- NOVEL PROCESS FOR THE SYNTHESIS OF ENANTIOMERICALLY PURE 2-METHOXY-5-[(2R)-2-(4-ALKYLPIPERAZIN-L-YL)PROPYL]-BENZENESULFONAMIDE
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Where R is C1-C3 alkyl, alkenyl A novel process for synthesis of compound of Formula 1 comprising steroselective catalytic reduction of compound of Formula IV under hydrogen gas pressure to obtain an intermediate compound of Formula II, which on coupling in presence of coupling agent and base in presence of organic solvent to obtain compound of Formula X, Formula X on reacting with deprotecting agent in presence of organic solvent results in formation of compound of Formula XI, condensation of Formula XI with alkyl halide results in formation of compound of Formula I.
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Page/Page column 7
(2012/08/08)
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- Synthesis and α1-adrenoceptor antagonist activity of tamsulosin analogues
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Tamsulosin (-)-1 is the most utilized α1-adrenoceptor antagonist in the benign prostatic hyperplasia therapy owing to its uroselective antagonism and capability in relieving both obstructive and irritative lower urinary tract symptoms. Here we report the synthesis and pharmacological study of the homochiral (-)-1 analogues (-)-2-(-)-5, bearing definite modifications in the 2-substituted phenoxyethylamino group in order to evaluate their influence on the affinity profile for α1-adrenoceptor subtypes. The benzyl analogue (-)-3, displaying a preferential antagonist profile for α1A-than α1D-and α1B- adrenoceptors, and a 12-fold higher potency at α1A- adrenoceptors with respect to the α1B subtype, may have improved uroselectivity compared to (-)-1.
- Sagratini, Gianni,Angeli, Piero,Buccioni, Michela,Gulini, Ugo,Marucci, Gabriella,Melchiorre, Carlo,Poggesi, Elena,Giardin, Dario
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body text
p. 5800 - 5807
(2011/02/26)
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- Improved process for the preparation of tamsulosin hydrochloride
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Ellman's sulfinamide reagent is used in asymmetric synthesis of Tamsulosin hydrochloride. The enantiomeric ratio achieved is 87:13. The crystallization of the same with dibenzoyl tartarate afforded the product 2 with 99.5% ee.
- Reddy, A. Veera,Bhaskara Rao, S. Udaya,Narasimha, G. Lakshmi,Dubey
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experimental part
p. 1451 - 1456
(2009/09/25)
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- AN IMPROVED PROCESS FOR THE PREPARATION OF TAMSULOSIN HYDROCHLORIDE
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The invention relates an improved process for preparing the (R)-(-)5-[2-[[2-(2-ethoxyphenoxyethyl]amino]propyl]-2-methoxybenzenesulfonamide of Formula (I): and its pharmaceutically acceptable salts.
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Page/Page column 8
(2009/01/24)
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- A new enzymatic approach to (R)-Tamsulosin hydrochloride
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An enantioselective baker's yeast mediated approach to the pharmacologically active (R)-enantiomer of Tamsulosin hydrochloride is reported.
- Acetti, Daniela,Brenna, Elisabetta,Fuganti, Claudio
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p. 488 - 492
(2007/10/03)
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- PROCESS FOR THE PREPARATION OF TAMSULOSIN
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The invention includes an improved process for producing tamsulosin comprising reacting 5-(2-aminopropyl)-2-methoxybenzenesulfonamide with 2-(o-ethoxyphenoxy)ethyl bromide in an organic phosphite solvent to obtain tamsulosin. Optically pure (R)- 5-(2-aminopropyl)-2- methoxybenzenesulfonamide can be employed to produce optically pure (R)-tamsulosin product. The organic phosphite solvent utilized in the reaction can include tri-alkyl phosphites such as triethyl phosphite, trimethyl phosphite, and tributyl phosphite. Additionally, processes for producing tamsulosin having a low concentration of by-product contaminants, such as 5-((R)-2- {Bis-[2-(2-ethoxyphenoxy)ethyl]amino}-propyl)-2-methoxybenzenesulfonamide, and the use of such by-products to monitor the chemical purity of tamsulosin, are provided.
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Page/Page column 15; 19-20; 20-21
(2010/11/25)
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- Assymetric formal synthesis of (-)-formoterol and (-)-tamsulosin
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Biologically important (2R)-2-amino-3-phenylpropanes consisted in commercial drugs including (R,R)-formoterol, and (R)-tamsulosin were prepared from chiral (2R)-aziridine-2-carboxylate without any chromatographic separation. Key reactions include regio- and stereoselective ring opening reaction of aziridin-2-yl-phenylmethanol and subsequent cyclization toward enantiopure 4,5-disubastitued oxazolidin-2-ones as synthetic intermediates.
- Kim, Yongeun,Kang, Lae-Sung,Ha, Hyun-Joon,Ko, Seung Whan,Lee, Won Koo
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p. 2243 - 2248
(2008/09/17)
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- PROCESS FOR MANUFACTURING OPTICALLY PURE (R) OR (S)-5-(2-AMINOPROPYL)-2-METHOXYBENZENE SULFONAMIDE
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The invention relates to an improved process for the manufacture of enantiomerically pure R-(+) or S-(+)-5-(2-aminopropyl)-2-methoxybenzene sulfonamide by resolution of (R,S)-5-(2-aminopropyl)-2-methoxybenzene sulfonamide with D-(-) or L-(+)-tartaric acid to form a mixture of diastereomeric salts, separating the diastereomeric salts by kinetic resolution in a mixture of solvent systems of the kind such as herein described, in the specified time and temperature range to provide said R-(-)-5-(2-aminopropyl)-2-methoxybenzene sulfonamide or S-(+)-5-(2-aminopropyl)-2-methoxybenzenesulfonamide with excellent chiral purity more than 99.9 %.
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Page/Page column 3; 9
(2008/06/13)
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- METHOD FOR PRODUCING OPTICALLY ACTIVE COMPOUND
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PROBLEM TO BE SOLVED: To provide a method for simply producing (R)-(-)-5-[2-[2-(2-ethoxyphenoxy)ethylamino]-2-methylethyl]-2-methoxybenzenesulfonamide hydrochloride salt and an intermediate for the same at a reduced cost. SOLUTION: This method for producing the optically active compound expressed by chemical formula (6) comprises subjecting a compound expressed by chemical formula (5) to optical resolution with an optical resolution agent which has an optically active saccharide derivative as an asymmetry identifying part.
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Page/Page column 8
(2008/06/13)
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- SYNTHESIS OF OPTICALLY PURE (R)-5-(2-AMINOPROPYL)-2-METHOXYBENZENESULPHONAMIDE
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The present invention relates to a new process for the preparation of optically pure (R)-5-(2-aminopropyl)-2-methoxybenzenesulphonamide, which is an intermediate in the synthesis of tamsulosin.
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Page/Page column 13
(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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- A PROCESS FOR THE PREPARATION OF ENANTIOMERICALLY PURE (R) OR (S)-5-(2-AMINOPROPYL)-2-METHOXYBENZENESULFONAMIDE
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The invention relates to a process for the manufacture of optically pure (R) or (S)-5-(2-aminopropyl)-2-methoxybenzenesulfonamide with D-i.e. (2S, 3S) or L-i.e. (2R, 3R)-tartaric acid to form a mixture of diastereomeric salts, separating the diastereomeric salts by fractional crystallization in a mixture of solvent systems and at the specified temperature range and contacting the individual salts so separated with a base to provide said R-(-)-5-(2-aminopropyl)-2-methoxybenzenesulfonamide or S-(+)-5-(2-amino propyl)-2-methoxybenzenesulfonamide.
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- Process for producing optically active benzene-sulfonamide derivates
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A process for producing optically active benzenesulfonamide derivative (I) which comprises decomposing m-(2-substituted-alkylaminoalkyl)benzene-sulfonamide derivative (II) wherein R1 and R2 are selected independently from a hydrogen atom and C1-C5 alkyl groups; R3 is a hydrogen atom or a C1-C5 alkyl, hydroxyl or C1-C5 alkoxyl group; R4 is a C1-C5 alkyl group; R5 is a C1-C5 alkyl, carboxy-(C1-C5 alkyl) or (C1-C5 alkoxy)carbonyl-(C1-C5 alkyl) group; and R6 is a substituted or unsubstituted phenyl, carboxyl or (C1-C5 alkoxy)carbonyl group. The compound of formula (II) are obtained by reacting a ketone of formula (III)
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- Sulfamoyl-substituted phenethylamine derivatives, their preparation, and pharmaceutical compositions, containing them
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A novel process is provided for the preparation of optical isomers of certain sulfamoyl-substituted phenethylamine derivatives which exhibit α-adrenergic blocking agents which can be used for various treatments such as for the treatment of congestive heart failure.
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