PH26906A - Bis-arylposphate ester antagonists of platelet activating factor - Google Patents
Bis-arylposphate ester antagonists of platelet activating factor Download PDFInfo
- Publication number
- PH26906A PH26906A PH39725A PH39725A PH26906A PH 26906 A PH26906 A PH 26906A PH 39725 A PH39725 A PH 39725A PH 39725 A PH39725 A PH 39725A PH 26906 A PH26906 A PH 26906A
- Authority
- PH
- Philippines
- Prior art keywords
- hydroxide
- methyl
- inner salt
- phenyl
- oxy
- Prior art date
Links
- HVAUUPRFYPCOCA-AREMUKBSSA-N 2-O-acetyl-1-O-hexadecyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCOC[C@@H](OC(C)=O)COP([O-])(=O)OCC[N+](C)(C)C HVAUUPRFYPCOCA-AREMUKBSSA-N 0.000 title description 59
- 108010003541 Platelet Activating Factor Proteins 0.000 title description 58
- 239000005557 antagonist Substances 0.000 title description 5
- 150000002148 esters Chemical class 0.000 title description 2
- 150000003839 salts Chemical class 0.000 claims description 647
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 642
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 533
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 431
- -1 tetradecyloxy Chemical group 0.000 claims description 418
- 150000001875 compounds Chemical class 0.000 claims description 162
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 151
- 239000000203 mixture Substances 0.000 claims description 124
- 125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000004001 thioalkyl group Chemical group 0.000 claims description 2
- 241001504505 Troglodytes troglodytes Species 0.000 claims 2
- 241001674788 Pasites Species 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
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- 239000000243 solution Substances 0.000 description 113
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 108
- 239000002904 solvent Substances 0.000 description 94
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 87
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 87
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 77
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 70
- 238000003756 stirring Methods 0.000 description 63
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 62
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 60
- 229960001701 chloroform Drugs 0.000 description 60
- 229950005499 carbon tetrachloride Drugs 0.000 description 54
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 53
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 52
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- 235000020357 syrup Nutrition 0.000 description 16
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- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 15
- 210000001772 blood platelet Anatomy 0.000 description 15
- 238000001816 cooling Methods 0.000 description 15
- 230000005764 inhibitory process Effects 0.000 description 15
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 15
- 239000000391 magnesium silicate Substances 0.000 description 15
- 229910052919 magnesium silicate Inorganic materials 0.000 description 15
- 235000019792 magnesium silicate Nutrition 0.000 description 15
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 14
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- 238000002474 experimental method Methods 0.000 description 13
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- KOFZTCSTGIWCQG-UHFFFAOYSA-N 1-bromotetradecane Chemical compound CCCCCCCCCCCCCCBr KOFZTCSTGIWCQG-UHFFFAOYSA-N 0.000 description 6
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Classifications
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- 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
-
- 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
- C07F9/6536—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and sulfur atoms with or without oxygen atoms, as the only ring hetero atoms
- C07F9/6539—Five-membered rings
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
-
- 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
- C07F9/576—Six-membered rings
- C07F9/58—Pyridine rings
-
- 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
- C07F9/576—Six-membered rings
- C07F9/60—Quinoline or hydrogenated quinoline ring systems
-
- 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
- C07F9/576—Six-membered rings
- C07F9/62—Isoquinoline or hydrogenated isoquinoline ring systems
-
- 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
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6503—Five-membered rings
- C07F9/6506—Five-membered rings having the nitrogen atoms in positions 1 and 3
-
- 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
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6509—Six-membered rings
- C07F9/650905—Six-membered rings having the nitrogen atoms in the positions 1 and 2
-
- 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
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6509—Six-membered rings
- C07F9/650952—Six-membered rings having the nitrogen atoms in the positions 1 and 4
-
- 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
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6509—Six-membered rings
- C07F9/6512—Six-membered rings having the nitrogen atoms in positions 1 and 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/286,193 US4983592A (en) | 1988-12-19 | 1988-12-19 | Bis-arylphosphate ester antagonists of platelet activating factor |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PH26906A true PH26906A (en) | 1992-12-03 |
Family
ID=23097500
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PH39725A PH26906A (en) | 1988-12-19 | 1989-12-18 | Bis-arylposphate ester antagonists of platelet activating factor |
Country Status (21)
| Country | Link |
|---|---|
| US (2) | US4983592A (fr) |
| EP (1) | EP0374513B1 (fr) |
| JP (1) | JP2733351B2 (fr) |
| KR (1) | KR0153279B1 (fr) |
| AR (1) | AR248027A1 (fr) |
| AT (1) | ATE132871T1 (fr) |
| AU (1) | AU623716B2 (fr) |
| CA (1) | CA2005678A1 (fr) |
| DE (1) | DE68925411T2 (fr) |
| DK (1) | DK170101B1 (fr) |
| ES (1) | ES2083964T3 (fr) |
| FI (1) | FI94348C (fr) |
| GR (1) | GR3018821T3 (fr) |
| IE (1) | IE74204B1 (fr) |
| IL (1) | IL92407A (fr) |
| MX (1) | MX9203270A (fr) |
| NO (1) | NO178305C (fr) |
| NZ (1) | NZ231724A (fr) |
| PH (1) | PH26906A (fr) |
| PT (1) | PT92595B (fr) |
| ZA (1) | ZA899695B (fr) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5234918A (en) * | 1988-04-04 | 1993-08-10 | American Cyanamid Company | Certain phosphinyl-oxy-phenyl-methyl-pyridinium-hydroxide inner salts useful as antagonists of PAF |
| US5215975A (en) * | 1988-04-04 | 1993-06-01 | American Cyanamid Company | Certain hydroxy-phosphinyl-oxy-phenyl methyl-thiazolium hydroxide inner salts as PAF antagonists |
| US5147864A (en) * | 1988-12-19 | 1992-09-15 | American Cyanamid Company | Bis-arylphosphate ester antagonists of platelet activating factor |
| US5231091A (en) * | 1988-12-19 | 1993-07-27 | American Cyanamid Company | Bis-arylphosphate ester antagonists of platelet activating factor |
| US4983592A (en) * | 1988-12-19 | 1991-01-08 | American Cyanamid Co. | Bis-arylphosphate ester antagonists of platelet activating factor |
| US5496855A (en) * | 1995-01-27 | 1996-03-05 | Smithkline Beecham Corp. | Anti-inflammatory compounds |
| FR2880887B1 (fr) * | 2005-01-14 | 2009-01-30 | Merck Sante Soc Par Actions Si | Derives d'hydroxyphenols, procedes pour leur preparation, compositions pharmaceutiques les contenant et applications en therapeutique |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7612668A (nl) * | 1976-01-06 | 1977-07-08 | Dow Chemical Co | Werkwijze voor het bereiden van nieuwe organo- fosforusverbindingen. |
| US4091095A (en) * | 1976-07-06 | 1978-05-23 | Hoechst Aktiengesellschaft | Phosphinyl compounds |
| US4316896A (en) * | 1978-09-07 | 1982-02-23 | Merck & Co., Inc. | Aminoacid derivatives as antihypertensives |
| US4456464A (en) * | 1982-05-19 | 1984-06-26 | Zoecon Corporation | Phenoxy- and pyridyloxy-phenoxyalkyl phosphinates and related sulfur compounds for weed control |
| JPS5984824A (ja) * | 1982-11-08 | 1984-05-16 | Takeda Chem Ind Ltd | 抗腫瘍剤 |
| US4640913A (en) * | 1983-01-10 | 1987-02-03 | American Cyanamid Company | Phosphocholine derivatives having antihypertensive action |
| US4650791A (en) * | 1984-01-11 | 1987-03-17 | Takedo Chemical Industries, Ltd. | Certain 3-alkoxy-2-cyclic-imido-propyl-phosphate-ethyl-cyclic ammonium hydroxide inner salts which inhibit activities of platelet activating factor |
| EP0178261A3 (fr) * | 1984-10-10 | 1986-12-30 | Sandoz Ag | Sels de cyclimmonium substitués de 2-furanyl ou 5-oxo-2-furanyl-alkoxy-phosphoryl-alkyle |
| US4710579A (en) * | 1984-11-09 | 1987-12-01 | Takeda Chemical Industries, Ltd. | 2-(acetoacetyloxy)-3-(octadecyloxy)propyl-3-trimethylammoniopropyl phosphate or a pharmaceutically acceptable salt thereof |
| IT1178709B (it) * | 1984-12-05 | 1987-09-16 | Neopharmed Spa | Diacilderivati della glicerilfosforilcolina ad attivita'terapeutica, procedimento per la loro preparazione e relative composizioni farmaceutiche |
| US4762942A (en) * | 1984-12-10 | 1988-08-09 | American Cyanamid Co. | Antihypertensive phosphate derivatives |
| US4900731A (en) * | 1984-12-10 | 1990-02-13 | American Cyanamid Company | Antihypertensive phosphate derivatives |
| US4827011A (en) * | 1984-12-10 | 1989-05-02 | American Cyanamid Company | Antihypertensive phosphate derivatives |
| DE3663522D1 (en) * | 1985-11-29 | 1989-06-29 | Takeda Chemical Industries Ltd | Phospholipid derivatives, their production and use |
| DE3626058A1 (de) * | 1986-08-01 | 1988-02-11 | Boehringer Mannheim Gmbh | Neue diphosphonsaeurederivate, verfahren zu deren herstellung und diese verbindungen enthaltende arzneimittel |
| DE68927671T2 (de) * | 1988-12-19 | 1997-05-07 | American Cyanamid Co | Produkte zur Behandlung des Endotoxin -Schocks bei einem Säugetier |
| US4983592A (en) * | 1988-12-19 | 1991-01-08 | American Cyanamid Co. | Bis-arylphosphate ester antagonists of platelet activating factor |
| US5208223A (en) * | 1990-11-13 | 1993-05-04 | American Cyanamid Company | Phosphocholine derivative inhibitors of phospholipase A2 |
-
1988
- 1988-12-19 US US07/286,193 patent/US4983592A/en not_active Expired - Fee Related
-
1989
- 1989-11-23 IL IL9240789A patent/IL92407A/en not_active IP Right Cessation
- 1989-11-23 ES ES89121680T patent/ES2083964T3/es not_active Expired - Lifetime
- 1989-11-23 EP EP89121680A patent/EP0374513B1/fr not_active Expired - Lifetime
- 1989-11-23 AT AT89121680T patent/ATE132871T1/de not_active IP Right Cessation
- 1989-11-23 DE DE68925411T patent/DE68925411T2/de not_active Expired - Fee Related
- 1989-12-12 NZ NZ231724A patent/NZ231724A/en unknown
- 1989-12-15 PT PT92595A patent/PT92595B/pt not_active IP Right Cessation
- 1989-12-15 CA CA002005678A patent/CA2005678A1/fr not_active Abandoned
- 1989-12-18 PH PH39725A patent/PH26906A/en unknown
- 1989-12-18 AU AU46883/89A patent/AU623716B2/en not_active Ceased
- 1989-12-18 NO NO895085A patent/NO178305C/no unknown
- 1989-12-18 DK DK641989A patent/DK170101B1/da not_active IP Right Cessation
- 1989-12-18 FI FI896045A patent/FI94348C/fi not_active IP Right Cessation
- 1989-12-18 KR KR1019890018798A patent/KR0153279B1/ko not_active IP Right Cessation
- 1989-12-18 ZA ZA899695A patent/ZA899695B/xx unknown
- 1989-12-18 IE IE405889A patent/IE74204B1/en not_active IP Right Cessation
- 1989-12-18 AR AR89315708A patent/AR248027A1/es active
- 1989-12-19 JP JP1329433A patent/JP2733351B2/ja not_active Expired - Lifetime
-
1992
- 1992-06-24 MX MX9203270A patent/MX9203270A/es unknown
-
1993
- 1993-06-01 US US08/069,638 patent/US5328901A/en not_active Expired - Lifetime
-
1996
- 1996-01-31 GR GR950402383T patent/GR3018821T3/el unknown
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