ZA200005238B - Pyrrolidines as inhibitors of neuraminidases. - Google Patents
Pyrrolidines as inhibitors of neuraminidases. Download PDFInfo
- Publication number
- ZA200005238B ZA200005238B ZA200005238A ZA200005238A ZA200005238B ZA 200005238 B ZA200005238 B ZA 200005238B ZA 200005238 A ZA200005238 A ZA 200005238A ZA 200005238 A ZA200005238 A ZA 200005238A ZA 200005238 B ZA200005238 B ZA 200005238B
- Authority
- ZA
- South Africa
- Prior art keywords
- hydrogen
- acetamido
- pyrrolidine
- carboxylic acid
- cis
- Prior art date
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- 102000005348 Neuraminidase Human genes 0.000 title claims description 32
- 108010006232 Neuraminidase Proteins 0.000 title claims description 32
- 239000003112 inhibitor Substances 0.000 title description 2
- 150000003235 pyrrolidines Chemical class 0.000 title description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 104
- 239000001257 hydrogen Substances 0.000 claims description 101
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 72
- 150000001875 compounds Chemical class 0.000 claims description 67
- 125000003342 alkenyl group Chemical group 0.000 claims description 61
- 125000000623 heterocyclic group Chemical group 0.000 claims description 57
- 238000000034 method Methods 0.000 claims description 47
- 125000000217 alkyl group Chemical group 0.000 claims description 44
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- 150000002431 hydrogen Chemical class 0.000 claims description 26
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- -1 N-methylaminomethyl Chemical group 0.000 claims description 13
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- 125000003710 aryl alkyl group Chemical group 0.000 claims description 9
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 6
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 5
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims description 5
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 4
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
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- LLAPDLPYIYKTGQ-UHFFFAOYSA-N 1-aminoethyl Chemical group C[CH]N LLAPDLPYIYKTGQ-UHFFFAOYSA-N 0.000 claims description 3
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 3
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 3
- 229910006069 SO3H Inorganic materials 0.000 claims description 2
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- 239000000126 substance Substances 0.000 claims 32
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 5
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- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 1
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- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 claims 1
- 125000004706 n-propylthio group Chemical group C(CC)S* 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
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- 150000007524 organic acids Chemical class 0.000 claims 1
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- DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- 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
- C07D207/30—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 two double bonds between ring members or between ring members and non-ring members
- C07D207/32—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 two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/325—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 two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
- C07D207/327—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
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- A61P31/16—Antivirals for RNA viruses for influenza or rhinoviruses
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
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- 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
- C07D401/02—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
- C07D401/12—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 linked by a chain containing hetero atoms as chain links
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- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/572—Five-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Virology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Pulmonology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US6522598A | 1998-04-23 | 1998-04-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200005238B true ZA200005238B (en) | 2001-12-04 |
Family
ID=22061195
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200005238A ZA200005238B (en) | 1998-04-23 | 2000-09-28 | Pyrrolidines as inhibitors of neuraminidases. |
Country Status (17)
| Country | Link |
|---|---|
| EP (1) | EP1315698A1 (sk) |
| JP (1) | JP2002512224A (sk) |
| CN (1) | CN1328546A (sk) |
| AR (1) | AR018196A1 (sk) |
| AU (1) | AU3554599A (sk) |
| BG (1) | BG104962A (sk) |
| BR (1) | BR9909870A (sk) |
| CA (1) | CA2329422A1 (sk) |
| CO (1) | CO5011122A1 (sk) |
| HU (1) | HUP0101224A3 (sk) |
| IL (1) | IL138601A0 (sk) |
| NO (1) | NO20005301L (sk) |
| PL (1) | PL343678A1 (sk) |
| SK (1) | SK15092000A3 (sk) |
| TR (1) | TR200003065T2 (sk) |
| WO (1) | WO1999054299A1 (sk) |
| ZA (1) | ZA200005238B (sk) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK0933993T3 (da) | 1996-06-14 | 2006-08-14 | Biocryst Pharm Inc | Substituerede cyclopentanforbindelser, der er egnede som neuraminidaseinhibitorer |
| BR9813480A (pt) | 1997-12-17 | 2000-10-10 | Biocryst Pharm Inc | Compostos inibidores de neuraminidase de ciclopentano substituìdo, composição e métodos de inibição da neuraminidase do vìrus da influenza- e de tratamento de infecção por vìrus da influenza- |
| US6455571B1 (en) | 1998-04-23 | 2002-09-24 | Abbott Laboratories | Inhibitors of neuraminidases |
| US6503745B1 (en) | 1998-11-05 | 2003-01-07 | Biocryst Pharmaceuticals, Inc. | Cyclopentane and cyclopentene compounds and use for detecting influenza virus |
| WO2001080892A1 (fr) * | 2000-04-25 | 2001-11-01 | Sankyo Company, Limited | Substances preventives de la grippe |
| US6518299B1 (en) | 2000-10-20 | 2003-02-11 | Biocryst Pharmaceuticals, Inc. | Substituted pyrrolidine compounds useful as neuraminidase inhibitors |
| WO2002081441A1 (en) * | 2001-04-03 | 2002-10-17 | Abbott Laboratories | Process for the preparation of substituted pyrrolidine neuraminidase inhibitors |
| ES2289161T3 (es) * | 2001-11-02 | 2008-02-01 | Glaxo Group Limited | Derivados de 4-(heteroaril de 6 miembros)-acil pirrolidina como inhibidores de hcv. |
| EP1440070A1 (en) * | 2001-11-02 | 2004-07-28 | Glaxo Group Limited | 4-(5-membered)-heteroaryl acyl pyrrolidine derivatives as hcv inhibitors |
| BR0315417A (pt) | 2002-10-24 | 2005-08-16 | Glaxo Group Ltd | Derivados 1-acil-pirrolidina para o tratamento de infecções virais |
| CN104402754B (zh) * | 2014-11-25 | 2016-03-02 | 广东东阳光药业有限公司 | 作为神经氨酸酶抑制剂的化合物及其在药物中的应用 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4035961A1 (de) * | 1990-11-02 | 1992-05-07 | Thomae Gmbh Dr K | Cyclische iminoderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
| BR9607098B8 (pt) * | 1995-02-27 | 2014-11-18 | Gilead Sciences Inc | Composto e composição farmacêutica. |
| DK0933993T3 (da) * | 1996-06-14 | 2006-08-14 | Biocryst Pharm Inc | Substituerede cyclopentanforbindelser, der er egnede som neuraminidaseinhibitorer |
| ZA988469B (en) * | 1997-09-17 | 1999-03-17 | Biocryst Pharm Inc | Pyrrolidin-2-one compounds and their use as neuraminidase inhibitors |
-
1999
- 1999-04-12 CA CA002329422A patent/CA2329422A1/en not_active Abandoned
- 1999-04-12 EP EP99917414A patent/EP1315698A1/en not_active Withdrawn
- 1999-04-12 BR BR9909870-9A patent/BR9909870A/pt not_active IP Right Cessation
- 1999-04-12 CN CN99807610A patent/CN1328546A/zh active Pending
- 1999-04-12 PL PL99343678A patent/PL343678A1/xx unknown
- 1999-04-12 SK SK1509-2000A patent/SK15092000A3/sk unknown
- 1999-04-12 TR TR2000/03065T patent/TR200003065T2/xx unknown
- 1999-04-12 IL IL13860199A patent/IL138601A0/xx unknown
- 1999-04-12 HU HU0101224A patent/HUP0101224A3/hu unknown
- 1999-04-12 WO PCT/US1999/007945 patent/WO1999054299A1/en not_active Application Discontinuation
- 1999-04-12 JP JP2000544640A patent/JP2002512224A/ja not_active Withdrawn
- 1999-04-12 AU AU35545/99A patent/AU3554599A/en not_active Abandoned
- 1999-04-21 CO CO99024047A patent/CO5011122A1/es unknown
- 1999-04-23 AR ARP990101905A patent/AR018196A1/es not_active Application Discontinuation
-
2000
- 2000-09-28 ZA ZA200005238A patent/ZA200005238B/en unknown
- 2000-10-20 NO NO20005301A patent/NO20005301L/no not_active Application Discontinuation
- 2000-11-17 BG BG104962A patent/BG104962A/bg unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AR018196A1 (es) | 2001-10-31 |
| BG104962A (bg) | 2001-07-31 |
| CA2329422A1 (en) | 1999-10-28 |
| JP2002512224A (ja) | 2002-04-23 |
| SK15092000A3 (sk) | 2001-05-10 |
| TR200003065T2 (tr) | 2001-02-21 |
| AU3554599A (en) | 1999-11-08 |
| WO1999054299A1 (en) | 1999-10-28 |
| BR9909870A (pt) | 2000-12-19 |
| HUP0101224A2 (hu) | 2001-08-28 |
| IL138601A0 (en) | 2001-10-31 |
| CO5011122A1 (es) | 2001-02-28 |
| NO20005301D0 (no) | 2000-10-20 |
| NO20005301L (no) | 2000-12-08 |
| CN1328546A (zh) | 2001-12-26 |
| EP1315698A1 (en) | 2003-06-04 |
| HUP0101224A3 (en) | 2002-12-28 |
| PL343678A1 (en) | 2001-08-27 |
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