IP Library › Granted Patent US 9,290,492
Granted Patent B2
US 9,290,492 · App. 14/115,335 · Granted Mar 22, 2016

Solid forms of antibiotics

Inventors: Hugo Morales Rojas (Morelos, MX); Jorge Guillermo Domínguez Chávez (Morelos, MX); Dea Herrera Ruiz (Morelos, MX); Herbert Höpfl (Morelos, MX); Juan Manuel Martínez Alejo (Morelos, MX); Juan Pablo Senosiain Peláez (Mexico City, MX)
Assignee: Laboratorios Senosiain S.A. de C.V.
C07D471/04C07D215/56
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Quick Facts
Patent No.
US 9,290,492
App. No.
14/115,335
Granted
Mar 22, 2016
Kind
B2
Abstract

The invention relates to novel solid forms of fluoroquinolones, in particular to complex co-crystals and to solvates, hydrates and polymorphs thereof. These substances can be used to prepare a pharmaceutical composition containing same as an active ingredient, which can be used as an antibiotic. The compounds have a storage stability that is constant and above that of the salts or hydrates thereof.

Claims (32)

1. A moxifloxacin co-crystal of formula:

Wherein:

Y is selected from the group consisting of: 3-hydroxybenzoic acid, 4-hydroxybenzoic acid, 2,4-dihydroxybenzoic acid, 2,5-dihydroxybenzoic acid, 3,4-dihydroxybenzoic acid, 3,5-dihydroxybenzoic acid, glycolic acid, DL-malic acid, 4-hydroxybenzamide, catechol, 4-aminobenzoic acid, resorcinol and 4-hydroxybenzyl alcohol; or a solvate or a hydrate thereof.

2. A co-crystal in accordance with claim 1 , wherein Y is 4-hydroxybenzoic acid; or a solvate or a hydrate thereof.

3. A co-crystal in accordance with claim 1 , wherein Y is 2,5-dihydroxybenzoic acid; or a solvate or a hydrate thereof.

4. A co-crystal in accordance with claim 1 , wherein Y is 3-hydroxybenzoic acid; a solvate or a hydrate thereof.

5. A co-crystal in accordance with claim 1 , wherein Y is 2,4-dihydroxybenzoic acid; or a solvate or a hydrate thereof.

6. A co-crystal in accordance with claim 1 , wherein Y is 3,4-dihydroxybenzoic acid; or a solvate or a hydrate thereof.

7. A co-crystal in accordance with claim 1 , wherein Y is 3,5-dihydroxybenzoic acid; or a solvate or a hydrate thereof.

8. A co-crystal in accordance with claim 1 , wherein Y is catechol; or a solvate or a hydrate thereof.

9. A co-crystal in accordance with claim 1 , wherein Y is resorcinol; or a solvate or a hydrate thereof.

10. A co-crystal in accordance with claim 1 , wherein Y is glycolic acid; or a solvate or a hydrate thereof.

11. A co-crystal in accordance with claim 1 , wherein Y is DL-malic acid; or a solvate or a hydrate thereof.

12. A co-crystal in accordance with claim 1 , wherein Y is 4-hydroxybenzamide; or a solvate or a hydrate thereof.

13. A co-crystal in accordance with claim 1 , wherein Y is 4-aminobenzoic acid; or a solvate or a hydrate thereof.

14. A co-crystal in accordance with claim 1 , wherein Y is 4-hydroxybenzyl alcohol; or a solvate or a hydrate thereof.

15. A ciprofloxacin co-crystal of formula:

wherein:

Y is selected from the group consisting of: 3-hydroxybenzoic acid, 4-hydroxybenzoic acid, 2,5-dihydroxybenzoic acid, 3,4-dihydroxybenzoic acid, 3,5-dihydroxybenzoic acid, 2,4-dihydroxybenzoic acid, 2,3-dihydroxybenzoic acid, catechol, resorcinol and hydroquinone;

or a solvate or a hydrate thereof.

16. A co-crystal in accordance with claim 15 , wherein Y is 3-hydroxybenzoic acid; or a solvate or a hydrate thereof.

17. A co-crystal in accordance with claim 15 , wherein Y is 4-hydroxybenzoic acid; or a solvate or a hydrate thereof.

18. A co-crystal in accordance with claim 15 , wherein Y is 2,4-dihydroxybenzoic acid; or a solvate or a hydrate thereof.

19. A co-crystal in accordance with claim 15 , wherein Y is 3,4-dihydroxybenzoic acid; or a solvate or a hydrate thereof.

20. A co-crystal in accordance with claim 15 , wherein Y is 2,5-dihydroxybenzoic acid; or a solvate or a hydrate thereof.

21. A co-crystal in accordance with claim 15 , wherein Y is 2,3-dihydroxybenzoic acid; or a solvate or a hydrate thereof.

22. A co-crystal in accordance with claim 15 , wherein Y is 3,5-dihydroxybenzoic acid; or a solvate or a hydrate thereof.

23. A co-crystal in accordance with claim 15 , wherein Y is catechol; or a solvate or a hydrate thereof.

24. A co-crystal in accordance with claim 15 , wherein Y is resorcinol; or a solvate or a hydrate thereof.

25. A co-crystal in accordance with claim 15 , wherein Y is hydroquinone; or a solvate or a hydrate thereof.

26. A method for treating a bacterial infection comprising administering to a patient an effective amount of the moxifloxacin co-crystal of claim 1 .

27. A method for treating a bacterial infection comprising administering to a patient an effective amount of the ciprofloxacin co-crystal of claim 15 .

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 24, 2014
From: MORALES ROJAS, HUGO; HERRERA RUIZ, DEA; MARTINEZ ALEJO, JUAN MANUEL; DOMINGUEZ CHAVEZ, JORGE GUILLERMO; HOPFL, HERBERT; SENOSIAIN PELAEZ, JUAN PABLO
To: LABORATORIOS SENOSIAIN S.A. DE C.V.
Reel/Frame 034248/0668 →
Priority Claims (1)
MX MX/a/2011/004759 · May 4, 2011 · national
Continuity (1)
Related Publication 20140088116A1 · Mar 27, 2014