KR960037662A - 아릴알킬-파리다진온 유도체 - Google Patents
아릴알킬-파리다진온 유도체 Download PDFInfo
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- KR960037662A KR960037662A KR1019960011859A KR19960011859A KR960037662A KR 960037662 A KR960037662 A KR 960037662A KR 1019960011859 A KR1019960011859 A KR 1019960011859A KR 19960011859 A KR19960011859 A KR 19960011859A KR 960037662 A KR960037662 A KR 960037662A
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- compound
- physiologically acceptable
- tetrahydropyridazin
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- 150000001875 compounds Chemical class 0.000 claims abstract 19
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 10
- 150000003839 salts Chemical class 0.000 claims abstract 8
- 229910052801 chlorine Inorganic materials 0.000 claims abstract 6
- 229910052731 fluorine Inorganic materials 0.000 claims abstract 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract 4
- 239000011737 fluorine Substances 0.000 claims abstract 4
- -1 methylenedioxy Chemical group 0.000 claims abstract 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract 3
- 229910052794 bromium Inorganic materials 0.000 claims abstract 3
- 239000000460 chlorine Substances 0.000 claims abstract 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 3
- 206010061218 Inflammation Diseases 0.000 claims abstract 2
- 125000003342 alkenyl group Chemical group 0.000 claims abstract 2
- 125000002947 alkylene group Chemical group 0.000 claims abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract 2
- 230000004054 inflammatory process Effects 0.000 claims abstract 2
- 229910052740 iodine Inorganic materials 0.000 claims abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 239000007788 liquid Substances 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 239000002552 dosage form Substances 0.000 claims 1
- RQPOEGOXCVKURG-UHFFFAOYSA-N ethyl n-[4-[[3-(3,4-dimethoxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OCC)=CC=C1CN1C(=O)CCC(C=2C=C(OC)C(OC)=CC=2)=N1 RQPOEGOXCVKURG-UHFFFAOYSA-N 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical compound C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 claims 1
- YYLMPPQOOUHPPJ-UHFFFAOYSA-N n-[3-[[3-(3,4-dimethoxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]acetamide Chemical compound C1=C(OC)C(OC)=CC=C1C(CCC1=O)=NN1CC1=CC=CC(NC(C)=O)=C1 YYLMPPQOOUHPPJ-UHFFFAOYSA-N 0.000 claims 1
- XDGXAZPROPKMKW-UHFFFAOYSA-N n-[4-[[3-(3,4-dimethoxyphenyl)-4-ethyl-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]-2,2,2-trifluoroacetamide Chemical compound N1=C(C=2C=C(OC)C(OC)=CC=2)C(CC)CC(=O)N1CC1=CC=C(NC(=O)C(F)(F)F)C=C1 XDGXAZPROPKMKW-UHFFFAOYSA-N 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 claims 1
- 239000002574 poison Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 abstract 1
- 206010020751 Hypersensitivity Diseases 0.000 abstract 1
- 230000007815 allergy Effects 0.000 abstract 1
- 208000006673 asthma Diseases 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/04—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having less than three double bonds between ring members or between ring members and non-ring members
-
- 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
-
- 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
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- 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
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Pulmonology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Transplantation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Curing Cements, Concrete, And Artificial Stone (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Hydrogenated Pyridines (AREA)
- Medicinal Preparation (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyridine Compounds (AREA)
Abstract
본 발명은 하기 일반식(Ⅰ)으로 표시되는 화합물 및 생리학적으로 허용 가능한 이의 염을 제공한다.
(단, 상기 식에서, R1및 R2는 각기 상호 독립적으로 H 또는 A이고, R3및 R4는 각기 상호 독립적으로 -OH, -O-R10, -S-R10, -SO-R10, -SO2-R10, Hal, 메틸렌디옥시, -NO2, -NH2, -NHR10또는 -NR10R11이고, R5는 R6및/또는 R7로 일- 또는 이치환되거나 비치환된 페닐라디칼이고, Q는 부재이거나 또는 탄소수가 1 내지 6인 알킬렌이고, R6및 R7은 각각 상호 독립적으로 -NH2, -NR8R9, -NHR10, -NR10R11, -NO2, Hal, CN, -OA, -COOH 또는 -COOA이고, R8이고 R9는 각기 상호 독립적으로 H, 탄소수가 1∼8이고, 1∼5개의 불소원자 및/ 또는 염소원자가 치환될 수 있는 아실, -COOA, -SO-A, -SO2A, -CONH2, -CONHA, -CONA2, -CO-COOH, -CO-COOA, -CO-CONH2, -CO-CONHA 또는 -CO-CONA2이고, A는 탄소수가 1∼6이고, 1∼5개의 불소원자 및/또는 염소원자가 치환될 수 있는 알킬이고, R10 및 R11은 각기 상호 독립적으로 A, 탄소수가 3∼7인 시클로알킬, 탄소수가 4∼8인 메틸렌시클로알킬 또는 탄소수가 2∼8인 알켄일이고, Hal은 F, Cl, Br 또는 I이다), 본 발명의 화합물은 포스포디에스테라제 Ⅳ 억제 특성을 나타내며, 염증의 치료 및 알레르기, 천식 및 자가 면역 질환의 치료에 사용할 수 있다.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (10)
- 하기 일반식(Ⅰ)으로 표시되는 화합물 및 생리학적으로 허용 가능한 이의 염.(단, 상기 식에서, R1및 R2는 각기 상호 독립적으로 H 또는 A이고, R3및 R4는 각기 상호 독립적으로 -OH, -O-R10, -S-R10, -SO-R10, -SO2-R10, Hal, 메틸렌디옥시, -NO2, -NH2, -NHR10또는 -NR10R11이고, R5는 R6및/또는 R7로 일- 또는 이치환되거나 비치환된 페닐라디칼이고, Q는 부재이거나 또는 탄소수가 1 내지 6인 알킬렌이고, R6및 R7은 각기 상호 독립적으로 -NH2, -NR8R9, -NHR10, -NR10R11, -NO2, Hal, CN, -OA, -COOH 또는 -COOA이고, R8이고 R9는 각기 상호 독립적으로 H, 탄소수가 1∼8이고, 1∼5개의 불소원자 및/ 또는 염소원자가 치환될 수 있는 아실, -COOA, -SO-A, -SO2A, -CONH2, -CONHA, -CONA2, -CO-COOH, -CO-COOA, -CO-CONH2, -CO-CONHA 또는 -CO-CONA2이고, A는 탄소수가 1∼6이고, 1∼5개의 불소원자 및/또는 염소원자가 치환될 수 있는 알킬이고, R10및 R11은 각기 상호 독립적으로 A, 탄소수가 3∼7인 시클로알킬, 탄소수가 4∼8인 메틸렌시클로알킬 또는 탄소수가 2∼8인 알켄일이고, Hal은 F, Cl, Br 또는 I이다).
- 제1항에 따른 일반식(Ⅰ)으로 표시되는 화합물의 거울상 이성질체.
- 제1항에 있어서, 상기한 일반식(Ⅰ)으로 표시되는 화합물이 다음 화합물 (a) 내지 (g)인 것을 특징으로 하는 화합물 : (a) 2-(4-에톡시카르보닐아미노벤질)-6-(3,4-디메톡시페닐)-2,3,4,5-테트라히드로피리다진-3-온 ; (b) 2-(3-메틸술포닐아미도벤질)-6-(3,4-디메톡시페닐)-2,3,4,5-테트라히드로피리다진-3-온 ; (c) 2-(3-아세트아미도벤질)-6-(3,4-디메톡시페닐)-2,3,4,5-테트라히드로피리다진-3-온 ; (d) 2-(4-트리플루오로아세트아미도벤질)-6-(3,4-디메톡시페닐)-5-에틸-2,3,4,5-테트라히드로피리다진-3-온 ; (e) 2-(4-에톡시카르보닐아미노벤질-6-(3,4-디멘톡시페닐)-5-에틸-2,3,4,5-테트라히드로피리다진-3-온 ; (f) 2-(4-메톡시카르보닐아미노벤질)-6-(3,4-디메톡시페닐)-5-에틸-2,3,4,5-테트라히드로피리다진-3-온 ; (e) 2-(4-부티릴아미노벤질)-6-(3,4-디메톡시페닐)-5-에틸-2,3,4,5-테트라히드로피리다진-3-온.
- 하기 일반식(Ⅱ)의 화합물을 하기 일반식(Ⅲ)의 화합물과 반응시키거나, 또는 하기 일반식(Ⅳ)의 화합물을 하기 일반식(Ⅴ)의 화합물과 반응시키거나, 또는 상기 일반식(Ⅰ)의 화합물에서 라디칼 R5중 하나가 니트로기를 환원시키거나, 일차 또는 이차 아미노기를 아실화 또는 알킬화시키거나, 또는 시아노기를 가수분해시킴으로써 라디칼 R5중 다른 하나로 전환시키거나, 및/또는 일반식(Ⅰ)에 상응하되, R3및/또는 R4대신에 하나 또는 둘의 유리 OH기를 함유하는 화합물을 임의로, 일반식 R3-X 또는 R4-X의 화합물(여기에서, R3, R4및 X는 상기에서 정의한 바와 같다)과 각각 반응시키거나, 및/또는 상기 일반식(Ⅰ)의 염기를 산으로 처리하여 이의 염증 하나로 전환시키는 것을 특징으로 하는 일반식(Ⅰ)의 화합물 및 이들의 염의 제조방법.(단, 상기 식에서, R1, R2, R3, R4, R5및 Q는 제1항에 정의한 바와 같고, X는 Cl, Br, OH 또는 반응적으로 에스테르화된 OH기이며, E는 H 또는 탄소수가 1 내지 4인 알킬이다.)
- 제1항에 따른 일반식(Ⅰ)으로 표시되는 화합물 및/또는 생리학적으로 허용 가능한 이의 염중 하나를 1종 이상의 고체, 액체 또는 반액체 부형제 또는 보조제와 함께 적합한 투여 형태로 만드는 것을 특징으로 하는 약제학적 제형의 제조방법.
- 제1항에 따른 일반식(Ⅰ)으로 표시되는 화합물 1종 이상 및/또는 생리학적으로 허용 가능한 이의 염중 하나를 함유하는 것을 특징으로 하는 약제학적 제형.
- 질병 치료용 약물의 제조에 사용되는 제1항에 따른 일반식(Ⅰ)의 화합물 및/또는 생리학적으로 허용 가능한 이의 염.
- 포스포디에스테라제 Ⅳ 억제제로 사용되는 제1항에 따른 일반식(Ⅰ)의 화합물 및/또는 생리학적으로 허용 가능한 이의 염.
- 약물의 제조에 사용되는 제1항에 따른 일반식(Ⅰ)의 화합물 및/또는 생리학적으로 허용 가능한 이의 염.
- 질병의 치료에 사용되는 제1항에 따른 일반식(Ⅰ)의 화합물 및/또는 생리학적으로 허용 가능한 이의 염.※ 참고사항 : 최초출원 내용에 의하여 공개되는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19514568.2 | 1995-04-20 | ||
| DE19514568A DE19514568A1 (de) | 1995-04-20 | 1995-04-20 | Arylalkyl-pyridazinone |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR960037662A true KR960037662A (ko) | 1996-11-19 |
| KR100428879B1 KR100428879B1 (ko) | 2004-07-15 |
Family
ID=7759974
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019960011859A KR100428879B1 (ko) | 1995-04-20 | 1996-04-19 | 아릴알킬-피리다진온유도체 |
Country Status (21)
| Country | Link |
|---|---|
| US (2) | US6399611B1 (ko) |
| EP (1) | EP0738715B1 (ko) |
| JP (1) | JP4005157B2 (ko) |
| KR (1) | KR100428879B1 (ko) |
| CN (1) | CN1159299C (ko) |
| AT (1) | ATE231842T1 (ko) |
| AU (1) | AU705025B2 (ko) |
| CA (1) | CA2174472C (ko) |
| CZ (1) | CZ291868B6 (ko) |
| DE (2) | DE19514568A1 (ko) |
| DK (1) | DK0738715T3 (ko) |
| ES (1) | ES2191070T3 (ko) |
| HU (1) | HU226198B1 (ko) |
| NO (1) | NO307931B1 (ko) |
| PT (1) | PT738715E (ko) |
| RU (1) | RU2159236C2 (ko) |
| SI (1) | SI0738715T1 (ko) |
| SK (1) | SK284167B6 (ko) |
| TW (1) | TW475927B (ko) |
| UA (1) | UA43853C2 (ko) |
| ZA (1) | ZA963154B (ko) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19533975A1 (de) * | 1995-09-14 | 1997-03-20 | Merck Patent Gmbh | Arylalkyl-diazinone |
| JP4017214B2 (ja) | 1996-06-11 | 2007-12-05 | 興和創薬株式会社 | ５−フェニル−３−ピリダジノン誘導体 |
| EP0924204A4 (en) * | 1996-08-27 | 2002-10-23 | Nikken Chemicals Co Ltd | 2-PHENYLMORPHOLIN-5-ONE DERIVATIVES AND PHARMACEUTICAL COMPOSITION COMPRISING THE SAME |
| DE19850701A1 (de) * | 1998-11-04 | 2000-05-11 | Merck Patent Gmbh | Benzoylpyridazine |
| IL147688A0 (en) | 1999-08-21 | 2002-08-14 | Byk Gulden Lomberg Chem Fab | Synergistic combination |
| DE10064997A1 (de) * | 2000-12-23 | 2002-06-27 | Merck Patent Gmbh | Benzoylpyridazine |
| JP2004521928A (ja) * | 2001-02-12 | 2004-07-22 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフトング | ４型ホスホジエステラーゼ阻害剤の心筋疾患における使用 |
| US6872382B1 (en) | 2001-05-21 | 2005-03-29 | Alcon, Inc. | Use of selective PDE IV inhibitors to treat dry eye disorders |
| KR20040007596A (ko) * | 2001-05-23 | 2004-01-24 | 다나베 세이야꾸 가부시키가이샤 | 골절 치료 촉진용 조성물 |
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| US7074959B2 (en) * | 2002-08-01 | 2006-07-11 | New Mexico Highlands University | Methods and systems for remediating hydrazine-contaminated equipment and/or surfaces |
| KR20050115331A (ko) | 2003-04-01 | 2005-12-07 | 어플라이드 리서치 시스템스 에이알에스 홀딩 엔.브이. | 불임증 포스포디에스터라제의 억제제 |
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| US4734415A (en) * | 1982-08-13 | 1988-03-29 | Warner-Lambert Company | Substituted 4,5-dihydro-6-(substituted)-phenyl-3(2H)-pyridazinones and 6-(substituted) phenyl-3(2H)-pyridazinones |
| NZ208107A (en) * | 1983-05-11 | 1986-12-05 | Byk Gulden Lomberg Chem Fab | 6-aryl-3(2h)-pyridazinones and pharmaceutical compositions |
| US4666902A (en) | 1983-06-20 | 1987-05-19 | Cassella Aktiengesellschaft | Tetrahydropyridazinone derivatives, processes for their preparation and their use |
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| GB8903130D0 (en) | 1989-02-11 | 1989-03-30 | Orion Yhtymae Oy | Substituted pyridazinones |
| AU6081690A (en) * | 1989-08-10 | 1991-02-14 | Glaxo Inc. | Pyridazinones having cardiotonic and beta block activity |
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-
1995
- 1995-04-20 DE DE19514568A patent/DE19514568A1/de not_active Withdrawn
-
1996
- 1996-02-27 TW TW085102257A patent/TW475927B/zh not_active IP Right Cessation
- 1996-04-11 SI SI9630593T patent/SI0738715T1/xx unknown
- 1996-04-11 PT PT96105702T patent/PT738715E/pt unknown
- 1996-04-11 EP EP96105702A patent/EP0738715B1/de not_active Expired - Lifetime
- 1996-04-11 DE DE59610081T patent/DE59610081D1/de not_active Expired - Lifetime
- 1996-04-11 AT AT96105702T patent/ATE231842T1/de active
- 1996-04-11 ES ES96105702T patent/ES2191070T3/es not_active Expired - Lifetime
- 1996-04-11 DK DK96105702T patent/DK0738715T3/da active
- 1996-04-16 AU AU50711/96A patent/AU705025B2/en not_active Ceased
- 1996-04-17 SK SK487-96A patent/SK284167B6/sk unknown
- 1996-04-18 CN CNB961051086A patent/CN1159299C/zh not_active Expired - Fee Related
- 1996-04-18 CA CA002174472A patent/CA2174472C/en not_active Expired - Fee Related
- 1996-04-19 ZA ZA963154A patent/ZA963154B/xx unknown
- 1996-04-19 US US08/634,830 patent/US6399611B1/en not_active Expired - Fee Related
- 1996-04-19 CZ CZ19961132A patent/CZ291868B6/cs not_active IP Right Cessation
- 1996-04-19 RU RU96107677/04A patent/RU2159236C2/ru not_active IP Right Cessation
- 1996-04-19 NO NO961578A patent/NO307931B1/no not_active IP Right Cessation
- 1996-04-19 KR KR1019960011859A patent/KR100428879B1/ko not_active IP Right Cessation
- 1996-04-19 HU HU9601034A patent/HU226198B1/hu not_active IP Right Cessation
- 1996-04-19 UA UA96041565A patent/UA43853C2/uk unknown
- 1996-04-19 JP JP12078096A patent/JP4005157B2/ja not_active Expired - Fee Related
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