Thienamycin intermediates

Details Thienamycin intermediates Thienamycin intermediates

C - Chemistry, Metallurgy

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C07D 205/08 (2006.01) C07D 207/277 (2006.01) C07D 405/04 (2006.01) C07D 411/04 (2006.01) C07D 477/18 (2006.01) C07D 487/04 (2006.01)

Patent

CA 1190931

ABSTRACT OF THE DISCLOSURE New bicyclic compounds of the general formula (I), Image wherein Y1 and Y2 represent a removable carbonyl protecting group, and Q is a C1-5 alkyl group or a substituted benzyl group, are prepared in the way that protecting group X of a compound having the general formula (V), Image (v) wherein X is a selectively removable esterifying group, is re- moved, the carboxy group of the resulting compound of the general formula (IV) Image (VI) is activated and reacted then with a salt of a malonic acid hemiester, wherein the alcohol component is a C1-5 aliphatic alcohol or substituted benzyl alcohol, the resulting com- pound of the general formula (III) Image (III) - 2 - is reacted with a sulfonic azide in the presence of a tertiary amine, and the resulting compound of the general formula (II) Image (II) is subjected to ring closure. The compounds of the general formula (I) are pharmacologically active or can be converted into pharmaco- logically active thienamycin derivatives.

418742

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