KR970010928B1 - 시클릭 펩톨라이드 - Google Patents
시클릭 펩톨라이드 Download PDFInfo
- Publication number
- KR970010928B1 KR970010928B1 KR1019880007371A KR880007371A KR970010928B1 KR 970010928 B1 KR970010928 B1 KR 970010928B1 KR 1019880007371 A KR1019880007371 A KR 1019880007371A KR 880007371 A KR880007371 A KR 880007371A KR 970010928 B1 KR970010928 B1 KR 970010928B1
- Authority
- KR
- South Korea
- Prior art keywords
- peptolide
- cyclic
- leu
- cyclic peptolide
- producing
- Prior art date
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- 125000004122 cyclic group Chemical group 0.000 title claims abstract description 16
- 230000002538 fungal effect Effects 0.000 claims abstract description 5
- 230000003110 anti-inflammatory effect Effects 0.000 claims abstract description 3
- 230000001506 immunosuppresive effect Effects 0.000 claims abstract description 3
- 241001264173 Cylindrotrichum Species 0.000 claims abstract 2
- 230000002141 anti-parasite Effects 0.000 claims abstract 2
- AHQFCPOIMVMDEZ-UNISNWAASA-N (e,2s,3r,4r)-3-hydroxy-4-methyl-2-(methylamino)oct-6-enoic acid Chemical group CN[C@H](C(O)=O)[C@H](O)[C@H](C)C\C=C\C AHQFCPOIMVMDEZ-UNISNWAASA-N 0.000 claims description 4
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 3
- 238000012258 culturing Methods 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- XJODGRWDFZVTKW-LURJTMIESA-N (2s)-4-methyl-2-(methylamino)pentanoic acid Chemical group CN[C@H](C(O)=O)CC(C)C XJODGRWDFZVTKW-LURJTMIESA-N 0.000 claims 2
- 235000015097 nutrients Nutrition 0.000 claims 2
- 241000721047 Danaus plexippus Species 0.000 claims 1
- NGEWQZIDQIYUNV-UHFFFAOYSA-N L-valinic acid Natural products CC(C)C(O)C(O)=O NGEWQZIDQIYUNV-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- 244000005700 microbiome Species 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 238000007363 ring formation reaction Methods 0.000 claims 1
- PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical class CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 abstract description 5
- 108010036949 Cyclosporine Proteins 0.000 abstract description 5
- 229960001265 ciclosporin Drugs 0.000 abstract description 5
- 229930182912 cyclosporin Natural products 0.000 abstract description 4
- 229930105110 Cyclosporin A Natural products 0.000 abstract description 3
- 150000001408 amides Chemical class 0.000 abstract description 2
- 150000002148 esters Chemical class 0.000 abstract 1
- 230000004151 fermentation Effects 0.000 abstract 1
- 238000000855 fermentation Methods 0.000 abstract 1
- 108010036941 Cyclosporins Proteins 0.000 description 1
- -1 N-methyl- (4R) -4-but-2E- En-1-yl-4-methyl- (L) -threonyl residues Chemical group 0.000 description 1
- 150000001280 alpha hydroxy acids Chemical group 0.000 description 1
- 235000008206 alpha-amino acids Nutrition 0.000 description 1
- 150000001371 alpha-amino acids Chemical class 0.000 description 1
- 125000000539 amino acid group Chemical group 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N1/00—Microorganisms, e.g. protozoa; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
- C12N1/14—Fungi; Culture media therefor
- C12N1/145—Fungal isolates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/64—Cyclic peptides containing only normal peptide links
-
- 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
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K11/00—Depsipeptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K11/02—Depsipeptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof cyclic, e.g. valinomycins ; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12R—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES C12C - C12Q, RELATING TO MICROORGANISMS
- C12R2001/00—Microorganisms ; Processes using microorganisms
- C12R2001/645—Fungi ; Processes using fungi
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biochemistry (AREA)
- Zoology (AREA)
- Biotechnology (AREA)
- Wood Science & Technology (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Immunology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Virology (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- General Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Botany (AREA)
- Mycology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Tropical Medicine & Parasitology (AREA)
- Public Health (AREA)
- Biomedical Technology (AREA)
- Microbiology (AREA)
- Transplantation (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Peptides Or Proteins (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
내용없음.
Description
본 발명은 약제로서 유용한 신규의 시클릭 펩톨라이드에 관한 것이다.
본 명세서에서 사용하는 용어 펩톨라이드는 아미드 결합과 에스테르 결합 둘 다에 의해 함께 결합되어 있는 α-히드록시 및 α-아미노산들을 포함한 천연 또는 합성 화합물을 의미하는 것이다. 즉, 펩티드내의 아미드 결합을 에스테르 결합으로 치환시킴으로써 수득된 구조가 펩톨라이드이다.
펩티드들 중 중요한 부류가 시클로스포린으로서, 이 시콜로스포린은 통상적으로 11개의 아미노산 잔기들로 이루어진 시클릭 구조를 특징으로 하며, 그들 중 하나가 N-메틸-(4R)-4-부트-2E-엔-1-일-4-메틸-(L)-트레오닐 잔기(MeBmt로 약칭함) 도는 그의 유도체이다. 많은 시클로스포린류가 약리학적 특성들, 특히 면역 억제 활성 및 소염작용성을 갖는다. 최초로 분리된 시클로스포린은 천연의 진균 대사물 시클로스포린 A(Ciclosporin)로서 Snadimmune 2 2 1-4
""2 5 8 10"2 1 * 2 2 2 50 6 6
""50 7 7 6 50 8 6
""50 7 50 50 50 50 7
"2 5 8 10 2 5 8 10 2 5 8 10 20 20 3 2 5 8 10 2 2 20 3
Claims (10)
- 하기 식(Ⅱ)를 갖는 시클릭펩톨라이드.
(식 중, W는 MeBmt, 8'-OHMeBmt 또는 MeBmtH2이고,X는 Sar 또는 Gly이며,Y는 MeLeu 또는 Leu 이고,Z는 Leu, Ile 또는 Va1이며,A는 α-히드록시카르복실산의 잔기이다.) - 제 1 항에 있어서,A가 (D)Hiv인 시클릭 펩톨라이드.
- (Ther)2(Leu)5(D - Hiv)8(Leu) 10 - 시클로스포린
- 영양배지 내에서 생산성 미생물을 배양하는 단계를 특징으로 하는 제 1 항 내지 제 3 항 중 어느 한 항의 시클릭 펩톨라이드를 제조하는 방법.
- 실린드로트리쿰 보노르덴(Cylindrotrichum Bonorden) 속에 속하는 생산성 진균 균주를 영양배지 내에서 배양하는 단계를 특징으로 하는 제 1 항 내지 제 3 항 중 어느 한 항의 시클릭 펩톨라이드를 제조하는 방법.
- 실린드로트리쿰 보노르덴 속에 시클릭 펩톨라이드-생산 진균 균주를 배양하여 수득되는 제 3 항의 시클릭 펩톨라이드.
- 약학적으로 허용되는 희석제 또는 담체와 함께 제 1 항 내지 제 3 항 중 어느 한 항의 시클릭 펩톨라이드를 함유하는, 면역억제활성, 소염작용성 및 구충활성을 갖는 약학 조성물.
- 전균 군주 NRRL 18230
- 아미노-말단기 대신에 히드록시-말단기를 갖는 펩티드 또는 직쇄 펩톨라이드의 폐환반응에 의해 제 1 항 내지 제 3 항 중 어느 한 항의 시클릭 펩톨라이드를 제조하는 방법.
- a) O-보호된 형태의 하기식 (Ⅲ)의 시클릭 펩톨라이드로부터 O-보호기들을 제거하고:b) 잔기 1 및 2 중 하나 또는 둘다가 O-보호된 형태 또는 비보호된 형태의 하기식(Ⅷ)의 직쇄 히드록시-운데카펩티드에 대하여 폐환반응을 실시하고, 이어서, 필요하다면, 단계(a)의 공정을 수행하고 ; 필요에 따라서c) W가 MeBmt인 수득된 하기식(II)의 시클릭 펩톨라이드에 대하여 수소 첨가반응을 수행하며 W가 MeBmtH2인 상응하는 시클릭 펩톨라이드를 수득함으로 특징으로 하는 하기식(II)의 시클릭 펩톨라이드의 제조방법.
(식 중, W는 MeBmt, 8'-OHMeBmt 또는 MeBmtH2이고,X는 Sar 또는 Gly이며,Y는 MeLeu 또는 Leu이고,Z는 Leu, Ile 또는 Val이며,A는 α-히드록시카르복실산의 잔기이고, 및R'는 적당한 O-보호기이다.)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH231787 | 1987-06-19 | ||
| CH2317/87-5 | 1987-06-19 | ||
| CH02317/87-5 | 1987-06-19 | ||
| CH02517/87-2 | 1987-07-02 | ||
| CH2517/87-2 | 1987-07-02 | ||
| CH251787 | 1987-07-02 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR890000518A KR890000518A (ko) | 1989-03-15 |
| KR970010928B1 true KR970010928B1 (ko) | 1997-07-02 |
Family
ID=25690129
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019880007371A KR970010928B1 (ko) | 1987-06-19 | 1988-06-18 | 시클릭 펩톨라이드 |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US5116816A (ko) |
| EP (1) | EP0296123B1 (ko) |
| JP (1) | JP2641256B2 (ko) |
| KR (1) | KR970010928B1 (ko) |
| AT (1) | ATE110784T1 (ko) |
| AU (1) | AU623078B2 (ko) |
| CA (1) | CA1338183C (ko) |
| DE (1) | DE3851268T2 (ko) |
| ES (1) | ES2056954T3 (ko) |
| FI (1) | FI87928C (ko) |
| HU (1) | HU204101B (ko) |
| IE (1) | IE64008B1 (ko) |
| IL (1) | IL86789A (ko) |
| MY (1) | MY103735A (ko) |
| NZ (1) | NZ225071A (ko) |
| PH (1) | PH25933A (ko) |
| PT (1) | PT87763B (ko) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU213553B (en) * | 1992-05-25 | 1997-07-28 | Biogal Gyogyszergyar | Process for isolating of cyclosporin-a |
| JP3480848B2 (ja) * | 1992-06-19 | 2003-12-22 | タカラバイオ株式会社 | 環状ペプチドの合成方法 |
| US5260215A (en) * | 1992-07-20 | 1993-11-09 | Merck & Co., Inc. | Fungal microorganism ATCC 74167 capable of producing cholesterol lowering compounds |
| US6187547B1 (en) | 1993-09-08 | 2001-02-13 | Novartis Ag | Assay kit |
| KR100378974B1 (ko) * | 1994-07-27 | 2003-10-08 | 노바티스 아게 | 유기화합물 |
| JP3089350B2 (ja) * | 1995-11-20 | 2000-09-18 | ギルフォード ファーマシューティカルズ インコーポレイテッド | シクロフィリンロタマーゼ活性の阻害剤 |
| US5858401A (en) * | 1996-01-22 | 1999-01-12 | Sidmak Laboratories, Inc. | Pharmaceutical composition for cyclosporines |
| US5709797A (en) * | 1996-06-05 | 1998-01-20 | Poli Industria Chimica S.P.A. | Method of isolating cyclosporins |
| CN1130373C (zh) * | 1996-09-13 | 2003-12-10 | 诺瓦蒂斯有限公司 | [3'－脱氧－3'－氧代－MeBmt]'环孢菌素制备方法 |
| US20030220234A1 (en) * | 1998-11-02 | 2003-11-27 | Selvaraj Naicker | Deuterated cyclosporine analogs and their use as immunodulating agents |
| DK0991660T3 (da) | 1997-10-08 | 2006-02-13 | Isotechnika Inc | Deuterede og udeuterede cyclosporinanaloger og deres anvendelse som immunmodulerende midler |
| EP1214293A1 (en) * | 1999-09-08 | 2002-06-19 | Guilford Pharmaceuticals Inc. | Non-peptidic cyclophilin binding compounds and their use |
| US6656971B2 (en) | 2001-01-25 | 2003-12-02 | Guilford Pharmaceuticals Inc. | Trisubstituted carbocyclic cyclophilin binding compounds and their use |
| US6593362B2 (en) | 2001-05-21 | 2003-07-15 | Guilford Pharmaceuticals Inc. | Non-peptidic cyclophilin binding compounds and their use |
| US20040147433A1 (en) * | 2001-06-14 | 2004-07-29 | Marcus Keep | Neuroimmunophilins for selective neuronal radioprotection |
| KR100982466B1 (ko) * | 2001-10-19 | 2010-09-16 | 이소테크니카 인코포레이티드 | 시클로스포린 유사체의 합성 |
| AR036852A1 (es) * | 2001-10-19 | 2004-10-06 | Isotechnika Inc | Preconcentrado de una microemulsion de analogos de ciclosporina, su metodo de preparacion y metodos para producir inmunosupresion |
| WO2004082629A2 (en) * | 2003-03-17 | 2004-09-30 | Albany Molecular Research, Inc. | Novel cyclosporins |
| EP1809656A4 (en) * | 2004-09-29 | 2009-03-25 | Amr Technology Inc | CYCLOSPORINAL KINANALOGA AND ITS PHARMACEUTICAL APPLICATIONS |
| EP1804823A4 (en) * | 2004-09-29 | 2010-06-09 | Amr Technology Inc | NEW CYCLOSPORIN ANALOGUE AND ITS PHARMACEUTICAL APPLICATIONS |
| WO2006041631A2 (en) * | 2004-10-06 | 2006-04-20 | Amr Technology, Inc. | Novel cyclosporin alkynes and their utility as pharmaceutical agents |
| ES2314731T3 (es) * | 2004-11-22 | 2009-03-16 | Astellas Pharma Inc. | Analogo de ciclosporina. |
| US7696166B2 (en) * | 2006-03-28 | 2010-04-13 | Albany Molecular Research, Inc. | Use of cyclosporin alkyne/alkene analogues for preventing or treating viral-induced disorders |
| US7696165B2 (en) * | 2006-03-28 | 2010-04-13 | Albany Molecular Research, Inc. | Use of cyclosporin alkyne analogues for preventing or treating viral-induced disorders |
| CN102245625A (zh) | 2008-10-17 | 2011-11-16 | 威斯康星旧生研究基金会 | 制备有生物活性的α-β肽的方法 |
| CA2741829A1 (en) * | 2008-11-06 | 2010-05-14 | Debio Recherche Pharmaceutique S.A. | Cycloundecadepsipeptide compounds and use of said compounds as a medicament |
| DE102008060549A1 (de) | 2008-12-04 | 2010-06-10 | MAX-PLANCK-Gesellschaft zur Förderung der Wissenschaften e.V. | Wirkstoff-Peptid-Konstrukt zur extrazellulären Anreicherung |
| WO2011141891A1 (en) | 2010-05-12 | 2011-11-17 | Debio Recherche Pharmaceutique S.A. | Use of cycloundecadepsipeptide compounds |
| PT2651965T (pt) | 2010-12-15 | 2019-01-28 | Contravir Pharmaceuticals Inc | Moléculas analógas de ciclosporinas modificadas ao nivel dos aminoácidos 1 e 3 |
| EP2705856A1 (en) | 2012-09-07 | 2014-03-12 | Deutsches Zentrum für Neurodegenerative Erkrankungen e.V. | Compounds for the treatment of neurodegenerative disorders |
| GB201217560D0 (en) * | 2012-10-02 | 2012-11-14 | Mitopharm Ltd | Novel cyclic depsipeptide compounds and their uses |
| HUP1500502A2 (en) | 2015-10-26 | 2017-04-28 | Rotachrom Tech Kft | Process for the purification of cyclosporin-a |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2819094A1 (de) * | 1977-05-10 | 1978-11-23 | Sandoz Ag | Cyclosporin-derivate, ihre verwendung und herstellung |
| JPS5665853A (en) * | 1979-11-01 | 1981-06-03 | Sankyo Co Ltd | Mycoplanesin derivative and its preparation |
| EP0056782B1 (en) * | 1981-01-09 | 1984-08-01 | Sandoz Ag | Novel cyclosporins |
| US4649047A (en) * | 1985-03-19 | 1987-03-10 | University Of Georgia Research Foundation, Inc. | Ophthalmic treatment by topical administration of cyclosporin |
| EP0274873B1 (en) * | 1986-12-15 | 1992-09-23 | Eli Lilly And Company | Antibiotic a10255 complex and factors, process, microorganisms for its production |
| GB8727807D0 (en) * | 1987-11-27 | 1987-12-31 | Lepetit Spa | Novel antibiotic compounds named a/16686 factors a'1,a'2 and a'3 |
-
1988
- 1988-06-15 AT AT88810408T patent/ATE110784T1/de not_active IP Right Cessation
- 1988-06-15 ES ES88810408T patent/ES2056954T3/es not_active Expired - Lifetime
- 1988-06-15 EP EP88810408A patent/EP0296123B1/en not_active Expired - Lifetime
- 1988-06-15 DE DE3851268T patent/DE3851268T2/de not_active Expired - Lifetime
- 1988-06-16 CA CA000569655A patent/CA1338183C/en not_active Expired - Lifetime
- 1988-06-17 HU HU883121A patent/HU204101B/hu unknown
- 1988-06-17 MY MYPI88000673A patent/MY103735A/en unknown
- 1988-06-17 IL IL86789A patent/IL86789A/xx not_active IP Right Cessation
- 1988-06-17 IE IE183888A patent/IE64008B1/en not_active IP Right Cessation
- 1988-06-17 PT PT87763A patent/PT87763B/pt not_active IP Right Cessation
- 1988-06-17 NZ NZ225071A patent/NZ225071A/xx unknown
- 1988-06-17 AU AU18124/88A patent/AU623078B2/en not_active Expired
- 1988-06-17 PH PH37083A patent/PH25933A/en unknown
- 1988-06-17 FI FI882926A patent/FI87928C/fi active IP Right Grant
- 1988-06-18 KR KR1019880007371A patent/KR970010928B1/ko not_active IP Right Cessation
- 1988-06-18 JP JP63151056A patent/JP2641256B2/ja not_active Expired - Lifetime
- 1988-06-20 US US07/209,680 patent/US5116816A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| PH25933A (en) | 1991-12-19 |
| PT87763B (pt) | 1992-10-30 |
| EP0296123A2 (en) | 1988-12-21 |
| HU204101B (en) | 1991-11-28 |
| PT87763A (pt) | 1988-07-01 |
| NZ225071A (en) | 1991-05-28 |
| US5116816A (en) | 1992-05-26 |
| ATE110784T1 (de) | 1994-09-15 |
| JPS6425798A (en) | 1989-01-27 |
| CA1338183C (en) | 1996-03-26 |
| MY103735A (en) | 1993-09-30 |
| AU1812488A (en) | 1988-12-22 |
| ES2056954T3 (es) | 1994-10-16 |
| DE3851268D1 (de) | 1994-10-06 |
| AU623078B2 (en) | 1992-05-07 |
| HUT50220A (en) | 1989-12-28 |
| FI87928B (fi) | 1992-11-30 |
| FI882926A (fi) | 1988-12-20 |
| EP0296123A3 (en) | 1990-06-20 |
| FI87928C (fi) | 1993-03-10 |
| EP0296123B1 (en) | 1994-08-31 |
| DE3851268T2 (de) | 1995-01-26 |
| JP2641256B2 (ja) | 1997-08-13 |
| FI882926A0 (fi) | 1988-06-17 |
| KR890000518A (ko) | 1989-03-15 |
| IL86789A (en) | 1993-02-21 |
| IL86789A0 (en) | 1988-11-30 |
| IE64008B1 (en) | 1995-06-28 |
| IE881838L (en) | 1988-12-19 |
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