Crystalline form of omeprazole

• US 6,150,380 A
• Filed: 12/10/1998
• Issued: 11/21/2000
• Est. Priority Date: 11/10/1998
• Status: Expired due to Term

• Current Assignee: Astrazeneca AB (Astrazeneca PLC)
• Original Assignee: Astra AB (Astrazeneca PLC)
• Inventors: Lovqvist, Karin, Ymen, Ingvar, Noreland, David, Sunden, Gunnel
• Primary Examiner(s): FAN, JANE T
• Application Number:
  US09/202,251
• Time in Patent Office: 712 Days
• Field of Search: 514/338, 546/273.7
• US Class Current: 514/338
• CPC Class Codes: A61K 31/4439 containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole nicotine A61K31/465
• CPC Class Codes: A61K 31/454 containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
• CPC Class Codes: A61P 1/00 Drugs for disorders of the alimentary tract or the digestive system
• CPC Class Codes: A61P 1/04 for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
• CPC Class Codes: C07D 401/12 linked by a chain containing hetero atoms as chain links

Abstract

The present invention relates to a novel crystalline form of 5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole, known under the generic name omeprazole. Further, the present invention also relates to the use of the novel crystalline form of 5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole for the treatment of gastrointestinal disorders, pharmaceutical compositions containing it as well as processes for the preparation of the novel crystalline form of 5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole.

Claims

1. Omeprazole form A which is a non-salt racemate, wherein omeprazole form A provides an X-ray powder diffraction pattern exhibiting substantially the following d-values:

space="preserve" listing-type="tabular">______________________________________ Form A Form A d-value Relative D-value Relative (Å

) intensity (Å

) intensity ______________________________________ 9.5 vs 3.71 s 7.9 s 3.59 m 7.4 w 3.48 m 7.2 vs 3.45 s 6.0 m 3.31 w 5.6 s 3.22 s 5.2 s 3.17 m 5.1 s 3.11 w 4.89 w 3.04 w 4.64 m 3.00 w 4.60 m 2.91 w 4.53 w 2.86 w 4.49 m 2.85 w 4.31 m 2.75 w 4.19 w 2.67 w 4.15 w 2.45 w 3.95 w 2.41 w. ______________________________________

2. Omeprazole form A, according to claim 1, wherein omeprazole form A is defined by a triclinic unit cell with parameters a=10.410(4)Å

, b=10.468(3)Å

, c=9.729(4)Å

, α

=111.51(3)°

, β

=116.78(3)°

, γ

=90.77(3)°

.

3. A pharmaceutical formulation comprising omeprazole form A according to claim 1 in admixture with a pharmaceutically acceptable excipient.

4. A method of treatment of gastrointestinal disorders which comprises administration of a therapeutically effective amount of omeprazole form A according to claim 1 to a patient suffering from gastrointestinal disorders.

5. A process for the preparation of omeprazole form A according to claim 1 comprising the steps of:

a) dissolving or suspending omeprazole of any form, or a mixture of omeprazole of any form, in a suitable solvent at 15-25°

C.;

b) allowing the solution to crystallize for at least 2 hours, and

c) isolating the omeprazole form A thus obtained.

6. The process according to claim 5, wherein the solvent used in step a) is selected from the group consisting of methanol, ethanol, acetone, ethyl acetate, methyl tert. butyl ether, toluene and any mixture thereof.