Hydroxylated erythro-hydroxynonyladenines and related analogs
US5491146A · kind A · utility
Assignee
Inventor
Key dates
| Filing date | Sep 19, 1994 |
| Grant date | Feb 13, 1996 |
| Priority date | — |
| Expiry date | Sep 19, 2014 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07D473/00
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
This invention discloses various analogs of erythro-hydroxynonyladenine (EHNA) which have been modified by the addition of hydroxy groups or other moieties at the #8 or #9 carbon atoms of the side-chain portion of the molecule (i.e., the erythro-hydroxynonyl chain which is attached to the adenosine ring structure). It also discloses synthetic reagents and steps that can be used to create these and other analogs of EHNA which contain hydroxyl, halide, acid, ester, ether, amine, azide, or other moieties at such locations, or at other controllable locations such as the #5, #6, or #7 carbon atoms on the side-chain. Analogs containing such side-chain modifications can also be modified in the adenosine structure if desired. The hydroxylated analogs described herein have been shown to inhibit adenosine deaminase (ADA) at therapeutically useful levels. The relevant Ki values are in the range of 10.sup.-8 to 10.sup.-9, which is within a desired range of about 10.sup.-7 to about 10.sup.-10. EHNA analogs that have potencies within this range can effectively inhibit ADA activity on a reversible basis, without permanently poisoning the enzyme. It has also been discovered that some of these anal…
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.