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ES2019949B3 - Propanaminas 3-ariloxi-3-sustituidas. - Google Patents

Propanaminas 3-ariloxi-3-sustituidas.

Info

Publication number
ES2019949B3
ES2019949B3 ES87311181T ES87311181T ES2019949B3 ES 2019949 B3 ES2019949 B3 ES 2019949B3 ES 87311181 T ES87311181 T ES 87311181T ES 87311181 T ES87311181 T ES 87311181T ES 2019949 B3 ES2019949 B3 ES 2019949B3
Authority
ES
Spain
Prior art keywords
propanamins
aryloxi
substituted
substituted propanamins
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 - Lifetime
Application number
ES87311181T
Other languages
English (en)
Inventor
David Wayne Robertson
David Taiwai Wong
Joseph Herman Krushinski
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.)
Eli Lilly and Co
Original Assignee
Eli Lilly and Co
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 Eli Lilly and Co filed Critical Eli Lilly and Co
Application granted granted Critical
Publication of ES2019949B3 publication Critical patent/ES2019949B3/es
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D277/00Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/22Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole 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
    • C07D277/28Radicals substituted by nitrogen atoms
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/02Drugs for disorders of the nervous system for peripheral neuropathies
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/24Antidepressants
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/26Psychostimulants, e.g. nicotine, cocaine
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/36Radicals substituted by singly-bound nitrogen atoms
    • C07D213/38Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D307/00Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34Heterocyclic 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
    • C07D307/38Heterocyclic 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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/52Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D333/00Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/20Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D333/00Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
    • C07D333/28Halogen atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Engineering & Computer Science (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Psychiatry (AREA)
  • Pain & Pain Management (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Furan Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Plural Heterocyclic Compounds (AREA)
ES87311181T 1986-12-22 1987-12-18 Propanaminas 3-ariloxi-3-sustituidas. Expired - Lifetime ES2019949B3 (es)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US94512286A 1986-12-22 1986-12-22

Publications (1)

Publication Number Publication Date
ES2019949B3 true ES2019949B3 (es) 1991-07-16

Family

ID=25482649

Family Applications (1)

Application Number Title Priority Date Filing Date
ES87311181T Expired - Lifetime ES2019949B3 (es) 1986-12-22 1987-12-18 Propanaminas 3-ariloxi-3-sustituidas.

Country Status (27)

Country Link
EP (1) EP0273658B1 (es)
JP (1) JP2549681B2 (es)
KR (2) KR880007433A (es)
CN (1) CN1019113B (es)
AR (1) AR243868A1 (es)
AT (1) ATE57924T1 (es)
AU (1) AU591007B2 (es)
CA (1) CA1302421C (es)
CY (2) CY1682A (es)
DE (3) DE3765919D1 (es)
DK (1) DK174599B1 (es)
EG (1) EG18230A (es)
ES (1) ES2019949B3 (es)
GR (1) GR3001207T3 (es)
HK (1) HK69693A (es)
HU (1) HU206309B (es)
IE (1) IE873449L (es)
IL (1) IL84863A (es)
LU (1) LU91131I2 (es)
MX (1) MX9845A (es)
NL (1) NL300171I2 (es)
NZ (1) NZ222980A (es)
PH (1) PH26556A (es)
PT (1) PT86389B (es)
SG (1) SG114992G (es)
SU (1) SU1598865A3 (es)
ZA (1) ZA879472B (es)

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US5362886A (en) * 1993-10-12 1994-11-08 Eli Lilly And Company Asymmetric synthesis
TW344661B (en) * 1993-11-24 1998-11-11 Lilly Co Eli Pharmaceutical composition for treatment of incontinence
GB0004152D0 (en) 2000-02-23 2000-04-12 Astrazeneca Uk Ltd Novel compounds
GB0004153D0 (en) * 2000-02-23 2000-04-12 Astrazeneca Uk Ltd Novel use
GB0004149D0 (en) 2000-02-23 2000-04-12 Astrazeneca Uk Ltd Novel compounds
GB0004151D0 (en) * 2000-02-23 2000-04-12 Astrazeneca Uk Ltd Novel use
EP1411912A1 (en) * 2001-07-31 2004-04-28 PHARMACIA & UPJOHN COMPANY Treatment of chronic pain with 3-aryloxy-3-phenylpropanamines
SE0102640D0 (sv) 2001-07-31 2001-07-31 Astrazeneca Ab Novel compounds
JP4625637B2 (ja) 2002-02-22 2011-02-02 シャイア エルエルシー 活性物質送達系及び活性物質を保護し投与する方法
US7659409B2 (en) 2002-03-19 2010-02-09 Mitsubishi Chemical Corporation 3-Hydroxy-3-(2-thienyl) propionamides and production method thereof, and production method of 3-amino-1-(2-thienyl)-1-propanols using the same
AU2003221028A1 (en) * 2002-03-19 2003-09-29 Mitsubishi Chemical Corporation 3-hydroxy-3-(2-thienyl)propionamide compound, process for producing the same, and process for producing 3-amino-1-(2-thienyl)-1-propanol compound therefrom
US20060167278A1 (en) * 2002-05-20 2006-07-27 Mitsubishi Rayon Co. Ltd. Propanolamine derivatives, process for preparation of 3-n-methylamino-1-(2-thienyl)-1-propanols and process for preparation of propanolamine derivatives
DE10235206A1 (de) 2002-08-01 2004-02-19 Basf Ag Verfahren zur Herstellung von (S)-3-Methylmino-1-(thien-2-yl)propan-1-ol
GB0220581D0 (en) 2002-09-04 2002-10-09 Novartis Ag Organic Compound
GB0229583D0 (en) * 2002-12-19 2003-01-22 Cipla Ltd A process for preparing duloxetine and intermediates for use therein
DE10302595A1 (de) 2003-01-22 2004-07-29 Basf Ag 3-Methylamino-1-(2-thienyl)-1-proganon, seine Herstellung und Verwendung
DE10345772A1 (de) 2003-10-01 2005-04-21 Basf Ag Verfahren zur Herstellung von 3-Methylamino-1-(thien-2-yl)-propan-1-ol
DE102004004719A1 (de) 2004-01-29 2005-08-18 Basf Ag Verfahren zur Herstellung von enantiomerenreinen Aminoalkoholen
NZ549381A (en) * 2004-02-19 2010-05-28 Lonza Ag Process for the preparation of enantiomerically pure 1-substituted-3-aminoalcohols
KR100796913B1 (ko) * 2004-02-20 2008-01-22 파마시아 앤드 업존 캄파니 엘엘씨 아릴 에테르의 제조 방법
DE102004022686A1 (de) 2004-05-05 2005-11-24 Basf Ag Verfahren zur Herstellung optisch aktiver Alkohole
GB0410470D0 (en) * 2004-05-11 2004-06-16 Cipla Ltd Pharmaceutical compound and polymorphs thereof
AR049401A1 (es) 2004-06-18 2006-07-26 Novartis Ag Aza-biciclononanos
GB0415746D0 (en) 2004-07-14 2004-08-18 Novartis Ag Organic compounds
EP1784381A1 (en) * 2004-08-26 2007-05-16 Neurosearch A/S Novel substituted aryloxy alkylamines and their use as monoamine neurotransmitter re-uptake inhibitors
US20060194869A1 (en) * 2004-12-23 2006-08-31 Santiago Ini Process for preparing pharmaceutically acceptable salts of duloxetine and intermediates thereof
CA2599478A1 (en) 2005-03-14 2006-09-21 Teva Pharmaceutical Industries Ltd. Process for the purification of duloxetine hydrochloride
GB0507298D0 (en) 2005-04-11 2005-05-18 Novartis Ag Organic compounds
EA019115B1 (ru) 2005-07-15 2014-01-30 Олбани Молекьюлар Рисерч, Инк. Арил- и гетероарилзамещенные тетрагидробензазепины и их применение для блокировки обратного захвата норэпинефрина, допамина и серотонина
DE102005044736A1 (de) 2005-09-19 2007-03-22 Basf Ag Neue Dehydrogenasen, deren Derivate und ein Verfahren zur Herstellung von optisch aktiven Alkanolen
US7842717B2 (en) 2005-09-22 2010-11-30 Teva Pharmaceutical Industries Ltd. DNT-maleate and methods of preparation thereof
ITMI20051970A1 (it) * 2005-10-18 2007-04-19 Solmag S P A Processo per la preparazione di eteri misti derivanti dall'inaftolo e intermedi di forme cristalline definite di + e - duloxetina
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EP1863782A1 (en) 2005-12-05 2007-12-12 Teva Pharmaceutical Industries Ltd. 2-(n-methyl-propanamine)-3-(2-naphtol) thiophene, an imputity of duloxetine hydrochloride
GB0525672D0 (en) 2005-12-16 2006-01-25 Novartis Ag Organic compounds
GB0525673D0 (en) 2005-12-16 2006-01-25 Novartis Ag Organic compounds
DE102005062662A1 (de) 2005-12-23 2007-06-28 Basf Ag Verfahren zur Herstellung optisch aktiver Alkohole
DE102005062661A1 (de) 2005-12-23 2007-08-16 Basf Ag Verfahren zur Herstellung von optisch aktivem (1S)-3-Chlor-(-thien-2-yl)-propan-1-ol
CZ299270B6 (cs) 2006-01-04 2008-06-04 Zentiva, A. S. Zpusob výroby hydrochloridu (S)-N-methyl-3-(1-naftyloxy)-3-(2-thienyl)propylaminu
WO2007077580A2 (en) 2006-01-06 2007-07-12 Msn Laboratories Limited Improved process for pure duloxetine hydrochloride
ATE552250T1 (de) 2006-12-22 2012-04-15 Synthon Bv Verfahren zur herstellung von duloxetin und verwandten verbindungen
KR101680385B1 (ko) * 2008-04-11 2016-11-28 넥타르 테라퓨틱스 올리고머-아릴옥시-치환된 프로판아민 컨쥬게이트
EP2133072A1 (en) 2008-06-13 2009-12-16 KRKA, D.D., Novo Mesto Gastro-resistant pharmaceutical oral compositions comprising duloxetine or its pharmaceutically acceptable derivatives
CN101613347B (zh) 2008-06-23 2012-07-04 中国人民解放军军事医学科学院毒物药物研究所 胺类化合物及其医药用途
HU230480B1 (hu) * 2008-07-25 2016-07-28 Egis Gyógyszergyár Nyilvánosan Működő Részvénytársaság Eljárás N-metil-ariloxi-propánamin származékok előállítására
WO2010025287A2 (en) 2008-08-27 2010-03-04 Codexis, Inc. Ketoreductase polypeptides for the production of 3-aryl-3-hydroxypropanamine from a 3-aryl-3-ketopropanamine
HUE026181T2 (en) 2008-08-27 2016-05-30 Codexis Inc Ketoreductase polypeptide for the preparation of 3-aryl-3-hydroxypropanamine from 3-aryl-3-ketopropanamine
WO2010132487A1 (en) 2009-05-12 2010-11-18 Bristol-Myers Squibb Company CRYSTALLINE FORMS OF (S)-7-([1,2,4]TRIAZOLO[1,5-a]PYRIDIN-6-YL)-4-(3,4-DICHLOROHPHENYL)-1,2,3,4-TETRAHYDROISOQUINOLINE AND USE THEREOF
CA2760837C (en) 2009-05-12 2018-04-03 Albany Molecular Research, Inc. 7-([1,2,4]triazolo[1,5-.alpha.]pyridin-6-yl)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydroisoquinoline and use thereof
CZ304602B6 (cs) 2009-09-02 2014-07-30 Zentiva, K. S. Způsob krystalizace hydrochloridu (S)-N-methyl-3-(1-naftyloxy)-3-(2-thienyl)propylaminu (hydrochloridu duloxetinu)
EP2377525A1 (en) 2010-03-26 2011-10-19 Laboratorios del Dr. Esteve S.A. Duloxetine enteric pellets
SI2558455T1 (sl) 2010-04-13 2017-12-29 Krka, D.D., Novo Mesto Sinteza duloksetina in/ali njegovih farmacevtsko sprejemljivih soli
EP2606049A4 (en) 2010-08-17 2014-01-08 Albany Molecular Res Inc 2,5-METHANO- AND 2,5-ETHANO-TETRAHYDROBENZAZEPINE DERIVATIVES AND USES THEREOF FOR BLOCKING NOREPINEPHRINE, DOPAMINE, AND SEROTONIN REUPTAKE
EP2508519A1 (en) * 2011-04-07 2012-10-10 Bioindustria Laboratorio Italiano Medicinali S.p.A In forma abbreviata Bioindustria L.I.M. S.p.A. "Process for the preparation of duloxetine and its hydrochloride salt"
GR1007725B (el) 2011-10-17 2012-10-18 Φαρματεν Αβεε, Μεθοδος δια την παρασκευη υδροχλωρικης ντουλοξετινης υψηλης καθαροτητας
PL224543B1 (pl) 2013-08-21 2017-01-31 Pabianickie Zakłady Farm Polfa Spółka Akcyjna Dojelitowa tabletka duloksetyny
US9668975B2 (en) 2014-10-14 2017-06-06 PharmaDax Inc. Method of preparing drug agglomerate
CN105777706B (zh) 2014-12-25 2019-08-23 江苏恩华药业股份有限公司 一种3-[(苯并[d][1, 3]二氧戊环-4-基)-氧基]-3-芳基丙胺类化合物及其应用
JP2016222628A (ja) * 2015-06-03 2016-12-28 株式会社トクヤマ デュロキセチン塩酸塩の製造方法
JP6182183B2 (ja) * 2015-07-07 2017-08-16 東和薬品株式会社 デュロキセチン塩基及びデュロキセチン塩酸塩の製造方法
CN106349211B (zh) * 2016-08-26 2020-10-16 江苏恩华药业股份有限公司 2-甲基-3-芳氧基-3-杂芳基丙胺类化合物及应用
EP3339304A1 (en) * 2016-12-20 2018-06-27 Laboratorios del Dr. Esteve, S.A. Quinoline and isoquinoline derivatives for treating pain and pain related conditions
JP7272709B2 (ja) 2018-08-17 2023-05-12 シャンハイ リード ファーマテック カンパニー リミテッド 3-アリールオキシル-3-5員ヘテロアリール-プロピルアミン化合物およびその使用
JP7429998B2 (ja) * 2019-05-16 2024-02-09 シャンハイ リード ファーマテック カンパニー リミテッド 3―アリールオキシル―3―5員ヘテロアリール―プロピルアミン化合物およびその結晶形態ならびに用途

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Also Published As

Publication number Publication date
LU91131I2 (fr) 2005-03-29
GR3001207T3 (en) 1992-07-30
DE122005000002I1 (de) 2005-05-12
DE3765919D1 (de) 1990-12-06
CY1682A (en) 1993-10-10
PT86389A (en) 1988-01-01
CN87108175A (zh) 1988-07-06
EP0273658B1 (en) 1990-10-31
CY2005001I1 (el) 2009-11-04
AU8266087A (en) 1988-06-23
IE873449L (en) 1988-06-22
PT86389B (pt) 1990-11-20
NL300171I1 (nl) 2005-04-01
KR960003808B1 (ko) 1996-03-22
AU591007B2 (en) 1989-11-23
EG18230A (en) 1992-10-30
PH26556A (en) 1992-08-19
DK664887A (da) 1988-06-23
SU1598865A3 (ru) 1990-10-07
DK174599B1 (da) 2003-07-14
IL84863A0 (en) 1988-06-30
MX9845A (es) 1993-12-01
JPS63185946A (ja) 1988-08-01
KR880007433A (ko) 1988-08-27
JP2549681B2 (ja) 1996-10-30
ATE57924T1 (de) 1990-11-15
CN1019113B (zh) 1992-11-18
SG114992G (en) 1993-01-29
CY2005001I2 (el) 2009-11-04
NL300171I2 (nl) 2005-06-01
HUT47561A (en) 1989-03-28
HU206309B (en) 1992-10-28
DE122005000002I2 (de) 2006-08-24
AR243868A1 (es) 1993-09-30
CA1302421C (en) 1992-06-02
HK69693A (en) 1993-07-30
EP0273658A1 (en) 1988-07-06
IL84863A (en) 1992-03-29
ZA879472B (en) 1989-08-30
NZ222980A (en) 1989-11-28
DK664887D0 (da) 1987-12-17

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