IP Library Granted Patent US 10,590,138
Granted Patent B2
US 10,590,138 · App. 16/288,812 · Granted Mar 17, 2020

Compositions comprising folic acid derivatives, their preparations and methods of use

Inventors: Gerald S. Jones, Jr. (Norwood, MA); Joseph P. St. Laurent (Lakeville, MA); Scott A. Goodrich (Stoughton, MA)
Assignee: Chemic Laboratories, Inc.
C07D475/04A61K31/519C07D487/14
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Quick Facts
Patent No.
US 10,590,138
App. No.
16/288,812
Granted
Mar 17, 2020
Kind
B2
Abstract

Described herein are methods for making folic acid derivatives, intermediates, pharmaceutical compositions and uses thereof.

Claims (19)

1. A method for making a compound of formula (V):

the method comprising cyclizing a compound of formula (II) to make a compound of formula (V):

wherein

R 1 and R 2 are each independently selected from H, OH, NH 2 , C 1-6 alkyl or aryl;

R 3 is H, C 1-6 alkyl or aryl;

Y is halo; and

X is Na, K, Mg or Ca.

2. The method of claim 1 , wherein the cyclization step is carried out in the presence of formic acid.

3. The method of claim 2 , further comprising a strong acid.

4. The method of claim 3 , wherein the strong acid is HCl.

5. The method of claim 2 , further comprising a solvent.

6. The method of claim 5 , wherein the solvent is an aqueous solvent.

7. The method of claim 1 , wherein R 1 is NH 2 .

8. The method of claim 1 , wherein R 2 is OH.

9. The method of claim 1 , wherein R 3 is H.

10. The method of claim 1 , wherein X is Ca.

11. The method of claim 1 , wherein Y is Cl.

12. The method of claim 1 , wherein R 1 is NH 2 , R 2 is OH, R 3 is H, X is Ca, and Y is Cl.

13. The method of claim 1 , the method further comprising a reduction of a compound of formula (V) to make a compound of formula (I):

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 17, 2022
From: JONES, GERALD S., JR.; ST. LAURENT, JOSEPH P.; GOODRICH, SCOTT A.
To: CHEMIC LABORATORIES, INC.
Reel/Frame 059035/0862 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 17, 2022
From: CHEMIC LABORATORIES, LLC
To: JSB PHARMA DEVELOPMENT, LLC
Reel/Frame 059036/0869 →
CHANGE OF NAME Recorded Feb 17, 2022
From: CHEMIC LABORATORIES, INC.
To: CHEMIC LABORATORIES, LLC
Reel/Frame 059258/0542 →
Continuity (5)
Division 15912070 · Mar 5, 2018
Continuation 15173164 · Jun 3, 2016
Continuation 14417504
Provisional Application 61676651 · Jul 27, 2012
Related Publication 20190315749A1 · Oct 17, 2019