ES8605488A1 - Procedimiento para preparar nuevos derivados de aminotetra- lina - Google Patents

Procedimiento para preparar nuevos derivados de aminotetra- lina

Info

Publication number
ES8605488A1
ES8605488A1 ES543186A ES543186A ES8605488A1 ES 8605488 A1 ES8605488 A1 ES 8605488A1 ES 543186 A ES543186 A ES 543186A ES 543186 A ES543186 A ES 543186A ES 8605488 A1 ES8605488 A1 ES 8605488A1
Authority
ES
Spain
Prior art keywords
hydroxy
alkyl
alkoxy
hydrogen
bromine
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
ES543186A
Other languages
English (en)
Other versions
ES543186A0 (es
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
KARL mbH
Original Assignee
KARL mbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by KARL mbH filed Critical KARL mbH
Publication of ES543186A0 publication Critical patent/ES543186A0/es
Publication of ES8605488A1 publication Critical patent/ES8605488A1/es
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
    • C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D223/16—Benzazepines; Hydrogenated benzazepines
    • 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
    • C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having 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
    • C07D237/20—Nitrogen atoms
    • 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
    • A61P9/06—Antiarrhythmics
    • 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
    • A61P9/08—Vasodilators for multiple indications
    • 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
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
    • C07C205/56—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups bound to carbon atoms of six-membered aromatic rings and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
    • C07C45/513—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an etherified hydroxyl group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/753—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups
    • C07C49/755—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups a keto group being part of a condensed ring system with two or three rings, at least one ring being a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
    • C07C57/58—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • 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
    • C07D233/56—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/26—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
    • C07D243/04—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Cardiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Urology & Nephrology (AREA)
  • Vascular Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)
  • Indole Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

PROCEDIMIENTO PARA PREPARAR NUEVOS DERIVADOS DE AMINOTETRALINA. CONSISTE EN HACER REACCIONAR A UN COMPUESTO DE FORMULA (II) CON UN COMPUESTO DE FORMULA (III), EN ACETONA O DIETILETER, EN PRESENCIA DE TERC-BUTILADO POTASICO O HIDROXIDO SODICO Y DE YODURO POTASICO Y A UNA TEMPERATURA ENTRE 0J Y 150JC, PARA OBTENER UN COMPUESTO DE FORMULA (I) Y SUS SALES DE ADICION DE ACIDOS. SIENDO: A, -CH2-CH2, CHFCH- Y OTROS; B, METILENO, CARBONILO Y OTROS; R1, R3 Y R4, H, HAL, NITRO Y OTROS; R2, H, CL O BR, ALCOXI Y OTROS; R5, H, UN ALQUENILO DE C 3 A 5 Y OTROS; R1, R3 Y R4, HIDROXI, AMINO O ALQUILAMINO PROTEGIDO; R2, HIDROXI PROTEGIDO POR UN RADICAL PROTECTOR; R5, UN GRUPO PROTECTOR PARA UN GRUPO AMINO; Y U UN GRUPO LABIL NUCLEOFILO COMO HAL O UN GRUPO SULFONILOXI. SE UTILIZA PARA DISMINUIR EL EFECTO DE LA FRECUENCIA CARDIACA Y EL CONSUMO DE O2 DEL CORAZON.
ES543186A 1984-05-17 1985-05-16 Procedimiento para preparar nuevos derivados de aminotetra- lina Expired ES8605488A1 (es)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19843418270 DE3418270A1 (de) 1984-05-17 1984-05-17 Neue aminotetralinderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung

Publications (2)

Publication Number Publication Date
ES543186A0 ES543186A0 (es) 1986-03-16
ES8605488A1 true ES8605488A1 (es) 1986-03-16

Family

ID=6236070

Family Applications (3)

Application Number Title Priority Date Filing Date
ES543186A Expired ES8605488A1 (es) 1984-05-17 1985-05-16 Procedimiento para preparar nuevos derivados de aminotetra- lina
ES548921A Expired ES8607245A1 (es) 1984-05-17 1985-11-15 Procedimiento para preparar nuevos derivados de aminotetra- lina
ES548922A Expired ES8701731A1 (es) 1984-05-17 1985-11-15 Procedimiento para preparar nuevos derivados de aminotetra- lina

Family Applications After (2)

Application Number Title Priority Date Filing Date
ES548921A Expired ES8607245A1 (es) 1984-05-17 1985-11-15 Procedimiento para preparar nuevos derivados de aminotetra- lina
ES548922A Expired ES8701731A1 (es) 1984-05-17 1985-11-15 Procedimiento para preparar nuevos derivados de aminotetra- lina

Country Status (17)

Country Link
US (1) US4584293A (es)
EP (1) EP0161604A3 (es)
JP (1) JPS60255769A (es)
KR (1) KR850008162A (es)
AU (1) AU577855B2 (es)
CA (1) CA1241326A (es)
DE (1) DE3418270A1 (es)
DK (1) DK213085A (es)
ES (3) ES8605488A1 (es)
FI (1) FI79841C (es)
GR (1) GR851175B (es)
IL (1) IL75197A (es)
NO (1) NO164165C (es)
NZ (1) NZ212104A (es)
PH (1) PH22939A (es)
PT (1) PT80476B (es)
ZA (1) ZA853729B (es)

Families Citing this family (34)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3717561A1 (de) * 1987-05-25 1988-12-08 Thomae Gmbh Dr K Indol-, isochinolin- und benzazepinderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung
DE3631013A1 (de) * 1986-09-12 1988-03-24 Thomae Gmbh Dr K Neue naphthylderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung
US5153225A (en) * 1986-12-10 1992-10-06 Bayer Aktiengesellschaft Substituted basic 2-aminotetralin in pharmaceuticals
DE3718317A1 (de) * 1986-12-10 1988-06-16 Bayer Ag Substituierte basische 2-aminotetraline
FR2681862B1 (fr) * 1991-09-27 1993-11-12 Adir Cie Nouvelles (benzocycloalkyl)alkylamines, leur procede de preparation, et les compositions pharmaceutiques qui les contiennent.
FR2715658B1 (fr) * 1994-02-03 1996-03-22 Synthelabo Dérivés de N-(3-aminopropyl)-N-phényl-5,6,7,8-tétrahydronaphtalène-2-carboxamide, leur préparation et leur application en thérapeutique.
TW281667B (es) * 1994-02-03 1996-07-21 Synthelabo
NZ522410A (en) 2000-05-25 2004-09-24 F Substituted 1-aminoalkyl-lactams and their use as muscarinic receptor antagonists
SI2332921T1 (sl) 2003-06-17 2016-06-30 Arena Pharmaceuticals, Inc. 8-kloro-1-metil-2,3,4,5-tetrahidro-1H-3-benzazapin hidroklorid
CN1805939B (zh) 2003-06-17 2010-10-13 艾尼纳制药公司 用于治疗5ht2c受体相关病症的苯并氮杂卓衍生物
FR2868777B1 (fr) * 2004-04-13 2006-05-26 Servier Lab Nouveau procede de synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable
FR2868775B1 (fr) * 2004-04-13 2008-04-11 Servier Lab Nouveau procede de synthese de derives de la 1,3,4,5- tetrahydro-2h-3-benzazepin-2-one, et application a la synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable
FR2868776B1 (fr) * 2004-04-13 2008-04-18 Servier Lab Nouveau procede de synthese de derives de la 1,3-dihydro- 2h-3-benzazepin-2-one, et application a la synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable
EP2322162A1 (en) 2004-12-23 2011-05-18 Arena Pharmaceuticals, Inc. 5HT2C receptor modulator compositions and methods of use
FR2882556B1 (fr) * 2005-02-28 2007-05-04 Servier Lab Forme cristalline gamma d du chlorhydrate de l'ivabradine, son procede de preparation, et les compositions pharmaceutiques qui la contiennent
FR2882554B1 (fr) * 2005-02-28 2007-05-04 Servier Lab Forme critalline beta d du chlorhydrate de l'ivabradine, son procede de preparation, et les compositions pharmaceutiques qui la contiennent
FR2891826B1 (fr) * 2005-10-11 2007-12-28 Servier Lab Forme cristalline 6 du chlorhydrate de l'ivabradine, son procede de preparation et les compositions pharmaceutiques qui la contiennent
FR2891827B1 (fr) * 2005-10-11 2007-12-28 Servier Lab Forme cristalline deltad du chlorhydrate de l'ivabradine, son procede de preparation, et les compositions pharmaceutiques qui la contiennent
US20070219193A1 (en) * 2006-03-17 2007-09-20 Kalypsys, Inc Alkylamine-substituted bicyclic aryl compounds useful as modulators of ppar
JP5199997B2 (ja) 2006-04-03 2013-05-15 アリーナ ファーマシューティカルズ， インコーポレイテッド ８−クロロ−１−メチル−２，３，４，５−テトラヒドロ−１ｈ−３−ベンズアゼピンおよびこれに関連する中間体を調製するためのプロセス
EP2099743B1 (en) 2006-12-05 2014-08-27 Arena Pharmaceuticals, Inc. Processes for preparing (r)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1h-3-benzazepine and intermediates thereof
FR2920773B1 (fr) * 2007-09-11 2009-10-23 Servier Lab Derives de 1,2,4,5-tetrahydro-3h-benzazepines, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
US8822727B2 (en) 2008-03-04 2014-09-02 Arena Pharmaceuticals, Inc. Processes for the preparation of intermediates related to the 5-HT2C agonist (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine
FR2932800B1 (fr) * 2008-06-20 2015-02-20 Servier Lab Nouveau procede de synthese de la 7,8-dimethoxy-1,3-dihydro- 2h-3-benzazepin-2-one, et application a la synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable
US8952197B2 (en) 2009-06-18 2015-02-10 Arena Pharmaceuticals, Inc. Processes for the preparation of 5-HT2C receptor agonists
KR20130112848A (ko) 2010-06-02 2013-10-14 아레나 파마슈티칼스, 인크. 5-ｈｔ2ｃ 수용체 아고니스트의 제조 방법
EP2611449A1 (en) 2010-09-01 2013-07-10 Arena Pharmaceuticals, Inc. Administration of lorcaserin to individuals with renal impairment
SG188364A1 (en) 2010-09-01 2013-04-30 Arena Pharm Inc Salts of lorcaserin with optically active acids
EP3485878A1 (en) 2010-09-01 2019-05-22 Arena Pharmaceuticals, Inc. Modified-release dosage forms of 5-ht2c agonists useful for weight management
CA2808904A1 (en) 2010-09-01 2012-03-08 Arena Pharmaceuticals, Inc. Non-hygroscopic salts of 5-ht2c agonists
CN102424670A (zh) * 2011-10-31 2012-04-25 江苏阿尔法药业有限公司 一种合成3-(3-氯丙基)-1,3,4,5-四氢-7,8-二甲氧基-2h-3-苯并氮杂卓-2-酮的方法
RU2674670C1 (ru) 2012-10-09 2018-12-12 Арена Фармасьютикалз, Инк. Способ коррекции массы тела
FR3003859B1 (fr) * 2013-03-26 2015-03-13 Servier Lab "procede de synthese de derives de la 7,8-dimethoxy-1,3-dihydro-2h-3-benzazepin-2-one et application a la synthese de l'ivabradine"
HU230826B1 (hu) 2014-11-19 2018-07-30 Richter Gedeon Nyrt. Eljárás benzazepin származékok előállítására

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3981872A (en) * 1972-10-06 1976-09-21 A. Christiaens Societe Anonyme Derivatives of 2-amino-(1,2,3,4-tetrahydronaphthalene)
DE3119874A1 (de) * 1981-05-19 1982-12-09 Dr. Karl Thomae Gmbh, 7950 Biberach "benzazepinderivate, ihre herstellung und ihre verwendung als arzneimittel"
US4490369A (en) * 1981-05-19 1984-12-25 Dr. Karl Thomae Gesellschaft Mit Beschrankter Haftung Benzazepine derivatives, their pharmaceutical compositions and method of use
DE3418271A1 (de) * 1984-05-17 1985-11-21 Dr. Karl Thomae Gmbh, 7950 Biberach Neue benzazepinderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung

Also Published As

Publication number Publication date
ES8607245A1 (es) 1986-05-16
ES548922A0 (es) 1986-12-01
DE3418270A1 (de) 1985-11-21
KR850008162A (ko) 1985-12-13
AU4263685A (en) 1985-11-21
IL75197A0 (en) 1985-09-29
ES8701731A1 (es) 1986-12-01
DK213085D0 (da) 1985-05-14
GR851175B (es) 1985-11-25
ES543186A0 (es) 1986-03-16
FI851923L (fi) 1985-11-18
NO851949L (no) 1985-11-18
NZ212104A (en) 1989-01-06
JPS60255769A (ja) 1985-12-17
FI851923A0 (fi) 1985-05-15
EP0161604A3 (de) 1986-10-08
IL75197A (en) 1989-02-28
CA1241326A (en) 1988-08-30
EP0161604A2 (de) 1985-11-21
PT80476A (de) 1985-06-01
US4584293A (en) 1986-04-22
NO164165C (no) 1990-09-05
PH22939A (en) 1989-02-03
FI79841B (fi) 1989-11-30
FI79841C (fi) 1990-03-12
ZA853729B (en) 1987-01-28
NO164165B (no) 1990-05-28
ES548921A0 (es) 1986-05-16
DK213085A (da) 1985-11-18
PT80476B (de) 1987-04-13
AU577855B2 (en) 1988-10-06

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