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Claims for Patent: 3,950,333

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Claims for Patent: 3,950,333

Title: Pharmacologically active guanidine compounds
Abstract:The compounds are substituted thioalkyl-, aminoalkyl- and oxyalkyl-guanidines 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)
Application Number:05/450,957
Patent Claims: 1. A compound of the formula: ##SPC10##

wherein A is such that there is formed together with the carbon atom shown an unsaturated heterocyclic nucleus, said unsaturated heterocyclic nucleus being an imidazole, pyrazole, pyrimidine, pyrazine or pyridazine ring; X.sub.1 is hydrogen, lower alkyl, hydroxy, trifluoromethyl, benzyl, halogen, amino or ##EQU6## in which E' is NH or N-cyano; 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 NR.sub.2 ; R.sub.1 is hydrogen, lower alkyl or di-lower alkylamino-lower alkyl; and R.sub.2 is hydrogen, nitro or cyano, or a pharmaceutically acceptable addition salt thereof with the proviso that X.sub.1 is ##EQU7## only when E is NH or N-cyano.

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 said unsaturated heterocyclic nucleus is imidazole, pyrazole, pyrimidine pyrazine or pyridazine and R.sub.2 is hydrogen or nitro.

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

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

7. A compound of claim 6 wherein X.sub.1 is hydrogen, methyl, bromo, hydroxyl or amino and X.sub.2 is hydrogen; Y is sulphur and R.sub.1 is methyl.

8. A compound of claim 1, said compound being N-cyano-N'-methyl-N"-[2-((4-methyl-5-imidazolyl)-methylthio)ethyl]guanidin e.

9. A compound of claim 1, said compound being 2-(4-imidazolylmethylthio)ethyleneguanidine sulphate.

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

11. A compound of claim 1, said compound being N-cyano-N'-ethyl-N"-[2-((4-methyl-5-imidazolyl)-methylthio)ethyl]guanidine

12. A compound of claim 1, said compound being N-[2-((4-bromo-5-imidazolyl)methylthio)ethyl]-N'-cyano-N"-methylguanidine.

13. A compound of claim 1, said compound being N-cyano-N"-[2-((4-methyl-5-imidazolyl)methylthio)ethyl]guanidine.

14. A compound of claim 1, said compound being N-cyano-N'-[2-(4-imidazolylmethylthio)ethyl]-N"-methylguanidine.

15. A compound of claim 1, said compound being N-cyano-N'-[2-((4-methyl-5-imidazolyl)methylthio)-ethyl]-N"-propylguanidin e.

16. A compound of claim 1, said compound being N-cyano-N'-methyl-N"-[2-((1-methyl-2-imidazolyl)-methylthio)ethyl]guanidin e.

17. A compound of claim 1, said compound being N-cyano-N'-[2-(2-imidazolylmethylthio)ethyl]-N"-methylguanidine.

18. A compound of claim 1, said compound being N-cyano-N'-methyl-N"-[2-((5-trifluoromethyl-4-imidazolyl)methylthio)ethyl] guanidine.

19. A compound of claim 1, said compound being N-cyano-N'-[2-(4-imidazolylmethoxy)ethyl]-N"-methylguanidine.

20. A compound of claim 1 said compound being N-cyano-N'-methyl-N"-[2-(3-pyrazolylmethylthio)-ethyl]guanidine.

21. A compound of claim 1, said compound being N-cyano-N'-methyl-N"-[2-(2-pyrazinylmethylthio)ethyl]guanidine.

22. A compound of claim 1, said compound being N-cyano-N'-methyl-N"-[2-(3-pyridazinylmethylthio)ethyl]guanidine.
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