SK6742001A3 - 2-phenylbenzimidazoles and 2-phenylindoles, and production and use thereof - Google Patents
2-phenylbenzimidazoles and 2-phenylindoles, and production and use thereof Download PDFInfo
- Publication number
- SK6742001A3 SK6742001A3 SK674-2001A SK6742001A SK6742001A3 SK 6742001 A3 SK6742001 A3 SK 6742001A3 SK 6742001 A SK6742001 A SK 6742001A SK 6742001 A3 SK6742001 A3 SK 6742001A3
- Authority
- SK
- Slovakia
- Prior art keywords
- alkyl
- treatment
- compounds
- formula
- hydrogen
- Prior art date
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- DWYHDSLIWMUSOO-UHFFFAOYSA-N 2-phenyl-1h-benzimidazole Chemical class C1=CC=CC=C1C1=NC2=CC=CC=C2N1 DWYHDSLIWMUSOO-UHFFFAOYSA-N 0.000 title abstract description 17
- KLLLJCACIRKBDT-UHFFFAOYSA-N 2-phenyl-1H-indole Chemical class N1C2=CC=CC=C2C=C1C1=CC=CC=C1 KLLLJCACIRKBDT-UHFFFAOYSA-N 0.000 title abstract description 13
- 238000004519 manufacturing process Methods 0.000 title description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 38
- 239000001257 hydrogen Substances 0.000 claims abstract description 38
- 239000003814 drug Substances 0.000 claims abstract description 16
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 10
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 53
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 35
- 238000011282 treatment Methods 0.000 claims description 25
- JJDMKDXGNVJWCD-UHFFFAOYSA-N 1h-benzimidazole-4-carboxamide Chemical compound NC(=O)C1=CC=CC2=C1N=CN2 JJDMKDXGNVJWCD-UHFFFAOYSA-N 0.000 claims description 24
- 229910052757 nitrogen Inorganic materials 0.000 claims description 24
- 238000002360 preparation method Methods 0.000 claims description 24
- -1 chloro, fluoro, bromo, iodo Chemical group 0.000 claims description 19
- 150000002431 hydrogen Chemical class 0.000 claims description 18
- 229920000776 Poly(Adenosine diphosphate-ribose) polymerase Polymers 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 8
- 230000006378 damage Effects 0.000 claims description 8
- 201000010099 disease Diseases 0.000 claims description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
- 206010010904 Convulsion Diseases 0.000 claims description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- 230000000694 effects Effects 0.000 claims description 6
- 208000028867 ischemia Diseases 0.000 claims description 6
- 206010028980 Neoplasm Diseases 0.000 claims description 5
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 5
- 238000011321 prophylaxis Methods 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- 210000001367 artery Anatomy 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
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- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 238000002054 transplantation Methods 0.000 claims description 4
- 229910005965 SO 2 Inorganic materials 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
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- 239000000651 prodrug Substances 0.000 claims description 3
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- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- FDSYTWVNUJTPMA-UHFFFAOYSA-N 2-[3,9-bis(carboxymethyl)-3,6,9,15-tetrazabicyclo[9.3.1]pentadeca-1(15),11,13-trien-6-yl]acetic acid Chemical compound C1N(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC2=CC=CC1=N2 FDSYTWVNUJTPMA-UHFFFAOYSA-N 0.000 claims description 2
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- 208000037892 acute myocardial injury Diseases 0.000 claims description 2
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
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- 206010012601 diabetes mellitus Diseases 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
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- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
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- 102000012338 Poly(ADP-ribose) Polymerases Human genes 0.000 abstract description 34
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- 239000003112 inhibitor Substances 0.000 abstract description 15
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract description 3
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- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract description 3
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- 239000011737 fluorine Substances 0.000 abstract description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
- OBBJGEVEIULNEO-UHFFFAOYSA-N 2-phenyl-1h-benzimidazole-4-carboxamide Chemical compound N=1C=2C(C(=O)N)=CC=CC=2NC=1C1=CC=CC=C1 OBBJGEVEIULNEO-UHFFFAOYSA-N 0.000 description 22
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- 239000000243 solution Substances 0.000 description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
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- 229940121906 Poly ADP ribose polymerase inhibitor Drugs 0.000 description 14
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- 239000000047 product Substances 0.000 description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
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- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 5
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- FWBHETKCLVMNFS-UHFFFAOYSA-N 4',6-Diamino-2-phenylindol Chemical compound C1=CC(C(=N)N)=CC=C1C1=CC2=CC=C(C(N)=N)C=C2N1 FWBHETKCLVMNFS-UHFFFAOYSA-N 0.000 description 4
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- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 3
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Classifications
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Landscapes
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- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Epidemiology (AREA)
- Diabetes (AREA)
- Immunology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Heart & Thoracic Surgery (AREA)
- Hematology (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Psychology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Emergency Medicine (AREA)
- Psychiatry (AREA)
- Endocrinology (AREA)
- Obesity (AREA)
- Hospice & Palliative Care (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19852816 | 1998-11-17 | ||
| PCT/EP1999/008466 WO2000029384A1 (fr) | 1998-11-17 | 1999-11-05 | 2-phenylbenzimidazoles et 2-phenylindoles, leur production et leur utilisation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK6742001A3 true SK6742001A3 (en) | 2001-12-03 |
Family
ID=7887971
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK674-2001A SK6742001A3 (en) | 1998-11-17 | 1999-11-05 | 2-phenylbenzimidazoles and 2-phenylindoles, and production and use thereof |
Country Status (30)
| Country | Link |
|---|---|
| US (1) | US6509365B1 (fr) |
| EP (1) | EP1131301B1 (fr) |
| JP (2) | JP2002529537A (fr) |
| KR (1) | KR20010080474A (fr) |
| CN (1) | CN1331683A (fr) |
| AR (1) | AR021297A1 (fr) |
| AT (1) | ATE302758T1 (fr) |
| AU (1) | AU755694B2 (fr) |
| BG (1) | BG105550A (fr) |
| BR (1) | BR9915381A (fr) |
| CA (1) | CA2350734C (fr) |
| CO (1) | CO5140115A1 (fr) |
| CZ (1) | CZ20011724A3 (fr) |
| DE (1) | DE59912473D1 (fr) |
| DK (1) | DK1131301T3 (fr) |
| ES (1) | ES2247867T3 (fr) |
| HK (1) | HK1041694A1 (fr) |
| HR (1) | HRP20010451A2 (fr) |
| HU (1) | HUP0104129A3 (fr) |
| ID (1) | ID28846A (fr) |
| IL (1) | IL143102A0 (fr) |
| NO (1) | NO20012419L (fr) |
| PL (1) | PL347684A1 (fr) |
| RU (1) | RU2001116581A (fr) |
| SI (1) | SI1131301T1 (fr) |
| SK (1) | SK6742001A3 (fr) |
| TR (1) | TR200101400T2 (fr) |
| TW (1) | TW460466B (fr) |
| WO (1) | WO2000029384A1 (fr) |
| ZA (1) | ZA200103834B (fr) |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6911462B2 (en) * | 1998-05-22 | 2005-06-28 | Avanir Pharmaceuticals | Benzimidazole compounds for regulating IgE |
| US6919366B2 (en) * | 1998-05-22 | 2005-07-19 | Avanir Pharmaceuticals | Benzimidazole derivatives as modulators of IgE |
| TR200200972T2 (tr) | 1998-11-03 | 2002-07-22 | Basf Aktiengesellschaft | İkameli 2-fenilbenzimidazoller, üretimleri ve kullanımları |
| DE19920936A1 (de) * | 1999-05-07 | 2000-11-09 | Basf Ag | Heterozyklisch substituierte Benzimidazole, deren Herstellung und Anwendung |
| US6759425B2 (en) | 1999-10-21 | 2004-07-06 | Avanir Pharmaceuticals | Benzimidazole compounds for modulating IgE and inhibiting cellular proliferation |
| DE10022925A1 (de) * | 2000-05-11 | 2001-11-15 | Basf Ag | Substituierte Indole als PARP-Inhibitoren |
| CA2441177A1 (fr) * | 2001-03-12 | 2002-09-19 | Avanir Pharmaceuticals | Composes de benzimidazole modulateurs de l'ige et inhibiteurs de la proliferation cellulaire |
| TW200304820A (en) * | 2002-03-25 | 2003-10-16 | Avanir Pharmaceuticals | Use of benzimidazole analogs in the treatment of cell proliferation |
| US7786344B2 (en) | 2002-07-26 | 2010-08-31 | Basf Plant Science Gmbh | Selection method |
| WO2004024655A2 (en) | 2002-09-12 | 2004-03-25 | Avanir Pharmaceuticals | Phenyl-indole compounds for modulating ige and inhibiting cellular proliferation |
| TWI276631B (en) | 2002-09-12 | 2007-03-21 | Avanir Pharmaceuticals | Phenyl-aza-benzimidazole compounds for modulating IgE and inhibiting cellular proliferation |
| WO2004065370A1 (fr) * | 2003-01-23 | 2004-08-05 | Crystalgenomics, Inc. | Inhibiteur de glycogene synthase kinase 3$g(b), composition et procede de preparation associe |
| JP2007501618A (ja) * | 2003-08-08 | 2007-02-01 | アバニール・ファーマシューティカルズ | タンパク質輸送の選択的薬理学的阻害、および関連した、ヒト疾患を治療する方法 |
| US7781478B2 (en) | 2004-07-14 | 2010-08-24 | Ptc Therapeutics, Inc. | Methods for treating hepatitis C |
| CN100431606C (zh) * | 2004-11-22 | 2008-11-12 | 山东蓝金生物工程有限公司 | 一种抗癌药物组合物 |
| EP2045327B8 (fr) | 2005-03-08 | 2012-03-14 | BASF Plant Science GmbH | Expression à amélioration de séquences d'intron |
| WO2006110683A1 (fr) * | 2005-04-11 | 2006-10-19 | Abbott Laboratories | 1h-benzimidazole-4-carboxamides 2-substitues en tant qu'inhibiteurs de parp |
| TWI375673B (en) * | 2005-04-11 | 2012-11-01 | Abbott Lab | 1h-benzimidazole-4-carboxamides substituted with a quaternary carbon at the 2-position are potent parp inhibitors |
| ATE536349T1 (de) * | 2005-09-29 | 2011-12-15 | Abbott Lab | In der 2-stellung durch phenyl substituierte 1h- benzimidazol-4-carbonsäureamide sind wirksame parp-inhibitoren |
| CN101309908A (zh) | 2005-11-15 | 2008-11-19 | 艾博特公司 | 作为有效parp抑制剂的取代的1h-苯并咪唑-4-甲酰胺化合物 |
| US20090275619A1 (en) * | 2006-04-03 | 2009-11-05 | BOUERES Julia | Amide Substituted Indazole and Benzotriazole Derivatives as Poly(ADP-Ribose)Polymerase (PARP) Inhibitors |
| ES2385849T3 (es) * | 2006-05-02 | 2012-08-01 | Abbott Laboratories | Las 1H-bencimidazol-4-carboxamidas substituidas son potentes inhibidores de la PARP |
| PL2336120T3 (pl) | 2007-01-10 | 2014-12-31 | Msd Italia Srl | Kombinacje zawierające indazole podstawione grupą amidową jako inhibitory polimerazy poli(ADP-rybozy) (PARP) |
| US8067613B2 (en) | 2007-07-16 | 2011-11-29 | Abbott Laboratories | Benzimidazole poly(ADP ribose)polymerase inhibitors |
| US7816540B2 (en) * | 2007-12-21 | 2010-10-19 | Hoffmann-La Roche Inc. | Carboxyl- or hydroxyl-substituted benzimidazole derivatives |
| RU2495035C2 (ru) | 2008-01-08 | 2013-10-10 | Мерк Шарп Энд Домэ Лтд | Фармацевтически приемлемые соли 2-{4-[(3s)-пиперидин-3-ил]фенил}-2н-индазол-7-карбоксамида |
| WO2010083199A1 (fr) * | 2009-01-19 | 2010-07-22 | Abbott Laboratories | Inhibiteurs benzthiazole de la poly(adp-ribose)polymérase |
| US10316304B2 (en) | 2009-11-27 | 2019-06-11 | Basf Plant Science Company Gmbh | Chimeric endonucleases and uses thereof |
| JP5944320B2 (ja) | 2009-11-27 | 2016-07-05 | ビーエーエスエフ プラント サイエンス カンパニー ゲーエムベーハー | 最適化エンドヌクレアーゼおよびその使用 |
| AU2010325564A1 (en) | 2009-11-27 | 2012-07-12 | Basf Plant Science Company Gmbh | Chimeric endonucleases and uses thereof |
| WO2011107504A1 (fr) | 2010-03-04 | 2011-09-09 | Bayer Cropscience Ag | 2-amidobenzimidazoles substitués par fluoroalkyle et leur utilisation pour augmenter la tolérance au stress chez les végétaux |
| EP2561759A1 (fr) | 2011-08-26 | 2013-02-27 | Bayer Cropscience AG | 2-amidobenzimidazoles fluoroalkyl substitués et leur effet sur la croissance des plantes |
| CN103242273B (zh) * | 2012-02-09 | 2015-06-03 | 中国科学院上海药物研究所 | 2-芳基苯并呋喃-7-甲酰胺类化合物、其制备方法及用途 |
| CN102627620B (zh) * | 2012-04-10 | 2015-12-16 | 江苏先声药物研究有限公司 | 一类苯并呋喃衍生物及其医药应用 |
| CN104780764A (zh) * | 2012-09-05 | 2015-07-15 | 拜尔农作物科学股份公司 | 取代的2-酰氨基苯并咪唑、2-酰氨基苯并噁唑和2-酰氨基苯并噻唑或其盐作为活性物质对抗非生物植物胁迫的用途 |
| CN104230896A (zh) * | 2013-06-17 | 2014-12-24 | 上海汇伦生命科技有限公司 | 苯并咪唑-2-哌嗪杂环类化合物、其药物组合物及其制备方法和用途 |
| US10722484B2 (en) | 2016-03-09 | 2020-07-28 | K-Gen, Inc. | Methods of cancer treatment |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3522230A1 (de) * | 1985-06-21 | 1987-01-02 | Thomae Gmbh Dr K | Neue 2-arylimidazole, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
| DE4304455A1 (de) * | 1993-02-15 | 1994-08-18 | Bayer Ag | Heterocyclisch substituierte Phenyl-cyclohexan-carbonsäurederivate |
| AU714873B2 (en) * | 1995-08-02 | 2000-01-13 | Newcastle University Ventures Limited | Benzimidazole compounds |
| WO1998006703A1 (fr) * | 1996-08-14 | 1998-02-19 | Warner-Lambert Company | Derives 2-phenyle benzimidazole en tant qu'antagonistes de mcp-1 |
-
1999
- 1999-11-05 HU HU0104129A patent/HUP0104129A3/hu unknown
- 1999-11-05 ID IDW00200101197A patent/ID28846A/id unknown
- 1999-11-05 CA CA002350734A patent/CA2350734C/fr not_active Expired - Fee Related
- 1999-11-05 JP JP2000582371A patent/JP2002529537A/ja active Pending
- 1999-11-05 DE DE59912473T patent/DE59912473D1/de not_active Expired - Lifetime
- 1999-11-05 ES ES99972206T patent/ES2247867T3/es not_active Expired - Lifetime
- 1999-11-05 IL IL14310299A patent/IL143102A0/xx unknown
- 1999-11-05 SK SK674-2001A patent/SK6742001A3/sk unknown
- 1999-11-05 BR BR9915381-5A patent/BR9915381A/pt not_active IP Right Cessation
- 1999-11-05 DK DK99972206T patent/DK1131301T3/da active
- 1999-11-05 CN CN99814810A patent/CN1331683A/zh active Pending
- 1999-11-05 TR TR2001/01400T patent/TR200101400T2/xx unknown
- 1999-11-05 KR KR1020017006235A patent/KR20010080474A/ko not_active Application Discontinuation
- 1999-11-05 AU AU13798/00A patent/AU755694B2/en not_active Ceased
- 1999-11-05 US US09/856,036 patent/US6509365B1/en not_active Expired - Lifetime
- 1999-11-05 EP EP99972206A patent/EP1131301B1/fr not_active Expired - Lifetime
- 1999-11-05 AT AT99972206T patent/ATE302758T1/de not_active IP Right Cessation
- 1999-11-05 WO PCT/EP1999/008466 patent/WO2000029384A1/fr not_active Application Discontinuation
- 1999-11-05 CZ CZ20011724A patent/CZ20011724A3/cs unknown
- 1999-11-05 PL PL99347684A patent/PL347684A1/xx not_active Application Discontinuation
- 1999-11-05 RU RU2001116581/04A patent/RU2001116581A/ru unknown
- 1999-11-05 SI SI9930835T patent/SI1131301T1/sl unknown
- 1999-11-17 AR ARP990105835A patent/AR021297A1/es unknown
- 1999-11-17 CO CO99072377A patent/CO5140115A1/es unknown
- 1999-11-17 TW TW088120025A patent/TW460466B/zh not_active IP Right Cessation
-
2001
- 2001-05-11 ZA ZA200103834A patent/ZA200103834B/en unknown
- 2001-05-16 NO NO20012419A patent/NO20012419L/no not_active Application Discontinuation
- 2001-05-30 BG BG105550A patent/BG105550A/xx unknown
- 2001-06-15 HR HR20010451A patent/HRP20010451A2/hr not_active Application Discontinuation
-
2002
- 2002-05-03 HK HK02103331.0A patent/HK1041694A1/zh unknown
-
2008
- 2008-11-06 JP JP2008285818A patent/JP2009120609A/ja active Pending
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