Process for the preparation of highly pure Salcaprozic Acid and pharmaceutically acceptable salts thereof
AssigneeNavinta III Inc
InventorsPankaj Vasudev Parmar, Raja Jeyakumar John Muthiah, Vikas Kantilal Chauhan, Jagdish Kanjibhai Solanki
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Abstract
Processes that use novel reagents for the removal of colored impurity during the preparation of Salcaprozic Acid and pharmaceutically acceptable salts thereof. The processes include hydrolysis of 8-(2,4-dioxo-1,3-benzoxazin-3-yl)octanoic acid ethyl ester in the presence of or by contacting it with benzotriazole, hydrazine and/or sodium borohydride.
Claims20
A process for the preparation of Salcaprozic Acid or a pharmaceutically acceptable salt thereof, comprising:
- a. hydrolyzing a compound of formula II:
- wherein, R is straight or branched chain alkyl
- in the presence of benzotriazole, hydrazine, sodium borohydride or mixture thereof;
- and
- b. isolating Salcaprozic Acid, which is free from colored impurity.
A process for removing a colored impurity from a Salcaprozic Acid salt comprising treating a solution of the salt with benzotriazole, hydrazine, sodium borohydride or a mixture thereof.
A process for the preparation of Salcaprozic Acid or a pharmaceutically acceptable salt thereof, comprising:
- a. preparing 8-(2,4-dioxo-1,3-benzoxazin-3-yl)octanoic acid ethyl ester using 1,3-Benzoxazine-2,4-dione;
- b. contacting the 8-(2,4-dioxo-1,3-benzoxazin-3-yl)octanoic acid ethyl ester with about 1% to about 5% by weight of benzotriazole, hydrazine, Sodium borohydride or mixture thereof relative to the amount of 1,3-Benzoxazine-2,4-dione,
- c. adding aqueous metal hydroxide and stirring at an elevated temperature up to about 95° C.;
- d. cooling to 0-5° C. followed by adjusting pH to about 9 to about 10;
- e. washing the pH adjusted solution with an organic solvent to remove byproducts and impurities;
- and
- f. lowering pH of the washed solution to isolate a wet solid Salcaprozic Acid.
Dependencies are inferred from the claim text.