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-oneInfo
- 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
Links
- ZWUMDFWFKWDFBI-UHFFFAOYSA-N 3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]pentan-2-one Chemical compound CCC(C(C)=O)C1=CC(OC)=C(OC)C=C1C(=O)C1=CC=C(OC)C(OC)=C1 ZWUMDFWFKWDFBI-UHFFFAOYSA-N 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 6
- 229910052783 alkali metal Inorganic materials 0.000 abstract 4
- 150000001340 alkali metals Chemical class 0.000 abstract 4
- 125000004432 carbon atom Chemical group C* 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical group [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract 2
- 239000002050 international nonproprietary name Substances 0.000 abstract 2
- 229910052749 magnesium Inorganic materials 0.000 abstract 2
- 150000002681 magnesium compounds Chemical class 0.000 abstract 2
- RUJBDQSFYCKFAA-UHFFFAOYSA-N Tofisopam Chemical compound N=1N=C(C)C(CC)C2=CC(OC)=C(OC)C=C2C=1C1=CC=C(OC)C(OC)=C1 RUJBDQSFYCKFAA-UHFFFAOYSA-N 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 239000002249 anxiolytic agent Substances 0.000 abstract 1
- 230000000949 anxiolytic effect Effects 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 239000012450 pharmaceutical intermediate Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 229960002501 tofisopam Drugs 0.000 abstract 1
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
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)
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)
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 |
-
2002
- 2002-12-16 HU HU0204342A patent/HU227044B1/en not_active IP Right Cessation
- 2002-12-31 EP EP02791921A patent/EP1575890A1/en not_active Withdrawn
- 2002-12-31 WO PCT/HU2002/000178 patent/WO2004054951A1/en active Application Filing
- 2002-12-31 PL PL376530A patent/PL376530A1/en not_active IP Right Cessation
- 2002-12-31 SK SK70-2005A patent/SK702005A3/en unknown
- 2002-12-31 UA UAA200507059A patent/UA78634C2/en unknown
- 2002-12-31 AU AU2002361068A patent/AU2002361068A1/en not_active Abandoned
- 2002-12-31 CZ CZ2005388A patent/CZ2005388A3/en unknown
- 2002-12-31 EA EA200500966A patent/EA007788B1/en not_active IP Right Cessation
- 2002-12-31 KR KR1020057011012A patent/KR100936306B1/en not_active IP Right Cessation
- 2002-12-31 JP JP2004559931A patent/JP4437093B2/en not_active Expired - Fee Related
-
2003
- 2003-12-16 WO PCT/HU2003/000104 patent/WO2004054952A1/en not_active Application Discontinuation
- 2003-12-16 AU AU2003292449A patent/AU2003292449A1/en not_active Abandoned
-
2005
- 2005-07-14 BG BG109230A patent/BG109230A/en unknown
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 |