NO322146B1 - Fremgangsmate ved fremstilling av citalopram og intermediater for slik fremstilling - Google Patents
Fremgangsmate ved fremstilling av citalopram og intermediater for slik fremstilling Download PDFInfo
- Publication number
- NO322146B1 NO322146B1 NO20000008A NO20000008A NO322146B1 NO 322146 B1 NO322146 B1 NO 322146B1 NO 20000008 A NO20000008 A NO 20000008A NO 20000008 A NO20000008 A NO 20000008A NO 322146 B1 NO322146 B1 NO 322146B1
- Authority
- NO
- Norway
- Prior art keywords
- formula
- acid
- compound
- citalopram
- carried out
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 39
- 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 abstract description 23
- 229960001653 citalopram Drugs 0.000 title claims abstract description 23
- 238000002360 preparation method Methods 0.000 title abstract description 5
- 239000000543 intermediate Substances 0.000 title description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 28
- -1 1,3-dihydroisobenzofuran compound Chemical class 0.000 claims abstract description 19
- 238000006798 ring closing metathesis reaction Methods 0.000 claims abstract description 12
- 150000004795 grignard reagents Chemical class 0.000 claims abstract description 11
- 239000007818 Grignard reagent Substances 0.000 claims abstract description 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 3
- VMJNTFXCTXAXTC-UHFFFAOYSA-N 2,2-difluoro-1,3-benzodioxole-5-carbonitrile Chemical group C1=C(C#N)C=C2OC(F)(F)OC2=C1 VMJNTFXCTXAXTC-UHFFFAOYSA-N 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 23
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 21
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 14
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 8
- 150000001408 amides Chemical class 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
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- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 229910021529 ammonia Inorganic materials 0.000 claims description 4
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- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 239000002274 desiccant Substances 0.000 claims description 3
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- 238000007363 ring formation reaction Methods 0.000 claims description 3
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- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 2
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- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
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- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 2
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- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 13
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- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- UWBHMRBRLOJJAA-UHFFFAOYSA-N oxaluric acid Chemical compound NC(=O)NC(=O)C(O)=O UWBHMRBRLOJJAA-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- MFIGVHWSIDOXJO-UHFFFAOYSA-N propan-2-yl 1-oxo-3h-2-benzofuran-5-carboxylate Chemical compound CC(C)OC(=O)C1=CC=C2C(=O)OCC2=C1 MFIGVHWSIDOXJO-UHFFFAOYSA-N 0.000 description 1
- JZWFDVDETGFGFC-UHFFFAOYSA-N salacetamide Chemical group CC(=O)NC(=O)C1=CC=CC=C1O JZWFDVDETGFGFC-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- LSJNBGSOIVSBBR-UHFFFAOYSA-N thionyl fluoride Chemical compound FS(F)=O LSJNBGSOIVSBBR-UHFFFAOYSA-N 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
- A61K31/343—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide condensed with a carbocyclic ring, e.g. coumaran, bufuralol, befunolol, clobenfurol, amiodarone
-
- 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
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/38—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino groups bound to acyclic carbon atoms and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/70—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/84—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
- C07C237/30—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having the nitrogen atom of the carboxamide group bound to hydrogen atoms or to acyclic carbon atoms
-
- 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)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US5278897P | 1997-07-08 | 1997-07-08 | |
| DK82697 | 1997-07-08 | ||
| PCT/DK1998/000081 WO1998019513A2 (en) | 1997-07-08 | 1998-03-03 | Method for the preparation of citalopram |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20000008D0 NO20000008D0 (no) | 2000-01-03 |
| NO20000008L NO20000008L (no) | 2000-01-03 |
| NO322146B1 true NO322146B1 (no) | 2006-08-21 |
Family
ID=26064729
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20000008A NO322146B1 (no) | 1997-07-08 | 2000-01-03 | Fremgangsmate ved fremstilling av citalopram og intermediater for slik fremstilling |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US6229026B1 (is) |
| EP (1) | EP1015416B1 (is) |
| JP (1) | JP3526581B2 (is) |
| KR (1) | KR100357975B1 (is) |
| CN (1) | CN1206207C (is) |
| AT (1) | ATE205824T1 (is) |
| AU (1) | AU737610B2 (is) |
| BG (1) | BG64823B1 (is) |
| CA (1) | CA2291067C (is) |
| CZ (1) | CZ291440B6 (is) |
| DE (2) | DE69801764T2 (is) |
| DK (1) | DK1015416T3 (is) |
| EA (1) | EA001728B1 (is) |
| ES (1) | ES2148120T3 (is) |
| HU (1) | HU228744B1 (is) |
| IL (2) | IL133511A (is) |
| IS (1) | IS2023B (is) |
| NO (1) | NO322146B1 (is) |
| NZ (1) | NZ501737A (is) |
| PT (1) | PT1015416E (is) |
| SK (1) | SK283309B6 (is) |
| TR (1) | TR200000066T2 (is) |
| WO (1) | WO1998019513A2 (is) |
Families Citing this family (52)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA62985C2 (en) | 1997-11-10 | 2004-01-15 | Lunnbeck As H | A method for the preparation of citalopram |
| PL199423B1 (pl) * | 1998-10-20 | 2008-09-30 | Lundbeck & Co As H | Sposób wytwarzania citalopramu |
| TR200101796T2 (tr) | 1998-12-23 | 2001-11-21 | H. Lundbeck A/S | 5-Siyanofitalitin preparasyonuna yönelik metot |
| AR022329A1 (es) | 1999-01-29 | 2002-09-04 | Lundbeck & Co As H | Metodo para la preparacion de 5-cianoftalida |
| ATE237604T1 (de) * | 1999-04-14 | 2003-05-15 | Lundbeck & Co As H | Verfahren zur herstellung von citalopram |
| US6245782B1 (en) | 1999-05-17 | 2001-06-12 | Heartdrug Research L.L.C. | Methods of inhibiting platelet activation with selective serotonin reuptake inhibitors |
| 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 |
| ITMI991486A1 (it) * | 1999-07-06 | 2001-01-06 | Vis Farmaceutici S P A | Processo per la sintesi di citalopram |
| HUP0200169A3 (en) * | 1999-10-25 | 2002-11-28 | Lundbeck & Co As H | Method for the preparation of citalopram |
| GB2360281B (en) | 1999-10-25 | 2002-01-16 | Lundbeck & Co As H | 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. |
| WO2001047909A1 (en) | 1999-12-28 | 2001-07-05 | H. Lundbeck A/S | Method for the preparation of citalopram |
| PL198803B1 (pl) * | 1999-12-30 | 2008-07-31 | Lundbeck & Co As H | Sposób wytwarzania 5-cyjano-3H-izobenzofuran-1-onu |
| 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. |
| NL1017415C1 (nl) | 2000-02-24 | 2001-05-18 | Lundbeck & Co As H | Werkwijze voor de bereiding van Citalopram. |
| 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 |
| GB2357762B (en) * | 2000-03-13 | 2002-01-30 | Lundbeck & Co As H | Crystalline base of citalopram |
| IES20010206A2 (en) | 2000-03-13 | 2002-03-06 | Lundbeck & Co As H | Method for the preparation of citalopram |
| BR0109176A (pt) | 2000-03-13 | 2003-04-22 | Lundbeck & Co As H | Método para preparação de citalopram e composto da fórmula |
| CA2402553A1 (en) | 2000-03-13 | 2001-09-20 | H. Lundbeck A/S | Stepwise alkylation of 5-substituted 1-(4-fluorophenyl)-1,3-dihydroisobenzofurans |
| IL151488A0 (en) | 2000-03-14 | 2003-04-10 | Lundbeck & Co As H | Method for the preparation of citalopram |
| EP1274699A1 (en) * | 2000-03-16 | 2003-01-15 | 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 |
| CA2354880C (en) * | 2000-08-18 | 2003-06-03 | H. Lundbeck A/S | Method for the preparation of citalopram |
| IT1319686B1 (it) * | 2000-12-12 | 2003-10-23 | C D Farmasint S R L | Procedimento di preparazione di citalopram. |
| IL147226A (en) * | 2000-12-22 | 2006-04-10 | Lundbeck & Co As H | Process for the preparation of pure cithalopram |
| PT1181272E (pt) * | 2000-12-28 | 2003-01-31 | Lundbeck & Co As H | Processo para a preparacao de citalopram puro |
| DE10112828C1 (de) * | 2000-12-28 | 2002-11-21 | Lundbeck & Co As H | Verfahren zur Herstellung von Citalopram |
| CA2435925A1 (en) | 2001-01-30 | 2002-08-08 | Orion Corporation Fermion | Process for the preparation of 1-(3-dimethylaminopropyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile |
| BG65271B1 (bg) * | 2001-06-18 | 2007-11-30 | H. Lundbeck A/S | Метод за получаване на циталопрам |
| IN192057B (is) * | 2001-07-19 | 2004-02-14 | Ranbaxy Lab Ltd | |
| DE60217932T2 (de) | 2001-07-31 | 2007-08-30 | H. Lundbeck A/S, Valby | Kristalline Zusammensetzung enthaltend Escitalopram |
| DE60108105T2 (de) * | 2001-08-02 | 2005-12-08 | Infosint Sa | Verfahren zur Herstellung von 5-substituierten Isobenzofuranen |
| GR1004635B (el) * | 2001-08-14 | 2004-07-14 | H@Αlundbeckαa@Sαα | Μεθοδοσαπαρασκευησατησασιταλοπραμης@αα |
| EP1288211A1 (en) * | 2001-08-28 | 2003-03-05 | Sekhsaria Chemicals Ltd. | Improved process for the manufacture of citalopram hydrobromide from 5-bromophthalide |
| AU2003222435A1 (en) | 2002-01-07 | 2003-07-24 | Sun Pharmaceutical Industries Limited | Process for the preparation of 1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)- 1,3-dihydro-5-isobenzofuran carbonitrile |
| GB2387596B (en) * | 2002-02-27 | 2004-02-11 | Matrix Lab Ltd | Process |
| HU0200980D0 (is) * | 2002-03-14 | 2002-05-29 | Gabor S Pal Dr | |
| BG65515B1 (bg) * | 2002-07-26 | 2008-10-31 | H. Lundbeck A/S | Метод за получаване на 5-цианофталид |
| AU2002330730A1 (en) * | 2002-08-14 | 2004-03-03 | Natco Pharma Limited | Process for the preparation of high purity citalopram and its pharmaceutically acceptable salts |
| US6812355B2 (en) | 2002-10-22 | 2004-11-02 | Sekhsaria Chemicals Limited | Process for the manufacture of citalopram hydrobromide from 5-bromophthalide |
| ITMI20030479A1 (it) * | 2003-03-13 | 2004-09-14 | Adorkem Technology S P A | Procedimento per la preparazione di un ciano-isobenzofurano. |
| US7687645B2 (en) | 2003-03-21 | 2010-03-30 | H. Lundbeck A/S | Intermediates for the preparation of citalopram and escitalopram |
| US7019153B2 (en) | 2003-06-10 | 2006-03-28 | Sun Pharmaceutical Industries Limited | Process for hydrogenolysis of [1-(3-dimethylamino)propyl)]-1-(4-fluorophenyl)-1,3-dihydro-5-halo-isobenzofuran acetamido-3-substituted-3-cephem-4-carboxylic acid |
| ATE293106T1 (de) * | 2003-10-28 | 2005-04-15 | Adorkem Technology Spa | Verfahren zur herstellung von citalopram |
| KR101166280B1 (ko) | 2004-08-23 | 2013-11-27 | 썬 파마 글로벌 에프제트이 | 시탈로프램 및 에난티오머의 제조 방법 |
| US7834201B2 (en) | 2005-06-22 | 2010-11-16 | H. Lundbeck A/S | Crystalline base of escitalopram and orodispersible tablets comprising escitalopram base |
| TWI347942B (en) | 2005-06-22 | 2011-09-01 | Lundbeck & Co As H | Crystalline base of escitalopram and orodispersible tablets comprising escitalopram base |
| US9339500B2 (en) * | 2008-03-04 | 2016-05-17 | Intra-Cellular Therapies, Inc. | Methods of treating vasomotor symptoms |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1143702A (is) | 1965-03-18 | |||
| GB1526331A (en) * | 1976-01-14 | 1978-09-27 | Kefalas As | Phthalanes |
| GB8419963D0 (en) * | 1984-08-06 | 1984-09-12 | Lundbeck & Co As H | Intermediate compound and method |
| DK213290D0 (da) * | 1990-09-06 | 1990-09-06 | Lundbeck & Co As H | Treatment of cerebrovascular disorders |
| NZ243065A (en) | 1991-06-13 | 1995-07-26 | Lundbeck & Co As H | Piperidine derivatives and pharmaceutical compositions |
-
1998
- 1998-03-03 JP JP52097198A patent/JP3526581B2/ja not_active Expired - Fee Related
- 1998-03-03 AT AT98905125T patent/ATE205824T1/de active
- 1998-03-03 KR KR1020007000063A patent/KR100357975B1/ko not_active IP Right Cessation
- 1998-03-03 DE DE69801764T patent/DE69801764T2/de not_active Expired - Lifetime
- 1998-03-03 EA EA200000102A patent/EA001728B1/ru not_active IP Right Cessation
- 1998-03-03 IL IL13351198A patent/IL133511A/en not_active IP Right Cessation
- 1998-03-03 CN CNB2003101164072A patent/CN1206207C/zh not_active Expired - Fee Related
- 1998-03-03 PT PT98905125T patent/PT1015416E/pt unknown
- 1998-03-03 HU HU0003177A patent/HU228744B1/hu not_active IP Right Cessation
- 1998-03-03 EP EP98905125A patent/EP1015416B1/en not_active Expired - Lifetime
- 1998-03-03 DE DE1015416T patent/DE1015416T1/de active Pending
- 1998-03-03 CA CA002291067A patent/CA2291067C/en not_active Expired - Fee Related
- 1998-03-03 TR TR2000/00066T patent/TR200000066T2/xx unknown
- 1998-03-03 DK DK98905125T patent/DK1015416T3/da active
- 1998-03-03 SK SK3-2000A patent/SK283309B6/sk not_active IP Right Cessation
- 1998-03-03 CZ CZ200062A patent/CZ291440B6/cs not_active IP Right Cessation
- 1998-03-03 WO PCT/DK1998/000081 patent/WO1998019513A2/en active IP Right Grant
- 1998-03-03 AU AU66098/98A patent/AU737610B2/en not_active Ceased
- 1998-03-03 ES ES98905125T patent/ES2148120T3/es not_active Expired - Lifetime
- 1998-03-03 NZ NZ501737A patent/NZ501737A/en unknown
-
1999
- 1999-12-14 IS IS5300A patent/IS2023B/is unknown
-
2000
- 2000-01-03 NO NO20000008A patent/NO322146B1/no not_active IP Right Cessation
- 2000-01-07 US US09/479,832 patent/US6229026B1/en not_active Expired - Lifetime
- 2000-01-31 BG BG104116A patent/BG64823B1/bg unknown
-
2002
- 2002-11-27 IL IL153125A patent/IL153125A/en not_active IP Right Cessation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |