NO312672B1 - Tri-substituerte fenylderivater anvendelige som PDE IV- inhibitorer, fremgangsmåte for fremstilling derav og farmasöytiskepreparater inneholdende dem - Google Patents
Tri-substituerte fenylderivater anvendelige som PDE IV- inhibitorer, fremgangsmåte for fremstilling derav og farmasöytiskepreparater inneholdende dem Download PDFInfo
- Publication number
- NO312672B1 NO312672B1 NO19965524A NO965524A NO312672B1 NO 312672 B1 NO312672 B1 NO 312672B1 NO 19965524 A NO19965524 A NO 19965524A NO 965524 A NO965524 A NO 965524A NO 312672 B1 NO312672 B1 NO 312672B1
- Authority
- NO
- Norway
- Prior art keywords
- pyridine
- group
- cyclopentyloxy
- methoxyphenyl
- ethyl
- Prior art date
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- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 title claims abstract description 8
- -1 Tri-substituted phenyl Chemical class 0.000 title abstract description 25
- 238000000034 method Methods 0.000 title abstract description 15
- 238000002360 preparation method Methods 0.000 title abstract description 15
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- 239000008194 pharmaceutical composition Substances 0.000 title 1
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 73
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 35
- 239000000203 mixture Substances 0.000 claims description 30
- 150000003839 salts Chemical class 0.000 claims description 19
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- 125000005843 halogen group Chemical group 0.000 claims description 8
- 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 claims description 7
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- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
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- 150000002739 metals Chemical class 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
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- HVOYZOQVDYHUPF-UHFFFAOYSA-N n,n',n'-trimethylethane-1,2-diamine Chemical compound CNCCN(C)C HVOYZOQVDYHUPF-UHFFFAOYSA-N 0.000 description 1
- QJKPGROOFFPTMM-YNMZEGNTSA-N n-[4-[4-[(1s)-1-(3-cyclopentyloxy-4-methoxyphenyl)-2-pyridin-4-ylethoxy]phenyl]phenyl]methanesulfonamide;hydrochloride Chemical compound Cl.COC1=CC=C([C@H](CC=2C=CN=CC=2)OC=2C=CC(=CC=2)C=2C=CC(NS(C)(=O)=O)=CC=2)C=C1OC1CCCC1 QJKPGROOFFPTMM-YNMZEGNTSA-N 0.000 description 1
- NUIVIVXBBBZCFA-UHFFFAOYSA-N n-[4-[4-[1-(3-cyclopentyloxy-4-methoxyphenyl)-2-pyridin-4-ylethoxy]phenyl]phenyl]methanesulfonamide Chemical compound COC1=CC=C(C(CC=2C=CN=CC=2)OC=2C=CC(=CC=2)C=2C=CC(NS(C)(=O)=O)=CC=2)C=C1OC1CCCC1 NUIVIVXBBBZCFA-UHFFFAOYSA-N 0.000 description 1
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- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
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- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridine hydrochloride Substances [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 1
- QJZUKDFHGGYHMC-UHFFFAOYSA-N pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1 QJZUKDFHGGYHMC-UHFFFAOYSA-N 0.000 description 1
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- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- GZKMGAXTHYGXEO-UHFFFAOYSA-M ruthenium(1+);triphenylphosphane;chloride Chemical compound [Ru]Cl.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 GZKMGAXTHYGXEO-UHFFFAOYSA-M 0.000 description 1
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- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 229940023144 sodium glycolate Drugs 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
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- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
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- 229910052623 talc Inorganic materials 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
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- 238000005809 transesterification reaction Methods 0.000 description 1
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- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 1
- JEJAMASKDTUEBZ-UHFFFAOYSA-N tris(1,1,3-tribromo-2,2-dimethylpropyl) phosphate Chemical compound BrCC(C)(C)C(Br)(Br)OP(=O)(OC(Br)(Br)C(C)(C)CBr)OC(Br)(Br)C(C)(C)CBr JEJAMASKDTUEBZ-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Lock And Its Accessories (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9412385A GB9412385D0 (en) | 1994-06-21 | 1994-06-21 | Chemical compounds |
| GB9412492A GB9412492D0 (en) | 1994-06-22 | 1994-06-22 | Chemical compounds |
| PCT/GB1995/001459 WO1995035281A1 (en) | 1994-06-21 | 1995-06-21 | Tri-substituted phenyl derivates useful as pde iv inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO965524L NO965524L (no) | 1996-12-20 |
| NO965524D0 NO965524D0 (no) | 1996-12-20 |
| NO312672B1 true NO312672B1 (no) | 2002-06-17 |
Family
ID=26305090
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19965524A NO312672B1 (no) | 1994-06-21 | 1996-12-20 | Tri-substituerte fenylderivater anvendelige som PDE IV- inhibitorer, fremgangsmåte for fremstilling derav og farmasöytiskepreparater inneholdende dem |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US5786354A (cs) |
| EP (1) | EP0770065B1 (cs) |
| JP (1) | JP3856465B2 (cs) |
| CN (1) | CN1304372C (cs) |
| AT (1) | ATE263153T1 (cs) |
| AU (1) | AU707472B2 (cs) |
| CZ (1) | CZ293311B6 (cs) |
| DE (1) | DE69532808T2 (cs) |
| DK (1) | DK0770065T3 (cs) |
| ES (1) | ES2218548T3 (cs) |
| FI (1) | FI115302B (cs) |
| HU (1) | HUT76803A (cs) |
| NO (1) | NO312672B1 (cs) |
| NZ (1) | NZ288294A (cs) |
| PT (1) | PT770065E (cs) |
| RU (1) | RU2201921C2 (cs) |
| SK (1) | SK282661B6 (cs) |
| WO (1) | WO1995035281A1 (cs) |
Families Citing this family (84)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9222253D0 (en) * | 1992-10-23 | 1992-12-09 | Celltech Ltd | Chemical compounds |
| GB9304919D0 (en) * | 1993-03-10 | 1993-04-28 | Celltech Ltd | Chemical compounds |
| GB9304920D0 (en) * | 1993-03-10 | 1993-04-28 | Celltech Ltd | Chemical compounds |
| WO1995017399A1 (en) * | 1993-12-22 | 1995-06-29 | Celltech Therapeutics Limited | Trisubstituted phenyl derivatives, processes for their preparation and their use as phosphodiesterase (type iv) inhibitors |
| US5786354A (en) * | 1994-06-21 | 1998-07-28 | Celltech Therapeutics, Limited | Tri-substituted phenyl derivatives and processes for their preparation |
| US6245774B1 (en) | 1994-06-21 | 2001-06-12 | Celltech Therapeutics Limited | Tri-substituted phenyl or pyridine derivatives |
| GB9412571D0 (en) | 1994-06-22 | 1994-08-10 | Celltech Ltd | Chemical compounds |
| GB9412573D0 (en) | 1994-06-22 | 1994-08-10 | Celltech Ltd | Chemical compounds |
| GB9523675D0 (en) | 1995-11-20 | 1996-01-24 | Celltech Therapeutics Ltd | Chemical compounds |
| WO1997022586A1 (en) * | 1995-12-15 | 1997-06-26 | Merck Frosst Canada Inc. | Tri-aryl ethane derivatives as pde iv inhibitors |
| US5710170A (en) * | 1995-12-15 | 1998-01-20 | Merck Frosst Canada, Inc. | Tri-aryl ethane derivatives as PDE IV inhibitors |
| GB9526245D0 (en) * | 1995-12-21 | 1996-02-21 | Celltech Therapeutics Ltd | Chemical compounds |
| GB9526246D0 (en) * | 1995-12-21 | 1996-02-21 | Celltech Therapeutics Ltd | Chemical compounds |
| GB9526243D0 (en) * | 1995-12-21 | 1996-02-21 | Celltech Therapeutics Ltd | Chemical compounds |
| DE19605766A1 (de) * | 1996-02-16 | 1997-08-21 | Basf Ag | Substituierte 2-Phenylpyridine |
| GB9608435D0 (en) * | 1996-04-24 | 1996-06-26 | Celltech Therapeutics Ltd | Chemical compounds |
| GB9619284D0 (en) * | 1996-09-16 | 1996-10-30 | Celltech Therapeutics Ltd | Chemical compounds |
| GB9622363D0 (en) | 1996-10-28 | 1997-01-08 | Celltech Therapeutics Ltd | Chemical compounds |
| GB9625184D0 (en) * | 1996-12-04 | 1997-01-22 | Celltech Therapeutics Ltd | Chemical compounds |
| JP2001507349A (ja) * | 1996-12-23 | 2001-06-05 | セルテック セラピューティックス リミテッド | 縮合多環式２−アミノピリミジン誘導体、それらの製造およびたんぱく質チロシンキナーゼ抑制因子としてのそれらの使用 |
| GB9705361D0 (en) * | 1997-03-14 | 1997-04-30 | Celltech Therapeutics Ltd | Chemical compounds |
| GB9713087D0 (en) * | 1997-06-20 | 1997-08-27 | Celltech Therapeutics Ltd | Chemical compounds |
| US6180650B1 (en) * | 1999-04-23 | 2001-01-30 | Merck Frosst Canada & Co. | Heterosubstituted pyridine derivatives as PDE 4 inhibitors |
| GB9914258D0 (en) | 1999-06-18 | 1999-08-18 | Celltech Therapeutics Ltd | Chemical compounds |
| TR200201317T2 (tr) | 1999-08-21 | 2002-11-21 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Sinerjistik kombinasyon. |
| EP1229934B1 (en) | 1999-10-01 | 2014-03-05 | Immunogen, Inc. | Compositions and methods for treating cancer using immunoconjugates and chemotherapeutic agents |
| GB9924862D0 (en) * | 1999-10-20 | 1999-12-22 | Celltech Therapeutics Ltd | Chemical compounds |
| US6410563B1 (en) | 1999-12-22 | 2002-06-25 | Merck Frosst Canada & Co. | Substituted 8-arylquinoline phosphodiesterase-4 inhibitors |
| US6639077B2 (en) | 2000-03-23 | 2003-10-28 | Merck Frosst Canada & Co. | Tri-aryl-substituted-ethane PDE4 inhibitors |
| MY123585A (en) * | 2000-03-23 | 2006-05-31 | Merck Canada Inc | Tri-aryl-substituted-ethane pde4 inhibitors. |
| JP2003534328A (ja) | 2000-05-25 | 2003-11-18 | メルク フロスト カナダ アンド カンパニー | フルオロアルコキシ置換ベンズアミドジクロロピリジニルｎ−オキシドｐｄｅ４阻害剤 |
| US6740666B2 (en) | 2000-12-20 | 2004-05-25 | Merck & Co., Inc. | Substituted 8-arylquinoline phosphodiesterase-4 inhibitors |
| US6699890B2 (en) | 2000-12-22 | 2004-03-02 | Memory Pharmaceuticals Corp. | Phosphodiesterase 4 inhibitors |
| DE10064997A1 (de) | 2000-12-23 | 2002-06-27 | Merck Patent Gmbh | Benzoylpyridazine |
| US7153871B2 (en) * | 2001-01-22 | 2006-12-26 | Memory Pharmaceuticals Corporation | Phosphodiesterase 4 inhibitors, including aminoindazole and aminobenzofuran analogs |
| US7205320B2 (en) * | 2001-01-22 | 2007-04-17 | Memory Pharmaceuticals Corp. | Phosphodiesterase 4 inhibitors |
| CA2447765C (en) | 2001-05-24 | 2011-01-25 | Merck Frosst Canada & Co./Merck Frosst Canada & Cie | 1-biaryl-1,8-napthyridin-4-one phosphodiesterase-4 inhibitors |
| MXPA03010810A (es) * | 2001-05-29 | 2004-03-22 | Schering Ag | Pirimidinas inhibidoras de cdk, su obtencion y su uso como medicamentos. |
| JO2311B1 (en) | 2001-08-29 | 2005-09-12 | ميرك فروست كندا ليمتد | Alkyl inhibitors Ariel phosphodiesterase-4 |
| DE10150517A1 (de) * | 2001-10-12 | 2003-04-17 | Merck Patent Gmbh | Verwendung von Phosphodiesterase IV-Inhibitoren |
| CA2492911A1 (en) * | 2002-07-19 | 2004-01-29 | Memory Pharmaceuticals Corporation | 6-amino-1h-indazole and 4-aminobenzofuran compounds as phosphodiesterase 4 inhibitors |
| HRP20050083A2 (en) | 2002-07-19 | 2005-08-31 | Memory Pharmaceuticals Corporation | Phosphodiesterase 4 inhibitors, including n-substituted aniline and diphenylamine analogs |
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1995
- 1995-06-20 US US08/492,639 patent/US5786354A/en not_active Expired - Fee Related
- 1995-06-21 NZ NZ288294A patent/NZ288294A/xx unknown
- 1995-06-21 RU RU97100794/04A patent/RU2201921C2/ru not_active IP Right Cessation
- 1995-06-21 WO PCT/GB1995/001459 patent/WO1995035281A1/en active IP Right Grant
- 1995-06-21 PT PT95922633T patent/PT770065E/pt unknown
- 1995-06-21 EP EP95922633A patent/EP0770065B1/en not_active Expired - Lifetime
- 1995-06-21 JP JP50184396A patent/JP3856465B2/ja not_active Expired - Fee Related
- 1995-06-21 SK SK1630-96A patent/SK282661B6/sk unknown
- 1995-06-21 DE DE1995632808 patent/DE69532808T2/de not_active Expired - Fee Related
- 1995-06-21 CN CNB951937405A patent/CN1304372C/zh not_active Expired - Fee Related
- 1995-06-21 ES ES95922633T patent/ES2218548T3/es not_active Expired - Lifetime
- 1995-06-21 CZ CZ19963730A patent/CZ293311B6/cs not_active IP Right Cessation
- 1995-06-21 AU AU27461/95A patent/AU707472B2/en not_active Ceased
- 1995-06-21 HU HU9603578A patent/HUT76803A/hu unknown
- 1995-06-21 DK DK95922633T patent/DK0770065T3/da active
- 1995-06-21 AT AT95922633T patent/ATE263153T1/de not_active IP Right Cessation
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1996
- 1996-12-19 FI FI965126A patent/FI115302B/fi active IP Right Grant
- 1996-12-20 NO NO19965524A patent/NO312672B1/no unknown
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- 1998-03-26 US US09/048,592 patent/US6077854A/en not_active Expired - Fee Related
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| RU2201921C2 (ru) | 2003-04-10 |
| EP0770065A1 (en) | 1997-05-02 |
| CZ373096A3 (en) | 1997-08-13 |
| FI965126A7 (fi) | 1996-12-19 |
| JP3856465B2 (ja) | 2006-12-13 |
| FI965126A0 (fi) | 1996-12-19 |
| CN1304372C (zh) | 2007-03-14 |
| SK282661B6 (sk) | 2002-11-06 |
| AU707472B2 (en) | 1999-07-08 |
| US5786354A (en) | 1998-07-28 |
| ATE263153T1 (de) | 2004-04-15 |
| DK0770065T3 (da) | 2004-07-19 |
| FI115302B (fi) | 2005-04-15 |
| US6077854A (en) | 2000-06-20 |
| NO965524L (no) | 1996-12-20 |
| DE69532808T2 (de) | 2005-01-13 |
| SK163096A3 (en) | 1997-10-08 |
| DE69532808D1 (de) | 2004-05-06 |
| CN1151732A (zh) | 1997-06-11 |
| HUT76803A (en) | 1997-11-28 |
| CZ293311B6 (cs) | 2004-03-17 |
| PT770065E (pt) | 2004-08-31 |
| AU2746195A (en) | 1996-01-15 |
| NZ288294A (en) | 1999-01-28 |
| JPH10503173A (ja) | 1998-03-24 |
| WO1995035281A1 (en) | 1995-12-28 |
| ES2218548T3 (es) | 2004-11-16 |
| EP0770065B1 (en) | 2004-03-31 |
| NO965524D0 (no) | 1996-12-20 |
| HU9603578D0 (en) | 1997-02-28 |
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