.

Pharmaceutical Business Intelligence

  • Anticipate P&T budget requirements
  • Evaluate market entry opportunities
  • Find generic sources and suppliers
  • Predict branded drug patent expiration

► Plans and Pricing

Upgrade to enjoy subscriber-only features like email alerts and data export. See the Plans and Pricing

DrugPatentWatch Database Preview

Details for Patent: 5,466,806

« Back to Dashboard

Details for Patent: 5,466,806

Title: Processes for preparing substituted 1,3-oxathiolanes with antiviral properties
Abstract:Disclosed are processes for preparing compounds of the formula (I) and pharmaceutically acceptable salts or esters thereof: ##STR1## wherein R.sub.2 is a purine or pyrimidine base or an analogue or derivative thereof; and Z is S, S.dbd.O or SO.sub.2. The invention also relates to intermediates of use in the preparation of these compounds.
Inventor(s): Belleau, deceased; Bernard (late of Westmont, CA), Mansour; Tarek (Montreal, CA), Tse; Allan (Ville St-Laurent, CA), Evans; Colleen A. (Montreal, CA), Jin; Haolun (Pierrefonds, CA), Zacharie; Boulos (Laval des Rapides, CA), Nguyen-Ba; Nghe (La Prairie, CA)
Assignee: Biochem Pharma Inc. (Laval, CA)
Filing Date:Mar 29, 1993
Application Number:08/040,163
Claims:1. A process for preparing a compound of formula (XIII): ##STR43## comprising the step of reacting a mercaptoacetaldehyde with a compound having the formula R.sub.w OCH.sub.2 CHO under neutral or basic conditions, wherein R.sub.w is hydrogen or a hydroxyl protecting group.

2. The process according to claim 1, wherein the hydroxyl of the compound of formula (XIII) is converted to a leaving group L to obtain a compound of formula (XIV): ##STR44## wherein R.sub.w is hydrogen or a hydroxy protecting group.

3. The process according to claim 2, wherein L is OR.sub.z, wherein R.sub.z is selected from the group consisting of hydrogen, a substituted or unsubstituted, saturated or unsaturated C.sub.1-6 alkyl group, a substituted or unsubstituted C.sub.1-6 aliphatic or phenyl acyl group, a substituted or unsubstituted, saturated or unsaturated alkoxycarbonyl group, a substituted or unsubstituted sulphonyl imidazolide, a substituted or unsubstituted carbonyl imidazolide, a substituted or unsubstituted aliphatic or phenyl amino carbonyl group, a substituted or unsubstituted alkyl imidate group, a substituted or unsubstituted, saturated or unsaturated phosphinoyl, a substituted or unsubstituted aliphatic or phenyl sulphonyl group.

4. The process according to claim 2, further comprising the step of reacting the compound of formula (XIV) with a silylated pyrimidine base or an analogue or derivative thereof R.sub.2, in the presence of a Lewis acid, to produce a compound of the formula (IX): ##STR45## wherein R.sub.w is hydrogen or a hydroxy protecting group; Z is S; and R.sub.2 is selected from the group consisting of: ##STR46## wherein: R.sub.3 and R.sub.4 are independently selected from the group consisting of hydrogen, hydroxyl, amino, substituted or unsubstituted C.sub.1-6 alkyl, or C.sub.2-6 alkenyl or C.sub.2-6 alkynyl, and substituted or unsubstituted C.sub.1-10 acyl or phenyl acyl; and

R.sub.5 and R.sub.6 are independently selected from the group consisting of hydrogen, halogen, hydroxyl, amino, cyano, carboxy, carbamoyl, alkoxycarbonyl, hydroxymethyl, trifluoromethyl, thioaryl, substituted or unsubstituted C.sub.1-6 alkyl or C.sub.2-6 alkenyl or C.sub.2-6 alkynyl, and substituted or unsubstituted C.sub.1-10 acyloxy.

5. The process according to claim 4, wherein R.sub.2 is selected from the group consisting of: ##STR47## wherein: each R.sub.11 is independently selected from hydrogen, acetyl, and C.sub.1-6 alkyl; and

R.sub.12 and R.sub.13 are independently selected from hydrogen, hydroxymethyl, trifluoromethyl, substituted or unsubstituted C.sub.1-6 alkyl or C.sub.2-6 alkenyl, bromine, chlorine, fluorine and iodine.

6. The process according to claim 4, wherein the sulfur of the compound of formula (IX) may optionally be oxidized to give a compound of formula (IX) wherein Z is S.dbd.O or SO.sub.2.

7. The process according to claim 1, wherein the mercaptoacetaldehyde is obtained from a mercaptoacetaldehyde dimer dissolved in an inert solvent.

8. The process according to claim 7, wherein the inert solvent is selected from the group consisting of pyridine, toluene and DMSO.
« Back to Dashboard

For more information try a trial or see the database preview and plans and pricing

How are People Using DrugPatentWatch?

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.

`abc