Pharmacologically active 1,3-bis[(2-heterocyclyl-methyl-thio)ethyl)ethyl)guanidino]alkane derivatives
AssigneeSmithKline & French Laboratories Limited
InventorsGraham J. Durant, Charon R. Ganellin, George S. Sach
Life of this patent
Estimating the term…
Abstract
The compounds are C.sub.2 -C.sub.8 straight chain alkanes terminally substituted, symmetrically or unsymmetrically, by N-(N'-substituted guanidino), N-(N', N"-disubstituted guanidino), N-(N'-substituted thioureido), N-(nitromethylene amidino) or S-(N-substituted isothioureido)groups. Two compounds of the invention are 1,3-bis[N'-(2-(3-methoxy-2-pyridylmethylthio)ethyl)guanidino]propane and 1-[N-(2-(3-methoxy-pyridylmethylthio)ethyl)guanidino]-3-[N'-2-(5-methyl-4- imidazolylmethylthio)ethyl)guanidino]propane. The compounds of this invention are inhibitors of H-2 histamine receptors.
Claims9
A compound of the formula ##STR4## wherein X.sup.1 and X.sup.2, which may be the same or different, are each NY where Y is hydrogen, hydroxy or lower alkyl;
- R.sup.1 is a grouping of the structure ##STR5## wherein R.sup.3 is lower alkyl or --(CH.sub.2).sub.p A where p is 2 to 4, and A is hydroxy, lower alkoxy or dimethylamino;
- R.sup.4 is hydrogen, lower alkyl, lower alkoxy, amino, halogen or methylamino;
- Z is sulphur or methylene;
- n is 2 or 3;
- R.sup.2 has the same scope as R.sup.1 or is a grouping of the structure
- Het--(CH.sub.2).sub.m' Z'(CH.sub.2).sub.n' --
- wherein Het is a nitrogen containing 5 or 6 membered heterocyclic ring selected from the group consisting of imidazole, pyridine, thiazole, isothiazole, oxazole, isoxazole, pyrazole, triazole and thiadiazole which is optionally substituted by lower alkyl, hydroxy, halogen or amino;
- Z' is sulphur or methylene;
- m' is 0, 1 or 2;
- n' is 2 or 3 and the sum of m' and n' is 3,4;
- W is NH, and when X.sup.1 and X.sup.2 are both NH, W may also be sulphur;
- and q is an integer from 2 to 8 or a pharmaceutically acceptable acid addition salt thereof.
Dependencies are inferred from the claim text.