# US 8,546,574 B2 · Conglomerates of tenatoprazole potassium salts

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- Number: US 8,546,574 B2
- Document ID: US8546574B2
- Status: Granted
- Kind: B2
- Application number: 12/448,055
- Filed: 2007-12-03
- Published: 2011-03-10
- Granted: 2013-10-01
- Earliest claimed: 2006-12-04
- Assignees: Sidem Pharma
- Applicants: Avraham Cohen; François Schutze; Suzy Charbit; Stéphane Bernad; Guillaume Tauvel; Marie-Noëlle Petit; Gérard Coquerel
- Inventors: Avraham Cohen; François Schutze; Suzy Charbit; Stéphane Bernad; Guillaume Tauvel; Marie-Noëlle Petit; Gérard Coquerel
- Web page: https://patentgrep.com/patent/US8546574B2

## CPC

- C07D 471/04: Ortho-condensed systems
- A61P 1/00: Drugs for disorders of the alimentary tract or the digestive system
- A61P 1/04: for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- A61P 17/02: for treating wounds, ulcers, burns, scars, keloids, or the like
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The invention relates to conglomerates of tenatoprazole potassium salts of the following general formula (I), that consist of an equimolar mixture of enantiomers having R and S configurations and capable of crystallization in the form of a conglomerate, wherein said salts are selected from tenatoprazole dehydrated potassium salt, tenatoprazole potassium dimethanolate, tenatoprazole potassium diethanolate and tenatoprazole potassium ethylene-glycolate. The invention also relates to a pharmaceutical composition containing such salt, and to the use of said salt.

## Claims

### Claim 1

Method for the preparation of an enantiomerically pure Tenatoprazole sodium salt, said method comprising the steps of:
obtaining a tenatoprazole potassium salts, represented by the following general formula:
comprising an equimolar mixture of enantiomers of R and S configuration; and
crystallizing said tenatoprazole potassium salts in the form of conglomerates, said salts being selected from the group consisting of tenatoprazole potassium salt dihydrate, potassium tenatoprazole dimethanolate, potassium tenatoprazole diethanolate and potassium tenatoprazole ethylene glycolate;
conducting the resolution of the optical enantiomers of one of the corresponding racemic potassium salts, wherein said resolution is according to a process of preferential crystallization, followed by conversion of one of said optical enantiomers of the potassium salt into the corresponding enantiomer of the sodium salt.

### Claim 2 (depends on 1)

The method as claimed in claim 1, wherein said potassium salt is tenatoprazole potassium salt dihydrate, said salt producing an X-ray diffraction spectrum comprising lines at the following inter-reticular distances: 15.16; 8.07; 7.59; 7.23; 7.02; 5.72; 5.55; 5.41; 5.32; 5.05; 4.51; 4.35; 4.29; 4.22; 4.061; 3.926; 3.748; 3.624; 3.539; 3.487; 3.436; 3.392; 3.292; 3.252; 3.222; 3.102; 3.034 (in Angströms).

### Claim 3 (depends on 1)

The method as claimed in claim 1, wherein said potassium salt is potassium tenatoprazole dimethanolate, said salt producing an X-ray diffraction spectrum comprising lines at the following inter-reticular distances: 13.79; 6.87; 5.84; 5.44; 4.83; 4.57; 4.31; 3.97; 3.921; 3.865; 3.794; 3.644; 3.56; 3.508; 3.431; 3.393; 3.309; 3.233; 3.116 (in Angströms).

### Claim 4 (depends on 1)

The method as claimed in claim 1, wherein said potassium salt is potassium tenatoprazole diethanolate, said salt producing an X-ray diffraction spectrum comprising lines at the following inter-reticular distances: 13.79; 10.73; 9.41; 7.75; 6.87; 6.71; 6.40; 6.25; 5.97; 5.463; 5.377; 5.128; 4.918; 4.711; 4.562; 4.418; 4.020; 3.936; 3.892; 3.855; 3.705; 3.656; 3.623; 3.573; 3.508; 3.460; 3.446; 3.363; 3.302; 3.249; 3.167; 3.129; 3.102; 3.043 (in Angströms).

### Claim 5 (depends on 1)

The method as claimed in claim 1, wherein said potassium salt is potassium tenatoprazole ethylene glycolate, said salt producing an X-ray diffraction spectrum comprising lines at the following inter-reticular distances: 12.92; 9.30; 7.89; 7.59; 6.77; 6.05; 5.828; 5.604; 5.409; 5.026; 4.907; 4.657; 4.569; 4.478; 4.295; 4.178; 4.013; 3.972; 3.931; 3.798; 3.692; 3.650; 3.608; 3.543; 3.396; 3.340; 3.300; 3.271; 3.204; 3.148; 3.105; 3.060; 3.013 (in Angströms).

### Claim 6 (depends on 1)

The method as claimed in claim 1, wherein said enantiomerically pure Tenatoprazole sodium salt is S-tenatoprazole sodium salt.

### Claim 7 (depends on 1)

The method as claimed in claim 1, wherein said enantiomerically pure Tenatoprazole sodium salt is R-tenatoprazole sodium salt.