DE1042310T1 - Verfahren zur herstellung von citaloprame - Google Patents
Verfahren zur herstellung von citaloprameInfo
- Publication number
- DE1042310T1 DE1042310T1 DE1042310T DE97945799T DE1042310T1 DE 1042310 T1 DE1042310 T1 DE 1042310T1 DE 1042310 T DE1042310 T DE 1042310T DE 97945799 T DE97945799 T DE 97945799T DE 1042310 T1 DE1042310 T1 DE 1042310T1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- compound
- group
- process according
- ring closure
- 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.)
- Pending
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract 15
- 150000001875 compounds Chemical class 0.000 claims abstract 12
- 239000007818 Grignard reagent Substances 0.000 claims abstract 7
- 150000004795 grignard reagents Chemical class 0.000 claims abstract 7
- 238000006798 ring closing metathesis reaction Methods 0.000 claims abstract 6
- 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 claims abstract 5
- -1 1,3-dihydroisobenzofuran compound Chemical class 0.000 claims abstract 5
- 238000006243 chemical reaction Methods 0.000 claims abstract 5
- 229960001653 citalopram Drugs 0.000 claims abstract 5
- 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 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 238000006193 diazotization reaction Methods 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 230000001430 anti-depressive effect Effects 0.000 claims 1
- 239000000935 antidepressant agent Substances 0.000 claims 1
- 229940005513 antidepressants Drugs 0.000 claims 1
- 150000003842 bromide salts Chemical class 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 150000003841 chloride salts Chemical class 0.000 claims 1
- 230000032050 esterification Effects 0.000 claims 1
- 238000005886 esterification reaction Methods 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims 1
- 150000004694 iodide salts Chemical class 0.000 claims 1
- 229910052749 magnesium Inorganic materials 0.000 claims 1
- 239000011777 magnesium Substances 0.000 claims 1
- OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 claims 1
- 229910001623 magnesium bromide Inorganic materials 0.000 claims 1
- 229910001629 magnesium chloride Inorganic materials 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 238000007363 ring formation reaction Methods 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims 1
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/68—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings and hydroxy groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
-
- 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
- C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
- C07C225/22—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/30—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by doubly-bound oxygen atoms
- C07C233/33—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by doubly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
- C07C233/42—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
- C07C233/43—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of a saturated carbon skeleton
-
- 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
-
- 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)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (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)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Claims (17)
1. Ein Verfahren zur Herstellung von Citalopram umfassend die Schritte
a) eine Verbindung der Formel IV
R H I &ogr; Formel IV
wobei R1 H oder eine Ci-6-Alkylcarbonylgruppe
ist, mit einem Grignardreagenz aus 4-Halogenfluorphenyl
zur Reaktion bringen;
b) die resultierende Verbindung der Formel V H
Formel V
wobei R1 wie oben definiert ist, mit einem Grignardreagenz aus 3-Halogen-N,N-dimethylpropylamin zur
Reaktion bringen;
c) einen Ringschluss des resultierenden Verbindung der Formel VI
DrJH EU/CH 1.3300
30.06.1998
und
VII
CH2OH
CH3 .OH &igr;
N-CH
- 3 Formel VI
wobei R1 wie oben definiert ist, zu bewirken,
d) die resultierende Verbindung der Formel H
Formel VII
wobei R1 wie oben definiert ist, in das entsprechende 5-Cyanoderivat, d.h. Citalopram, umzuwandeln,
welches als die Base oder ein pharmazeutisch annehmbares Salz desselben isoliert wird.
2. Das Verfahren nach Anspruch 1, wobei R1 H
ist.
3. Das Verfahren nach Anspruch 1, wobei R1 eine Ci-6-Alkylcarbonylgruppe ist.
4. Das Verfahren nach Anspruch 3, wobei Ci-6-Alkyl
eine Methyl-, Ethyl-, Propyl- oder Butylgruppe ist
5. Das Verfahren nach einem der Ansprüche 1 bis 4, wobei das verwendete Grignardreagenz Magnesiumhalogenide,
vorzugsweise die Chloride, Bromide oder Iodide, sind.
DrJH 30.06.1998
EU/CH 1.3300
042310 &tgr;&igr;
6. Das Verfahren nach Anspruch 5, wobei die Grignardreagenzien, welche im Schritt a) verwendet werden,
das Magnesiumbromid ist.
7. Das Verfahren nach Anspruch 5, wobei die Grignardreagenzien, welche im Schritt b) verwendet werden,
das Magnesiumchlorid ist.
8. Das Verfahren nach einem der Ansprüche 1 bis 7, wobei der Ringschluss der Verbindung gemäss der
Formel VI mittels saurem Ringschluss, durchgeführt mit einer anorganischen Säure, wie etwa Schwefelsäure oder
Phosphorsäure, oder mit einer organischen Säure, wie etwa Methylsulfonsäure, p-Toluolsulfonsäure oder Trifluoressigsäure,
bewirkt wird.
9. Das Verfahren nach Anspruch 3, wobei der Ringschluss der Verbindung gemäss der Formel VI mittels
basischem Ringschluss über einen labilen Ester, vorzugsweise mit gleichzeitiger Veresterung und Zugabe einer
Base, durchgeführt wird.
10. Das Verfahren nach Anspruch 9, wobei der labile Ester der Methansulfonyl-, p-Toluolsulfonyl-, 10-Camphersulfonyl-,
Trifluoracetyl- oder Trifluormethansulfonylester ist, und die Base ist Triethylamin, Dimethylanilin
oder Pyridin.
11. Das Verfahren nach Anspruch 2, wobei die
Umwandlung der Gruppe R^NH- in eine Cyanogruppe mit einer
Diazotierung gefolgt von einer Reaktion mit CN" durchgeführt wird.
12. Das Verfahren nach Anspruch 3, wobei die Umwandlung der Gruppe R^NH- in eine Cyanogruppe mittels
Hydrolyse der Ci-6-Alkylcarbonylaminogruppe, R^NH-, in
die entsprechende Aminogruppe, wobei R1 H ist, gefolgt
DrJH EU/CH 1.3300
30.06.1998
von einer Diazotierung und einer Reaktion mit CN , durchgeführt wird.
13. Ein Verfahren nach einem der Ansprüche 1 bis 12, dadurch gekennzeichnet, dass bevor sie im Ringschluss-Reaktionsschritt
c) verwendet wird, wird die Verbindung der Formel VI in die optisch aktiven Enantiomere
getrennt, wobei das (S)-Enantiomer erhalten wird.
20 ist 25
ist.
14. Eine Verbindung der Formel V
Formel V
wobei R1 H oder eine Ci-6-Alkylcarbonylgruppe
15. Eine Verbindung der Formel VI CH2OH
H
N
N
R1
Formel VI
wobei R1 H oder eine Ci-6-Alkylcarbonylgruppe
16. Eine Verbindung der Formel VII
Dr.JH 30.06.1998
EU/CH 1.3300
io ist.
Formel VII
wobei R1 H oder eine Ci-6-Alkylcarbonylgruppe
17. Eine antidepressiv wirkende pharmazeutische Zusammensetzung umfassend Citalopram, hergestellt
nach dem Verfahren gemäss einem der Ansprüche 1 bis 13.
Dr.JH 30.06.1998
EU/CH 1.3300
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN97182416A CN1286687A (zh) | 1997-11-11 | 1997-11-11 | 制备西酞普兰的方法 |
| PCT/DK1997/000513 WO1998019512A2 (en) | 1997-11-11 | 1997-11-11 | Method for the preparation of citalopram |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1042310T1 true DE1042310T1 (de) | 2001-04-19 |
Family
ID=37709785
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1042310T Pending DE1042310T1 (de) | 1997-11-11 | 1997-11-11 | Verfahren zur herstellung von citaloprame |
| DE69714480T Expired - Fee Related DE69714480T2 (de) | 1997-11-11 | 1997-11-11 | Verfahren zur Herstellung von Citalopram |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69714480T Expired - Fee Related DE69714480T2 (de) | 1997-11-11 | 1997-11-11 | Verfahren zur Herstellung von Citalopram |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US6258842B1 (de) |
| EP (1) | EP1042310B1 (de) |
| JP (1) | JP3813820B2 (de) |
| CN (1) | CN1286687A (de) |
| AT (1) | ATE221522T1 (de) |
| AU (1) | AU738359B2 (de) |
| BR (1) | BR9714925A (de) |
| CA (1) | CA2291072C (de) |
| CZ (1) | CZ292911B6 (de) |
| DE (2) | DE1042310T1 (de) |
| DK (1) | DK1042310T3 (de) |
| EA (1) | EA002770B1 (de) |
| ES (1) | ES2149734T3 (de) |
| HU (1) | HUP0002953A3 (de) |
| IS (1) | IS2009B (de) |
| SK (1) | SK283907B6 (de) |
| TR (1) | TR200001341T2 (de) |
| UA (1) | UA62984C2 (de) |
| WO (1) | WO1998019512A2 (de) |
| ZA (1) | ZA9810058B (de) |
Families Citing this family (57)
| 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 |
| PT1140886E (pt) | 1998-12-23 | 2003-08-29 | Lundbeck & Co As H | Metodo para a preparacao de 5- cianoftalida |
| AR022329A1 (es) | 1999-01-29 | 2002-09-04 | Lundbeck & Co As H | Metodo para la preparacion de 5-cianoftalida |
| DE69907037T3 (de) | 1999-04-14 | 2010-02-18 | H. Lundbeck A/S | 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 |
| AR021155A1 (es) * | 1999-07-08 | 2002-06-12 | Lundbeck & Co As H | Tratamiento de desordenes neuroticos |
| CH692421A5 (de) | 1999-10-25 | 2002-06-14 | Lundbeck & Co As H | Verfahren zur Herstellung von Citalopram. |
| DK1228056T3 (da) * | 1999-10-25 | 2005-01-24 | Lundbeck & Co As H | Fremgangsmåde til fremstilling af citalopram |
| AR026063A1 (es) | 1999-11-01 | 2002-12-26 | Lundbeck & Co As H | Metodo para la preparacion de 5-carboxiftalida. |
| IL150335A0 (en) | 1999-12-28 | 2002-12-01 | Lundbeck & Co As H | Method for the preparation of citalopram |
| CZ20022627A3 (cs) * | 1999-12-30 | 2002-10-16 | H. Lundbeck A/S | Způsob výroby citalopramu |
| DK1254129T3 (da) | 2000-01-14 | 2004-03-29 | Lundbeck & Co As H | Fremgangsmåde til fremstilling af 5-cyanophthalid |
| FR2805812A1 (fr) | 2000-02-24 | 2001-09-07 | Lundbeck & Co As H | Procede de preparation du 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 |
| IES20010206A2 (en) | 2000-03-13 | 2002-03-06 | Lundbeck & Co As H | Method for the preparation of citalopram |
| IL151566A0 (en) | 2000-03-13 | 2003-04-10 | Lundbeck & Co As H | Stepwise alkylation of 5-substituted 1-(4-fluorophenyl)-1,3-dihydroisobenzofurans |
| GB2357762B (en) * | 2000-03-13 | 2002-01-30 | Lundbeck & Co As H | Crystalline base of citalopram |
| HUP0300274A2 (hu) | 2000-03-13 | 2003-06-28 | H. Lundbeck A/S | Eljárás citalopram előállítására |
| SK14512002A3 (sk) | 2000-03-14 | 2003-03-04 | H. Lundbeck A/S | Spôsob výroby citalopramu, medziprodukt a citalopram výrobený týmto spôsobom |
| BR0109180A (pt) * | 2000-03-16 | 2003-05-27 | Lundbeck & Co As H | Método para a preparação de 5-ciano-1-(4-fluorofenil) -1,3- diidroisobenzofuranos e composição farmacêutica de antidepressivo |
| 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 |
| US6879110B2 (en) * | 2000-07-27 | 2005-04-12 | Semiconductor Energy Laboratory Co., Ltd. | Method of driving display device |
| FI20011622L (fi) * | 2000-08-18 | 2002-02-19 | Lundbeck & Co As H | Menetelmä sitalopraamin valmistamiseksi |
| IT1319686B1 (it) * | 2000-12-12 | 2003-10-23 | C D Farmasint S R L | Procedimento di preparazione di citalopram. |
| TR200201166T1 (tr) * | 2000-12-22 | 2002-10-21 | H.Lundbecks A/S | Saf sitalopram hazırlanması için yöntem |
| EP1181272B1 (de) | 2000-12-28 | 2002-08-28 | H. Lundbeck A/S | Verfahren zur herstellung von reinem citalopram |
| DE10112828C1 (de) * | 2000-12-28 | 2002-11-21 | Lundbeck & Co As H | Verfahren zur Herstellung von Citalopram |
| EP1355897A1 (de) | 2001-01-30 | 2003-10-29 | Orion Corporation Fermion | Verfahren zur herstellung von 1-(3-dimethylaminopropyl)-1-(4-fluorphenyl)-1,3-dihydrobenzofuran-5-carbonitrile |
| HUP0400054A3 (en) * | 2001-05-01 | 2007-03-28 | Lundbeck & Co As H | The use of enantiomeric pure escitalopram |
| BG65271B1 (bg) * | 2001-06-18 | 2007-11-30 | H. Lundbeck A/S | Метод за получаване на циталопрам |
| AU2002355624B2 (en) * | 2001-07-31 | 2006-02-02 | H. Lundbeck A/S | Crystalline composition containing escitalopram |
| IS7239A (is) * | 2001-12-14 | 2004-04-29 | H. Lundbeck A/S | Aðferð til framleiðslu á essítalóprami |
| WO2003057132A2 (en) | 2002-01-07 | 2003-07-17 | Sun Pharmaceutical Industries Limited | Process for the preparation of 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)- 1,3-dihydro-5-isobenzofuran carbonitrile |
| HU0200980D0 (de) * | 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 |
| AR040970A1 (es) | 2002-08-12 | 2005-04-27 | Lundbeck & Co As H | Metodo para la separacion de intermediarios que pueden ser utilizados para la preparacion de escitalopram |
| 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. |
| US6781003B1 (en) * | 2003-06-09 | 2004-08-24 | Aurobindo Pharma Ltd. | Preparation of pure citalopram |
| 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 |
| DE60300502T2 (de) * | 2003-10-28 | 2006-02-23 | Adorkem Technology S.P.A., Costa Volpino | Verfahren zur Herstellung von Citalopram |
| 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 |
| EP1797060A2 (de) | 2004-08-23 | 2007-06-20 | Sun Pharmaceutical Industries Limited | Verfahren zur herstellung von citalopram und enantiomeren |
| WO2006103550A1 (en) * | 2005-03-31 | 2006-10-05 | Ranbaxy Laboratories Limited | Processes for the preparation of citalopram and its intermediate 5-aminophthalide |
| US7834201B2 (en) | 2005-06-22 | 2010-11-16 | H. Lundbeck A/S | Crystalline base of escitalopram and orodispersible tablets comprising escitalopram base |
| TWI358407B (en) | 2005-06-22 | 2012-02-21 | Lundbeck & Co As H | Crystalline base of escitalopram and orodispersibl |
| CN100391952C (zh) * | 2005-07-12 | 2008-06-04 | 广东西陇化工有限公司 | 西酞普兰盐的制备方法 |
| US9339500B2 (en) * | 2008-03-04 | 2016-05-17 | Intra-Cellular Therapies, Inc. | Methods of treating vasomotor symptoms |
| CN105801333B (zh) * | 2016-04-29 | 2017-12-22 | 江苏佳麦化工有限公司 | 一种晕苯的制备方法 |
| CN105801329B (zh) * | 2016-04-29 | 2017-11-28 | 阜阳欣奕华材料科技有限公司 | 一种晕苯的制备方法 |
| CN105801328B (zh) * | 2016-04-29 | 2017-12-08 | 浙江瑞灿科技有限公司 | 一种晕苯的制备方法 |
| CN106748627A (zh) * | 2016-11-14 | 2017-05-31 | 苏州市罗森助剂有限公司 | 一种一锅法制备3,5‑二甲基溴苯的方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1143702A (de) | 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 |
| NZ243065A (en) | 1991-06-13 | 1995-07-26 | Lundbeck & Co As H | Piperidine derivatives and pharmaceutical compositions |
| UA62985C2 (en) | 1997-11-10 | 2004-01-15 | Lunnbeck As H | A method for the preparation of citalopram |
-
1997
- 1997-11-11 DE DE1042310T patent/DE1042310T1/de active Pending
- 1997-11-11 WO PCT/DK1997/000513 patent/WO1998019512A2/en active IP Right Grant
- 1997-11-11 SK SK682-2000A patent/SK283907B6/sk unknown
- 1997-11-11 AT AT97945799T patent/ATE221522T1/de not_active IP Right Cessation
- 1997-11-11 DE DE69714480T patent/DE69714480T2/de not_active Expired - Fee Related
- 1997-11-11 CZ CZ20001736A patent/CZ292911B6/cs not_active IP Right Cessation
- 1997-11-11 UA UA2000052827A patent/UA62984C2/uk unknown
- 1997-11-11 AU AU51168/98A patent/AU738359B2/en not_active Ceased
- 1997-11-11 CA CA002291072A patent/CA2291072C/en not_active Expired - Fee Related
- 1997-11-11 CN CN97182416A patent/CN1286687A/zh active Pending
- 1997-11-11 JP JP2000583315A patent/JP3813820B2/ja not_active Expired - Fee Related
- 1997-11-11 TR TR2000/01341T patent/TR200001341T2/xx unknown
- 1997-11-11 EA EA200000511A patent/EA002770B1/ru not_active IP Right Cessation
- 1997-11-11 BR BR9714925-0A patent/BR9714925A/pt not_active Application Discontinuation
- 1997-11-11 HU HU0002953A patent/HUP0002953A3/hu unknown
- 1997-11-11 DK DK97945799T patent/DK1042310T3/da active
- 1997-11-11 EP EP97945799A patent/EP1042310B1/de not_active Expired - Lifetime
- 1997-11-11 ES ES97945799T patent/ES2149734T3/es not_active Expired - Lifetime
-
1998
- 1998-11-03 ZA ZA9810058A patent/ZA9810058B/xx unknown
-
2000
- 2000-04-18 IS IS5461A patent/IS2009B/is unknown
- 2000-04-28 US US09/564,365 patent/US6258842B1/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| DE69714480D1 (de) | 2002-09-05 |
| DE69714480T2 (de) | 2003-03-06 |
| EA002770B1 (ru) | 2002-08-29 |
| AU5116898A (en) | 1998-05-29 |
| ES2149734T3 (es) | 2003-02-16 |
| CZ292911B6 (cs) | 2004-01-14 |
| CA2291072A1 (en) | 1998-05-14 |
| CA2291072C (en) | 2002-08-20 |
| JP3813820B2 (ja) | 2006-08-23 |
| SK283907B6 (sk) | 2004-04-06 |
| TR200001341T2 (tr) | 2000-11-21 |
| JP2002530295A (ja) | 2002-09-17 |
| ATE221522T1 (de) | 2002-08-15 |
| WO1998019512A3 (en) | 1998-08-13 |
| IS2009B (is) | 2005-05-13 |
| DK1042310T3 (da) | 2002-12-02 |
| SK6822000A3 (en) | 2000-10-09 |
| WO1998019512A2 (en) | 1998-05-14 |
| UA62984C2 (en) | 2004-01-15 |
| US6258842B1 (en) | 2001-07-10 |
| CZ20001736A3 (cs) | 2000-10-11 |
| EP1042310A2 (de) | 2000-10-11 |
| ES2149734T1 (es) | 2000-11-16 |
| CN1286687A (zh) | 2001-03-07 |
| EP1042310B1 (de) | 2002-07-31 |
| ZA9810058B (en) | 1999-05-05 |
| HUP0002953A2 (hu) | 2001-04-28 |
| IS5461A (is) | 2000-04-18 |
| AU738359B2 (en) | 2001-09-13 |
| HUP0002953A3 (en) | 2002-12-28 |
| BR9714925A (pt) | 2003-07-22 |
| EA200000511A1 (ru) | 2000-10-30 |
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