IL96260A - Pharmaceutical preparations containing derivatives and analogues of pyrimidone for the short-term treatment of skin diseases and infections - Google Patents
Pharmaceutical preparations containing derivatives and analogues of pyrimidone for the short-term treatment of skin diseases and infectionsInfo
- Publication number
- IL96260A IL96260A IL9626090A IL9626090A IL96260A IL 96260 A IL96260 A IL 96260A IL 9626090 A IL9626090 A IL 9626090A IL 9626090 A IL9626090 A IL 9626090A IL 96260 A IL96260 A IL 96260A
- Authority
- IL
- Israel
- Prior art keywords
- treatment
- asthma
- pharmaceutical composition
- bicyclo
- hept
- Prior art date
Links
- 208000006673 asthma Diseases 0.000 title claims abstract description 16
- 230000002757 inflammatory effect Effects 0.000 title claims abstract description 9
- 208000017520 skin disease Diseases 0.000 title claims abstract description 7
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 14
- 150000008318 pyrimidones Chemical class 0.000 title description 2
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 35
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 7
- 208000023504 respiratory system disease Diseases 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 125000005592 polycycloalkyl group Polymers 0.000 claims abstract description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 3
- 125000001589 carboacyl group Chemical group 0.000 claims abstract description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 3
- -1 (C2-C3) alkeny 1 Chemical group 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 8
- 201000004624 Dermatitis Diseases 0.000 claims description 7
- 206010012438 Dermatitis atopic Diseases 0.000 claims description 7
- 201000008937 atopic dermatitis Diseases 0.000 claims description 7
- 201000004681 Psoriasis Diseases 0.000 claims description 5
- 208000023819 chronic asthma Diseases 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 208000037883 airway inflammation Diseases 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 abstract description 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract description 3
- 125000006592 (C2-C3) alkenyl group Chemical group 0.000 abstract description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 abstract description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
- 241000700198 Cavia Species 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 description 10
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 229940092253 ovalbumin Drugs 0.000 description 8
- 108010058846 Ovalbumin Proteins 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 210000004072 lung Anatomy 0.000 description 6
- YBYRMVIVWMBXKQ-UHFFFAOYSA-N phenylmethanesulfonyl fluoride Chemical compound FS(=O)(=O)CC1=CC=CC=C1 YBYRMVIVWMBXKQ-UHFFFAOYSA-N 0.000 description 6
- 210000001519 tissue Anatomy 0.000 description 6
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- 230000000704 physical effect Effects 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 239000011534 wash buffer Substances 0.000 description 3
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- 208000035285 Allergic Seasonal Rhinitis Diseases 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- 241000700199 Cavia porcellus Species 0.000 description 2
- IVOMOUWHDPKRLL-KQYNXXCUSA-N Cyclic adenosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- 101000841267 Homo sapiens Long chain 3-hydroxyacyl-CoA dehydrogenase Proteins 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 102100029107 Long chain 3-hydroxyacyl-CoA dehydrogenase Human genes 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- 229940099471 Phosphodiesterase inhibitor Drugs 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
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- RIIWUGSYXOBDMC-UHFFFAOYSA-N benzene-1,2-diamine;hydron;dichloride Chemical compound Cl.Cl.NC1=CC=CC=C1N RIIWUGSYXOBDMC-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
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- YECBIJXISLIIDS-UHFFFAOYSA-N mepyramine Chemical compound C1=CC(OC)=CC=C1CN(CCN(C)C)C1=CC=CC=N1 YECBIJXISLIIDS-UHFFFAOYSA-N 0.000 description 2
- 229960000582 mepyramine Drugs 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
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- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
- 229920000053 polysorbate 80 Polymers 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
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- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 230000009885 systemic effect Effects 0.000 description 2
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- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
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- JJYKJUXBWFATTE-VIFPVBQESA-N (2s)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoic acid Chemical compound CO[C@@](C(O)=O)(C(F)(F)F)C1=CC=CC=C1 JJYKJUXBWFATTE-VIFPVBQESA-N 0.000 description 1
- WRMIVVLGWCQXNE-UHFFFAOYSA-N 2,2,2-trichloroethyl butanoate Chemical compound CCCC(=O)OCC(Cl)(Cl)Cl WRMIVVLGWCQXNE-UHFFFAOYSA-N 0.000 description 1
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- PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical compound NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 description 1
- OWMVSZAMULFTJU-UHFFFAOYSA-N bis-tris Chemical compound OCCN(CCO)C(CO)(CO)CO OWMVSZAMULFTJU-UHFFFAOYSA-N 0.000 description 1
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- ZTOMUSMDRMJOTH-UHFFFAOYSA-N glutaronitrile Chemical compound N#CCCCC#N ZTOMUSMDRMJOTH-UHFFFAOYSA-N 0.000 description 1
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- ACKFDYCQCBEDNU-UHFFFAOYSA-J lead(2+);tetraacetate Chemical compound [Pb+2].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O ACKFDYCQCBEDNU-UHFFFAOYSA-J 0.000 description 1
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- JJYKJUXBWFATTE-UHFFFAOYSA-N mosher's acid Chemical compound COC(C(O)=O)(C(F)(F)F)C1=CC=CC=C1 JJYKJUXBWFATTE-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- RCCYSVYHULFYHE-UHFFFAOYSA-N pentanediamide Chemical compound NC(=O)CCCC(N)=O RCCYSVYHULFYHE-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
-
- 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
-
- 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
- A61P11/08—Bronchodilators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- 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
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/US1989/005221 WO1991007177A1 (en) | 1989-11-13 | 1989-11-13 | Pyrimidone derivatives and analogs in the treatment of asthma or certain skin disorders |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL96260A0 IL96260A0 (en) | 1991-08-16 |
| IL96260A true IL96260A (en) | 1995-11-27 |
Family
ID=22215372
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL9626090A IL96260A (en) | 1989-11-13 | 1990-11-06 | Pharmaceutical preparations containing derivatives and analogues of pyrimidone for the short-term treatment of skin diseases and infections |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US5342842A (de) |
| EP (1) | EP0428313B1 (de) |
| JP (2) | JPH0662412B2 (de) |
| KR (1) | KR930001832B1 (de) |
| AT (1) | ATE101040T1 (de) |
| AU (1) | AU627631B2 (de) |
| CA (1) | CA2029704C (de) |
| DE (1) | DE69006452T2 (de) |
| DK (1) | DK0428313T3 (de) |
| HU (1) | HU212311B (de) |
| IE (1) | IE63472B1 (de) |
| IL (1) | IL96260A (de) |
| MY (1) | MY111474A (de) |
| NZ (1) | NZ236038A (de) |
| PT (1) | PT95854B (de) |
| WO (2) | WO1991007177A1 (de) |
| ZA (1) | ZA909043B (de) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PH31245A (en) * | 1991-10-30 | 1998-06-18 | Janssen Pharmaceutica Nv | 1,3-Dihydro-2H-imidazoÄ4,5-BÜ-quinolin-2-one derivatives. |
| EP0672031B1 (de) * | 1992-12-02 | 2003-03-12 | Pfizer Inc. | Cathecoldiether als selektive pde iv hemmungsmittel |
| US5814651A (en) * | 1992-12-02 | 1998-09-29 | Pfizer Inc. | Catechol diethers as selective PDEIV inhibitors |
| US5482944A (en) * | 1993-07-13 | 1996-01-09 | Pfizer Inc. | Pyrimidones and imidazolinones for treatment of shock |
| US5502072A (en) * | 1993-11-26 | 1996-03-26 | Pfizer Inc. | Substituted oxindoles |
| US5686434A (en) * | 1993-11-26 | 1997-11-11 | Pfizer Inc. | 3-aryl-2-isoxazolines as antiinflammatory agents |
| CA2184914C (en) * | 1994-03-09 | 2000-09-19 | Victoria L. Cohan | Isoxazoline compounds as 5-lipoxygenase inhibitors |
| EP0749428B1 (de) * | 1994-03-09 | 1998-07-29 | Pfizer Inc. | Isoxazoline verbindung zur hemmung tnf-freigabe |
| US5563143A (en) * | 1994-09-21 | 1996-10-08 | Pfizer Inc. | Catechol diether compounds as inhibitors of TNF release |
| WO1997048697A1 (en) | 1996-06-19 | 1997-12-24 | Rhone-Poulenc Rorer Limited | Substituted azabicylic compounds and their use as inhibitors of the production of tnf and cyclic amp phosphodiesterase |
| US6265402B1 (en) | 1996-08-27 | 2001-07-24 | Nikken Chemicals Co., Ltd. | Use of 2-phenylmorpholin-5-one derivatives |
| US6555572B2 (en) * | 2000-03-16 | 2003-04-29 | Inflazyme Pharmaceuticals Ltd. | Benzylated PDE4 inhibitors |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2401446A1 (de) * | 1973-01-16 | 1974-07-25 | Voorhees | Pharmazeutische zubereitungen zur linderung von hautproliferationserkrankungen |
| SU888821A3 (ru) * | 1976-12-03 | 1981-12-07 | Шеринг Аг (Инофирма) | Способ получени 5-(замещенный фенил)-оксазолидинонов или их серусодержащих аналогов |
| DE3315797A1 (de) * | 1983-04-30 | 1984-10-31 | Beiersdorf Ag, 2000 Hamburg | Substituierte phenyl-2-(1h)-pyrimidinone, verfahren zu ihrer herstellung und ihre verwendung sowie diese verbindungen enthaltende zubereitungen |
| GB8416140D0 (en) * | 1984-06-25 | 1984-08-01 | Fujisawa Pharmaceutical Co | Pyrimidinone derivatives |
| WO1987006576A1 (en) * | 1986-04-29 | 1987-11-05 | Pfizer Inc. | Calcium independent camp phosphodiesterase inhibitor antidepressant |
-
1989
- 1989-11-13 WO PCT/US1989/005221 patent/WO1991007177A1/en not_active Ceased
-
1990
- 1990-04-20 HU HU9201575A patent/HU212311B/hu not_active IP Right Cessation
- 1990-04-20 WO PCT/US1990/002162 patent/WO1991007178A1/en not_active Ceased
- 1990-04-20 US US07/855,046 patent/US5342842A/en not_active Expired - Fee Related
- 1990-11-06 EP EP90312117A patent/EP0428313B1/de not_active Expired - Lifetime
- 1990-11-06 IL IL9626090A patent/IL96260A/en active IP Right Grant
- 1990-11-06 AT AT90312117T patent/ATE101040T1/de not_active IP Right Cessation
- 1990-11-06 DE DE90312117T patent/DE69006452T2/de not_active Expired - Fee Related
- 1990-11-06 DK DK90312117.6T patent/DK0428313T3/da active
- 1990-11-09 MY MYPI90001979A patent/MY111474A/en unknown
- 1990-11-09 CA CA002029704A patent/CA2029704C/en not_active Expired - Fee Related
- 1990-11-12 NZ NZ236038A patent/NZ236038A/en unknown
- 1990-11-12 ZA ZA909043A patent/ZA909043B/xx unknown
- 1990-11-12 AU AU66536/90A patent/AU627631B2/en not_active Ceased
- 1990-11-12 PT PT95854A patent/PT95854B/pt not_active IP Right Cessation
- 1990-11-12 KR KR1019900018241A patent/KR930001832B1/ko not_active Expired - Fee Related
- 1990-11-12 IE IE405890A patent/IE63472B1/en not_active IP Right Cessation
- 1990-11-13 JP JP2306973A patent/JPH0662412B2/ja not_active Expired - Fee Related
-
1994
- 1994-02-03 JP JP6011680A patent/JP2514163B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| IE904058A1 (en) | 1991-05-22 |
| EP0428313A2 (de) | 1991-05-22 |
| CA2029704C (en) | 1995-02-07 |
| PT95854A (pt) | 1991-09-13 |
| HUT70052A (en) | 1995-09-28 |
| AU627631B2 (en) | 1992-08-27 |
| CA2029704A1 (en) | 1991-05-14 |
| DE69006452D1 (de) | 1994-03-17 |
| JPH03209322A (ja) | 1991-09-12 |
| JP2514163B2 (ja) | 1996-07-10 |
| NZ236038A (en) | 1997-03-24 |
| IL96260A0 (en) | 1991-08-16 |
| HU9201575D0 (en) | 1993-04-28 |
| WO1991007177A1 (en) | 1991-05-30 |
| PT95854B (pt) | 1997-11-28 |
| KR910009259A (ko) | 1991-06-28 |
| IE63472B1 (en) | 1995-04-19 |
| KR930001832B1 (ko) | 1993-03-15 |
| US5342842A (en) | 1994-08-30 |
| MY111474A (en) | 2000-06-30 |
| ZA909043B (en) | 1992-06-24 |
| EP0428313A3 (en) | 1991-11-06 |
| DE69006452T2 (de) | 1994-05-11 |
| AU6653690A (en) | 1991-08-01 |
| HU212311B (en) | 1996-05-28 |
| ATE101040T1 (de) | 1994-02-15 |
| JPH0748255A (ja) | 1995-02-21 |
| DK0428313T3 (da) | 1994-03-07 |
| WO1991007178A1 (en) | 1991-05-30 |
| JPH0662412B2 (ja) | 1994-08-17 |
| EP0428313B1 (de) | 1994-02-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FF | Patent granted | ||
| KB | Patent renewed | ||
| KB | Patent renewed |