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US 8,273,790 B2Granted
Exo-selective synthesis of himbacine analogs
AssigneeSchering Corporation
InventorsTiruvettipuram K. Thiruvengadam, Anantha Sudhakar, Ngiap Kie Lim, Daw-Iong Kwok, George G. Wu, Tao Wang, Mingsheng Huang, Michael D. Green
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Abstract
This application discloses a novel process for the synthesis of himbacine analogs, as well as the compounds produced thereby. The synthesis proceeds by alternative routes including the cyclic ketal amide route, the chiral carbamate amide route, and the chiral carbamate ester route. The compounds produced thereby are useful as thrombin receptor antagonists. The chemistry disclosed herein is exemplified in the following synthesis sequence:
Claims4
A process of preparing a compound of the formula
- comprising:
- converting Compound 9:
- to Compound 10:
- and converting Compound 10 to Compound 8
- wherein R15 and R16 are each independently selected from the group consisting of H, alkyl, cycloalkyl, aryl, alkylaryl, arylalkyl, and heteroaryl groups or, when taken together with the nitrogen to which they are attached, may form a 3- to 6-membered heterocyclic ring containing 1 to 3 heteroatoms.
2 more elements
Dependencies are inferred from the claim text.