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Trialkyl-lock-facilitated polymeric prodrugs of amino-containing bioactive agents



Trialkyl-lock-facilitated polymeric prodrugs of amino-containing bioactive agents



Official Gazette of the United States Patent & Trademark Office Patents 1227(2), Oct 12



The present invention is directed to double prodrugs containing polymeric-based transport forms. These polymeric prodrugs are preferably of the formula: ##STR1## wherein: B is a leaving group or a residue of an amine-containing target moiety; G is ##STR2## or CH2 ; Y1-2 are independently O or S; M is X or Q; where X is an electron withdrawing group and Q is a moiety containing a free electron pair positioned three to six atoms from C(dbdY2); R1, R4, R7, R8, R9, R10 and R13 are independently selected from the group consisting of hydrogen, C1-6 alkyls, C3-12 branched alkyls, C3-8 cycloalkyls, C1-6 substituted alkyls, C3-8 substituted cycloalkyls, aryls, substituted aryls, aralkyls, C1-6 heteroalkyls, substituted C1-6 heteroalkyls; R2, R3, R5 and R6 are independently selected from the group consisting of hydrogen, C1-6 alkyls, C1-6 alkoxy, phenoxy, C1-8 heteroalkyls, C1-8 heteroalkoxy, substituted C1-6 alkyls, C3-8 cycloalkyls, C3-8 substituted cycloalkyls, aralkyls, aryls, substituted aryls, such as aryls substituted with halo-, nitro- and cyano-; carboxy-, C1-6 carboxyalkyls and C1-6 alkyl carbonyls; (m) is zero or one; (n) is zero or a positive integer; (p) is zero, one or two; and R11 is a substantially non-antigenic polymer. The first prodrug is generated when the polymeric portion of the double prodrug is cleaved and the parent molecule is generated rapidly thereafter in vivo, as a result of a trialkyl lock type lactonization-type reaction.

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Accession: 035985906

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