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US 2010/0167992 A1Published application
Phenyl Ester Side Chains to Increase Polymer Resorptivity
AssigneeTYRX, Inc.
InventorsArthur Schwartz, Satish Pulapura, Sarita Nethula
Life of this patent
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Abstract
The present invention relates to polymers modified to increase their resorbability. In particular, the polymers of the invention have phenyl ester side chains which are good leaving groups and which thereby increase the resorption rate of the polymer relative to the same polymer, for example, bearing a comparable amount of an alkyl ester side chain. Such polymers are generally water insoluble, but when modified are able to solublize drugs and upon degradation and resorption, release those in a physiological environment in a controlled and/or sustained manner.
Claims49
A polymer comprising one or more monomer units represented by the formula:
- wherein
- “Monomer” is the repeating unit of a biocompatible, biodegradable polymer capable of resorption under physiological conditions;
- R′ is phenyl-R , wherein from zero to five R substituents are present at any position on the phenyl ring, and each R is independently linear or branched, substituted or unsubstituted, saturated or unsaturated alkyl, aryl, alkylaryl, heteroatom-containing alkyl or aryl, alkylcycloalkyl, alkoxy, aryloxy or alkylether having from 1 to 20 carbon atoms;
- halide;
- nitro;
- —(R2)rO((CR3R4)aO)s—Rs;
- —O((CR3R4)aO)s—R5;
- —C(O)—R5;
- —(R2)bC(O)—YR6;
- a protected hydroxyl group;
- a protected amino group or a protected carboxylic acid group;
- Y is —O— or —NH—;
- each R2 is linear or branched, lower alkylene or lower alkenylene;
- each R3 and R4 is independently hydrogen, or linear or branched lower alkyl;
- each R5 is independently linear or branched, substituted or unsubstituted, saturated or unsaturated alkyl;
- each R6 is hydrogen;
- saturated or unsaturated alkyl, aryl or alkylaryl having from 1 to 20 carbon atoms;
- or —(R2)rO((CR3R4)aO)s—R5;
- each a is independently 1 to 4;
- each b is independently zero or one;
- each r is independently 1 to 4;
- and each s is independently 1 to 5000.
19 more elements
A monomeric compound represented by Formula III or IV
- wherein
- B is a trivalent, linear or branched, substituted or unsubstituted alkyl, alkenyl, aryl or alkylaryl moiety having 1-20 carbon atoms, or is
- each of Z1 and Z2 represent from zero to four substituents, each of which is independently selected from the group consisting of halide, lower alkyl, alkoxy, nitro, alkylether, a protected hydroxyl group, a protected amino group and a protected carboxylic acid group;
- R represents from zero to five substituents at any position on the phenyl ring, and each R is independently linear or branched, substituted or unsubstituted, saturated or unsaturated alkyl, aryl, alkylaryl, heteroatom-containing alkyl or aryl, alkylcycloalkyl, alkoxy, aryloxy or alkylether having from 1 to 20 carbon atoms;
- halide;
- nitro;
- —(R2)rO((CR3R4)aO)s—R5;
- —O((CR3R4)al O)S—R5;
- —C(O)—R5;
- —(R2)bC(O)O—YR6;
- a protected hydroxyl group;
- a protected amino group or a protected carboxylic acid group;
- each R2 is independently linear or branched, lower alkylene or lower alkenylene;
- each R3 and R4 is independently hydrogen, or linear or branched lower alkyl;
- R5 is independently linear or branched, substituted or unsubstituted, saturated or unsaturated alkyl;
- R6 is hydrogen;
- saturated or unsaturated alkyl, aryl or alkylaryl having from 1 to 20 carbon atoms;
- or —(R2)rO((CR3R4)aO)s—R5;
- R7 is independently a bond, or linear or branched, substituted or unsubstituted alkyl, alkenyl or alkynyl having from 1 to 20 carbon atoms, and when substituted, the substituent can be, but is not limited to, —X, —CX3, —CHX2, —CH2X, —NHR9, or —NHC(O)R10;
- R8 is independently a bond or linear or branched, substituted or unsubstituted alkyl, alkenyl or alkynyl having from 1 to 20 carbon atoms, and when substituted, the substituent can be, but is not limited to, —X, —CX3, —CHX2, —CH2X, —NHR9, or —NHC(O)R10;
- R9 is a linear or branched, substituted or unsubstituted, saturated or unsaturated alkyl, aryl or alkylaryl group or an amino protecting group;
- R10 is a linear or branched alkyl, aryl or alkylaryl group;
- P is an —OH protecting group;
- X is a halogen;
- Y is —)— or —NH—;
- each a is independently 1 to 4;
- each b is independently zero or one;
- each r is independently 1 to 4;
- and each s is independently 1 to 5000.
26 more elements
Dependencies are inferred from the claim text.