5-membered heterocycles, medicaments containing these compounds, their use and processes for their preparation

A 1,3,4-thiadiazole of the formula ##STR30## wherein A is a cycloalkyl group having 5 to 7 carbon atoms, which is optionally substituted by 1 to 4 alkyl groups, in which an unsubstituted methylene group is replaced by the R.sub.a --N<

• group, which may additionally be substituted by a cyano, aminocarbonyl, carboxyl, alkoxycarbonyl or phenylalkoxycarbonyl group or alternatively, if the substitution does not take place in the .alpha.-position relative to a nitrogen atom, by a hydroxyl, alkoxy or phenylalkoxy group, and in which
• R.sub.a is a hydrogen atom, an alkyl group, a phenylalkyl group, an alkoxycarbonyl group having a total of 2 to 6 carbon atoms, a phenylalkoxycarbonyl group, an alkenyloxycarbonyl group having a total of 4 to 6 carbon atoms, a cycloalkoxycarbonyl group having a total of 6 to 8 carbon atoms or an R.sub.1 --CO--O--(R.sub.2 CH)--O--CO-- group, in which
• R.sub.1 is an alkyl group having 1 to 5 carbon atoms, a cycloalkyl group having 5 to 7 carbon atoms, a phenylalkyl group, an alkoxy group having 1 to 5 carbon atoms, a cycloalkoxy group having 5 to 7 carbon atoms or a phenyl group and
• R.sub.2 is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 7 carbon atoms or a phenyl group,
• and additionally in the 6- or 7-membered azacycloalkyl groups thus formed a >CH-- unit in the 4-position may be replaced by a nitrogen atom or in the 5- to 7-membered azacycloalkyl groups thus formed a --CH.sub.2 --CH<
• unit may be replaced by a --CH.dbd.C<
• unit and in the piperazinyl or homopiperazinyl rings thus formed one or two methylene groups, which are adjacent to the nitrogen atom in the 4-position, may in each case be replaced by a carbonyl group, or
• a quinuclidinyl group,
• B is a bond or a straight-chain or branched alkylene group having 1 to 8 carbon atoms, an alkenylene group having 2 or 3 carbon atoms, an --O(CH.sub.2).sub.n --, --(CH.sub.2).sub.n O--, --S(CH.sub.2).sub.n --, --(CH.sub.2).sub.n S--, --CONR.sub.3 --, --R.sub.3 NCO--, --NR.sub.3 (CH.sub.2).sub.n -- or --(CH.sub.2).sub.n NR.sub.3 -- group, in which
• n is the number 1 or 2 and
• R.sub.3 is a hydrogen atom, a phenylalkyl group which is optionally substituted in the phenyl nucleus by a fluorine, chlorine or bromine atom or by an alkyl, hydroxyl or alkoxy group, or is an alkyl or pyridylalkyl group,
• D is a --CO--NR.sub.3 --, --NR.sub.3 --CO--, --SO.sub.2 --NR.sub.3 --, --NR.sub.3 --SO.sub.2 --, --W--CO--NR.sub.3 --, --W.sub.1 --NR.sub.3 --CO--, --W.sub.1 --SO.sub.2 NR.sub.3 --, --W.sub.1 --NR.sub.3 SO.sub.2 --, --CO--NR.sub.3 --W.sub.1 --, --NR.sub.3 --CO--W.sub.1 --, --SO.sub.2 NR.sub.3 --W.sub.1 --, --NR.sub.3 SO.sub.2 --W.sub.1 --, --CO--(CH.sub.2).sub.n --O--, --CO--(CH.sub.2).sub.n --NR.sub.3 --, --O--W.sub.1 --, --W.sub.1 --O--, --S--W.sub.1 --, --W.sub.1 --, --W.sub.1 --S--, --NR.sub.3 --W.sub.1 --, --W.sub.1 --NR.sub.3 --, --(CH.sub.2).sub.n --O--(CH.sub.2).sub.n --, --(CH.sub.2).sub.n --NR.sub.3 --(CH.sub.2).sub.n --, --W-- or --W--CO-- group, in which
• R.sub.3 and n are defined as mentioned above,
• W.sub.1 is an alkylene group having 1 to 3 carbon atoms,
• W.sub.2 is an alkenylene group having 2 or 3 carbon atoms and
• W is an alkylene group having 1 to 3 carbon atoms or an alkenylene group having 2 or 3 carbon atoms,
• E is a phenylene group which may be mono- or disubstituted by fluorine, chlorine or bromine atoms, or by alkyl, trifluoromethyl, R.sub.3 O-- or R.sub.3 O--CO--CH.sub.2 --O-- groups, it being possible for the substituents to be identical or different and R.sub.3 being defined as mentioned above,
• a pyridinylene, pyrimidinylene, pyrazinylene, pyridazinylene or triazinylene group, each of which may be substituted in the carbon ring system by a chlorine atom or by an alkyl or alkoxy group, it additionally being possible for one or two --CH.dbd.N-- groups each to be replaced by a --CO--NR.sub.3 -- group, in which R.sub.3 is defined as mentioned above, and one of the nitrogen atoms may also be bonded to the radical F, instead of to the radical R.sub.3, if this is not a bond,
• a cycloalkylene group having 4 to 5 carbon atoms, which is optionally substituted by an alkyl, phenylalkyl or phenyl group, in which a >CH-- unit may be replaced by a nitrogen atom and additionally a methylene group adjacent to the nitrogen atom may be replaced by a carbonyl group, or
• a cycloalkylene group, having 6 or 7 carbon atoms which is optionally substituted by an alkyl, phenylalkyl or phenyl group, in which one or two >CH-- units may each be replaced by a nitrogen atom, it additionally being possible for a methylene group adjacent to a nitrogen atom to be replaced by a carbonyl group,
• F is a bond, a straight-chain or branched alkylene or alkenylene group, which is optionally substituted by a phenylalkyl, phenyl, pyridyl, R.sub.3 O--, R.sub.3 S--, R.sub.3 R.sub.3 N--, R.sub.3 O--CO--, R.sub.3 R.sub.3 N--CO--, R.sub.4 CO--NR.sub.3 --, R.sub.5 O--CO--NR.sub.3 --, R.sub.4 SO.sub.2 --NR.sub.3 --, R.sub.3 R.sub.3 N--CO--NR.sub.3 --, R.sub.3 O--CO--C.sub.1-3 -alkyl or R.sub.3 R.sub.3 N--CO--C.sub.1-3 -alkyl group, in which in each case the alkylene moiety may contain 1 to 5 carbon atoms and the alkenylene moiety may contain 2 to 5 carbon atoms, or a --Y--W.sub.1 -- group, in which
• R.sub.3 and W.sub.1 are defined as mentioned above,
• R.sub.4 is an alkyl group having 1 to 5 carbon atoms, or a phenylalkyl, phenyl or pyridyl group,
• R.sub.5 is an alkyl group having 1 to 5 carbon atoms, a phenylalkyl, cycloalkyl or cycloalkylalkyl group and
• Y is an oxygen atom, a --CO--, sulphenyl-, sulphinyl-, sulphonyl-, --NR.sub.3 --, --N(COR.sub.4)--, --N(SO.sub.2 R.sub.4)--, --CO--NR.sub.3 -- or --NR.sub.3 --CO-- group, Y being linked to the radical E, with the proviso that a heteroatom of the radical E is not bonded to a nitrogen or sulphur atom of the above groups,
• and R.sub.b is an alkyl group having 1 to 5 carbon atoms or a cycloalkyl group having 5 to 7 carbon atoms in the cycloalkyl moiety, it being possible for the above-mentioned groups each to be substituted in the alkyl and cycloalkyl moiety from position 2 by an R.sub.3 O-- or R.sub.3 R.sub.3 N-- group, or is an alkenyl group having 3 to 5 carbon atoms, a phenylalkyl group, a cycloalkyl-alkyl group having 3 to 7 carbon atoms in the cycloalkyl moiety, which may be substituted in the alkyl moiety from position 2 by an R.sub.3 O-- or R.sub.3 R.sub.3 N-- group, R.sub.3 in each case being defined as mentioned above, an R.sub.1 --CO--O--(R.sub.2 CH)-- group, in which R.sub.1 and R.sub.2 are defined as mentioned above, or alternatively a hydrogen atom if the R.sub.b O--CO-- group is not directly bonded to a nitrogen atom of the radical E,
• the distance between the furthest removed nitrogen atom of the group A and the COOR.sub.b group being at least 11 bonds,
• where, if nothing different has been mentioned,
• the above-mentioned alkyl, alkylene or alkoxy moieties may each contain 1 to 3 carbon atoms and the above-mentioned cycloalkyl moieties may each contain 3 to 7 carbon atoms,
• or a tautomer or physiologically tolerable salt thereof.