Drug-monoclonal antibody conjugates

Claim 1

An anti-tumor drug-monoclonal antibody conjugate having the general structural formula: wherein: D is a 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 R¹NH-, a secondary amino group represented by the formula R¹R²N-, and a alcohol group represented by the formula R¹O-; R¹ 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 wherein, in the case of a secondary amino group, when R¹ and R² are independent. R², when R¹ and R² are independent, is selected from unsubstituted and substituted and branched and straight-chain alkyl groups having 1-10 carbon atoms wherein the substituent 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, as substituted as defined above in the case of substituted phenyl and the alkyl moiety is a polyakylene group having 1 to 3 carbon atoms; R¹ and R², 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 R³ and R⁴, independently, are selected from H and unsubstituted and substituted, and branched and straight-­chain alkyl groups having 1-10 carbon atoms wherein the substituent is selected from 1 to 3 alkoxy groups having 1 to 3 carbon atoms and 1 to 3 halo groups; unsubsituted 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 and 10; and Ab represents a monoclonal antibody having a pendent amino group; and the orientation of the group, -S-S-(CR³R⁴) m - -NHAb, on the phenyl ring of the benzylcarbamate moiety is selected from the ortho- and para-positions.