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US 9,006,254 B2Granted
Immunomodulatory agent-polymeric compounds
AssigneeSelecta Biosciences, Inc.
InventorsCharles Zepp, Grayson B. Lipford, Yun Gao, Lloyd Johnston, Fen-ni Fu, Mark J. Keegan, Sam Baldwin
Life of this patent
Estimating the term…
Abstract
This invention relates to compositions, and related compounds and methods, of conjugates of immunomodulatory agents and polymers or unit(s) thereof. The conjugates may be contained within synthetic nanocarriers, and the immunomodulatory agents may be released from the synthetic nanocarriers in a pH sensitive manner.
Claims27
A compound that comprises a structure as in formula (II):
- wherein R1═H, OH, SH, NH2, or substituted or unsubstituted alkyl, alkoxy, alkylthio, or alkylamino;
- R2═H, alkyl, or substituted alkyl;
- Y═N or C;
- R3 is absent if Y═N;
- or is H, alkyl, substituted alkyl, or combined with R4 to form a carbocycle or heterocycle with the carbon atoms of the pyridine ring to which they are connected if Y═C;
- R4 is H, or substituted or unsubstituted alkyl, alkoxy, alkylthio, or alkylamino when not combined with R3 to form a carbocycle or heterocycle with the carbon atoms of the pyridine ring to which they are connected;
- or is combined with R3 to form a carbocycle or heterocycle with the carbon atoms of the pyridine ring to which they are connected;
- R5 is a polymer or unit thereof;
- X═C, N, O, or S;
- R6 and R7 are each independently absent, H, or substituted;
- and
- R9, R10, R11, and R12 are each independently H, a halogen, OH, thio, NH2, or substituted or unsubstituted alkyl, aryl, heterocyclic, alkoxy, aryloxy, alkylthio, arylthio, alkylamino, or arylamino.
9 more elements
A method for making a conjugate that comprises a structure as in formula (II):
- comprising:
- combining an alcohol, a catalyst, and a compound comprising a structure as in formula (IV):
- wherein R1═H, OH, SH, NH2, or substituted or unsubstituted alkyl, alkoxy, alkylthio, or alkylamino;
- R2═H, alkyl, or substituted alkyl;
- Y═N or C;
- R3 is absent if Y═N;
- or is H, alkyl, substituted alkyl, or combined with R4 to form a carbocycle or heterocycle with the carbon atoms of the pyridine ring to which they are connected if Y═C;
- R4 is H, or substituted or unsubstituted alkyl, alkoxy, alkylthio, or alkylamino when not combined with R3 to form a carbocycle or heterocycle with the carbon atoms of the pyridine ring to which they are connected;
- or is combined with R3 to form a carbocycle or heterocycle with the carbon atoms of the pyridine ring to which they are connected;
- R5 is a polymer or unit thereof;
- X is C, N, O, or S;
- R6 and R7 are each independently H or substituted;
- and
- R9, R10, R11, and R12 are each independently H, a halogen, OH, thio, NH2, or substituted or unsubstituted alkyl, aryl, heterocyclic, alkoxy, aryloxy, alkylthio, arylthio, alkylamino, or arylamino;
- and
- heating the alcohol, catalyst, and compound.
13 more elements
A method for making a conjugate that comprises a structure as in formula (VI):
- comprising:
- combining a catalyst, a diol having the formula (VII):
- HO-polymer-OH (VII),
- and a compound comprising a structure as in formula (IV):
- wherein R1═H, OH, SH, NH2, or substituted or unsubstituted alkyl, alkoxy, alkylthio, or alkylamino;
- R2═H, alkyl, or substituted alkyl;
- Y═N or C;
- R3 is absent if Y═N;
- or is H, alkyl, substituted alkyl, or combined with R4 to form a carbocycle or heterocycle with the carbon atoms of the pyridine ring to which they are connected if Y═C;
- R4 is H, or substituted or unsubstituted alkyl, alkoxy, alkylthio, or alkylamino when not combined with R3 to form a carbocycle or heterocycle with the carbon atoms of the pyridine ring to which they are connected;
- or is combined with R3 to form a carbocycle or heterocycle with the carbon atoms of the pyridine ring to which they are connected;
- X is C, N, O, or S;
- R6 and R7 are each independently H or substituted;
- and
- R9, R10, R11, and R12 are each independently H, a halogen, OH, thio, NH2, or substituted or unsubstituted alkyl, aryl, heterocyclic, alkoxy, aryloxy, alkylthio, arylthio, alkylamino, or arylamino;
- and
- heating the alcohol, catalyst, and compound
14 more elements
A compound that comprises a structure as in formula (VI):
- wherein R1═H, OH, SH, NH2, or substituted or unsubstituted alkyl, alkoxy, alkylthio, or alkylamino;
- R2═H, alkyl, or substituted alkyl;
- Y═N or C;
- R3 is absent if Y═N;
- or is H, alkyl, substituted alkyl, or combined with R4 to form a carbocycle or heterocycle with the carbon atoms of the pyridine ring to which they are connected if Y═C;
- R4 is H, or substituted or unsubstituted alkyl, alkoxy, alkylthio, or alkylamino when not combined with R3 to form a carbocycle or heterocycle with the carbon atoms of the pyridine ring to which they are connected;
- or is combined with R3 to form a carbocycle or heterocycle with the carbon atoms of the pyridine ring to which they are connected;
- X is C, N, O, or S;
- R6 and R7 are each independently H or substituted;
- and
- R9, R10, R11, and R12 are each independently H, a halogen, OH, thio, NH2, or substituted or unsubstituted alkyl, aryl, heterocyclic, alkoxy, aryloxy, alkylthio, arylthio, alkylamino, or arylamino.
8 more elements
A method for making a conjugate that comprises a structure as in formula (II):
- comprising:
- combining an alcohol and a compound comprising a structure as in formula (IV):
- wherein R1═H, OH, SH, NH2, or substituted or unsubstituted alkyl, alkoxy, alkylthio, or alkylamino;
- R2═H, alkyl, or substituted alkyl;
- Y═N or C;
- R3 is absent if Y═N;
- or is H, alkyl, substituted alkyl, or combined with R4 to form a carbocycle or heterocycle with the carbon atoms of the pyridine ring to which they are connected if Y═C;
- R4 is H, or substituted or unsubstituted alkyl, alkoxy, alkylthio, or alkylamino when not combined with R3 to form a carbocycle or heterocycle with the carbon atoms of the pyridine ring to which they are connected;
- or is combined with R3 to form a carbocycle or heterocycle with the carbon atoms of the pyridine ring to which they are connected;
- R5 is a polymer or unit thereof;
- X is C, N, O, or S;
- R6 and R7 are each independently H or substituted;
- and
- R9, R10, R11, and R12 are each independently H, a halogen, OH, thio, NH2, or substituted or unsubstituted alkyl, aryl, heterocyclic, alkoxy, aryloxy, alkylthio, arylthio, alkylamino, or arylamino;
- heating the alcohol and compound;
- and
- adding a catalyst.
14 more elements
A method for making a conjugate that comprises a structure as in formula (II):
- comprising:
- combining an alcohol, a catalyst, and a compound comprising a structure as in formula (IV):
- wherein R1═H, OH, SH, NH2, or substituted or unsubstituted alkyl, alkoxy, alkylthio, or alkylamino;
- R2═H, alkyl, or substituted alkyl;
- Y═N or C;
- R3 is absent if Y═N;
- or is H, alkyl, substituted alkyl, or combined with R4 to form a carbocycle or heterocycle with the carbon atoms of the pyridine ring to which they are connected if Y═C;
- R4 is H, or substituted or unsubstituted alkyl, alkoxy, alkylthio, or alkylamino when not combined with R3 to form a carbocycle or heterocycle with the carbon atoms of the pyridine ring to which they are connected;
- or is combined with R3 to form a carbocycle or heterocycle with the carbon atoms of the pyridine ring to which they are connected;
- R5 is a polymer or unit thereof;
- X is C, N, O, or S;
- R6 and R7 are each independently H or substituted;
- and
- R9, R10, R11, and R12 are each independently H, a halogen, OH, thio, NH2, or substituted or unsubstituted alkyl, aryl, heterocyclic, alkoxy, aryloxy, alkylthio, arylthio, alkylamino, or arylamino.
11 more elements
A method for making a conjugate that comprises a structure as in formula (VI):
- comprising:
- combining a diol having the formula (VII):
- HO-polymer-OH (VII),
- and a compound comprising a structure as in formula (IV):
- wherein R1═H, OH, SH, NH2, or substituted or unsubstituted alkyl, alkoxy, alkylthio, or alkylamino;
- R2═H, alkyl, or substituted alkyl;
- Y═N or C;
- R3 is absent if Y═N;
- or is H, alkyl, substituted alkyl, or combined with R4 to form a carbocycle or heterocycle with the carbon atoms of the pyridine ring to which they are connected if Y═C;
- R4 is H, or substituted or unsubstituted alkyl, alkoxy, alkylthio, or alkylamino when not combined with R3 to form a carbocycle or heterocycle with the carbon atoms of the pyridine ring to which they are connected;
- or is combined with R3 to form a carbocycle or heterocycle with the carbon atoms of the pyridine ring to which they are connected;
- R5 is a polymer or unit thereof;
- X is C, N, O, or S;
- R6 and R7 are each independently H or substituted;
- and
- R9, R10, R11, and R12 are each independently H, a halogen, OH, thio, NH2, or substituted or unsubstituted alkyl, aryl, heterocyclic, alkoxy, aryloxy, alkylthio, arylthio, alkylamino, or arylamino;
- heating the alcohol and compound;
- and
- adding a catalyst.
16 more elements
A method for making a conjugate that comprises a structure as in formula (VI):
- comprising:
- combining a catalyst, a diol having the formula (VII):
- HO-polymer-OH (VII),
- and a compound comprising a structure as in formula (IV):
- wherein R1═H, OH, SH, NH2, or substituted or unsubstituted alkyl, alkoxy, alkylthio, or alkylamino;
- R2═H, alkyl, or substituted alkyl;
- Y═N or C;
- R3 is absent if Y═N;
- or is H, alkyl, substituted alkyl, or combined with R4 to form a carbocycle or heterocycle with the carbon atoms of the pyridine ring to which they are connected if Y═C;
- R4 is H, or substituted or unsubstituted alkyl, alkoxy, alkylthio, or alkylamino when not combined with R3 to form a carbocycle or heterocycle with the carbon atoms of the pyridine ring to which they are connected;
- or is combined with R3 to form a carbocycle or heterocycle with the carbon atoms of the pyridine ring to which they are connected;
- R5 is a polymer or unit thereof;
- X is C, N, O, or S;
- R6 and R7 are each independently H or substituted;
- and
- R9, R10, R11, and R12 are each independently H, a halogen, OH, thio, NH2, or substituted or unsubstituted alkyl, aryl, heterocyclic, alkoxy, aryloxy, alkylthio, arylthio, alkylamino, or arylamino.
13 more elements
Dependencies are inferred from the claim text.