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AssigneeThe United States of America as represented by the Department of Health and Human Services
InventorsJeffrey S. Fedan, John P. O'Donnell, G. Kurt Hogaboom
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Specific method of irreversible antagonism of histamine receptors, especially H.sub.1 receptors, in, for example, isolated guinea pig vas deferens by 4(5)-[2-(4-azido-2-nitroanilino)ethyl]imidazole (AAH), which is a photoaffinity analog of histamine actuated unusually by light in the visible spectrum. Additionally, compounds of the present invention are represented by the formula ##STR1## wherein R.sub.1 and R.sub.2 represent an electron withdrawing group of the formula, H, --NO.sub.2, --Cl, --F, --Br, --I, --SO.sub.3 H. When two groups occur, it is not necessary that those groups be identical. In preferred compounds R.sub.1 is --NO.sub.2 and R.sub.2 is H and R.sub.1 is ortho to amine group. R.sub.3, R.sub.4, R.sub.5 and R.sub.6 represent a proton or lower alkyl of straight and branched carbon chains. In preferred compounds R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are protons or methyl groups with not more than two of the four positions substituted with an alkyl group. Preference is given for R.sub.4 and R.sub.5.
A method of producing irreversible H.sub.1 -histamine antagonism in vitro comprising irradiating an effective concentration of an antagonist selected from the group consisting of ##STR4## wherein R.sub.1 is NO.sub.2 and R.sub.2 is H and R.sub.1 is ortho to the amine group, and wherein R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are H or lower alkyl groups with not more than two of the four positions substituted with a lower alkyl group with visible light in the presence of histamine receptor ligands.
Dependencies are inferred from the claim text.