KR840006332A - 스페르구알린-관련 화합물의 제조방법 - Google Patents
스페르구알린-관련 화합물의 제조방법 Download PDFInfo
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- KR840006332A KR840006332A KR1019830004071A KR830004071A KR840006332A KR 840006332 A KR840006332 A KR 840006332A KR 1019830004071 A KR1019830004071 A KR 1019830004071A KR 830004071 A KR830004071 A KR 830004071A KR 840006332 A KR840006332 A KR 840006332A
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- 150000001875 compounds Chemical class 0.000 title claims 13
- 238000004519 manufacturing process Methods 0.000 title 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 10
- -1 amino, guanidino Chemical group 0.000 claims 9
- 125000000539 amino acid group Chemical group 0.000 claims 8
- 125000003277 amino group Chemical group 0.000 claims 8
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 6
- 125000001424 substituent group Chemical group 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 150000001413 amino acids Chemical class 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 4
- 125000006239 protecting group Chemical group 0.000 claims 4
- NPWGWQRXHVJJRD-UHFFFAOYSA-N N-hydroxyglycine Chemical group ONCC(O)=O NPWGWQRXHVJJRD-UHFFFAOYSA-N 0.000 claims 3
- 125000004423 acyloxy group Chemical group 0.000 claims 3
- 125000000524 functional group Chemical group 0.000 claims 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 125000001931 aliphatic group Chemical group 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims 2
- NHDCYJHZGHPLQU-UHFFFAOYSA-N 7-(diaminomethylideneamino)-3-hydroxyheptanoic acid Chemical compound NC(N)=NCCCCC(O)CC(O)=O NHDCYJHZGHPLQU-UHFFFAOYSA-N 0.000 claims 1
- TURWKAWYHMVRNM-UHFFFAOYSA-N 7-(diaminomethylideneamino)heptanoic acid Chemical compound NC(=N)NCCCCCCC(O)=O TURWKAWYHMVRNM-UHFFFAOYSA-N 0.000 claims 1
- LCWXJXMHJVIJFK-UHFFFAOYSA-N Hydroxylysine Natural products NCC(O)CC(N)CC(O)=O LCWXJXMHJVIJFK-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 238000000354 decomposition reaction Methods 0.000 claims 1
- YSMODUONRAFBET-UHFFFAOYSA-N delta-DL-hydroxylysine Natural products NCC(O)CCC(N)C(O)=O YSMODUONRAFBET-UHFFFAOYSA-N 0.000 claims 1
- 235000014113 dietary fatty acids Nutrition 0.000 claims 1
- YSMODUONRAFBET-UHNVWZDZSA-N erythro-5-hydroxy-L-lysine Chemical compound NC[C@H](O)CC[C@H](N)C(O)=O YSMODUONRAFBET-UHNVWZDZSA-N 0.000 claims 1
- 229930195729 fatty acid Natural products 0.000 claims 1
- 239000000194 fatty acid Substances 0.000 claims 1
- 150000004665 fatty acids Chemical class 0.000 claims 1
- QJHBJHUKURJDLG-UHFFFAOYSA-N hydroxy-L-lysine Natural products NCCCCC(NO)C(O)=O QJHBJHUKURJDLG-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- PPIJBKDZMOYFAW-UHFFFAOYSA-N n-[2-[4-(3-aminopropylamino)butylamino]-2-oxoethyl]-7-(diaminomethylideneamino)heptanamide Chemical compound NCCCNCCCCNC(=O)CNC(=O)CCCCCCNC(N)=N PPIJBKDZMOYFAW-UHFFFAOYSA-N 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/04—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton
-
- 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
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/04—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton
- C07C279/14—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton being further substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- 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
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
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- 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)
- Oncology (AREA)
- Hematology (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (9)
- 일반식 :(상기 식에서, R1은 수소원자, 히드록실기, 또는 1내지 10개의 탄소원자를 가지는 지방족 아실록시기이며 m은 4내지 5의 정수이고, R'2는- 또는- 아미노산(- 또는- 아미노산이 치환체로서 기능기를 가지고 있을 때에는 그것은 보호된다)의- 또는- 아미노기 및- 카르복실기로 부터 각각 수소원자 및 히드록실기를 제거함으로서 형성된 아미노산 잔류를(- 히드록시글리신 잔류물 제외)인데, 상기 아미노산 잔류물은 인접한 카르보닐기 및 아미노기와 산아미드 결합을 형성한다. 그리고 R3와 R4는 같거나 다른 것으로 각각 아미노기를 위한 보호기이다)의 화합물로부터 공지된 방법으로 보호기를 제거하는 것을 포함하는 일반식 :(상기 식에서, R1과 m은 앞서 정의한 바와 같고, R2는- 또는- 아미노산의- 또는- 아미노기 및 μ- 카르복실기로 부터 각각 수소원자 및 히드록실기를 제거함으로써 형성된 아미노산 잔류물(- 히드록시글리신의 잔류물 제외)인데 상기 아미노산 잔류물은 인접한 카르보닐기 및 아미노기와 산아미드 결합을 형성한다)의 화합물(또는 그것의 염)의 제조방법.
- 제1항에 있어서, R1이 수소원자, 히드록실기 또는(저급) 아실록시 기이고, 그리고 n'2가 일반식 :(상기 식에서, X'1은 수소원자 또는 1내지 6개의 탄소원자를 가진 알킬기인데, 그 알킬기는 치환제로서, 히드록실, 저급알콕시, 카르보닐, (저급)알킬옥시카르보닐, 아미노, 구아니디노, 페닐, 히드록시-치환 페닐, 이미다졸, 메르캅토 또는 (저급) 알킬메르캅토 기를 가지며, 이러한 치환제 내의 기능기는 보호되고, n은 0내지 5의 정수이다)으로 표시되는 기 또는 일반식 :(상기 식에서, X2는 치환체로서 히드록실기를 가지는 프로필렌 기를 의미한다)으로 표시되는 기이고, R2가 일반식 :(상기 식에서, X1은 수소원자 또는 1내지 6개의 탄소원자를 가지는 알킬기인데, 그 알킬기는 치환제로서 히드록실, 저급알콕시, 카르복실, (저급) 알킬록시카르보닐, 아미노, 구아니디노, 페닐, 히드록시-치환 페닐, 이미다졸, 메르캅토 또는 (저급) 알킬메르캅토 기를 가진다)로 표시되는 기인 방법.
- 제2항에 있어서, R1이 수소원자 또는 히드록실기이고, X'1이 수소원자, 히드록시기메틸기, 구아니디노프로필기 또는 벤질기이며, 히드록시메틸 및 구아니디노프로필기는 보호되고, X1이 수소원자, 히드록시메틸기, 구아니디노프로 필기 또는 벤질기이고, n이 0.1 또는 2인 방법.
- 제1항에 있어서, 일반식(Ⅱ)의 화합물이 10-[N-(7-구아니디노헵탄오일)-글리실]-1,5-di 보호-1,5,10-트리아자데칸이고, 일반식(Ⅰ)의 화합물이 10-[N-(7-구아니디노헵탄오일)-글리실]-1,5,10-트리아자데칸인 방법.
- 제1항에 있어서, 일반식(Ⅱ)의 화합물이 10-[O-(7-구아니디노헵탄오일)-0-보호-L-세릴]-1,5-di 보호-1,5,10-트리아자데칸이고 일반식(Ⅰ)의 화합물이 10-[N-(7-구아니디노헵탄오일)-L-세릴]15,10-트리아자데칸인 방법.
- 제1항에 있어서, 일반식(Ⅱ)의 화합물이[10-(7-구아니디노-3(S(-히드록시헵탄오일)-0-보호-L-세릴]-1,5-di 보호-1,5,11-트리아자데칸인 방법.
- 제1항에 있어서, 보호기가 환원 또는 산분해에 의해 제거되는 방법.
- 일반식 :(상기 식에서, R1은 수소원자, 히드록실기 또는 1내지 10개의 탄소원자를 가지는 지방족 아실록시기이고, m은 4내지 6의 정수이다)로 표시되는- 구아니디노 | 지방산 또는 그것의 반응유도체를 일반식 :(상기 식에서, R'2는- 또는- 아미노산(- 또는- 아미노산이 치환체로서 기능기를 가진 때에는 그것은 보호된다)의- 또는- 아미노기 및- 카르복실기로 부터 각각 하나의 수소원자 또는 히드록실기를 제거함으로써 형성된 아미노산 잔류물(- 글히드록시리신의 잔류물은 제외)이며, 상기 아미노산 잔류물은 인접 아미노기와 아미드 결합을 형성한다. 그리고 R3와 R4는 같거나 다르며 각각 아미노기를 위한 보호기이다)로 표시되는 10-아미노아실 -1,5-di 보호 -1,5,10- 트리아자데칸과 용축시켜 일반식 :(상기 식에서, R1,R2',R3,R4및 m은 앞서 정의한 바와 같다)로 표시되는 화합물을 얻고 생성된 화합물로부터 보호기들을 제거하는 것을 포함하는 일반식 :(상기 식에서, R1과 m은 앞서 정의한 바와 같고, R2는- 또는- 아미노산의- 또는- 아미노기 및 카르복실기로 부터 각각 하나의 수소원자 및 히드록실기를 제거함으로써 형성된 아미노산 잔류물(- 히드록시글리신의 잔류물은 제외)이며, 상기 아미노산 잔류물은 인접한 카르보닐기 및 아미노기와 산 아미드 결합을 형성한다)로 표시되는 화합물의 제조방법.
- 제8항에 있어서 일반식(Ⅶ)의 화합물이 7-구아니디노헵탄산 또는 3- 히드록시 -7- 구아니디노헵탄산이고, 일반식(Ⅵ)의 화합물이 10- 글리실 -1,5-di 보호 -1,5,10- 트리아자데칸 또는 10-L- 세릴 또는 10-0- 보호 -L- 세릴 -1,5-di 보호 -1,5,10- 트리아자데칸인 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP151698 | 1982-09-02 | ||
| JP57151698A JPS5942356A (ja) | 1982-09-02 | 1982-09-02 | スパガリン関連化合物およびその製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR840006332A true KR840006332A (ko) | 1984-11-29 |
| KR900008137B1 KR900008137B1 (ko) | 1990-10-31 |
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ID=15524303
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019830004071A KR900008137B1 (ko) | 1982-09-02 | 1983-08-30 | 스페르구알린-관련 화합물의 제조방법 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4529549A (ko) |
| EP (1) | EP0105193B1 (ko) |
| JP (1) | JPS5942356A (ko) |
| KR (1) | KR900008137B1 (ko) |
| AR (1) | AR241650A1 (ko) |
| AT (1) | ATE36701T1 (ko) |
| AU (1) | AU560073B2 (ko) |
| CA (1) | CA1199641A (ko) |
| CS (1) | CS235341B2 (ko) |
| DE (1) | DE3377795D1 (ko) |
| DK (1) | DK160089C (ko) |
| ES (1) | ES8506267A1 (ko) |
| HU (1) | HU190730B (ko) |
| MX (1) | MX8257A (ko) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5862152A (ja) * | 1981-10-08 | 1983-04-13 | Microbial Chem Res Found | Ｎ−〔４−（３−アミノプロピル）アミノブチル〕−２−（ω−グアニジノ脂肪酸アミド）−２−ヒドロキシエタンアミドおよびその誘導体ならびにその製造法 |
| JPS61129119A (ja) * | 1984-11-13 | 1986-06-17 | Microbial Chem Res Found | 新規免疫抑制剤 |
| JPS61165322A (ja) * | 1985-01-14 | 1986-07-26 | Microbial Chem Res Found | スパガリン類の注射用凍結乾燥製剤 |
| JPH075538B2 (ja) * | 1985-08-27 | 1995-01-25 | 財団法人微生物化学研究会 | フエニレン基を有するスパガリン関連ニトリル化合物及びその製造法 |
| EP0241797B1 (en) * | 1986-04-04 | 1991-06-12 | Microbial Chemistry Research Foundation | Novel spergualin-related compounds and process for producing the same |
| EP0284632A1 (en) * | 1987-03-30 | 1988-10-05 | Shosuke Okamoto | Phenylalanine derivative and proteinase inhibitor |
| JPH0794424B2 (ja) * | 1987-09-30 | 1995-10-11 | 財団法人微生物化学研究会 | 新スパガリン関連化合物およびその製造法 |
| US5061787A (en) * | 1988-06-24 | 1991-10-29 | Nippon Kayaku Kabushiki Kaisha | Novel spergualin-related compounds and compositions |
| JPH0776204B2 (ja) * | 1988-07-01 | 1995-08-16 | 寳酒造株式会社 | スパガリン類の精製法 |
| US4879313A (en) * | 1988-07-20 | 1989-11-07 | Mosanto Company | Novel platelet-aggregation inhibitors |
| EP0467280B1 (en) * | 1990-07-20 | 1994-09-28 | Nippon Kayaku Kabushiki Kaisha | Novel spergualin-related compound and use thereof |
| WO1994004140A1 (en) * | 1992-08-19 | 1994-03-03 | Nippon Kayaku Kabushiki Kaisha | Antiprotozoan drug |
| FR2698628B1 (fr) * | 1992-12-02 | 1995-02-17 | Fournier Ind & Sante | Analogues de 15-déoxyspergualine, leur procédé de préparation et leur utilisation en thérapeutique. |
| FR2716451B1 (fr) * | 1994-02-24 | 1996-04-26 | Fournier Ind & Sante | Analogues de la 15-déoxyspergualine, leur procédé de préparation et leur utilisation en thérapeutique. |
| FR2716452B1 (fr) * | 1994-02-24 | 1996-05-10 | Fournier Ind & Sante | Analogues de la 15-déoxyspergualine, leur procédé de préparation et leur utilisation en thérapeutique. |
| FR2737891B1 (fr) * | 1995-08-17 | 1997-10-24 | Fournier Ind & Sante | Analogues chiraux de la 15-deoxyspergualine, procede de preparation et utilisation en therapeutique |
| DK0755380T3 (da) * | 1995-02-10 | 1999-06-23 | Fournier Ind & Sante | 15-deoxyspergualin-analoge, deres terapeutiske anvendelse og fremgangsmåde til fremstilling deraf |
| FR2730488B1 (fr) * | 1995-02-10 | 1997-04-30 | Fournier Ind & Sante | Analogues de la 15-deoxyspergualine, leur utilisation en therapeutique et leur procede de preparation |
| FR2734263B1 (fr) * | 1995-05-17 | 1997-06-20 | Fournier Ind & Sante | Analogues de la 15-deoxyspergualine, leur procede de preparation et leur utilisation en therapeutique |
| US20020142000A1 (en) * | 1999-01-15 | 2002-10-03 | Digan Mary Ellen | Anti-CD3 immunotoxins and therapeutic uses therefor |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3737443A (en) * | 1969-04-02 | 1973-06-05 | Taiho Pharmaceutical Co Ltd | Omega-guanidino acid amide derivatives and manufacturing the same |
| JPS507057B1 (ko) * | 1970-10-28 | 1975-03-20 | ||
| US3937805A (en) * | 1971-11-10 | 1976-02-10 | Colgate-Palmolive Company | Method of making dentifrice compositions containing insolubilized salts of 1,6-di-(p-chlorophenyl biguanido) hexane |
| JPS5748957A (en) * | 1980-09-08 | 1982-03-20 | Microbial Chem Res Found | Novel antibiotic bmg 162-af2, its preparation and carcinostatic agent comprising it as active ingredient |
| CH648289A5 (de) * | 1981-05-11 | 1985-03-15 | Microbial Chem Res Found | N-(4-(3-aminopropyl)-aminobutyl)-2,2-dihydroxyaethanamid und verfahren zu seiner synthese. |
-
1982
- 1982-09-02 JP JP57151698A patent/JPS5942356A/ja active Granted
-
1983
- 1983-08-17 AU AU18074/83A patent/AU560073B2/en not_active Ceased
- 1983-08-18 US US06/524,354 patent/US4529549A/en not_active Expired - Lifetime
- 1983-08-30 KR KR1019830004071A patent/KR900008137B1/ko not_active IP Right Cessation
- 1983-08-31 EP EP83108567A patent/EP0105193B1/en not_active Expired
- 1983-08-31 AR AR83294077A patent/AR241650A1/es active
- 1983-08-31 AT AT83108567T patent/ATE36701T1/de not_active IP Right Cessation
- 1983-08-31 ES ES525278A patent/ES8506267A1/es not_active Expired
- 1983-08-31 DE DE8383108567T patent/DE3377795D1/de not_active Expired
- 1983-09-01 DK DK398583A patent/DK160089C/da active
- 1983-09-01 CA CA000435865A patent/CA1199641A/en not_active Expired
- 1983-09-01 HU HU833047A patent/HU190730B/hu not_active IP Right Cessation
- 1983-09-02 MX MX825783A patent/MX8257A/es unknown
- 1983-09-02 CS CS836397A patent/CS235341B2/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK160089C (da) | 1991-06-24 |
| HU190730B (en) | 1986-10-28 |
| DK398583A (da) | 1984-03-03 |
| CA1199641A (en) | 1986-01-21 |
| KR900008137B1 (ko) | 1990-10-31 |
| EP0105193A2 (en) | 1984-04-11 |
| DK160089B (da) | 1991-01-28 |
| AU1807483A (en) | 1984-03-08 |
| US4529549A (en) | 1985-07-16 |
| ES525278A0 (es) | 1985-07-01 |
| MX8257A (es) | 1994-01-31 |
| ES8506267A1 (es) | 1985-07-01 |
| EP0105193B1 (en) | 1988-08-24 |
| ATE36701T1 (de) | 1988-09-15 |
| JPS5942356A (ja) | 1984-03-08 |
| AR241650A1 (es) | 1992-10-30 |
| AU560073B2 (en) | 1987-03-26 |
| DE3377795D1 (en) | 1988-09-29 |
| JPH0149256B2 (ko) | 1989-10-24 |
| DK398583D0 (da) | 1983-09-01 |
| CS235341B2 (en) | 1985-05-15 |
| EP0105193A3 (en) | 1985-04-03 |
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