DE2150686A1 - 6-amino-uracil-5-carboxylic acid thioamides - inters for dyestuffs and pharmaceuticals - Google Patents

6-amino-uracil-5-carboxylic acid thioamides - inters for dyestuffs and pharmaceuticals

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DE2150686A1
DE2150686A1 DE19712150686 DE2150686A DE2150686A1 DE 2150686 A1 DE2150686 A1 DE 2150686A1 DE 19712150686 DE19712150686 DE 19712150686 DE 2150686 A DE2150686 A DE 2150686A DE 2150686 A1 DE2150686 A1 DE 2150686A1
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uracil
amino
isothiocyanate
methyl
carbon atoms
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Heinz Dr Eilingsfeld
Rolf Dr Niess
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BASF SE
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BASF SE
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52—Two oxygen atoms
    • C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
    • C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/557—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. orotic acid

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Novel cpds. are of formula (I): (where R' is H, opt. substd. alkyl, cycloalkyl or aralkyl; R2 is as R1 or phenyl or opt. substd. heterocyclyl; R3 and R4 = as R1 or aryl; or NR3R4 is a heterocyclic radical; R5 is sulphonyl or acyl). (I) are inters. for dyestuffs and pharmaceuticals.

Description

6-Amino-uracil-5-carbonsäure-thioamide Die Erfindung betrifft Verbindungen der allgemeinen Formel I in der R1 Wasserstoff, gegebenenfalls substituiertes Alkyl, Cycloalkyl oder Aralkyl, R2 unabhängig von R1 Wasserstoff, gegebenenfalls substituiertes Alkyl, Cycloalkyl, Aralkyl, Phenyl oder einen gegebenenfalls substituierten heterocyclischen Rest, R5 Wasserstoff, gegebenenfalls substituiertes Alkyl, Cycloalkyl, Aralkyl oder Aryl, R4 Wasserstoff, gegebenenfalls substituiertes Alky, Cycloalkyl, Aralkyl oder Aryl, R3 und R4 zuxammen mit dem Stickstoff einen heterocyclischen Rest und R5 einen Sulfonyl- oder Acylrest bedeuten.6-Amino-uracil-5-carboxylic acid thioamides The invention relates to compounds of the general formula I. in which R1 is hydrogen, optionally substituted alkyl, cycloalkyl or aralkyl, R2 independently of R1 is hydrogen, optionally substituted alkyl, cycloalkyl, aralkyl, phenyl or an optionally substituted heterocyclic radical, R5 is hydrogen, optionally substituted alkyl, cycloalkyl, aralkyl or aryl, R4 is hydrogen , optionally substituted alkyl, cycloalkyl, aralkyl or aryl, R3 and R4 together with the nitrogen denote a heterocyclic radical and R5 denote a sulfonyl or acyl radical.

Vorzugsweise sind für R1 und R2 Alkylreste mit 1 bis 4 C-Atomen, durch Alkoxy mit 1 bis 4 C-Atomen, Dialkylamino mit insgesamt 2 bis 8 C-Atomen oder Alkanoyloxy mit 2 bis 4 C-Atomen substituierte Alkylreste mit 2 oder 3 C-Atomen, gegebenenfalls durch Methyl substituiertes Cyclohexyl und für R2 außerdem gegebenenfalls durch Chlor, Brom, Methoxy, Äthoxy, Methyl oder Xthyl substituiertes Phenyl zu nennen.Alkyl radicals with 1 to 4 carbon atoms are preferably through for R1 and R2 Alkoxy with 1 to 4 carbon atoms, dialkylamino with a total of 2 to 8 carbon atoms or alkanoyloxy with 2 to 4 carbon atoms substituted alkyl radicals with 2 or 3 carbon atoms, optionally methyl-substituted cyclohexyl and, for R2, also optionally through To mention chlorine, bromine, methoxy, ethoxy, methyl or xthyl-substituted phenyl.

Im einzelnen seien für R1 und R2 beispielsweise genannt: Methyl, Athyl, n- oder i-Propyl oder -Butyl, Allyl, Methoxyäthyl, -propyl oder -butyl, Xthoxyäthyl, -propyl oder -butyl, Butoxyäthyl, -propyl oder -butyl, Dimethylamino-, Diäthyl-, Dipropyl-, Dibutyl-, N-Methyl-N-butyl-aminoäthyl oder -aminopropyl, Acetoxy-, Propionyloxy- oder Butyryloxyäthyl oder -propyl, Cyclohexyl, Methylcyclohexyl, Benzyl oder Phenyläthyl und für R2 Chlorphenyl, Dichlor-, Brom-, Methoxy-, Athoxy-, Methyl- oder Dimethylphenyl.Examples include for R1 and R2: methyl, ethyl, n- or i-propyl or -butyl, allyl, methoxyethyl, -propyl or -butyl, xthoxyethyl, -propyl or -butyl, Butoxyethyl, propyl or butyl, dimethylamino, Diethyl, dipropyl, dibutyl, N-methyl-N-butyl-aminoethyl or aminopropyl, acetoxy, Propionyloxy or butyryloxyethyl or propyl, cyclohexyl, methylcyclohexyl, benzyl or phenylethyl and for R2 chlorophenyl, dichloro, bromine, methoxy, ethoxy, methyl or dimethylphenyl.

Heterocyclische Reste R leiten sich z. B. von Furan oder Thiophen ab. Im einzelnen seien z. B. Thienyl oder Furyl genannt.Heterocyclic radicals R derive z. B. of furan or thiophene away. In detail z. B. called thienyl or furyl.

Reste R3 und R4 sind neben Wasserstoff beispielsweise Alkyl mit 1 bis 4 C-Atomen, durch Alkoxy, Cyan, Alkanoyloxy oder Dialkylamino substituiertes Alkyl, Cyclohexyl, Benzyl, Phenyläthyl, Phenyl oder durch Chlor, Methyl, Methoxy oder Äthoxy substituiertes Phenyl.R3 and R4 radicals are, in addition to hydrogen, for example alkyl with 1 up to 4 carbon atoms, substituted by alkoxy, cyano, alkanoyloxy or dialkylamino Alkyl, cyclohexyl, benzyl, phenylethyl, phenyl or by chlorine, methyl, methoxy or ethoxy substituted phenyl.

Im einzelnen seien beispielsweise noch genannt: Methyl, Athyl, n- oder iso-Propyl oder -Butyl, Methoxyäthyl, -propyl oder -butyl, {thoxyäthyl, -propyl oder -butyl, Butoxyäthyl, -propyl oder -butyl, Cyanäthyl, Acetoxyäthyl, Propionyl-oxy-äthyl, Dimethylaminopropyl oder -butyl oder Dibutylaminopropyl.In detail, for example, are also mentioned: methyl, ethyl, n- or iso-propyl or -butyl, methoxyethyl, -propyl or -butyl, {thoxyethyl, -propyl or -butyl, butoxyethyl, -propyl or -butyl, cyanoethyl, acetoxyethyl, propionyl-oxy-ethyl, Dimethylaminopropyl or butyl or dibutylaminopropyl.

4 Zusammen mit dem Stickstoff bedeuten R3 und R4 beispielsweise den Rest des Pyrrolidins, Piperidins, Morpholins oder N-Methylpiperazins.4 Together with nitrogen, R3 and R4 mean, for example, the Remainder of the pyrrolidine, piperidine, morpholine or N-methylpiperazine.

Als Sulronylreste R5 sind Alkyl-, Aryl-, Cycloalkyl-, Aralkyl-oder Heteroarylsulfonylreste zu nennen.As sulronyl radicals R5 are alkyl, aryl, cycloalkyl, aralkyl or Mentioning heteroarylsulfonyl radicals.

Einzelreste sind z. B.: Methylsulfonyl, Äthyl-, Propyl-, Butl-, Cyclohexyl-, Benzyl-, PhenylSthyl-, Phenyl-, Chlorphenyl-, Dichlorphenyl-, Methylphenyl-, Dimethylphenyl- oder Thienylsulfonyl Acylreste R5 sind beispielsweise Alkanoylgruppen, wie Acetyl, Propionyl, Butyryl, Caproyl, Hexanoyl, Capryloyl, ß-Athylhexanoyl, Chloracetyl, Bromacetyl, -Chlorpropionyl, - - Chlorpropionyl, /-Chlor-n-butyryl oder bBromisovaleroyl, Aralkanoylreste, wie Phenylacetyl, Tolylacetyl, Methoxyphenylacetyl, Chlorphenylacetyl oder Dichlorphenylacetyl, Alkoxy- oder Aroxycarbonylreste, wie Methoxycarbonyl, Äthoxycarbonyl, Propoxy-, Butoxy- oder Phenoxycarbonyl, Aroylreste, wie Benzoyl, durch Chlor, Brom, Nitro, Methoxy, Athoxy oder Methyl substituiertes Benzoyl, Naphthoyl, Phenanthronyl oder Cinnamoyl, oder heterocyclische Reste wie Furoyl oder Thienyl Technisch von besonderer Bedeutung sind Verbindungen der Formel Ia in der A Wasserstoff, Alkyl mit 1 bis 4 C-Atomen oder Alkoxyalkyl mit insgesamt 3 bis 8 C-Atomen, AI und A2 Wasserstoff oder Alkyl mit 1 bis 4 C-Atomen und A3 Alkylsulfonyl mit 1 bis 4 C-Atomen, Arylsulfonyl, Alkoxycarbonyl mit 2 bis 5 C-Atomen, Phenoxycarbonyl oder Aroyl bedeuten.Individual residues are z. E.g .: methylsulfonyl, ethyl, propyl, butl, cyclohexyl, benzyl, phenyl-ethyl, phenyl, chlorophenyl, dichlorophenyl, methylphenyl, dimethylphenyl or thienylsulfonyl acyl groups R5 are, for example, alkanoyl groups such as acetyl, propionyl, Butyryl, caproyl, hexanoyl, capryloyl, ß-ethylhexanoyl, chloroacetyl, bromoacetyl, -chloropropionyl, - - chloropropionyl, / -chloro-n-butyryl or b-bromisovaleroyl, aralkanoyl radicals, such as phenylacetyl, tolylacetyl, or alkoxyphenoxyphenylacetyl, phenylacetyl, tolylacetyl, or methoxyphenoxyphenylacetyl, alkoxyphenoxyphenylacetyl, or alkoxyphenoxyphenylacetyl, chloroacetyl, bromoacetyl, chloropropionyl or alkoxyphenoxyphenylacetyl such as methoxycarbonyl, ethoxycarbonyl, propoxy, butoxy or phenoxycarbonyl, aroyl radicals such as benzoyl, benzoyl substituted by chlorine, bromine, nitro, methoxy, ethoxy or methyl, naphthoyl, phenanthronyl or cinnamoyl, or heterocyclic radicals such as furoyl or thienyl Technically of particular The meaning is given to compounds of the formula Ia in which A is hydrogen, alkyl with 1 to 4 carbon atoms or alkoxyalkyl with a total of 3 to 8 carbon atoms, AI and A2 are hydrogen or alkyl with 1 to 4 carbon atoms and A3 alkylsulfonyl with 1 to 4 carbon atoms, arylsulfonyl, Alkoxycarbonyl with 2 to 5 carbon atoms, phenoxycarbonyl or aroyl.

Zur Herstellung der 6-Aminouracil-5-carbonsäurethioamide kann man ein 6-Amino-uracil der allgemeinen Formel II in der 4 R1, R2, P und R4 die angegebene Bedeutung haben, mit Isothiocyanaten der allgemeinen Formel III R5-N=C=S III, umsetzen, wobei R5 die angegebene Bedeutung hat.To prepare the 6-aminouracil-5-carboxylic acid thioamides, a 6-aminouracil of the general formula II can be used in which 4 R1, R2, P and R4 have the meaning given, react with isothiocyanates of the general formula III R5-N = C = S III, where R5 has the meaning given.

Verbindungen der Formel II sind beispielsweise: 6-Aminouractl 1-Methyl-6-amino-uracil 1-thyl-6-amino-uracil 1-n-Propyl-6-amino-uracil 1-Allyl-6-amino-uracil 1-n-Butyl-6-amino-uracil l-Isobutyl-6-amino-uracil 1-Benzyl-6-amino-uracil 1-Methoxyäthyl-6-amino-uracil 1-Athoxyäthyl-6-amlno-uraci1 1-Isopropoxyäthyl-6-amino-uracil 1-γ-Methoxypropyl-6-amino-uracil 1-γ-Äthoxypropyl-6-amino-uracil 1-t-Propoxypropyl-6-amino- uracil 1-γ-Isopropoxypropyl-6-amino-uracil 1-γ-Butoxypropyl-6-amino-uracil 1-B-Dimethylaminoäthyl-6-amino-uracil 1 Phenyl-6-amino- uracil 1-p-Chlorphenyl-6-amino-uracil 1-p-Tolyl-6-amino-uracil 1, 3-Dimethyl-6-amino uracil 1,3-Diäthyl-6-amino-uracil 1,3-Di-1-propyl-6-amino-uracil 1,3-Di-n-propyl-6-amino-uracil 1,3-Diallyl-6-amino-uracil 1,3-Di-n-butyl-6-amino-uracil 1,3-Dibenzyl-6-amino-uracil 1,3-Di-methoxyäthyl-6-amino-uracil 1,3-Di-äthoxyäthyl-6-amino-uracil 1,3-Di-isopropoxyäthyl-6-amino uracil 1,3-Di-γ-methoxypropyl-6-amino-uracil 1,3-Di-γ-äthoxypropyl-6-amino-uracil 1,3-Di-γ-isopropoxypropyl-6-amino-uracil 1,3-Di-γ-butoxypropyl-6-amino-uracil 1-Äthyl-3-methyl-6-amino-uracil 1-n-Propyl-3-methyl-6-amino-uracil l-Isopropyl-3-methyl-6-amino-uracil 1-n-Butyl-3-methyl-6-amino-uracil 1-Isobutyl-3-methyl-6-amino-uracil 1-Allyl-3-methyl-6-amino-uracil 1-Cyclohexyl-3-methyl-6-amino-uracil 1-p-Chlorphenyl-3-methyl-6-amino-uracil 1-Phenyl-3-methyl-6-amino-uracil 1-Furfuryl-3-methyl-6-amino-uracil 1-Methyl-3-äthyl-6-amino-uracil 1-n-Propyl-3-äthyl-6-amino-uracil 1-Isopropyl-3-äthyl-6-amino-uracil 1-Allyl-3-äthyl-6-amino-uracil 1-n-Butyl-3-äthyl-6-amino-uracil 1-n-Hexyl-3-äthyl-6-amino-uracil 1-Cyclohexyl-3-äthyl-6-amino-uracil 1-γ-Phenylpropyl-3-äthyl-6-amino-uracil 1-Methyl-3-n-propyl-6-amino-uracil 1-Äthyl-3-n-propyl-6-amino-uracil 1-Allyl-3-n-propyl-6-amino-uracil 1-Äthyl-3-allyl-6-amino-uracil 1-Isobutyl-3-allyl-6-amino-uracil 1-Phenyl-3-allyl-6-amino-uracil 1-Benzyl-3-allyl-6-amino-uracil 1-Äthyl-3-n-butyl-6-amino-uracil 1-Allyl-3-n-butyl-6-amino-uracil 1-Methoxyäthyl-3-methyl-6-amino-uracil 1-Äthoxyäthyl-3-methyl-6-amino-uracil 1-Isopropoxyäthyl-3-methyl-6-amino-uracil 1-γ-Methoxypropyl-3-methyl-6-amino-uracil 1-γ-Äthoxypropyl-3-methyl-6-amino-uracil 1-γ-Isopropoxypropyl-3-methyl-6-amino-uracil 1-γ-Butoxypropyl-3-methyl-6-amino-uracil 1-Phenyl-3-γ-methoxypropyl-6-amino-uracil 1,3-Dimethyl-6-methylamino-uracil 1,3-Diäthyl-6-methylamino-uracil 1,3-Di-n-Propyl-6-methylamino-uracil 1,3-Di-i-Propyl-6-methylamino-uracil 1,3-Di-n-Butyl-6-methylamino-uracil 1,3-Di-i-Butyl-6-methylamino-uracil 1,3-Di-Benzyl-6-methylamino-uracil 1,3-Dimethyl-6-äthylamino-uracil 1,3-Dimethyl-6-benzylamino-uracil 1,3-Dimethyl-6-butylamino-uracil 1,3-Dimethyl-6-(γ-methoxy)-propylamino-uracil 1,3-Dimethyl-6-(γ-äthoxy)-propylamino-uracil 1,3-Dimethyl-6-(γ-butoxy)-propylamino-uracil 1,3-Dimethyl-6-methoxy-äthylamino-uracil 1,3-Dimethyl-6-pyrrolidono-uracil 1,3-Dimethyl-6-piperidino-uracil 1,3-Dimethyl-6-dimethylamino-uracil 1,3-Dimethyl-6-phenylamino-uracil Die Herstellung dieser Verbindungen erfolgt nach bekannten Verfahren, siehe z. B. J. Org. Chem. 16, 1879 bis 1890 (1951).Compounds of the formula II are, for example: 6-aminouractl 1-methyl-6-aminouracil 1-thyl-6-amino-uracil 1-n-propyl-6-amino-uracil 1-allyl-6-amino-uracil 1-n-butyl-6-amino-uracil l-isobutyl-6-amino-uracil 1-benzyl-6-amino-uracil 1-methoxyethyl-6-amino-uracil 1-ethoxyethyl-6-amino-uracil 1-isopropoxyethyl-6-amino-uracil 1-γ-methoxypropyl-6-amino-uracil 1-γ-ethoxypropyl-6-amino-uracil 1-t-propoxypropyl-6-amino-uracil 1-γ-isopropoxypropyl-6-amino-uracil 1-γ-butoxypropyl-6-amino-uracil 1-B-dimethylaminoethyl-6-amino-uracil 1 phenyl-6-amino- uracil 1-p-chlorophenyl-6-amino-uracil 1-p-tolyl-6-amino-uracil 1, 3-dimethyl-6-amino uracil 1,3-diethyl-6-amino-uracil 1,3-di-1-propyl-6-amino-uracil 1,3-di-n-propyl-6-amino-uracil 1,3-diallyl-6-amino-uracil 1,3-di-n-butyl-6-amino-uracil 1,3-dibenzyl-6-amino-uracil 1,3-di-methoxyethyl-6-aminouracil 1,3-di-ethoxyethyl-6-aminouracil 1,3-di-isopropoxyethyl-6-amino uracil 1,3-di-γ-methoxypropyl-6-amino-uracil 1,3-di-γ-ethoxypropyl-6-amino-uracil 1,3-di-γ-isopropoxypropyl-6-aminouracil 1,3-di-γ-butoxypropyl-6-aminouracil 1-ethyl-3-methyl-6-amino-uracil 1-n-propyl-3-methyl-6-amino-uracil 1-isopropyl-3-methyl-6-amino-uracil 1-n-Butyl-3-methyl-6-amino-uracil 1-isobutyl-3-methyl-6-amino-uracil 1-allyl-3-methyl-6-amino-uracil 1-Cyclohexyl-3-methyl-6-aminouracil 1-p-chlorophenyl-3-methyl-6-amino-uracil 1-phenyl-3-methyl-6-amino-uracil 1-furfuryl-3-methyl-6-amino-uracil 1-methyl-3-ethyl-6-amino-uracil 1-n-propyl-3-ethyl-6-amino-uracil 1-isopropyl-3-ethyl-6-amino-uracil 1-allyl-3-ethyl-6-amino-uracil 1-n-butyl-3-ethyl-6-amino-uracil 1-n-hexyl-3-ethyl-6-amino-uracil 1-Cyclohexyl-3-ethyl-6-amino-uracil 1-γ-phenylpropyl-3-ethyl-6-amino-uracil 1-methyl-3-n-propyl-6-amino-uracil 1-ethyl-3-n-propyl-6-amino-uracil 1-allyl-3-n-propyl-6-amino-uracil 1-ethyl-3-allyl-6-amino-uracil 1-isobutyl-3-allyl-6-amino-uracil 1-phenyl-3-allyl-6-amino-uracil 1-Benzyl-3-allyl-6-amino-uracil 1-ethyl-3-n-butyl-6-amino-uracil 1-allyl-3-n-butyl-6-amino-uracil 1-methoxyethyl-3-methyl-6-amino-uracil 1-ethoxyethyl-3-methyl-6-amino-uracil 1-isopropoxyethyl-3-methyl-6-amino-uracil 1-γ-methoxypropyl-3-methyl-6-amino-uracil 1-γ-ethoxypropyl-3-methyl-6-amino-uracil 1-γ-Isopropoxypropyl-3-methyl-6-amino-uracil 1-γ-Butoxypropyl-3-methyl-6-amino-uracil 1-phenyl-3-γ-methoxypropyl-6-aminouracil 1,3-dimethyl-6-methylamino-uracil 1,3-diethyl-6-methylamino-uracil 1,3-di-n-propyl-6-methylamino-uracil 1,3-di-i-propyl-6-methylamino-uracil 1,3-di-n-butyl-6-methylamino-uracil 1,3-di-i-butyl-6-methylamino-uracil 1,3-di-benzyl-6-methylamino-uracil 1,3-dimethyl-6-ethylamino-uracil 1,3-dimethyl-6-benzylamino-uracil 1,3-dimethyl-6-butylamino-uracil 1,3-dimethyl-6- (γ-methoxy) propylamino uracil 1,3-dimethyl-6- (γ-ethoxy) -propylamino-uracil 1,3-dimethyl-6- (γ-butoxy) -propylamino-uracil 1,3-dimethyl-6-methoxy-ethylamino-uracil 1,3-dimethyl-6-pyrrolidono-uracil 1,3-dimethyl-6-piperidino-uracil 1,3-dimethyl-6-dimethylamino-uracil 1,3-Dimethyl-6-phenylamino-uracil These compounds are prepared according to known method, see e.g. B. J. Org. Chem. 16, 1879-1890 (1951).

Als Isothiocyanate der Formel III können beispielsweise Sulfonylsenföle verwendet werden, als Beispiele seien angeführt: p-Toluolsulfonylsenföl Benzolsulfonylsenföl o-Toluolsulfonylsenföl o-Chlorbenzolsulfonylsenföl m-Chlorbenzolsulfonylsenföl p-Chlorbenzolsulfonylsenföl 3,4-Dichlorbenzolsulfonylsenföl Thiophen-2-sulronylsenföl Cyclohexansulfonylsenföl Methansulfonylsenfdl {thansulfonylsenföl Die Darstellung der Sulfonylsenföle erfolgt nach bekannten Verwahren, z. B. nach dem in der DAS 1 183 492 beschriebenen.Sulfonyl mustard oils, for example, can be used as isothiocyanates of the formula III may be used, examples being given: p-Toluenesulfonyl mustard oil Benzenesulfonyl mustard oil o-toluenesulfonyl mustard oil o-chlorobenzenesulfonyl mustard oil m-chlorobenzenesulfonyl mustard oil p-chlorobenzenesulfonyl mustard oil 3,4-dichlorobenzenesulfonyl mustard oil thiophene-2-sulronyl mustard oil cyclohexanesulfonyl mustard oil Methanesulfonylsenfdl {thanesulfonylsenföl The representation of the sulfonyl mustard takes place after known safekeeping, z. B. after that described in DAS 1 183 492.

Verbindungen der Formel III sind neben Sulfonylsenfölen auch Acylsenföle. Als Beispiele seien angerührt: Benzoylisothiocyanat 4-Methoxy-benzoyl-isothiocyanat p-Chlor-benzoyl-isothiocyanat pNitro-benzoyl-isothiocyanat m-Methoxy-benzoyl-isothiocyanat o-Methyl-benzoyl-isothiocyanat m-Methyl-benzoyl-isothiocyanat p-Methyl-benzoyl-isothiocyanat 3,5-Dimethyl-benzyl-isothiocyanat 2,6-Dichlorbenzoyl-isothiocyanat 2,4,6-Trimethyl-benzoyl-isothiocyanat 3,4,5Trimethoxy-benzoyl-isothiocyanat Thienoyl-isothiocyanat .E.-Naphtoyl-isothiocyanat ß-Naphtoyl-isothiocyanat 3 -Phenanthroyl-isothio cyanat Phenylacetyl-isothiocyanat m-Tolylacetyl-isothiocyanat p-Tolylacetyl-isothiocyanat m-Methoxyphenylacetyl-isothiocyanat p-Methoxyphenylacetyl-isothiocyanat p-Chlorphenylacetyl-isothiocyanat Carbmethoxy-isothiocyanat Carbäthoxy-isothiocyanat Carbbutoxy-isothiocyanat Phenoxycarbonyl-isothiocyanat Acetyl-isothiocyanat Propionyl-isothiocyanat Butyryl-isothiocyanat n-Caproyl-isothiocyanat n-Capryloyl-isothiocyanat Chloracetyl-isothiocyanat i--Chlorpropionyl-isothiocyanat ß-Chlorpropionyl-isothiocyanat 8-Brom-iso-butyryl-isothiocyanat ,?-Chlor-n-butyryl-isothiocyanat ti-Brom-iso-valeroyl-isothiocyanat Die Herstellung der Acylisothiocyanateerfolgt nach bekannten Verfahren, z. B. durch Umsetzung der entsprechenden Acylhalogenide mit Kalium-, Natrium-, Ammonium- oder Bleirhodanid in inerten Lösungsmitteln. Siehe z. B. Houben-Weyl, Methoden der organischen Chemie, 4. Aufl., Bd. 9, S. 879, G. Thieme, Stuttgart, 1955, oder J. Org. Chemistry 29, 2261 (1964) oder Pharmazeutische Zentralhalle 107, S. 277 (1968).In addition to sulfonyl mustard oils, compounds of the formula III are also acyl mustard oils. Examples include: benzoyl isothiocyanate 4-methoxy-benzoyl isothiocyanate p-chloro-benzoyl-isothiocyanate, p-nitro-benzoyl-isothiocyanate, m-methoxy-benzoyl-isothiocyanate o-methyl benzoyl isothiocyanate, m-methyl benzoyl isothiocyanate, p-methyl benzoyl isothiocyanate 3,5-dimethyl-benzyl-isothiocyanate 2,6-dichlorobenzoyl isothiocyanate 2,4,6-trimethyl-benzoyl-isothiocyanate 3,4,5-trimethoxy-benzoyl-isothiocyanate, thienoyl-isothiocyanate E. Naphtoyl isothiocyanate ß-naphtoyl isothiocyanate 3-phenanthroyl isothiocyanate Phenylacetyl isothiocyanate, m-tolylacetyl isothiocyanate, p-tolylacetyl isothiocyanate m-methoxyphenylacetyl isothiocyanate, p-methoxyphenylacetyl isothiocyanate, p-chlorophenylacetyl isothiocyanate Carbmethoxy-isothiocyanate carbethoxy-isothiocyanate carbbutoxy-isothiocyanate phenoxycarbonyl-isothiocyanate Acetyl isothiocyanate propionyl isothiocyanate butyryl isothiocyanate n-caproyl isothiocyanate n-capryloyl isothiocyanate chloroacetyl isothiocyanate i - chloropropionyl isothiocyanate ß-chloropropionyl isothiocyanate 8-bromo-iso-butyryl-isothiocyanate,? - chlorine-n-butyryl-isothiocyanate Ti-bromo-iso-valeroyl-isothiocyanate The preparation of the acyl isothiocyanates takes place according to known methods, e.g. B. by reacting the corresponding acyl halides with potassium, sodium, ammonium or lead rhodanide in inert solvents. Please refer z. B. Houben-Weyl, Methods of Organic Chemistry, 4th ed., Vol. 9, p. 879, G. Thieme, Stuttgart, 1955, or J. Org. Chemistry 29, 2261 (1964) or Pharmazeutische Zentralhalle 107, p. 277 (1968).

Wie die mesomeren Grenzformeln der Acylsenföle zeigen, haben sie zwei elektrophile Zentren, die reagieren können.Like the mesomeric limit formulas of acyl mustard oils show they have two electrophilic centers that can react.

Diese Reaktionsmöglichkeiten sind in der Literatur schon mehrfach beschrieben worden (vgl. dazu Chem. 3er. 104 1582 (1971)).These reaction possibilities are already several times in the literature (cf. Chem. 3er. 104 1582 (1971)).

Da weiterhin die 6-Aminouracile zwei Möglichkeiten für einen elektrophilen Angriff bieten, nämlich die 5-Stellung im Ring und die 6-Aminogruppe, war es überraschend und nicht vorhersehbar, daß bei der Umsetzung der Komponenten II und III ausschließlich die Verbindungen der Formel I erhalten werden.Since the 6-aminouracile continues to have two options for an electrophilic Offering attack, namely the 5-position in the ring and the 6-amino group, it was surprising and not foreseeable that in the implementation of components II and III exclusively the compounds of formula I are obtained.

Man führt die Umsetzung der 6-Aminouracile mit den Verbindungen der Formel III zweckmäßigerweise bei Temperaturen zwischen 10 und 2000, vorzugsweise 20 und 1000C, in einem gegenüber den Reaktionspartnernindifferenten Lösungs- oder Verdünnungsmittel durch. Als solche kommen beispielsweise 1,2-Dimethoxyäthan, Tetrahydrofuran, Dioxan, Formamid, Dimethylformamid, Dimethylacetamid, N-Methylpyrrolidin, Tetramethylensulfon, Benzol, Toluol, Chlorbenzol, Benzonitril oder Acetonitril in Betracht. Die Reaktion kann auch ohne Lösungsmittel unter Verwendung von überschüssiger Verbindung der Formel III ausgeführt werden.The implementation of the 6-aminouracils is carried out with the compounds of Formula III expediently at temperatures between 10 and 2000, preferably 20 and 1000C, in a solution or solution indifferent to the reactants Thinner. As such, for example, 1,2-dimethoxyethane, tetrahydrofuran, Dioxane, formamide, dimethylformamide, dimethylacetamide, N-methylpyrrolidine, tetramethylene sulfone, Benzene, toluene, chlorobenzene, benzonitrile or acetonitrile can be considered. The reaction can also be used without solvent using excess compound of the Formula III are run.

Im ersten Fall löst oder suspendiert man z. B. 0,1 Mol eines Aminouracils der Formel II bei Raumtemperatur im Lösungs- oder Verdünnungsmittel und gibt dann unter Rühren mindestens 0,1 Mol einer Verbindung der Formel III zu. vs tritt meist sofort eine exotherme Reaktion ein. Zur Vervollständigung der Umsetzung wird zusätzlich noch 1/2 bis 3, vorzugsweise 1 bis 2 Stunden auf 40 bis 800C erwärmt. Die häufig schwerlöslichen Umsetzungsprodukte kristallisieren beim Abkühlen meist aus, wenn nötig kann man einen Teil des Lösungsmittels unter vermindertem Druck abdestillieren oder die konzentrierte Lösung mit Äther, Petroläther, Cyclohexan oder auch Wasser versetzen, um die Abscheidung zu erzielen oder zu vervollständigen.In the first case one dissolves or suspends z. B. 0.1 mole of an aminouracil of the formula II at room temperature in a solvent or diluent and then gives with stirring at least 0.1 mol of a compound of the formula III. vs occurs mostly immediately an exothermic reaction occurs. To complete the implementation is additionally heated to 40 to 80 ° C. for a further 1/2 to 3, preferably 1 to 2, hours. Often poorly soluble reaction products usually crystallize out on cooling, if if necessary, part of the solvent can be distilled off under reduced pressure or the concentrated solution with ether, petroleum ether, cyclohexane or even water move to achieve or complete the deposition.

Die Aufarbeitung der Reaktionsmischungen erfolgt nach üblichen methoden, -. , durch Absaugen des Niedersehlages, Waschen mit z. B. Wasser, Alkoholen, Ather, Petroläther oder Cyclohexan und Trocknung unter. vermindertem Druck.The reaction mixtures are worked up by customary methods, -. , by vacuuming the debris, washing with z. B. water, Alcohols, ethers, petroleum ether or cyclohexane and drying under. diminished Pressure.

Auch bei der Ausführung der Reaktion mit überschüssiger Verbindung der Formel III, wobei man z. B. das 6-Aminouracil in die ungefähr 4- bis 8-fache molare Menge Senföl zweckmäßigerweise unter Rühren einträgt und nach dem Abklingen der exothermen Reaktion noch 1 bis 3 Stunden auf 40 bis 800C erwärmt, verwendet man bei der Isolierung des Reaktionsproduktes vorteilhaft ein dieses nicht lösendes Verdünnungsmittel, z. B. einen aliphatischen oder cycloaliphatischen Kohlenwasserstoff. Das Reaktionsprodukt fällt dann in einer leicht absaugbaren Form an; aus dem Filtrat läßt sich das nicht umgesetzte Isothiocyanat durch Fraktionierung gewinnen, Man erhält die Verbindungen der Formel I meist schon in sehr reiner Form. Sie lassen sich durch Umkristallisieren z. B. aus Alkoholen, Acetonitril, Benzol, Methylglykol oder Dimethylformamid weiter reinigen.Even when performing the reaction with excess compound of formula III, where one z. B. the 6-aminouracil in about 4 to 8 fold molar amount of mustard oil expediently enters with stirring and after subsiding the exothermic reaction heated to 40 to 80C for 1 to 3 hours, used when isolating the reaction product, it is advantageous to use a non-dissolving product Diluents, e.g. B. an aliphatic or cycloaliphatic hydrocarbon. The reaction product is then obtained in a form that can be easily removed by suction; from the filtrate the unreacted isothiocyanate can be obtained by fractionation, Man receives the compounds of formula I mostly in a very pure form. You let by recrystallization z. B. from alcohols, acetonitrile, benzene, methyl glycol or further purify dimethylformamide.

Die neuen Verbindungen sind wertvolle Zwischenprodukte zur Herstellung von Farbstoffen und Arzneimitteln.The new compounds are valuable intermediate products for production of dyes and medicines.

Die in den Beispielen angegebenen Teile sind Gewichtsteile; Prozentangaben beziehen sich auf Gewichtsprozente. Zur Herstellung der in der Tabelle durch Angabe der Substituenten charakterisierten Verbindungen der Formel I wurde folgende allgemeine Arbeitsweise gewählt: Zu 0,1 Mol 6-Amino-uracil, die in 30 bis 300 Teilen des in der Tabelle angegebenen Lösungsmittels gelöst oder suspendiert sind, werden 0,1 Mol Isothiocyanat bei Raumtemperatur unter Rühren zugegeben. Wegen der Empfindlichkeit der Isothiocyanate muß dabei unter Ausschluß von Feuchtigkeit gearbeitet werden. Reaktionstemperatur und Reaktionszeit sind der Tabelle zu entnehmen.The parts given in the examples are parts by weight; Percentages relate to percentages by weight. To produce the in the table by specifying of the substituents characterized compounds of the formula I was the following general Method of operation chosen: To 0.1 mol of 6-amino-uracil, which is contained in 30 to 300 parts of the in the solvent indicated in the table are dissolved or suspended, are 0.1 Mol isothiocyanate added at room temperature with stirring. Because of the sensitivity the isothiocyanates must be worked with exclusion of moisture. The table shows the reaction temperature and reaction time.

Der Ablauf der Reaktion läßt sich chromatographisch verfolgen.The course of the reaction can be followed by chromatography.

Die Aminouracilthioamide sind meist schwerlöslich und kristallisieren während der Reaktion oder beim Abkühlen der Lösung aus.The aminouracilthioamides are usually sparingly soluble and crystallize during the reaction or when the solution cools off.

Die Niederschläge werden abgesaugt, mit Methanol oder Ather ausgewaschen und unter vermindertem Druck bei 500C getrocknet. Lösliche Verbindungen werden entweder durch Zugabe von Wasser oder äther zur abgekühlten Reaktionslösung ausgefällt oder man destilliert das Lösungsmittel unter vermindertem Druck ab und verrührt den Rückstand mit Ather, wobei das Reaktionsprodukt auskristallisiert.The precipitates are filtered off with suction and washed out with methanol or ether and dried under reduced pressure at 50.degree. Soluble links are added either by adding water or ether to the cooled reaction solution precipitated or the solvent is distilled off under reduced pressure and stir the residue with ether, the reaction product crystallizing out.

Die rohen Umsetzungsprodukte sind meist sehr rein; für analytische Zwecke werden sie aus den angegebenen Lösungsmittel umkristallisiert.The raw reaction products are usually very pure; for analytical Purpose they are recrystallized from the specified solvent.

Nach dieser allgemeinen Vorschrift wurden die in der folgenden Tabelle aufgeführten 6-Amino-uracil-5-carbönsäurethioamide hergestellt. @@spiol-Nr. R¹ R² R³ R4 R5 Lösungs- Reaktions- Reaktions- Ausbeute Fp. mittel zeit temperatur (h) (°C) (%) (°C) 1 H H H H CO-OC2H5 NMP 2 140 81 >360 2 H H H H CO-C6H5 NMP 2 140 58,5 >360 3 H CH3 H H SO2-C6H4-CH3 (P) CH3CN 1 80 87 245-255 4 H CH3 H H SO2-CH3 H3CCN 1 60 85 308-312 5 H C2H5 H H SO2-C6H4-CH3 (P) H3CCN 16 25 81,5 244-246 6 H C2H5 H H SO2-C6H4-CH3 (P) H3CCN 1 80 73,6 240-248 7 H C2H5 H H SO2-CH3 H3CCN 1 70 92 268-270 8 H CH2-CH=CH2 H H SO2-C6H4-CH3 (P) H3CCN 16 25 92 223-224 9 H CH2-CH=CH2 H H SO2-C6H4-CH3 (P) H3CCN 1 80 94 226-228 10 H CH2-CH=CH2 H H SO2-CH3 H3CCN 4 25 98 256-260 11 H CH2-CH=CH2 H H SO2-CH3 H3CCN 1 70 94 250-260 12 H CH2-C6H5 H H CO-C6H4-NO2 (P) H3CCN 2 40 68,5 >320 13 H CH2-C6H5 H H SO2-C6H4-CH3 (P) H3CCN 1 80 86 234-236 Beispiel-Nr. R¹ R² R³ R4 R5 Lösungs- Reaktions- Reaktions- Ausbeute Fp. mittel zeit temperatur (h) (°C) (%) (°C) 14 H CH2-C6H5 H H SO2-CH3 H3CCN 4 25 92 243-245 15 H CH2-C6H5 H H SO2-CH3 H3CCN 1 70 89 240-243 16 H C6H5 H H CO-OC2H5 DMF 2 60 81,5 315-318 17 H C6H5 H H SO2-C6H4-CH3 (P) DMF 2 60 66 236-240 18 H C6H5 H H CO2-C6H4-NO2 (P) DMF 4 40 59 >300 19 CH3 CH3 H H CO-OC2H5 DMF 2 100 75 256-258 20 CH3 CH3 H H CO-OC2H5 CH3CN 2 80 89,5 256-258 21 CH3 CH3 H H CO-OC2H5 THF 2 65 67 254-256 22 CH3 CH3 H H CO-C6H5-Cl (P) DMF 4 25 77 23 CH3 CH3 H H SO2-C6H4-CH3 (P) H3CCN 16 25 93 243-244 24 CH3 CH3 H H CO-(CH2)6-CH3 DMF 1 50 70 148-150 25 CH3 CH3 H H CO-C6H5 DMF 24 25 77,8 >360 26 CH3 CH3 H H SO2-CH3 CH3CN 5 25 97 250-251 Beispiel-Nr. R¹ R² R³ R4 R5 Lösungs- Reaktions- Reaktions- Ausbeute Fp. mittel zeit temperatur (h) (°C) (%) (°C) 27 CH3 CH3 CH3 H SO2-C6H4-CH3 (P) CH3CN 20 25 55 134-136 28 CH3 CH3 CH3 H SO2-CH3 CH3CN 5 25 81 174-176 29 CH3 CH3 C2H5 H SO2-C6H4-CH3 (P) CH3CN 20 25 81 176-180 30 CH3 CH3 C2H5 H SO2-CH3 CH3CN 5 25 94 159-161 31 CH3 CH3 CH3 CH3 CO-OC2H5 THF 20 25 75 149-152 32 CH3 CH3 CH3 CH3 CO-C6H5 THF 24 25 62 108-111 33 CH3 CH3 CH3 CH3 CO-C6H5-Cl (P) THF 24 25 89,5 151-153 34 CH3 CH3 CH3 CH3 SO2-C6H5-CH3 (P) CH3CN 20 25 67 134-136 35 CH3 CH3 CH3 CH3 SO2-CH3 CH3CN 16 25 81 116-118 36 CH3 C2H5 H H CO-(CH2)2-CH3 DMF 1 50 29,5 195-198 37 nC3H7 nC3H7 H H CO-(CH2)2-CH3 CH3CN 1 50 71,5 121-123 38 nC3H7 nC3H7 H H SO2-C6H4-CH3 (P) CH3CN 1 80 88,5 178-180 39 nC3H7 nC3H7 H H SO2-CH3 CH3CN 2 70 92 210-214 40 nC3H7 nC3H7 H H SO2-CH3 CH3CN 4 25 85 212-215 Beispiel-Nr. R¹ R² R³ R4 R5 Lösungs- Reaktions- Reaktions- Ausbeute Fp. mittel zeit temperatur (h) (°C) (%) (°C) 41 i C3H7 i C3H7 H H CO-OC2H5 THF 20 25 55,5 153-156 42 i C3H7 i C3H7 H H CO-C6H5 THF 24 25 73 134-136 43 i C3H7 i C3H7 H H CO-C6H4-Cl (P) THF 24 25 73,5 153-154 44 C4H9 C4H9 H H CO-OC2H5 DMF 20 25 85 115-120 45 C4H9 C4H9 H H CO-OC2H5 CH3CN 20 25 76 116-120 46 C4H9 C4H9 H H CO-C6H5 H3CCN 5 25 87,5 151-157 47 n C4H9 n C4H9 H H CO-C6H4-Cl (P) H3CCN 24 25 80 156-158 48 n C4H9 n C4H9 H H SO2-C6H4-CH3 (P) H3CCN 24 25 78 178-180 49 n C4H9 n C4H9 H H CO-(CH2)6CH3 H3CCN 1 50 73 91-93 50 n C4H9 n C4H9 H H CO-C6H4-NO2 (P) H3CCN 1 60 70 138-140 51 n C4H9 n C4H9 H H SO2-CH3 H3CCN 5 25 82,4 192-195 52 n C4H9 n C4H9 H H SO2-CH3 H3CCN 1 70 84 191-195 53 n C4H9 n C4H9 H H CO-(CH2)2CH3 H3CCN 2 50 71,5 115-122 54 CH2-C6H5 CH2-C6H5 H H CO-OC2H5 DMF 2 100 69,5 174-178 Beispeil-Nr. R¹ R² R³ R4 R5 Lösungs- Reaktions- Reaktions- Ausbeute Fp. mittel zeit temperatur (h) (°C) (%) (°C) 55 CH2-C6H5 CH2-C6H5 H H CO-OC2H5 H3CCN 3 80 77,2 177-178 56 CH2-C6H5 CH2-C6H5 H H SO2-C6H4-CH3 THF 16 25 83,5 213-215 57 CH2-C6H5 CH2-C6H5 H H CO-(CH2)6-CH3 H3CCN 1 50 60 147-150 58 CH2-C6H5 CH2-C6H5 H H CO-C6H4-NO2 (P) H3CCN 1 60 61 164-167 59 CH2-C6H5 CH2-C6H5 H H SO2-CH3 H3CCN 5 25 70,5 222-223 60 CH2-C6H5 CH2-C6H5 H H CO-(CH2)2-CH3 H3CCN 1 50 54 The 6-amino-uracil-5-carbonic acid thioamides listed in the following table were prepared according to this general procedure. @@ spiol no. R¹ R² R³ R4 R5 Solution Reaction Reaction Yield Mp. mean time temperature (h) (° C) (%) (° C) 1 HHHH CO-OC2H5 NMP 2 140 81> 360 2 HHHH CO-C6H5 NMP 2 140 58.5> 360 3 H CH3 HH SO2-C6H4-CH3 (P) CH3 CN1 80 87 245-255 4 H CH3 HH SO2-CH3 H3CCN 1 60 85 308-312 5 H C2H5 HH SO2-C6H4-CH3 (P) H3CCN 16 25 81.5 244-246 6H C2H5 HH SO2-C6H4-CH3 (P) H3CCN 1 80 73.6 240-248 7 H C2H5 HH SO2-CH3 H3CCN 1 70 92 268-270 8 H CH2-CH = CH2 HH SO2-C6H4-CH3 (P) H3CCN 16 25 92 223-224 9 H CH2-CH = CH2 HH SO2-C6H4-CH3 (P) H3CCN 1 80 94 226-228 10 H CH2-CH = CH2 HH SO2-CH3 H3CCN 4 25 98 256-260 11 H CH2-CH = CH2 HH SO2-CH3 H3CCN 1 70 94 250-260 12 H CH2-C6H5 HH CO-C6H4-NO2 (P) H3CCN 2 40 68.5> 320 13 H CH2-C6H5 HH SO2-C6H4-CH3 (P) H3CCN 1 80 86 234-236 Example no. R¹ R² R³ R4 R5 Solution Reaction Reaction Yield Mp. mean time temperature (h) (° C) (%) (° C) 14 H CH2-C6H5 HH SO2-CH3 H3CCN 4 25 92 243-245 15 H CH2-C6H5 HH SO2-CH3 H3CCN 1 70 89 240-243 16 H C6H5 HH CO-OC2H5 DMF 2 60 81.5 315-318 17 H C6H5 HH SO2-C6H4-CH3 (P) DMF 2 60 66 236-240 18 H C6H5 HH CO2-C6H4-NO2 (P) DMF 4 40 59> 300 19 CH3 CH3 HH CO-OC2H5 DMF 2 100 75 256-258 20 CH3 CH3 HH CO-OC2H5 CH3CN2 80 89.5 256-258 21 CH3 CH3 HH CO-OC2H5 THF 2 65 67 254-256 22 CH3 CH3 HH CO-C6H5-Cl (P) DMF 4 25 77 23 CH3 CH3 HH SO2-C6H4-CH3 (P) H3CCN 16 25 93 243-244 24 CH3 CH3 HH CO- (CH2) 6-CH3 DMF 1 50 70 148-150 25 CH3 CH3 HH CO-C6H5 DMF 24 25 77.8> 360 26 CH3 CH3 HH SO2-CH3 CH3CN 5 25 97 250-251 Example no. R¹ R² R³ R4 R5 Solution Reaction Reaction Yield Mp. mean time temperature (h) (° C) (%) (° C) 27 CH3 CH3 CH3 H SO2-C6H4-CH3 (P) CH3CN 20 25 55 134-136 28 CH3 CH3 CH3 H SO2-CH3 CH3CN 5 25 81 174-176 29 CH3 CH3 C2H5 H SO2-C6H4-CH3 (P) CH3CN 20 25 81 176-180 30 CH3 CH3 C2H5 H SO2-CH3 CH3CN 5 25 94 159-161 31 CH3 CH3 CH3 CH3 CO-OC2H5 THF 20 25 75 149-152 32 CH3 CH3 CH3 CH3 CO-C6H5 THF 24 25 62 108-111 33 CH3 CH3 CH3 CH3 CO-C6H5-Cl (P) THF 24 25 89.5 151-153 34 CH3 CH3 CH3 CH3 SO2-C6H5-CH3 (P) CH3CN 20 25 67 134-136 35 CH3 CH3 CH3 CH3 SO2-CH3 CH3CN 16 25 81 116-118 36 CH3 C2H5 HH CO- (CH2) 2-CH3 DMF 1 50 29.5 195-198 37 nC3H7 nC3H7 HH CO- (CH2) 2-CH3 CH3CN 1 50 71.5 121-123 38 nC3H7 nC3H7 HH SO2-C6H4-CH3 (P) CH3CN 1 80 88.5 178-180 39 nC3H7 nC3H7 HH SO2-CH3 CH3CN 2 70 92 210-214 40 nC3H7 nC3H7 HH SO2-CH3 CH3CN 4 25 85 212-215 Example no. R¹ R² R³ R4 R5 Solution Reaction Reaction Yield Mp. mean time temperature (h) (° C) (%) (° C) 41 i C3H7 i C3H7 HH CO-OC2H5 THF 20 25 55.5 153-156 42 i C3H7 i C3H7 HH CO-C6H5 THF 24 25 73 134-136 43 i C3H7 i C3H7 HH CO-C6H4-Cl (P) THF 24 25 73.5 153-154 44 C4H9 C4H9 HH CO-OC2H5 DMF 20 25 85 115-120 45 C4H9 C4H9 HH CO-OC2H5 CH3CN 20 25 76 116-120 46 C4H9 C4H9 HH CO-C6H5 H3CCN 5 25 87.5 151-157 47 n C4H9 n C4H9 HH CO-C6H4-Cl (P) H3CCN 24 25 80 156-158 48 n C4H9 n C4H9 HH SO2-C6H4-CH3 (P) H3CCN 24 25 78 178-180 49 n C4H9 n C4H9 HH CO- (CH2) 6CH3 H3CCN 1 50 73 91-93 50 n C4H9 n C4H9 HH CO-C6H4-NO2 (P) H3CCN 1 60 70 138-140 51 n C4H9 n C4H9 HH SO2-CH3 H3CCN 5 25 82.4 192-195 52 n C4H9 n C4H9 HH SO2-CH3 H3CCN 1 70 84 191-195 53 n C4H9 n C4H9 HH CO- (CH2) 2CH3 H3CCN 2 50 71.5 115-122 54 CH2-C6H5 CH2-C6H5 HH CO-OC2H5 DMF 2 100 69.5 174-178 Example no. R¹ R² R³ R4 R5 Solution Reaction Reaction Yield Mp. mean time temperature (h) (° C) (%) (° C) 55 CH2-C6H5 CH2-C6H5 HH CO-OC2H5 H3CCN 3 80 77.2 177-178 56 CH2-C6H5 CH2-C6H5 HH SO2-C6H4-CH3 THF 16 25 83.5 213-215 57 CH2-C6H5 CH2-C6H5 HH CO- (CH2) 6-CH3 H3CCN 1 50 60 147-150 58 CH2-C6H5 CH2-C6H5 HH CO-C6H4-NO2 (P) H3CCN 1 60 61 164-167 59 CH2-C6H5 CH2-C6H5 HH SO2-CH3 H3CCN 5 25 70.5 222-223 60 CH2-C6H5 CH2-C6H5 HH CO- (CH2) 2-CH3 H3CCN 1 50 54

Claims (4)

Patent ansprüche 0 6-Amino-uracil-5-carbonsäure-thioamide der Formel in der R1 Wasserstoff, gegebenenfalls substituiertes Alkyl, Cycloalkyl oder Aralkyl, R2 unabhängig -von R1 Wasserstoff, gegebenenfalls substituiertes Alkyl, Cycloalkyl, Aralkyl, Phenyl oder einen gegebennfalls substituierten heterocyclischen Rest, Wasserstoff, gegebenenfalls substituiertes Alkyl, Cyclo alkyl, Aralkyl oder Aryl, R4 Wasserstoff, gegebenenfalls substituiertes Alkyl, Cycloalkyl, Aralkyl oder Aryl, R3 und R4 zusammen mit dem Stickstoff einen heterocyclischen Rest und R5 einen Sulfonyl- oder Acylrest bedeuten.Patent claims 0 6-Amino-uracil-5-carboxylic acid thioamides of the formula in which R1 is hydrogen, optionally substituted alkyl, cycloalkyl or aralkyl, R2 independently of R1 is hydrogen, optionally substituted alkyl, cycloalkyl, aralkyl, phenyl or an optionally substituted heterocyclic radical, hydrogen, optionally substituted alkyl, cycloalkyl, aralkyl or aryl, R4 Hydrogen, optionally substituted alkyl, cycloalkyl, aralkyl or aryl, R3 and R4 together with nitrogen denote a heterocyclic radical and R5 denote a sulfonyl or acyl radical. 2. Verbindungen gemäß Anspruch 1 der Formel in der A Wasserstoff, Alkyl mit 1 bis 4 C-Atomen oder Alkoxyalkyl mit insgesamt 3 bis 8 C-Atomen, A1 und A2 Wasserstoff oder Alkyl mit 1 bis 4 C-Atomen-und A3 Alkylsulfonyl mit 1 bis 4 C-Atomen, Arylsulfonyl, Alkoxycarbonyl mit 2 bis 5 C-Atomen, Phenoxycarbonyl oder Aroyl bedeuten.2. Compounds according to claim 1 of the formula in which A is hydrogen, alkyl with 1 to 4 carbon atoms or alkoxyalkyl with a total of 3 to 8 carbon atoms, A1 and A2 are hydrogen or alkyl with 1 to 4 carbon atoms and A3 is alkylsulfonyl with 1 to 4 carbon atoms, arylsulfonyl , Alkoxycarbonyl with 2 to 5 carbon atoms, phenoxycarbonyl or aroyl. 3, Ein Verfahren zur Herstellung von Verbindungen gemäß Anspruch 1 oder 2, dadurch gekennzeichnet, , daß man ein 6-Aminouracil der Formel in der R1, R2, R3 und R4 die angegebene Bedeutung haben, mit Isothiocyanaten der allgemeinen Formel R5 - N = C = S umsetzt, wobei R5 die angegebene Bedeutung hat.3, A process for the preparation of compounds according to claim 1 or 2, characterized in that a 6-aminouracil of the formula in which R1, R2, R3 and R4 have the meaning given, with isothiocyanates of the general formula R5 - N = C = S, where R5 has the meaning given. 4. Die Verwendung der Verbindungen gemäß Anspruch 1 oder 2 zur Herstellung von Diazokomponenten.4. The use of the compounds according to claim 1 or 2 for the preparation of diazo components.
DE19712150686 1971-10-12 1971-10-12 6-amino-uracil-5-carboxylic acid thioamides - inters for dyestuffs and pharmaceuticals Pending DE2150686A1 (en)

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US7687625B2 (en) 2003-03-25 2010-03-30 Takeda Pharmaceutical Company Limited Dipeptidyl peptidase inhibitors
US7723344B2 (en) 2003-08-13 2010-05-25 Takeda San Diego, Inc. Dipeptidyl peptidase inhibitors
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US8906901B2 (en) 2005-09-14 2014-12-09 Takeda Pharmaceutical Company Limited Administration of dipeptidyl peptidase inhibitors
US8222411B2 (en) 2005-09-16 2012-07-17 Takeda Pharmaceutical Company Limited Dipeptidyl peptidase inhibitors
US8324383B2 (en) 2006-09-13 2012-12-04 Takeda Pharmaceutical Company Limited Methods of making polymorphs of benzoate salt of 2-[[6-[(3R)-3-amino-1-piperidinyl]-3,4-dihydro-3-methyl-2,4-dioxo-1(2H)-pyrimidinyl]methyl]-benzonitrile
US8084605B2 (en) 2006-11-29 2011-12-27 Kelly Ron C Polymorphs of succinate salt of 2-[6-(3-amino-piperidin-1-yl)-3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethy]-4-fluor-benzonitrile and methods of use therefor
US8093236B2 (en) 2007-03-13 2012-01-10 Takeda Pharmaceuticals Company Limited Weekly administration of dipeptidyl peptidase inhibitors

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