Process for the preparation of roquinimex

• US 5,912,349 A
• Filed: 01/13/1998
• Issued: 06/15/1999
• Est. Priority Date: 01/31/1997
• Status: Expired due to Fees

• Current Assignee: Pharmacia & Upjohn Company (Pfizer Inc.)
• Original Assignee: Pharmacia & Upjohn Company (Pfizer Inc.)
• Inventors: Sih, John C.
• Primary Examiner(s): Morris, Patricia L.
• Application Number:
  US09/006,097
• Time in Patent Office: 518 Days
• Field of Search: 546/155
• US Class Current: 546/155
• CPC Class Codes: C07D 215/22 attached in position 2 or 4

Abstract

The present invention is an improved process to prepare roquinimex (IV) which comprises:

(1) contacting N-methyl-N-phenyl-α-carbomethoxyamide (V) with from about one to about two equivalents of base and

(2) contacting the mixture of step (1) with N-methylisatoic anhydride (I).

Claims

1. A process to prepare roquinimex (IV) which comprises:

(1) contacting N-methyl-N-phenyl-α

-carbomethoxyamide (V) with from about one to about two equivalents of base and

(2) contacting the mixture of step (1) with N-methylisatoic anhydride (I).

2. A process according to claim 1 where the base is present in an amount of about one equivalent.

3. A process according to claim 1 where the base is selected from the group consisting of alkoxides where the alkyl portion is C₁ -C₄ alkyl.

4. A process according to claim 3 where the base is sodium or potassium butoxide.

5. A process according to claim 1 where the process is performed in the presence of an aprotic solvent.

6. A process according to claim 5 where the aprotic solvent is selected from the group consisting of DMF, THF, glyme, dioxane and ether and mixtures thereof.