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Thursday, 19 February 2015

Silodosin

Silodosin.png
SILODOSIN
Urief, 160970-54-7, Rapaflo, KMD 3213, Silodyx, KAD 3213, KMD-3213
Molecular Formula: C25H32F3N3O4
Molecular Weight: 495.53449 g/mol
Alpha 1A adrenoceptor antagonist
Prostate hyperplasia
Kissei Pharmaceutical Co Ltd  INOVATOR
CAS 160970-54-7
2,3-Dihydro-1-(3-hydroxypropyl)-5-[(2R)-2-[[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl]amino]propyl]-1H-indole-7-carboxamide
160970-64-9 (racemate)
169107-04-4 (diHBr)
Properties: [a]D25 -14.0° (c = 1.01 in methanol).
Optical Rotation: [a]D25 -14.0° (c = 1.01 in methanol)
Therap-Cat: In treatment of benign prostatic hypertophy.
a-Adrenergic Blocker.

synthesis..............http://newdrugapprovals.org/2015/02/20/silodosin-for-treatment-of-benign-prostatic-hypertophy/

CN101993407
silodosin for selective inhibition of urethral smooth muscle contraction and reduce the pressure within the urethra, but no significant impact on blood pressure, for the treatment of benign prostatic hyperplasia. At present, the method of synthesis Silodosin many reports, but the lack of high yield method for industrial production.
  JP200199956 reported that benzoic acid as a starting material, 1_ (3_ benzoyloxy-propyl) indoline hydrochloride (structural formula (1), R is a hydrogen atom) in 60% yield, then through the multi-step reaction was further prepared silodosin intermediate 1- (3-benzoyloxy-propyl) -5- (2-nitro-propyl) -7-cyano-indoline (structural formula VIII ), the total yield is low, and only 20 percent. Compound (VIII) with potassium carbonate, the reaction of hydrogen peroxide to yield compound (IX), impurities, and purified by column chromatography to be not suitable for industrial production. Compound (IX) under catalysis of molybdenum oxide, and L- (S) – benzyl glycyl alcohol asymmetric reactions, protecting groups may be due to steric hindrance is small, low chiral induction, is 3.8: I.

Figure CN101993407BD00061

Figure CN101993407BD00071
Silodosin Preparation: 12  Example
  Example 11 to give 8 g solid, dissolved in DMSO 100ml, was added 5mol / L NaOH 12ml, 18 ~ 20 ° C was added dropwise slowly with 30% H2027 grams, then 30 ° C, the reaction ended 4h. Extracted with ethyl acetate, the combined organic layer was washed 2N HCl and then the organic layer, the aqueous layer was neutralized with sodium hydroxide, and then extracted with ethyl acetate, washed with saturated sodium bicarbonate, dried over anhydrous sodium sulfate, and evaporated concentrated and then dissolved in ethyl acetate, natural cooling crystallization, filtration, drying 5 g (87%), purity> 99%.
 Silodosin.png

  Mp 105 ~ 108 ° C
  [a] 20d = -16.2 C = I, MeOH
  1NMR spectrum (DMS0-d6): δ ppm 0.9-1.0 (3H, d), 1.5-1.6 (1H, s), 1.6-1.7 (2H, m),
2.3-2.4 (1H, dd), 2.6-2.7 (1H, dd), 2.8-3.0 (5H, m), 3.1-3.2 (2H, m), 3.3-3.4 (2H, m),
3.4-3.5 (2H, t), 4.0-4.1 (2H, t), 4.2-4.3 (1H, s), 4.6-4.8 (2H, t), 6.9-7.15 (6H, m),
7.2-7.3 (1H, s), 7.5-7.6 (1H, s)

synthesis..............http://newdrugapprovals.org/2015/02/20/silodosin-for-treatment-of-benign-prostatic-hypertophy/
सुकून उतना ही देना प्रभू, जितने से
जिंदगी चल जाये।
औकात बस इतनी देना,
कि औरों का भला हो जाये।
synthesis..............http://newdrugapprovals.org/2015/02/20/silodosin-for-treatment-of-benign-prostatic-hypertophy/



सुकून उतना ही देना प्रभू, जितने से
जिंदगी चल जाये।
औकात बस इतनी देना,
कि औरों का भला हो जाये।









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