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September 1951


Author Affiliations

With the Technical Assistance of Doris M. Kurth, R. Edith Eisenhauer, and Kathryn Rupp MADISON, WIS.

From the Department of Medicine, University of Wisconsin Medical School.

AMA Arch Intern Med. 1951;88(3):296-309. doi:10.1001/archinte.1951.03810090027003

THE FIRST synthesis of the 4-hydroxycoumarin anticoagulant No. 63, a compound chemically related to bishydroxycoumarin (dicumarol® 3,3′-methylenebis [4-hydroxycoumarin] ), was by Dr. Myoshi Ikawa in 1942 in Dr. Karl Paul Link's laboratory.1 It is a colorless and stable product which is readily prepared in pure form, and its solubility in water is of the order of 1/100 that of bishydroxycoumarin. Chemically anticoagulant No. 63 is 2-methyl-2-methoxy-4-phenyl-5-oxodihydropyrano-(3,2-c) (1) benzopyran. In work done by Scheel2 in the mouse, rat, rabbit, and dog, attention was given not only to activity per se, as reflected by the prolongation of the 12.5% plasma-prothrombin time, but also to the time and site of appearance of visible hemorrhage and the survival time resulting from continued administration of various coumarin anticoagulants. He concluded that 4-hydroxycoumarin anticoagulant No. 63 was a strong competitor, if not an agent superior, to bishydroxycoumarin. In dogs and in human beings this anticoagulant was

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