IP Library Granted Patent US 11,369,587
Granted Patent B2
US 11,369,587 · App. 16/318,044 · Granted Jun 28, 2022

Injectable pharmaceutical composition of tecovirimat and preparation method thereof

Inventors: Wu Zhong (Beijing, CN); Meiyan Yang (Beijing, CN); Wei Gong (Beijing, CN); Yuli Wang (Beijing, CN); Chunsheng Gao (Beijing, CN); Xinbo Zhou (Beijing, CN); Song Li (Beijing, CN)
Assignee: Institute of Pharmacology and Toxicology Academy of Military Medical Sciences PLA China
A61K31/403A61K9/19A61K47/26A61K47/40
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Quick Facts
Patent No.
US 11,369,587
App. No.
16/318,044
Granted
Jun 28, 2022
Kind
B2
Abstract

The present invention relates to a pharmaceutical composition of Tecovirimat for injection, comprising Tecovirimat as an active ingredient, cyclodextrin and an additive. The present invention also relates to a method for preparing the pharmaceutical composition. The composition improves the solubility of Tecovirimat in water by using cyclodextrin and meglumine in combination, as compared with the solubility of Tecovirimat in water by using cyclodextrin or meglumine alone.

Claims (22)

1. A pharmaceutical composition of Tecovirimat for injection, comprising Tecovirimat as an active ingredient, a cyclodextrin and an additive, wherein said additive is meglumine.

2. The pharmaceutical composition according to claim 1 , wherein said cyclodextrin is selected from the group consisting of α-cyclodextrin, β-cyclodextrin, γ-cyclodextrin, a hydroxypropyl-β-cyclodextrin, dimethyl-β-cyclodextrin, 2-hydroxyethyl-β-cyclodextrin, and trimethyl-β-cyclodextrin.

3. The pharmaceutical composition according to claim 1 , wherein said cyclodextrin and Tecovirimat have a weight ratio of 4-10:1.

4. The pharmaceutical composition according to claim 1 , wherein said additive and Tecovirimat have a weight ratio of 0.5-5:1.

5. The pharmaceutical composition according to claim 1 , wherein said additive and cyclodextrin have a weight ratio of 1:1-5.

6. The pharmaceutical composition according to claim 1 , wherein said pharmaceutical composition further comprises one or more components selected from the group consisting of water, glucose, and physiological saline.

7. The pharmaceutical composition according to claim 1 , wherein said pharmaceutical composition is a liquid.

8. The pharmaceutical composition according to claim 2 , wherein said cyclodextrin is the hydroxypropyl-β-cyclodextrin, and wherein an amount of said hydroxypropyl-β-cyclodextrin is 10% (w/v)-40% (w/v).

9. The pharmaceutical composition according to claim 2 , wherein said cyclodextrin is selected from the group consisting of dimethyl-β-cyclodextrin, 2-hydroxyethyl-β-cyclodextrin, 2-hydroxypropyl-β-cyclodextrin, 3-hydroxypropyl-β-cyclodextrin, and trimethyl-β-cyclodextrin.

10. The pharmaceutical composition according to claim 2 , wherein said cyclodextrin is selected from the group consisting of β-cyclodextrin, dimethyl-β-cyclodextrin, 2-hydroxyethyl-β-cyclodextrin, 2-hydroxypropyl-β-cyclodextrin, 3-hydroxypropyl-β-cyclodextrin, and trimethyl-β-cyclodextrin.

11. The pharmaceutical composition according to claim 2 , wherein said cyclodextrin is the hydroxypropyl-β-cyclodextrin, wherein the hydroxypropyl-β-cyclodextrin is selected from the group consisting of 2-hydroxypropyl-β-cyclodextrin and 3-hydroxypropyl-β-cyclodextrin.

12. The pharmaceutical composition according to claim 11 , wherein said cyclodextrin is 2-hydroxypropyl-β-cyclodextrin.

13. The pharmaceutical composition according to claim 3 , wherein said cyclodextrin and Tecovirimat have a weight ratio of 5-8:1.

14. The pharmaceutical composition according to claim 4 , wherein said additive and Tecovirimat have a weight ratio of 1-4:1.

15. The pharmaceutical composition according to claim 5 , wherein said additive and cyclodextrin have a weight ratio of 1:2-4.

16. The pharmaceutical composition according to claim 7 , wherein Tecovirimat has a concentration of 15-80 mg/ml.

17. A method for preparing the pharmaceutical composition according to claim 1 , comprising the following steps:

a) dissolving an additive and cyclodextrin in a desired volume of water, and mixing well, wherein the additive is meglumine;

b) adding Tecovirimat, and stirring well; and

c) carrying out sterilization.

18. The method for preparing the pharmaceutical composition according to claim 17 , wherein said drying is freeze-drying.

19. A method for treating smallpox, comprising administering to a subject in need thereof a therapeutically and/or prophylactically effective amount of the pharmaceutical composition according to claim 1 .

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 16, 2025
From: ACADEMY OF MILITARY MEDICAL SCIENCES
To: CHINA NATIONAL BIOTEC GROUP CO., LTD.
Reel/Frame 071137/0255 →
CONFIRMATORY ASSIGNMENT AND CLARIFICATION OF ASSIGNEE'S NAME Recorded Mar 19, 2025
From: ZHONG, WU; YANG, MEIYAN; GONG, WEI; WANG, YULI; GAO, CHUNSHENG; ZHOU, XINBO; LI, SON
To: INSTITUTE OF PHARMACOLOGY AND TOXICOLOGY ACADEMY OF MILITARY MEDICAL SCIENCES P.L.A. CHINA
Reel/Frame 070557/0407 →
CHANGE OF NAME Recorded Mar 19, 2025
From: INSTITUTE OF PHARMACOLOGY AND TOXICOLOGY ACADEMY OF MILITARY MEDICAL SCIENCES P.L.A. CHINA
To: ACADEMY OF MILITARY MEDICAL SCIENCES
Reel/Frame 070564/0189 →
CONFIRMATORY ASSIGNMENT Recorded May 10, 2019
From: ZHONG, WU; YANG, MEIYAN; GONG, WEI; WANG, YULI; GAO, CHUNSHENG; ZHOU, XINBO; LI, SONG
To: INSTITUTE OF PHARMACOLOGY AND TOXICOLOGY ACADEMY OF MILITARY MEDICAL SCIENCES P.L.A.
Reel/Frame 049149/0159 →
Priority Claims (1)
CN 201610559479.1 · Jul 15, 2016 · national
Continuity (1)
Related Publication 20190336479A1 · Nov 7, 2019