HK1083828A1 - Method for the separation of intermediates which may be used for the preparation of escitalopram - Google Patents
Method for the separation of intermediates which may be used for the preparation of escitalopramInfo
- Publication number
- HK1083828A1 HK1083828A1 HK06103819.7A HK06103819A HK1083828A1 HK 1083828 A1 HK1083828 A1 HK 1083828A1 HK 06103819 A HK06103819 A HK 06103819A HK 1083828 A1 HK1083828 A1 HK 1083828A1
- Authority
- HK
- Hong Kong
- Prior art keywords
- escitalopram
- intermediates
- separation
- preparation
- Prior art date
Links
- WSEQXVZVJXJVFP-FQEVSTJZSA-N escitalopram Chemical compound C1([C@]2(C3=CC=C(C=C3CO2)C#N)CCCN(C)C)=CC=C(F)C=C1 WSEQXVZVJXJVFP-FQEVSTJZSA-N 0.000 title 1
- 229960004341 escitalopram Drugs 0.000 title 1
- 239000000543 intermediate Substances 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- 238000000926 separation method Methods 0.000 title 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/53—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and hydroxy groups bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B57/00—Separation of optically-active compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/32—Separation; Purification; Stabilisation; Use of additives
- C07C253/34—Separation; Purification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/34—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring with cyano groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by unsaturated carbon chains
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
- C07C255/59—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen 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
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/001—Amines; Imines
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/002—Nitriles (-CN)
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/008—Preparation of nitrogen-containing organic compounds containing a N-O bond, e.g. nitro (-NO2), nitroso (-NO)
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/02—Amides, e.g. chloramphenicol or polyamides; Imides or polyimides; Urethanes, i.e. compounds comprising N-C=O structural element or polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
- C12P41/006—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by reactions involving C-N bonds, e.g. nitriles, amides, hydantoins, carbamates, lactames, transamination reactions, or keto group formation from racemic mixtures
- C12P41/007—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by reactions involving C-N bonds, e.g. nitriles, amides, hydantoins, carbamates, lactames, transamination reactions, or keto group formation from racemic mixtures by reactions involving acyl derivatives of racemic amines
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/02—Preparation of oxygen-containing organic compounds containing a hydroxy group
- C12P7/22—Preparation of oxygen-containing organic compounds containing a hydroxy group aromatic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Microbiology (AREA)
- Genetics & Genomics (AREA)
- Analytical Chemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Hydrogenated Pyridines (AREA)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
HK08103365.3A HK1131514A1 (en) | 2002-08-12 | 2003-08-12 | Method of isolation and purification |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US40308802P | 2002-08-12 | 2002-08-12 | |
DKPA200201201 | 2002-08-12 | ||
PCT/DK2003/000537 WO2004014821A1 (fr) | 2002-08-12 | 2003-08-12 | Procede de separation de produits intermediaires pouvant etre utilises dans la preparation d'escitalopram |
Publications (1)
Publication Number | Publication Date |
---|---|
HK1083828A1 true HK1083828A1 (en) | 2006-07-14 |
Family
ID=34717090
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HK08103365.3A HK1131514A1 (en) | 2002-08-12 | 2003-08-12 | Method of isolation and purification |
HK06103819.7A HK1083828A1 (en) | 2002-08-12 | 2003-08-12 | Method for the separation of intermediates which may be used for the preparation of escitalopram |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HK08103365.3A HK1131514A1 (en) | 2002-08-12 | 2003-08-12 | Method of isolation and purification |
Country Status (24)
Country | Link |
---|---|
US (2) | US20070129561A1 (fr) |
EP (2) | EP1534654A1 (fr) |
JP (3) | JP4694837B2 (fr) |
KR (1) | KR20050053618A (fr) |
CN (2) | CN100548939C (fr) |
AR (1) | AR040970A1 (fr) |
AU (1) | AU2003250321B2 (fr) |
BR (1) | BR0313114A (fr) |
CA (1) | CA2495118C (fr) |
EA (1) | EA011762B1 (fr) |
HK (2) | HK1131514A1 (fr) |
IL (1) | IL166319A0 (fr) |
IS (1) | IS7642A (fr) |
ME (1) | MEP1608A (fr) |
MX (1) | MXPA05001400A (fr) |
NO (1) | NO20051292L (fr) |
NZ (1) | NZ537785A (fr) |
PE (1) | PE20040991A1 (fr) |
PL (1) | PL374835A1 (fr) |
RS (1) | RS20050092A (fr) |
TW (1) | TWI306846B (fr) |
UA (1) | UA78840C2 (fr) |
WO (1) | WO2004014821A1 (fr) |
ZA (1) | ZA200500728B (fr) |
Families Citing this family (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20050154052A1 (en) * | 2003-03-24 | 2005-07-14 | Hetero Drugs Limited | Novel crystalline forms of (s)-citalopram oxalate |
ES2228274B1 (es) * | 2003-09-24 | 2006-06-01 | Astur Pharma, S.A. | Sintesis quimioenzimatica de (+)-citalopram y (-)-citalopram. |
TWI339651B (en) | 2004-02-12 | 2011-04-01 | Lundbeck & Co As H | Method for the separation of intermediates which may be used for the preparation of escitalopram |
AU2005218713B2 (en) * | 2004-03-05 | 2009-11-19 | H. Lundbeck A/S | Crystalline composition containing escitalopram oxalate |
US20050196453A1 (en) | 2004-03-05 | 2005-09-08 | H. Lundbeck A/S | Crystalline composition containing escitalopram |
ITMI20040717A1 (it) * | 2004-04-09 | 2004-07-09 | Adorkem Technology Spa | Procedimento chemo-enzimatico per la preparazione dell'escitalopram |
ITMI20041872A1 (it) | 2004-10-01 | 2005-01-01 | Adorkem Technology Spa | Processo per la preparazione di citalopram e di scitalopram |
EP1736550A1 (fr) * | 2005-06-22 | 2006-12-27 | Adorkem Technology SpA | Procédé chémo-enzymatique pour la production d' escitalopram |
GB0601286D0 (en) | 2006-01-23 | 2006-03-01 | Sandoz Ag | Asymmetric synthesis |
WO2008059514A2 (fr) * | 2006-07-31 | 2008-05-22 | Cadila Healthcare Limited | Procédé de préparation d'escitalopram |
US7686946B2 (en) | 2007-08-17 | 2010-03-30 | Uop Llc | Method of altering a feed to a reaction zone |
CN100548974C (zh) * | 2007-10-11 | 2009-10-14 | 浙江大学 | 西酞普兰中间体的萃取分离方法 |
TWI369202B (en) * | 2008-01-25 | 2012-08-01 | Xenoport Inc | Enantiomerically resolving acyloxyalkyl thiocarbonates used in synthesizing acyloxyalkyl carbamate prodrugs |
ITMI20120448A1 (it) | 2012-01-30 | 2013-07-31 | Carthesia Sas | Composizione liofilizzata di escitalopram ossalato per somministrazione sublinguale |
ES2554563B2 (es) * | 2014-05-05 | 2016-08-16 | Universidad De Sevilla | Cepas bacterianas y sus usos en reacciones de acilación y/o desacilación |
WO2017009866A1 (fr) * | 2015-07-11 | 2017-01-19 | Ipca Laboratories Limited | Nouveau procédé de récupération et de recyclage de 4- (4-diméthylamino)-1-(4 '-fluorophényl)-1-(hydroxybutyl)-3-(hydroxyméthyl)-benzonitrile racémique |
Family Cites Families (34)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
EP0285287A3 (fr) * | 1987-03-23 | 1990-08-16 | Smithkline Beecham Corporation | Emploi de 3-benzazépines pour le traitement des troubles de la mobilité gastro-intestinale |
GB8814057D0 (en) | 1988-06-14 | 1988-07-20 | Lundbeck & Co As H | New enantiomers & their isolation |
JP3097145B2 (ja) | 1991-02-27 | 2000-10-10 | 日産化学工業株式会社 | コーリーラクトンジオールの光学分割方法 |
SE511903C2 (sv) | 1996-06-28 | 1999-12-13 | Sca Hygiene Prod Ab | Absorberande alster innefattande en absorptionskropp med förbättrade vätskeinsläppsegenskaper |
IT236075Y1 (it) | 1997-06-26 | 2000-07-26 | Emilio Brocco | Macchina segatrice per la divisione in lastre di blocchi di materialelapideo |
UA62985C2 (en) * | 1997-11-10 | 2004-01-15 | Lunnbeck As H | A method for the preparation of citalopram |
DE1042310T1 (de) | 1997-11-11 | 2001-04-19 | Lundbeck & Co As H | Verfahren zur herstellung von citaloprame |
JPH1129418A (ja) * | 1998-06-12 | 1999-02-02 | Takeda Chem Ind Ltd | 農園芸用殺虫殺菌組成物 |
DE19832547A1 (de) | 1998-07-21 | 2000-01-27 | Basf Ag | Enzymhaltige Polymere |
US6294571B1 (en) * | 1998-09-11 | 2001-09-25 | Independent Ink, Inc. | Method for using neem extracts and derivatives for protecting wood and other cellulosic composites |
PL199423B1 (pl) | 1998-10-20 | 2008-09-30 | Lundbeck & Co As H | Sposób wytwarzania citalopramu |
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 |
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 |
DK1228056T3 (da) * | 1999-10-25 | 2005-01-24 | Lundbeck & Co As H | Fremgangsmåde til fremstilling af citalopram |
CH692421A5 (de) * | 1999-10-25 | 2002-06-14 | Lundbeck & Co As H | Verfahren zur Herstellung von Citalopram. |
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 |
IL151566A0 (en) | 2000-03-13 | 2003-04-10 | Lundbeck & Co As H | Stepwise alkylation of 5-substituted 1-(4-fluorophenyl)-1,3-dihydroisobenzofurans |
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 |
FI20011622L (fi) * | 2000-08-18 | 2002-02-19 | Lundbeck & Co As H | Menetelmä sitalopraamin valmistamiseksi |
AR034612A1 (es) * | 2001-06-25 | 2004-03-03 | Lundbeck & Co As H | Proceso para la preparacion del citalopram racemico y/o del s- o r-citalopram mediante la separacion de una mezcla de r- y s-citalopram |
AR034759A1 (es) | 2001-07-13 | 2004-03-17 | Lundbeck & Co As H | Metodo para la preparacion de escitalopram |
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 |
CA2381341A1 (fr) * | 2002-04-09 | 2003-10-09 | Torcan Chemical Ltd. | Methode de preparation et intermediaires connexes pour la synthese de l'escitalopram |
CN1510024A (zh) * | 2002-12-24 | 2004-07-07 | 北京德众万全药物技术开发有限公司 | 可用于制备西酞普兰(s)-对映异构体的新的化合物及其制备方法 |
-
2003
- 2003-08-11 AR ARP030102904A patent/AR040970A1/es unknown
- 2003-08-11 TW TW092121967A patent/TWI306846B/zh not_active IP Right Cessation
- 2003-08-11 PE PE2003000799A patent/PE20040991A1/es not_active Application Discontinuation
- 2003-08-12 EP EP03783962A patent/EP1534654A1/fr not_active Withdrawn
- 2003-08-12 EP EP11165320A patent/EP2360150A1/fr not_active Withdrawn
- 2003-08-12 AU AU2003250321A patent/AU2003250321B2/en not_active Ceased
- 2003-08-12 NZ NZ537785A patent/NZ537785A/en unknown
- 2003-08-12 RS YUP-2005/0092A patent/RS20050092A/sr unknown
- 2003-08-12 HK HK08103365.3A patent/HK1131514A1/xx not_active IP Right Cessation
- 2003-08-12 IL IL16631903A patent/IL166319A0/xx unknown
- 2003-08-12 CN CNB03819001XA patent/CN100548939C/zh not_active Expired - Lifetime
- 2003-08-12 CA CA2495118A patent/CA2495118C/fr not_active Expired - Fee Related
- 2003-08-12 PL PL03374835A patent/PL374835A1/xx unknown
- 2003-08-12 CN CN2007101018055A patent/CN101045664B/zh not_active Expired - Lifetime
- 2003-08-12 MX MXPA05001400A patent/MXPA05001400A/es active IP Right Grant
- 2003-08-12 WO PCT/DK2003/000537 patent/WO2004014821A1/fr active Application Filing
- 2003-08-12 KR KR1020057002554A patent/KR20050053618A/ko not_active Application Discontinuation
- 2003-08-12 HK HK06103819.7A patent/HK1083828A1/xx not_active IP Right Cessation
- 2003-08-12 EA EA200500349A patent/EA011762B1/ru not_active IP Right Cessation
- 2003-08-12 BR BR0313114-9A patent/BR0313114A/pt not_active Application Discontinuation
- 2003-08-12 JP JP2004526641A patent/JP4694837B2/ja not_active Expired - Lifetime
- 2003-08-12 ME MEP-16/08A patent/MEP1608A/xx unknown
- 2003-08-12 US US10/524,937 patent/US20070129561A1/en not_active Abandoned
- 2003-12-08 UA UAA200501846A patent/UA78840C2/uk unknown
-
2005
- 2005-01-12 IS IS7642A patent/IS7642A/is unknown
- 2005-01-25 ZA ZA200500728A patent/ZA200500728B/xx unknown
- 2005-03-14 NO NO20051292A patent/NO20051292L/no not_active Application Discontinuation
-
2010
- 2010-02-17 JP JP2010032381A patent/JP5520077B2/ja not_active Expired - Lifetime
- 2010-05-17 US US12/781,026 patent/US8067640B2/en not_active Expired - Fee Related
- 2010-11-25 JP JP2010262040A patent/JP2011055842A/ja active Pending
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PC | Patent ceased (i.e. patent has lapsed due to the failure to pay the renewal fee) |
Effective date: 20140812 |