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
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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
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- 235000019812 sodium carboxymethyl cellulose Nutrition 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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- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
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- 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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- 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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- A61P25/00—Drugs for disorders of the nervous system
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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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- 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)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
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- Animal Behavior & Ethology (AREA)
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- Engineering & Computer Science (AREA)
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- Pain & Pain Management (AREA)
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- Hospice & Palliative Care (AREA)
- Heart & Thoracic Surgery (AREA)
- Addiction (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (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 |
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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 |
| ES2249237T3 (es) * | 2000-01-05 | 2006-04-01 | Pfizer Inc. | Compuestos de bencimidazol como antagonistas del receptor orl1. |
| 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 |
| US6969712B2 (en) | 2000-11-15 | 2005-11-29 | Banyu Pharmaceutical Co., Ltd. | Benzimidazole derivatives |
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| GB0107228D0 (en) | 2001-03-22 | 2001-05-16 | Astrazeneca Ab | Chemical compounds |
| SE0101322D0 (sv) | 2001-04-12 | 2001-04-12 | Astrazeneca Ab | Novel compounds |
| ATE410165T1 (de) | 2001-04-18 | 2008-10-15 | Euro Celtique Sa | Nociceptin-analoga |
| EP2033644A1 (fr) | 2001-04-18 | 2009-03-11 | Euro-Celtique S.A. | Composés spiro-indene et spiro-indane |
| ATE403431T1 (de) * | 2001-04-18 | 2008-08-15 | Euro Celtique Sa | Benzimidazolon-verbindungen |
| RU2268883C2 (ru) * | 2001-04-18 | 2006-01-27 | Эро-Селтик, С.А. | Аналоги ноницептина и фармацевтическая композиция на их основе |
| CN1516584A (zh) | 2001-04-18 | 2004-07-28 | ŷ�����ǹɷ�����˾ | 螺吡唑化合物 |
| US20030040479A1 (en) * | 2001-07-02 | 2003-02-27 | Omeros Corporation | Rotational intrathecal analgesia method and device |
| WO2003004034A1 (fr) * | 2001-07-02 | 2003-01-16 | 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 |
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| SE0103818D0 (sv) | 2001-11-15 | 2001-11-15 | Astrazeneca Ab | Chemical compounds |
| US7812035B2 (en) * | 2001-12-11 | 2010-10-12 | Sepracor Inc. | 4-substituted piperidines, and methods of use thereof |
| US7566728B2 (en) | 2002-03-29 | 2009-07-28 | Mitsubishi Tanabe Pharma Corporation | Remedy for sleep disturbance |
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| GB0221828D0 (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 |
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| GB0315203D0 (en) * | 2003-06-28 | 2003-08-06 | Celltech R&D Ltd | Chemical compounds |
| SA04250305B1 (ar) | 2003-09-25 | 2008-06-02 | سولفاي فارماسوتيكالز بي . في | مشتقات بنزيميدازولون cenzimidazolone وكينازولينون quinazolinone كمساعادات على مستقبلات ORL1 البشرية |
| 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 |
| JPWO2006038738A1 (ja) * | 2004-10-08 | 2008-05-15 | 武田薬品工業株式会社 | 受容体機能調節剤 |
| EP2319512A1 (fr) | 2005-01-11 | 2011-05-11 | NeuroSearch AS | Dérivés de 2-amino benzimidazole et leur utilisation comme modulateurs des canaux potassiques calcium-dépendants de 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 |
| EP2397477B1 (fr) | 2007-01-16 | 2014-03-05 | Purdue Pharma LP | Composés de pipéridine hétérocycliques substitués et leurs utilisations |
| WO2009027820A2 (fr) | 2007-08-31 | 2009-03-05 | Purdue Pharma L.P. | Composés de pipéridine de type quinoxaline substituée et leurs utilisations |
| US8119661B2 (en) * | 2007-09-11 | 2012-02-21 | Astrazeneca Ab | Piperidine derivatives and their use as muscarinic receptor modulators |
| RS52590B2 (sr) | 2008-07-21 | 2018-05-31 | Purdue Pharma Lp | Jedinjenja tipa supstituisanog hinoksalina sa premošćenim piperidinom i njihova upotreba |
| SG10201505997TA (en) | 2010-08-05 | 2015-09-29 | Amgen Inc | Benzimidazole And Azabenzimidazole Compounds That Inhibit Anaplastic Lymphoma Kinase |
| MX346043B (es) | 2012-01-06 | 2017-03-03 | Novus Int Inc | Tensioactivos basados en sulfoxido. |
| 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 |
| PL2871973T3 (pl) | 2012-07-12 | 2019-02-28 | Novus International Inc. | Kompozycje matrycy i warstwy do ochrony środków bioaktywnych |
| US9085561B2 (en) * | 2012-07-30 | 2015-07-21 | Purdue Pharma L.P. | Cyclic urea- or lactam-substituted quinoxaline-type piperidines as ORL-1 modulators |
| US9090618B2 (en) | 2012-12-27 | 2015-07-28 | Purdue Pharma L.P. | Substituted benzimidazole-type piperidine compounds and uses thereof |
| EP2976077A4 (fr) | 2013-03-22 | 2016-11-30 | Scripps Research Inst | Benzimidazoles substitués en tant que modulateurs d'un récepteur de nociceptine |
| IL291000B2 (en) * | 2014-03-20 | 2024-04-01 | Capella Therapeutics Inc | Benzimidazole derivatives as erbb tyrosine kinase inhibitors for the treatment of cancer |
| CN112707851A (zh) | 2015-11-12 | 2021-04-27 | 诺华丝国际股份有限公司 | 作为溶剂的含硫化合物 |
| 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 |
| DE69736776T2 (de) * | 1996-04-19 | 2007-01-18 | Neurosearch A/S | 1-(4-piperidyl)-benzimidazole mit neurotropher aktivität |
| 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 |
| CA2291094C (fr) | 1997-05-30 | 2008-02-26 | Banyu Pharmaceutical Co., Ltd. | Derive de 2-0xoimidazole |
| WO1999003880A1 (fr) | 1997-07-15 | 1999-01-28 | Novo Nordisk A/S | Analogues de nociceptine |
| 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 |
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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 CZ CZ2001397A patent/CZ2001397A3/cs unknown
- 1999-07-05 HU HU0103567A patent/HUP0103567A3/hu unknown
- 1999-07-05 WO PCT/IB1999/001239 patent/WO2000008013A2/fr not_active Ceased
- 1999-07-05 TN TNTNSN99142A patent/TNSN99142A1/fr unknown
- 1999-07-05 JP JP2000563646A patent/JP3367945B2/ja not_active Expired - Fee Related
- 1999-07-05 AU AU43859/99A patent/AU749166B2/en not_active Ceased
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- 1999-07-05 HR HR970081A patent/HRP20010089B1/xx not_active IP Right Cessation
- 1999-07-05 AT AT99926688T patent/ATE227716T1/de not_active IP Right Cessation
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- 1999-07-05 ES ES99926688T patent/ES2185357T3/es not_active Expired - Lifetime
- 1999-07-05 EE EEP200100075A patent/EE200100075A/xx unknown
- 1999-07-05 EP EP99926688A patent/EP1102762B1/fr not_active Expired - Lifetime
- 1999-07-05 GE GEAP19995740A patent/GEP20033000B/en unknown
- 1999-07-05 TR TR2001/00403T patent/TR200100403T2/xx unknown
- 1999-07-05 BR BR9912778-4A patent/BR9912778A/pt not_active Application Discontinuation
- 1999-07-05 SK SK160-2001A patent/SK1602001A3/sk unknown
- 1999-07-05 CA CA002339621A patent/CA2339621C/fr not_active Expired - Fee Related
- 1999-07-05 DK DK99926688T patent/DK1102762T3/da active
- 1999-07-05 PL PL99346211A patent/PL346211A1/xx not_active Application Discontinuation
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- 1999-07-05 NZ NZ509299A patent/NZ509299A/en not_active Application Discontinuation
- 1999-07-05 DE DE69903953T patent/DE69903953T2/de not_active Expired - Fee Related
- 1999-07-05 HK HK02101444.8A patent/HK1040188A1/zh unknown
- 1999-07-05 EA EA200100104A patent/EA200100104A1/ru unknown
- 1999-07-05 SI SI9930151T patent/SI1102762T1/xx unknown
- 1999-07-05 PT PT99926688T patent/PT1102762E/pt unknown
- 1999-07-05 CN CN99810857A patent/CN1317968A/zh active Pending
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- 1999-08-05 US US09/369,208 patent/US6172067B1/en not_active Expired - Fee Related
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2001
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