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Details for Patent: 6,229,010

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Details for Patent: 6,229,010

Title: Polymorphic form of a tachykinin receptor antagonist
Abstract:This invention is concerned with a novel polymorphic form of the compound 2-(R)-(1-(R)-(3,5-bis(trifluoromethyl)-phenyl)-ethoxy)-3-(S)-(4-fluoro)phe nyl-4-(3-(5-oxo-1H,4H-1,2,4-triazolo)methylmorpholine which is a tachykinin receptor antagonist useful in the treatment or prevention of disorders of the central nervous system, inflammatory diseases, pain or migraine, asthma, and emesis. The instant polymorphic form has advantages over the other known forms of 2-(R)-(1-(R)-(3,,5-bis(trifluoro-methyl)-phenyl)ethoxy)-3-(S)-(4-fluoro)ph enyl-4-(3-(5-oxo-1H,4H-1,2,4-triazolo)methylmorpholine in terms of thermodynamic stability and suitability for inclusion in pharmaceutical formulations.
Inventor(s): Crocker; Louis (Belle Mead, NJ), McCauley; James (Belle Mead, NJ)
Assignee: Merck & Co., Inc. (Rahway, NJ)
Filing Date:Dec 09, 1999
Application Number:09/458,168
Claims:1. A process for the preparation of Form I of 2-(R)-(1-(R)-(3,5-bis(trifluoromethyl)-phenyl)ethoxy)-3-(S)-(4-fluoro)phen yl-4-(3-(5-oxo-1H,4H-1,2,4-triazolo)methylmorpholine which comprises:

equilibrating Form II of 2-(R)-(1-(R)-(3,5-bis(trifluoro-methyl)-phenyl)ethoxy)-3-(S)-(4-fluoro)phe nyl-4-(3-(5-oxo- 1H,4H- 1 ,2,4-triazolo)-methylmorpholine in a solvent which is selected from: ethanol, 2-propanol, acetonitrile, and isopropyl acetate; and

collecting the resultant Form I of 2-(R)-(1-(R)-(3,5-bis(trifluoro-methyl)phenyl)ethoxy)-3-(S)-(4-fluoro)phen yl-4-(3-(5-oxo-1H,4H- 1,2,4-triazolo)methylmorpholine.

2. A process for the preparation of Form I of 2-(R)-(1-(R)-(3,5-bis(trifluoromethyl)-phenyl)ethoxy)-3-(S)-(4-fluoro)phen yl-4-(3-(5-oxo-1H,4H- 1,2,4-triazolo)methylmorpholine which comprises:

heating a sample of 2-(R)-(1-(R)-(3,5-bis(trifluoromethyl)phenyl)-ethoxy)-3-(S)-(4-fluoro)phen yl-4-(3-(5-oxo-1H,4H- 1,2,4-triazolo)methylmorpholine of optional morphological composition to a temperature range of 215 to 230.degree. C.;

returning the sample to ambient temperature; and

collecting the resultant Form I of 2-(R)-(1-(R)-(3,5-bis(trifluoro-methyl)phenyl)ethoxy)-3-(S)-(4-fluoro)phen yl-4-(3-(5-oxo-1H,4H-1,2,4-triazolo)-methylmorpholine.

3. The process of claim 2 wherein the morphological composition of the starting 2-(R)-(1-(R)-(3,5-bis(trifluoromethyl)-phenyl)ethoxy)-3-(S)-(4-fluoro)phen yl-4-(3-(5-oxo-1H,4H-1,2,4-triazolo)methylmorpholine is Form II.

4. A process for the preparation of Form I of 2-(R)-(1-(R)-(3,5-bis(trifluoromethyl)-phenyl)ethoxy)-3-(S)-(4-fluoro)phen yl-4-(3-(5-oxo-1H,4H-1,2,4-triazolo)methylmorpholine which comprises:

suspending 2-(R)-(1-(R)-(3,5-bis(trifluoromethyl)-phenyl)ethoxy)-3-(S)-(4-fluoro)phen yl-4-(3-(5-oxo-1H,4H- 1,2,4-triazolo)methylmorpholine of optional morphological composition in a solution of methanol/water;

adding seed crystals of Form I of 2-(R)-(1-(R)-(3,5-bis(trifluoro-methyl)phenyl)ethoxy)-3-(S)-(4-fluoro)phen yl4-(3-(5-oxo-1H,4H-1,2,4-triazolo)methylmorpholine;

stirring the resultant mixture at about 0-50.degree. C. for a period sufficient to result in the formation of Form I of 2-(R)-(1-(R)-(3,5-bis(trifluoromethyl)-phenyl)ethoxy)-3-(S)-(4-fluoro)phen yl-4-(3-(5-oxo-1H,4H-1,2,4-triazolo)methylmorpholine; and

collecting the resultant Form I of 2-(R)-(1-(R)-(3,5-bis(trifluoromethyl)-phenyl)ethoxy)-3-(S)-(4-fluoro)phen yl-4-(3-(5-oxo-1H,4H-1,2,4-triazolo)methylmorpholine.

5. The process of claim 4 wherein the morphological composition of the starting 2-(R)-(1-(R)-(3,5-bis(trifluoromethyl)-phenyl)ethoxy)-3-(S)-(4-fluoro)phen yl-4-(3-(5-oxo-1H,4H-1,2,4-triazolo)methylmorpholine is Form II.

6. The process of claim 1 wherein the solvent is isopropyl acetate.

7. The process of claim 4 wherein the solution of methanol/watersolvent is in a ratio of 2/1 (v/v).
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