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1. WO2006046253 - A ONE-POT PROCESS FOR THE PREPARATION OF ANTIEMETIC AGENT, 1,2,3,9-TETRAHYDRO-9-METHYL-3[(2-METHYL)-1H-IMIDAZOLE-1-YL)METHYL]-4H-CARBAZOL-4-O

Publication Number WO/2006/046253
Publication Date 04.05.2006
International Application No. PCT/IN2004/000336
International Filing Date 26.10.2004
IPC
C07D 233/56 2006.1
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
233Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
54having two double bonds between ring members or between ring members and non-ring members
56with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
C07D 403/06 2006.1
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
403Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/167
02containing two hetero rings
06linked by a carbon chain containing only aliphatic carbon atoms
A61K 31/415 2006.1
AHUMAN NECESSITIES
61MEDICAL OR VETERINARY SCIENCE; HYGIENE
KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
31Medicinal preparations containing organic active ingredients
33Heterocyclic compounds
395having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
41having five-membered rings with two or more ring hetero atoms, at least one of which is nitrogen, e.g. tetrazole
4151,2-Diazoles
CPC
C07D 403/06
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
403Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
02containing two hetero rings
06linked by a carbon chain containing only aliphatic carbon atoms
Applicants
  • IPCA LABORATORIES LIMITED [IN]/[IN] (AllExceptUS)
  • KUMAR, Ashok [IN]/[IN] (UsOnly)
  • SINGH, Dharmendra [IN]/[IN] (UsOnly)
  • JADHAV, Atul [IN]/[IN] (UsOnly)
  • PANDYA, Darpan, Navinchandra [IN]/[IN] (UsOnly)
  • PANMAND, Deepak, Shankar [IN]/[IN] (UsOnly)
  • THAKUR, Gajendrasingh, Ramsingh [IN]/[IN] (UsOnly)
Inventors
  • KUMAR, Ashok
  • SINGH, Dharmendra
  • JADHAV, Atul
  • PANDYA, Darpan, Navinchandra
  • PANMAND, Deepak, Shankar
  • THAKUR, Gajendrasingh, Ramsingh
Agents
  • NAIR, Gopakumar, G.
Priority Data
Publication Language English (en)
Filing Language English (EN)
Designated States
Title
(EN) A ONE-POT PROCESS FOR THE PREPARATION OF ANTIEMETIC AGENT, 1,2,3,9-TETRAHYDRO-9-METHYL-3[(2-METHYL)-1H-IMIDAZOLE-1-YL)METHYL]-4H-CARBAZOL-4-O
(FR) PROCEDE MONOTOPE DE PREPARATION DE L'AGENT ANTIEMETIQUE 1,2,3,9-TETRAHYDRO-9-METHYL-3[(2-METHYL-1H-IMIDAZOLE-1-YL)METHYL]-4H-CARBAZOL-4-ONE
Abstract
(EN) A one-pot industrial process for preparing 1,2,3,9-tetrahydro-9-methyl-3-[(2-methyl-1H-imidazole-1-yl)methyl]-4H-carbazol-4-one of Formula-(I) from 1,2,3,9-tetrahydro-9-methyl-4H-carbazol-4-one of Formula-(IV) involves reaction of Formula (IV) with HNR1R2 salt and paraformaldehyde, where R1,R2 are independently alkyl groups or together forms a cyclic alkyl group, in a solvent system of acetic acid and hydrocarbon solvent to form a crude mixture of intermediate compounds of Formula (III) and (VIII), which is converted to ondansetron (Formula (I)) without isolation by reaction with 2­methyimidazole in a suitable solvent system in the same pot.
(FR) L'invention concerne un procédé industriel monotope pour la préparation de la 1,2,3,9-tétrahydro-9-méthyl-3-[(2-méthyl-1H-imidazole-1-yl)méthyl]-4H-carbazol-4-one de formule (I), à partir de la 1,2,3,9-tétrahydro-9-méthyl-4H-carbazol-4-one de formule (IV). Ledit procédé implique de faire réagir le composé de formule (IV) avec un sel HNR1R2 et du paraformaldéhyde, R1,R2 étant indépendamment des groupes alkyle ou formant ensemble un groupe alkyle cyclique, dans un système de solvants à base d'acide acétique et de solvant hydrocarboné pour former un mélange brut de composés intermédiaires de formules (III) et (VIII), ce dernier étant converti, sans être isolé, en ondansetron de formule (I), par réaction monotope avec le 2-méthylimidazole dans un système de solvants appropriés.
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