Ciba-geigy Corporation

Atso Ilvespaa

Jorg Frei

Ernst Schweizer

Walter Fuhrer

Georges Haas

Andre Gagneux

The invention relates to novel thiopyrones, especially novel benzothiopyranones of the general formula ##STR1## in which R.sub.1 represents hydrogen or an aliphatic radical, n represents 0, 1 or 2, Ph represents substituted or unsubstituted 1,2-phenylene and A represents a group of the formula --NH--CO--R in which R represents carboxy or esterified carboxy, and to their salts, processes for the manufacture of compounds of the formula (I) and their salts, pharmaceutical preparations containing such compounds and to the use of compounds of the formula (I) and their salts as the active ingredients of medicaments and/or for the manufacture of pharmaceutical preparations. The compounds of the formula (I) and their salts have anti-allergic properties.

Anti-allergic 3-(carboxycarbonyl)amino benzothiopyran-4-one derivatives,

The invention relates to guanidine derivatives, particularly to substituted guanidines of the formula ##STR1## having hypoglycaemic activity, for the oral treatment of hyperglycaemia in mammals, especially for the oral treatment of Diabetes mellitus.

Guanidine compounds, pharmaceutical compositions and use

The present invention provides new imino compounds having the formula I ##STR1## wherein R.sub.1 represents an aliphatic or cycloaliphatic hydrocarbon radical, unsubstituted or substituted phenyl, or phenyl-lower alkyl or diphenyl-lower alkyl, which radicals are unsubstituted or substituted in the phenyl ring(s),

Imino compounds

2-(Iminoethylidene)-pyrrolidines and tautomeric

Imidazoles of the formula I ##STR1## wherein one of the radicals R.sub.1 and R.sub.2 denotes hydrogen or lower alkyl and the other denotes the nitro group, R.sub.3 is lower alkyl, hydroxy-lower alkyl, lower alkoxy-lower alkyl, lower alkylsulphonyl-lower alkyl or amino-lower alkyl, R.sub.4 is oxo or thioxo, R.sub.5 -- if R.sub.1 is the nitro group -- is hydrogen, lower alkyl, hydroxy-lower alkyl, lower alkoxy-lower alkyl, amino-lower alkyl, acyl, aryl or a heterocyclic radical or R.sub.5 -- if R.sub.2 is the nitro group -- is aryl or a heterocyclic radical, with the exception of an optionally substituted 2-imidazolyl group, and alk is lower alkylene and their therapeutically usable salts, S-oxides, sulphones or N-oxides are useful as agents against amoebae, schistosomes, filariae, trichomonades and bacteria and as intermediates.

Imidazoles and pharmaceutical composition

Amines of the formula Ia ##STR1## WHEREIN A is a 1- or 2-[9,10-dihydro-9,10-ethono(or etheno)anthryl] radical, especially of the formula Ib ##STR2## WHEREIN Ph denotes an optionally substituted o-phenylene radical, Z represents an optionally lower-alkylated ethylene or ethenylene radical, R.sub.3 denotes lower alkyl radicals, lower alkoxy radicals, hydroxyl groups, nitro groups, amino groups, trifluoromethyl groups, nitrile or halogen atoms or above all hydrogen and n represents the numbers 1, 2 or 3, R.sub.1 denotes hydrogen or lower alkyl and R.sub.2 is hydrogen, lower alkyl, aryl-lower alkyl or optionally functionally modified carboxy-lower alkyl, or R.sub.1 and R.sub.2 together represent a divalent hydrocarbon radical of aliphatic character which can optionally be interrupted by hetero-atoms and/or be substituted, which are valuable excitations inhibitors and nacosic-boosting compounds.

1- OR 2-[2-Hydroxy-3-amino-propoxy]-9,10-dihydro-9,10-ethano-anthracenes

4- or 5-nitro-imidazoles of the formula I ##SPC1## wherein one of the radicals R.sub.1 and R.sub.2 is hydrogen or lower alkyl and R.sub.2 is the nitro group or R.sub.1 is the nitro group and R.sub.2 is hydrogen or lower alkyl, R.sub.3 is lower alkyl, hydroxy-lower alkyl, lower alkoxy-lower alkyl, lower alkylsulphonyl-lower alkyl, dilower alkylamino-lower alkyl, lower alkylene-amino-lower alkyl, lower oxaalkyleneamino-lower alkyl, lower thiaalkyleneamino-lower alkyl or lower azaalkyleneamino lower alkyl, R.sub.4 is oxo or thioxo and R.sub.5 is a phenyl radical which optionally has one, two or more substituents, an optionally substituted furyl, thienyl, pyrrolyl, indolyl, oxazolyl, thiazolyl, thiadiazolyl, 4,5-dihydro-thiazolyl-(2), tetrahydro-thiazolyl-(2), pyrazolyl, indazolyl, imidazolyl-(5), imidazolyl-(4), pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, 1,3,5- or 1,2,4-triazinyl, pyrrolidinyl, pyrazolinyl, indolinyl, pyrazolidinyl, imidazolinyl, imidazolidinyl, piperidyl, morpholinyl, thiazinyl, thiomorpholinyl or piperazinyl radical, an optionally C-lower alkylated pyrrolidino, piperidino, morpholino, thiomorpholino, piperazino, N'-lower alkyl-piperazino, N'-.beta.-hydroxyethyl-piperazino or pyridinium radical and R.sub.6 and R.sub.7 independently of one another denote hydrogen or lower alkyl or conjointly form the missing part of a fused benzene nucleus which is optionally substituted by lower alkyl, lower alkoxy, halogen, trifluoromethyl and/or nitro, as well as their S-oxides, sulphones N-oxides and/or acid addition salts thereof, which are useful as agents against schistosomes, filaria, trichomonades, bacteriae, and/or amoebae.

4- or 5-Nitroimidazoles and processes for their manufacture

Cpmpounds of the class of 5-substituted and 5,6-disubstituted 2-amino-4-(hydroxyamino) and 2,4-bis-(hydroxyamino)pyrimidines and their pharmaceutically acceptable acid addition salts possess valuable biological properties, in particular antibacterial and antimalarial activity and potentiate the action of antibacterial sulphanilamide derivatives. Specific embodiments are 2-amino-4-(hydroxyamino)-5-(3,4,5-trimethoxybenzyl)-pyrimidine, and 2-amino-4-(hydroxyamino)-5-(p-chlorophenyl)-6-ethyl pyrimidine and its hydrochloride.

Substituted 2-amino-4-(hydroxyamino)-pyrimidines

Compounds of the class of 1-heteroarylsulphonyl-2-imino-imidazolidines which are substituted in the 3-position by an aliphatic or cycloaliphatic hydrocarbon radical, especially a cycloalkyl radical, and their pharmaceutically acceptable acid addition salts have valuable pharmacological properties. In particular, they possess hypoglycaemic activity and can be used for the treatment of hyperglycaemia in mammals. A specific embodiment is 1-[5-(2-butyramido-ethyl)-2-thienylsulphonyl]-2-imino-5-cyclohexyl-imidazo lidine.

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Allschwil, Switzerland

Atso Ilvespaa