KR840008363A - 크로몬-및 티오크로몬-치환된 1,4-디하이드로-피리딘-락톤의 제조방법 - Google Patents
크로몬-및 티오크로몬-치환된 1,4-디하이드로-피리딘-락톤의 제조방법 Download PDFInfo
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- KR840008363A KR840008363A KR1019840001520A KR840001520A KR840008363A KR 840008363 A KR840008363 A KR 840008363A KR 1019840001520 A KR1019840001520 A KR 1019840001520A KR 840001520 A KR840001520 A KR 840001520A KR 840008363 A KR840008363 A KR 840008363A
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- alkyl
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- 238000000034 method Methods 0.000 title claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 9
- -1 benzylidene compound Chemical class 0.000 claims 7
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- 239000003153 chemical reaction reagent Substances 0.000 claims 5
- 239000003960 organic solvent Substances 0.000 claims 5
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 4
- 150000002081 enamines Chemical class 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000003282 alkyl amino group Chemical group 0.000 claims 3
- 125000004414 alkyl thio group Chemical group 0.000 claims 3
- 125000004122 cyclic group Chemical group 0.000 claims 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims 3
- 125000001153 fluoro group Chemical group F* 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 150000002576 ketones Chemical class 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 125000006239 protecting group Chemical group 0.000 claims 3
- 150000001299 aldehydes Chemical class 0.000 claims 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 229910052717 sulfur Chemical group 0.000 claims 2
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims 1
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical compound C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 claims 1
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims 1
- 229910002651 NO3 Inorganic materials 0.000 claims 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- AHIBWURJLGCHAY-UHFFFAOYSA-N [S].C1=CC=CC=C1 Chemical compound [S].C1=CC=CC=C1 AHIBWURJLGCHAY-UHFFFAOYSA-N 0.000 claims 1
- 125000006241 alcohol protecting group Chemical group 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- PGRHXDWITVMQBC-UHFFFAOYSA-N dehydroacetic acid Natural products CC(=O)C1C(=O)OC(C)=CC1=O PGRHXDWITVMQBC-UHFFFAOYSA-N 0.000 claims 1
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims 1
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- PEQJBOMPGWYIRO-UHFFFAOYSA-N n-ethyl-3,4-dimethoxyaniline Chemical compound CCNC1=CC=C(OC)C(OC)=C1 PEQJBOMPGWYIRO-UHFFFAOYSA-N 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 125000005936 piperidyl group Chemical group 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 239000011593 sulfur Chemical group 0.000 claims 1
- 125000004665 trialkylsilyl group Chemical group 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
-
- 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
- A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
-
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- 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
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D307/66—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Cardiology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pyridine Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Saccharide Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Polyesters Or Polycarbonates (AREA)
- Steroid Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
내용 없음.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (5)
- 일반식(II)의 알데히드를 적절하게는 불활성 유기용매의 존재하에 20°내지 150℃에서 일반식(III)의 엔아민 및 일반식(IV)의 케톤과 반응시키고 Z가-O-B일 경우 적합한 시약으로 보호그룹을 제거하거나 일반식(II)의 알데히드를 적절하게는 불활성 유기 용매의 존재하에 20°내지 150℃에서 일반식(V)에 케톤 및 일반식(VI)의 엔아민과 반응시키고 Z가-O-B일 경우 적합한 시약으로 보호그룹을 제거하거나, 일반식(VII)의 일리덴 화합물을 적절하게는 불활성 유기 용매의 존재하에 20°내지 150℃에서 일반식(VI)의 엔아민과 반응시고 Z가-O-B일 경우 적합한 시약으로 보호그룹을 분리 제거하거나; 일반식(II)와 알데히드를 적절하게 불활성 유기 용매의 존재하에 20°내지 150℃에서 일반식(V)의 케톤 및 일반식(VIII)의 테트론산 아미드와 반응시키거나; 일반식(IX)의 벤질리덴 화합물을 적절하게 불활성 유기용매의 존재하에 20°내지 150℃에서 일반식(III)의 엔아민과 반응시키고 Z가-O-B일 경우 적합한 시약으로분리제거함을 특징으로 하여, 일반식(I)의 디하이드로피리딘 및 그의 약제학적으로 무독한 염을 제조하는 방법.상기식에서, R1은 수소, C1내지 C10의 직쇄, 사이클릭 또는 측쇄지방족 탄화수소라디칼, 카복실산 알킬에스테르(여기서 라디칼은 C1내지 C10임)이거나, 할로겐, (C1내지 C10) 알킬, (C1내지 C10)알콕시, (C1내지 C10)알킬티오, (C1내지 C5)알킬설피닐, 시아노, 하이드록실, 니트로, 모노-또는 폴리-플루오로 (C1내지 C5)알킬, 모노-또는 폴리-플루오로 (C1내지 C5) 알콕시, 모노-또는 폴리-플루오로 (C1내지 C5)알킬티오, 아미노모노-(C1내지 C5) 알킬아미노 및 디-(C1내지 C5) 알킬아미노로 이루어진 그룹에서 선택된 1내지 5개의 같거나 다른 치환체로 임의 치환될 수 있는 방향족 또는 헤테로방향족 라디칼이고; R2는 1내지 3개의 할로겐원자 또는 수소이며; R4는 C1내지 C10알콕시, C1내지 C10알킬티오, C1내지 C10알킬설피닐, 각각의 알킬기가 C1내지 C6인 트리알킬실릴, 할로겐, 시아노, 하이드록실, 아미노, C1내지 C6알킬아미노, 각각의 알킬기가 C1내지 C6인 디알킬아미노, 몰폴리닐, 피페리딜, 피페라지닐, 니트로, 니트레이트, 아릴 또는 헤테로 아릴 (여기서, 아릴 또는 헤테로아릴 라디칼은 할로겐, C1내지 C6의 알킬, C1내지 C6의 알콕시, C1내지 C6의 알킬티오, C1내지 C6의 알킬설피닐, C1내지 C6의 알킬설포닐, 하이드록실, 시아노, 니트로, 아미노, C1내지 C6의 알킬아미노, 각각의 알킬기가 C1내지 C6인 디알킬아미노, C1내지 C6의 모노-또는 폴리-플루오로알킬 및 C1내지 C6의 모노-또는 폴리-플루오로알콕시로 이루어진 그룹에서 선택된 1내지 3개의 같거나 다른 치환체의 임의 치환될 수 있다)로 임의 치환된 C1내지 C20의 포화 또는 불포화된 직쇄, 축쇄 또는 사이클릭 탄화수소 라디칼이고, R5는 수소이거나 임의로 O, CO, NH, N-C1내지 C8의 알킬, S 및 S02로 이루어진 그룹에서 선택된 1 또는 2개의 같거나 다른 헤테로 쇄원을 함유하며 할로겐, 니트로, 시아노, 아지도, 하이드록실, 아릴, 헤테로아릴, 아미노 또는 각각의 알킬기가 C1-C6인 모노알킬아미노 또는 디알킬아미노로 임의 치환된 C1내지 C10의 포화 또는 불포화된 직쇄, 축쇄 또는 사이클릭지방족 알킬 라디칼이며, R6는 수소이거나 C1-C10-알콕시, 할로겐 또는 몰폴리노로 임의 치환된 직쇄 또는 축쇄, C1-C20-알킬 라디칼이고, A는 직접 결합을 나타내거나 산소 또는 황으로 임의 차단될 수 있는 C1-C20-알킬렌쇄 또는 C2-C20-알케닐렌쇄이며, X는 산소 또는 황이고, Y는 직접결합을 나타내거나, O, S, -NH-또는 -N-C1-C6알킬이며, R7은 C1내지 C8알킬이며, R7은 C1내지 C6알킬 쇄이고, Z는 할로겐 또는 -O-B(여기서, B는또는 -Si (알킬)3와 같은 알코올-보호그룹이다).
- 제1항 있어서, 동몰량의 반응물을 반응시킴을 특징으로 하는 방법.
- 제1항에 있어서, 일반식(III), (V) 및 (VI)의 화합물을 3몰까지의 과량으로 사용함을 특징으로 하는 방법.
- 제1항에 있어서, 반응 온도를 30°내지 120℃로 하여 수행함을 특징으로 하는 방법.
- 제1항에 있어서, 반응 온도를 용매의 비점으로 하여 수행함을 특징으로 하는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP311003.4 | 1983-03-25 | ||
| DE19833311003 DE3311003A1 (de) | 1983-03-25 | 1983-03-25 | Chromon- und thiochromonsubstituierte 1,4-dihydropyridinlactone, mehrere verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln |
| DEP3311003.4 | 1983-03-25 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR840008363A true KR840008363A (ko) | 1984-12-14 |
| KR920001137B1 KR920001137B1 (ko) | 1992-02-06 |
Family
ID=6194710
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019840001520A KR920001137B1 (ko) | 1983-03-25 | 1984-03-24 | 크로몬- 및 티오크로몬-치환된 1,4-디하이드로-피리딘-락톤의 제조방법 |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4555512A (ko) |
| EP (1) | EP0123095B1 (ko) |
| JP (1) | JPS59193887A (ko) |
| KR (1) | KR920001137B1 (ko) |
| AT (1) | ATE38229T1 (ko) |
| AU (1) | AU564838B2 (ko) |
| CA (1) | CA1211109A (ko) |
| DE (2) | DE3311003A1 (ko) |
| DK (1) | DK158950C (ko) |
| ES (5) | ES8607307A1 (ko) |
| FI (1) | FI81100C (ko) |
| GR (1) | GR81924B (ko) |
| HU (1) | HU189849B (ko) |
| IE (1) | IE57039B1 (ko) |
| IL (1) | IL71314A (ko) |
| NO (1) | NO160659C (ko) |
| NZ (1) | NZ207588A (ko) |
| PH (1) | PH20322A (ko) |
| PT (1) | PT78311B (ko) |
| ZA (1) | ZA842166B (ko) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4011105A1 (de) * | 1990-04-06 | 1991-10-10 | Bayer Ag | Neue 4-chinolyl-dihydropyridine, verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln |
| US5204472A (en) * | 1990-04-06 | 1993-04-20 | Bayer Aktiengesellschaft | Quinoline and isoquinoline intermediates |
| DE4313696A1 (de) * | 1993-04-27 | 1994-11-03 | Bayer Ag | 2-Amino-4-heteroaryl-1,4-dihydropyridine, Verfahren zu ihrer Herstellung und ihre Verwendung in Arzneimitteln |
| AU2004272078A1 (en) * | 2003-09-10 | 2005-03-24 | Synta Pharmaceuticals Corp. | Dihydropyridine compounds for treating or preventing metabolic disorders |
| DE102005034264A1 (de) | 2005-07-22 | 2007-02-01 | Bayer Healthcare Ag | 4-Chromenonyl-1,4-dihydropyridincarbonitrile und ihre Verwendung |
| DE102005034267A1 (de) | 2005-07-22 | 2007-01-25 | Bayer Healthcare Ag | 4-Chromenonyl-1,4-dihydropyridine und ihre Verwendung |
| EP2039678A1 (de) | 2007-09-18 | 2009-03-25 | Bayer CropScience AG | Verfahren zum Herstellen von 4-Aminobut-2-enoliden |
| EP2042496A1 (de) | 2007-09-18 | 2009-04-01 | Bayer CropScience AG | Verfahren zur Herstellung von 4-Aminobut-2-enoliden |
| EP2230236A1 (de) | 2009-03-16 | 2010-09-22 | Bayer CropScience AG | Neues Verfahren zur Herstellung von Enaminocarbonyl-Verbindungen |
| EP2230237A1 (de) | 2009-03-16 | 2010-09-22 | Bayer CropScience AG | Neues Verfahren zur Herstellung von Enaminocarbonyl-Verbindungen |
| TW201111370A (en) | 2009-08-18 | 2011-04-01 | Bayer Cropscience Ag | Novel process for the preparation of 4-aminobut-2-enolides |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ201395A (en) * | 1981-07-30 | 1987-02-20 | Bayer Ag | Pharmaceutical compositions containing 1,4-dihydropyridines and certain of these dihydropyridines |
| DE3269219D1 (en) * | 1981-11-17 | 1986-03-27 | Fisons Plc | Dihydropyridines, methods for their production and their formulation and use as pharmaceuticals |
| DE3315805A1 (de) * | 1983-04-30 | 1984-11-08 | Bayer Ag, 5090 Leverkusen | Wirkstoffzubereitungen |
| DE3339861A1 (de) * | 1983-11-04 | 1985-05-15 | Bayer Ag, 5090 Leverkusen | Arzneizubereitung enthaltend dihydropyridine |
-
1983
- 1983-03-25 DE DE19833311003 patent/DE3311003A1/de not_active Withdrawn
-
1984
- 1984-02-29 DK DK144984A patent/DK158950C/da not_active IP Right Cessation
- 1984-03-12 EP EP84102659A patent/EP0123095B1/de not_active Expired
- 1984-03-12 AT AT84102659T patent/ATE38229T1/de not_active IP Right Cessation
- 1984-03-12 DE DE8484102659T patent/DE3474824D1/de not_active Expired
- 1984-03-13 NO NO840950A patent/NO160659C/no unknown
- 1984-03-14 US US06/589,614 patent/US4555512A/en not_active Expired - Lifetime
- 1984-03-21 ES ES530800A patent/ES8607307A1/es not_active Expired
- 1984-03-22 FI FI841153A patent/FI81100C/fi not_active IP Right Cessation
- 1984-03-22 IL IL71314A patent/IL71314A/xx not_active IP Right Cessation
- 1984-03-22 NZ NZ207588A patent/NZ207588A/en unknown
- 1984-03-23 PH PH30431A patent/PH20322A/en unknown
- 1984-03-23 CA CA000450361A patent/CA1211109A/en not_active Expired
- 1984-03-23 IE IE716/84A patent/IE57039B1/xx unknown
- 1984-03-23 ZA ZA842166A patent/ZA842166B/xx unknown
- 1984-03-23 HU HU841175A patent/HU189849B/hu not_active IP Right Cessation
- 1984-03-23 PT PT78311A patent/PT78311B/pt not_active IP Right Cessation
- 1984-03-23 GR GR74196A patent/GR81924B/el unknown
- 1984-03-24 JP JP59057202A patent/JPS59193887A/ja active Granted
- 1984-03-24 KR KR1019840001520A patent/KR920001137B1/ko active IP Right Grant
- 1984-03-26 AU AU26099/84A patent/AU564838B2/en not_active Ceased
-
1986
- 1986-02-21 ES ES552277A patent/ES8707952A1/es not_active Expired
- 1986-02-21 ES ES552280A patent/ES8707959A1/es not_active Expired
- 1986-02-21 ES ES552279A patent/ES8707958A1/es not_active Expired
- 1986-02-21 ES ES552278A patent/ES8707957A1/es not_active Expired
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