ES2151834B1 - Procedimiento para preparar n,n,6-trimetil-2-(4-metilfenil)-imidazo-(1,2-a)-piridina-3-acetamida y sus sales. - Google Patents
Procedimiento para preparar n,n,6-trimetil-2-(4-metilfenil)-imidazo-(1,2-a)-piridina-3-acetamida y sus sales.Info
- Publication number
- ES2151834B1 ES2151834B1 ES009801694A ES9801694A ES2151834B1 ES 2151834 B1 ES2151834 B1 ES 2151834B1 ES 009801694 A ES009801694 A ES 009801694A ES 9801694 A ES9801694 A ES 9801694A ES 2151834 B1 ES2151834 B1 ES 2151834B1
- Authority
- ES
- Spain
- Prior art keywords
- imidazo
- acetamide
- trimethyl
- salts
- procedure
- 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.)
- Expired - Fee Related
Links
- 238000000034 method Methods 0.000 title abstract 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- 239000003638 chemical reducing agent Substances 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- -1 hydroxy ester Chemical class 0.000 abstract 1
- 150000007975 iminium salts Chemical class 0.000 abstract 1
- 238000011065 in-situ storage Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- ZAFYATHCZYHLPB-UHFFFAOYSA-N zolpidem Chemical compound N1=C2C=CC(C)=CN2C(CC(=O)N(C)C)=C1C1=CC=C(C)C=C1 ZAFYATHCZYHLPB-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Procedimiento para preparar n,n,6-trimetil-2-(4-metilfenil)- imidazo-[1,2-a]-piridina-3-acetamida y sus sales. Comprende reducir el hidroxiéster de fórmula (X) haciéndolo reaccionar en DMF sucesivamente con una sal de iminio de fórmula (XIII) formada "in situ" con cloruro de tionilo y dimetilformamida, y reducción subsiguiente con un reductor apropiado para formar el éster de fórmula (XII), que después se hace reaccionar con dimetilamina en un medio solvente polihidroxilado y a una temperatura adecuada.
Priority Applications (27)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ES009801694A ES2151834B1 (es) | 1998-08-06 | 1998-08-06 | Procedimiento para preparar n,n,6-trimetil-2-(4-metilfenil)-imidazo-(1,2-a)-piridina-3-acetamida y sus sales. |
CZ2001360A CZ292446B6 (cs) | 1998-08-06 | 1999-08-04 | Způsob přípravy N,N,6-trimethyl-2-(4-methylfenyl)imidazo[1,2-a]pyridin-3-acetamidu a jeho solí |
RU2001106627/04A RU2221797C2 (ru) | 1998-08-06 | 1999-08-04 | Способ получения n,n,6-триметил-2-(4-метилфенил)-имидазо-[1,2-а]-пиридин-3-ацетамида и его солей |
AT99938403T ATE234836T1 (de) | 1998-08-06 | 1999-08-04 | Verfahren zur herstellung von n,n,6-trimethyl-2- (4-methylphenyl)-imidazo-(1,2-a)-pridin-3- acetamid und salzen davon |
EP99938403A EP1104765B2 (en) | 1998-08-06 | 1999-08-04 | Process for preparing n,n,6- trimethyl-2 -(4-methylphenyl)- imidazo-[1,2-a] -pyridine-3- acetamide and salts thereof |
DK99938403T DK1104765T4 (da) | 1998-08-06 | 1999-08-04 | Fremgangsmåde til fremstilling af N,N,6-trimethyl-2-(4-methylphenyl)-imidazo-[1,2-a]-pyridin-3-acetamid og salte deraf |
US09/762,205 US6407240B1 (en) | 1998-08-06 | 1999-08-04 | Process for preparing N,N,6- trimethyl-2-(4-methylphenyl)-imidazo- [1,2-a]-pyridine- 3-acetamide and salts thereof |
IL14113399A IL141133A (en) | 1998-08-06 | 1999-08-04 | Process for preparing N,N,6-trimethyl-2-(4-methylphenyl)-imidazo-Ä1,2-AÜ- pyridine-3-acetamide and salts thereof |
YUP-83/01A RS50103B (sr) | 1998-08-06 | 1999-08-04 | Postupak dobijanja n,n,6-trimetil-2-(4-metilfenil)-imidazo- (1,2-a)-piridin-3-acetamida i njegovih soli |
PT99938403T PT1104765E (pt) | 1998-08-06 | 1999-08-04 | Processo para a preparacao da n,n,6-trimetil-2-(4-metilfenil)-imidazo-¬1,2-a|-piridina-3-acetamida e dos respectivos sais |
HU0102936A HUP0102936A3 (en) | 1998-08-06 | 1999-08-04 | New process for preparing n,n,6- trimethyl-2 -(4-methylphenyl)- imidazo-[1,2-a] -pyridine-3-acetamide and salts thereof |
SK159-2001A SK283652B6 (sk) | 1998-08-06 | 1999-08-04 | Spôsob prípravy N,N,6-trimetyl-2-(4-metylfenyl)imidazo-[1,2- a]pyridín-3-acetamidu a jeho solí |
PL99346158A PL195888B1 (pl) | 1998-08-06 | 1999-08-04 | Sposób wytwarzania N,N-6-trimetylo-2-(4-metylofenylo)-imidazo-[1,2-a]-pirydyno-3-acetamidu i jego soli |
NZ510310A NZ510310A (en) | 1998-08-06 | 1999-08-04 | Process for preparing N,N,6- trimethyl-2-(4-methylphenyl)-imidazo[1,2-a]-pyridine-3-acetamide and its salts |
SI9930286T SI1104765T2 (sl) | 1998-08-06 | 1999-08-04 | Postopek za pripravo n,n,6-trimetil-2-(4-metilfenil)-imidazo-(1,2-a)-piridin-3-acetamida in njegovih soli |
KR10-2001-7001385A KR100492054B1 (ko) | 1998-08-06 | 1999-08-04 | N,N,6-트리메틸-2-(4-메틸페닐)-이미다조-[1,2-a]-피리딘-3-아세트아미드 및 이의 염의 제조방법 |
JP2000563654A JP3544944B2 (ja) | 1998-08-06 | 1999-08-04 | N,N,6−トリメチル−2−(4−メチルフェニル)−イミダゾ−[1,2−a]−ピリジン−3−アセトアミドおよびその塩の製造方法 |
PCT/ES1999/000250 WO2000008021A2 (es) | 1998-08-06 | 1999-08-04 | Procedimiento para preparar n,n,6- trimetil-2- (4-metilfenil)- imidazo-[1,2-a] -piridina-3- acetamida y sus sales |
AU52912/99A AU750302B2 (en) | 1998-08-06 | 1999-08-04 | Process for preparing N,N,6- trimethyl-2 -(4-methylphenyl)- imidazo-(1,2-A) -pyridine-3- acetamide and salts thereof |
CA002339594A CA2339594C (en) | 1998-08-06 | 1999-08-04 | Process for preparing n,n,6- trimethyl-2 -(4-methylphenyl)- imidazo-[1,2-a] -pyridine-3- acetamide and salts thereof |
DE69906088T DE69906088T3 (de) | 1998-08-06 | 1999-08-04 | Verfahren zur herstellung von n,n,6-trimethyl-2-(4-methylphenyl)-imidazo-[1,2-a]-pridin-3-acetamid und salzen davon |
ES99938403T ES2195598T5 (es) | 1998-08-06 | 1999-08-04 | Procedimiento para preparar n,n,6-trimetil-2-(4-metilfenil)-imidazo(1,2-a)piridina-3-acetamida y sus sales. |
NO20010613A NO319780B1 (no) | 1998-08-06 | 2001-02-05 | Fremgangsmate til fremstilling av N,N,6-trimetyl-2-(4-metylfenyl)-imidazo-[1,2-A]-pyridin-3-acetamid og salter derav |
IS5839A IS5839A (is) | 1998-08-06 | 2001-02-05 | Aðferð við að framleiða N,N 6-trímetýl-2-(4-metýlfenýl)-imídasó-[1,2-A]-pýridín-3-asetamíð og sölt þess |
ZA200101294A ZA200101294B (en) | 1998-08-06 | 2001-02-15 | Process for preparing N,N,6- trimethyl-2-(4-methylphenyl)-imidazo-[1,2-A]-pyridine-3-acetamide and salts thereof. |
HR20010158A HRP20010158B1 (en) | 1998-08-06 | 2001-03-06 | PROCESS FOR PREPARING N,N,6- TRIMETHYL-2-(4-METHYLPHENYL)-IMIDAZO-[1,2-a]-PYRIDINE-3-ACETAMIDE AND SALTS THEREOF |
HK01108425A HK1037624A1 (en) | 1998-08-06 | 2001-11-30 | Process for preparing n,n,6-trimethyl-2-(4-methylphenyl)-imidazo-[1,2-a]-pyridine-3-acetamide and salts thereof |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ES009801694A ES2151834B1 (es) | 1998-08-06 | 1998-08-06 | Procedimiento para preparar n,n,6-trimetil-2-(4-metilfenil)-imidazo-(1,2-a)-piridina-3-acetamida y sus sales. |
Publications (2)
Publication Number | Publication Date |
---|---|
ES2151834A1 ES2151834A1 (es) | 2001-01-01 |
ES2151834B1 true ES2151834B1 (es) | 2001-08-16 |
Family
ID=8304817
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ES009801694A Expired - Fee Related ES2151834B1 (es) | 1998-08-06 | 1998-08-06 | Procedimiento para preparar n,n,6-trimetil-2-(4-metilfenil)-imidazo-(1,2-a)-piridina-3-acetamida y sus sales. |
ES99938403T Expired - Lifetime ES2195598T5 (es) | 1998-08-06 | 1999-08-04 | Procedimiento para preparar n,n,6-trimetil-2-(4-metilfenil)-imidazo(1,2-a)piridina-3-acetamida y sus sales. |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ES99938403T Expired - Lifetime ES2195598T5 (es) | 1998-08-06 | 1999-08-04 | Procedimiento para preparar n,n,6-trimetil-2-(4-metilfenil)-imidazo(1,2-a)piridina-3-acetamida y sus sales. |
Country Status (26)
Country | Link |
---|---|
US (1) | US6407240B1 (es) |
EP (1) | EP1104765B2 (es) |
JP (1) | JP3544944B2 (es) |
KR (1) | KR100492054B1 (es) |
AT (1) | ATE234836T1 (es) |
AU (1) | AU750302B2 (es) |
CA (1) | CA2339594C (es) |
CZ (1) | CZ292446B6 (es) |
DE (1) | DE69906088T3 (es) |
DK (1) | DK1104765T4 (es) |
ES (2) | ES2151834B1 (es) |
HK (1) | HK1037624A1 (es) |
HR (1) | HRP20010158B1 (es) |
HU (1) | HUP0102936A3 (es) |
IL (1) | IL141133A (es) |
IS (1) | IS5839A (es) |
NO (1) | NO319780B1 (es) |
NZ (1) | NZ510310A (es) |
PL (1) | PL195888B1 (es) |
PT (1) | PT1104765E (es) |
RS (1) | RS50103B (es) |
RU (1) | RU2221797C2 (es) |
SI (1) | SI1104765T2 (es) |
SK (1) | SK283652B6 (es) |
WO (1) | WO2000008021A2 (es) |
ZA (1) | ZA200101294B (es) |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ES2151834B1 (es) † | 1998-08-06 | 2001-08-16 | Sint Quimica Sa | Procedimiento para preparar n,n,6-trimetil-2-(4-metilfenil)-imidazo-(1,2-a)-piridina-3-acetamida y sus sales. |
ES2248154T3 (es) * | 1999-11-22 | 2006-03-16 | Egis Gyogyszergyar Rt. | Procedimiento para la preparacion de 6-metil-2-(4-metil-fenil)-imidazo(1,2-a)-piridina-3-(n,n-dimetil-acetamida) y productos intermedios. |
IT1318624B1 (it) * | 2000-07-14 | 2003-08-27 | Dinamite Dipharma S P A In For | Processo per la preparazione di 2-fenil-imidazo (1,2-a)piridin-3-acetammidi. |
US6596731B2 (en) | 2001-03-27 | 2003-07-22 | Hoffmann-La Roche Inc. | Substituted imidazo[1,2-A] pyridine derivatives |
US6861525B2 (en) * | 2002-07-15 | 2005-03-01 | Scinopharm Taiwan, Ltd. | Process for the preparation imidazo[1,2-A]pyridine-3-acetamides |
AU2003297153B2 (en) | 2002-12-18 | 2010-06-10 | Mallinckrodt Inc. | Synthesis of heteroaryl acetamides |
CN1972939A (zh) * | 2004-06-22 | 2007-05-30 | 马林克罗特公司 | 由具有减少的水含量的反应混合物合成杂芳基乙酰胺 |
WO2007040995A1 (en) * | 2005-10-03 | 2007-04-12 | Mallinckrodt Inc. | Process for preparing zolpidem hemitartrate and tartrate polymorphs |
EP1803722A1 (en) * | 2006-01-03 | 2007-07-04 | Ferrer Internacional, S.A. | Imidazo[1,2-a]pyridin-3-yl-acetic acid hydrazides, processes for their preparation and pharmaceutical uses thereof |
US20080145425A1 (en) * | 2006-12-15 | 2008-06-19 | Pliva Research & Development Limited | Pharmaceutical composition of zolpidem |
CN103360387B (zh) * | 2012-03-28 | 2016-12-14 | 江苏豪森药业集团有限公司 | 一种制备化合物唑吡坦的方法 |
CN104610253B (zh) * | 2015-01-26 | 2016-11-16 | 郑州大学 | 2‑三氟甲基‑2‑羟基‑2‑(2‑芳基吡啶并[1,2‑α]咪唑)乙酸酯类化合物 |
CN114105974A (zh) * | 2020-08-27 | 2022-03-01 | 鲁南制药集团股份有限公司 | 一种唑吡坦的制备方法 |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2600650B1 (fr) * | 1986-06-27 | 1988-09-09 | Synthelabo | Procede de preparation d'imidazopyridines et composes intermediaires |
ES2151834B1 (es) † | 1998-08-06 | 2001-08-16 | Sint Quimica Sa | Procedimiento para preparar n,n,6-trimetil-2-(4-metilfenil)-imidazo-(1,2-a)-piridina-3-acetamida y sus sales. |
-
1998
- 1998-08-06 ES ES009801694A patent/ES2151834B1/es not_active Expired - Fee Related
-
1999
- 1999-08-04 PT PT99938403T patent/PT1104765E/pt unknown
- 1999-08-04 SK SK159-2001A patent/SK283652B6/sk not_active IP Right Cessation
- 1999-08-04 IL IL14113399A patent/IL141133A/xx not_active IP Right Cessation
- 1999-08-04 JP JP2000563654A patent/JP3544944B2/ja not_active Expired - Fee Related
- 1999-08-04 DK DK99938403T patent/DK1104765T4/da active
- 1999-08-04 AU AU52912/99A patent/AU750302B2/en not_active Ceased
- 1999-08-04 US US09/762,205 patent/US6407240B1/en not_active Expired - Fee Related
- 1999-08-04 CZ CZ2001360A patent/CZ292446B6/cs not_active IP Right Cessation
- 1999-08-04 NZ NZ510310A patent/NZ510310A/xx unknown
- 1999-08-04 RS YUP-83/01A patent/RS50103B/sr unknown
- 1999-08-04 KR KR10-2001-7001385A patent/KR100492054B1/ko not_active IP Right Cessation
- 1999-08-04 EP EP99938403A patent/EP1104765B2/en not_active Expired - Lifetime
- 1999-08-04 RU RU2001106627/04A patent/RU2221797C2/ru not_active IP Right Cessation
- 1999-08-04 ES ES99938403T patent/ES2195598T5/es not_active Expired - Lifetime
- 1999-08-04 PL PL99346158A patent/PL195888B1/pl not_active IP Right Cessation
- 1999-08-04 HU HU0102936A patent/HUP0102936A3/hu unknown
- 1999-08-04 WO PCT/ES1999/000250 patent/WO2000008021A2/es active IP Right Grant
- 1999-08-04 SI SI9930286T patent/SI1104765T2/sl unknown
- 1999-08-04 AT AT99938403T patent/ATE234836T1/de not_active IP Right Cessation
- 1999-08-04 CA CA002339594A patent/CA2339594C/en not_active Expired - Fee Related
- 1999-08-04 DE DE69906088T patent/DE69906088T3/de not_active Expired - Lifetime
-
2001
- 2001-02-05 IS IS5839A patent/IS5839A/is unknown
- 2001-02-05 NO NO20010613A patent/NO319780B1/no not_active IP Right Cessation
- 2001-02-15 ZA ZA200101294A patent/ZA200101294B/en unknown
- 2001-03-06 HR HR20010158A patent/HRP20010158B1/xx not_active IP Right Cessation
- 2001-11-30 HK HK01108425A patent/HK1037624A1/xx not_active IP Right Cessation
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
EC2A | Search report published |
Date of ref document: 20010101 Kind code of ref document: A1 Effective date: 20010101 |
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FD1A | Patent lapsed |
Effective date: 20100412 |