HRP20020405A2 - Method for the preparation of 5-carboxyphthalide - Google Patents
Method for the preparation of 5-carboxyphthalide Download PDFInfo
- Publication number
- HRP20020405A2 HRP20020405A2 HR20020405A HRP20020405A HRP20020405A2 HR P20020405 A2 HRP20020405 A2 HR P20020405A2 HR 20020405 A HR20020405 A HR 20020405A HR P20020405 A HRP20020405 A HR P20020405A HR P20020405 A2 HRP20020405 A2 HR P20020405A2
- Authority
- HR
- Croatia
- Prior art keywords
- carboxyphthalide
- terephthalic acid
- water
- oleum
- equivalents
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 18
- QTWUWCFGWYYRRL-UHFFFAOYSA-N 1-oxo-3h-2-benzofuran-5-carboxylic acid Chemical compound OC(=O)C1=CC=C2C(=O)OCC2=C1 QTWUWCFGWYYRRL-UHFFFAOYSA-N 0.000 title claims description 17
- 238000002360 preparation method Methods 0.000 title claims description 3
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 40
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 6
- 229920002866 paraformaldehyde Polymers 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 2
- 235000019256 formaldehyde Nutrition 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- -1 1-[3-(dimethylamino)propyl]-1-(fluorophenyl)-1,3-dihydro-5-isobenzofurancarbonitrile Chemical compound 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 3
- XEEGWTLAFIZLSF-UHFFFAOYSA-N 1-oxo-3h-2-benzofuran-5-carbonitrile Chemical compound N#CC1=CC=C2C(=O)OCC2=C1 XEEGWTLAFIZLSF-UHFFFAOYSA-N 0.000 description 3
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 3
- WSEQXVZVJXJVFP-HXUWFJFHSA-N (R)-citalopram Chemical compound C1([C@@]2(C3=CC=C(C=C3CO2)C#N)CCCN(C)C)=CC=C(F)C=C1 WSEQXVZVJXJVFP-HXUWFJFHSA-N 0.000 description 2
- 230000001430 anti-depressive effect Effects 0.000 description 2
- 239000000935 antidepressant agent Substances 0.000 description 2
- 229940005513 antidepressants Drugs 0.000 description 2
- 229960001653 citalopram Drugs 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- VUBKPUVOSWVXMI-UHFFFAOYSA-N 3-oxo-1h-2-benzofuran-5-carboxylic acid Chemical compound OC(=O)C1=CC=C2COC(=O)C2=C1 VUBKPUVOSWVXMI-UHFFFAOYSA-N 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229940124834 selective serotonin reuptake inhibitor Drugs 0.000 description 1
- 239000012896 selective serotonin reuptake inhibitor Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
- C07D307/88—Benzo [c] furans; Hydrogenated benzo [c] furans with one oxygen atom directly attached in position 1 or 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
- Indole Compounds (AREA)
- Seasonings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DKPA199901569 | 1999-11-01 | ||
| PCT/DK2000/000585 WO2001032642A1 (en) | 1999-11-01 | 2000-10-19 | Method for the preparation of 5-carboxyphthalide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20020405A2 true HRP20020405A2 (en) | 2004-02-29 |
Family
ID=8106151
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20020405A HRP20020405A2 (en) | 1999-11-01 | 2002-05-10 | Method for the preparation of 5-carboxyphthalide |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US6403813B1 (it) |
| EP (1) | EP1235819A1 (it) |
| JP (1) | JP2003513084A (it) |
| CN (1) | CN1187348C (it) |
| AR (1) | AR026063A1 (it) |
| AU (1) | AU7902400A (it) |
| BR (1) | BR0015471A (it) |
| CA (1) | CA2389379C (it) |
| HK (1) | HK1052702A1 (it) |
| HR (1) | HRP20020405A2 (it) |
| IT (1) | IT1319251B1 (it) |
| MX (1) | MXPA02004313A (it) |
| WO (1) | WO2001032642A1 (it) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EA004033B1 (ru) | 1999-04-14 | 2003-12-25 | Х.Лундбекк А/С | Способ получения циталопрама |
| ITMI991581A1 (it) * | 1999-06-25 | 2001-01-15 | Lundbeck & Co As H | Metodo per la preparazione di citalopram |
| AR026063A1 (es) | 1999-11-01 | 2002-12-26 | Lundbeck & Co As H | Metodo para la preparacion de 5-carboxiftalida. |
| ES2219095T3 (es) | 1999-12-28 | 2004-11-16 | H. Lundbeck A/S | Metodo para la preparacion de citalopram. |
| UA73336C2 (en) | 1999-12-30 | 2005-07-15 | Lundbeck & Co As H | A method for the preparation of 5-cyano-phtalid |
| ES2206177T3 (es) * | 2000-01-14 | 2004-05-16 | H. Lundbeck A/S | Metodo para la preparacion de 5-cianoftalida. |
| IT1317729B1 (it) † | 2000-01-18 | 2003-07-15 | Norpharma S P A | Procedimento per la preparazione della 5-carbossiftalide. |
| IES20010157A2 (en) | 2000-03-03 | 2002-03-06 | Lundbeck & Co As H | Method for the preparation of citalopram |
| GB0005477D0 (en) | 2000-03-07 | 2000-04-26 | Resolution Chemicals Limited | Process for the preparation of citalopram |
| IES20010206A2 (en) | 2000-03-13 | 2002-03-06 | Lundbeck & Co As H | Method for the preparation of citalopram |
| EP1265883A1 (en) * | 2000-03-13 | 2002-12-18 | H. Lundbeck A/S | Method for the preparation of citalopram |
| CZ20023100A3 (cs) * | 2000-03-13 | 2003-02-12 | H. Lundbeck A/S | Způsob výroby citalopramu |
| DE60101786T2 (de) | 2000-03-14 | 2004-07-15 | H. Lundbeck A/S, Valby | Verfahren zur herstellung von citalopram |
| AU2001244086A1 (en) * | 2000-03-16 | 2001-09-24 | H. Lundbeck A/S | Method for the preparation of 5-cyano-1-(4-fluorophenyl)-1,3-dihydroisobenzofurans |
| AR032455A1 (es) | 2000-05-12 | 2003-11-12 | Lundbeck & Co As H | Metodo para la preparacion de citalopram, un intermediario empleado en el metodo, un metodo para la preparacion del intermediario empleado en el metodo y composicion farmaceutica antidepresiva |
| CN1761659A (zh) | 2003-03-21 | 2006-04-19 | H·隆德贝克有限公司 | 用于制备西酞普兰和依他普仑的中间体 |
| AU2003223105A1 (en) * | 2003-03-24 | 2004-10-18 | Hetero Drugs Limited | Novel crystalline forms of (s)-citalopram oxalate |
| WO2006090409A1 (en) * | 2005-02-28 | 2006-08-31 | Kekule Pharma Ltd., | An improved process for the preparation of 5 - carboxyphthalide |
| CN106632183A (zh) * | 2016-12-07 | 2017-05-10 | 万全万特制药（厦门）有限公司 | 一种草酸艾司西酞普兰杂质的制备方法 |
| CN112062741A (zh) * | 2019-06-11 | 2020-12-11 | 太仓市茜泾化工有限公司 | 一种5-羧酸苯酞的制备方法 |
Family Cites Families (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1143702A (it) | 1965-03-18 | |||
| US3607884A (en) * | 1969-03-11 | 1971-09-21 | Mobil Oil Corp | Preparation of 5-carboxyphthalide in liquid sodium trioxide |
| DE2242007A1 (de) * | 1972-08-26 | 1974-03-14 | Basf Ag | Verfahren zur herstellung von phthalimidinen |
| GB1526331A (en) | 1976-01-14 | 1978-09-27 | Kefalas As | Phthalanes |
| DE2630927A1 (de) * | 1976-07-09 | 1978-01-19 | Basf Ag | Verfahren zur herstellung von phthalidcarbonsaeure-(5) |
| GB8419963D0 (en) | 1984-08-06 | 1984-09-12 | Lundbeck & Co As H | Intermediate compound and method |
| GB8814057D0 (en) | 1988-06-14 | 1988-07-20 | Lundbeck & Co As H | New enantiomers & their isolation |
| DE59003859D1 (de) | 1989-08-23 | 1994-01-27 | Alusuisse Lonza Services Ag | Sterilisierfähiger Verpackungsbehälter aus Kunststoff-Metall-Kunststoff-Verbundmaterial und Verfahren zu dessen Herstellung. |
| US5296507A (en) | 1990-09-06 | 1994-03-22 | H.Lundbeck A/S | Treatment of cerbrovascular disorders |
| DE19626659A1 (de) * | 1996-07-03 | 1998-01-08 | Basf Ag | Verfahren zur Herstellung von Phthaliden |
| DE19627697A1 (de) * | 1996-07-10 | 1998-01-15 | Basf Ag | Verfahren zur Herstellung von Phthaliden |
| DE69801764T2 (de) | 1997-07-08 | 2002-07-04 | Lundbeck & Co As H | Verfahren zur herstellung von citalopram |
| UA62985C2 (en) | 1997-11-10 | 2004-01-15 | Lunnbeck As H | A method for the preparation of citalopram |
| DE69714480T2 (de) | 1997-11-11 | 2003-03-06 | Lundbeck & Co As H | Verfahren zur Herstellung von Citalopram |
| PL199423B1 (pl) * | 1998-10-20 | 2008-09-30 | Lundbeck & Co As H | Sposób wytwarzania citalopramu |
| JP2002533450A (ja) | 1998-12-23 | 2002-10-08 | ハー・ルンドベック・アクチエゼルスカベット | ５−シアノフタリドの製造方法 |
| AR022329A1 (es) | 1999-01-29 | 2002-09-04 | Lundbeck & Co As H | Metodo para la preparacion de 5-cianoftalida |
| EA004033B1 (ru) | 1999-04-14 | 2003-12-25 | Х.Лундбекк А/С | Способ получения циталопрама |
| ITMI991581A1 (it) | 1999-06-25 | 2001-01-15 | Lundbeck & Co As H | Metodo per la preparazione di citalopram |
| ITMI991579A1 (it) | 1999-06-25 | 2001-01-15 | Lundbeck & Co As H | Metodo per la preparazione di citalopram |
| ES2229774T3 (es) | 1999-10-25 | 2005-04-16 | H. Lundbeck A/S | Metodo para la preparacion de citalopram. |
| AR026063A1 (es) | 1999-11-01 | 2002-12-26 | Lundbeck & Co As H | Metodo para la preparacion de 5-carboxiftalida. |
| US6310222B1 (en) | 1999-11-01 | 2001-10-30 | Sumika Fine Chemicals Co., Ltd. | Production method of 5-phthalancarbonitrile compound, intermediate therefor and production method of the intermediate |
| AU1130901A (en) | 1999-11-01 | 2001-05-14 | H. Lundbeck A/S | Method for the preparation of 5-carboxyphthalide |
| IT1317729B1 (it) * | 2000-01-18 | 2003-07-15 | Norpharma S P A | Procedimento per la preparazione della 5-carbossiftalide. |
| US6433196B1 (en) * | 2000-02-17 | 2002-08-13 | Sumika Fine Chemicals Co., Ltd. | Production method of citalopram, intermediate therefor and production method of the intermediate |
| IES20010143A2 (en) | 2000-02-24 | 2001-07-25 | Lundbeck & Co As H | Method for the preparation of citalopram |
| FR2805812A1 (fr) | 2000-02-24 | 2001-09-07 | Lundbeck & Co As H | Procede de preparation du citalopram |
| GB0005477D0 (en) | 2000-03-07 | 2000-04-26 | Resolution Chemicals Limited | Process for the preparation of citalopram |
| FI20011622A (fi) | 2000-08-18 | 2002-02-19 | Lundbeck & Co As H | Menetelmä sitalopraamin valmistamiseksi |
| TR200200018T1 (tr) | 2000-12-28 | 2002-06-21 | H. Lundbeck A/S | Saf sitalopram hazırlanması için yöntem. |
-
2000
- 2000-10-17 AR ARP000105451A patent/AR026063A1/es unknown
- 2000-10-19 EP EP00969234A patent/EP1235819A1/en not_active Withdrawn
- 2000-10-19 WO PCT/DK2000/000585 patent/WO2001032642A1/en active Application Filing
- 2000-10-19 BR BR0015471-7A patent/BR0015471A/pt not_active IP Right Cessation
- 2000-10-19 CA CA002389379A patent/CA2389379C/en not_active Expired - Fee Related
- 2000-10-19 US US09/692,653 patent/US6403813B1/en not_active Expired - Fee Related
- 2000-10-19 AU AU79024/00A patent/AU7902400A/en not_active Abandoned
- 2000-10-19 MX MXPA02004313A patent/MXPA02004313A/es unknown
- 2000-10-19 CN CNB008151431A patent/CN1187348C/zh not_active Expired - Fee Related
- 2000-10-19 JP JP2001534793A patent/JP2003513084A/ja not_active Withdrawn
- 2000-10-27 IT IT2000MI002342A patent/IT1319251B1/it active
-
2002
- 2002-05-06 US US10/140,361 patent/US6888009B2/en not_active Expired - Fee Related
- 2002-05-10 HR HR20020405A patent/HRP20020405A2/hr not_active Application Discontinuation
-
2003
- 2003-07-10 HK HK03104993A patent/HK1052702A1/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| WO2001032642A1 (en) | 2001-05-10 |
| AR026063A1 (es) | 2002-12-26 |
| IT1319251B1 (it) | 2003-09-26 |
| US6403813B1 (en) | 2002-06-11 |
| HK1052702A1 (en) | 2003-09-26 |
| EP1235819A1 (en) | 2002-09-04 |
| CA2389379A1 (en) | 2001-05-10 |
| MXPA02004313A (es) | 2002-11-07 |
| US20020165403A1 (en) | 2002-11-07 |
| CN1391567A (zh) | 2003-01-15 |
| US6888009B2 (en) | 2005-05-03 |
| AU7902400A (en) | 2001-05-14 |
| CN1187348C (zh) | 2005-02-02 |
| CA2389379C (en) | 2007-04-10 |
| ITMI20002342A1 (it) | 2002-04-27 |
| JP2003513084A (ja) | 2003-04-08 |
| BR0015471A (pt) | 2002-07-09 |
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