- Method of resolving tamsulosin enantiomer
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The invention relates to a method of resolving tamsulosin enantiomer, and in particular, relates to a method of resolving tamsulosin, represented as the formula (I), into an R-enantiomer and an S-enantiomer. The method includes the steps of: (a) dissolving a solid mixture of (R)-tamsulosin free alkali and (S)-tamsulosin free alkali in a solvent and performing a reaction to the free alkalis with camphor-10-sulfonic acid to form a solution containing a pair of diastereomeric camphor-10-sulfonates of tamsulosin, and then preferentially precipitating one diastereomeric camphor-10-sulfonate of the tamsulosin from the solution containing a pair of the diastereomeric camphor-10-sulfonates of tamsulosin, thereby forming a precipitate, in which one diastereomer is enriched, and a solute, in which the other one diastereomer is enriched; and (b) from one of the precipitate and the solute, releasing tamsulosin free alkali to obtain optical-rotation-enriched tamsulosin free alkali. The method has excellent technical performance.
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- 2-Alkyloxazoles as potent and selective PI4KIIIβ inhibitors demonstrating inhibition of HCV replication
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Synthesis and SAR of 2-alkyloxazoles as class III phosphatidylinositol-4- kinase beta (PI4KIIIβ) inhibitors is described. These compounds demonstrate that inhibition of PI4KIIIβ leads to potent inhibition of HCV replication as observed in genotype (GT) 1a and 1b replicon and GT2a JFH1 virus assays in vitro.
- Keaney, Erin P.,Connolly, Michael,Dobler, Markus,Karki, Rajeshri,Honda, Ayako,Sokup, Samantha,Karur, Subramanian,Britt, Shawn,Patnaik, Anup,Raman, Prakash,Hamann, Lawrence G.,Wiedmann, Brigitte,Lamarche, Matthew J.
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p. 3714 - 3718
(2014/09/17)
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- Tamsulosin derivative
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The optically active compound, R(?)-5-[2-[[2-(2-ethoxyphenoxy)ethyl]amino]propyl]-2-hydroxybenzenesulfonamide in good optical purity, a metabolite of the α1-adrenergic blocking agent tamsulosin, and methods for the preparation thereof. Pharmaceutical compositions including the optically active compound and methods of treatment comprising administration of an effective α-adrenergic antagonistic amount of such compositions to mammals.
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Page/Page column 11
(2008/06/13)
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- A METHOD OF PREPARATION OF (R)-(-)-5(2-AMINOPROPYL)-2-METHOXYBENZENESULFONAMIDE
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A method of preparation of (R)-(-)-5-(2-aminopropyl)-2-methoxybenzenesulfonamide of formula I and its use for production tamsulosin. A protective group is introduced to N-[(1R)-2-(4-methoxyphenyl)-1-methylethyl]-N- [(1 R)-1-phenylethyl)]amine and the resulting amide of formula IX is chlorosulfonated and the resulting sulfochloride is converted to a sulfonamide of formula X, from which the compound of formula I is obtained by hydrogenation.
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Page/Page column 9
(2008/06/13)
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- TAMSULOSIN DERIVATIVE
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The optically active compound, R (-)-5-[2-[[2-(2-ethoxyphenoxy)ethyl] amino] propyl]-2-hydroxybenzenesulfonamide in good chemical and optical purity, a metabolite of the α1-adrenergic blocking agent tamsulosin, and methods for the preparation thereof. Pharmaceutical compositions including the optically active compound and methods of treatment comprising direct administration of an effective α1-adrenergic antagonistic amount of such compositions to mammals.
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Page/Page column 17
(2008/06/13)
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- Process for resolution of tamsulosin and compounds, compositons, and processes associated therewith
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Optically impure tamsulosin including racemic tamsulosin can be resolved into optically pure (R)- or (S)-tamsulosin by the use of diastereomeric sulfonate salts of tamsulosin in a fractional crystallization technique. Racemic tamsulosin free base is a useful starting material for the resolution process and a method of obtaining the same in solid form, including two crystalline polymorphic forms, is also provided.
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- 5-PHENYLTHIAZOLE DERIVATIVES AND USE AS PI3 KINASE INHIBITORS
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Compounds of Formula I in free or salt form, wherein R1,R2,R3,R4, and R5, have the meanings as indicated in the specification, are useful for treating diseases mediated by phosphatidylinositol 3-kinase. Pharmaceutical compositions that contain the compounds and processes for preparing the compounds are also described.
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Page/Page column 44-45
(2010/02/07)
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- Novel phenoxyalkylamine derivatives. VII. Synthesis and pharmacological activities of 2-alkoxy-5-[(phenoxyalkylamino)alkyl]benzenesulfonamide derivatives
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To find a novel α-blocker with high α-blocking selectivity against dopamine D2-receptor affinity, we performed structural modification of the alkylene chains and the substituents on two benzene rings of 2-alkoxy-5-[(phenoxyalkylamino)alkyl]benzenesulfonamide derivatives. The modification of the alkylene chain between the amino moiety in the center of the molecule and the benzene ring (ring A) was found to be the most significant. 5-[2-[[2-(5-Fluoro-2-methoxyphenoxy)ethyl]amino]propyl]-2-methoxybenze nesulfonamide (II-4), which possesses 1-methylethyl as the alkylene chain, exhibited high α-blocking selectivity as well as potent α-blocking activity.
- Sakurai,Mitani,Hashimoto,Morikawa,Yasuda,Koshinaka,Kato,Ito
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p. 1443 - 1451
(2007/10/02)
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