KR900011728A - 5-리폭시게나제 억제제로서의 치환된 인돌, 벤조푸란 및 벤조티오펜 유도체 - Google Patents
5-리폭시게나제 억제제로서의 치환된 인돌, 벤조푸란 및 벤조티오펜 유도체 Download PDFInfo
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- KR900011728A KR900011728A KR1019900000037A KR900000037A KR900011728A KR 900011728 A KR900011728 A KR 900011728A KR 1019900000037 A KR1019900000037 A KR 1019900000037A KR 900000037 A KR900000037 A KR 900000037A KR 900011728 A KR900011728 A KR 900011728A
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- Prior art keywords
- compound
- mammal
- lipoxygenase
- administering
- inhibiting
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- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical class C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 title 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical class C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 title 1
- 239000000867 Lipoxygenase Inhibitor Substances 0.000 title 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 title 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 title 1
- 150000002475 indoles Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 27
- 102000001381 Arachidonate 5-Lipoxygenase Human genes 0.000 claims 14
- 108010093579 Arachidonate 5-lipoxygenase Proteins 0.000 claims 14
- 241000124008 Mammalia Species 0.000 claims 14
- 230000002401 inhibitory effect Effects 0.000 claims 14
- 239000003937 drug carrier Substances 0.000 claims 7
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- 238000000034 method Methods 0.000 claims 7
- 239000008194 pharmaceutical composition Substances 0.000 claims 7
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- -1 3,4-methylenedioxyphenyl Chemical group 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 150000003018 phosphorus compounds Chemical class 0.000 claims 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 1
- VIEZWYFEIKZIJD-UHFFFAOYSA-N 5-benzyl-1-methylindol-4-ol Chemical compound C=1C=C2N(C)C=CC2=C(O)C=1CC1=CC=CC=C1 VIEZWYFEIKZIJD-UHFFFAOYSA-N 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 150000008064 anhydrides Chemical class 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000004001 thioalkyl group Chemical group 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- 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
- C07D401/06—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 carbon chain containing only aliphatic carbon atoms
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Furan Compounds (AREA)
- Detergent Compositions (AREA)
- Fats And Perfumes (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (22)
- 다음 일반식(I)의 화합물.(I)상기식에서, X는 O,S 또는 NR1(여기서 R1은 수소, 탄소수 1내지 4의 알킬 또는 벤질이다)이고, R2는 수소또는 C(=O)R4(여기서, R4는 탄소수 1내지 4의 알킬 또는 알콕시이다)이며, R3은 피리딜, 3,4-메틸렌디옥시페닐, O,S,N 및 NR8(여기서, R8은 수소 또는 탄소수 1내지 4의 알킬이다)로 부터 독립적으로 선택된 1 또는 2개의 헤테로 원자를 갖는 방향족 5원 헤테로 사이클릭 환(단, 헤테로원자가 2개 존재하면 하나는 반드시 N이고, 헤테로원자가 1개만 존재하면 N일 수 없다)또는 각각 F,Cl,Br 탄소수 1내지 4의 알킬, 탄소수 1내지 4의 알콕시, 탄소수 1내지 4의 티오알킬, 탄소수 1내지 4의 알킬설포닐 및 NR6 R7(여기서, R6 및 R7은 독립적으로 수소 또는 탄소수 1내지 4의 알킬이거나, 함께-(CH2)4-이다)로부터 선택된 1내지 3개의 그룹에 의해 임의로 치환된 페닐이다.
- 제1항에 있어서, X가 NR1인 화합물.
- 제1항에 있어서, R3이 페닐인 화합물.
- 제1항에 있어서, R2가 수소 또는인 화합물.
- 제1항에 있어서, X가 NR1이고 R3이 페닐이며 R2가 수소 또는인 화합물.
- 제1항에 있어서, 1-메틸-4-하이드록시-5-페닐메틸인돌인 화합물.
- 제1항에 있어서, 1-메틸-4-아세톡시-5-페닐메틸인돌일 화합물.
- 약제학적으로 허용되는 담체와 5-리폭시게나제 억제량의 제1항의 화합물로 필수적으로 이루어진 약제학적 조성물.
- 약제학적으로 허용되는 담체와 5-리폭시게나제 억제량의 제2항의 화합물로 필수적으로 이루어진 약제학적 조성물.
- 약제학적으로 허용되는 담체와 5-리폭시게나제 억제량의 제3항의 화합물로 필수적으로 이루어진 약제학적 조성물.
- 약제학적으로 허용되는 담체와 5-리폭시게나제 억제량의 제4항의 화합물로 필수적으로 이루어진 약제학적 조성물.
- 약제학적으로 허용되는 담체와 5-리폭시게나제 억제량의 제5항의 화합물로 필수적으로 이루어진 약제학적 조성물.
- 약제학적으로 허용되는 담체와 5-리폭시게나제 억제량의 제6항의 화합물로 필수적으로 이루어진 약제학적 조성물.
- 약제학적으로 허용되는 담체와 5-리폭시게나제 억제량의 제7항의 화합물로 필수적으로 이루어진 약제학적 조성물.
- 제1항의 화합물 유효량을 포유동물에게 투여함을 특징으로 하여 포유동물에서 5-리폭시게나제를 억제하는 방법.
- 제2항의 화합물 유효량을 포유동물에게 투여함을 특징으로 하여 포유동물에서 5-리폭시게나제를 억제하는 방법.
- 제3항의 화합물 유효량을 포유동물에게 투여함을 특징으로 하여 포유동물에서 5-리폭시게나제를 억제하는 방법.
- 제4항의 화합물 유효량을 포유동물에게 투여함을 특징으로 하여 포유동물에서 5-리폭시게나제를 억제하는 방법.
- 제5항의 화합물 유효량을 포유동물에게 투여함을 특징으로 하여 포유동물에서 5-리폭시게나제를 억제하는 방법.
- 제6항의 화합물 유효량을 포유동물에게 투여함을 특징으로 하여 포유동물에서 5-리폭시게나제를 억제하는 방법.
- 제7항의 화합물 유효량을 포유동물에게 투여함을 특징으로 하여 포유동물에서 5-리폭시게나제를 억제하는 방법.
- a) 일반식(Ⅱ)의 화합물을 염기의 존재하에 용액속에서 일반식 R3CHO의 알데하이드(여기서, R3은 제1항에서 정의한 바와 같다)와 반응시키고, b)생성된 화합물을 산성화시켜 일반식(Ia)의 화합물을 수득하고 임의로, c)단계 b)에서 수득한 화합물을 일반식 R4COCl의 산 클로라이드 또는 일반식(R4CO)2O의 무수물(여기서, R4는 제1항에서 정의한 바와 같다)과 반응시켜 일반식(Id)의 화합물을 수득함을 포함하여 제1항의 화합물을제조하는 방법.(Ⅱ)(Ia)(Id)상기식에서, X는 O,S 또는 NR1(여기서, R1은 수소가 아니다)이고, R3 및 R4는 제1항에서 정의한 바와 같다.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US293,522 | 1989-01-05 | ||
| US07/293,522 US5093351A (en) | 1989-01-05 | 1989-01-05 | Substituted indole, benzofuran and benzothiophene derivatives as 5-lipoxygenase inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR900011728A true KR900011728A (ko) | 1990-08-02 |
| KR910009936B1 KR910009936B1 (ko) | 1991-12-06 |
Family
ID=23129426
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019900000037A KR910009936B1 (ko) | 1989-01-05 | 1990-01-04 | 5-리폭시게나제 억제제로서의 치환된 인돌, 벤조푸란 및 벤조티오펜 유도체 |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US5093351A (ko) |
| EP (1) | EP0377450B1 (ko) |
| JP (1) | JPH0667924B2 (ko) |
| KR (1) | KR910009936B1 (ko) |
| AT (1) | ATE109133T1 (ko) |
| AU (1) | AU628121B2 (ko) |
| CA (1) | CA2006201C (ko) |
| DE (1) | DE69010921T2 (ko) |
| DK (1) | DK0377450T3 (ko) |
| ES (1) | ES2060818T3 (ko) |
| FI (1) | FI900041A (ko) |
| HU (1) | HUT53073A (ko) |
| IL (1) | IL92971A (ko) |
| NO (1) | NO174345C (ko) |
| NZ (1) | NZ232000A (ko) |
| PT (1) | PT92785A (ko) |
| RU (1) | RU1799379C (ko) |
| ZA (1) | ZA9093B (ko) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5091379A (en) * | 1989-08-31 | 1992-02-25 | Du Pont Merck Pharmaceutical Company | Topical antinflammatory compositions with minimal systemic absorption |
| GB8925515D0 (en) * | 1989-11-10 | 1989-12-28 | Unilever Plc | Method of extraction |
| CA2134192A1 (en) * | 1993-11-12 | 1995-05-13 | Michael L. Denney | 5, 6-bicyclic glycoprotein iib/iiia antagonists |
| US5532382A (en) * | 1995-03-13 | 1996-07-02 | Eli Lilly And Company | Benzothiophenes substituted at the 3-carbonyl |
| US5514704A (en) * | 1995-03-13 | 1996-05-07 | Eli Lilly And Company | Benzothiophenes to inhibit leukotrienes |
| US5514703A (en) * | 1995-03-13 | 1996-05-07 | Eli Lilly And Company | Benzothiophene compounds useful for inhibiting lipoxygenase |
| US6071949A (en) * | 1995-03-14 | 2000-06-06 | The United States Of America As Represented By The Department Of Health And Human Services | Use of lipoxygenase inhibitors as anti-cancer therapeutic and intervention agents |
| FR2742047B1 (fr) | 1995-12-06 | 1998-01-16 | Oreal | Compositions de teinture des fibres keratiniques contenant des derives n-substitues de la 4-hydroxy indoline, nouveaux derives, leur procede de synthese, leur utilisation pour la teinture, et procede de teinture |
| US5711958A (en) * | 1996-07-11 | 1998-01-27 | Life Medical Sciences, Inc. | Methods for reducing or eliminating post-surgical adhesion formation |
| US6696499B1 (en) * | 1996-07-11 | 2004-02-24 | Life Medical Sciences, Inc. | Methods and compositions for reducing or eliminating post-surgical adhesion formation |
| US6211249B1 (en) | 1997-07-11 | 2001-04-03 | Life Medical Sciences, Inc. | Polyester polyether block copolymers |
| AU3053199A (en) | 1998-04-01 | 1999-10-25 | Ono Pharmaceutical Co. Ltd. | Fused thiophene derivatives and drugs containing the same as the active ingredient |
| FR2806721B1 (fr) * | 2000-03-24 | 2002-05-03 | Oreal | Procede de preparation de composes 3-(4-hydroxy-1h-undol-5- ylmethyl)-pyridiniums passant par des enones |
| FR2807040B1 (fr) * | 2000-03-31 | 2002-05-17 | Oreal | Procede de preparation de composes 3-(4-hydroxy-1h-indol-5- ylmethyl)-pyridiniums utilisant une reaction d'aldolisation |
| JP2004517851A (ja) | 2000-12-27 | 2004-06-17 | バイエル アクチェンゲゼルシャフト | 甲状腺受容体のリガンドとしてのインドール誘導体 |
| AU2004230369B2 (en) | 2003-04-14 | 2008-01-10 | Nippon Soda Co., Ltd | Diamine derivative, production process, and antioxidizing drug |
| US20080306148A1 (en) * | 2007-04-13 | 2008-12-11 | The Penn State Research Foundation | Anti-cancer compositions and methods |
| US8003633B1 (en) | 2008-04-14 | 2011-08-23 | The Penn State Research Foundation | Anti-cancer compositions and methods |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1211030A (en) * | 1967-11-15 | 1970-11-04 | Sandoz Ltd | Novel indole derivatives and process for their production |
| US4428962A (en) * | 1981-10-30 | 1984-01-31 | Schering Corporation | Indoles in treatment of peptic ulcers |
| US4663347A (en) * | 1983-10-31 | 1987-05-05 | Merck Frosst Canada, Inc. | Benzofuran 2-carboxylic acid esters useful as inhibitors of leukotriene biosynthesis |
| US4737519A (en) * | 1983-12-14 | 1988-04-12 | The Upjohn Company | Substituted naphthalenes, indoles, benzofurans, and benzothiophenes as lipoxygenase inhibitors |
| CA1281325C (en) * | 1984-06-20 | 1991-03-12 | Patrice C. Belanger | Benzofuran derivatives |
| CA1241660A (en) * | 1984-06-25 | 1988-09-06 | Yvan Guindon | Indole-2-alkanoic acids |
| IE58555B1 (en) * | 1984-12-10 | 1993-10-06 | Warner Almbert Company | Novel benzothiophenes and benzofurans having antiallergy activity |
| JP2551070B2 (ja) * | 1987-12-28 | 1996-11-06 | いすゞ自動車株式会社 | 真空ダイカスト装置における安全弁 |
| EP0398413A1 (en) * | 1989-05-16 | 1990-11-22 | Duphar International Research B.V | "3,4-dehydropiperidine derivatives having psychotropic activity |
| FR2654336B1 (fr) * | 1989-11-10 | 1994-06-03 | Oreal | Composition tinctoriale pour fibres keratiniques, contenant des precurseurs de colorants par oxydation et des coupleurs derives de 6- ou 7-hydroxyindole, et procede de teinture mettant en óoeuvre ces compositions. |
| GB8927277D0 (en) * | 1989-12-01 | 1990-01-31 | Glaxo Group Ltd | Chemical compounds |
-
1989
- 1989-01-05 US US07/293,522 patent/US5093351A/en not_active Expired - Lifetime
- 1989-12-20 CA CA002006201A patent/CA2006201C/en not_active Expired - Fee Related
- 1989-12-29 RU SU894742832A patent/RU1799379C/ru active
- 1989-12-29 HU HU896825A patent/HUT53073A/hu unknown
-
1990
- 1990-01-03 AT AT90100085T patent/ATE109133T1/de not_active IP Right Cessation
- 1990-01-03 DK DK90100085.1T patent/DK0377450T3/da active
- 1990-01-03 DE DE69010921T patent/DE69010921T2/de not_active Expired - Fee Related
- 1990-01-03 ES ES90100085T patent/ES2060818T3/es not_active Expired - Lifetime
- 1990-01-03 EP EP90100085A patent/EP0377450B1/en not_active Expired - Lifetime
- 1990-01-04 NZ NZ232000A patent/NZ232000A/en unknown
- 1990-01-04 PT PT92785A patent/PT92785A/pt not_active Application Discontinuation
- 1990-01-04 FI FI900041A patent/FI900041A/fi not_active Application Discontinuation
- 1990-01-04 IL IL92971A patent/IL92971A/xx not_active IP Right Cessation
- 1990-01-04 KR KR1019900000037A patent/KR910009936B1/ko not_active IP Right Cessation
- 1990-01-04 NO NO900022A patent/NO174345C/no not_active IP Right Cessation
- 1990-01-05 JP JP2000143A patent/JPH0667924B2/ja not_active Expired - Lifetime
- 1990-01-05 AU AU47694/90A patent/AU628121B2/en not_active Ceased
- 1990-01-05 ZA ZA9093A patent/ZA9093B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HUT53073A (en) | 1990-09-28 |
| EP0377450B1 (en) | 1994-07-27 |
| HU896825D0 (en) | 1990-03-28 |
| FI900041A (fi) | 1990-07-06 |
| NZ232000A (en) | 1991-03-26 |
| CA2006201A1 (en) | 1990-07-05 |
| DK0377450T3 (da) | 1994-11-28 |
| JPH02288856A (ja) | 1990-11-28 |
| ZA9093B (en) | 1991-09-25 |
| US5093351A (en) | 1992-03-03 |
| IL92971A (en) | 1993-07-08 |
| RU1799379C (ru) | 1993-02-28 |
| PT92785A (pt) | 1990-07-31 |
| ES2060818T3 (es) | 1994-12-01 |
| CA2006201C (en) | 1998-11-10 |
| AU4769490A (en) | 1990-07-12 |
| EP0377450A1 (en) | 1990-07-11 |
| NO174345C (no) | 1994-04-20 |
| ATE109133T1 (de) | 1994-08-15 |
| NO900022D0 (no) | 1990-01-04 |
| NO174345B (no) | 1994-01-10 |
| DE69010921T2 (de) | 1995-03-09 |
| DE69010921D1 (de) | 1994-09-01 |
| IL92971A0 (en) | 1990-09-17 |
| AU628121B2 (en) | 1992-09-10 |
| FI900041A0 (fi) | 1990-01-04 |
| KR910009936B1 (ko) | 1991-12-06 |
| NO900022L (no) | 1990-07-06 |
| JPH0667924B2 (ja) | 1994-08-31 |
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| LAPS | Lapse due to unpaid annual fee |