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A technology for paroxetine hydrochloride and hydrate, which is applied to the new paroxetine hydrochloride anhydrate and the fields of its preparation and use, can solve the problem that the paroxetine hydrochloride anhydrate cannot be produced, and the anhydrate is not clear. teaching, etc.

Inactive Publication Date: 2005-08-24
SMITHKLINE BECKMAN CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Subsequent repeated preparations as described in Example 8 have been unable to produce any type of paroxetine hydrochloride anhydrate, and there is no clear teaching in any other route or modified literature that this anhydrate can be produced

Method used

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Examples

Experimental program
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Embodiment 1

[0110] Crystalline paroxetine hydrochloride anhydrate substantially free of bound propan-2-ol (Form A)

[0111] i) Paroxetine hydrochloride propan-2-ol solvate

[0112] Paroxetine hydrochloride hemihydrate (150 g) was stirred with propan-2-ol (1000 ml) and toluene (300 ml) in a round bottom flask and heated to boiling. The solvent was distilled off. The total volume was kept constant by adding fresh propan-2-ol until the boiling point reached about 82°C, indicating that the water had been removed.

[0113] While simultaneously crystallizing, the mixture was cooled to about 50°C. The contents of the flask quickly turned to a thick paste, which was diluted with propan-2-ol (ca. 500 mL) and stirred vigorously. The resulting suspension was cooled to about 30°C and vacuum filtered, taking care to prevent absorption of atmospheric moisture. The solvent-containing filter cake was dried over phosphorus pentoxide under high vacuum.

[0114] 151 g of the solvated paroxetine hydroch...

Embodiment 2

[0127] Paroxetine hydrochloride propan-2-ol solvate

[0128] Paroxetine free base (42.09 g) was dissolved in propan-2-ol (Fisons SLR grade, 210 ml). Hydrogen chloride gas was bubbled into the cooled flask containing propan-2-ol (157 g) until 20.8 g of HCl gas was absorbed. 39 g of this solution (containing approximately 4.6 g HCl) was quickly added to the paroxetine solution and the mixture was stirred rapidly. Crystallization started after about 1 minute and the mixture quickly became an unstirable paste which was left for an hour. The product was collected by filtration, washed with propan-2-ol (50 ml), and vacuum-dried at room temperature in a desiccator containing phosphorus pentoxide to constant weight. A sample was analyzed by NMR spectroscopy and found to contain about 6% by weight propan-2-ol. Some samples were further dried to constant weight in a vacuum oven at 50°C, which took 4 days. NMR spectroscopy indicated that the sample contained about 2% by weight propan...

Embodiment 3

[0130] Paroxetine hydrochloride propan-2-ol solvate

[0131] Paroxetine free base (52.37g) was dissolved in anhydrous propan-2-ol (250ml) and a solution of HCl gas in propan-2-ol (50ml solution containing about 5.8g HCl) was added rapidly with rapid stirring. After 30 seconds crystallization occurred and the mixture was stirred at room temperature for 30 minutes to allow complete crystallization. The product was isolated by suction filtration, washed with 25 ml of anhydrous propan-2-ol, and dried in a desiccator containing phosphorus pentoxide under vacuum at room temperature.

[0132] A sample was analyzed by NMR after 3 days and found to contain 10.5% propan-2-ol. The rest of the material was re-dried in a desiccator with fresh phosphorus pentoxide for 3 days to constant weight. NMR indicated that the product contained 4.7% (w / w) propan-2-ol.

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Abstract

The present invention relates to paroxetine hydrochloride anhydrate substantially free of bound propan-2-ol, several forms of the above, processes for preparing the above, new intermediates useful in preparing the above and methods of treating and / or preventing certain diseases by administering the compounds of the invention to a sufferer in need thereof.

Description

[0001] This application is a divisional application of the invention patent application with the application number 96103526-9 submitted on February 5, 1996, entitled "Paroxetine Hydrochloride Anhydrate Substantially Free of Conjugated Propane 2-ol" . technical field [0002] The present invention relates to novel compounds, processes for their preparation and their use in the treatment of diseases. Background technique [0003] EP-B-223403 (Beecham Group plc) describes paroxetine hydrochloride hemihydrate and its use in the treatment of certain diseases. Example 8 of this document describes the preparation of tablets by crystallization from aqueous solvents. Paroxetine hydrochloride anhydrate in crystalline form, melting point 118°C, IR 890, 1200, 1490, 3400 and 3640 cm -1 . This material is hereinafter referred to as Form Z. Subsequent repetitions of the preparation as described in Example 8 have also been unable to produce any type of paroxetine hydrochloride anhydrate...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K31/00A61K31/443A61K31/445A61K31/4465A61K31/4523A61K31/4525A61P3/00A61P3/04A61P25/00A61P25/04A61P25/24A61P25/26A61P25/28C07D211/22C07D317/00C07D405/12
CPCC07D405/12A61P25/00A61P25/04A61P25/24A61P25/26A61P25/28A61P3/00A61P3/04A61P39/00
Inventor V·W·贾西韦茨N·华德
Owner SMITHKLINE BECKMAN CORP
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