Synthesis of N-substituted oligomers
US5877278A · kind A · utility
Assignee
Inventors
Key dates
| Filing date | Jun 7, 1995 |
| Grant date | Mar 2, 1999 |
| Priority date | — |
| Expiry date | Jun 7, 2015 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC40B40/10
- WIPO fieldPharmaceuticals
- WIPO sectorChemistry
Abstract
A solid-phase method for the synthesis of N-substituted oligomers, such as poly (N-substituted glycines) (referred to herein as poly NSGs) is used to obtain oligomers, such as poly NSGs of potential therapeutic interest which poly NSGs can have a wide variety of side-chain substituents. Each N-substituted glycine monomer is assembled from two "sub-monomers" directly on the solid support. Each cycle of monomer addition consists of two steps: (1) acylation of a secondary amine bound to the support with an acylating agent comprising a leaving group capable of nucleophilic displacement by --NH.sub.2, such as a haloacetic acid, and (2) introduction of the side-chain by nucleophilic displacement of the leaving group, such as halogen (as a solid support-bound .alpha.-haloacetamide) with a sufficient amount of a second sub-monomer comprising an --NH.sub.2 group, such as a primary amine, alkoxyamine, semicarbazide, acyl hydrazide, carbazate or the like. Repetition of the two step cycle of acylation and displacement gives the desired oligomers. The efficient synthesis of a wide variety of oligomeric NSGs using automated synthesis technology of the present method makes these oligomers attract…
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.