Camptothecin derivatives and its manufacturing method

C - Chemistry – Metallurgy – 07 – D

Patent

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Details

C07D 491/22 (2006.01) A61K 31/47 (2006.01) A61K 31/535 (2006.01) C07D 491/14 (2006.01) C07D 491/147 (2006.01)

Patent

CA 2208639

This invention relates to a camptothecin compound and a pharmaceutically acceptable salt thereof, its manufacturing method, an antineoplastic agent containing it, and intermediates of synthesis of the compound. The compound of this invention is a camptothecin derivative modified in B-ring and E-ring form and having improved water solubility and an enhanced antineoplastic effect. The compound is of the general formula I defined as follows: Image wherein R is hydrogen or -(CH2)2-NR1R2 where R1 is hydrogen or an amino protecting group and R2 is a lower alkyl, hydroxyethyl or acetoxyethyl group, or R1 and R2, together with the nitrogen atom to which they are attached, form a morpholine, piperidine or pyrrolidine ring; n is 1 or 2; and R3 is hydrogen or -OR4, where R4 is hydrogen, COR5, CONHR6, or CH2OR7, where R5 is methyl or CH3OCH2-, R6 is isopropyl, phenyl or -CH2CH2Cl and R7 is methyl, ethyl, or CH3OCH2CH2-; with the provisos that: R and R3 cannot both be hydrogen; when n is 2 and R is -(CH2)2N(Cbz)CH3, then R3 cannot be hydrogen; when n is 2 and R3 is OH, then R cannot be hydrogen; and when R is -CH2CH2 NHCH3, then R3 cannot be hydrogen.

Dérivés de camptothécine, leurs sels pharmaceutiquement acceptables, leur procédé de fabrication, et agent antinéoplasique les contenant. Les composés de l'invention sont des dérivés de camptothécine modifiés au niveau des noyaux B et E, ce qui améliore leur hydrosolubilité et leur action antinéoplasique.

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