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US 6,870,058 B2Granted
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:
- 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 hydroxyl 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:
- 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;
- R33 is selected from hydrogen and an acid labile hydroxy protecting group;
- and
- R34 is selected from hydrogen and C1-C6 alkyl;
- with the proviso that when R1, R2, R6, R7, R8, and R32 are methyl;
- and R3 is hydrogen or methyl;
- and R4, R9, R16, R25, and R33 are hydrogen;
- and J is:
- R34 is other than hydrogen or methyl.
16 more elements
A compound having the following formula:
- 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 hydroxyl 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:
- 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.
10 more elements
A compound having the formula:
- 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 hydroxyl 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:
- 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.
10 more elements
A compound having the formula:
- 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 hydroxyl protecting 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.
6 more elements
A compound of formula:
- wherein:
- R3 and R16 are independently selected from hydrogen and C1-C6 alkyl.
Dependencies are inferred from the claim text.