Manage your formulary budget
Find generic entry opportunities
Deep knowledge on
small-molecule drugs and
the 110,000 global patents
Proactively manage your pharmacy inventory
Drug patents …
… from Kazakhstan to Kalamazoo
Anticipate generic drug launch
Upgrade to enjoy subscriber-only features like email alerts and data export. See the Plans and Pricing
|Title:||Method and compositions for the synthesis of BCH-189 and related compounds|
|Abstract:||The present invention relates to a method of preparing BCH-189 and various analogs of BCH-189 from inexpensive precursors with the option of introducing functionality as needed. This synthetic route allows the stereoselective preparation of the biologically active isomer of these compounds, .beta.-BCH-189 and related compounds. Furthermore, the steochemistry at the nucleoside 4' position can be controlled to produce enantiomerically-enriched .beta.-BCH-189 and its analogs.|
|Inventor(s):||Liotta; Dennis C. (Stone Mountain, GA), Choi; Woo-Baeg (Atlanta, GA)|
|Assignee:||Emory University (Atlanta, GA)|
|Filing Date:||Feb 01, 1990|
|Claims:||1. A method of preparing a composition comprising predominantly the .beta.-isomer of a 1,3-oxathiolane of the structure: ##STR8## wherein R' is an acyl group, and wherein R is an oxygen-protecting group with silylated cytosine in the presence of SnCl.sub.4. |
2. The method of claim 1, wherein R is selected from the group consisting of alkyl, silyl, and acyl.
3. The method of claim 1, further comprising the step of reacting a glycoaldehyde having the formula OHCCH.sub.2 OR, wherein R is a protecting group with thioglycolic acid to produce a 5-oxo-1,3-oxathiolane.
4. The method of claim 3 further comprising:
(i) reducing the oxo group in 5-oxo-1,3-oxathiolane to an alcohol; and
(ii) acylating the alcohol.
5. The method of claim 4, wherein the reducing agent is selected from the group consisting of diisobutylaluminum hydride, sodium bis(2-methoxyethoxy)aluminum hydride, and NaBH.sub.4.
6. The method of claim 1, further comprising replacing R with hydrogen.
7. The method of claim 6, wherein R is an acyl group, and wherein the acyl group is removed with sodium methoxide.
8. The method of claim 1, wherein the composition consists essentially of the .beta.-isomer of 2',3'-dideoxy-3'-thiacytidine.
9. The method of claim 1, wherein R is a silyl group, and wherein the silyl group is removed with (n--C.sub.4 H.sub.9).sub.4 NF.
10. The method of claim 2, wherein the silyl group is t-butyldiphenylsilyl.
11. The method of claim 2, wherein the silyl group has the formula ##STR9## wherein R.sub.1, R.sub.2, and R.sub.3 are independently C.sub.1 to C.sub.5 alkyl or phenyl.
Drugs may be covered by multiple patents or regulatory protections. All trademarks and applicant names are the property of their respective owners or licensors. Although great care is taken in the proper and correct provision of this service, thinkBiotech LLC does not accept any responsibility for possible consequences of errors or omissions in the provided data. The data presented herein is for information purposes only. There is no warranty that the data contained herein is error free. thinkBiotech performs no independent verifification of facts as provided by public sources nor are attempts made to provide legal or investing advice. Any reliance on data provided herein is done solely at the discretion of the user. Users of this service are advised to seek professional advice and independent confirmation before considering acting on any of the provided information. thinkBiotech LLC reserves the right to amend, extend or withdraw any part or all of the offered service without notice.