Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Patent
1992-12-04
1994-08-09
Shah, Mukund J.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
5142332, 5142282, 514253, 514301, 546114, 540544, 544 61, 544145, 544215, 544333, A61K 3154, A61K 31535, A61K 31495, A61K 3150
Patent
active
053366760
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to [3H, 7H]thiazolo[3,4-a]-pyridines, a method for preparing them and pharmaceutical compositions which contain them.
More precisely the invention relates to compounds of formula (I) ##STR2## in which: R is (C.sub.1 -C.sub.4) alkyl; hydroxyaminocarbonyl group or a carboxyamide group of the formula ##STR3## wherein Ra and Rb are as defined below or a group of the formula ##STR4## wherein q is an integer from 2 to 4; R.sub.c is hydrogen, C.sub.1 -C.sub.6) alkyl, benzyl; Rd is hydrohydrogen or (C.sub.1 -C.sub.6) alkyl or Rc and Rd, taken together with the nitrogen atom, form a pyrrolidine, piperidine, morpholine, thiomorpholine, (C.sub.1 -C.sub.4) alkylpiperazine R.sub.2 is a (C.sub.3 -C.sub.7) cycloalkyl group, .alpha., .beta. or .gamma.-pyridyl, substituted or unsubstituted phenyl or a bicyclic ring in which a benzene ring is fused to a 5- or 6-membered heterocyclic ring containing one or more heteroatoms selected from O, S and N, said bicyciic ring being preferably bound via the benzene ring; --CONR.sub.a R.sub.b or ##STR5## group defined above; Y is one of the following groups: COOX; --NHCOA; --NCO; --COA; --CONHOR.sub.e ; --OCOA; A; --CO--CH.sub.2 --CO--R.sub.f ; --NHCSA; ##STR6## R.sub.e is hydrogen, (C.sub.1 -C.sub.6) alkyl, or substituted or unsubstituted phenyl or benzyl; R.sub.f is (C.sub.1 -C.sub.6) alkoxy, ##STR7## group wherein R.sub.a and R.sub.b are as defined below or a (pyridin-2-yl)amino group; X is hydrogen, (C.sub.1 -C.sub.4) alkyl, allyl, propargyl or an N-succinimidyl group of formula ##STR8## wherein R.sub.a or R.sub.b, which are the same or different, are hydrogen, (C.sub.1 -C.sub.4) alkyl, allyl, propargyl, (C.sub.3 -C.sub.7) cycloalkyl, unsubstituted or substituted phenyl, benzyl unsubstituted or subs tituted by hydroxy and/or methoxy groups, benzhydryl unsubstituted or substituted by halogens or, taken together with the nitrogen atom, they form an aziridine, azetidine group or a ring of formula ##STR9## wherein Z is O, S, CH.sub.2 or -S-S- or a ring of formula ##STR10## wherein B is hydrogen, (C.sub.1 -C.sub.4) alkyl, benzyl unsubstituted or substituted by hydroxy and/or alkoxy groups, benzhydryl unsubstituted or substituted by halogen atoms, unsubstituted or substituted phenyl, 5- to 6-membered heterocycle with 1-3 nitrogen atoms unsubstituted or substituted by 1 or 2 amine, monoalkyl- , monoalkenyl- or monoalkynyl-amine, dialkylamine, alkylalkenylamine, piperidin-1-yl, morpholin-4-yl, pyrrolidin-1-yl groups; n is the integer 1 or 2.
The expression "unsubstituted or substituted phenyl" as used above refers to a phenyl ring containing from 1 to 3 substituents selected from the group of (C.sub.1 -C.sub.4) alkyl such as methyl, ethyl, propyl, isopropyl, tert-butyl; (C.sub.1 -C.sub.4) alkoxy such as methoxy, ethoxy or propoxy; (C.sub.1 -C.sub.4) alkylthio such as methylthio, ethylthio; phenoxy; 4-hydroxyphenoxy; phenylthio; 4-hydroxyphenylthio; halogen atoms (chlorine, bromine, fluorine); the following groups: cyano, azide, nitre, amine, (C.sub.1 -C.sub.6) acylamino, trihaloacetylamino such as trifluoroacetylaminc, methane- or trifluoromethanesulphonamido, benzene- or para-tolyl-sulphonamido, trihalomethyl, dihalomethoxy such as difluoromethoxy, trifluoromethoxy groups , a free or salified carboxy group and (C.sub.1 -C.sub.4) alkoxycarbonyl.
Particularly preferred examples of mono- and/or polysubstituted phenyl groups are those bearing the following substitutions: 2-chloro-, 3-chloro-, 4-chloro-, 2 , 3-dichloro-, 2-fluere-, 2-fluoro-3-chloro-, 2-nitre-, 6-fluere-2,3-dichloro-, 3-nitre-, 3-nitro-4-phenoxy-, 4-nitr0-, 4-nitro-3-phenoxy-, 2-trifluoromethyl-, 3-trifluoromethyl- , 3-cyano-, 3-methoxy-, 2amino- , 3-amino- , 4-amine-, 2-methanesulphonamido-, 3-methanesulphonamido-, 4-methanesulphonamido-, 3-methanesulphonamido-4-phenoxy-, 4-methanesulphonamido-3phenoxy-, 4-fluoro-2,3 -dichloro- , 3-carboxy-4-hydroxy-, 3-hydroxy-4-carboxy- and combinations thereof.
When R.sub.2, R.sub.a or R.sub.b are a ( C.sub.3 -C.sub.7) cycloalkyl group, this is preferably cycl
REFERENCES:
patent: 4946955 (1990-08-01), Hosomi
De Cillis Giampiero
Gallico Licia
Gandolfi Carmelo A.
Long Giorgio
Boehringer Mannheim Italia S.p.A.
Grumbling Matthew V.
Shah Mukund J.
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