Solid phase synthesis supports and methods
Assignee3M Innovative Properties Company
InventorsJerald K. Rasmussen, Larry R. Krepski
Life of this patent
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Abstract
Functionalized supports and methods for solid phase synthesis. Preferably, the functionalized support is azlactone-functionalized.
Claims66
A method of solid phase synthesis, the method comprising:
- providing an azlactone-functionalized support;
- reacting the azlactone-functionalized support with a linker molecule to form a linker-functionalized support having a linker attached to the azlactone-functionalized support;
- and
- reacting the linker-functionalized support with an organic molecule to form a covalent bond between the linker and the organic molecule;
- and
- conducting one or more reactions on the covalently bound organic molecule to produce a derivatized organic molecule.
A method of solid phase synthesis, the method comprising:
- providing an amine-modified-azlactone-functionalized support;
- reacting the amine-modified-azlactone-functionalized support with a linker molecule to form a linker-functionalized support having a linker attached to the amine-modified-azlactone-functionalized support;
- and
- conducting one or more reactions on the linker-functionalized support.
A method of solid phase synthesis, the method comprising:
- providing a linker-functionalized support having the formula:
- SS-[NH—(C(R1)(R2))p—C(R3)(R4)(OR7)]m
- wherein:
- SS represents a support material;
- NH—(C(R1)(R2))p—C(R3)(R4)(OR7) represents a linker, wherein R1, R2, R3, and R4 are each independently hydrogen or an organic group with the proviso that at least one of R3 and R4 is an aromatic group, R7 is hydrogen, a protecting group, or an organic group capable of being derivatized, and p is at least 1;
- and
- m is 1 to the resin capacity of the support material;
- and
- conducting one or more reactions on the linker-functionalized support.
A method of solid phase synthesis, the method comprising:
- providing an azlactone-functionalized support having a linker attached thereto, which has the formula:
- SS-[C(O)—NH—C(R5)(R6)—(CH2)n—C(O)—NH—(C(R1)(R2))p—C(R3)(R4)(OR7)]m
- wherein:
- SS represents a support material;
- C(O)—NH—C(R5)(R6)—(CH2)n—C(O) is derived from an azlactone group, wherein R5 and R6 are each independently an organic group and n is 0 to 1;
- NH—(C(R1)(R2))p—C(R3)(R4)(OR7) represents the linker, wherein R1, R2, R3, and R4 are each independently hydrogen or an organic group with the proviso that at least one of R3 and R4 is an aromatic group, R7 is hydrogen, a protecting group, or an organic group capable of being derivatized, and p is at least 1;
- and
- m is 1 to the resin capacity of the support material;
- and
- conducting one or more reactions on the linker-functionalized support.
A method of solid phase synthesis, the method comprising:
- providing an azlactone-functionalized support having a linker attached thereto, which has the formula:
- SS-[C(O)—NH—C(R5)(R6)—(CH2)n—C(O)—NH—(R8)—NH—C(O)—R9]m
- wherein:
- SS represents a support material;
- C(O)—NH—C(R5)(R6)—(CH2)n—C(O) is derived from an azlactone group, wherein R5 and R6 are each independently an organic group and n is 0 to 1;
- NH—(R8)—NH is derived from a diamine, wherein R8 is an organic connecting group;
- C(O)—R9 represents the linker, wherein R9 is an organic group;
- and
- m is 1 to the resin capacity of the support material;
- and
- conducting one or more reactions on the linker-functionalized support.
A method of solid phase synthesis, the method comprising:
- providing an azlactone-functionalized support having a linker attached thereto, which has the formula:
- SS-[C(O)—NH—C(R5)(R6)—(CH2)n—C(O)—NH—(C(R1)(R2))p—C(R3)(R4)(OR7)]m
- wherein:
- SS represents a support material;
- C(O)—NH—C(R5)(R6)—(CH2)n—C(O) is derived from an azlactone group, wherein R5 and R are each independently an organic group and n is 0 to 1;
- NH—(C(R1)(R2))p—C(R3)(R4)(OR7) represents the linker, wherein R1, R2, R3, and R are each independently hydrogen or an organic group with the proviso that at least one of R3 and R4 is an aromatic group, R7 is hydrogen, a protecting group, or an organic group capable of being derivatized, and p is at least 1;
- and
- m is 1 to the resin capacity of the support material;
- reacting the linker with an organic molecule to form a covalent bond between the linker and the organic molecule;
- conducting one or more reactions on the covalently bound organic molecule to produce a derivatized organic molecule;
- and
- cleaving the derivatized molecule from the azlactone-functionalized support having a linker attached thereto.
A method of solid phase synthesis, the method comprising:
- providing a linker-functionalized support having the formula:
- SS-[C(O)—NH—C(R5)(R6)—(CH2)n—C(O)—NH—(R8)—NHC(O)—R9]m
- wherein:
- SS represents a support material;
- C(O)—NH—C(R5)(R6)—(CH2)n—C(O) is derived from an azlactone group, wherein R5 and R6 are each independently an organic group and n is 0 to 1;
- NH—(R8)—NH is derived from a diamine, wherein R8 is an organic connecting group;
- C(O)—R9 represents the linker, wherein R9 is an organic group;
- and
- m is 1 to the resin capacity of the support material;
- reacting the linker with an organic molecule so as to form a covalent bond between the linker and the organic molecule;
- conducting one or more reactions on the covalently bound organic molecule to produce a derivatized organic molecule;
- and
- cleaving the derivatized molecule from the azlactone-functionalized support having a linker attached thereto.
A functionalized support material having the formula:
- SS-[NH—(C(R1)(R2))p—C(R3)(R4)(OR7)]m
- wherein:
- SS represents a support material;
- R1, R2, R3, and R4 are each independently hydrogen or an organic group with the proviso that at least one of R3 and R4 is an aromatic group;
- R7 is hydrogen or an organic group;
- p is at least 1;
- and
- m is 1 to the resin capacity of the support material.
A functionalized support having the following formula:
- SS-[C(O)—NH—C(R5)(R6)—(CH2)n—C(O)—NH—(C(R1)(R2))p—C(R3)(R4)(OR7)]m
- wherein:
- SS represents a support material;
- R1, R2, R3, and R4 are each independently hydrogen or an organic group with the proviso that at least one of R3 and R4 is an aromatic group;
- R7 is hydrogen or an organic group;
- R5 and R6 are each independently an organic group;
- n is 0 to 1;
- p is at least 1;
- and
- m is 1 to the resin capacity of the support material.
A functionalized support having the following formula:
- S S-[C(O)—NH—C(R5)(R6)—(CH2)n—C(O)—NH—(R8)—NH—C(O)—R9]m
- wherein:
- SS represents a support material;
- R5, R6, and R9 are each independently an organic group;
- R8 is an organic connecting group;
- n is 0 to 1;
- and
- m is 1 to the resin capacity of the support material.
A functionalized support material having the formula:
- SS-[NH—(C(R1)(R2))p—C(R3)(R4)(OR7)]m
- wherein:
- SS represents a support material;
- R1, R2, R3, and R4 are each independently hydrogen, a (C1-C14)alkyl group, a (C3-C14)cycloalkyl group, or a (C5-C12)aryl group, with the proviso that at least one of R3 and R4 is a (C5-C 12)aryl group;
- R7 is hydrogen or an organic group;
- p is 1 to 20;
- and
- m is 1 to the resin capacity of the support material.
A functionalized support having the following formula:
- SS-[C(O)—NH—C(R5)(R6)—(CH2)n—C(O)—NH—(C(R1)(R2))n—C(R3)(R4)(OR7)]m
- wherein:
- SS represents a support material;
- R1, R2, R3, and R4 are each independently hydrogen, a (C1-C14)alkyl group, a (C3-C14)cycloalkyl group, or a (C5-C12)aryl group, with the proviso that at least one of R3 and R4 is a (C5-C12)aryl group;
- R7 is hydrogen or an organic group;
- R5 and R6 are each independently a (C1-C14)alkyl group, a (C3-C14)cycloalkyl group, or a (C5-C12)aryl group;
- n is 0 to 1;
- p is 1 to 20;
- and
- m is 1 to the resin capacity of the support material.
A functionalized support having the following formula:
- SS-[C(O)—NH—C(R5)(R6)—(CH2)n—C(O)—NH—(R8)—NH—C(O)—R9]m
- wherein:
- SS represents a support material;
- R5 and R6 are each independently a (C1-C14)alkyl group, a (C3-C14)cycloalkyl group, or a (C5-C12)aryl group;
- R9 is an organic group;
- R8 is a (C1-C1000)alkylene group;
- n is 0 to 1;
- and
- m is 1 to the resin capacity of the support material.
Dependencies are inferred from the claim text.