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Pyrrolidyl pyrimidine methanesulfonamide derivatives and preparation method thereof

A technology of pyrrolidinopyrimidine and methanesulfonamide is applied in the field of compound preparation to achieve the effects of fast onset, fast absorption and good stability

Inactive Publication Date: 2010-08-11
漆又毛
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Pyrrolidinyl pyrimidine methanesulfonamide was relatively well tolerated, with no patients withdrawn from the trial due to adverse reactions

Method used

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  • Pyrrolidyl pyrimidine methanesulfonamide derivatives and preparation method thereof
  • Pyrrolidyl pyrimidine methanesulfonamide derivatives and preparation method thereof
  • Pyrrolidyl pyrimidine methanesulfonamide derivatives and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036]

[0037] In a 100ml reaction bottle, add 483.95 mg of pyrrolidinyl pyrimidine methanesulfonamide, dissolve with 50 ml of absolute ethanol, stir, add 98 mg of sulfuric acid, after the reaction is completed, recover and concentrate to obtain 523 mg of pyrrolidinyl pyrimidine methanesulfonamide sulfate, pyrrolidine The pyrrolidinyl pyrimidine methanesulfonamide sulfate was mixed in acetone, added 54mg sodium methoxide to react for 2 hours, concentrated under reduced pressure, added an appropriate amount of ether, precipitated solid, filtered, washed with ether, and dried to obtain pyrrolidinyl pyrimidine methanesulfonamide Sodium bisulfate double salt 502mg, yield 92%.

Embodiment 2

[0039]

[0040]In a 100ml reaction bottle, add pyrrolidinyl pyrimidine methanesulfonamide 483.95, dissolve with 50ml of anhydrous methanol, stir, add 98mg of sulfuric acid, after the reaction is completed, recover and concentrate to obtain 525mg of pyrrolidinyl pyrimidine methanesulfonamide sulfate, pyrrolidinyl pyrimidine Pyrimidine methanesulfonamide sulfate was then mixed in acetone, added 70 mg potassium methylate to react for 2.5 hours, concentrated under reduced pressure, added an appropriate amount of petroleum ether, precipitated solid, filtered, washed with petroleum ether, and dried to obtain pyrrolidinyl pyrimidine methanesulfonate Amide potassium bisulfate double salt 495mg, yield 88%.

Embodiment 3

[0042]

[0043] In a 100ml reaction bottle, add 483.95 mg of pyrrolidinyl pyrimidine methanesulfonamide, dissolve with 50 ml of anhydrous DMF, stir, add 98 mg of sulfuric acid, after the reaction is completed, recover and concentrate to obtain 524 mg of pyrrolidinyl pyrimidine methanesulfonamide sulfate, pyrrolidine Pyrimidinyl pyrimidine methylsulfonamide sulfate was mixed in acetone, added 77 mg ammonium acetate to react for 1 hour, concentrated under reduced pressure, added an appropriate amount of n-hexane, precipitated solid, filtered, washed with n-hexane, and dried to obtain pyrrolidinyl pyrimidine methyl Sulfonamide ammonium bisulfate double salt 357mg, yield 66%.

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Abstract

The invention provides pyrrolidyl pyrimidine methanesulfonamide derivatives which are obtained by reacting pyrrolidyl pyrimidine methanesulfonamide with acid and alkali metal or ammonia compound or amino acid or alkamine or directly reacting the pyrrolidyl pyrimidine methanesulfonamide with acid salt. When the acid or acid salt is sulfate radical, a pyrrolidyl pyrimidine methanesulfonamide hydrogensulfate double salt is obtained; and when the acid or acid salt is phosphate radical, a pyrrolidyl pyrimidine methanesulfonamide di-hydrogen phosphate double salt is obtained. The method has reasonable design, stable process and good production feasibility. The pyrrolidyl pyrimidine methanesulfonamide derivatives have the remarkable advantages of good dissolubility, high bioavailability and the like, can be prepared into preparations, and has rapid absorption and quick effect taking by delivering the pyrrolidyl pyrimidine methanesulfonamide into blood after a patient takes the preparations orally, thereby playing a role of better treating male erectile dysfunction. The invention has the following general formula described in the specification.

Description

technical field [0001] The invention belongs to compound preparation, and relates to pyrrolidinyl pyrimidine methanesulfonamide derivatives, preparation method and application. Background technique [0002] Pyrrolidinyl pyrimidine methanesulfonamide is also known as Avanafil (Avanafil, TA 1790), and its chemical name is 4-[(3-chloro-4-methoxybenzyl)amino]-2-[2-(hydroxymethyl base)-1-pyrrolidinyl]-N-(2-pyrimidinylmethyl)-5-pyrimidinemethanesulfonamide, which can help men with erectile dysfunction (ED) to work within 30 minutes, with a faster onset of action specialty. [0003] Pyrrolidinyl pyrimidine methansulfonamide is a new type of phosphodiesterase inhibitor for the treatment of male sexual dysfunction. At present, phase II clinical trials have been completed in the United States, the European Union and Japan, and phase III clinical trials are about to start. The product was developed by Japan Tanabe Pharmaceutical Company and VIVUS Company. Pyrrolidinyl pyrimidine met...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/14C07H5/06C07H1/00
Inventor 漆又毛
Owner 漆又毛
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