JO2015B1 - Method of manufaefuring sertendole - Google Patents
Method of manufaefuring sertendoleInfo
- Publication number
- JO2015B1 JO2015B1 JO19982015A JOP19982015A JO2015B1 JO 2015 B1 JO2015 B1 JO 2015B1 JO 19982015 A JO19982015 A JO 19982015A JO P19982015 A JOP19982015 A JO P19982015A JO 2015 B1 JO2015 B1 JO 2015B1
- Authority
- JO
- Jordan
- Prior art keywords
- indole
- nuorophenyl
- glycine
- chloro
- reduction
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 3
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 abstract 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 abstract 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- GZKLJWGUPQBVJQ-UHFFFAOYSA-N sertindole Chemical compound C1=CC(F)=CC=C1N1C2=CC=C(Cl)C=C2C(C2CCN(CCN3C(NCC3)=O)CC2)=C1 GZKLJWGUPQBVJQ-UHFFFAOYSA-N 0.000 abstract 3
- 229960000652 sertindole Drugs 0.000 abstract 3
- VRJHQPZVIGNGMX-UHFFFAOYSA-N 4-piperidinone Chemical compound O=C1CCNCC1 VRJHQPZVIGNGMX-UHFFFAOYSA-N 0.000 abstract 2
- 239000004471 Glycine Substances 0.000 abstract 2
- JBOPQACSHPPKEP-UHFFFAOYSA-N Indoxyl acetate Chemical compound C1=CC=C2C(OC(=O)C)=CNC2=C1 JBOPQACSHPPKEP-UHFFFAOYSA-N 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- -1 alkalimetal salt Chemical class 0.000 abstract 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 abstract 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 abstract 2
- QVTQYSFCFOGITD-UHFFFAOYSA-N 2,5-dichlorobenzoic acid Chemical compound OC(=O)C1=CC(Cl)=CC=C1Cl QVTQYSFCFOGITD-UHFFFAOYSA-N 0.000 abstract 1
- ZFIMCCCQJDZLCT-UHFFFAOYSA-N 2-(4-fluoroanilino)acetic acid Chemical compound OC(=O)CNC1=CC=C(F)C=C1 ZFIMCCCQJDZLCT-UHFFFAOYSA-N 0.000 abstract 1
- WLQZFXJVVNNEJU-UHFFFAOYSA-N 5-chloro-1-(4-fluorophenyl)-3-(1,2,3,6-tetrahydropyridin-4-yl)indole Chemical compound C1=CC(F)=CC=C1N1C2=CC=C(Cl)C=C2C(C=2CCNCC=2)=C1 WLQZFXJVVNNEJU-UHFFFAOYSA-N 0.000 abstract 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 229910052802 copper Inorganic materials 0.000 abstract 1
- 239000010949 copper Substances 0.000 abstract 1
- 230000008030 elimination Effects 0.000 abstract 1
- 238000003379 elimination reaction Methods 0.000 abstract 1
- 238000011031 large-scale manufacturing process Methods 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
Landscapes
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
A process of manufacturing sertindole comprising preparation of N-(4-nuorophenyl)-N-(2-carboxy-4-chlorophenyl)glycine, by reacting an alkalimetal salt of 2,5-dichlorobenzoic acid with an alkalimetal salt of N-(4-fluorophenyl)glycine in an aqueous, alkaline environment in the presence of a copper catalyst; cyclisation of N-(4-fluorophenyI)-N-(2-carboxy-4-chlorophenyl)glycine to the corresponding 3-acetoxy-indole; reduction of the 3-acetoxy-indole and subsequent elimination of H2O thereby obtaining 5-chloro-l-(4-nuorophenyl)indole which is reacted with 4-piperidone in a mixture of an acetic acid and concentrated HCl; reduction of the resulting 5-chloro-l-(4-nuorophenyl)-3-(l,2,3,6-tetrahydropyridin-4-yl)indole and reaction of this compound with l-(2-chloroethyl)-2-imidazolidinon in order to obtain sertindole. Alternatively, 5- chloro-l-(4-fluorophenyl)-3-(l,2,3,6- tetrahydropyridin-4-yl)indole is first reacted with I-(2-chlorpethyl)-2-imidazolidinon followed by reduction thereby obtaining sertindole. This process uses reactants and solvents that are suitable and allowed in large scale manufacture. Furthermore good total yields are obtained
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK53697 | 1997-05-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JO2015B1 true JO2015B1 (en) | 1999-05-15 |
Family
ID=8094655
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JO19982015A JO2015B1 (en) | 1997-05-09 | 1998-05-07 | Method of manufaefuring sertendole |
Country Status (13)
| Country | Link |
|---|---|
| AR (1) | AR012661A1 (en) |
| CA (1) | CA2486883C (en) |
| CO (1) | CO4950521A1 (en) |
| DZ (1) | DZ2483A1 (en) |
| IL (1) | IL156180A0 (en) |
| IN (3) | IN187834B (en) |
| JO (1) | JO2015B1 (en) |
| MA (1) | MA25584A1 (en) |
| MY (1) | MY124162A (en) |
| PE (1) | PE73199A1 (en) |
| TN (1) | TNSN98063A1 (en) |
| TW (1) | TW487692B (en) |
| ZA (1) | ZA983726B (en) |
-
1998
- 1998-04-27 MY MYPI9801885 patent/MY124162A/en unknown
- 1998-05-01 IN IN948MA1998 patent/IN187834B/en unknown
- 1998-05-04 ZA ZA983726A patent/ZA983726B/en unknown
- 1998-05-04 CO CO98024289A patent/CO4950521A1/en unknown
- 1998-05-05 DZ DZ980094A patent/DZ2483A1/en active
- 1998-05-05 AR ARP980102090 patent/AR012661A1/en active IP Right Grant
- 1998-05-07 CA CA002486883A patent/CA2486883C/en not_active Expired - Fee Related
- 1998-05-07 IL IL15618098A patent/IL156180A0/en not_active IP Right Cessation
- 1998-05-07 JO JO19982015A patent/JO2015B1/en active
- 1998-05-08 TN TNTNSN98063A patent/TNSN98063A1/en unknown
- 1998-05-08 PE PE00035498A patent/PE73199A1/en not_active Application Discontinuation
- 1998-05-11 MA MA25070A patent/MA25584A1/en unknown
- 1998-07-02 TW TW87110712A patent/TW487692B/en not_active IP Right Cessation
-
2000
- 2000-09-08 IN IN777MA2000 patent/IN190902B/en unknown
- 2000-09-18 IN IN776MA2000 patent/IN192270B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL156180A0 (en) | 2003-12-23 |
| MY124162A (en) | 2006-06-30 |
| PE73199A1 (en) | 1999-08-09 |
| TNSN98063A1 (en) | 2005-03-15 |
| TW487692B (en) | 2002-05-21 |
| ZA983726B (en) | 1998-11-24 |
| CA2486883C (en) | 2009-04-28 |
| DZ2483A1 (en) | 2004-09-05 |
| CA2486883A1 (en) | 1998-11-19 |
| AR012661A1 (en) | 2000-11-08 |
| IN192270B (en) | 2004-03-27 |
| IN190902B (en) | 2003-08-30 |
| IN187834B (en) | 2002-06-29 |
| CO4950521A1 (en) | 2000-09-01 |
| MA25584A1 (en) | 2002-12-31 |
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