TH57762A - Potassium salt of (S)-omeprazole - Google Patents

Abstract

DC60 (05/11/51) This invention relates to a novel form of 5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridenyl)-methyl]sulfinyl]-1H-benzimidazole, commonly known as omeprazole. More specifically, this invention relates to a novel crystalline form of the potassium salt of the (S)-enansiomer of 5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridenyl)methyl]sulfinyl]-1H-benzimidazole. This invention also relates to a process for the preparation of such potassium salts of (S)-omeprazole and pharmaceutical compositions containing this salt. This invention relates to a novel form of the potassium salt of (S)-omeprazole. 5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridenyl)methyl]sulfinyl]-1H-benzimidazole, known more commonly as omeprazole, is specifically described in this invention as a novel crystalline form of the potassium salt of the (S)-enansiomer of 5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridenyl)methyl]sulfinyl]-1H-benzimidazole. The invention also relates the process for the preparation of such potassium salts of (S)-omeprazole and pharmaceutical mixtures containing this salt.

Claims (9)

1. The potassium salt of (S)-omeprazole form B, which has been characterized by being in the hydrated form. 2. The potassium salt of (S)-omeprazole form B according to claim 1, which has been characterized by crystallization. 3. Potassium salt of (S)-omeprazole form B, which has been characterized by X-ray imaging. The powder diffraction shown is of significant importance with the following values: d[A] Intensity d[A] Intensity 9.6 Very intense 4.10 Light 8.0 Intensity 3.95 Light 7.9 Intensity 3.74 Very intense 7.5 Light 3.67 Medium 7.3 Light 3.58 Intensity 7.2 Very intense 3.55 Medium 5.9 Intensity 3.47 Intensity 5.6 Intensity 3.40 Light 5.2 Intensity 3.27 Intensity 5.1 Very intense 3.20 Medium 4.88 Light 3.15 Medium 4.83 Light 3.10 Light 4.71 Light 3.03 Light 4.67 Light 2.98 Medium 4.55 Medium 2.87 Medium 4.49 Intensity 2.85 Medium 4.39 Strong 2.38 Medium 4.15 Light 2.30 Light 4. The process of preparing the potassium salt of (S)-omeprazole form B as defined in any one of Requisitions 1 through 3, which includes the conversion of (S)-omeprazole to the corresponding potassium salt in toluene or dichloromethane by treatment with a potassium source such as potassium hydroxide or potassium methylate, followed by the extraction of the formed salt. 5. The process under claim 4, which includes an additional step of oxidation of 5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridenyl)methyl]thio]-1H-benzimidazole with an optional oxidizing agent and chirol titanium complex in a basic organic solvent such as toluene or dichloromethane to obtain (S)-omeprazole. 6. A pharmaceutical formulation containing the potassium salt of (S)-omeprazole form B as defined in any one of the claims 1 through 3 in a formulation that is pharmaceutically acceptable. 7. A pharmaceutical formulation suitable for intravenous administration, incorporating the potassium salt of (S)-omeprazole form B as specified in any one of Reservations 1 through 3, in a formulation with a pharmaceutically acceptable formulation agent. 8. The use of the potassium salt of (S)-omeprazole form B, as defined in any one of the claims 1 through 3, as an active ingredient in the production of substances used in the treatment of gastrointestinal disorders. 9. The use of the potassium salt of (S)-omeprazole form B, as defined in any one of the claims 1 through 3, in the manufacture of pharmaceutical formulations for intravenous administration.