KR850006391A - 벤조치아졸 및 벤조치오펜 유도체의 제조방법 - Google Patents
벤조치아졸 및 벤조치오펜 유도체의 제조방법 Download PDFInfo
- Publication number
- KR850006391A KR850006391A KR1019850001704A KR850001704A KR850006391A KR 850006391 A KR850006391 A KR 850006391A KR 1019850001704 A KR1019850001704 A KR 1019850001704A KR 850001704 A KR850001704 A KR 850001704A KR 850006391 A KR850006391 A KR 850006391A
- Authority
- KR
- South Korea
- Prior art keywords
- compound
- formula
- general formula
- benzothiazol
- preparing
- Prior art date
Links
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 title claims 5
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical class C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 title claims 4
- 238000000034 method Methods 0.000 title claims 2
- 239000002253 acid Substances 0.000 claims 9
- 150000001875 compounds Chemical class 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 6
- -1 methylenedioxy Chemical group 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 150000008065 acid anhydrides Chemical class 0.000 claims 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 150000004820 halides Chemical class 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- PPHWLBSKIZAYHA-UHFFFAOYSA-N 4-chloro-n'-hydroxy-5,6-dimethoxy-1-benzothiophene-2-carboximidamide Chemical compound ClC1=C(OC)C(OC)=CC2=C1C=C(C(=N)NO)S2 PPHWLBSKIZAYHA-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- HAMNKKUPIHEESI-UHFFFAOYSA-N aminoguanidine Chemical compound NNC(N)=N HAMNKKUPIHEESI-UHFFFAOYSA-N 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles 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 in position 2
-
- 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
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D333/56—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D333/58—Radicals substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D333/60—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 carbon atoms of the hetero ring
- C07D333/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D333/70—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (5)
- 일반식 Ⅰ인 산 또는 그 산할라이드나 그 산무수물과 일반식 Ⅲ 또는 일반식 V인 화합물을 반응시킴을 특징으로 하는 일반식 I의 벤조치아졸 및 벤조치오펜 유도체와 그의 약학적으로 허용되는 산부가염을 제조하는 방법.식중 R1은 알킬(Cl-6), 알콕시(C1-6) 하이드록시, 할로겐, NO2, CF3또는 -NR5R6중에서 선택된 동일 또는 서로 다른 1-4개의 치환기이거나 두개의 치환기가 메틸렌디옥시 그룹을 형성한 것이고 X는 니트로겐(N), 또는그룹이고, n은 0,1 또는 2이고, R3는,이고, R3가인 경우는 X가 니트로겐이고 R1이 하이드록시, 알콕시(Cl-6), 메틸렌디옥시로부터 선택된 치환기들로 제한되는 조건하에서만이며, R4,R6,R6는 수소 또는 알킬(Cl-6)이며, 일반식 Ⅲ,V화합물은 그 반응성 유도체와 수소가 알카리금속같은 좀더 반응성이 큰 것으로 치환된 것일 수 있다.
- 일반식 Ⅱ인 산 또는 그 산할라이드나 그 산무수물과 알카리금속아지드를 반응시켜 생성된 아지드화합물을 훤원시킴을 특징으로 하는 일반식 I의 벤조치아졸 및 벤조치아펜 유도체와 그의 약학적으로 허용되는 산부가염을 제조하는 방법.식중 R1,R3,n 및 X는 전술한 바와 같다.
- 일반식 Ⅳ화합물과 일반식 V화합물을 반응시킴을 특징으로 하는 일반식 I의 벤조치아졸 및 벤조치오펜 유도체와 그의 약학적으로 허용되는 산부가염을 제조하는 방법.식중, R1,R3,X,n 및 R5는 전술한 바와 같다.
- 일반식 Ⅵ화합물과 아미노구아니딘(Ⅶ) 또는 그의 염과 반응시킴을 특징으로 하는 일반식 I의 벤조치아졸 및 벤조치오펜 유도체와 그의 약학적으로 허용되는 산부가염을 제조하는 방법.식중 R1,R3,n 및 X는 전술한 바와 같다.
- 제1, 제2, 제3, 제4항에서 일반식 I의 화합물이 N-하이드록시-5,6-디메톡시-벤조(b)치오펜-2-카복시미드아미드, 4-클로로-N-하이드록시-5,6-디메톡시-벤조(b)치오펜-2-카복시미드아미드, 5,6-디메톡시-벤조(b)치오젠-2--카복사미드 또는 그들의 약학적으로 허용되는 산부가염인 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB848406906A GB8406906D0 (en) | 1984-03-16 | 1984-03-16 | Benzo-thiazole and benzothiophene derivatives |
GB84.06906 | 1984-03-16 |
Publications (2)
Publication Number | Publication Date |
---|---|
KR850006391A true KR850006391A (ko) | 1985-10-05 |
KR870000920B1 KR870000920B1 (ko) | 1987-05-07 |
Family
ID=10558202
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019850001704A KR870000920B1 (ko) | 1984-03-16 | 1985-03-16 | 벤조 치오펜 유도체의 제조 방법 |
Country Status (14)
Country | Link |
---|---|
US (2) | US4665206A (ko) |
EP (1) | EP0158380B1 (ko) |
JP (1) | JPS60209577A (ko) |
KR (1) | KR870000920B1 (ko) |
AU (1) | AU568428B2 (ko) |
CA (1) | CA1254216A (ko) |
DE (1) | DE3567459D1 (ko) |
DK (1) | DK119285A (ko) |
ES (4) | ES8707223A1 (ko) |
FI (1) | FI80883C (ko) |
GB (1) | GB8406906D0 (ko) |
HU (1) | HU198030B (ko) |
IE (1) | IE57977B1 (ko) |
ZA (1) | ZA851807B (ko) |
Families Citing this family (40)
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IE58555B1 (en) * | 1984-12-10 | 1993-10-06 | Warner Almbert Company | Novel benzothiophenes and benzofurans having antiallergy activity |
EP0253650A3 (en) * | 1986-07-18 | 1989-09-13 | Eli Lilly And Company | Improvements relating to benzothiophene derivatives |
US4873259A (en) * | 1987-06-10 | 1989-10-10 | Abbott Laboratories | Indole, benzofuran, benzothiophene containing lipoxygenase inhibiting compounds |
US4822809A (en) * | 1987-11-13 | 1989-04-18 | Abbott Laboratories | Benzazole lipoxygenase inhibiting compounds |
US4882354A (en) * | 1987-12-16 | 1989-11-21 | Norwich Eaton Pharmaceuticals, Inc. | N-hydroxy-5-phenyl-2-furancarboximidamides useful as cardiotonic agents |
DE68901424D1 (de) * | 1988-07-05 | 1992-06-11 | Akzo Nv | Verbindungen mit bronchodilatatorischer aktivitaet. |
US5276052A (en) * | 1990-10-26 | 1994-01-04 | Akzo N.V. | Use of a benzo[b]thiopene-2-carboximidamide derivative |
IE913683A1 (en) * | 1990-10-26 | 1992-05-22 | Akzo Nv | USE OF A BENZO[b]THIOPHENE-2-CARBOXIMIDAMIDE DERIVATIVE |
DE4128871A1 (de) * | 1991-08-30 | 1993-03-04 | Boehringer Mannheim Gmbh | Benzo(b)thiophenderivate, verfahren zu ihrer herstellung und arzneimittel |
US5340833A (en) * | 1992-05-01 | 1994-08-23 | Eisai Co., Ltd. | Urokinase inhibitors |
US5436246A (en) * | 1992-09-17 | 1995-07-25 | Merrell Dow Pharmaceuticals Inc. | Serotonin receptor agents |
AU683552B2 (en) * | 1994-04-11 | 1997-11-13 | Chugai Seiyaku Kabushiki Kaisha | 4,6-DI-t-butyl-2,3-dihydrobenzothiophene derivative |
US5863936A (en) * | 1995-04-18 | 1999-01-26 | Geron Corporation | Telomerase inhibitors |
US5703116A (en) * | 1995-04-18 | 1997-12-30 | Geron Corporation | Telomerase Inhibitors |
US5760062A (en) * | 1995-04-18 | 1998-06-02 | Geron Corporation | Telomerase inhibitors |
US5656638A (en) * | 1995-04-18 | 1997-08-12 | Geron Corporation | Telomerase inhibitors |
US5770613A (en) * | 1995-09-29 | 1998-06-23 | Geron Corporation | Telomerase inhibitors |
US5767278A (en) * | 1995-10-06 | 1998-06-16 | Geron Corporation | Telomerase inhibitors |
US6362216B1 (en) | 1998-10-27 | 2002-03-26 | Array Biopharma Inc. | Compounds which inhibit tryptase activity |
CA2715683A1 (en) | 1999-08-21 | 2001-03-01 | Nycomed Gmbh | Synergistic combination |
ES2427930T3 (es) | 2001-05-23 | 2013-11-04 | Mitsubishi Tanabe Pharma Corporation | Composición terapéutica para el tratamiento regenerativo de enfermedades de los cartílagos |
WO2002094321A1 (fr) | 2001-05-23 | 2002-11-28 | Tanabe Seiyaku Co., Ltd. | Compositions favorisant la guérison d'une fracture osseuse |
US7772188B2 (en) | 2003-01-28 | 2010-08-10 | Ironwood Pharmaceuticals, Inc. | Methods and compositions for the treatment of gastrointestinal disorders |
AU2004226353A1 (en) | 2003-04-01 | 2004-10-14 | Laboratoires Serono Sa | Inhibitors of phosphodiesterases in infertility |
JP2007508318A (ja) * | 2003-10-09 | 2007-04-05 | エートン ファーマ インコーポレーティッド | チオフェンおよびベンゾチオフェンヒドロキサム酸誘導体 |
WO2006101454A1 (en) * | 2005-03-21 | 2006-09-28 | S*Bio Pte Ltd | Benzothiophene derivatives: preparation and pharmaceutical applications |
MY148644A (en) * | 2005-07-18 | 2013-05-15 | Orion Corp | New pharmaceutical compounds |
US20090221564A1 (en) * | 2006-02-21 | 2009-09-03 | Trigen Limited | Heterocyclic Compounds and Their Use in the Treatment of Cardiovascular Disease |
WO2008083124A1 (en) | 2006-12-28 | 2008-07-10 | Rigel Pharmaceuticals, Inc. | N-substituted-heterocycloalkyloxybenzamide compounds and methods of use |
US8969514B2 (en) | 2007-06-04 | 2015-03-03 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia, atherosclerosis, coronary heart disease, gallstone, obesity and other cardiovascular diseases |
AU2009270833B2 (en) | 2008-07-16 | 2015-02-19 | Bausch Health Ireland Limited | Agonists of guanylate cyclase useful for the treatment of gastrointestinal, inflammation, cancer and other disorders |
US9616097B2 (en) | 2010-09-15 | 2017-04-11 | Synergy Pharmaceuticals, Inc. | Formulations of guanylate cyclase C agonists and methods of use |
JP6251038B2 (ja) | 2011-03-01 | 2017-12-20 | シナジー ファーマシューティカルズ インコーポレイテッド | グアニル酸シクラーゼcアゴニストの調製方法 |
AU2014218599C1 (en) | 2013-02-25 | 2018-09-06 | Bausch Health Ireland Limited | Guanylate cyclase receptor agonists for use in colonic cleansing |
CA2905435A1 (en) | 2013-03-15 | 2014-09-25 | Synergy Pharmaceuticals Inc. | Compositions useful for the treatment of gastrointestinal disorders |
JP2016514671A (ja) | 2013-03-15 | 2016-05-23 | シナジー ファーマシューティカルズ インコーポレイテッド | グアニル酸シクラーゼのアゴニストおよびその使用 |
US10011637B2 (en) | 2013-06-05 | 2018-07-03 | Synergy Pharmaceuticals, Inc. | Ultra-pure agonists of guanylate cyclase C, method of making and using same |
JP6694385B2 (ja) | 2013-08-09 | 2020-05-13 | アーデリクス,インコーポレーテッド | リン酸塩輸送阻害のための化合物及び方法 |
JP2022533251A (ja) | 2019-05-21 | 2022-07-21 | アルデリックス, インコーポレイテッド | 患者において血清リン酸塩を低下させるための組み合わせ |
CN111296447B (zh) * | 2020-03-24 | 2021-09-17 | 东营施普瑞石油工程技术有限公司 | 一种油田用杀菌剂及其制备方法 |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
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GB438211A (en) * | 1934-06-01 | 1935-11-13 | Ig Farbenindustrie Ag | The manufacture of heterocyclic compounds |
US2775593A (en) * | 1948-10-01 | 1956-12-25 | Schenley Ind Inc | Thiosemicarbazones of aldehydes and ketones of the heterocyclic series |
GB1231170A (ko) * | 1967-12-15 | 1971-05-12 | ||
BE759237A (fr) * | 1969-11-21 | 1971-05-01 | Montedison Spa | Procede de preparation d'amides a partir de composes heterocycliques azotes |
BE786520A (fr) * | 1971-07-23 | 1973-01-22 | Bayer Ag | Nouveaux benzothiazoles substitues, leur preparation et leur application comme fongicides et bactericides |
DE2258036A1 (de) * | 1972-11-27 | 1974-05-30 | Goedecke Ag | Verfahren zur herstellung von benzo eckige klammer auf b eckige klammer zu thiophen-derivaten |
FR2305982A1 (fr) * | 1975-04-03 | 1976-10-29 | Innothera Lab Sa | Nouvelles benzothienyl amino (propyl et butyl) cetones, leur procede de preparation et leur application en therapeutique |
CH636866A5 (de) * | 1977-08-15 | 1983-06-30 | Lilly Co Eli | Thiadiazolylbenzamide und sie enthaltende insektizide mittel. |
US4140785A (en) * | 1978-05-08 | 1979-02-20 | E. I. Du Pont De Nemours And Company | N-(benzothienopyrazol)amide antirhinoviral agents |
JPS5936670A (ja) * | 1982-08-25 | 1984-02-28 | Takeda Chem Ind Ltd | ベンゾチアゾ−ル誘導体,その製造法およびそれを含有する摂食抑制剤 |
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1984
- 1984-03-16 GB GB848406906A patent/GB8406906D0/en active Pending
-
1985
- 1985-03-06 EP EP85200325A patent/EP0158380B1/en not_active Expired
- 1985-03-06 DE DE8585200325T patent/DE3567459D1/de not_active Expired
- 1985-03-07 IE IE592/85A patent/IE57977B1/en not_active IP Right Cessation
- 1985-03-07 US US06/709,396 patent/US4665206A/en not_active Expired - Fee Related
- 1985-03-11 CA CA000476161A patent/CA1254216A/en not_active Expired
- 1985-03-11 ZA ZA851807A patent/ZA851807B/xx unknown
- 1985-03-14 AU AU39852/85A patent/AU568428B2/en not_active Ceased
- 1985-03-15 JP JP60052167A patent/JPS60209577A/ja active Granted
- 1985-03-15 ES ES541336A patent/ES8707223A1/es not_active Expired
- 1985-03-15 DK DK119285A patent/DK119285A/da not_active Application Discontinuation
- 1985-03-15 FI FI851038A patent/FI80883C/fi not_active IP Right Cessation
- 1985-03-15 HU HU85968A patent/HU198030B/hu not_active IP Right Cessation
- 1985-03-16 KR KR1019850001704A patent/KR870000920B1/ko not_active IP Right Cessation
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1986
- 1986-01-27 ES ES551281A patent/ES8704926A1/es not_active Expired
- 1986-01-27 ES ES551282A patent/ES8704924A1/es not_active Expired
- 1986-01-27 ES ES551280A patent/ES8704925A1/es not_active Expired
-
1989
- 1989-04-06 US US07/333,806 patent/US4929636A/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
EP0158380B1 (en) | 1989-01-11 |
ES8707223A1 (es) | 1987-07-16 |
ES8704924A1 (es) | 1987-04-16 |
US4929636A (en) | 1990-05-29 |
DK119285A (da) | 1985-09-17 |
CA1254216A (en) | 1989-05-16 |
ES551282A0 (es) | 1987-04-16 |
DE3567459D1 (en) | 1989-02-16 |
KR870000920B1 (ko) | 1987-05-07 |
ES551280A0 (es) | 1987-04-16 |
ES541336A0 (es) | 1987-07-16 |
EP0158380A1 (en) | 1985-10-16 |
JPH0588232B2 (ko) | 1993-12-21 |
HU198030B (en) | 1989-07-28 |
AU3985285A (en) | 1985-09-19 |
GB8406906D0 (en) | 1984-04-18 |
FI80883C (fi) | 1990-08-10 |
DK119285D0 (da) | 1985-03-15 |
US4665206A (en) | 1987-05-12 |
ZA851807B (en) | 1985-10-30 |
JPS60209577A (ja) | 1985-10-22 |
AU568428B2 (en) | 1987-12-24 |
ES551281A0 (es) | 1987-04-16 |
IE850592L (en) | 1985-09-16 |
FI80883B (fi) | 1990-04-30 |
ES8704926A1 (es) | 1987-04-16 |
FI851038L (fi) | 1985-09-17 |
FI851038A0 (fi) | 1985-03-15 |
IE57977B1 (en) | 1993-06-02 |
HUT37410A (en) | 1985-12-28 |
ES8704925A1 (es) | 1987-04-16 |
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