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US 2002/0103387 A1Published application
Compounds which mimic the chemical and biological properties of discodermolide
AssigneeThe Trustees of the University of Pennsylvania
InventorsAmos B. Smith III, Thomas J. Beauchamp, Matthew J. LaMarche
Life of this patent
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Abstract
Compounds which mimic the chemical and/or biological activity of discodermolide are provided and intermediates useful in their preparation.
Claims22
A compound of formula:
- 143
- wherein:
- R1, R2, R7, and R8 are independently selected from hydrogen and C1-C10 alkyl;
- R3, R6, and R16 are independently selected from hydrogen and C1-C6 alkyl;
- R4 and R9 are selected from hydrogen and acid labile protecting groups;
- R40 is selected from OR25 and OC(═O)NH2;
- R25 is selected from hydrogen and an oxidatively labile protecting group;
- and
- J is selected from:
- 144
- alkaryl and alkheteroaryl wherein aryl and heteroaryl are optionally substituted and alk is optionally substituted with R32 or OR33;
- wherein:
- R32 is selected from hydrogen and C1-C6 alkyl;
- and
- R33 is selected from hydrogen and an acid labile hydroxy protecting group.
12 more elements
A compound having the following formula:
- 149
- wherein:
- R1, R2, R7, and R8 are independently hydrogen or C1-C10 alkyl;
- R3, R6, and R16 are independently hydrogen or C1-C6 alkyl;
- R4, and R9 are independently hydrogen or acid labile protecting groups;
- R40 is selected from OR25 and OC(═O)NH2;
- R25 is hydrogen or an oxidatively labile protecting group;
- and
- J is selected from:
- 150
- alkaryl and alkheteroaryl wherein aryl and heteroaryl are optionally substituted and alk is optionally substituted with R32 or OR33;
- wherein
- R32 is hydrogen or C1-C6 alkyl;
- and
- R33 is hydrogen or an acid labile hydroxy protecting group.
12 more elements
A compound having the formula:
- 151
- wherein
- R2, R7, and R8, are independently hydrogen or C1-C10 alkyl;
- R3, R6, and R16 are independently hydrogen or C1-C6 alkyl;
- R4, R9, and R33 are independently hydrogen or acid labile protecting groups;
- R4 and R9 are independently hydrogen or acid labile protecting hydroxl groups;
- R40 is selected from OR25 and OC(═O)NH2;
- R25 is hydrogen or an oxidatively labile protecting group;
- and
- J is selected from:
- 152
- alkaryl and alkheteroaryl wherein aryl and heteroaryl are optionally substituted and alk is optionally substituted with R32 or OR33;
- wherein
- R32 is hydrogen or C1-C6 alkyl;
- and
- R33 is hydrogen or an acid labile hydroxy protecting group.
13 more elements
A compound having the formula:
- 153
- wherein:
- R1, R2, R7, and R8 are independently hydrogen or C1-C10 alkyl;
- R3, R6, and R16 are independently hydrogen or C1-C6 alkyl;
- R4, R9 and R33 are independently hydrogen or acid labile protecting groups;
- R4, R9, are independently hydrogen or acid labile protecting hydroxl groups;
- R25 is hydrogen or an oxidatively labile protecting group;
- R40 is selected from OR25 and OC(═O)NH2;
- R′ is methyl or alkyl-R″;
- and
- R″ is C1-C10 alkoxy, hydroxy, or —C(O)CH3.
8 more elements
Dependencies are inferred from the claim text.