CA2397497C - Process for the preparation of 5-carboxyphthalide and its use for the production of citalopram - Google Patents
Process for the preparation of 5-carboxyphthalide and its use for the production of citalopram Download PDFInfo
- Publication number
- CA2397497C CA2397497C CA2397497A CA2397497A CA2397497C CA 2397497 C CA2397497 C CA 2397497C CA 2397497 A CA2397497 A CA 2397497A CA 2397497 A CA2397497 A CA 2397497A CA 2397497 C CA2397497 C CA 2397497C
- Authority
- CA
- Canada
- Prior art keywords
- process according
- carboxyphthalide
- acid
- mixture
- temperature
- 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
- 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 abstract description 39
- 238000000034 method Methods 0.000 title claims abstract description 39
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 229960001653 citalopram Drugs 0.000 title claims description 4
- 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 title claims description 3
- 238000004519 manufacturing process Methods 0.000 title description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims abstract description 42
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 39
- 239000000203 mixture Substances 0.000 claims abstract description 37
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000011541 reaction mixture Substances 0.000 claims abstract description 9
- 238000010438 heat treatment Methods 0.000 claims abstract description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 40
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 14
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 claims description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 10
- 230000015572 biosynthetic process Effects 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 229960000583 acetic acid Drugs 0.000 claims description 5
- 239000012362 glacial acetic acid Substances 0.000 claims description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 5
- 238000003786 synthesis reaction Methods 0.000 claims description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 239000002243 precursor Substances 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 2
- 238000006386 neutralization reaction Methods 0.000 claims description 2
- 229920002866 paraformaldehyde Polymers 0.000 claims description 2
- 238000007865 diluting Methods 0.000 claims 1
- 230000003472 neutralizing effect Effects 0.000 claims 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 1
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 1
- 159000000000 sodium salts Chemical class 0.000 claims 1
- 238000003756 stirring Methods 0.000 description 19
- 238000007792 addition Methods 0.000 description 16
- 239000008367 deionised water Substances 0.000 description 14
- 229910021641 deionized water Inorganic materials 0.000 description 14
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 12
- 239000000725 suspension Substances 0.000 description 10
- 239000007787 solid Substances 0.000 description 9
- 238000004128 high performance liquid chromatography Methods 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 238000001914 filtration Methods 0.000 description 5
- 239000002585 base Substances 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- WSEQXVZVJXJVFP-UHFFFAOYSA-N 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile Chemical compound O1CC2=CC(C#N)=CC=C2C1(CCCN(C)C)C1=CC=C(F)C=C1 WSEQXVZVJXJVFP-UHFFFAOYSA-N 0.000 description 1
- VXDNPRHLFXHOKH-UHFFFAOYSA-N 2-(hydroxymethyl)terephthalic acid Chemical compound OCC1=CC(C(O)=O)=CC=C1C(O)=O VXDNPRHLFXHOKH-UHFFFAOYSA-N 0.000 description 1
- UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical class C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 description 1
- IAXHJVPHUODTTC-UHFFFAOYSA-N 2-benzofuran-1-carboxylic acid Chemical compound C1=CC=CC2=C(C(=O)O)OC=C21 IAXHJVPHUODTTC-UHFFFAOYSA-N 0.000 description 1
- FRHBUJIXNLOLOF-UHFFFAOYSA-N 3-oxo-1h-2-benzofuran-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)OC(=O)C2=C1 FRHBUJIXNLOLOF-UHFFFAOYSA-N 0.000 description 1
- -1 5-carboxy phthalide methyl ester Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000013341 scale-up Methods 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 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
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D307/83—Oxygen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- 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)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pain & Pain Management (AREA)
- Life Sciences & Earth Sciences (AREA)
- Psychiatry (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Seasonings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2000MI000050A IT1317729B1 (it) | 2000-01-18 | 2000-01-18 | Procedimento per la preparazione della 5-carbossiftalide. |
| ITMI2000A000050 | 2000-01-18 | ||
| US09/690,301 US6458973B1 (en) | 2000-01-18 | 2000-10-17 | Process for the preparation of 5-carboxyphthalide |
| PCT/EP2001/000617 WO2001053284A1 (en) | 2000-01-18 | 2001-01-17 | Process for the preparation of 5-carboxyphthalide and its use for the production of citalopram |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2397497A1 CA2397497A1 (en) | 2001-07-26 |
| CA2397497C true CA2397497C (en) | 2010-07-06 |
Family
ID=26332721
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2397497A Expired - Fee Related CA2397497C (en) | 2000-01-18 | 2001-01-17 | Process for the preparation of 5-carboxyphthalide and its use for the production of citalopram |
Country Status (21)
| Country | Link |
|---|---|
| US (4) | US6458973B1 (https=) |
| EP (2) | EP1118614B2 (https=) |
| JP (1) | JP4558182B2 (https=) |
| CN (1) | CN1184220C (https=) |
| AT (1) | ATE219489T1 (https=) |
| AU (1) | AU779581B2 (https=) |
| BG (1) | BG65763B1 (https=) |
| BR (1) | BR0107853A (https=) |
| CA (1) | CA2397497C (https=) |
| DE (1) | DE60000226T3 (https=) |
| DK (1) | DK1118614T4 (https=) |
| ES (1) | ES2178626T5 (https=) |
| HK (1) | HK1042290B (https=) |
| HU (1) | HUP0204187A3 (https=) |
| IT (1) | IT1317729B1 (https=) |
| MX (1) | MXPA02007031A (https=) |
| PL (1) | PL356563A1 (https=) |
| PT (1) | PT1118614E (https=) |
| RO (1) | RO121737B1 (https=) |
| WO (1) | WO2001053284A1 (https=) |
| ZA (1) | ZA200205475B (https=) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR026063A1 (es) * | 1999-11-01 | 2002-12-26 | Lundbeck & Co As H | Metodo para la preparacion de 5-carboxiftalida. |
| 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 |
| CN1427835A (zh) * | 2000-03-13 | 2003-07-02 | H·隆德贝克有限公司 | 5－取代的1－(4－氟苯基)－1,3－二氢异苯并呋喃的分步烷基化 |
| 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 |
| US7687645B2 (en) * | 2003-03-21 | 2010-03-30 | H. Lundbeck A/S | Intermediates for the preparation of citalopram and escitalopram |
| US20050154052A1 (en) * | 2003-03-24 | 2005-07-14 | Hetero Drugs Limited | Novel crystalline forms of (s)-citalopram oxalate |
| CN100569765C (zh) | 2003-12-19 | 2009-12-16 | 杭州民生药业集团有限公司 | 西酞普兰中间体晶体碱 |
| WO2006090409A1 (en) * | 2005-02-28 | 2006-08-31 | Kekule Pharma Ltd., | An improved process for the preparation of 5 - carboxyphthalide |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3607884A (en) * | 1969-03-11 | 1971-09-21 | Mobil Oil Corp | Preparation of 5-carboxyphthalide in liquid sodium trioxide |
| US3976751A (en) † | 1974-10-21 | 1976-08-24 | Allied Chemical Corporation | Stabilization of liquid sulfur trioxide |
| DE2630927A1 (de) | 1976-07-09 | 1978-01-19 | Basf Ag | Verfahren zur herstellung von phthalidcarbonsaeure-(5) |
| DE3605716A1 (de) | 1986-02-22 | 1987-09-03 | Henkel Kgaa | Verwendung von unloeslichen schmutzsammlern zur regenerierung von wasch- und reinigungsloesungen |
| WO1998019513A2 (en) * | 1997-07-08 | 1998-05-14 | H. Lundbeck A/S | Method for the preparation of citalopram |
| CA2291134C (en) * | 1998-10-20 | 2006-05-23 | H. Lundbeck A/S | Method for the preparation of citalopram |
| AR026063A1 (es) * | 1999-11-01 | 2002-12-26 | Lundbeck & Co As H | Metodo para la preparacion de 5-carboxiftalida. |
| AU1130901A (en) | 1999-11-01 | 2001-05-14 | H. Lundbeck A/S | Method for the preparation of 5-carboxyphthalide |
| GB0005477D0 (en) | 2000-03-07 | 2000-04-26 | Resolution Chemicals Limited | Process for the preparation of citalopram |
-
2000
- 2000-01-18 IT IT2000MI000050A patent/IT1317729B1/it active
- 2000-10-17 DK DK00203602.8T patent/DK1118614T4/da active
- 2000-10-17 US US09/690,301 patent/US6458973B1/en not_active Expired - Fee Related
- 2000-10-17 ES ES00203602T patent/ES2178626T5/es not_active Expired - Lifetime
- 2000-10-17 DE DE60000226T patent/DE60000226T3/de not_active Expired - Lifetime
- 2000-10-17 EP EP00203602A patent/EP1118614B2/en not_active Expired - Lifetime
- 2000-10-17 AT AT00203602T patent/ATE219489T1/de not_active IP Right Cessation
- 2000-10-17 PT PT00203602T patent/PT1118614E/pt unknown
- 2000-12-07 JP JP2000372224A patent/JP4558182B2/ja not_active Expired - Lifetime
-
2001
- 2001-01-17 CN CNB018038484A patent/CN1184220C/zh not_active Expired - Lifetime
- 2001-01-17 CA CA2397497A patent/CA2397497C/en not_active Expired - Fee Related
- 2001-01-17 HU HU0204187A patent/HUP0204187A3/hu unknown
- 2001-01-17 RO ROA200200989A patent/RO121737B1/ro unknown
- 2001-01-17 AU AU26798/01A patent/AU779581B2/en not_active Revoked
- 2001-01-17 PL PL01356563A patent/PL356563A1/xx not_active IP Right Cessation
- 2001-01-17 BR BR0107853-4A patent/BR0107853A/pt not_active Application Discontinuation
- 2001-01-17 WO PCT/EP2001/000617 patent/WO2001053284A1/en not_active Ceased
- 2001-01-17 MX MXPA02007031A patent/MXPA02007031A/es active IP Right Grant
- 2001-01-17 EP EP01901181A patent/EP1187822A1/en not_active Withdrawn
-
2002
- 2002-01-25 HK HK02100631.3A patent/HK1042290B/en not_active IP Right Cessation
- 2002-07-09 ZA ZA200205475A patent/ZA200205475B/xx unknown
- 2002-07-16 BG BG106925A patent/BG65763B1/bg unknown
- 2002-08-23 US US10/227,038 patent/US6703516B2/en not_active Expired - Fee Related
-
2004
- 2004-03-08 US US10/796,336 patent/US20040171851A1/en not_active Abandoned
-
2007
- 2007-10-22 US US11/975,842 patent/US20080249319A1/en not_active Abandoned
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