- Synthesis of amido-N-imidazolium salts and their applications as ligands in suzuki-miyaura reactions: Coupling of hetero- aromatic halides and the synthesis of milrinone and irbesartan
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A new catalytic system based on palladium-amido-N-heterocyclic carbenes for Suzuki-Miyaura coupling reactions of heteroaryl bromides is described. A variety of sterically bulky, amido-N-imidazolium salts were synthesized in high yields from the corresponding anilines. This catalytic system effectively promoted Suzuki-Miyaura couplings of heteroaryl bromides and chlorides with a range of boronic acids to give the corresponding aryl compounds in high yield. The yield was increased with increasing steric bulkiness of the substituted group. Especially, 1-(2,6-diisopropylphenyl)-3-N-(2,4,6-tri-tert- butylphenylacetamido)imidazolium bromide (4bc) exhibited 850,000 TON in the coupling reaction of 2-bromopyridine and phenylboronic acid. In addition, pharmaceutical compounds such as milrinone and irbesartan were synthesized via Suzuki-Miyaura coupling using sterically bulky, amido-N-imidazolium salt (4bc) as a ligand. Copyright
- Kumar, Manian Rajesh,Park, Kyungho,Lee, Sunwoo
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scheme or table
p. 3255 - 3266
(2011/02/23)
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- PROCESS FOR THE PREPARATION OF IRBESARTAN AND INTERMEDIATE PRODUCTS
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The present invention relates to a new method for the production of irbesartan, having the chemical name 2-n-butyl-4-spirocyclopentane-1-[(2'-(tetrazol-5-yl)biphenyl-4-yl)methyl]-2- imidazolin-5-one, and pharmacologically acceptable salts thereof. Furthermore the invention relates to new (intermediate) compounds which are suitable for the production of irbesartan.
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Page/Page column 13
(2010/01/07)
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- Process for the preparation of 2-alkyl-1-((2'-substituted-biphenyl-4-yl) Methyl)-imidazole, dihydroimidazole or benzimidazloe derivatives
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The invention relates to a new process for the preparation of sartans 2-butyl-3-[[2′-[1-(triphenylmethyl)-1H-tetrazol-5-yl][1,1′-biphenyl]-4-yl]methyl]-1,3-diazaspiro[4.4]non-1-en-4-one is disclosed, which proceeds via novel intermediate, 4-[(2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl]phenylboronic acid (Formula (II)) or its analogs. Compound (II) reacts with 5-(2-bromophenyl)-1-(triphenylmethyl)-1H-tetrazole (III) in the presence of catalyst, using conditions of Suzuki reaction, to give trityl irbesartan (I), whereas analogs to compound (II) may give candesartan, valsartan, telmisartan, losartan and olmesartan.
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Page/Page column 6
(2009/07/18)
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- PROCESSES FOR THE SYNTHESIS OF 5-PHENYL -1 TRITYL-1H-TETRAZOLE
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Provided are processes for the synthesis of 5 -phenyl- 1-trityl-lH-tetrazole, an intermediate useful in the synthesis of irbesartan.
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Page/Page column 17
(2010/11/30)
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- Synthesis and screening for acetylcholinesterase inhibitor activity of some novel 2-butyl-1,3-diaza-spiro[4,4]non-1-en-4-ones: Derivatives of irbesartan key intermediate
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The association of bioactive nucleus with other pharmacological agents is hoped to improve the efficacy of the treatment by combining the effects of different pharmacological mechanisms of action. Keeping this in view, a series of 2-butyl-1,3-diaza-spiro[4,4]non-1-en-4-one derivatives have been synthesized by interaction of 2-butyl-1,3-diaza-spiro[4,4]non-1-en-4-one with different bioactive aralkyl halides in presence of powdered potassium carbonate by two different methods viz., conventional and microwave irradiation. The yields under conventional and microwave irradiation methods were in the range of 60-65% and 80-90%, respectively. The structure elucidation of the new compounds has been carried out with the help of elemental analysis and spectral data. All the synthesized compounds have been screened for their efficacy as acetylcholinesterase (AChE) inhibitor. AChE inhibitory activity study was carried out by using Ellman colorimetric assay with neostigmine as a reference standard against targets from different species, such as pure electric eel AChE, human serum AChE, and rat brain AChE. Among the compounds synthesized, compounds 5a, 5b, 5j showed good inhibition against AChE.
- Kavitha,Gaonkar,Narendra Sharath Chandra,Sadashiva,Rangappa
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p. 7391 - 7398
(2008/09/17)
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- Process for preparation of Irbesartan
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A process for the preparation of Irbesartan of formula (I) using the steps of: (i) reacting 4′ aminomethyl-2-cyano biphenyl of formula (VI) with 1-veleramido cyclopentane carboxylic acid of formula (V) ?in an organic solvent and in the presence of an acid, without activating the —COOH group of compound of formula (V) to give 1-(2′cyanobiphenyl-4-yl-methylaminocarbonyl)-1-pentanoylamino cyclopentane of formula (VII). ?converting the compound of formula (VII) obtained in step (i) to Irbesartan of formula (I) by reacting the compound of the formula (VII) with tributyl tin azide in o-xylene to give Irbesartan of formula (I).
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Page/Page column 13-14
(2008/06/13)
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- AN IMPROVED PROCESS FOR PREPARATION OF IRBESARTAN
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A process for the preparation of Irbesartan of formula (I): Formula (I) comprising the steps of: (i) reacting 4' aminomethyl-2-cyano biphenyl of formula (VI) with 1-veleramido cyclopentane carboxylic acid of formula (V): Formula (VI) and Formula (V) in an organic solvent and in the presence of an acid, without activating the -COOH group of compound of formula (V) to give 1-(2'cyanobiphenyl-4-yl-methylaminocarbonyl)-1-pentanoylamino cyclopentane of formula (VII). Formula (VII) converting the compound of formula (VII) obtained in step (i) to Irbesartan of formula (I) by reacting the compound of the formula (VII) with tributyl tin azide in o-xylene to give Irbesartan of formula (I).
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Page/Page column 23-24
(2008/06/13)
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- PREPARATION OF TETRAZOLE DERIVATIVE
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The present invention relates to a process for the preparation of irbesartan or its pharmaceutically acceptable salts comprising a synthesis of trityl irbesartan by a reaction of 5-(4-(bromomethyl)biphenyl-2-yl)-1-(triphenylmethyl)tetrazole and 2-n-butyl-4-cyclopentane-2-imidazolin-5-one or a salt therof in an organic solvent in the presence of a phase transfer catalyst and a base, a removal of the protecting group and an isolation of irbesartan or its pharmaceutically acceptable salt.
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Page/Page column 10-11
(2008/06/13)
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- PROCESSES FOR THE PREPARATION OF HIGHLY PURE IRBESARTAN
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The present invention relates to processes for synthesis of highly pure irbesartan or pharmaceutically acceptable salts thereof.
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Page/Page column 9; 10
(2010/02/11)
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- SYNTHESIS OF 2-BUTYL-3-(2'-(1-TRITYL-1H-TETRAZOL-5-YL)BIPHENYL-4-YL)-1,3-DIAZASPIROL[4,4]-NON-ENE-4-ONE
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Provided is a novel method of making 2-butyl-3-[[2'(1-trityl-1H-tetrazol-5-yl)biphen-4-yl]methyl]1,3-diazaspiro[4,4]non-1-ene-4-one, which can be converted to irbesartan. Also provided are methods of making irbesartan.
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- Form of irbesartan, methods for obtaining said form and pharmaceutical compositions containing same
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The invention relates to a novel crystalline form of irbesartan, to pharmaceutical compositions containing it, to processes for preparing it, and to a method for treating cardiovascular diseases utilizing it.
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Page column 7-8
(2010/02/08)
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- NOVEL SYNTHESIS OF IRBESARTAN
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Provided are a method of making irbesartan via a Suzuki coupling reaction and a novel intermediate, 2-butyl-3-(4'-bromobenzyl)-1,3-diazaspiro[4.4]non-1-ene-4-one, for such process. The novel process includes the step of reacting such intermediate with a protected imidazolephenylboronic acid.
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