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Generated: December 14, 2017

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Title: Pharmacologically active thiourea and urea compounds
Abstract:The compounds are substituted thioalkyl-, aminoalkyl- and oxyalkyl-thioureas and ureas which are inhibitors of histamine activity.
Inventor(s): Durant; Graham John (Welwyn Garden City, EN), Emmett; John Colin (Codicote, EN), Ganellin; Charon Robin (Welwyn Garden City, EN)
Assignee: Smith Kline & French Laboratories Limited (Welwyn Garden City, EN)
Filing Date:Mar 14, 1974
Application Number:05/451,333
Claims:1. A compound of the formula: ##SPC12##

wherein A is such that there is formed together with the carbon atom shown an unsaturated heterocyclic nucleus, said unsaturated heterocyclic neucleus being an imidazle or pyrazole ring;

X.sub.1 is hydrogen, lower alkyl, hydroxyl, trifluoromethyl, benzyl, halogen, amino or ##EQU6## X.sub.2 is hydrogen or when X.sub.1 is lower alkyl, lower alkyl or halogen; k is 0 to 2 and m is 2 or 3, provided that the sum of k and m is 3 or 4; Y is oxygen, sulphur or NH; E is oxygen or sulphur; and R.sub.1 is hydrogen, lower alkyl, benzoyl or di-lower alkylamino-lower alkyl or a pharmaceutically acceptable addition salt thereof with the proviso that X.sub.1 is ##EQU7## only when Y and E are sulphur and R.sub.1 is methyl and with the proviso that when X1 is other than hydrogen or lower alkyl and X.sub.2 is other than hydrogen, X.sub.1 and X.sub.2 are attached at carbon atoms.

2. A compound of claim 1 wherein Y is oxygen or sulphur.

3. A compound of claim 1 wherein Y is NH.

4. A compound of claim 1 wherein k is 1 and m is 2.

5. A compound of claim 1 wherein said unsaturated nucleus is imidazole.

6. A compound of claim 2 in which X.sub.1 is hydrogen, methyl, bromo, hydroxyl or amino and X2 is hydrogen; Y and E are sulphur and R.sub.1 is methyl.

7. A compound of claim 5 wherein X.sub.1 is hydrogen, lower alkyl, trifluoromethyl, benzyl, halogen or ##EQU8## X.sub.2 is hydrogen or when X.sub.1 is lower alkyl, lower alkyl or halogen; k is 0 to 2 and m is 2 or 3, provided that the sum of k and m is 3 or 4; Y is oxygen or sulphur; E is oxygen or sulphur and R.sub.1 is hydrogen, lower alkyl, benzoyl or di-lower alkylamino-lower alkyl or a pharmaceutically acceptable addition salt thereof.

8. A compound of claim 1, said compound being N-methyl-N'-[2-(4-imidazolylmethylthio)ethyl]thiourea.

9. A compound of claim 1, said compound being N-methyl-N'-[2-((5-methyl-4-imidazolyl)methylthio)ethyl]-thiourea.

10. A compound of claim 1, said compound being N-methyl-N'-[2-((5-bromo-4-imidazolyl)methylthio)ethyl]thiourea.

11. A compound of claim 1, said compound being N-methyl-N'-[2-((1-methyl-2-imidazolyl)methylthio)ethyl]thiourea.

12. A compound of claim 1, said compound being N-methyl-N'-[2-(2-imidazolylmethylthio)ethyl]thiourea.

13. A compound of claim 1, said compound being N-methyl-N'-[2-(3-pyrazolylmethylthio)ethyl]thiourea.
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