IP Library › Granted Patent US 10,866,219
Granted Patent B2
US 10,866,219 · App. 15/952,367 · Granted Dec 15, 2020

Method for detecting trifluridine- and/or tipiracil-related substance

Inventor: Yoshinori Tokimitsu (Tokushima, JP)
Assignee: TAIHO PHARMACEUTICAL CO., LTD.
G01N30/48A61K31/513A61K31/7072B01J20/283B01J20/287B01J20/28083C07H19/06G01N30/89B01J2220/54G01N30/34G01N2030/027G01N2030/486
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 10,866,219
App. No.
15/952,367
Granted
Dec 15, 2020
Kind
B2
Abstract

This invention provides a method that is capable of detecting a trifluridine-related substance and a tipiracil-related substance contained in a sample containing trifluridine or a salt thereof and tipiracil or a salt thereof using the same procedure. The method is for detecting a trifluridine-related substance or a tipiracil-related substance or both, the method comprising the step of subjecting a sample containing trifluridine or a salt thereof and tipiracil or a salt thereof to high-performance liquid chromatography using a mobile phase composed of an organic phase and an aqueous phase.

Claims (25)

1. A method for detecting a trifluridine-related substance or a tipiracil-related substance or both,

subjecting a sample containing trifluridine or a salt thereof and tipiracil or a salt thereof to high-performance liquid chromatography with a mobile phase comprising an organic phase and an aqueous phase; and

detecting at least one trifluridine-related or tipiracil-related substance contained in the sample,

wherein the at least one trifluridine-related or tipiracil-related substance includes 2′ deoxy-5-methoxycarbonyluridine being a related substance 4.

2. The method according to claim 1 , wherein

the detecting comprises detecting related substances 2 and 5 as well as the related substances 1, 3 and 4 contained in the sample, the related substance 1 is trifluorothymine, the related substance 2 is 2-iminopyrrolidine, the related substance 3 is 5-chloro-6-{(2-oxopyrrolidin-1-yl)methyl}pyrimidine-2,4-(1H,3H)-dione, and the related substance 5 is 5-carboxyuracil.

3. The method according to claim 2 , wherein the subjecting comprises performing the high-performance liquid chromatography such that the difference in retention time between the related substance 3 and trifluridine is 1.0 minute or longer.

4. The method according to claim 2 , wherein the percentage of the organic phase with respect to the entire mobile phase at retention times of the related substances 1 to 5, trifluridine, and tipiracil is within a range of 7 to 15% by volume.

5. The method according to claim 2 , wherein the organic phase comprises methanol.

6. The method according to claim 2 , wherein the aqueous phase comprises phosphoric acid or a salt thereof, or a mixture thereof.

7. The method according to claim 2 , wherein the difference between the maximum value and the minimum value of the percentage of the organic phase in the entire mobile phase at the retention times of the related substances 1, 3, and 4 and trifluridine is 5% by volume or less with respect to the entire mobile phase.

8. The method according to claim 2 , wherein the mobile phase has a pH of 2.0 to 5.0.

9. The method according to claim 3 , wherein the percentage of the organic phase with respect to the entire mobile phase at retention times of the related substances 1 to 5, trifluridine, and tipiracil is within a range of 7 to 15% by volume.

10. The method according to claim 3 , wherein the organic phase comprises methanol.

11. The method according to claim 4 , wherein the organic phase comprises methanol.

12. The method according to claim 3 , wherein the aqueous phase comprises phosphoric acid or a salt thereof, or a mixture thereof.

13. The method according to claim 4 , wherein the aqueous phase comprises phosphoric acid or a salt thereof, or a mixture thereof.

14. The method according to claim 3 , wherein the difference between the maximum value and the minimum value of the percentage of the organic phase in the entire mobile phase at the retention times of the related substances 1, 3, and 4 and trifluridine is 5% by volume or less with respect to the entire mobile phase.

15. The method according to claim 4 , wherein the difference between the maximum value and the minimum value of the percentage of the organic phase in the entire mobile phase at the retention times of the related substances 1, 3, and 4 and trifluridine is 5% by volume or less with respect to the entire mobile phase.

16. The method according to claim 3 , wherein the mobile phase has a pH of 2.0 to 5.0.

17. The method according to claim 4 , wherein the mobile phase has a pH of 2.0 to 5.0.

18. The method according to claim 1 , wherein the mobile phase has a pH of 2.6 to 2.8.

19. The method according to claim 1 , wherein the detecting comprises detecting at least one trifluridine-related substance and at least one tipiracil-related substance, and trifluorothymine is detected as a trifluridine-related substance, 5-chloro-6-{(2-oxopyrrolidin-1-yl)methyl}pyrimidine-2,4-(1H,3H)-dione is detected as a tipiracil-related substance, and 2′-deoxy-5-methoxycarbonyluridine is detected a trifluridine-related substance.

20. The method according to claim 1 , wherein the detecting further comprises detecting at least one selected from the group consisting of trifluorothymine being a related substance 1, and 5-chloro-6-{(2-oxopyrrolidin-1-yl)methyl}pyrimidine-2,4-(1H,3H)-dione being a related substance 3.

21. The method according to claim 1 , wherein the detecting further comprises detecting at least one selected from the group consisting of trifluorothymine being a related substance 1,2-iminopyrrolidine being a related substance 2,5-chloro-6-{(2-oxopyrrolidin-1-yl)methyl}pyrimidine-2,4-(1H,3H)-dione being a related substance 3, and 5-carboxyuracil being a related substance 5.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 18, 2018
From: TOKIMITSU, YOSHINORI
To: TAIHO PHARMACEUTICAL CO., LTD.
Reel/Frame 045848/0526 →
Priority Claims (1)
JP 2017-246043 · Dec 22, 2017 · national
Continuity (1)
Related Publication 20190195840A1 · Jun 27, 2019