IP Library Granted Patent US 7,179,913
Granted Patent B2
US 7,179,913 · App. 10/532,397 · Granted Feb 20, 2007

Process for preparing a pharmaceutically active compound and for preparing its intermediate

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Quick Facts
Patent No.
US 7,179,913
App. No.
10/532,397
Granted
Feb 20, 2007
Kind
B2
Abstract

The invention discloses a method for preparing the intermediate 2-(2,3-dichlorophenyl)-2-(aminoguanidine)acetonitrile of formula (II), which comprises the reaction of 2,3-dichlorobenzoyl cyanide with aminoguanidine bicarbonate in non-aqueous medium in the presence of methanesulphonic acid, which produces good yields and short reaction times. Said intermediate is useful for preparing 3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazine of formula (I). The invention also relates to a method for preparing (I) with high purity

Claims (13)

1. A process for preparing the intermediate 2-(2,3-dichlorophenyl)-2-(aminoguanidine)acetonitrile, of formula (II):

which comprises the reaction of 2,3-dichlorobenzoyl cyanide with aminoguanidine bicarbonate, wherein it is carried out in non-aqueous medium in the presence of methanesulphonic acid as the only reaction medium; and wherein once the reaction has finished, the process further comprises the steps of:

i) adding water;

ii) adjusting the pH of the medium to a pH higher than the pKa of hydrogen cyanide; and

iii) isolating intermediate of formula (II).

2. Process according to claim 1 , wherein said reaction is carried out within a temperature range of 20 to 80° C.

3. Process according to claim 2 , wherein said reaction is carried out within a temperature range of 30 to 60° C.

4. Process according to claim 1 , wherein in ii), said adjustment of the pH is carried out by adding a sodium hydroxide solution.

5. Process for preparing the 3,5-diamino-6-(2,3-dichlorophenyl)- 1,2,4-triazine, of formula (I):

or a pharmaceutically acceptable salt thereof, which comprises the following steps:

a) preparation of the intermediate 2-(2,3-dichlorophenyl)-2-(aminoguanidine)acetonitrile, of formula (II), according to claim 1 ;

b) cyclisation of said intermediate of formula (II) in an aliphatic alcohol or in an aliphatic alcohol/water solution under reflux; and, if desired, obtaining a pharmaceutically acceptable salt thereof.

6. Process according to claim 5 , wherein said aliphatic alcohol used in step b) may be chosen from between ethanol and isopropanol.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 4, 2007
From: VITA CIENTIFICA, S.L.
To: INKE, S.A.
Reel/Frame 019773/0687 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 22, 2005
From: BESSA BELLMUNT, JORDI; DALMASES BARJOAN, PERE
To: VITA CIENTIFICA, S.L.
Reel/Frame 017166/0229 →