Patent GB-1424946-A (GB)
Title: Benzoylphenyl-isothioureas, their production and their medicinal use
IPC: C07C335/30
Filed: 1974-01-23
Abstract: 1424946 Benzoylphenylisothioureas BAYER AG 23 Jan 1974 [23 Jan 1973 16 May 1973 9 Aug 1973 26 Oct 1973] 03136/74 Heading C2C The invention comprises novel compounds (I) in which R is an alkyl radical with 1-12 carbon atoms, a cycloalkyl radical with up to 8 carbon atoms, an alkenyl radical with up to 12 carbon atoms, or an aralkyl radical (optionally carrying in the aryl part one or more substituents selected from alkyl and alkoxy radicals, each with one to four carbon atoms, and halogen radicals); R<SP>1</SP> is an alkyl radical with 1-4 carbon atoms, a cyclohexyl radical or a phenyl radical; R<SP>2</SP> is a hydrogen atom, or an alkyl radical with 1-18 carbon atoms (optionally carrying one or more substituents selected from halogen and nitrile radicals, alkoxy radicals with 1-4 carbon atoms, alkoxycarbonyl radicals with 2-5 carbon atoms, phenoxy, halophenoxy, alkylphenoxy and alkoxyphenoxy radicals), or a cycloalkyl radical with 5-8 carbon atoms, or an aralkyl radical (optionally carrying one or more substituents selected from halogen atoms, alkyl radicals with 1-4 carbon atoms and alkoxy radicals with 1-4 carbon atoms), or an aryl radical (optionally carrying one or more substituents selected from halogen atoms, alkyl radicals with 1-4 carbon atoms and alkoxy radicals with 1-4 carbon atoms) or a 1-furyl radical, or a group of the general formula -NR<SP>11</SP>R<SP>111</SP>, [in which R<SP>11</SP> is a hydrogen atom or an alkyl radical with 1-4 carbon atoms, and R<SP>111</SP> is a hydrogen atom or an alkyl radical with 1-18 carbon atoms (optionally carrying one or more substituents selected from halogen and nitrile radicals, alkoxy radicals with up to 4 carbon atoms, alkoxycarbonyl radicals with up to 5 carbon atoms), or a cycloalkyl radical with 5-8 carbon atoms, or an aralkyl radical (optionally carrying in the aryl part one or more substituents selected from halogen, C 1  to C 6  alkyl and C 1  to C 6  alkoxy radicals), or a phenyl radical (optionally carrying one or more substituents selected from halogen, C 1  to C 6  alkyl and C 1  to C 6  alkoxy radicals), or an acyl radical with up to 18 carbon atoms (optionally carrying one or more substituents selected from halogen and C 1  to C 6  alkoxy radicals), or an aroyl radical (optionally carrying one or more substituents selected from halogen, C 1  to C 6  alkyl and C 1  to C 6  alkoxy radicals), or an alkylsulphonyl radical with up to 18 carbon atoms, or an arylsulphonyl radical (optionally carrying one or more substituents selected from halogen, amino, C 1  to C 6  alkoxy and C 1  to C 6  alkyl radicals), or a dialkylamino radical with up to 4 carbon atoms; and R<SP>11</SP> and R<SP>111</SP> can also, together with the nitrogen atom linking them, represent a heterocyclic ring with 4 to 7 carbon atoms, and optionally additionally containing 1 oxygen or sulphur atom]. They are made by alkylating compounds (II). 2 - Nitro - 4 - benzoyl - acetanilide (obtained from 2-nitro-4-benzoyl-aniline) is hydrogenated to give 2-amino-4-benzoylacetanilide which, in turn, is treated with potassium thiocyanate and methyl chloroformate to give N - (2 - acetamido - 5 - benzoylphenyl) - N<SP>1</SP>- methoxycarbonyl-thiourea. Pharmaceutical preparations showing anthelmintic action contain (1) as active ingredient; standard administration forms are described.