cas 106133-20-4, Tamsulosin | Articles data

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Continuous-Flow Synthesis of (R)-Tamsulosin Utilizing Sequential Heterogeneous Catalysis
We describe the continuous-flow synthesis of (R)-tamsulosin, a blockbuster therapeutic drug employed for dysuria associated with urinary stones and benign prostatic hyperplasia, by utilizing sequential heterogeneous catalysis. Two heterogeneous catalysts have been developed for the synthesis, and the key step involves reductive amination of nitriles using dimethylpolysilane-modified Pd on activated carbon/calcium phosphate. Overall, (R)-tamsulosin was obtained in 60 % yield and 64 % ee (99 % ee after recrystallization) in a flow stream through four catalytic transformations without the need for the isolation or purification of any intermediates or byproduct.
Ishitani, Haruro,Kobayashi, Shū,Laroche, Benjamin,Nishizawa, Ken,Saito, Yuki
(2022/02/16)

Preparation method of tamsulosin hydrochloride
The invention belongs to the technical field of chemical synthesis, and relates to a synthesis method of tamsulosin hydrochloride. The preparation method comprises the following steps: firstly reacting benzenesulfonamide as shown in a formula (II) with bromo ether as shown in a formula (III) to obtain a condensation compound intermediate as shown in a formula (IV), carrying out transfer hydrogenation reaction on the intermediate as shown in the formula (IV) in the presence of ammonium formate and a catalyst to obtain R-tamsulosin free alkali as shown in a formula (V), subjecting the R-tamsulosin free alkali and hydrochloric acid to a salt forming reaction in an organic solvent, so that the tamsulosin hydrochloride shown in the formula (I) is obtained. The method is characterized in that the reaction of the formula (II) and the formula (III) is carried out in a solvent containing water. According to the synthesis route disclosed by the invention, in the reaction process of the obtained tamsulosin hydrochloride, no disubstituted by-product generated by reaction of bimolecular bromide and amine exists, the obtained tamsulosin hydrochloride has the advantages of good product purity, stable quality and high yield, and the synthesis method disclosed by the invention is mild in reaction condition and convenient to synthesize.
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(2021/05/22)

Preparation method of tamsulosin hydrochloride crystal form
The invention relates to the technical field of preparation of crystal forms of organic compounds, in particular to a preparation method of a tamsulosin hydrochloride crystal form. The method comprises the following steps: completely dissolving tamsulosin in a solvent at 60-70 DEG C, then dropwise adding acid for reaction for a period of time, conducting cooling to 20-30 DEG C, and conducting filtering, washing and drying to obtain tamsulosin, wherein tamsulosin is a refined product. The method is simple in process, high in yield, high in product purity and suitable for large-scale industrialization.
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Paragraph 0017-0020

(2021/05/26)

Preparation method of tamsulosin hydrochloride
The invention provides a preparation method of tamsulosin hydrochloride. Specifically, the preparation method comprises a step of reacting 5-acetonyl-2-methoxybenzenesulfonamide with (R)-1-phenylethylamine under the action of a reducing agent to obtain a compound as shown in a formula (IV) or pharmaceutically acceptable salt thereof, and further comprises a step of preparing tamsulosin hydrochloride from the compound as shown in the formula (IV) or pharmaceutically acceptable salt thereof. The preparation method provided by the invention is high in safety and strong in operability, avoids theuse of a heavy metal catalyst, and has an industrial actual use value.
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(2020/07/13)

A high optical purity of tamsulosin preparation method of leach
The invention discloses a preparation method of tamsulosin hydrochloride with high optical purity, and belongs to a medicine technology and a chemical field. A recrystallization method is adopted, crude products of (R)-5-(2-(2-(2-ethoxyphenoxy) ethyl amino) propyl)-2-methoxyl phenyl sulfonamide hydrochloride are refined, so that pure products of the (R)-5-(2-(2-(2-ethoxyphenoxy) ethyl amino) propyl)-2-methoxyl group sulfonamide hydrochloride of which the e.e. value is larger than 99.8% is obtained; a crystallizing solvent adopted by the recrystallization method is a mixed solvent consisting of an organic solvent and water, the organic solvent is selected from one of methanol, ethyl alcohol, acetone, acetonitrile and isopropyl alcohol, and the recrystallization temperature is under 15 DEG C. The preparation method disclosed by the invention is simple to operate, short in period, low in cost and good in repeatability, and can solve the inevitable problem of rework for treatment in the industrial production.
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Paragraph 0037; 0040; 0043; 0044; 0045; 0046; 0049

(2018/10/02)

Method of resolving tamsulosin enantiomer
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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Paragraph 0187-0191

(2017/08/29)

PROCESS FOR PREPARATION OF HIGH PURITY TAMSULOSIN OR SALT THEREOF
The present invention refers to of the existing method contain pharmaceutically available plasticizer manufacturing method compared to a simple, low-environmentally friendly, purity contain pharmaceutically available plasticizer or contain pharmaceutically available plasticizer hydrochloride provides manufacturing method. (by machine translation)
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Paragraph 0072; 0101-0103

(2016/10/10)

Novel Pharmaceutical Forms, and Methods of Making and Using the Same
Crystalline salts, polymorphs, solvates, and hydrates of bicalutamide, 5-fluorouracil, donepezil, anastrozole, nelfinavir, mirtazapine, lansoprazole, and tamsulosin, or derivatives thereof are provided by the subject invention. Methods of making and using the same are also provided.
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Page/Page column 11

(2012/02/01)

Process for Preparing Tamsulosin Hydrochloride
The invention relates to an process for preparing Tamsulosin hydrochloride of Formula (I) which comprises (i) reacting (R)-(?)-5-(2-amino-propyl)-2-methoxybenzenesulfonamide of Formula (II) with substituted phenoxy compound of Formula (III), wherein Z represents a removing group, such as —OSO2CH3, —OSO2C6H4CH3, —F, —Br, —Cl, or —I, in a solvent in the presence of an alkaline earth metal oxide to obtain Tamsulosin base and (ii) converting Tamsulosin base into hydrochloride salt in a solvent by addition of aqueous hydrochloric acid.
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Page/Page column 3

(2010/11/03)

METHOD FOR PRODUCING OPTICALLY ACTIVE AMINE
The present invention provides a method for producing chiral amines, comprising asymmetric transfer hydrogenation of imine compounds in the presence of a hydrogen donor compound and an iridium(III) complex having a chiral prolinamide compound as a ligand. The present invention is useful for production of chiral amines in an efficient manner in terms of their optical and chemical yields.
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Page/Page column 12

(2010/04/25)

THERAPY FOR COMPLICATIONS OF DIABETES
A method for enhancing glycemic control and/or insulin sensitivity in a human subject having diabetic nephropathy and/or metabolic syndrome comprises administering to the subject a selective endothelin A (ETA) receptor antagonist in a glycemic control and/or insulin sensitivity enhancing effective amount. A method for treating a complex of comorbidities in an elderly diabetic human subject comprises administering to the subject a selective ETA receptor antagonist in combination or as adjunctive therapy with at least one additional agent that is (i) other than a selective ETA receptor antagonist and (ii) effective in treatment of diabetes and/or at least one of said comorbidities other than hypertension. A therapeutic combination useful in such a method comprises a selective ETA receptor antagonist and at least one antidiabetic, anti-obesity or antidyslipidemic agent other than a selective ETA receptor antagonist.
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(2009/07/02)

ANTIHYPERTENSIVE THERAPY
A new use of darusentan is provided in preparation of a pharmaceutical composition for lowering blood pressure in a patient exhibiting resistance to a baseline antihypertensive therapy with one or more drugs. The composition comprises darusentan in an amount providing a therapeutically effective daily dose; wherein (a) the composition is orally deliverable and/or (b) the daily dose of darusentan is effective to provide a reduction of at least about 3 mmHg in one or more blood pressure parameters selected from trough sitting systolic, trough sitting diastolic, 24-hour ambulatory systolic, 24-hour ambulatory diastolic, maximum diurnal systolic and maximum diurnal diastolic blood pressures. Further provided is a new use of darusentan in preparation of a pharmaceutical composition for lowering blood pressure in a patient exhibiting resistance to a baseline antihypertensive therapy, wherein the composition is administered adjunctively with at least one diuretic and at least one antihypertensive drug selected from ACE inhibitors, angiotensin II receptor blockers, beta-adrenergic receptor blockers and calcium channel blockers.
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(2009/09/08)

AN IMPROVED PROCESS FOR THE PREPARATION OF TAMSULOSIN HYDROCHLORIDE
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 9

(2009/01/24)

A new enzymatic approach to (R)-Tamsulosin hydrochloride
An enantioselective baker's yeast mediated approach to the pharmacologically active (R)-enantiomer of Tamsulosin hydrochloride is reported.
Acetti, Daniela,Brenna, Elisabetta,Fuganti, Claudio
p. 488 - 492
(2007/10/03)

AN IMPROVED PROCESS FOR PREPARING TAMSULOSIN HYDROCHLORIDE
The invention relates to an process for preparing Tamsulosin hydrochloride of Formula (I) which comprises (i) reacting (R)-(-)-5-(2-aminopropyl)-2-methoxybenzenesulfonamide of Formula (II) with substituted phenoxy compound of Formula (III), wherein Z represents a removing group, such as -OSO2CH3, -OSO2C6H4CH3, -F, -Br, -Cl, or -I, in a solvent in the presence of an alkaline earth metal oxide to obtain Tamsulosin base and (ii) converting Tamsulosin base into hydrochloride salt in a solvent by addition of aqueous hydrochloric acid.
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Page/Page column 6-7

(2008/06/13)

PROCESS FOR THE PREPARATION OF TAMSULOSIN
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 15-16

(2010/11/25)

Process for preparation of tamsulosin and its aralkylamine derivatives
The present invention discloses a new process for the synthesis of tamsulosin and its aralkylamine derivatives, especially (R)-(?)-5-{2-[2-(2-alkoxyphenoxy)ethylamino]propyl}-2-alkoxybenzenesulfonamides having the following formula 1 (where R1 and R2 represent C1-C4 alkyl groups) and their hydrochloride thereof, and other various pharmaceutical used salts. Tamsulosin hydrochloride (R1=Et, R2=Me, in its hydrochloride salt form) is an antagonist of α-A adrenoceptors in the prostate. Tamsulosin?HCl occurs as white crystals, which melt with decomposition at approximately 230° C. It is sparingly soluble in water and in methanol, slightly soluble in glacial acetic acid and in ethanol, and practically insoluble in ether.
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Page/Page column 7

(2008/06/13)

A PROCESS FOR THE PREPARATION OF R (-) TAMSULOSIN HYDROCHLORIDE
The invention discloses a process for the preparation of highly pure R (-)-5-(2-(2-(2-ethoxy phenoxy) ethylamine) propyl)-2-methoxy benzene sulfonamide hydrochloride used to treat symptoms of urinary difficulty. R-(-)-2-(4-methoxy phenyl)- 1 -methyl ethyl amine is condensed with halo-acetyl halide in the presence of base and a halogenated solvent. The resulting R-(-)- halo-N-[2-(4-methoxy phenyl)- 1 -methyl ethyl] acetamide is treated with chlorosulphonic acid and ammonia. R-(-)-N-[2-(3-amino sulfonyl-4-methoxy phenyl)- 1 -methyl ethyl]-2- haloacetamide obtained is treated with 2- ethoxy phenol in the presence of an inorganic base and water to obtain R-(-)-N-[2-(3-amino sulfonyl-4-methoxy phenyl)- 1 -methyl ethyl]-2-(2- ethoxy phenoxy) acetamide in high yield and purity. The amide obtained is reduced to obtain the Tamsulosin base, which is then purified and converted to its hydrochloride salt.
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Page/Page column 13

(2010/11/28)

PROCESS FOR THE PREPARATION OF TAMSULOSIN AND RELATED COMPOUNDS
The invention relates, in general, to the preparation of tamsulosin free base. More particularly, the invention relates to a process for preparing pure solid crystalline tamsulosin in its free base form as a precursor for the production of tamsulosin hydrochloride.
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Page/Page column 17-18; 19-20

(2008/06/13)

Method for treating resistant hypertension
A method is provided for lowering blood pressure in a patient having clinically diagnosed resistant hypertension. The method comprises administering darusentan to the patient adjunctively with a baseline antihypertensive regimen that comprises administration of at least one diuretic and at least two antihypertensive drugs selected from at least two of (a) ACE inhibitors and angiotensin II receptor blockers, (b) beta-adrenergic receptor blockers and (c) calcium channel blockers. The darusentan is orally administered at a dose and frequency effective, in combination with the baseline regimen, to provide a reduction of at least about 3 mmHg in one or more blood pressure parameters selected from trough sitting systolic, trough sitting diastolic, 24-hour ambulatory systolic, 24-hour ambulatory diastolic, maximum diurnal systolic and maximum diurnal diastolic blood pressures.
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(2008/06/13)

Process for preparing tamsulosin
The present invention relates to a process for preparing Tamsulosin, an anti-benign prostatic hyperplasia drug, which comprises converting o-ethoxyphenoxyethanol to a corresponding sulfonate, and reacting the sulfonate with (R)-(?)-5-(2-aminopropyl)-2-methoxybenzenesulfonamide by condensation to produce Tamsulosin.
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Page/Page column 3-4

(2008/06/13)

Process for the resolution of racemic (R,S) -5-(2-(2-(2- ethoxyphenoxy) ethylamino)propyl)-2-methoxybenzene sulfonamide (tamsulosin), its novel R and S isomers and their salts and processes for their preparation
An improved process is described to resolve a racemic mixture in any proportion of 5-(2-(2-(2-ethoxyphenoxy)ethylamino)propyl)-2-methoxy benzene sulfonamide as a free base or some of its salts, with BPA either S or R form to obtain enantiomerically highly pure R and S-isomer as a well characterized free base or as a salt of the title compound. Also described are novel R and S-isomers of 5-(2-(2-(2-ethoxyphenoxy) ethylamino)propyl)-2-methoxy benzene sulfonamide and their salts and the processes for their preparation.
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Page/Page column 7

(2010/10/20)

Process for preparation of tamsulosin and its derivatives
The present invention discloses a new process for the synthesis of tamsulosin derivatives of formula 1 (where R 1 and R 2 represent C 1 -C 4 alkyl groups) and their hydrochlorides and other pharmaceutically acceptable salts, comprising reacting the hydrochloride of sulphonamide 2 (where R represents C 1 -C 4 alkyl) with the ether compound 21 (where R' represents C 1 -C 4 alkyl and R" represents MeC 6 H 4 SO 2 or MeSO 2 ).
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Page/Page column 5; 12

(2008/06/13)

CRYSTALLIZATION PROCESS
The invention relates to a process for the production of tamsulosin hydrochloride crystals where the crystal size distribution is controlled by controlling the temperature where hydrochloric acid is added to the reaction mixture.
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Page/Page column 4-5

(2008/06/13)

POLYMORPHIC FORMS OF (R)-(-)-TAMSULOSIN
The invention relates to processes for the preparation of polymorphic forms of (R)-(-)- tamsulosin. More particularly, it relates to the preparation of polymorphic forms of (R)-(-)- tamsulosin designated as Form I and II. The invention also relates to pharmaceutical compositions that include the Form I and Form II and use of the compositions for treating signs and symptoms of benign prostrate hyperplasia.
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Page/Page column 10

(2008/06/13)

PROCESS FOR THE PREPARATION OF TAMSULOSIN AND INTERMEDIATES THEREOF
A process for producing tamsulosin of formula (I) and pharmaceutically acceptable addition salts, thereof comprises the steps of : a) Reacting compound R,R-[2-(4-methoxy-phenyl)-1-methyl-ethyl]-(1-phenyl-ethyl)-amine of formula (II) or a salt thereof (II) with chlorosulfonic acid with or without an organic solvent, to obtain compound R,R-2methoxy-5-[2-(1-phenyl-ethylamino)-propyl]-benzenesulfonic acid of formula (III) b) Hydrogenolysis of compound R,R-2-methoxy-5-[2-(1-phenyl-ethylamino)-propyl]- benzenesulfonic acid of formula III or a salt thereof carried out in an alcohol in the presence of a palladium catalyst using hydrogen or a source of hydrogen, to obtain compound R-(-)-5-(2-amino-propyl)-2-methoxy-benzenesulfonic acid of formula (IV) c)Reacting primary amine R-(-)-5-(2-amino-propyl)-2-methoxy-benzenesulfonic acid of formula (IV), or a salt thereof, with a compound of formula (V) wherein X represents an halogen atom selected from the group consisting of C1;Br and I, to obtain 5- [(2R)-2-[2-(2-ethoxy-phenoxy)-ethylamino]-propyl]-2-methoxy-benzenesulfonic acid compound of formula (VI) d) Reacting compound of formula (VI) with an halogenating agent, to obtain the corresponding sulfonylchloride of formula (VII). e)Reacting compound VII with ammonia to obtain compound I.
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Page/Page column 14-15

(2008/06/13)

Process for the separation of R(-)-and S(+)-5-[2-[[2-(2-ethoxyphenoxy)ethyl]amino]propyl]-2-methoxybenzenesulfonamide
The process for separating the R(?)- and S(+)-5-[2-[[2-(2-ethoxyphenoxy)ethyl]amino]propyl]-2-methoxybenzene-sulfonamide enantiomers comprises (a) reacting a mixture of said enantiomers with an optically active organic acid to form diastereoisomeric salts with said enantiomers, where in said diastereoisomeric salts have different solubility and can be separated by crystallization; (b) separating the diastereoisomeric salt mixture enriched in the salt of one of the enantiomers; and (c) releasing said salts to obtain the R(?)or S(+) enantiomer. The R(?)-5-[2-[[2-(2-ethoxyphenoxy) ethyl]amino]propyl]-2-methoxybenzenesulfonamide enantiomer has α-adrenergic blocking activity and is useful as an antihypertensive agent suitable for the treatment of congestive heart failure and benign prostatic hypertrophy.
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Page 6

(2010/02/10)

METHOD FOR PRODUCING OPTICALLY ACTIVE COMPOUND
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 8-9

(2008/06/13)

AMORPHOUS TAMSULOSIN HYDROCHLORIDE
In the present invention, amorphous tamsulosin hydrochloride, the process for preparation thereof by lyophilisation or spray-drying and the properties thereof are disclosed. Amorphous tamsulosin hydrochloride is useful in the preparation of pharmaceutical formulations for use particularly in the treatment of benign prostatic hyperplasia.
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Page/Page column 8

(2008/06/13)

NOVEL INTERMEDIATES FOR THE SYNTHESIS OF (R)-TAMSULOSIN AND OF ITS PHARMACEUTICALLY ACCEPTABLE SALTS AND PROCESS FOR THEIR PREPARATION
A subject matter of the present invention is novel intermediates for the synthesis of (R)-tamsulosin and of its pharmaceutically acceptable salts, and also the associated preparation process.
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Page/Page column 32-33

(2008/06/13)

METHOD OF PREPARING OPTICALLY PURE PHENETHYLAMINE DERIVATIVES
Provided is a method of preparing an optically pure compound having formula 1 or its salts. The method includes: reacting -2-(4-methoxy-3-aminosulfonyl-phenyl)-1-methylethylamine or its salts with a compound selected form the group consisting of chloroacetic acid, bromoacetic acid, fluoroacetic acid, iodoacetic acid, α-halogenoacetic acid anhydride, and α-halogenoacetyl halide in the presence of a base or an acylating agent.
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Page/Page column 10; 11

(2010/02/12)

PREPARATION OF R-5-(2-(2-ETHOXYPHENOXYETYLAMINO)PROPYL)-2- METHOXYBENZENESULPHONAMIDE HYDROCHLORIDE OF HIGH CHEMICAL
In the present invention, the process for the preparation of tamsulosin hydrochloride and subsequent purification with thermal crystallisation to provide essentially pure tamsulosin hydrochloride is disclosed.
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Page/Page column 8-10

(2008/06/13)

A METHOD OF PREPARATION OF (R)-(-)-5(2-AMINOPROPYL)-2-METHOXYBENZENESULFONAMIDE
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 11

(2008/06/13)

SYNTHESIS OF OPTICALLY PURE (R)-5-(2-AMINOPROPYL)-2-METHOXYBENZENESULPHONAMIDE
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 13-14

(2008/06/13)

PROCESS FOR THE PREPARATION OF TAMSULOSIN
There is provided a process for the preparation of tamsulosin of formula 5, involving a coupling reaction in the presence of an aluminum reagent between an ester of formula 2A and (R)-5-(2-amino)propyl-2-methoxy-benzenesulfonamide of formula 3 to yield tamsulosin amide, which is then reduced to yield tamsulosin.
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Page/Page column 9

(2010/02/11)

Purification process of Tamsulosin
Disclosed herein is a process for purifying tamsulosin. The process comprises the steps of adding a carboxylic compound to tamsulosin represented by Formula 1 below: in an organic solvent to obtain a tamsulosin carboxylate in the form of precipitates, and adding hydrochloric acid to the precipitated tamsulosin carboxylate to prepare high purity tamsulosin hydrochloride containing only a trace amount of impurities.
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Page 4

(2008/06/13)

AN IMPROVED PROCESS FOR THE PREPARATION OF TAMSULOSIN HYDROCHLORIDE
The present invention relates to an improved process for the preparation of Tamsulosin hydrochloride. Tamsulosin hydrochloride is a widely used drug for the treatment of benign prostate hyperplasia. Tamsulosin hydrochloride has the formula-I given below. (I) The process employs the novel intermediates quarternised benzylidene ammonium salts, N-(phenyl substituted)-[2-(2-ethoxyphenoxy)ethyl]-[2-(4-methoxy-3-sulphamoylphenyl)-1(R)-methyl-ethyl]ammonium halides of the formula-II, (II) where R represents H, 4-OCH3, 4-OH or 4-fluoro and X represents C1, Br or I. And Schiff's bases, novel phenyl substituted 2-methoxy-5-[(2R)-[(1-E/Z-phenyl methylene)amino]propyl]benzenesulfonamide of the formula-III. (III) where R represents H, 4-OCH3, 4-OH or 4-fluoro.
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Page 20-21

(2008/06/13)

AN IMPROVED PROCESS FOR THE PREPARATION OF (R) (-) TAMSULOSIN HYDROCHLORIDE
A process for the preparation of (R)(-) Tamsulosin hydrochloride [(R)(-)-5-[2-[[2-(o-ethoxy-phenoxy)ethyl]amino]-2-methylethyl]-2-methoxybenzenesulfonamide hydrochloride] of formula (III), The (R)(-) Tamsulosin hydrochloride of formula (III) produced by the process has an alpha-adrenergic blocking action and possesses a hypotensive activity and is used mainly for the treatment of benign prostatic hyperplasia (BPH). The process is directed to be high yielding, cost effective, easy to operate at industrial scale and does not involve the use of moisture sensitive, pyrophoric compounds. Importantly, the process would avoid unreacted contaminants in the final product and provide for isolating and obtaining the final product with good yield and purity. Advantageously, the process would not require the handling of hazardous reagents, such as LAH. The process is also selective, industrially favourable in that the same would use less amount of solvent, hence increase the plant capacity and will also require less manpower.
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Page 10-11

(2008/06/13)

Process for resolution of tamsulosin and compounds, compositons, and processes associated therewith
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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(2008/06/13)

Sulfamoyl-substituted phenethylamine derivatives, their preparation, and pharmaceutical compositions, containing them
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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(2008/06/13)

Process for producing optically active benzene-sulfonamide derivates
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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(2008/06/13)