WO2003050092A3 - Process for the preparation of tofisopam and new intermediates - Google Patents

Process for the preparation of tofisopam and new intermediates Download PDF

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Publication number
WO2003050092A3
WO2003050092A3 PCT/HU2002/000141 HU0200141W WO03050092A3 WO 2003050092 A3 WO2003050092 A3 WO 2003050092A3 HU 0200141 W HU0200141 W HU 0200141W WO 03050092 A3 WO03050092 A3 WO 03050092A3
Authority
WO
WIPO (PCT)
Prior art keywords
preparation
dimethoxy
tofisopam
new intermediates
formula
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/HU2002/000141
Other languages
French (fr)
Other versions
WO2003050092A2 (en
Inventor
Samu Erika Molnarne
Gyula Simig
Pal Vago
Zoltan Greff
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Egyt Gyogyszervegyeszeti Gyar
Egis Pharmaceuticals PLC
Original Assignee
Egyt Gyogyszervegyeszeti Gyar
Egis Pharmaceuticals PLC
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from HU0105326A external-priority patent/HU225411B1/en
Priority claimed from HU0105327A external-priority patent/HUP0105327A3/en
Application filed by Egyt Gyogyszervegyeszeti Gyar, Egis Pharmaceuticals PLC filed Critical Egyt Gyogyszervegyeszeti Gyar
Priority to EP02781451A priority Critical patent/EP1465879A2/en
Priority to AU2002348942A priority patent/AU2002348942A1/en
Priority to SK279-2004A priority patent/SK2792004A3/en
Publication of WO2003050092A2 publication Critical patent/WO2003050092A2/en
Publication of WO2003050092A3 publication Critical patent/WO2003050092A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/26—Radicals substituted by doubly bound oxygen or sulfur atoms or by two such atoms singly bound to the same carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
    • C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
    • C07C45/59—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in five-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
    • C07D243/02—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
    • C07D317/22—Radicals substituted by singly bound oxygen or sulfur atoms etherified

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention relates to a new process for the preparation of 1-(3,4-dimethoxy-phenyl)-4-methyl-5-ethyl-7,8-dimethoxy-5H-2,3-benzodizepine of Formula (I) which comprises reacting a compound of general Formula (II) (wherein R1 and R2 independently each stands for C1-4-alkyl or together form C2-6-alkylene) with hydrazine or a hydrate or salt thereof formed with an inorganic or organic acid. 1-(3,4-dimethoxy-phenyl)-4-methyl-5-ethyl-7,8-dimethoxy-5H-2,3-benzodiazepine of the Formula I is a known anxiolytic agent. The invention also relates to new intermediates and a process for the preparation thereof.
PCT/HU2002/000141 2001-12-13 2002-12-12 Process for the preparation of tofisopam and new intermediates Ceased WO2003050092A2 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP02781451A EP1465879A2 (en) 2001-12-13 2002-12-12 Process for the preparation of tofisopam and new intermediates
AU2002348942A AU2002348942A1 (en) 2001-12-13 2002-12-12 Process for the preparation of tofisopam and new intermediates
SK279-2004A SK2792004A3 (en) 2001-12-13 2002-12-12 Process for the preparation of tofisopam and new intermediates

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
HUP0105326 2001-12-13
HU0105326A HU225411B1 (en) 2001-12-13 2001-12-13 Process for producing tofisopam
HUP0105327 2001-12-13
HU0105327A HUP0105327A3 (en) 2001-12-13 2001-12-13 Process for the production of 3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]-pentane-2-one

Publications (2)

Publication Number Publication Date
WO2003050092A2 WO2003050092A2 (en) 2003-06-19
WO2003050092A3 true WO2003050092A3 (en) 2003-11-06

Family

ID=89979996

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/HU2002/000141 Ceased WO2003050092A2 (en) 2001-12-13 2002-12-12 Process for the preparation of tofisopam and new intermediates

Country Status (7)

Country Link
EP (1) EP1465879A2 (en)
AU (1) AU2002348942A1 (en)
BG (1) BG108801A (en)
CZ (1) CZ2004792A3 (en)
PL (1) PL370036A1 (en)
SK (1) SK2792004A3 (en)
WO (1) WO2003050092A2 (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
HU227044B1 (en) * 2002-12-16 2010-05-28 Egis Gyogyszergyar Nyilvanosan Process for producing 3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]-pentan-2-one
FR2996845A1 (en) * 2012-10-12 2014-04-18 Servier Lab NOVEL PROCESS FOR THE SYNTHESIS OF 3- (2-BROMO-4,5-DIMETHOXYPHENYL) PROPANENITRILE, AND APPLICATION TO THE SYNTHESIS OF IVABRADINE AND ITS SALTS OF ADDITION TO A PHARMACEUTICALLY ACCEPTABLE ACID

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2122070A1 (en) * 1970-11-06 1972-06-08 E GY T Gyogyszervegyeszeti Gyar, Budapest 1 Veratryl 4 methyl 5 ethyl 7,8 dimethoxy 2,3 diazabicyclo square brackets to 5,4,0 square brackets to undeca pentaen (1,3,6,8,10) and its use

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2122070A1 (en) * 1970-11-06 1972-06-08 E GY T Gyogyszervegyeszeti Gyar, Budapest 1 Veratryl 4 methyl 5 ethyl 7,8 dimethoxy 2,3 diazabicyclo square brackets to 5,4,0 square brackets to undeca pentaen (1,3,6,8,10) and its use

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
GATTA F ET AL: "Derivatives of 2,3-Benzodiazepine", FARMACO, EDIZIONE SCIENTIFICA, SOCIETA CHIMICA ITALIANA, PAVIA, IT, vol. 40, 1985, pages 942 - 955, XP009011786, ISSN: 0430-0920 *

Also Published As

Publication number Publication date
AU2002348942A1 (en) 2003-06-23
SK2792004A3 (en) 2004-11-03
CZ2004792A3 (en) 2004-12-15
EP1465879A2 (en) 2004-10-13
WO2003050092A2 (en) 2003-06-19
PL370036A1 (en) 2005-05-16
AU2002348942A8 (en) 2003-06-23
BG108801A (en) 2005-04-30

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