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160969-03-9Relevant articles and documents
Preparation method of silodosin intermediate
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Paragraph 0043; 0051-0053; 0061-0063 0071-0073; 0081-0082, (2019/04/13)
The invention discloses a preparation method of a silodosin intermediate and relates to the technical field of chemical synthesis of drugs. The preparation method comprises the following steps: subjecting salicyaldehyde and ethylene carbonate to transesterification to obtain 2-(2-hydroxyethoxy)benzaldehyde; then, carrying out a Dakin oxidation reaction to obtain sodium 2-(2-hydroxyethoxy) phenol;then, subjecting sodium 2-(2-hydroxyethoxy) phenol and trifluoroethanol to an etherification reaction to obtain 2-[2-(2,2,2-trifluoroethyoxy)phenoxy]ethyl alcohol; and finally, subjecting 2-[2-(2,2,2-trifluoroethyoxy)phenoxy]ethyl alcohol and methanesulfonyl chloride to an esterfication reaction to obtain the silodosin intermediate 2-[2-(2,2,2-trifluoroethyoxy)phenoxy]ethyl methanesulfonate. The preparation method is novel and short in synthesis route, and a target product can be prepared by only four-step reaction. Both raw materials and reagents used for preparation are cheap, available andenvironment-friendly, all the reaction conditions are mild and controllable, the preparation method is convenient and simple in operation, and the prepared silodosin intermediate is high in purity andyield, suitable for industrial production and wide in prospect and industrial application value.
NOVEL PROCESS FOR THE SYNTHESIS OF PHENOXYETHYL DERIVATIVES
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Page/Page column 23, (2011/09/19)
The present invention provides an improved process for the synthesis of 2-[2- (2,2,2-trifluoroethoxy)phenoxy]ethanol intermediate, its derivatives and/or its pharmaceutically acceptable salts, useful in the synthesis of α-1 adrenoceptor blockers such as silodosin.
N-Arylpiperazinyl-N'-propylamino derivatives of heteroaryl amides as functional uroselective α1-adrenoceptor antagonists
Elworthy, Todd R.,Ford, Anthony P. D. W.,Bantle, Gary W.,Morgans Jr., David J.,Ozer, Rachel S.,Palmer, Wylie S.,Repke, David B.,Romero, Magarita,Sandoval, Leticia,Sjogren, Eric B.,Talamás, Francisco X.,Vazquez, Alfredo,Wu, Helen,Arredondo, Nicolas F.,Blue Jr., David R.,DeSousa, Andrea,Gross, Lisa M.,Kava, M. Shannon,Lesnick, John D.,Vimont, Rachel L.,Williams, Timothy J.,Zhu, Quan-Ming,Pfister, Jürg R.,Clarke, David E.
, p. 2674 - 2687 (2007/10/03)
Novel arylpiperazines were identified as α1-adrenoceptor (AR) subtype- selective antagonists by functional in vitro screening. 3-[4-(ortho- Substituted phenyl)piperazin-1:yl]propylamines were derivatized with N,N- dimethyl anthranilamides, nicotinamides, as well as carboxamides of quinoline, 1,8-naphthyridine, pyrazolo[3,4-b]pyridine, isoxazolo[3,4- b]pyridine, imidazo[4,5-b]pyridine, and pyrazolo[1,5-a]pyrimidines. Strips of rabbit bladder neck were employed as a predictive assay for antagonism in the human lower tract. Rings of rat aorta were used as a 'negative screen' for the test antagonists. Binding to α1-ARs was relatively sensitive to size and electronic features of the arylpiperazine portion of the antagonists and permissive to these features on the heteroaryl carboxamide side. These structure-affinity findings were exploited to produce nicotinamides (e.g. 13ii and 25x) and pyrazolo[3,4-b]pyridines (e.g. 37f and 37y) ligands with nanomolar affinity at the α1-AR subtype prevalent in the human lower urinary tract (pA2 values: 8.8, 10.7, 9.3, and 9.9, respectively) and displaying 2-3 orders of magnitude selectivity over the α(1D)-AR.
1,5,7-trisubstituted indoline compounds and salts thereof
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, (2008/06/13)
Indoline compounds represented by the formula: STR1 wherein R represents a saturated or unsaturated aliphatic acyl group which may have one or more halogen atoms, a hydroxy group, a lower alkoxy group, a carboxy group, a lower alkoxycarbonyl group, a cycloalkyl group or an aryl group as substituents; a hydroxyalkyl group; an aliphatic acyloxyalkyl group; a lower alkyl group having a lower alkoxy group, a carboxy group, a lower alkoxycarbonyl group, an aryl substituted lower alkoxycarbonyl group, a carbamoyl group, a mono- or dialkyl substituted carbamoyl group or a cyano group as substituents; an aromatic acyl group which may have one or more halogen atoms as substituents; a furoyl group or a pyridylcarbonyl group; R1 represents a lower alkyl group which may have one or more halogen atoms or an aryl group as substituents; and pharmaceutically acceptable salts thereof, exhibit a selective suppressive action on urethral contractions, and thus are useful as therapeutic agents for the treatment of dysuria with less hypotension including postural hypotension.
N-ARYLOXYALKYL TRYPTAMINE ALPHA1-ADRENERGIC RECEPTOR ANTAGONISTS
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, (2008/06/13)
The present invention relates to novel N-aryloxyalkyl tryptamine . alpha. 1-adrenergic receptor antagonists of the formula I: STR1 in which n is 2, 3 or 4; q is 1, 2 or 3; t is 0, 1, 2 or 3; z is 0, 1, 2 or 3; each R 1 and R 2 are independently hydroxy, halogen, cyano, (C 1-8)alkyl, (C 1-8)alkyloxy or trifluoromethyl; and R 2 is hydrogen, (C 1-4)alkyl, fluoro(C 1-4)alkyl, difluoro(C 1-4) alkyl, trifluoro(C 1-4)alkyl, (C 1-4) alkyloxy(C 1-4)alkyl, oxo(C 1-4)alkyl, (C 1-8)cycloalkyl, (C. sub.1-8)cycloalkylmethyl or allyl or phenyl(C 1-4)alkyl or heterocyclo(C 1-8)alkyl (optionally substituted with one to two substituents independently selected from (C 1-4)alkyl, (C 1-4) alkyloxy, trifluoromethyl and halogen); R. sup.3 and R 4 are independently hydrogen, (C 1-4) alkyl, (C 1-8)cycloalkyl, (C 1-8)cycloalkylmethyl or allyl; and R. sup. 5 is hydrogen, (C 1-4)alkyl, (C 1-8)cycloalkyl, (C 1-8) cycloalkylmethyl, allyl, (C 1-4) alkylsulfonyl and aminocarbonyl; with the proviso that when n is 2, t is 0, q is 1, z is 0, 1 or 2, R 5 is hydrogen and R 6 is hydroxy or (C 1-8)alkyloxy then at least one of R 3 and R 4 is not hydrogen; and the pharmaceutically acceptable salts, individual isomers, and mixtures of isomers thereof; their uses as therapeutic agents and the methods of their making.
