# US 7,612,098 B2 · Amorphous hydrous esomeprazole magnesium

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- Number: US 7,612,098 B2
- Document ID: US7612098B2
- Status: Granted
- Kind: B2
- Application number: 10/651,306
- Filed: 2003-08-28
- Published: 2004-08-26
- Granted: 2009-11-03
- Earliest claimed: 2002-08-30
- Assignees: Dr. Reddy's Laboratories, Inc.
- Inventors: Manne Satyanarayana Reddy; Muppa Kishore Kumar; Koilkonda Purandhar; Keshaboina Sreenath
- Web page: https://patentgrep.com/patent/US7612098B2

## CPC

- C07D 401/12: linked by a chain containing hetero atoms as chain links
- A61K 31/44: Non condensed pyridines; Hydrogenated derivatives thereof
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)

## Abstract

A hydrate of esomeprazole magnesium in the form of an amorphous solid is provided. Methods of preparation and use of, as well as formulation containing the hydrate of esomeprazole magnesium in the form of an amorphous solid are also provided.

## Claims

### Claim 1

A hydrous compound of the formula
wherein one of R1 and R2 is hydrogen and the other is methoxy; A is an alkaline earth or alkali metal; and m and n are 1 or 2; said compound having a moisture content of 2 percent to 10 percent as measured by the Karl Fischer method and being in the form of an amorphous solid.

### Claim 2 (depends on 1)

The compound of claim 1, wherein R2 is methoxy, A is magnesium and m and n are both 2.

### Claim 3

A compound which is a hydrous (S)-5-methoxy-2-[[4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole magnesium, said compound being in the form of an amorphous solid, having substantially the same X-ray powder diffraction pattern as shown in FIG. 1.

### Claim 4

A solid composition which comprises hydrous (S)-5-methoxy-2-[[4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole magnesium as a solid, wherein at least 80% by weight of the solid (S)-5-methoxy-2-[[4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole magnesium has a moisture content of 2 percent to 10 percent as measured by the Karl Fischer method and is in an amorphous form, wherein the (S)-5-methoxy-2-[[4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole magnesium has substantially the same X-ray powder diffraction pattern as shown in FIG. 1.

### Claim 5 (depends on 4)

The composition of claim 4, wherein at least 90% by weight of the solid (S)-5-methoxy-2-[[4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole magnesium has a moisture content of 2 percent to 10 percent as measured by the Karl Fischer method and is in an amorphous form.

### Claim 6 (depends on 4)

The composition of claim 4, wherein at least 95% by weight of the solid (S)-5-methoxy-2-[[4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole magnesium has a moisture content of 2 percent to 10 percent as measured by the Karl Fischer method and is in an amorphous form.

### Claim 7 (depends on 4)

The composition of claim 4, wherein at least 99% by weight of the solid (S)-5-methoxy-2-[[4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole magnesium has a moisture content of 2 percent to 10 percent as measured by the Karl Fischer method and is in an amorphous form.

### Claim 8

Hydrous (S)-5-methoxy-2-[[4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole magnesium in the form of an amorphous solid, made by a process comprising:
a) providing (S)-5-methoxy-2-[[4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole magnesium in an alcohol-containing solvent;
b) contacting said (S)-5-methoxy-2-[[4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole magnesium in an alcohol-containing solvent with water so that a solid mass separates; and
c) isolating said separated solid mass, which is a hydrous (S)-5-methoxy-2-[[4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole magnesium in the form of an amorphous solid;
wherein the hydrous (S)-5-methoxy-2-[[4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole magnesium has substantially the same X-ray powder diffraction pattern as shown in FIG. 1.

### Claim 9 (depends on 1)

A solid pharmaceutical composition comprising the compound of claim 1 and a pharmaceutically acceptable carrier.

### Claim 10

A solid pharmaceutical composition comprising a hydrous (S)-5-methoxy-2-[[4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole magnesium in the form of an amorphous solid, wherein the esomeprazole magnesium has substantially the same X-ray powder diffraction pattern as shown in FIG. 1, and a pharmaceutically acceptable carrier.

### Claim 11 (depends on 1)

A method for reducing gastric acid secretion in a subject which comprises administering to the subject a solid pharmaceutical composition comprising an amount of the compound of claim 1 effective to reduce gastric acid secretion by said subject.