EA200100696A1 - Способ получения 5-цианофталида - Google Patents
Способ получения 5-цианофталидаInfo
- Publication number
- EA200100696A1 EA200100696A1 EA200100696A EA200100696A EA200100696A1 EA 200100696 A1 EA200100696 A1 EA 200100696A1 EA 200100696 A EA200100696 A EA 200100696A EA 200100696 A EA200100696 A EA 200100696A EA 200100696 A1 EA200100696 A1 EA 200100696A1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- cyanophthalide
- amide
- formula
- carboxyphthalide
- obtaining
- Prior art date
Links
- XEEGWTLAFIZLSF-UHFFFAOYSA-N 1-oxo-3h-2-benzofuran-5-carbonitrile Chemical compound N#CC1=CC=C2C(=O)OCC2=C1 XEEGWTLAFIZLSF-UHFFFAOYSA-N 0.000 title abstract 4
- 238000000034 method Methods 0.000 title abstract 2
- 150000001408 amides Chemical class 0.000 abstract 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- 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 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- 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 abstract 1
- 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 abstract 1
- 150000003973 alkyl amines Chemical class 0.000 abstract 1
- 230000009435 amidation Effects 0.000 abstract 1
- 238000007112 amidation reaction Methods 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 239000000935 antidepressant agent Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 229960001653 citalopram Drugs 0.000 abstract 1
- 239000012024 dehydrating agents Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- -1 phenyl ester Chemical class 0.000 abstract 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
- Furan Compounds (AREA)
Abstract
Способ получения 5-цианофталида, в котором 5-карбоксифталид преобразуют в соответствующий амид формулы (IV), где R представляет собой водород или Cалкил, после чего указанный амид подвергают реакции с дегидратирующим агентом с получением 5-цианофталида. Преобразование 5-карбоксифталида в соответствующий амид формулы (IV) может быть осуществлено через соответствующий Cалкиловый или фениловый эфир или хлорангидрид, который преобразуют в амид формулы (IV) путем амидирования аммиаком или Cалкиламином. В соответствии с этим, 5-цианофталид, который является важным промежуточным соединением для получения антидепрессантного лекарственного средства циталопрама, получают с высоким выходом эффективным и экономически выгодным способом.Международная заявка была опубликована вместе с отчетом о международном поиске.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DKPA199801718 | 1998-12-23 | ||
PCT/DK1999/000728 WO2000039112A1 (en) | 1998-12-23 | 1999-12-22 | Method for the preparation of 5-cyanophthalide |
Publications (2)
Publication Number | Publication Date |
---|---|
EA200100696A1 true EA200100696A1 (ru) | 2001-12-24 |
EA003057B1 EA003057B1 (ru) | 2002-12-26 |
Family
ID=8107494
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EA200100696A EA003057B1 (ru) | 1998-12-23 | 1999-12-22 | Способ получения 5-цианофталида |
Country Status (31)
Country | Link |
---|---|
US (1) | US6392060B2 (ru) |
EP (1) | EP1140886B1 (ru) |
JP (1) | JP2002533450A (ru) |
KR (1) | KR100454008B1 (ru) |
CN (1) | CN1149208C (ru) |
AR (1) | AR019791A1 (ru) |
AT (1) | ATE236145T1 (ru) |
AU (1) | AU764161B2 (ru) |
BG (1) | BG64986B1 (ru) |
BR (1) | BR9916955A (ru) |
CA (1) | CA2356188C (ru) |
CZ (1) | CZ300408B6 (ru) |
DE (1) | DE69906580T2 (ru) |
DK (1) | DK1140886T3 (ru) |
EA (1) | EA003057B1 (ru) |
ES (1) | ES2195644T3 (ru) |
HK (1) | HK1043130B (ru) |
HU (1) | HUP0104856A3 (ru) |
IL (1) | IL143422A0 (ru) |
IS (1) | IS2261B (ru) |
IT (1) | IT1315269B1 (ru) |
NO (1) | NO326516B1 (ru) |
NZ (1) | NZ512073A (ru) |
PL (1) | PL203275B1 (ru) |
PT (1) | PT1140886E (ru) |
SI (1) | SI1140886T1 (ru) |
SK (1) | SK285530B6 (ru) |
TR (1) | TR200101796T2 (ru) |
UA (1) | UA70979C2 (ru) |
WO (1) | WO2000039112A1 (ru) |
ZA (1) | ZA200104262B (ru) |
Families Citing this family (27)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE69904853T2 (de) | 1998-10-20 | 2003-09-04 | Lundbeck As Valby H | Verfahren zur herstellung von citalopram |
IL143422A0 (en) | 1998-12-23 | 2002-04-21 | Lundbeck & Co As H | Method for the preparation of 5-cyanophthalide |
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 |
ITMI991579A1 (it) | 1999-06-25 | 2001-01-15 | Lundbeck & Co As H | Metodo per la preparazione di citalopram |
ITMI991581A1 (it) * | 1999-06-25 | 2001-01-15 | Lundbeck & Co As H | Metodo per la preparazione di citalopram |
WO2000012044A2 (en) | 1999-10-25 | 2000-03-09 | H. Lundbeck A/S | Method for the preparation of citalopram |
ATE355268T1 (de) | 1999-10-25 | 2006-03-15 | Lundbeck & Co As H | Verfahren zur herstellung von citalopram |
AR026063A1 (es) | 1999-11-01 | 2002-12-26 | Lundbeck & Co As H | Metodo para la preparacion de 5-carboxiftalida. |
CA2395404A1 (en) | 1999-12-28 | 2001-07-05 | H. Lundbeck A/S | Method for the preparation of citalopram |
IL150367A0 (en) | 1999-12-30 | 2002-12-01 | Lundbeck & Co As H | Method for the preparation of citalopram |
IL150561A0 (en) | 2000-01-14 | 2003-02-12 | Lundbeck & Co As H | Method for the preparation of 5-cyanophthalide |
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 |
NZ521204A (en) | 2000-03-13 | 2004-03-26 | H | Stepwise alkylation of 5-substituted 1-(4-fluorophenyl)- 1,3-dihydroisobenzofurans for preparing citalopram, an anti depressant |
HRP20020744A2 (en) | 2000-03-13 | 2004-12-31 | Lundbeck & Co As H | Method for the preparation of citalopram |
NL1017500C1 (nl) | 2000-03-13 | 2001-04-26 | Lundbeck & Co As H | Werkwijze voor de bereiding van Citalopram. |
PT1265882E (pt) | 2000-03-14 | 2004-06-30 | Lundbeck & Co As H | Metodo para preparacao de citalopram; composto e citalopram |
CN1418206A (zh) * | 2000-03-16 | 2003-05-14 | H·隆德贝克有限公司 | 5-氰基-1-(4-氟苯基)-1,3-二氢异苯并呋喃的制备方法 |
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 |
FI20011622L (fi) | 2000-08-18 | 2002-02-19 | Lundbeck & Co As H | Menetelmä sitalopraamin valmistamiseksi |
AU2001100405B4 (en) | 2000-12-22 | 2002-03-21 | H Lundbeck As | Process for the preparation of pure citalopram |
TR200200018T1 (tr) | 2000-12-28 | 2002-06-21 | H. Lundbeck A/S | Saf sitalopram hazırlanması için yöntem. |
EP1321464A1 (en) * | 2001-12-21 | 2003-06-25 | ICROM S.p.A. | Process for the preparation of 5-cyanophthalide and intermediates useful therein |
US7687645B2 (en) | 2003-03-21 | 2010-03-30 | H. Lundbeck A/S | Intermediates for the preparation of citalopram and escitalopram |
WO2004085416A1 (en) * | 2003-03-24 | 2004-10-07 | Hetero Drugs Limited | Novel crystalline forms of (s)-citalopram oxalate |
EP1777221A1 (en) * | 2005-10-14 | 2007-04-25 | Adorkem Technology SpA | Process for the preparation of 5-cyanophthalide starting from 5-carboxyphthalide |
Family Cites Families (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1143702A (ru) | 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 |
GB8814057D0 (en) | 1988-06-14 | 1988-07-20 | Lundbeck & Co As H | New enantiomers & their isolation |
DK213290D0 (da) | 1990-09-06 | 1990-09-06 | Lundbeck & Co As H | Treatment of cerebrovascular 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 |
ZA9711376B (en) | 1996-12-20 | 1998-07-21 | Lundbeck & Co As H | Indole or dihydroindole derivatives |
EA001728B1 (ru) * | 1997-07-08 | 2001-08-27 | Х.Лундбекк А/С | Способ получения циталопрама |
UA62985C2 (en) | 1997-11-10 | 2004-01-15 | Lunnbeck As H | A method for the preparation of citalopram |
BR9714925A (pt) | 1997-11-11 | 2003-07-22 | Lundbeck & Co As H | Método para preparação de citalopran, composto e composição farmacêutica antidepressiva |
DE69904853T2 (de) | 1998-10-20 | 2003-09-04 | Lundbeck As Valby H | Verfahren zur herstellung von citalopram |
IL143422A0 (en) | 1998-12-23 | 2002-04-21 | Lundbeck & Co As H | Method for the preparation of 5-cyanophthalide |
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 |
WO2000012044A2 (en) | 1999-10-25 | 2000-03-09 | H. Lundbeck A/S | Method for the preparation of citalopram |
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 |
-
1999
- 1999-12-22 IL IL14342299A patent/IL143422A0/xx not_active IP Right Cessation
- 1999-12-22 AU AU17742/00A patent/AU764161B2/en not_active Ceased
- 1999-12-22 PT PT99960958T patent/PT1140886E/pt unknown
- 1999-12-22 PL PL348608A patent/PL203275B1/pl not_active IP Right Cessation
- 1999-12-22 AT AT99960958T patent/ATE236145T1/de not_active IP Right Cessation
- 1999-12-22 DE DE69906580T patent/DE69906580T2/de not_active Expired - Lifetime
- 1999-12-22 BR BR9916955-0A patent/BR9916955A/pt not_active IP Right Cessation
- 1999-12-22 ES ES99960958T patent/ES2195644T3/es not_active Expired - Lifetime
- 1999-12-22 KR KR10-2001-7007686A patent/KR100454008B1/ko not_active Expired - Fee Related
- 1999-12-22 EA EA200100696A patent/EA003057B1/ru not_active IP Right Cessation
- 1999-12-22 TR TR2001/01796T patent/TR200101796T2/xx unknown
- 1999-12-22 CA CA002356188A patent/CA2356188C/en not_active Expired - Fee Related
- 1999-12-22 EP EP99960958A patent/EP1140886B1/en not_active Expired - Lifetime
- 1999-12-22 UA UA2001064498A patent/UA70979C2/ru unknown
- 1999-12-22 CZ CZ20012335A patent/CZ300408B6/cs not_active IP Right Cessation
- 1999-12-22 JP JP2000591023A patent/JP2002533450A/ja active Pending
- 1999-12-22 SK SK896-2001A patent/SK285530B6/sk unknown
- 1999-12-22 NZ NZ512073A patent/NZ512073A/en not_active IP Right Cessation
- 1999-12-22 WO PCT/DK1999/000728 patent/WO2000039112A1/en active IP Right Grant
- 1999-12-22 HK HK02105040.7A patent/HK1043130B/zh not_active IP Right Cessation
- 1999-12-22 HU HU0104856A patent/HUP0104856A3/hu unknown
- 1999-12-22 SI SI9930278T patent/SI1140886T1/xx unknown
- 1999-12-22 CN CNB998150002A patent/CN1149208C/zh not_active Expired - Fee Related
- 1999-12-22 DK DK99960958T patent/DK1140886T3/da active
- 1999-12-23 IT IT1999MI002696A patent/IT1315269B1/it active
- 1999-12-23 AR ARP990106726A patent/AR019791A1/es active IP Right Grant
-
2001
- 2001-05-22 IS IS5952A patent/IS2261B/is unknown
- 2001-05-24 ZA ZA200104262A patent/ZA200104262B/en unknown
- 2001-06-22 NO NO20013150A patent/NO326516B1/no not_active IP Right Cessation
- 2001-06-22 US US09/888,067 patent/US6392060B2/en not_active Expired - Fee Related
- 2001-06-27 BG BG105655A patent/BG64986B1/bg unknown
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
MM4A | Lapse of a eurasian patent due to non-payment of renewal fees within the time limit in the following designated state(s) |
Designated state(s): AM AZ KZ KG MD TJ TM |
|
MM4A | Lapse of a eurasian patent due to non-payment of renewal fees within the time limit in the following designated state(s) |
Designated state(s): BY RU |