NO314730B1 - Nye dipeptidforbindelser eller farmasöytisk akseptable salter derav og anvendelse derav til fremstilling av preparater, samt anti-AIDS-middelog fremgangsmåte for fremstilling av slike forbindelser - Google Patents
Nye dipeptidforbindelser eller farmasöytisk akseptable salter derav og anvendelse derav til fremstilling av preparater, samt anti-AIDS-middelog fremgangsmåte for fremstilling av slike forbindelser Download PDFInfo
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- NO314730B1 NO314730B1 NO19962748A NO962748A NO314730B1 NO 314730 B1 NO314730 B1 NO 314730B1 NO 19962748 A NO19962748 A NO 19962748A NO 962748 A NO962748 A NO 962748A NO 314730 B1 NO314730 B1 NO 314730B1
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- Prior art keywords
- group
- compound
- general formula
- hydroxy
- amino
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 222
- 108010016626 Dipeptides Proteins 0.000 title claims abstract description 66
- 150000003839 salts Chemical class 0.000 title claims abstract description 26
- 238000002360 preparation method Methods 0.000 title claims description 16
- 238000000034 method Methods 0.000 title description 28
- 239000002259 anti human immunodeficiency virus agent Substances 0.000 title description 4
- -1 chloromethylene Chemical group 0.000 claims abstract description 39
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 15
- 208000030507 AIDS Diseases 0.000 claims abstract description 11
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 9
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 9
- 239000004615 ingredient Substances 0.000 claims abstract description 6
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract description 5
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims abstract description 5
- 125000003277 amino group Chemical group 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 241000725303 Human immunodeficiency virus Species 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 238000001727 in vivo Methods 0.000 claims description 8
- 125000004434 sulfur atom Chemical group 0.000 claims description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 230000006181 N-acylation Effects 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
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- 125000002950 monocyclic group Chemical group 0.000 abstract 2
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- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 85
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 75
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- 239000000047 product Substances 0.000 description 57
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- 238000001269 time-of-flight mass spectrometry Methods 0.000 description 42
- 238000000746 purification Methods 0.000 description 37
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- 239000000725 suspension Substances 0.000 description 31
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L magnesium sulphate Substances [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 22
- 239000004030 hiv protease inhibitor Substances 0.000 description 21
- 239000000243 solution Substances 0.000 description 21
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 20
- 235000019341 magnesium sulphate Nutrition 0.000 description 20
- 229940122440 HIV protease inhibitor Drugs 0.000 description 16
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 12
- TZGPACAKMCUCKX-UHFFFAOYSA-N 2-hydroxyacetamide Chemical compound NC(=O)CO TZGPACAKMCUCKX-UHFFFAOYSA-N 0.000 description 12
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
- 238000001953 recrystallisation Methods 0.000 description 12
- 229910000029 sodium carbonate Inorganic materials 0.000 description 12
- RIERSGULWXEJKL-UHFFFAOYSA-N 3-hydroxy-2-methylbenzoic acid Chemical compound CC1=C(O)C=CC=C1C(O)=O RIERSGULWXEJKL-UHFFFAOYSA-N 0.000 description 11
- 238000009833 condensation Methods 0.000 description 11
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- 229910001868 water Inorganic materials 0.000 description 11
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
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- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 8
- 239000010410 layer Substances 0.000 description 8
- 210000004027 cell Anatomy 0.000 description 7
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 7
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
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- RCGJBBOBRZDMTL-UHFFFAOYSA-N 2-ethyl-3-hydroxybenzoic acid Chemical compound CCC1=C(O)C=CC=C1C(O)=O RCGJBBOBRZDMTL-UHFFFAOYSA-N 0.000 description 5
- NJBBLOIWMSYVCQ-VZTVMPNDSA-N Kynostatin 272 Chemical compound C([C@H](NC(=O)[C@@H](NC(=O)COC=1C2=CC=NC=C2C=CC=1)CSC)[C@H](O)C(=O)N1[C@@H](CSC1)C(=O)NC(C)(C)C)C1=CC=CC=C1 NJBBLOIWMSYVCQ-VZTVMPNDSA-N 0.000 description 5
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- 239000003826 tablet Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000004149 thio group Chemical group *S* 0.000 description 1
- QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 description 1
- DZLNHFMRPBPULJ-UHFFFAOYSA-N thioproline Chemical compound OC(=O)C1CSCN1 DZLNHFMRPBPULJ-UHFFFAOYSA-N 0.000 description 1
- 229940104230 thymidine Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/04—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D277/06—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/04—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D263/06—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by oxygen atoms, attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18815195 | 1995-06-30 | ||
| JP14067896 | 1996-05-10 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO962748D0 NO962748D0 (no) | 1996-06-28 |
| NO962748L NO962748L (no) | 1997-01-02 |
| NO314730B1 true NO314730B1 (no) | 2003-05-12 |
Family
ID=26473119
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19962748A NO314730B1 (no) | 1995-06-30 | 1996-06-28 | Nye dipeptidforbindelser eller farmasöytisk akseptable salter derav og anvendelse derav til fremstilling av preparater, samt anti-AIDS-middelog fremgangsmåte for fremstilling av slike forbindelser |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US5932550A (es) |
| EP (1) | EP0751145B1 (es) |
| AT (1) | ATE266039T1 (es) |
| AU (1) | AU705193B2 (es) |
| CA (1) | CA2179935C (es) |
| DE (1) | DE69632365T2 (es) |
| DK (1) | DK0751145T3 (es) |
| ES (1) | ES2220963T3 (es) |
| NO (1) | NO314730B1 (es) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6313094B1 (en) | 1990-12-11 | 2001-11-06 | Japan Energy Corporation | β-amino-α-hydroxycarboxylic acid derivatives and HIV protease inhibitors |
| WO1999029311A1 (en) * | 1997-12-08 | 1999-06-17 | The Scripps Research Institute | Hiv/fiv protease inhibitors having a small p3 residue |
| US6803466B1 (en) * | 1997-12-08 | 2004-10-12 | The Scripps Research Institute | HIV/FIV protease inhibitors having a small P3 residue |
| WO2001047948A1 (fr) * | 1999-12-28 | 2001-07-05 | Japan Energy Corporation | Nouveau composé dipeptidique et ses applications en médecine |
| US6589962B1 (en) | 1999-07-20 | 2003-07-08 | Merck & Co., Inc. | Alpha-hydroxy-gamma-[[(carbocyclic-or heterocyclic-substituted)amino]carbonyl]alkanamide derivatives and uses thereof |
| MXPA02001349A (es) * | 1999-08-09 | 2002-07-22 | Tripep Ab | Inhibidores de la polimerizacion de proteinas y metodos de uso. |
| US6287688B1 (en) * | 2000-03-03 | 2001-09-11 | E. I. Du Pont De Nemours And Company | Partially oriented poly(trimethylene terephthalate) yarn |
| HN2002000136A (es) * | 2001-06-11 | 2003-07-31 | Basf Ag | Inhibidores de la proteasa del virus hiv, compuestos que contienen a los mismos, sus usos farmaceuticos y los materiales para su sintesis |
| US7169932B2 (en) * | 2001-06-11 | 2007-01-30 | Pfizer Inc. | HIV protease inhibitors, compositions containing the same, their pharmaceutical uses, material for their synthesis |
| US7094909B2 (en) | 2001-06-11 | 2006-08-22 | Agouron Pharmaceuticals, Inc. | HIV protease inhibitors, compositions containing the same, their pharmaceutical uses and materials for their synthesis |
| US6593455B2 (en) * | 2001-08-24 | 2003-07-15 | Tripep Ab | Tripeptide amides that block viral infectivity and methods of use thereof |
| WO2003024995A1 (en) * | 2001-09-19 | 2003-03-27 | Tripep Ab | Molecules that block viral infectivity and methods of use thereof |
| JP2006518373A (ja) * | 2003-02-21 | 2006-08-10 | トリペップ アクチ ボラゲット | Ｈｉｖ複製を抑制するためのグリシンアミド誘導体 |
| US20050096319A1 (en) * | 2003-02-21 | 2005-05-05 | Balzarini Jan M.R. | Identification of compounds that inhibit replication of human immunodeficiency virus |
| US6955002B2 (en) * | 2003-03-18 | 2005-10-18 | Sandel Medical Industries Llc | Medication marking system |
| WO2005026114A1 (en) * | 2003-09-17 | 2005-03-24 | Pfizer Inc. | Hiv protease inhibitors, compositions containing the same and their pharmaceutical uses |
| EP1692104A1 (en) * | 2003-12-04 | 2006-08-23 | Pfizer Inc. | Methods of preparing compounds useful as protease inhibitors |
| WO2005054186A2 (en) * | 2003-12-04 | 2005-06-16 | Pfizer Inc. | Methods for the preparation of stereoisomerically enriched amines |
| JP2007513142A (ja) * | 2003-12-04 | 2007-05-24 | ファイザー インコーポレイテッド | プロテアーゼ阻害剤として有用な化合物の製造法 |
| CN103582630B (zh) | 2011-05-31 | 2016-08-17 | 施万生物制药研发Ip有限责任公司 | 脑啡肽酶抑制剂 |
| CA2835216A1 (en) | 2011-05-31 | 2012-12-06 | Theravance, Inc. | Neprilysin inhibitors |
| US8686184B2 (en) | 2011-05-31 | 2014-04-01 | Theravance, Inc. | Neprilysin inhibitors |
Family Cites Families (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1989003842A1 (en) * | 1987-10-21 | 1989-05-05 | The Upjohn Company | Renin inhibitors containing a (1-amino-2-hydroxy-2-heterocyclic) ethyl moiety |
| US4963655A (en) * | 1988-05-27 | 1990-10-16 | Mayo Foundation For Medical Education And Research | Boron analogs of amino acid/peptide protease inhibitors |
| US5086165A (en) * | 1989-03-08 | 1992-02-04 | Washington University | Inhibitors of retroviral protease with a ketomethylene isosteric replaced amide bond |
| US5342922A (en) * | 1989-03-08 | 1994-08-30 | Washington University | Inhibitors of retroviral protease |
| DE3913272A1 (de) * | 1989-04-22 | 1990-10-25 | Hoechst Ag | Dipeptid-derivate mit enzym-inhibitorischer wirkung |
| US5212157A (en) * | 1989-06-06 | 1993-05-18 | Bio-Mega, Inc. | Enzyme inhibitors |
| US5126326A (en) * | 1989-06-06 | 1992-06-30 | Bio-Mega, Inc. | Enzyme inhibiting peptide derivatives |
| DE4001236A1 (de) * | 1990-01-18 | 1991-07-25 | Bayer Ag | Neue peptide, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel, insbesondere als arzneimittel gegen retroviren |
| EP0438311A3 (en) * | 1990-01-19 | 1992-07-01 | Merck & Co. Inc. | Di- and tripeptide renin inhibitors |
| WO1992003472A1 (en) * | 1990-08-24 | 1992-03-05 | The Upjohn Company | Peptides containing amino-polyols as transition-state mimics |
| US5187074A (en) * | 1990-10-11 | 1993-02-16 | Merck & Co., Inc. | Method of hydroxylation with ATCC 55086 |
| US5192668A (en) * | 1990-10-11 | 1993-03-09 | Merck & Co., Inc. | Synthesis of protease inhibitor |
| US5188950A (en) * | 1990-10-11 | 1993-02-23 | Merck & Co., Inc. | Method of preparing HIV protease inhibitors |
| US5475013A (en) * | 1990-11-19 | 1995-12-12 | Monsanto Company | Retroviral protease inhibitors |
| US5438118A (en) * | 1990-11-30 | 1995-08-01 | Smithkline Beechman Corp. | HIV protease inhibitors |
| CA2056911C (en) * | 1990-12-11 | 1998-09-22 | Yuuichi Nagano | Hiv protease inhibitors |
| AU647239B2 (en) * | 1991-02-08 | 1994-03-17 | Sankyo Company Limited | New beta-amino- alpha-hydroxycarboxylic acids and their use |
| IE922316A1 (en) * | 1991-07-17 | 1993-01-27 | Smithkline Beecham Corp | Retroviral protease inhibitors |
| WO1993008184A1 (en) * | 1991-10-23 | 1993-04-29 | Merck & Co., Inc. | Hiv protease inhibitors |
| US5644028A (en) * | 1992-05-13 | 1997-07-01 | Japan Energy Corporation | Process for producing peptide derivatives and salts therefor |
| FI933472A (fi) * | 1992-08-07 | 1994-02-08 | Sankyo Co | Peptider med foermaoga att inhibera effekten av HIV-proteas, deras framstaellning och terapeutiska anvaendning |
| US5554653A (en) * | 1992-12-22 | 1996-09-10 | Eli Lilly And Company | Inhibitors of HIV protease useful for the treatment of AIDS |
| ES2150933T3 (es) * | 1992-12-22 | 2000-12-16 | Lilly Co Eli | Inhibidores de la proteasa vih utiles para el tratamiento del sida. |
| US5434265A (en) * | 1992-12-22 | 1995-07-18 | Eli Lilly And Company | Inhibitors of HIV protease |
| US5491166A (en) * | 1992-12-22 | 1996-02-13 | Eli Lilly And Company | Inhibitors of HIV protease useful for the treatment of AIDS |
| MX9308016A (es) * | 1992-12-22 | 1994-08-31 | Lilly Co Eli | Compuestos inhibidores de la proteasa del virus de la inmunodeficiencia humana, procedimiento para su preparacion y formulacion farmaceutica que los contiene. |
| WO1994018192A1 (en) * | 1993-02-12 | 1994-08-18 | Merck & Co., Inc. | Piperazine derivatives as hiv protease inhibitors |
| AU6828894A (en) * | 1993-05-14 | 1994-12-12 | Merck & Co., Inc. | Hiv protease inhibitors |
| US5587514A (en) * | 1993-11-08 | 1996-12-24 | Emory University | Diastereoselective synthesis of hydroxyethylene dipeptide isosteres |
| US5476874A (en) * | 1994-06-22 | 1995-12-19 | Merck & Co., Inc. | New HIV protease inhibitors |
| US5492910A (en) * | 1994-11-17 | 1996-02-20 | Bristol-Myers Squibb Co. | Retrocarbamate protease inhibitors |
| WO1996028423A1 (fr) * | 1995-03-15 | 1996-09-19 | Sankyo Company, Limited | Composes dipeptidiques de structure ahpba |
-
1996
- 1996-06-26 CA CA2179935A patent/CA2179935C/en not_active Expired - Fee Related
- 1996-06-26 US US08/669,757 patent/US5932550A/en not_active Expired - Lifetime
- 1996-06-28 AT AT96304764T patent/ATE266039T1/de active
- 1996-06-28 AU AU56285/96A patent/AU705193B2/en not_active Ceased
- 1996-06-28 DK DK96304764T patent/DK0751145T3/da active
- 1996-06-28 NO NO19962748A patent/NO314730B1/no not_active IP Right Cessation
- 1996-06-28 DE DE69632365T patent/DE69632365T2/de not_active Expired - Lifetime
- 1996-06-28 ES ES96304764T patent/ES2220963T3/es not_active Expired - Lifetime
- 1996-06-28 EP EP96304764A patent/EP0751145B1/en not_active Expired - Lifetime
-
1998
- 1998-08-21 US US09/137,608 patent/US5962640A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CA2179935C (en) | 2010-09-07 |
| AU705193B2 (en) | 1999-05-20 |
| NO962748L (no) | 1997-01-02 |
| US5932550A (en) | 1999-08-03 |
| DE69632365T2 (de) | 2005-05-04 |
| EP0751145A3 (en) | 1997-10-08 |
| AU5628596A (en) | 1997-02-06 |
| DK0751145T3 (da) | 2004-08-30 |
| ES2220963T3 (es) | 2004-12-16 |
| EP0751145A2 (en) | 1997-01-02 |
| EP0751145B1 (en) | 2004-05-06 |
| ATE266039T1 (de) | 2004-05-15 |
| DE69632365D1 (de) | 2004-06-09 |
| NO962748D0 (no) | 1996-06-28 |
| CA2179935A1 (en) | 1996-12-31 |
| US5962640A (en) | 1999-10-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |