- Silodosin intermediate preparing method
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The invention discloses a silodosin intermediate preparing method. The silodosin intermediate preparing method comprises the following steps of S1, subjecting 5-bromoindoline solution and triethylamine to alkylation reaction to obtain a material A; S2, su
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Paragraph 0087; 0180-0181; 0246-0247; 0253; 0309-0315; 0323
(2019/04/17)
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- Method for preparing silodosin intermediate
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The invention provides a method for preparing a silodosin intermediate. A structural formula of the intermediate is as shown in a formula (1). The preparation method comprises the steps of adopting benzoic acid 3-(7-cyan-5-(2-nitro propyl) indoline-1-yl) propyl ester as a raw material and reducing in a zinc powder/hydrochloric acid system to obtain the silodosin intermediate (I), wherein the specific reduction reaction equation is as shown in the specification. Compared with a hydrogenation method, a zinc powder reduction method of the reaction does not need special equipment and can be smoothly completed by an ordinary reaction kettle, and variation of product purity caused by reduction of cyan is avoided. Compared with an iron powder method, metal mud is easier to remove, a difficult-to-separate nitrogen oxide product is not generated and industrial production is facilitated. The method has the advantages of simple and convenient operation and high selectivity, and a product is easy to separate and purify and easy to amplify.
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Paragraph 0014; 0020-0024
(2017/08/31)
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- Design, Synthesis, and Biological Evaluation of Indoline and Indole Derivatives as Potent and Selective α1A-Adrenoceptor Antagonists
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A series of indoline and indole derivatives were designed, synthesized, and evaluated as selective α1A-adrenergic receptor (α1A-AR) antagonists for the treatment of benign prostatic hyperplasia (BPH). In this study, two highly selective and potent α1A-AR antagonists, compounds (R)-14r (IC50 = 2.7 nM, α1B/α1A = 640.1, α1D/α1A = 408.2) and (R)-23l (IC50 = 1.9 nM, α1B/α1A = 1506, α1D/α1A = 249.6), which exhibited similar activities and better selectivities in cell-based calcium assays as compared with the marketed drug silodosin (IC50 = 1.9 nM, α1B/α1A = 285.9, α1D/α1A = 14.4), were identified. In the functional assays with isolated rat tissues, compounds (R)-14r and (R)-23l also showed high potency and uroselectivity. Most importantly, (R)-14r and (R)-23l can significantly decrease the micturition frequency and increase the mean voided volume of the BPH rats in a dose-dependent manner, making them worthy of further investigation for the development of anti-BPH agents.
- Zhao, Fei,Li, Jing,Chen, Ying,Tian, Yanxin,Wu, Chenglin,Xie, Yanan,Zhou, Yu,Wang, Jiang,Xie, Xin,Liu, Hong
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p. 3826 - 3839
(2016/05/24)
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- N-HALOALKYLINDOLINE INTERMEDIATES, THEIR PROCESS AND USE IN PREPARATION OF SILODOSIN AND ITS DERIVATIVES
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The present invention provides novel indoline compounds, derivatives of Formula 1 and salts thereof; which can be eftectively used for the preparation of a 1 -adrenoceptor antagonists, Silodosin and its pharmaceutically acceptable salts.
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- METHOD FOR PREPARING SILODOSIN
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The present invention relates to a process for preparing silodosin with high optical purity up to 99.9% enantiomeric excess (e.e.) or above. The process makes use of a method step, in which the enantiomers contained in a racemic mixture of a compound represented by the general formula V: wherein * denotes the asymmetric center, R1 is a protecting group, and R2 is cyano or carbamoyl, are separated.
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- NOVEL PROCESS FOR THE SYNTHESIS OF INDOLINE DERIVATIVES
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The present invention provides an improved process for the synthesis of indoline intermidiate and its pharmaceutically acceptable derivatives, salts or solvates thereof, useful in the synthesis of α-1 adrenoceptor blockers such as silodosin.
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Page/Page column 31
(2012/10/18)
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- PROCESS FOR PREPARING AN INTERMEDIATE FOR SILODOSIN
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The present invention provides a process for preparing a compound of formula (I), wherein R1 is a hydroxyl-protecting group and R2 is a cyano group or a carbamoyl group, wherein the process comprises the direct hydrogenation of the corresponding achiral nitro compound and the resolution of the racemic amino compound. The compound of formula (I) can easily be further transferred to silodosin.
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