.sub.1 -C.sub.6 alkyl or alkoxy group optionally substituted by from one to three substituents selected from the group consisting of halogen, hydroxy, alkoxy, amino, carboxy, alkoxycarbonyl, alkoxalyloxy and phenyl, the latter in turn optionally substituted by from one to three substituents selected from the group consisting of halogen, hydroxy, alkoxy, amino and trifluoroalkyl; a phenyl group optionally substituted by from one to three substituents selected from the group consisting of halogen, hydroxy, alkoxy, amino and trifluoromethyl;
R.sub.2 is a hydroxy group, an OR.sub.3 group or an NR.sub.4 R.sub.5 group;
R.sub.3 is a C.sub.1 -C.sub.6 alkyl group optionally substituted with from one to three substituents selected from the group consisting of hydroxy, alkoxy, amino, carboxy and alkoxycarbonyl; a C.sub.5-6 cycloalkyl group optionally substituted by from one to three alkyl groups; a C.sub.7 -C.sub.9 phenylalkyl group optionally substituted on the phenyl ring by from one to three substituents selected from the group consisting of halogen, methyl and methoxy group; a group of the formula --(CH.sub.2 --CH.sub.2 --O).sub.n --R.sub.6 wherein n is an integer number from 2 to 4 and R.sub.6 is a hydrogen atom or an alkyl group; R.sub.4 and R.sub.5 which may be the same or different are a hydrogen atom, an alkyl, a C.sub.5 -C.sub.6 cycloalkyl, a C.sub.7 -C.sub.9 phenylalkyl, or a phenyl group; or R.sub.4 and R.sub.5 together with the nitrogen atom to which they are linked, form a 1-piperidyl, 1-piperazinyl, 4-methyl-1-piperazinyl, pirazolyl, thiazolyl or imidazolyl radical; or either R.sub.4 or R.sub.5 is a hydrogen atom and the other a group of the formula ##STR2## wherein
R and R.sub.1 have the above indicated meanings.
R.sub.7 is a hydrogen atom or a C.sub.1 -C.sub.3 alkyl radical.
Another object of this invention is the use of the salts of the compounds of formula I in which R.sub.2 is a hydroxy group with pharmaceutically acceptable organic and inorganic bases and the salts of the compounds of formula I in which R.sub.2 contains a basic function with pharmaceutically acceptable organic and inorganic acids.
If not otherwise specified
alkyl means a straight or branched C.sub.1 -C.sub.4 alkyl group;
alkoxy means a C.sub.1 -C.sub.4 alkoxy group;
alkoxycarbonyl means an alkoxycarbonyl group having from 1 to 4 carbon atoms in the alkoxy moiety;
halogen means fluorine, chlorine, bromine or iodine atom.
Depending on the meaning of the substituents, some of the compounds of formula I can exist in the form of isomers.
It is an object of this present invention either the use of the isomer mixtures or of the single isomers obtained by separation from the mixture or by stereospecific synthesis.
Examples of compounds included in formula I are the following ##STR3## wherein X is the group ##STR4## wherein R, R.sub.1 and R.sub.7 have the same meaning as set forth above.
Typical examples of R and R.sub.1 include fluorine, chlorine, bromine, iodine, propoxycarbonyl, ethoxycarbonyl, methoxycarbonyl, methyl, ethyl, propyl, isopropyl, hydroxypropyl, hydroxyethyl, hydroxymethyl, propyloxypropyl, propyloxymethyl, methyloxyethyl, metoxymethyl, ethoxymethyl, ethoxalyloxypropyl (--C.sub.3 H.sub.6 OCOCOOC.sub.2 H.sub.5), propoxalyloxymethyl (--CH.sub.2 OCOCOOC.sub.3 H.sub.7), ethoxalyloxymethyl (--CH.sub.2 OCOCOOC.sub.2 H.sub.5), 2-bromophenyl, 2-iodophenyl, 2-chlorophenyl, 2,6-dichlorophenyl, 2-chloro-6-fluorophenyl, methoxy, ethoxy, propoxy, phenylethoxy and benzyloxy.
Preferred meanings of R and R.sub.1 are hydrogen, chlorine, bromine, hydroxy, methyl, methoxy, ethoxy, benzyloxy, phenyl, halosubstituted phenyl hyd
REFERENCES:
patent: 4246271 (1981-01-01), Cousse
Carenzi Angelo
Chiarino Dario
Della Bella Davide
Grancini Giancarlo
Gerstl Robert
Zambon S.p.A.
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