UA73336C2 - A method for the preparation of 5-cyano-phtalid - Google Patents

A method for the preparation of 5-cyano-phtalid Download PDF

Info

Publication number: UA73336C2
Authority: UA; Ukraine
Prior art keywords: reaction; differs; formula; carried out; fact
Prior art date: 1999-12-30

Application number

UA2002065265A

Other languages

English (en)

Ukrainian (uk)

Original Assignee

Lundbeck & Co As H

Priority date (The priority date 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 date listed.)

1999-12-30

Filing date

1999-12-30

Publication date

2005-07-15

1999-12-30 Application filed by Lundbeck & Co As H filed Critical Lundbeck & Co As H

2005-07-15 Publication of UA73336C2 publication Critical patent/UA73336C2/uk

Links

238000000034 method Methods 0.000 title claims abstract description 29
238000002360 preparation method Methods 0.000 title abstract description 5
238000006243 chemical reaction Methods 0.000 claims description 25
239000003054 catalyst Substances 0.000 claims description 13
239000002904 solvent Substances 0.000 claims description 11
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 10
WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 claims description 7
XEEGWTLAFIZLSF-UHFFFAOYSA-N 1-oxo-3h-2-benzofuran-5-carbonitrile Chemical compound N#CC1=CC=C2C(=O)OCC2=C1 XEEGWTLAFIZLSF-UHFFFAOYSA-N 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
230000005855 radiation Effects 0.000 claims description 3
239000002608 ionic liquid Substances 0.000 claims description 2
239000007858 starting material Substances 0.000 claims 4
CQAKANQMFXBJJQ-UHFFFAOYSA-N 5-iodo-3h-2-benzofuran-1-one Chemical compound IC1=CC=C2C(=O)OCC2=C1 CQAKANQMFXBJJQ-UHFFFAOYSA-N 0.000 claims 2
UBRQBEBBOSKYLQ-UHFFFAOYSA-N 5-chloro-3h-2-benzofuran-1-one Chemical compound ClC1=CC=C2C(=O)OCC2=C1 UBRQBEBBOSKYLQ-UHFFFAOYSA-N 0.000 claims 1
101150024701 PPH3 gene Proteins 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
239000003638 chemical reducing agent Substances 0.000 claims 1
229910052736 halogen Inorganic materials 0.000 claims 1
150000002367 halogens Chemical class 0.000 claims 1
229910052757 nitrogen Inorganic materials 0.000 claims 1
238000012876 topography Methods 0.000 claims 1
125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 claims 1
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 description 13
229960001653 citalopram Drugs 0.000 abstract description 13
150000001875 compounds Chemical class 0.000 abstract description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 9
239000000543 intermediate Substances 0.000 description 8
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
239000000203 mixture Substances 0.000 description 6
239000000538 analytical sample Substances 0.000 description 5
238000001035 drying Methods 0.000 description 5
238000001914 filtration Methods 0.000 description 5
238000001953 recrystallisation Methods 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
239000000935 antidepressant agent Substances 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
238000004128 high performance liquid chromatography Methods 0.000 description 4
150000002825 nitriles Chemical group 0.000 description 4
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
229910052786 argon Inorganic materials 0.000 description 3
239000012300 argon atmosphere Substances 0.000 description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
230000005587 bubbling Effects 0.000 description 3
239000001301 oxygen Substances 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
230000001430 anti-depressive effect Effects 0.000 description 2
229940005513 antidepressants Drugs 0.000 description 2
125000004093 cyano group Chemical group *C#N 0.000 description 2
230000000694 effects Effects 0.000 description 2
230000002349 favourable effect Effects 0.000 description 2
229910052759 nickel Inorganic materials 0.000 description 2
238000003756 stirring Methods 0.000 description 2
-1 4-fluorophenylmagnesium halide Chemical class 0.000 description 1
ANYWGXDASKQYAD-UHFFFAOYSA-N 5-nitroisoindole-1,3-dione Chemical compound [O-][N+](=O)C1=CC=C2C(=O)NC(=O)C2=C1 ANYWGXDASKQYAD-UHFFFAOYSA-N 0.000 description 1
206010012289 Dementia Diseases 0.000 description 1
238000003747 Grignard reaction Methods 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
101100496087 Mus musculus Clec12a gene Proteins 0.000 description 1
101100412856 Mus musculus Rhod gene Proteins 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
101100242191 Tetraodon nigroviridis rho gene Proteins 0.000 description 1
241000464917 Vieja Species 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
208000026106 cerebrovascular disease Diseases 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000012467 final product Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
229910001385 heavy metal Inorganic materials 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
239000003446 ligand Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052748 manganese Inorganic materials 0.000 description 1
239000011572 manganese Substances 0.000 description 1
AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
239000012454 non-polar solvent Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000004064 recycling Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229940076279 serotonin Drugs 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 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
- C07D307/88—Benzo [c] furans; Hydrogenated benzo [c] furans with one oxygen atom directly attached in position 1 or 3
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
- B01J23/44—Palladium
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/74—Iron group metals
- B01J23/755—Nickel

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Chemical Kinetics & Catalysis (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Steroid Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Furan Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Cephalosporin Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

UA2002065265A 1999-12-30 1999-12-30 A method for the preparation of 5-cyano-phtalid UA73336C2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
PCT/DK1999/000740 WO2001049672A1 (en)	1999-12-30	1999-12-30	Method for the preparation of citalopram

Publications (1)

Publication Number	Publication Date
UA73336C2 true UA73336C2 (en)	2005-07-15

Family

ID=8157174

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UA2002065265A UA73336C2 (en)	1999-12-30	1999-12-30	A method for the preparation of 5-cyano-phtalid

Country Status (28)

Country	Link
US (2)	US20020198391A1 (is)
EP (1)	EP1246813B1 (is)
JP (1)	JP2003519218A (is)
KR (1)	KR100653141B1 (is)
CN (1)	CN1211377C (is)
AT (1)	ATE253568T1 (is)
AU (1)	AU1858400A (is)
BR (1)	BR9917604A (is)
CA (1)	CA2395733C (is)
CZ (1)	CZ20022627A3 (is)
DE (1)	DE69912652T2 (is)
DK (1)	DK1246813T3 (is)
EA (1)	EA004055B1 (is)
ES (1)	ES2207312T3 (is)
HK (1)	HK1052512B (is)
HR (1)	HRP20020633A2 (is)
HU (1)	HUP0203840A3 (is)
IL (2)	IL150367A0 (is)
IS (1)	IS2167B (is)
MX (1)	MXPA02006504A (is)
NO (1)	NO328359B1 (is)
PL (1)	PL198803B1 (is)
PT (1)	PT1246813E (is)
SI (1)	SI1246813T1 (is)
SK (1)	SK11052002A3 (is)
TR (1)	TR200201688T2 (is)
UA (1)	UA73336C2 (is)
WO (1)	WO2001049672A1 (is)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DK1173431T4 (da)	1999-04-14	2010-01-04	Lundbeck & Co As H	Fremgangsmåde til fremstilling af citalopram
JP2003519136A (ja)	1999-12-28	2003-06-17	ハー・ルンドベック・アクチエゼルスカベット	シタロプラムの製造方法
AU3033700A (en)	2000-01-14	2001-07-24	H. Lundbeck A/S	Method for the preparation of 5-cyanophthalide
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
AU2001242298A1 (en)	2000-03-13	2001-09-24	H Lunbeck A/S	Method for the preparation of citalopram
KR20020080485A (ko)	2000-03-13	2002-10-23	하. 룬트벡 아크티에 셀스카브	5-치환 1-(4-플루오로페닐)-1,3-디히드로이소벤조푸란의단계적 알킬화
NL1017500C1 (nl)	2000-03-13	2001-04-26	Lundbeck & Co As H	Werkwijze voor de bereiding van Citalopram.
ES2214400T3 (es)	2000-03-14	2004-09-16	H. Lundbeck A/S	Metodo para la preparacion de citalopram.
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
US6339182B1 (en) *	2000-06-20	2002-01-15	Chevron U.S.A. Inc.	Separation of olefins from paraffins using ionic liquid solutions
AU2003223105A1 (en) *	2003-03-24	2004-10-18	Hetero Drugs Limited	Novel crystalline forms of (s)-citalopram oxalate
CN100457747C (zh) *	2006-11-21	2009-02-04	浙江大学	抗抑郁药西酞普兰关键中间体5-氰基苯酞的制备工艺
CN103127815B (zh) *	2013-02-19	2015-10-28	浙江大学	一种利用卤硫作用提高二氧化硫捕集性能的方法

Family Cites Families (28)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1143703A (is)	1965-03-18
GB1526331A (en) *	1976-01-14	1978-09-27	Kefalas As	Phthalanes
US4665181A (en) *	1984-05-17	1987-05-12	Pennwalt Corporation	Anti-inflammatory phthalazinones
GB8419963D0 (en) *	1984-08-06	1984-09-12	Lundbeck & Co As H	Intermediate compound and method
US5296507A (en)	1990-09-06	1994-03-22	H.Lundbeck A/S	Treatment of cerbrovascular disorders
JPH0881456A (ja) *	1994-09-14	1996-03-26	Sumitomo Chem Co Ltd	１，１，３，３−テトラクロロ−１，３−ジヒドロイソベンゾフラン誘導体の製造法
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
SK283309B6 (sk) *	1997-07-08	2003-05-02	H. Lundbeck A/S	Spôsob výroby citalopramu a medziprodukty
UA62985C2 (en)	1997-11-10	2004-01-15	Lunnbeck As H	A method for the preparation of citalopram
DK1042310T3 (da)	1997-11-11	2002-12-02	Lundbeck & Co As H	Fremgangsmåde til fremstilling af citalopram
ES2189502T3 (es)	1998-10-20	2003-07-01	Lundbeck & Co As H	Metodo para la prevencion de 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
DK1173431T4 (da)	1999-04-14	2010-01-04	Lundbeck & Co As H	Fremgangsmåde til fremstilling af citalopram
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
CH692421A5 (de)	1999-10-25	2002-06-14	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.
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
JP2003519136A (ja)	1999-12-28	2003-06-17	ハー・ルンドベック・アクチエゼルスカベット	シタロプラムの製造方法
AU3033700A (en)	2000-01-14	2001-07-24	H. Lundbeck A/S	Method for the preparation of 5-cyanophthalide
IES20010143A2 (en)	2000-02-24	2001-07-25	Lundbeck & Co As H	Method for the preparation of citalopram
FR2805812A1 (fr)	2000-02-24	2001-09-07	Lundbeck & Co As H	Procede de preparation du citalopram
GB0005477D0 (en)	2000-03-07	2000-04-26	Resolution Chemicals Limited	Process for the preparation of citalopram
CA2354877C (en)	2000-08-18	2006-05-02	H. Lundbeck A/S	Method for the preparation of citalopram
CA2360303C (en)	2000-12-22	2003-08-12	Marco Villa	Process for the preparation of pure citalopram
SK284418B6 (sk)	2000-12-28	2005-04-01	H. Lundbeck A/S	Spôsob výroby citalopramu

1999
- 1999-12-30 DK DK99962133T patent/DK1246813T3/da active
- 1999-12-30 ES ES99962133T patent/ES2207312T3/es not_active Expired - Lifetime
- 1999-12-30 AT AT99962133T patent/ATE253568T1/de not_active IP Right Cessation
- 1999-12-30 HR HRP20020633 patent/HRP20020633A2/hr not_active Application Discontinuation
- 1999-12-30 CN CNB998170674A patent/CN1211377C/zh not_active Expired - Fee Related
- 1999-12-30 HK HK03104874.0A patent/HK1052512B/zh not_active IP Right Cessation
- 1999-12-30 CA CA002395733A patent/CA2395733C/en not_active Expired - Fee Related
- 1999-12-30 DE DE69912652T patent/DE69912652T2/de not_active Expired - Lifetime
- 1999-12-30 WO PCT/DK1999/000740 patent/WO2001049672A1/en not_active Ceased
- 1999-12-30 PL PL355531A patent/PL198803B1/pl not_active IP Right Cessation
- 1999-12-30 EA EA200200728A patent/EA004055B1/ru not_active IP Right Cessation
- 1999-12-30 UA UA2002065265A patent/UA73336C2/uk unknown
- 1999-12-30 TR TR2002/01688T patent/TR200201688T2/xx unknown
- 1999-12-30 SK SK1105-2002A patent/SK11052002A3/sk unknown
- 1999-12-30 HU HU0203840A patent/HUP0203840A3/hu unknown
- 1999-12-30 PT PT99962133T patent/PT1246813E/pt unknown
- 1999-12-30 JP JP2001550212A patent/JP2003519218A/ja active Pending
- 1999-12-30 IL IL15036799A patent/IL150367A0/xx unknown
- 1999-12-30 KR KR1020027008572A patent/KR100653141B1/ko not_active Expired - Fee Related
- 1999-12-30 EP EP99962133A patent/EP1246813B1/en not_active Expired - Lifetime
- 1999-12-30 CZ CZ20022627A patent/CZ20022627A3/cs unknown
- 1999-12-30 SI SI9930473T patent/SI1246813T1/xx unknown
- 1999-12-30 BR BR9917604-1A patent/BR9917604A/pt not_active Application Discontinuation
- 1999-12-30 MX MXPA02006504A patent/MXPA02006504A/es active IP Right Grant
- 1999-12-30 AU AU18584/00A patent/AU1858400A/en not_active Abandoned
2002
- 2002-06-19 IS IS6433A patent/IS2167B/is unknown
- 2002-06-23 IL IL150367A patent/IL150367A/en not_active IP Right Cessation
- 2002-06-27 US US10/186,337 patent/US20020198391A1/en not_active Abandoned
- 2002-06-28 NO NO20023150A patent/NO328359B1/no not_active IP Right Cessation
2005
- 2005-11-23 US US11/285,922 patent/US7271273B2/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
DE69912652D1 (de)	2003-12-11
IL150367A (en)	2010-06-16
EP1246813A1 (en)	2002-10-09
NO20023150L (no)	2002-06-28
HUP0203840A3 (en)	2005-02-28
EA200200728A1 (ru)	2002-12-26
NO328359B1 (no)	2010-02-01
AU1858400A (en)	2001-07-16
KR20020073495A (ko)	2002-09-26
SK11052002A3 (sk)	2003-01-09
MXPA02006504A (es)	2002-12-09
PL355531A1 (en)	2004-05-04
CA2395733C (en)	2007-03-20
EP1246813B1 (en)	2003-11-05
WO2001049672A1 (en)	2001-07-12
HUP0203840A2 (en)	2003-05-28
PL198803B1 (pl)	2008-07-31
CA2395733A1 (en)	2001-07-12
IS2167B (is)	2006-11-15
CZ20022627A3 (cs)	2002-10-16
IS6433A (is)	2002-06-19
CN1211377C (zh)	2005-07-20
DK1246813T3 (da)	2004-03-01
KR100653141B1 (ko)	2006-12-01
BR9917604A (pt)	2002-12-31
ES2207312T3 (es)	2004-05-16
HRP20020633A2 (en)	2004-12-31
US20020198391A1 (en)	2002-12-26
US7271273B2 (en)	2007-09-18
JP2003519218A (ja)	2003-06-17
PT1246813E (pt)	2004-02-27
ATE253568T1 (de)	2003-11-15
SI1246813T1 (en)	2004-08-31
TR200201688T2 (tr)	2002-11-21
NO20023150D0 (no)	2002-06-28
EA004055B1 (ru)	2003-12-25
US20060079700A1 (en)	2006-04-13
HK1052512A1 (en)	2003-09-19
IL150367A0 (en)	2002-12-01
DE69912652T2 (de)	2004-06-09
HK1052512B (zh)	2006-03-03
CN1391566A (zh)	2003-01-15

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