OA11590A - 2-Substituted-1-piperidyl benzimidazole compounds as ORL1-receptor agonists. - Google Patents
2-Substituted-1-piperidyl benzimidazole compounds as ORL1-receptor agonists. Download PDFInfo
- Publication number
- OA11590A OA11590A OA1200100031A OA1200100031A OA11590A OA 11590 A OA11590 A OA 11590A OA 1200100031 A OA1200100031 A OA 1200100031A OA 1200100031 A OA1200100031 A OA 1200100031A OA 11590 A OA11590 A OA 11590A
- Authority
- OA
- OAPI
- Prior art keywords
- alkyl
- halo
- group
- aromatic
- aryl
- Prior art date
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- -1 2-Substituted-1-piperidyl benzimidazole compounds Chemical class 0.000 title claims description 268
- 108010020615 nociceptin receptor Proteins 0.000 title claims description 7
- 239000000018 receptor agonist Substances 0.000 title description 3
- 229940044601 receptor agonist Drugs 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 170
- 125000003118 aryl group Chemical group 0.000 claims abstract description 152
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 62
- 239000001257 hydrogen Substances 0.000 claims abstract description 62
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims abstract description 61
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 44
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 43
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 43
- 125000001475 halogen functional group Chemical group 0.000 claims abstract description 31
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims abstract description 22
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 22
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 18
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 15
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 187
- 125000005843 halogen group Chemical group 0.000 claims description 144
- 238000000034 method Methods 0.000 claims description 126
- 150000001412 amines Chemical class 0.000 claims description 89
- 125000003545 alkoxy group Chemical group 0.000 claims description 49
- 125000001424 substituent group Chemical group 0.000 claims description 49
- 238000006243 chemical reaction Methods 0.000 claims description 48
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 47
- 239000011541 reaction mixture Substances 0.000 claims description 46
- 229910052799 carbon Inorganic materials 0.000 claims description 43
- 125000004432 carbon atom Chemical group C* 0.000 claims description 40
- 125000003386 piperidinyl group Chemical group 0.000 claims description 40
- 229910052757 nitrogen Inorganic materials 0.000 claims description 39
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- 125000006413 ring segment Chemical group 0.000 claims description 37
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 27
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 27
- 125000005842 heteroatom Chemical group 0.000 claims description 24
- 125000001624 naphthyl group Chemical group 0.000 claims description 24
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 15
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- 125000004076 pyridyl group Chemical group 0.000 claims description 13
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 125000006730 (C2-C5) alkynyl group Chemical group 0.000 claims description 11
- 230000008878 coupling Effects 0.000 claims description 11
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- 125000002541 furyl group Chemical group 0.000 claims description 11
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 11
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 10
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims description 10
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 10
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 10
- 125000004193 piperazinyl group Chemical group 0.000 claims description 10
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 9
- 125000002883 imidazolyl group Chemical group 0.000 claims description 9
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 9
- 125000005936 piperidyl group Chemical group 0.000 claims description 9
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- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
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- 125000003831 tetrazolyl group Chemical group 0.000 claims description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 7
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 7
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
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- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
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- 238000006748 scratching Methods 0.000 description 1
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
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- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
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- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
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- AHOGNWMJZLUEQS-UHFFFAOYSA-N tert-butyl n-(azetidin-2-yl)carbamate Chemical compound CC(C)(C)OC(=O)NC1CCN1 AHOGNWMJZLUEQS-UHFFFAOYSA-N 0.000 description 1
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- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
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- 238000003354 tissue distribution assay Methods 0.000 description 1
- 229960005196 titanium dioxide Drugs 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
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- 239000004474 valine Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- A—HUMAN NECESSITIES
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
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- A61P3/12—Drugs for disorders of the metabolism for electrolyte homeostasis
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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
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- Animal Behavior & Ethology (AREA)
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- Cardiology (AREA)
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- Diabetes (AREA)
- Hematology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Addiction (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
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| IBPCT/IB98/01206 | 1998-08-06 |
Publications (1)
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| OA11590A true OA11590A (en) | 2004-08-18 |
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| OA1200100031A OA11590A (en) | 1998-08-06 | 1999-07-05 | 2-Substituted-1-piperidyl benzimidazole compounds as ORL1-receptor agonists. |
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| US6340681B1 (en) * | 1999-07-16 | 2002-01-22 | Pfizer Inc | 2-benzimidazolylamine compounds as ORL-1-receptor agonists |
| SE9902987D0 (sv) | 1999-08-24 | 1999-08-24 | Astra Pharma Prod | Novel compounds |
| SE9903544D0 (sv) | 1999-10-01 | 1999-10-01 | Astra Pharma Prod | Novel compounds |
| ATE306488T1 (de) | 2000-01-05 | 2005-10-15 | Pfizer | Benzimidazol-verbindungen zur verwendung als orl1-rezeptor-antagonisten |
| GB2359078A (en) * | 2000-02-11 | 2001-08-15 | Astrazeneca Uk Ltd | Pharmaceutically active pyrimidine derivatives |
| GB2359081A (en) | 2000-02-11 | 2001-08-15 | Astrazeneca Uk Ltd | Pharmaceutically active thiazolopyrimidines |
| GB2359551A (en) | 2000-02-23 | 2001-08-29 | Astrazeneca Uk Ltd | Pharmaceutically active pyrimidine derivatives |
| GB0005642D0 (en) | 2000-03-10 | 2000-05-03 | Astrazeneca Uk Ltd | Chemical compounds |
| SE0003828D0 (sv) | 2000-10-20 | 2000-10-20 | Astrazeneca Ab | Novel compounds |
| WO2002040019A1 (fr) | 2000-11-15 | 2002-05-23 | Banyu Pharmaceutical Co.,Ltd. | Derives benzimidazoles |
| GB0104050D0 (en) | 2001-02-19 | 2001-04-04 | Astrazeneca Ab | Chemical compounds |
| GB0107228D0 (en) | 2001-03-22 | 2001-05-16 | Astrazeneca Ab | Chemical compounds |
| SE0101322D0 (sv) | 2001-04-12 | 2001-04-12 | Astrazeneca Ab | Novel compounds |
| WO2002085361A1 (fr) * | 2001-04-18 | 2002-10-31 | Euro-Celtique, S.A. | Composes de benzimidazolone |
| AU2002303406B2 (en) | 2001-04-18 | 2006-03-30 | Euro-Celtique S.A. | Nociceptin analogs |
| IL158485A0 (en) | 2001-04-18 | 2004-05-12 | Euro Celtique Sa | Spiropyrazole compounds |
| IL158484A0 (en) * | 2001-04-18 | 2004-05-12 | Euro Celtique Sa | Nociceptin analogs |
| US6828440B2 (en) | 2001-04-18 | 2004-12-07 | Euro-Celtique, S.A. | Spiroindene and spiroindane compounds |
| EP1406629A1 (fr) * | 2001-07-02 | 2004-04-14 | Omeros Corporation | Procede visant a induire une analgesie, qui comprend l'administration alternee d'un agoniste de recepteur d'opioides et d'un agoniste de recepteur 1 du type recepteur d'opioides, et pompe a perfusion implantable |
| US20030040479A1 (en) * | 2001-07-02 | 2003-02-27 | Omeros Corporation | Rotational intrathecal analgesia method and device |
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| SE0103818D0 (sv) * | 2001-11-15 | 2001-11-15 | Astrazeneca Ab | Chemical compounds |
| AU2002360561A1 (en) * | 2001-12-11 | 2003-06-23 | Sepracor, Inc. | 4-substituted piperidines, and methods of use thereof |
| DK1491212T3 (da) | 2002-03-29 | 2012-10-29 | Mitsubishi Tanabe Pharma Corp | Middel til behandling af søvnforstyrrelser |
| GB0221828D0 (en) | 2002-09-20 | 2002-10-30 | Astrazeneca Ab | Novel compound |
| GB0221829D0 (en) * | 2002-09-20 | 2002-10-30 | Astrazeneca Ab | Novel compound |
| DE10252666A1 (de) * | 2002-11-11 | 2004-08-05 | Grünenthal GmbH | N-Piperidyl-cyclohexan-Derivate |
| DE10252665A1 (de) * | 2002-11-11 | 2004-06-03 | Grünenthal GmbH | 4-Aminomethyl-1-aryl-cyclohexylamin-Derivate |
| SE0301369D0 (sv) | 2003-05-09 | 2003-05-09 | Astrazeneca Ab | Chemical compounds |
| GB0315203D0 (en) * | 2003-06-28 | 2003-08-06 | Celltech R&D Ltd | Chemical compounds |
| US8067603B2 (en) | 2003-09-25 | 2011-11-29 | Solvay Pharmaceuticals B.V. | Benzimidazolone and quinazolinone derivatives as agonists on human ORL1 receptors |
| GB0328243D0 (en) * | 2003-12-05 | 2004-01-07 | Astrazeneca Ab | Methods |
| WO2005060947A2 (fr) * | 2003-12-19 | 2005-07-07 | Sri International | Ligands agonistes et antagonistes du recepteur de la nociceptine |
| EP1810677A1 (fr) * | 2004-10-08 | 2007-07-25 | Takeda Pharmaceutical Company Limited | Agent de régulation du fonctionnement d'un récepteur |
| WO2006074991A1 (fr) | 2005-01-11 | 2006-07-20 | Neurosearch A/S | Nouveaux derives de 2-amino benzimidazole et leur utilisation en tant que modulateurs des canaux a potassium actives par le calcium a faible conductance |
| JP2009541454A (ja) * | 2006-07-03 | 2009-11-26 | ノイロサーチ アクティーゼルスカブ | モノアミン再摂取阻害剤及びカリウムチャネル活性剤の併用 |
| JP5462633B2 (ja) | 2007-01-16 | 2014-04-02 | パーデュー、ファーマ、リミテッド、パートナーシップ | 複素環置換ピペリジン化合物とその使用 |
| JP5554709B2 (ja) * | 2007-08-31 | 2014-07-23 | パーデュー、ファーマ、リミテッド、パートナーシップ | 置換キノキサリンタイプピペリジン化合物とその使用 |
| US8119661B2 (en) * | 2007-09-11 | 2012-02-21 | Astrazeneca Ab | Piperidine derivatives and their use as muscarinic receptor modulators |
| ES2393849T7 (es) | 2008-07-21 | 2015-01-28 | Purdue Pharma Lp | Compuestos de piperidina puenteada, de tipo quinoxalina sustituida, y usos de los mismos |
| KR20130108543A (ko) | 2010-08-05 | 2013-10-04 | 암젠 인코포레이션 | 역형성 림프종 키나제를 억제하는 벤즈이미다졸 및 아자벤즈이미다졸 화합물 |
| BR112014016548A8 (pt) | 2012-01-06 | 2017-07-04 | Board Of Regents Of The Univ Of Oklahoma | tensoativos baseados em sulfóxido |
| HRP20181671T1 (hr) | 2012-02-09 | 2018-12-14 | Novus International, Inc. | Heteroatom koji sadrži cikličke dimere |
| JO3300B1 (ar) | 2012-06-06 | 2018-09-16 | Novartis Ag | مركبات وتركيبات لتعديل نشاط egfr |
| CN107753462B (zh) | 2012-07-12 | 2021-01-08 | 诺华丝国际股份有限公司 | 用于保护生物活性剂的基质和层组合物 |
| US9085561B2 (en) * | 2012-07-30 | 2015-07-21 | Purdue Pharma L.P. | Cyclic urea- or lactam-substituted quinoxaline-type piperidines as ORL-1 modulators |
| WO2014102594A2 (fr) * | 2012-12-27 | 2014-07-03 | Purdue Pharma L.P. | Composés de pipéridine de type benzimidazole substitué et leurs utilisations |
| EP2976077A4 (fr) | 2013-03-22 | 2016-11-30 | Scripps Research Inst | Benzimidazoles substitués en tant que modulateurs d'un récepteur de nociceptine |
| EP3119762B9 (fr) | 2014-03-20 | 2021-10-20 | Capella Therapeutics, Inc. | Dérivés de benzimidazole en tant qu'inhibiteurs de la tyrosine kinase erbb pour le traitement du cancer |
| US10227551B2 (en) | 2015-11-12 | 2019-03-12 | Novus International, Inc. | Sulfur-containing compounds as solvents |
| US10584306B2 (en) | 2017-08-11 | 2020-03-10 | Board Of Regents Of The University Of Oklahoma | Surfactant microemulsions |
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| US3318900A (en) * | 1964-05-06 | 1967-05-09 | Janssen Pharmaceutica Nv | Derivatives of benzimidazolinyl piperidine |
| JPS5297978A (en) * | 1976-06-02 | 1977-08-17 | Yoshitomi Pharmaceut Ind Ltd | Preparation of alicyclic derivatives |
| US5821219A (en) | 1995-08-11 | 1998-10-13 | Oregon Health Sciences University | Opioid antagonists and methods of their use |
| CA2229202C (fr) | 1995-08-15 | 2008-05-20 | Universite Libre De Bruxells | Methodes pour l'identification d'antagonistes ou d'agonistes du recepteur orl-1 humain |
| US5866346A (en) | 1995-09-27 | 1999-02-02 | Indiana Unversity Foundation | Methods of using dynorphins as ligands for XOR1 receptor |
| US6180649B1 (en) * | 1996-04-19 | 2001-01-30 | Nerosearch A/S | 1-(4-piperidyl)-benzimidazoles having neurotrophic activity |
| EP0813065A3 (fr) | 1996-06-13 | 1998-07-22 | F. Hoffmann-La Roche Ag | Modulation de la fonction d'un récepteur LC-132(analogue à opioide) |
| EP0829481A1 (fr) * | 1996-09-16 | 1998-03-18 | Pfizer Inc. | Dérivés de l'acide morphinane hydroxamique |
| US5718912A (en) * | 1996-10-28 | 1998-02-17 | Merck & Co., Inc. | Muscarine agonists |
| AU732329B2 (en) | 1997-05-30 | 2001-04-12 | Banyu Pharmaceutical Co., Ltd. | 2-oxoimidazole derivative |
| AU8334298A (en) | 1997-07-15 | 1999-02-10 | Novo Nordisk A/S | Nociceptin analogues |
| US5929035A (en) | 1998-04-14 | 1999-07-27 | Regents Of The University Of Michigan | Methods of treating intestinal disorders |
| ID29137A (id) | 1998-07-27 | 2001-08-02 | Schering Corp | Ligan-ligan afinitas tinggi untuk reseptor nosiseptin orl-1 |
-
1999
- 1999-06-25 MA MA25646A patent/MA26659A1/fr unknown
- 1999-06-28 TW TW088110899A patent/TW513424B/zh not_active IP Right Cessation
- 1999-07-05 SI SI9930151T patent/SI1102762T1/xx unknown
- 1999-07-05 CA CA002339621A patent/CA2339621C/fr not_active Expired - Fee Related
- 1999-07-05 HK HK02101444.8A patent/HK1040188A1/zh unknown
- 1999-07-05 HN HN1999000105A patent/HN1999000105A/es unknown
- 1999-07-05 EP EP99926688A patent/EP1102762B1/fr not_active Expired - Lifetime
- 1999-07-05 ID IDW20010284D patent/ID27212A/id unknown
- 1999-07-05 IL IL14102999A patent/IL141029A0/xx unknown
- 1999-07-05 DE DE69903953T patent/DE69903953T2/de not_active Expired - Fee Related
- 1999-07-05 AU AU43859/99A patent/AU749166B2/en not_active Ceased
- 1999-07-05 CN CN99810857A patent/CN1317968A/zh active Pending
- 1999-07-05 JP JP2000563646A patent/JP3367945B2/ja not_active Expired - Fee Related
- 1999-07-05 SK SK160-2001A patent/SK1602001A3/sk unknown
- 1999-07-05 HU HU0103567A patent/HUP0103567A3/hu unknown
- 1999-07-05 BR BR9912778-4A patent/BR9912778A/pt not_active Application Discontinuation
- 1999-07-05 GE GEAP19995740A patent/GEP20033000B/en unknown
- 1999-07-05 HR HR970081A patent/HRP20010089B1/xx not_active IP Right Cessation
- 1999-07-05 ES ES99926688T patent/ES2185357T3/es not_active Expired - Lifetime
- 1999-07-05 AP APAP/P/2001/002063A patent/AP2001002063A0/en unknown
- 1999-07-05 DK DK99926688T patent/DK1102762T3/da active
- 1999-07-05 WO PCT/IB1999/001239 patent/WO2000008013A2/fr not_active Ceased
- 1999-07-05 TR TR2001/00403T patent/TR200100403T2/xx unknown
- 1999-07-05 PL PL99346211A patent/PL346211A1/xx not_active Application Discontinuation
- 1999-07-05 EA EA200100104A patent/EA200100104A1/ru unknown
- 1999-07-05 OA OA1200100031A patent/OA11590A/en unknown
- 1999-07-05 CZ CZ2001397A patent/CZ2001397A3/cs unknown
- 1999-07-05 TN TNTNSN99142A patent/TNSN99142A1/fr unknown
- 1999-07-05 YU YU8201A patent/YU8201A/sh unknown
- 1999-07-05 NZ NZ509299A patent/NZ509299A/en not_active Application Discontinuation
- 1999-07-05 PT PT99926688T patent/PT1102762E/pt unknown
- 1999-07-05 AT AT99926688T patent/ATE227716T1/de not_active IP Right Cessation
- 1999-07-05 EE EEP200100075A patent/EE200100075A/xx unknown
- 1999-07-06 AR ARP990103264A patent/AR018686A1/es active IP Right Grant
- 1999-07-15 PE PE1999000717A patent/PE20000868A1/es not_active Application Discontinuation
- 1999-07-16 PA PA19998477701A patent/PA8477701A1/es unknown
- 1999-07-16 SV SV1999000099A patent/SV1999000099A/es not_active Application Discontinuation
- 1999-08-05 US US09/369,208 patent/US6172067B1/en not_active Expired - Fee Related
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2001
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- 2001-02-05 NO NO20010603A patent/NO20010603L/no not_active Application Discontinuation
- 2001-03-01 BG BG105301A patent/BG105301A/xx unknown
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