DE3942581A1 - New 2-amino-thiazole derivs. - Google Patents

Abstract

2-Aminothiazoles of formula (I) and their tautomers are new: R1 = NH2 or N=C(T1)-NT2T3; T1 = H, 1-6C alkyl or Ph; T2 and T3 = 1-6C alkyl, 5-7C cycloalkyl or Ph, or NT2T3 is a satd. 5- to 7-membered ring opt. contg. other heteroatoms; R3 = S(O)nX, SH or Y; n = 0-2; X = 3-8C cycloalkyl or opt. substd. 1-20C alkyl, 3-6C alkenyl, 3-6C alkynyl or phenyl; Y = 1-20C mono- or dialkylamino (opt. substd. and/or interrupted by O), 3-8C cycloalkylamino, adamantylamino, 2-12C mono- or dialkenylamino, 3-12C alkynylamino, N-(1-5C alkyl)anilino, pyrrolidino, piperidino, morpholino, thiomorpholino, 1-piperazinyl, 4-(1-4C alkyl)-1-piperazinyl, hexamethylenimino, 1-imidazolyl, 1-pyrazolyl, opt. substd. anilino, pyridylamino, thienylamino, NHNH2, 1-4C mono- or dialkylhydrazino or phenylhydrazino; R4 = 1-6C alkanoyl, benzoyl, CN, COT4 or C(T6)T5; T4 = OH, 1-6C alkoxy, NH2 or Y; T5 = H, 1-6C alkyl or Ph; T6 = NOH, NQ or the residue of a cpd. contg. a reactive CH2 gp.; Q = opt. substd. 1-20C alkyl (opt. interrupted by O), an opt. substd. 3-6C alkenyl, 3-6C alkynyl, 3-12C cycloalkyl or phenyl gp., pyridyl, 3-6C alkoxycarbonylmethyl, NH2, dialkylamino or anilino; provided that: (a) R3 is not SCH(COMe)COOETt or SCH(COMe)2 when R1 = NH2 and R4 = COMe or COOEt; (b) R3 is not SMe when R1 = NH2 and R4 = CN; (c) R1 is not NH2 when R3 = piperidino or morpholino and R4 = CN.

Description

The present invention relates to new diaminothiazoles of the formula I.

or their tautomers, where
R¹ and R² are each hydrogen or together a radical of the formula

wherein T¹ for hydrogen, C₁-C₆-alkyl or phenyl and T² and T³ are the same or different and independently of each other for C₁-C₆-alkyl, C₅-C₇-cycloalkyl or phenyl or T² and T³ together with the nitrogen atom connecting them for one 5- to 7-membered saturated heterocyclic radical which optionally contains further heteroatoms,
R³ C₁-C₂₀-mono- or dialkylamino, in which the alkyl chain is optionally substituted and / or interrupted by one or more oxygen atoms, C₃-C₈-cycloalkylamino, adamantylamino, C₂-C₁₂-mono- or dialkenylamino, C₃-C₁₂-alkynylamino, N. - (C₁-C₅-alkyl) -N-phenylamino, pyrrolidino, piperidino, morpholino, thiomorpholino, piperazino, N- (C₁-C₄-alkyl) piperazino, hexamethyleneimino, imidazol-1-yl, pyrazol-1-yl, optionally substituted Phenylamino, pyridylamino, thienylamino, hydrazino, C₁-C₄ mono- or dialkylhydrazino or phenylhydrazino and
R⁴ C₁-C₆ alkanoyl, benzoyl, cyano or a radical of the formula

mean in which T⁴ is hydroxy, C₁-C₆-alkoxy, amino or the radical R³, T⁵ is hydrogen, C₁-C₆-alkyl or phenyl and T⁶ is the radical of a methylene-active compound, hydroxyimino or the radical NX, in which X is The meaning of C₁-C₂₀-alkyl which is optionally substituted and / or interrupted by one or more oxygen atoms, optionally substituted C₃-C₆-alkenyl, optionally substituted C₃-C₆-alkynyl, optionally substituted C₃-C₁₂-cycloalkyl, optionally substituted phenyl, Possesses pyridyl, C₁-C₄-alkoxycarbonylmethyl, amino, C₁-C₄-dialkylamino or phenylamino,
with the proviso that when R³ is piperidino or morpholino and R⁴ is cyano, R¹ and R² are not simultaneously hydrogen.

2,4-Diaminothiazole derivatives which are in ring position 2 are already known a substituted amino group, in ring position 4 a piperidino or Morpholino group and in ring position 5 have a cyano group (see e.g. B. Tetrahedron Lett. Volume 22, pages 2285 to 2288, 1981). The above However, diaminothiazoles are not particularly suitable as diazo components for the production of azo dyes.

The object of the present invention was now to develop new diaminothiazoles provide the unsubstituted amino group in ring position 2 and should have a substituted amino group in ring position 4.

Accordingly, the diaminothiazoles of the formula I specified above found.

All alkyl and alkenyl groups occurring in the above formula I. can be straight or branched.

If in the formula I alkyl groups occur by one or more Oxygen atoms are interrupted, those are preferred, which are separated by one three, in particular one or two oxygen atoms are interrupted.

If substituted phenyl groups occur in the formula I, as Substituents e.g. B. C₁-C₆ alkyl, C₁-C₆ alkoxy, halogen, in particular Fluorine, chlorine or bromine, nitro, hydroxy, amino, C₁-C₆ mono- or dialkylamino, Acetylamino, carboxyl, carbamoyl, thiocarbamoyl, cyano, C₁-C₆- Alkoxycarbonyl, trifluoromethyl, hydroxy-C₁-C₃-alkyl or C₁-C₄-alkanoyl in Come into consideration.

If substituted alkyl groups occur in the formula I, as Substituents e.g. B. hydroxy, C₁-C₆-alkoxy, phenyl-C₁-C₄-alkoxy, phenoxy, Amino, C₁-C₆-mono- or dialkylamino, phenyl-C₁-C₆-alkylamino, diphenyl-  C₁-C₄ alkylamino, phenylamino, diphenylamino, C₃-C₆ mono- or dicyclo alkylamino, C₃-C₆-cycloalkyl, hydroxy-C₁-C₆-alkylamino, morpholino, Piperazino, N- (C₁-C₆-alkyl) piperazino, thiomorpholino, piperidino, Pyrrolidino, hexamethyleneimino, thien-2-yl, furan-2-yl, 1H-pyrrol-2-yl, Pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, carboxyl, C₁-C₃ alkoxycarbonyl, Carbamoyl, mono-dialkylcarbamoyl, cyano, thiocarbamoyl, phenoxycarbonyl, Phenyl-C₁-C₄-alkoxycarbonyl, mono- or diphenylcarbamoyl, mono- or Bis (phenyl-C₁-C₄-alkyl) carbamoyl, mono- or diphenylthiocarbamoyl, mono- or bis (phenyl-C₁-C₄-alkyl) thiocarbamoyl, C₁-C₆-alkylthio, phenylthio or phenyl-C₁-C₄-alkylthio.

When substituted in formula I alkenyl, alkynyl or cycloalkyl groups can occur as substituents such. B. fluorine, chlorine or bromine in Come into consideration.

When the residues T² and T³ together with the nitrogen atom connecting them a 5- to 7-membered saturated heterocyclic radical which, if appropriate contains further heteroatoms, mean z. B. Pyrrolidino, Piperidino, Morpholino, Thiomorpholino, Thiomorpholino-S, S- dioxide, piperazino, N- (C₁-C₄-alkyl) piperazino or hexamethyleneimino in Come into consideration.

T¹, T², T³ and T⁵ are, for example, methyl, ethyl, propyl, Isopropyl, butyl, isobutyl, sec-butyl, pentyl, isopentyl, neopentyl, tert-pentyl or hexyl.

R⁴ are for example formyl, acetyl, propionyl, butyryl, iso butyryl, pentanoyl or hexanoyl.

The terms used below isooctyl, isononyl, isodecyl and isotridecyl are trivial names and come from the after the Alcohols obtained by oxosynthesis (cf. Ullmanns encyclopedia of technical chemistry, 4th edition, volume 7, pages 215 to 217, and volume 11, Pages 435 and 436).

The rest -NX is derived from primary amines of the formula H₂NX. As such are, for example, methylamine, ethylamine, propylamine, isopropylamine, Butylamine, isobutylamine, sec-butylamine, tert-butylamine, pentylamine, Isopentylamine, neopentylamine, hexylamine, heptylamine, n-octylamine, isooctylamine, 2-ethylhexylamine, nonylamine, isononylamine, decylamine, isodecylamine, Undecylamine, dodecylamine, tridecylamine, isotridecylamine, tetradecylamine, Pentadecylamine, hexadecylamine, heptadecylamine, octadecylamine, Nonadecylamine, eicoxylamine, allylamine, methallylamine, propargylamine, Cyclopropylamine, cyclobutylamine, cyclopentylamine, cyclohexylamine, cycloheptylamine,  Cyclooctylamine, cyclononylamine, cyclodecylamine, cycloundecylamine, Cyclododecylamine, 2-hydroxyethylamine, 2-methoxyethylamine, 2-ethoxyethylamine, 3-hydroxypropylamine, 3-methoxypropylamine, 3-ethoxypropylamine, 3- (2-phenoxyethoxy) propylamine, 3-benzyloxypropylamine, 2- (N, N-dimethyl amino) ethylamine, 2- (N, N-diethylamino) ethylamine, 3 - (N, N-diethylamino) propylamine, 3- (N, N-diethylamino) propylamine, benzylamine, 2-phenylethylamine, 3-phenylpropylamine, aniline, 2-hydroxyaniline, 3-hydroxyaniline, 4-hydroxyaniline, o-anisidine, m-anisidine, p-anisidine, o-phenetidine, m-phenetidine, p-phenetidine, 2-chloroaniline, 3-chloroaniline, 3-nitroaniline, 4-nitroaniline, o-toluidine, m-toluidine, p-toluidine, 1,2-phenylenediamine, 1,3-phenylenediamine, 1,4-phenylenediamine, 2-trifluoromethylaniline, 3-trifluoromethylaniline, 4-trifluoromethylaniline, 2-ethylaniline, 3-ethylaniline, 4-ethylaniline, 2-aminopyridine, 3-aminopyridine, 4-aminopyridine, glycine methyl ester, Glycine ethyl ester, glycine propyl ester, glycine butyl ester, hydrazine, N, N-Di To name methylhydrazine or phenylhydrazine.

T⁴ are z. B. methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, pentyloxy, isopentyloxy, neopentyloxy or hexyloxy.

The rest T⁶ derives z. B. of methylactive compounds of the formula H₂T⁶ from. Such compounds obey the formula, for example

in the Z cyano, nitro, C₁-C₆-alkanoyl, benzoyl, C₁-C₄-alkylsulfonyl, Phenylsulfonyl, carboxyl, C₁-C₄ alkoxycarbonyl, carbamoyl or C₁-C₄- Mono- or dialkylcarbamoyl means, or the formula

Some particularly important connections are e.g. B .:

R³ radicals are, for example, methylamino, ethylamino, propylamino, isopropylamino, Butylamino, isobutylamino, sec-butylamino, pentylamino, Isopentylamino, neopentylamino, hexylamino, heptylamino, octylamino, Isooctylamino, 2-ethylhexylamino, nonylamino, isononylamino, decylamino, Isodecylamino, undecylamino, dodecylamino, tridecylamino, isotridecylamino, Tetradecylamino, pentadecylamino, hexadecylamino, heptadecylamino, Octadecylamino, nonadecylamino, eicosylamino, (R) - (-) - 1-cyclohexylethylamino, (S) - (+) - 1-cyclohexylethylamino, 2-cyclohexylethylamino, 2-hydroxyethylamino, 2-methoxyethylamino, 2-ethoxyethylamino ,, 2-phenoxyethylamino, 2- (2'-hydroxyethoxy) ethylamino, 2- (2'-hydroxyethyl) aminoethylamino, 2-aminoethylamino, 2-dimethylaminoethylamino, 2-diethylaminoethylamino, 2-diisopropylaminoethylamino, 2- (piperazin-1-yl) ethylamino, 3-hydroxy-n- propylamino, 3-methoxy-n-propylamino, 3-ethoxy-n-propylamino, 3-isoprop oxy-n-propylamino, 3-phenoxy-n-propylamino, 3-benzyloxy-n-propylamino, 3- (2′-methoxy) -n-propylamino, 3- (2′-ethoxyethoxy) -n-propylamino, 3- (2'-phenoxyethoxy) -n-propylamino, 3-amino-n-propylamino, 3-dimethyl amino-n-propylamino, 3-diethylamino-n-propylamino, 3-di-n-propylamino-n- propylamino, 3-diisopropylamino-n-propylamino, 3-di-n-butylamino-n- propylamino, 3-morpholin-1-yl-n-propylamino, 4-hydroxy-n-butylamino, 4-amino-n-butylamino, 5-hydroxy-n-pentylamino, 5-amino-n-pentylamino, 6-hydroxy-n-hexylamino, 6-amino-n-hexylamino, 7-hydroxy-n-heptylamino, 7-amino-n-heptylamino, 8-hydroxy-n-octylamino, 8-amino-n-octylamino, 9-hydroxy-n-nonylamino, 9-amino-n-nonylamino, 10-hydroxy-n-decylamino, 10-amino-n-decylamino, 11-amino-n-undecylamino, 4-diethylamino-1-methyl- n-butylamino, 2-hydroxy-n-propylamino, 1-ethyl-2-hydroxylethylamino, 2-hydroxy-1,1-dimethylethylamino, 1,1-bis (hydroxymethyl) ethylamino, 1-ethyl-2-hydroxyethylamino, 2-hydroxycarbonylethylamino, 3-hydroxy carbonyl-n-propylamino, 4-hydroxycarbonyl-n-butylamino, 5-hydroxycarbonyl n-pentylamino, 10-hydroxycarbonyl-n-decylamino, phenylamino, o-methyl phenylamino, m-methylphenylamino, p-methylphenylamino, o-ethylphenylamino,  m-ethylphenylamino, p-ethylphenylamino, o-trifluoromethylphenylamino, m-trifluoromethylphenylamino, p-trifluoromethylphenylamino, o-hydroxyphenylamino, m-hydroxyphenylamino, p-hydroxyphenylamino, o-methoxyphenylamino, m-methoxyphenylamino, p-methoxyphenylamino, o-ethoxyphenylamino, m-ethoxy phenylamino, p-ethoxyphenylamino, o-chlorophenylamino, m-chlorophenylamino, p-chlorophenylamino, o-fluorophenylamino, m-fluorophenylamino, p-fluorophenylamino, o-bromophenylamino, m-bromophenylamino, o-bromophenylamino, o-iodine phenylamino, m-iodophenylamino, p-iodophenylamino, o-aminophenylamino, m-aminophenylamino, p-aminophenylamino, p-acetylaminophenylamino, o-hydroxymethylphenylamino, m-hydroxymethylphenylamino, p-hydroxymethylphenylamino, o-hydroxycarbonylphenylamino, m-hydroxycarbonylphenylamino, p-hydroxycarbonylphenylamino, o-aminocarbonylphenylamino, m-hydroxy carbonylphenylamino, p-hydroxycarboylphenylamino, o-cyanophenylamino, m-cyanophenylamino, p-cyanophenylamino, 2,6-dimethylphenylamino, 3,5-dimethylphenylamino, 2-hydroxy-5-methylphenylamino, 2-hydroxy-4- methylphenylamino, 4-hydroxy-2-methylphenylamino, 2-hydroxy-5-chlorophenylamino, Imidazol-1-yl, pyrazol-1-yl, pyrid-2-ylamino, pyrid-3-ylamino, Pyrid-4-ylamino, pyrid-3-ylmethylamino, fur-2-ylmethylamino, thienylamino, Benzylamino, o-methoxybenzylamino, p-methoxybenzylamino, p-fluorobenzylamino, o-chlorobenzylamino, p-chlorobenzylamino, 3,4-dimethoxybenzylamino, 2-phenylethylamino, (+/-) - α-methylbenzylamino, (+) - α-methylbenzylamino, (-) - α-methylbenzylamino, 3-phenyl-n-propylamino, α-methyl-γ-phenyl-n- propylamino, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclo hexylamino, cycloheptylamino, cyclooctylamino, cyclononylamino, cyclo decylamino, cyclododecylamino, allylamino, propargylamino, methallylamino, Dimethylamino, diethylamino, di-n-propylamino, di-n-butylamino, diiso propylamino, diisobutylamino, di-sec-butylamino, di-n-pentylamino, Diisopentylamino, di-n-hexylamino, di (α-ethyl-n-hexyl) amino, di-n- octylamino, diallylamino, dicyclohexylamino, N-methyl-n-butylamino, N-methylcyclohexylamino, N-ethylcyclohexylamino, N-methylethanolamino, N-ethyl-1,3-dimethyl-n-propylamino, N-ethylethanolamino, N-ethyl-2-hydroxy-n-propylamino, N-tert-butylethanolamino, N-methylphenylamino, N-ethylphenylamino, N-n-propylphenylamino, N-iso propylphenylamino, N-n-butylphenylamino, dibenzylamino, N-methylbenzylamino, N-ethylbenzylamino, N-isopropylbenzylamino, N-tert-butylbenzylamino, N- (2-hydroxyethyl) benzylamino, N-phenylbenzylamino, N-benzyl-2- phenylethylamino, pyrrolidino, piperidino, hexamethyleneimino, morpholino, N-methylpiperazino, piperazino, N-ethylpiperazino or thiomorpholino.

Preferred diaminothiazoles of the formula I are those in which
R¹ and R² are each hydrogen or together the rest

wherein T¹ is hydrogen, C₁-C₄ alkyl or phenyl and T² and T³ independently of one another for C₁-C₄-alkyl or phenyl, or together with the nitrogen atom connecting them for pyrrolidino, piperidino, Morpholino, thiomorpholino, piperazino, N- (C₁-C₄-alkyl) piperazino or Hexamethylenimino stand, mean and R³ and R⁴ each the above To have meaning.

Diaminothiazoles of the formula I in which R 1 and R 2 are particularly preferred each hydrogen or together the rest

mean, T¹ for hydrogen and T² and T³ independently stand for C₁-C₄-alkyl.

Also particularly preferred are diaminothiophenes of the formula I in which
R⁴ formyl, acetyl, propionyl, butyryl, benzoyl, cyano or a radical of the formula

means, wherein T⁵ is hydrogen, methyl, ethyl or phenyl and T⁴ and T⁶ each have the meaning given above.

Also particularly preferred are diaminothiophenes of the formula I in which R³ C₁-C₆ mono- or dialkylamino, allylamino, methallylamino, propargylamino, C₂-C₆ alkylamino by phenyl, hydroxy, phenoxy, amino or C₁-C₄ mono- or dialkylamino substituted or by an oxygen atom is interrupted, phenylamino, pyrrolidino, piperidino, morpholino, Piperazino or N- (C₁-C₄-alkyl) piperazino means.

Also particularly preferred are diaminothiazoles of the formula I in which R⁴ cyano, formyl or the rest

means, wherein Z is cyano, nitro or C₁-C₄ alkoxycarbonyl.  

Of particular importance are diaminothiazoles of the formula I in which R¹ and R² each represent hydrogen or together the radical = CH-N (CH₃) ₂.

Also to be mentioned in particular are diaminothiazoles of the formula I in which
R⁴ formyl, cyano or a radical of the formula

means, wherein T⁴ for hydroxy, methoxy, ethoxy or amino and T⁵ for Are hydrogen, methyl, ethyl or phenyl and T⁶ the above Has meaning.

Of particular note are diaminothiazoles of the formula I in which
R⁴ formyl, cyano or a radical of the formula

means, where T⁶ has the meaning given above.

Particularly noteworthy are diaminothiazoles of the formula Ia

or their tautomers, where
L¹ amino,
L² C₁-C₆-mono- or dialkylamino, allylamino, methallylamino, propargylamino, C₂-C₆-alkylamino which is substituted by phenyl, hydroxy, phenoxy, amino or C₁-C₄-mono- or dialkylamino or is interrupted by an oxygen atom, phenylamino, Pyrrolidino, piperidino, morpholino, piperazino or N- (C₁-C₄-alkyl) piperazino and
L³ cyano, formyl or the rest

mean, wherein Z is cyano, nitro or C₁-C₄ alkoxycarbonyl.  

The diaminothiazoles of formula I according to the invention can, for. B. by Implementation of aminothiophenes of the formula II

in which R¹, R² and R⁴ each have the meaning given above and Hal represents chlorine or bromine, with an amino compound of the formula III

R³-H (III)

in which R³ has the meaning given above, can be obtained.

To do this, e.g. B. the aminothiazole II with the amino compound III in an inert solvent (e.g. N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidinone, hexamethylphosphoric trisamide, 1,3-dimethyl imidazolidin-2-one, 1,3-dimethylhexahydropyrimidin-2-one, 1,2-diethoxyethane, Benzene, toluene, xylene, methylene chloride, chloroform, methanol, ethanol, Propanol, isopropanol, butanol or isobutanol) at a temperature of -10 to + 150 ° C around. The molar ratio II: III is usually 1: 2 to 1:10.

The aminothiazoles of the formula II are known per se and, for. B. in the US-A-43 95 544 described or can be analogous to those listed there Methods can be obtained.

The new diaminothiazoles are valuable intermediates for synthesis of dyes, crop protection agents or pharmaceuticals. In particular they serve as a diazo component (R¹, R² = H) for the production of Azo dyes.

The following examples are intended to explain the invention in more detail.

example 1

8.1 g of 2-amino-4-chloro-5-formylthiazole were dissolved in 40 ml of N, N-dimethylformamide solved. For this purpose, 9.9 ml of piperidine were added dropwise at 35 to 40 ° C. The The reaction mixture was stirred for 4 hours at room temperature and then poured onto 150 ml of ice water. The precipitate was suctioned off, washed with water and under reduced pressure at 50 ° C dried. 6.3 g (60% of theory) of the compound of the formula were obtained

melting point 160 ° C (decomposition). The NMR, IR, UV and mass spectra as well as the elementary analysis with the given structural formula in Harmony.

Example 2

8 g of 2-amino-4-chloro-5-cyanothiazole were dissolved in 50 ml of N, N-dimethylformamide solved. For this purpose, 7.9 ml of 70% by weight aqueous ethylamine at 35 ° C. Solution added dropwise. The reaction mixture was at room temperature for 1 hour touched. Then another 1 ml of 70% by weight aqueous ethylamine was Solution added. After stirring for a further 0.5 hours at room temperature the reaction mixture was poured onto 400 ml of ice water and 5 ml of hydrochloric acid (M 100) given. The precipitate was filtered off, washed with water and dried at 50 ° C under reduced pressure. 4.0 g (48% d. Th.) Of the compound of the formula

melting point 171-174 ° C. The NMR, IR, UV and mass spectra as well the data of the elementary analysis stand with the structural formula given above in line.

The compounds listed in the following table can be prepared in an analogous manner.

Claims (3)

1. Diaminothiazoles of the formula I. or their tautomers, where
R¹ and R² are each hydrogen or together a radical of the formula wherein T¹ for hydrogen, C₁-C₆-alkyl or phenyl and T² and T³ are the same or different and independently of each other for C₁-C₆-alkyl, C₅-C₇-cycloalkyl or phenyl or T² and T³ together with the nitrogen atom connecting them for one 5- to 7-membered saturated heterocyclic radical which optionally contains further heteroatoms,
R³ C₁-C₂₀-mono- or dialkylamino, in which the alkyl chain is optionally substituted and / or interrupted by one or more oxygen atoms, C₃-C₈-cycloalkylamino, adamantylamino, C₂-C₁₂-mono- or dialkenylamino, C₃-C₁₂-alkynylamino, N. - (C₁-C₅-alkyl) -N-phenylamino, pyrrolidino, piperidino, morpholino, thiomorpholino, piperazino, N (- (C₁-C₄-alkyl) piperazino, hexamethyleneimino, imidazol-1-yl, pyrazol-1-yl, if appropriate substituted phenylamino, pyridylamino, thienylamino, hydrazino, C₁-C₄ mono- or dialkylhydrazino or phenylhydrazino and
R⁴ C₁-C₆ alkanoyl, benzoyl, cyano or a radical of the formula mean in which T⁴ is hydroxy, C₁-C₆-alkoxy, amino or the radical R³, T⁵ is hydrogen, C₁-C₆-alkyl or phenyl and T⁶ is the radical of a methylene-active compound, hydroxyimino or the radical NX, in which X is The meaning of C₁-C₂₀-alkyl which is optionally substituted and / or interrupted by one or more oxygen atoms, optionally substituted C₃-C₆-alkenyl, optionally substituted C₃-C₆-alkynyl, optionally substituted C₃-C₁₂-cycloalkyl, optionally substituted phenyl, Possesses pyridyl, C₁-C₄-alkoxycarbonylmethyl, amino, C₁-C₄-dialkylamino or phenylamino,
with the proviso that when R³ is piperidino or morpholino and R⁴ is cyano, R¹ and kR² are not simultaneously hydrogen. 2. diaminothiazoles according to claim 1, characterized in that
R¹ and R² are each hydrogen or together the rest wherein T¹ for hydrogen, C₁-C₄-alkyl or phenyl and T² and T³ independently of one another for C₁-C₄-alkyl or phenyl, or together with the nitrogen atom connecting them for pyrrolidino, piperidino, morpholino, thiomorpholino, piperazino, N- (C₁- C₄-alkyl) piperazino or hexamethyleneimino, mean and R³ and R⁴ each have the meaning given in claim 1. 3. A process for the preparation of diaminothiazoles according to claim 1, characterized in that aminothiazoles of the formula II in which R¹, R² and R⁴ each have the meaning given in Claim 1 and Hal represents chlorine or bromine, with an amino compound of the formula IIIR³-H (III) in which R³ has the meaning given in Claim 1.