KR900018034A - 치환 4-(퀴놀린-2-일-메톡시)페닐-아세트산 유도체 - Google Patents
치환 4-(퀴놀린-2-일-메톡시)페닐-아세트산 유도체 Download PDFInfo
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- KR900018034A KR900018034A KR1019890007229A KR890007229A KR900018034A KR 900018034 A KR900018034 A KR 900018034A KR 1019890007229 A KR1019890007229 A KR 1019890007229A KR 890007229 A KR890007229 A KR 890007229A KR 900018034 A KR900018034 A KR 900018034A
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- Prior art keywords
- hydrogen
- alkyl
- phenyl
- aryl
- formula
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- MYPFKEGUMKPGDR-UHFFFAOYSA-N 2-[4-(quinolin-2-ylmethoxy)phenyl]acetic acid Chemical class C1=CC(CC(=O)O)=CC=C1OCC1=CC=C(C=CC=C2)C2=N1 MYPFKEGUMKPGDR-UHFFFAOYSA-N 0.000 title claims 8
- 229910052739 hydrogen Inorganic materials 0.000 claims 27
- 239000001257 hydrogen Substances 0.000 claims 27
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 27
- 125000000217 alkyl group Chemical group 0.000 claims 24
- 125000003118 aryl group Chemical group 0.000 claims 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 8
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 6
- 239000002253 acid Substances 0.000 claims 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 4
- 125000004414 alkyl thio group Chemical group 0.000 claims 4
- 125000002837 carbocyclic group Chemical group 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 150000002148 esters Chemical class 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- -1 methylthio, ethylthio, propylthio, imidazolyl Chemical group 0.000 claims 4
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 4
- 238000000034 method Methods 0.000 claims 3
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 claims 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 230000007062 hydrolysis Effects 0.000 claims 2
- 238000006460 hydrolysis reaction Methods 0.000 claims 2
- 229940127557 pharmaceutical product Drugs 0.000 claims 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 230000032050 esterification Effects 0.000 claims 1
- 238000005886 esterification reaction Methods 0.000 claims 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 1
- 229910052740 iodine Chemical group 0.000 claims 1
- 239000011630 iodine Chemical group 0.000 claims 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 229940049953 phenylacetate Drugs 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D215/14—Radicals substituted by oxygen atoms
-
- 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
- A61P11/06—Antiasthmatics
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/18—Halogen atoms or nitro radicals
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Cardiology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicinal Preparation (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
내용 없음
Description
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Claims (10)
- 하기 일반식(I)의 치환 4-(퀴놀린-2-일-메톡시)페닐 아세트산 및 그의 염.상식 기중, R1은 구조식-OR2또는의 기[식중, R2및 R3은 동일하거나 상이한 것으로서 수소, 알킬, 아릴, 아랄킬 또는 하기 구조식(식중, R4는 수소, 알킬, 알랄킬 또는 아릴로서, 이 기들은 각각 히드록실, 카르복실, 알콕시카르보닐, 알킬티오, 헤테로아릴 또는 카르바모일에 의해 임의로 치환될 수 있고, R5은 수소, 알킬, 아릴 또는 아랄킬이고, R6는 구조식 -COR5또는 -CO2R5(식중, R는 정의한 바와 같음)의 기이고, R7은 수소, 알킬 또는 아릴임)의 기임]이고, Y는 하기 구조식(식중, R8은 수소, 알킬 또는 아릴이며, n은 0 내지 5의 수임)의 기이고, Z는 노르보르닐이거나 또는 하기 구조식(식중, R9및 R10은 동일하거나 상이한 것으로서, 수소, 알킬 또는 아릴이거나, 또는 R9및 R10은 함께 최대로 6개의 탄소원자를 갖는 포화카르보시클릭 고리를 형성하며, m은 1 내지 6의 수임)의 기이며 A 및 B는 동일하거나 상이한 것으로서, 수소, 저급 알킬 또는 할로겐이다.
- 제1항에 있어서, R1이 하기 구조식-OR2또는의 기[식중, R2및 R3은 동일하거나 상이한 것으로서 수소, 저급 알킬, 벤질, 페닐 또는 하기 구조식(식중, R4는 수소, 저급알킬, 페틸 또는 벤질로서, 이 기들은 각각 히드록실, 저급 알콕시카르보닐, 카르복실, 저급알킬티오, 헤테로아릴 또는 카르바모일에 의해 임의로 치환될 수 있고, R5은 수소, 저급 알킬, 페닐 또는 벤질이고, R6는 구조식 -COR5또는 -CO2R5(식중, R는 정의한 바와 같음)의 기이고, R7은 수소, 저급 알킬 또는 페닐임)의 기임]이고, Y는 하기 구조식(식중, R4은 수소, 저급 알킬 또는 페닐이며, n은 0 내지 5의 수임)의 기이고, Z는 노르보`르닐이거나 또는 하기 구조식(식중, R9및 R10은 동일하거나 상이한 것으로서, 수소, 저급 알킬 또는 페닐이거나, 또는 R9및 R10은 함께 최대로 6개의 탄소원자를 갖는 포화 카르보시클릭 고리이며, m은 1 내지 6의 수임)의 기이며 A 및 B는 동일하거나 상이한 것으로서, 수소, 메틸, 에틸, 불소, 염소 또는 브롬인 일반식 4-(퀴놀린-2-일-메톡시)페닐 아세트산 유도체 및 그의 염.
- 제1항에 있어서, R1이 하기 구조식-OR2또는의 기[식중, R2및 R3은 동일하거나 상이한 것으로서 수소, 메틸, 에틸, 프로필, 이소프로필, 부틸, 3급 부틸, 페닐 또는 벤질이거나, `또는 하기 구조식(식중, R4는 수소, 메틸, 에틸, 프로필, 이소프로필, 부틸, 3급-부틸, 벤질 또는 페닐로서 이 기들은 히드록실, 메톡시카르보닐, 에톡시카르보닐, 프로폭시카르보, 카르복실, 메틸티오, 에틸티오, 프로필티오, 이미다졸릴 또는 카르바모일에 의해 임의로 치환될 수 있고, R5은 수소, 메틸, 에틸, 프로필, 이소프로필, 부틸, 3급-부틸, 페닐 또는 벤질이고, R6는 하기 구조식 -COR5또는 -CO2R5(식중, R5는 정의한 바와 같음)의 기이고, R7은 수소, 메틸, 에틸, 프로필, 이소프로필, 부틸, 3급-부틸 또는 페닐임)의 기임]이고, Y는 하기 구조식(식중, R4은 수소, 메틸, 에틸, 프로필, 이소프로필, 3급-부틸 또는 페닐이며, n은 0 내지 5의 수임)의 기이고, Z는 노르보르닐이거나 또는 하기 구조식(식중, R9및 R10은 동일하거나 상이한 것으로서, 수소, 메틸, 에틸, n-프로필, 이소-프로필, 부틸 또는 3급-부틸 또는 페닐이거나, 또는 R9및 R10은 함께 최대로 6개의 탄소원자를 갖는 포화 카르보시클릭 고리를 형성하며, m은 1 내지 6의 수임)의 기이며 A 및 B는 동일하거나 상이한 것으로서, 수소, 메틸, 에틸, 불소 또는 염소인 일반식(I)의 치환 4-(퀴놀린-2-일-메톡시)페닐 아세트산 유도체 및 그의 염.
- 치료 처리용 제1 내지 3항에 의한 치환 4-(퀴놀린-2-일-메톡시)페닐 아세트산 유도체.
- [A] 하기 일반식(Ia)의 4-(퀴놀린-2-일-메톡시)페닐 아세트산에스테르를 하기 일반식(Ⅱ)의 화합물로 알킬화시키고, 산의 경우에 에스테르를 가수분해시키거나(상기식 중, R11은 알킬이며, A,B,Y 및 Z는 하기 정의하는 바와 같고, X는 염소, 브롬 또는 요오드임)[B] 하기 일반식(Ib)의 산을 하기 일반식(Ⅲ)의 화합물로 에스테르화하고, 산의 경우에 에스테르를 가수소분해 분열시키거나,[상기 식중, A,B,Y 및 Z는 하기 정의하는 바와 같고, R12는 하기 구조식(식중, R4'는 알킬, 알랄킬 또는 아릴로서, 이 기들은 히드록실, 카르복실, 알콕시카르보닐, 알킬티오, 헤테로아릴 또는 카르바모일에 의해 임의로 치환될 수 있고, R5'은 알킬, 아릴 또는 아랄킬이고, R6'는 구조식 -COR5'또는 -CO2R5'또는 -CO2R5(식중, R5'는 정의한 바와 같음)의 기이고, R7'은 알킬 또는 아릴임)의 기이고, X는 상기 정의한 바와 같음][C] 하기 일반식(Ib)의 산을 통상적인 활성화 시약존재하에 하기 일반식(Ⅳ)의 아민으로 아미드화하과, 산의 경우에 에스테르를 가수 분해시키거나,[상기 식중, R2및 R3는 하기 정의하는 바와 같되, 단 R2또는 R3가 기(식중, R 및 R는 하기 정의하는 바와 같음)인 경우 R는 수소가 아임][D]하기일반식(Ⅴ)의 페놀을 하기 일반식(Ⅵ)의 2-할로게노메틸퀴놀린으로 에테르화하며, 산의 경우에 에스테르를 가수 분해시킴을 특징으로 하는 하기일반식(I)의 치환 4-(퀴놀린-2-일-메톡시)페닐아세트산에스테르 유도체 및 그의 염의 제조방 염.(식중, R1은 구조식 -OR2또는의 기[R2및 R3은 동일하거나상이한 것으로서 수소, 알킬, 아릴, 아랄킬 또는 하기 구조식(식중, R4'는 알킬, 알랄킬 또는 아릴로서, 이 기들은 각각 히드록실, 카르복실, 알콕시카르보닐, 알킬티오, 헤테로아릴 또는 카르바모일에 의해 임의로 치환될 수 있고, R5'은 알킬, 아릴 또는 아랄킬이고, R6'는 구조식 -COR5'또는 -CO2R5'또는 -CO2R5(식중, R5'는 정의한 바와 같음)의 기이고, R7'은 수소, 알킬 또는 아릴임)의 기임]이고, Y는 하기 구조식(식중, R8은 수소, 알킬 또는 아릴이며, n은 0 내지 5의 수임)의 기이고, Z는 노르보르닐이거나 또는 하기 구조식(식중, R9및 R10은 동일하거나 상이한 것으로서, 수소, 알킬 또는 아릴이거나, 또는 R9및 R10은 함께 최대로 6개의 탄소원자를 갖는 포화 카르보시클릭 고리이며, m은 1 내지 6의 수임)의 기이며 A 및 B는 동일하거나 상이한 것으로서, 수소, 저급 알킬 또는 할로겐이다.
- 제5항에 있어서, 반응을 0°내지 150℃의 온도 범위에서 행함을 특징으로 하는 방법.
- 제1 내지 3항에 의한 치환 4-(퀴놀린-2-일-메톡시)페닐아세트산 유도체를 함유한 의약품.
- 제7항에 있어서, 치환 4-(퀴놀린-2-일-메톡시)페닐아세트산 유도체를 0.5 내지 90중량% 함유하는 의약품.
- 치환 4-(퀴놀린-2-일-메톡시)페닐아세트산 유도체의 질병 치료 용도.
- 치환 4-(퀴놀린-2-일-메톡시)페닐아세트산 유도체의 의약품 제조 용도.※ 참고사항 : 최초출원내용에 의하여 공개하는 것임.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP3818443.5 | 1988-05-31 | ||
| DEP38/8443.5 | 1988-05-31 | ||
| DE3818443 | 1988-05-31 | ||
| DEP3900261.6 | 1989-01-06 | ||
| DE3900261A DE3900261A1 (de) | 1988-05-31 | 1989-01-06 | Substituierte 4-(chinolin-2-yl-methoxy) phenyl-essigsaeure-derivate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR900018034A true KR900018034A (ko) | 1990-12-20 |
| KR0131202B1 KR0131202B1 (ko) | 1998-04-17 |
Family
ID=25868621
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019890007229A KR0131202B1 (ko) | 1988-05-31 | 1989-05-30 | 치환 4-(퀴놀린-2-일-메톡시)페닐-아세트산 유도체 |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4970215A (ko) |
| EP (1) | EP0344519B1 (ko) |
| JP (2) | JP2693576B2 (ko) |
| KR (1) | KR0131202B1 (ko) |
| CN (1) | CN1030251C (ko) |
| AT (1) | ATE88183T1 (ko) |
| AU (1) | AU616269B2 (ko) |
| CA (1) | CA1333802C (ko) |
| DE (2) | DE3900261A1 (ko) |
| DK (1) | DK169544B1 (ko) |
| ES (1) | ES2053864T3 (ko) |
| FI (1) | FI91635C (ko) |
| HK (1) | HK38895A (ko) |
| HU (2) | HU207719B (ko) |
| IE (1) | IE61922B1 (ko) |
| IL (1) | IL90435A (ko) |
| NO (1) | NO174889C (ko) |
| NZ (1) | NZ229310A (ko) |
| PT (1) | PT90675B (ko) |
| SG (1) | SG12795G (ko) |
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-
1989
- 1989-01-06 DE DE3900261A patent/DE3900261A1/de not_active Withdrawn
- 1989-05-15 CN CN89103512A patent/CN1030251C/zh not_active Expired - Lifetime
- 1989-05-16 NO NO891962A patent/NO174889C/no not_active IP Right Cessation
- 1989-05-18 DE DE8989108895T patent/DE58904042D1/de not_active Expired - Lifetime
- 1989-05-18 AT AT89108895T patent/ATE88183T1/de not_active IP Right Cessation
- 1989-05-18 ES ES89108895T patent/ES2053864T3/es not_active Expired - Lifetime
- 1989-05-18 EP EP89108895A patent/EP0344519B1/de not_active Expired - Lifetime
- 1989-05-19 US US07/354,536 patent/US4970215A/en not_active Expired - Lifetime
- 1989-05-26 NZ NZ229310A patent/NZ229310A/xx unknown
- 1989-05-29 FI FI892603A patent/FI91635C/fi not_active IP Right Cessation
- 1989-05-29 CA CA000600939A patent/CA1333802C/en not_active Expired - Lifetime
- 1989-05-29 AU AU35270/89A patent/AU616269B2/en not_active Expired
- 1989-05-29 PT PT90675A patent/PT90675B/pt not_active IP Right Cessation
- 1989-05-29 JP JP1132939A patent/JP2693576B2/ja not_active Expired - Lifetime
- 1989-05-29 IL IL90435A patent/IL90435A/xx unknown
- 1989-05-30 KR KR1019890007229A patent/KR0131202B1/ko not_active IP Right Cessation
- 1989-05-30 HU HU892733A patent/HU207719B/hu unknown
- 1989-05-30 DK DK263889A patent/DK169544B1/da not_active IP Right Cessation
- 1989-06-12 IE IE178489A patent/IE61922B1/en not_active IP Right Cessation
-
1995
- 1995-01-26 SG SG12795A patent/SG12795G/en unknown
- 1995-03-16 HK HK38895A patent/HK38895A/xx not_active IP Right Cessation
- 1995-05-31 HU HU95P/P00147P patent/HU211570A9/hu unknown
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1997
- 1997-05-23 JP JP09148420A patent/JP3076003B2/ja not_active Expired - Lifetime
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