HUP0204342A2 - Process for producing 3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]-pentan-2-one - Google Patents

Process for producing 3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]-pentan-2-one

Info

Publication number
HUP0204342A2
HUP0204342A2 HU0204342A HUP0204342A HUP0204342A2 HU P0204342 A2 HUP0204342 A2 HU P0204342A2 HU 0204342 A HU0204342 A HU 0204342A HU P0204342 A HUP0204342 A HU P0204342A HU P0204342 A2 HUP0204342 A2 HU P0204342A2
Authority
HU
Hungary
Prior art keywords
formula
compound
general formula
carbon atoms
alkali metal
Prior art date
Application number
HU0204342A
Other languages
Hungarian (hu)
Inventor
dr. Samu Erika Molnárné
Gyula Simig
Original Assignee
EGIS Gyógyszergyár Rt.
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
Application filed by EGIS Gyógyszergyár Rt. filed Critical EGIS Gyógyszergyár Rt.
Priority to HU0204342A priority Critical patent/HU227044B1/en
Priority to AU2002361068A priority patent/AU2002361068A1/en
Priority to EP02791921A priority patent/EP1575890A1/en
Priority to SK70-2005A priority patent/SK702005A3/en
Priority to CZ2005388A priority patent/CZ2005388A3/en
Priority to PL376530A priority patent/PL376530A1/en
Priority to PCT/HU2002/000178 priority patent/WO2004054951A1/en
Priority to UAA200507059A priority patent/UA78634C2/en
Priority to EA200500966A priority patent/EA007788B1/en
Priority to JP2004559931A priority patent/JP4437093B2/en
Priority to KR1020057011012A priority patent/KR100936306B1/en
Publication of HU0204342D0 publication Critical patent/HU0204342D0/en
Priority to PCT/HU2003/000104 priority patent/WO2004054952A1/en
Priority to AU2003292449A priority patent/AU2003292449A1/en
Publication of HUP0204342A2 publication Critical patent/HUP0204342A2/en
Publication of HUP0204342A3 publication Critical patent/HUP0204342A3/en
Priority to BG109230A priority patent/BG109230A/en
Publication of HU227044B1 publication Critical patent/HU227044B1/en

Links

Classifications

    • 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
    • C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
    • C07C45/455—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation with carboxylic acids or their derivatives
    • 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
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
    • C07C45/515—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an acetalised, ketalised hemi-acetalised, or hemi-ketalised hydroxyl group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/29—Saturated compounds containing keto groups bound to rings
    • C07C49/35—Saturated compounds containing keto groups bound to rings containing ether groups, groups, groups, or groups

Landscapes

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

Abstract

A találmány tárgya eljárás az (I) képletű 3-[2-(3,4-dimetoxi-benzoil)-4,5-dimetoxi-fenil]-pentán-2-on előállítására valamely (II) általánosképletű vegyületből kiindulva (mely képletben Rl és R2 jelentésekülön-külön 1-4 szénatomos alkilcsoport, vagy Rl és R2 együtt 2-6szénatomos alkilén-csoportot képez) oly módon, hogy a) a (II)általános képletű vegyületben levő brómatomot alkálifém- vagymagnéziumatomra cseréli le; a kapott alkálifém- vagymagnéziumvegyületet hozzávetőlegesen ekvimoláris mennyiségű (IIIa)általános képletű savamiddal hozzák reakcióba (mely képletben R3 és R4jelentése 1-4 szénatomos alkilcsoport), majd a kapott (IV) általánosképletű vegyületet (mely képletben R1 és R2 jelentése a fent megadott)hidrolizálják; vagy b) a (II) általános képletű vegyületben levőbrómatomot alkálifém- vagy magnéziumatomra cserélik le; a kapottalkálifém- vagy magnéziumvegyületet hozzávetőlegesen ekvimolárismennyiségű (IIIb) általános képletű észterrel hozzák reakcióba (melyképletben R5 jelentése 1-4 szénatomos alkilcsoport), majd a kapott(IV) általános képletű vegyületet hidrolizálják. Az (I) képletűvegyület a tofisopam nemzetközi szabadnevű (INN) anxiolitikumelőállításánál felhasználható gyógyszeripari közbenső termék. ÓThe subject of the invention is a process for the production of 3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]-pentan-2-one of formula (I) starting from a compound of formula (II) (in which formula Rl and R2 is individually an alkyl group with 1 to 4 carbon atoms, or R1 and R2 together form an alkylene group with 2 to 6 carbon atoms) in such a way that a) the bromine atom in the compound of general formula (II) is replaced by an alkali metal or magnesium atom; the resulting alkali metal or magnesium compound is reacted with an approximately equimolar amount of an acid amide of general formula (IIIa) (in which formula R3 and R4 are alkyl groups with 1-4 carbon atoms), then the resulting compound of general formula (IV) (in which formula R1 and R2 have the meanings given above) is hydrolyzed; or b) the bromine atom in the compound of general formula (II) is replaced by an alkali metal or magnesium atom; the resulting alkali metal or magnesium compound is reacted with an approximately equimolar amount of ester of general formula (IIIb) (in which formula R5 is an alkyl group with 1-4 carbon atoms), and then the resulting compound of general formula (IV) is hydrolyzed. The compound of formula (I) is a pharmaceutical intermediate product that can be used in the production of the anxiolytic tofisopam international non-proprietary name (INN). HE

HU0204342A 2002-12-16 2002-12-16 Process for producing 3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]-pentan-2-one HU227044B1 (en)

Priority Applications (14)

Application Number Priority Date Filing Date Title
HU0204342A HU227044B1 (en) 2002-12-16 2002-12-16 Process for producing 3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]-pentan-2-one
UAA200507059A UA78634C2 (en) 2002-12-16 2002-12-31 A process for the preparation of 3-[2-(3,4-dimethoxy-benzoyl)-4,5-dimethoxy-pheny]]-pentan-2-one
KR1020057011012A KR100936306B1 (en) 2002-12-16 2002-12-31 Process for the preparation of 3-[2-3,4-dimethoxy-benzoyl-4,5-dimethoxy-phenyl]-pentan-2-one
SK70-2005A SK702005A3 (en) 2002-12-16 2002-12-31 Process for the preparation of 3-[2-(3,4-dimethoxy-benzoyl)-4,5- dimethoxy-phenyl]-pentan-2-one
CZ2005388A CZ2005388A3 (en) 2002-12-16 2002-12-31 Process for preparing 3-[2-(3,4-dimethoxy-benzoyl)-4,5-dimethoxy-phenyl]-pentan-2-one
PL376530A PL376530A1 (en) 2002-12-16 2002-12-31 Process for the preparation of 3-[2-(3,4-dimethoxy-benzoyl)-4,5-dimethoxy-phenyl]-pentan-2-one
PCT/HU2002/000178 WO2004054951A1 (en) 2002-12-16 2002-12-31 Process for the preparation of 3-[2-(3,4-dimethoxy-benzoyl)-4,5-dimethoxy-phenyl]-pentan-2-one
AU2002361068A AU2002361068A1 (en) 2002-12-16 2002-12-31 Process for the preparation of 3-(2-(3,4-dimethoxy-benzoyl)-4,5-dimethoxy-phenyl)-pentan-2-one
EA200500966A EA007788B1 (en) 2002-12-16 2002-12-31 Process for the preparation of 3-[2-(3,4-dimethoxy-benzoyl)-4,5-dimethoxy-phenyl]pentan-2-one
JP2004559931A JP4437093B2 (en) 2002-12-16 2002-12-31 Preparation of 3- [2- (3,4-dimethoxy-benzoyl) -4,5-dimethoxy-phenyl] -pentan-2-one
EP02791921A EP1575890A1 (en) 2002-12-16 2002-12-31 Process for the preparation of 3- 2-(3,4-dimethoxy-benzoyl)- 4,5-dimethoxy-phenyl -pentan-2-one
PCT/HU2003/000104 WO2004054952A1 (en) 2002-12-16 2003-12-16 Process for the preparation of 3-[2-(3,4-dimethoxybenzoyl)-4,5- dimethoxyphenyl] -pentan-2-one
AU2003292449A AU2003292449A1 (en) 2002-12-16 2003-12-16 Process for the preparation of 3-(2-(3,4-dimethoxybenzoyl)-4,5- dimethoxyphenyl) -pentan-2-one
BG109230A BG109230A (en) 2002-12-16 2005-07-14 Process for the preparation of 3-[2-(3,4-dimethoxy-benzoyl)-4,5-dimethoxy-phenyl]-pentan-2-one

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
HU0204342A HU227044B1 (en) 2002-12-16 2002-12-16 Process for producing 3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]-pentan-2-one

Publications (4)

Publication Number Publication Date
HU0204342D0 HU0204342D0 (en) 2003-02-28
HUP0204342A2 true HUP0204342A2 (en) 2004-07-28
HUP0204342A3 HUP0204342A3 (en) 2004-11-29
HU227044B1 HU227044B1 (en) 2010-05-28

Family

ID=89981000

Family Applications (1)

Application Number Title Priority Date Filing Date
HU0204342A HU227044B1 (en) 2002-12-16 2002-12-16 Process for producing 3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]-pentan-2-one

Country Status (12)

Country Link
EP (1) EP1575890A1 (en)
JP (1) JP4437093B2 (en)
KR (1) KR100936306B1 (en)
AU (2) AU2002361068A1 (en)
BG (1) BG109230A (en)
CZ (1) CZ2005388A3 (en)
EA (1) EA007788B1 (en)
HU (1) HU227044B1 (en)
PL (1) PL376530A1 (en)
SK (1) SK702005A3 (en)
UA (1) UA78634C2 (en)
WO (2) WO2004054951A1 (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100714181B1 (en) * 2005-07-04 2007-05-04 주식회사 자동기 Fuel supply system for snow removing apparatus
CN104098482B (en) * 2013-04-12 2016-04-20 江苏英力科技发展有限公司 A kind of 3,4-dimethoxy-N, the preparation method of N-dimethyl benzamide
CN104262128B (en) * 2014-09-04 2016-04-13 山东金城医药化工股份有限公司 The preparation method of Tofisopam intermediate

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
HU194529B (en) * 1984-07-20 1988-02-29 Gyogyszerkutato Intezet New process for producing 2-aroyl-phenylacetone-derivatives
PL370036A1 (en) * 2001-12-13 2005-05-16 Egis Gyogyszergyar Rt. Process for the preparation of tofisopam and new intermediates

Also Published As

Publication number Publication date
PL376530A1 (en) 2006-01-09
SK702005A3 (en) 2005-09-08
UA78634C2 (en) 2007-04-10
WO2004054951A1 (en) 2004-07-01
EA200500966A1 (en) 2005-12-29
HUP0204342A3 (en) 2004-11-29
BG109230A (en) 2006-04-28
JP4437093B2 (en) 2010-03-24
KR100936306B1 (en) 2010-01-12
HU227044B1 (en) 2010-05-28
JP2006509814A (en) 2006-03-23
KR20050085686A (en) 2005-08-29
EP1575890A1 (en) 2005-09-21
WO2004054952A1 (en) 2004-07-01
HU0204342D0 (en) 2003-02-28
AU2003292449A1 (en) 2004-07-09
AU2002361068A1 (en) 2004-07-09
EA007788B1 (en) 2007-02-27
CZ2005388A3 (en) 2005-09-14

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Legal Events

Date Code Title Description
HC9A Change of name, address

Owner name: EGIS GYOGYSZERGYAR NYILVANOSAN MUEKOEDOE RESZV, HU

Free format text: FORMER OWNER(S): EGIS GYOGYSZERGYAR RT., HU

MM4A Lapse of definitive patent protection due to non-payment of fees