ZA200105549B - Method for the preparation of 5-cyanophthalide. - Google Patents
Method for the preparation of 5-cyanophthalide. Download PDFInfo
- Publication number
- ZA200105549B ZA200105549B ZA200105549A ZA200105549A ZA200105549B ZA 200105549 B ZA200105549 B ZA 200105549B ZA 200105549 A ZA200105549 A ZA 200105549A ZA 200105549 A ZA200105549 A ZA 200105549A ZA 200105549 B ZA200105549 B ZA 200105549B
- Authority
- ZA
- South Africa
- Prior art keywords
- reaction
- formula
- carried out
- sulfolane
- dehydrating agent
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 34
- 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 claims description 14
- 238000002360 preparation method Methods 0.000 title claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 17
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 11
- 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 claims description 9
- -1 phenyloxy Chemical group 0.000 claims description 9
- 239000012024 dehydrating agents Substances 0.000 claims description 8
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- 229940124530 sulfonamide Drugs 0.000 claims description 6
- 150000003456 sulfonamides Chemical class 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 5
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 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 description 5
- 229960001653 citalopram Drugs 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 239000000935 antidepressant agent Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000005580 one pot reaction Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- ISMUWQMUWFPFBZ-UHFFFAOYSA-N 5-amino-3h-2-benzofuran-1-one Chemical compound NC1=CC=C2C(=O)OCC2=C1 ISMUWQMUWFPFBZ-UHFFFAOYSA-N 0.000 description 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 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 230000001430 anti-depressive effect Effects 0.000 description 2
- 229940005513 antidepressants Drugs 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- WSEQXVZVJXJVFP-UHFFFAOYSA-N 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile Chemical compound O1CC2=CC(C#N)=CC=C2C1(CCCN(C)C)C1=CC=C(F)C=C1 WSEQXVZVJXJVFP-UHFFFAOYSA-N 0.000 description 1
- FHYWZQPCLLAZEL-UHFFFAOYSA-N 1-oxo-3H-2-benzofuran-5-carbonitrile 1-oxo-3H-2-benzofuran-5-carboxylic acid Chemical compound O=C1OCc2cc(ccc12)C#N.OC(=O)c1ccc2C(=O)OCc2c1 FHYWZQPCLLAZEL-UHFFFAOYSA-N 0.000 description 1
- VIRVFXHPPWBDRD-UHFFFAOYSA-N 1-oxo-3h-2-benzofuran-5-carbonitrile;1-oxo-3h-2-benzofuran-5-carbonyl chloride Chemical compound N#CC1=CC=C2C(=O)OCC2=C1.ClC(=O)C1=CC=C2C(=O)OCC2=C1 VIRVFXHPPWBDRD-UHFFFAOYSA-N 0.000 description 1
- PXRKCOCTEMYUEG-UHFFFAOYSA-N 5-aminoisoindole-1,3-dione Chemical compound NC1=CC=C2C(=O)NC(=O)C2=C1 PXRKCOCTEMYUEG-UHFFFAOYSA-N 0.000 description 1
- VLQBZZYXIIHJIP-UHFFFAOYSA-N CN(C)CCC[Mg] Chemical compound CN(C)CCC[Mg] VLQBZZYXIIHJIP-UHFFFAOYSA-N 0.000 description 1
- NOYCNNBKNIAAHS-UHFFFAOYSA-N FC1=CC=C([Mg])C=C1 Chemical compound FC1=CC=C([Mg])C=C1 NOYCNNBKNIAAHS-UHFFFAOYSA-N 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000005406 washing Methods 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
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)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Indole Compounds (AREA)
- Furan Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DKPA199900128 | 1999-01-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200105549B true ZA200105549B (en) | 2002-07-05 |
Family
ID=8090069
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200105549A ZA200105549B (en) | 1999-01-29 | 2001-07-05 | Method for the preparation of 5-cyanophthalide. |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US6441201B1 (cs) |
| EP (1) | EP1150966B1 (cs) |
| JP (1) | JP2002535397A (cs) |
| KR (1) | KR100430327B1 (cs) |
| CN (1) | CN1158271C (cs) |
| AR (1) | AR022329A1 (cs) |
| AT (1) | ATE222900T1 (cs) |
| AU (1) | AU763666B2 (cs) |
| BG (1) | BG64924B1 (cs) |
| BR (1) | BR0008978A (cs) |
| CA (1) | CA2361395C (cs) |
| CZ (1) | CZ300257B6 (cs) |
| DE (1) | DE60000364T2 (cs) |
| DK (1) | DK1150966T3 (cs) |
| EA (1) | EA003257B1 (cs) |
| ES (1) | ES2180508T3 (cs) |
| HK (1) | HK1044342B (cs) |
| HU (1) | HUP0104976A3 (cs) |
| IL (2) | IL144114A0 (cs) |
| IS (1) | IS2223B (cs) |
| IT (1) | IT1317741B1 (cs) |
| NO (1) | NO326532B1 (cs) |
| NZ (1) | NZ512775A (cs) |
| PL (1) | PL198385B1 (cs) |
| PT (1) | PT1150966E (cs) |
| SI (1) | SI1150966T1 (cs) |
| SK (1) | SK284367B6 (cs) |
| TR (1) | TR200102135T2 (cs) |
| UA (1) | UA70987C2 (cs) |
| WO (1) | WO2000044738A1 (cs) |
| ZA (1) | ZA200105549B (cs) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR9915158B1 (pt) | 1998-10-20 | 2012-02-22 | método para preparação de citalopram, e, compostos da fórmula geral viii, ix e iv, ou qualquer de seus enantiÈmeros e sais com adição de ácido do mesmo. | |
| EP1140886B1 (en) | 1998-12-23 | 2003-04-02 | H. Lundbeck A/S | Method for the preparation of 5-cyanophthalide |
| CA2291129C (en) | 1999-04-14 | 2002-10-22 | H. Lundbeck A/S | Method for the preparation of 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 |
| DE69935355T2 (de) | 1999-10-25 | 2007-11-08 | H. Lundbeck A/S, Valby | Verfahren zur Herstellung von Citalopram |
| ES2169709A1 (es) | 1999-10-25 | 2002-07-01 | Lundbeck & Co As H | Metodo para la preparacion de citalopram |
| AR026063A1 (es) | 1999-11-01 | 2002-12-26 | Lundbeck & Co As H | Metodo para la preparacion de 5-carboxiftalida. |
| PT1246812E (pt) | 1999-12-28 | 2004-08-31 | Lundbeck & Co As H | Metodo para a preparacao de citalopram |
| SI1246813T1 (en) | 1999-12-30 | 2004-08-31 | H. Lundbeck A/S | Method for the preparation of citalopram |
| WO2001051477A1 (en) | 2000-01-14 | 2001-07-19 | H. Lundbeck A/S | Method for the preparation of 5-cyanophthalide |
| 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 |
| KR20020080481A (ko) | 2000-03-13 | 2002-10-23 | 하. 룬트벡 아크티에 셀스카브 | 시탈로프람의 제조 방법 |
| 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. |
| TR200400611T4 (tr) | 2000-03-14 | 2004-04-21 | H.Lundbeck A/S | Sitalopramın preparasyon metodu |
| CZ20023406A3 (cs) * | 2000-03-16 | 2003-01-15 | H. Lundbeck A/S | Způsob výroby 5-kyano-1-(4-fluorfenyl)-1,3-dihydroisobenzofuranu |
| 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 |
| IL144817A0 (en) * | 2000-08-18 | 2002-06-30 | Lundbeck & Co As H | Method for the preparation of citalopram |
| CA2360303C (en) | 2000-12-22 | 2003-08-12 | Marco Villa | Process for the preparation of pure citalopram |
| CA2359810C (en) | 2000-12-28 | 2002-11-05 | H. Lundbeck A/S | Process for the preparation of pure citalopram |
| GR1004635B (el) * | 2001-08-14 | 2004-07-14 | H@Αlundbeckαa@Sαα | Μεθοδοσαπαρασκευησατησασιταλοπραμης@αα |
| EP1321464A1 (en) * | 2001-12-21 | 2003-06-25 | ICROM S.p.A. | Process for the preparation of 5-cyanophthalide and intermediates useful therein |
| PE20040991A1 (es) | 2002-08-12 | 2004-12-27 | Lundbeck & Co As H | Separacion de intermediarios para la preparacion de escitalopram |
| CN101362743A (zh) | 2003-03-21 | 2009-02-11 | H.隆德贝克有限公司 | 用于制备西酞普兰和依他普仑的中间体 |
| 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 |
| CN119638868B (zh) * | 2025-02-11 | 2025-05-13 | 济南市规划设计研究院 | 苯并呋喃酮壳聚糖复合物、其制备方法及其在历史街区更新领域的应用 |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1143702A (cs) | 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 |
| US5296507A (en) | 1990-09-06 | 1994-03-22 | H.Lundbeck A/S | Treatment of cerbrovascular 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 |
| ATE205824T1 (de) * | 1997-07-08 | 2001-10-15 | Lundbeck & Co As H | Verfahren zur herstellung von citalopram |
| 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 |
| BR9915158B1 (pt) | 1998-10-20 | 2012-02-22 | método para preparação de citalopram, e, compostos da fórmula geral viii, ix e iv, ou qualquer de seus enantiÈmeros e sais com adição de ácido do mesmo. | |
| EP1140886B1 (en) * | 1998-12-23 | 2003-04-02 | H. Lundbeck A/S | Method for the preparation of 5-cyanophthalide |
| CA2291129C (en) | 1999-04-14 | 2002-10-22 | H. Lundbeck A/S | Method for the preparation of 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 |
| ES2169709A1 (es) | 1999-10-25 | 2002-07-01 | Lundbeck & Co As H | Metodo para la preparacion de 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 |
| FR2805812A1 (fr) | 2000-02-24 | 2001-09-07 | Lundbeck & Co As H | Procede de preparation du citalopram |
| IES20010143A2 (en) | 2000-02-24 | 2001-07-25 | 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 |
| IL144817A0 (en) | 2000-08-18 | 2002-06-30 | Lundbeck & Co As H | Method for the preparation of citalopram |
| CA2360303C (en) | 2000-12-22 | 2003-08-12 | Marco Villa | Process for the preparation of pure citalopram |
| CA2359810C (en) | 2000-12-28 | 2002-11-05 | H. Lundbeck A/S | Process for the preparation of pure citalopram |
-
2000
- 2000-01-21 AR ARP000100271A patent/AR022329A1/es active IP Right Grant
- 2000-01-26 CN CNB008030480A patent/CN1158271C/zh not_active Expired - Fee Related
- 2000-01-26 EA EA200100834A patent/EA003257B1/ru not_active IP Right Cessation
- 2000-01-26 IL IL14411400A patent/IL144114A0/xx active IP Right Grant
- 2000-01-26 PT PT00901482T patent/PT1150966E/pt unknown
- 2000-01-26 CA CA002361395A patent/CA2361395C/en not_active Expired - Fee Related
- 2000-01-26 KR KR10-2001-7008663A patent/KR100430327B1/ko not_active Expired - Fee Related
- 2000-01-26 PL PL349908A patent/PL198385B1/pl not_active IP Right Cessation
- 2000-01-26 HU HU0104976A patent/HUP0104976A3/hu unknown
- 2000-01-26 SI SI200030024T patent/SI1150966T1/xx unknown
- 2000-01-26 TR TR2001/02135T patent/TR200102135T2/xx unknown
- 2000-01-26 EP EP00901482A patent/EP1150966B1/en not_active Expired - Lifetime
- 2000-01-26 JP JP2000595994A patent/JP2002535397A/ja active Pending
- 2000-01-26 UA UA2001075226A patent/UA70987C2/uk unknown
- 2000-01-26 SK SK1056-2001A patent/SK284367B6/sk not_active IP Right Cessation
- 2000-01-26 HK HK02105984.5A patent/HK1044342B/zh not_active IP Right Cessation
- 2000-01-26 WO PCT/DK2000/000032 patent/WO2000044738A1/en not_active Ceased
- 2000-01-26 ES ES00901482T patent/ES2180508T3/es not_active Expired - Lifetime
- 2000-01-26 NZ NZ512775A patent/NZ512775A/en not_active IP Right Cessation
- 2000-01-26 AT AT00901482T patent/ATE222900T1/de not_active IP Right Cessation
- 2000-01-26 CZ CZ20012734A patent/CZ300257B6/cs not_active IP Right Cessation
- 2000-01-26 DE DE60000364T patent/DE60000364T2/de not_active Expired - Lifetime
- 2000-01-26 AU AU22782/00A patent/AU763666B2/en not_active Ceased
- 2000-01-26 BR BR0008978-8A patent/BR0008978A/pt active Search and Examination
- 2000-01-26 DK DK00901482T patent/DK1150966T3/da active
- 2000-01-27 IT IT2000MI000112A patent/IT1317741B1/it active
-
2001
- 2001-06-28 IS IS5982A patent/IS2223B/is unknown
- 2001-07-02 IL IL144114A patent/IL144114A/en not_active IP Right Cessation
- 2001-07-05 ZA ZA200105549A patent/ZA200105549B/en unknown
- 2001-07-10 BG BG105692A patent/BG64924B1/bg unknown
- 2001-07-26 NO NO20013667A patent/NO326532B1/no not_active IP Right Cessation
- 2001-07-27 US US09/917,180 patent/US6441201B1/en not_active Expired - Fee Related
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