Smith Kline & French Laboratories Limited

George R White

Graham J Durant

Charon R Ganellin

Ronald Joseph King

Derek W Hills

Torben Hesselbo

Process for preparing N-cyano-N'-methyl-1-aziridinoamidine by reacting aziridine with a N-cyano-N'-methyl-O-arylisourea.

Process for preparing an aziridine derivative

The invention provides 2-[2-(5-methyl-4-imidazolylmethylthio)ethylamino]-5-[5-(1,3-benzodioxolyl) methyl]-4-pyrimidone di(methanesulphonate) which is useful as a histamine H.sub.2 -antagonist. The compound can be prepared by reacting 2-[2-(5-methyl-4-imidazolylmethylthio)ethylamino]-5-[5-(1,3-benzodioxolyl) methyl]-4-pyrimidone with methanesulphonic acid.

Pyrimidone salt and its preparation

This invention relates to a process for preparing imidazolylalkylguanidines, in particular N-[3-(4-imidazolyl)propyl]-N'-[2-(5-methyl-4-imidazolylmethylthio)ethyl]gu anidine (impromidine) which has histamine H.sub.2 -agonist activity, to intermediates for use in this process and to processes for preparing these intermediates.

Tetrahydroimidazo(3,4-c)-1,3-diazocine intermediates for production of

The compounds are sulphoxides of heterocyclicthioalkylthioureas, ureas and guanidines which are useful to produce inhibition of histamine H-2 receptors.

Sulphoxides

3-,4-Dihydroimidazo (3,4-c)-1,3-pyrimidines and 4,5-dihydroimidazo

Sulphoxides of heterocyclicthioalkylthioureas, ureas and guanidines

Imidazole derivatives which are useful intermediates for the production of compounds having pharmacological activity at histamine H.sub.2 receptors. A specific compound of the present invention is 4-(4-aminobutyl)-1,3-dihydro-5-methyl-2H-imidazole-2-thione, hereinafter referred to as 4-(4-Aminobutyl)-5-methylimidazole-2-thione.

2H-imidazole-2-thione derivatives

Isothiazole and isoxazole sulphoxides

The compounds are heterocyclomethylsulphinylethyl derivatives of N-cyanoguanidines, thioureas and 2-amino-1-nitroethylene which are histamine H.sub.2 -antagonists or are converted into histamine H.sub.2 -antagonists in the animal body. Two specific compounds of the present invention are 1-nitro-2-[2-((2-thiazolyl)methylsulphinyl)ethylamino]-2-[2-((2-thiazolyl) methylthio)ethylamino]ethylene and 1-nitro-2,2-bis-[2-((2-thiazolyl)methylsulphinyl)ethylamino]ethylene.

Heterocyclomethylsulphinylethyl derivatives of N-cyanoguanidines,

Process for preparing thioureas by treating isothiocyanates with ammonia and alkylamines. A specific product is N-methyl-N'-[2-((5-methyl-4-imidazolyl)methylthio)ethyl]thiourea, useful as a histamine H.sub.2 -antagonist.

Certain nitrogen heterocyclic isothiocyanate esters

Process for preparing N-cyanoguanidines by treating N-(loweralkyl)-N'-cyano-isothioureas with an amine and a heavy metal salt. A specific product is N-cyano-N'-methyl-N'-[2-((5-methyl-4-imidazolyl)methylthio)ethyl]guanidine , useful as a histamine H.sub.2 -antagonist.

Process for preparing N-cyanoguanidines

Certain thiazolyl and isothiazolyl compounds and compositions and

A process for preparing 2-amino-2-alkylthio-1-nitroethylene compounds by reacting a 1-lower alkylsulfinyl-1-lower alkylthio-2-nitroethylene with an amine. The products of the process are intermediates for the production of histamine H.sub.2 -antagonists.

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Harpenden, United Kingdom

George R White