Cyclic polypeptides comprising a thioether linkage and methods for their preparation
US5817752A · kind A · utility
Assignee
Inventor
Key dates
| Filing date | Nov 12, 1996 |
| Grant date | Oct 6, 1998 |
| Priority date | — |
| Expiry date | Nov 12, 2016 |
Classification
- Technology area (CPC A)Human Necessities
- CPC primaryA61K38/00
- WIPO fieldPharmaceuticals
- WIPO sectorChemistry
Abstract
This invention relates generally to cyclic polypeptides comprising a thioether linkage and methods for their preparation. More particularly, this invention relates to halogenated polypeptides having at least one haloalanine-like amino acid, and methods for their preparation which involve converting the hydroxyl group (i.e., --OH) of a serine-like amino acid to a halo group (i.e., --X where X is Cl, Br, or I) with the aid of a phosphorus-based halogenation reagent such as a triphenylphosphine dihalide (i.e., (C.sub.6 H.sub.5).sub.3 PX.sub.2, wherein X is Cl, Br, or I), a triphenylphosphite dihalide (i.e., (C.sub.6 H.sub.5 O).sub.3 PX.sub.2, wherein X is Cl, Br, or I), or a mixture of triphenylphosphine or triphenylphosphite with a halohydrocarbon (i.e., "halo-conversion"). This invention also relates to cyclic polypeptides having at least one polypeptide loop comprising a thioether linkage, and methods for their preparation which employ halogenated polypeptides and which involve intramolecular alkylation of the thiol group of a cysteine-like amino acid by the halo group of a haloalanine-like amino acid under suitable basic conditions to form a thioether linkage (i.e., "cyclization")…
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.