Drug-monoclonal antibody conjugates

Claim 1

An anti-tumor drug-Monoclonal antibody conjugate having the general structural formula: ##STR3## wherein: D is an anti-tumor drug moiety having pendant to the backbone thereof a chemically reactive functional group, by means of which the drug backbone is bonded to the disulfide benzyloxycarbonyl group, derived from the group consisting of a primary amino group represented by the formula R 1 NH--, a secondary amino group represented by the formula R 1 R 2 N--, and an alcohol group represented by the formula R 1 O--; R 1 , when R 1 and R 2 are independent, is the backbone of said drug moiety when D is derived from the group consisting of a primary amino group, a secondary amino group, and an alcohol group; R 2 , when R 1 and R 2 are independent, is selected from unsubstituted and substituted and branched and straight-chain alkyl groups having 1-10 carbon atoms wherein the substitutent is selected from 1 to 3 alkoxy groups having 1 to 3 carbon atoms and 1 to 3 halo groups; unsubstituted and substituted phenyl wherein the substituent is selected from 1 to 3 alkyl groups having 1 to 3 carbon atoms, 1 to 3 alkoxy groups having 1 to 3 carbon atoms, and 1 to 3 halo groups; and unsubstituted and substituted phenalkyl wherein the phenyl moiety, when substituted, is substituted as defined above in the case of substituted phenyl and the alkyl moiety is a polyalkylene group having 1 to 3 carbon atoms; R 1 and R 2 , when taken together in a functional group derived from a secondary amine, represent the backbone of the drug moiety, D, having a divalent group chemically bonded to the nitrogen atom constituting said secondary amino group; and R 3 and R 4 , independently, are selected from H and unsubstituted and substituted, and branched and straight-chain alkyl groups having 1-10 carbon atoms wherein the substitutent is selected from 1 to 3 alkoxy groups having 1 to 3 carbon atoms and 1 to 3 halo groups; unsubstituted and substituted phenyl wherein the substituent is selected from 1 to 3 alkyl groups having 1 to 3 carbon atoms, 1 to 3 alkoxy groups having 1 to 3 carbon atoms, and 1 to 3 halo groups; and unsubstituted and substituted phenylalkyl wherein the phenyl moiety, when substituted, is substituted as defined above in the case of substituted phenyl and the alkyl moiety is a polyalkylene group having 1 to 3 carbon atoms; m is an integer selected from 1 to 10; and Ab represents a monoclonal antibody having a pendent amino group; and the orientation of the group, ##STR4## on the phenyl ring of the benzylcarbamate moiety is selected from the ortho- and para-positions.