ES544184A1 - Procedimiento para la obtencion de pirazolo 3,4-d-piridin-3-onas -b-2-sustituidas,heterociclicamente condensadas - Google Patents

Procedimiento para la obtencion de pirazolo 3,4-d-piridin-3-onas -b-2-sustituidas,heterociclicamente condensadas

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Publication number
ES544184A1
ES544184A1 ES544184A ES544184A ES544184A1 ES 544184 A1 ES544184 A1 ES 544184A1 ES 544184 A ES544184 A ES 544184A ES 544184 A ES544184 A ES 544184A ES 544184 A1 ES544184 A1 ES 544184A1
Authority
ES
Spain
Prior art keywords
pyrazolo
ones
pyridin
heterocycle
condensed
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
ES544184A
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English (en)
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Novartis AG
Original Assignee
Ciba Geigy AG
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Filing date
Publication date
Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG
Publication of ES544184A1 publication Critical patent/ES544184A1/es
Expired legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic 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
    • C07D213/02—Heterocyclic 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
    • C07D213/04—Heterocyclic 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
    • C07D213/60—Heterocyclic 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 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
    • C07D213/72—Nitrogen atoms
    • C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/08—Antiepileptics; Anticonvulsants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/20—Hypnotics; Sedatives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic 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
    • C07D213/02—Heterocyclic 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
    • C07D213/04—Heterocyclic 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
    • C07D213/60—Heterocyclic 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 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
    • C07D213/72—Nitrogen atoms
    • C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic 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
    • C07D213/02—Heterocyclic 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
    • C07D213/04—Heterocyclic 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
    • C07D213/60—Heterocyclic 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 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79—Acids; Esters
    • C07D213/80—Acids; Esters in position 3
    • 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
    • C07D231/14—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 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
    • C07D231/28—Two oxygen or sulfur atoms
    • C07D231/30—Two oxygen or sulfur atoms attached in positions 3 and 5
    • C07D231/32—Oxygen atoms
    • C07D231/34—Oxygen atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
    • C07D471/14—Ortho-condensed systems
    • 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
    • C07D495/12—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 three hetero rings
    • C07D495/14—Ortho-condensed systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Anesthesiology (AREA)
  • Pain & Pain Management (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

Procedimiento para la obtención de pirazolo[3,4-d]-piridin-3-onas[b]-2-sustituidas, heterociclicamente condensadas, de fórmulas IA ó IB **fórmula** donde A significa un resto divalente de 3 miembros como complemento de un anillo heterocíclico insaturado, de 5 miembros, condensado, que contiene azúfre, oxigeno o un átomo de nitrógeno de amino insustituido ó sustituido por alquilo inferior, y donde los átomos de carbono en el resto mencionado están insustituidos o uno de ellos está sustituido por alquilo inferior, carbo-alcoxi- inferior, halógeno ó trifluormetilo; ó A representa un resto divalente, de 3 miembros, como complemento de un anillo heterociclico insaturado, de 5 miembros, condensado, que contiene 2 átomos de nitrógeno, que están separados entre si por un átomo de carbono, siendo uno un nitrógeno de amino en caso dado sustituido por alquilo inferior y el otro un nitrógeno de imino, y donde el átomo de carbono está insustituido ó sustituido por alquilo inferior, fenilo ó aquel feniloque, a su vez, está monosustituido por alquilo inferior, alcoxi inferior, halógeno ó trifluormetilo; ó A representa un resto divalente de 3 miembros como complemento de un anillo heterociclico, insaturado de 5 miembros, condensado, que contiene un átomo de nitrógeno y un átomo de oxigeno o de azúfre, y donde el átomo de carbono en el resto mencionado está insustituido ó sustituido por alquilo inferior, alcoxi inferior, halógeno o trifluormetilo; ó A representa un resto divalente de 4 miembros como complemento de un anillo heterociclico insaturado, de 6 miembros, condensado, que contiene un átomo de hidrógeno, no estando el átomo de nitrógeno enlazado directamente con el átomo Beta-carbono del sistema de anillo, y donde los átomos de carbono en el resto mencionado están insustituido ó sustituidos por 1 hasta 3 radicales del grupo alquilo inferior, alcoxi inferior, halógeno o trifluormetilo, ó A representa un resto divalente de 4 miembros como complemento de un anillo heterociclico insaturado, de 6 miembros, condensado, que contiene 2 átomos de nitrógeno, y donde los átomos de carbono en el resto mencionado están insustituidos ó sustituido por 1 ó 2 radicales del grupo alquilo inferior, alcoxi inferior, halógeno o trifluormetilo; R1 significa fenilo que, en caso dado, está sustituido por uno ó dos restos del grupo alquilo inferior, alcoxi inferior, halógeno o trifluormetilo; ó R1 significa un resto heterociclico insaturado, de 5 miembros, que contiene un heteroátomo del grupo azúfre, oxígeno y nitrógeno de amino, en caso dado sustituido por alquilo inferior, ó el resto mencionado contiene dos heteroátomos, compuesto, por una parte de un nitrógeno de imino y, por otra parte, de un nitrógeno de amino, en caso dado sustituido por alquilo inferior, azúfre u oxigeno; ó R1 representa un resto heterociclico de 6 miembros, insaturado, que contiene 1 ó átomos de nitrógeno; o R1 significa un resto heterociclico insaturado de 5 miembros, unido por benzocondensación biciclica, que tiene un heteroátomo del grupo azúfre, oxigeno y nitrógeno de amino, en caso dado sustituido por alquilo inferior; ó R1 significa un resto heterociclico insaturado de 5 miembros, unido por benzo-condensación biciclica, que contiene 2 heteroátomos que, por una parte, se componen de un nitrógeno de imino y, por otra parate, de un nitrógeno de amino, en caso dado sustituido por alquilo inferior, oxígeno o azúfre; o R1 significa un resto heterociclico insaturado, de 6 miembros, unido por benzo-condensación biciclica, que contiene 1 ó átomos de nitrógeno; ó R1significa cada uno de los restos heterociclicos mencionados que está sustituidos en los átomos de carbono por alcoxi inferior, ó halógeno; R2,R3 y R''3, independientes entre si, significan hidrógeno ó alquilo inferior; sus tautómeros y sales de éstas, caracterizado porque un compuesto de fórmula X **fórmula** donde W y R3 significan hidrógeno, y Z significa **fórmula** se condensa en presencia de un disolvente orgánico inerte y de un agente de condensación, ó donde W significa ** fórmula** y Z significa hidrógeno . Se condesnsa en presencia de una cantida catalítica de un ácido, tal como ácido clorhídrico ó don W significa ** fórmula** y Z significa R2CO- ó R3-N-Z- representa isocianato , y A, R1, R2 y R3 tienen los significados más arriba indicados, se condensa en presencia de un disolvente, y, si se desea, un grupo reactivo molesto se protege pasajeramente y se aisla del compuesto obtenido de fórmula IA ó IB; y, si se desea, un compuesto obtenido de la fórmula IA ó IB se transforma en otro compuesto de la presente invención, y/o si se desea, un compuesto obtenido se transforma en su sal ó una sal obtenida en el compuesto libre ó en otra sal.
ES544184A 1983-01-10 1985-06-14 Procedimiento para la obtencion de pirazolo 3,4-d-piridin-3-onas -b-2-sustituidas,heterociclicamente condensadas Expired ES544184A1 (es)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US06/457,105 US4479955A (en) 1983-01-10 1983-01-10 Heterocycle-fused pyrazolo[3,4-d]pyridin-3-ones as benzodiazepine receptor modulators

Publications (1)

Publication Number Publication Date
ES544184A1 true ES544184A1 (es) 1986-12-01

Family

ID=23815456

Family Applications (2)

Application Number Title Priority Date Filing Date
ES528750A Expired ES8606343A1 (es) 1983-01-10 1984-01-09 Procedimiento para la obtencion de pirazolo (3,4-d)-piridin-3-onas (b)-2-sustituidas, heterociclicamente condensadas
ES544184A Expired ES544184A1 (es) 1983-01-10 1985-06-14 Procedimiento para la obtencion de pirazolo 3,4-d-piridin-3-onas -b-2-sustituidas,heterociclicamente condensadas

Family Applications Before (1)

Application Number Title Priority Date Filing Date
ES528750A Expired ES8606343A1 (es) 1983-01-10 1984-01-09 Procedimiento para la obtencion de pirazolo (3,4-d)-piridin-3-onas (b)-2-sustituidas, heterociclicamente condensadas

Country Status (16)

Country Link
US (1) US4479955A (es)
EP (1) EP0115469B1 (es)
JP (1) JPS59130882A (es)
AT (1) ATE27276T1 (es)
AU (1) AU2317184A (es)
CA (1) CA1250579A (es)
DD (1) DD216019A5 (es)
DE (1) DE3463769D1 (es)
DK (1) DK8084A (es)
ES (2) ES8606343A1 (es)
FI (1) FI840053A (es)
GR (1) GR79458B (es)
IL (1) IL70635A0 (es)
NO (1) NO840068L (es)
PT (1) PT77926B (es)
ZA (1) ZA84154B (es)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4560689A (en) * 1983-01-10 1985-12-24 Ciba-Geigy Corporation Heterocyclic-fused pyrazolo-[3,4-d]pyridin-3-ones as benzodiazepine receptor modulators
EP0126970A3 (en) * 1983-04-27 1985-11-06 Beecham Group Plc Anxiolytic and anti-depressant thienopyridine derivatives
CA1263651A (en) * 1984-07-09 1989-12-05 Ciba-Geigy Ag Certain ring-fused pyrazolo ¬3,4-d|-pyridin-3-one derivatives
US4647566A (en) * 1984-07-09 1987-03-03 Ciba-Geigy Corporation Certain ring-fused pyrazolo[3,4-d]-pyridin-3-one derivatives in treating anxiety
US4602014A (en) * 1984-07-09 1986-07-22 Ciba-Geigy Corporation Ring-fused pyrazolo[3,4-d]-pyridin-3-one derivatives as benzodiazepine receptor modulators
JPS61112075A (ja) * 1984-11-05 1986-05-30 Shionogi & Co Ltd チエニルピラゾロキノリン誘導体
US4596799A (en) * 1985-01-29 1986-06-24 Ciba-Geigy Corporation 9H-pyrrolo[2,1-c]-1,2,4-triazolo[4,3-a][1,4]benzodiazepines
US4831013A (en) * 1986-03-20 1989-05-16 Ciba-Geigy Corporation 2-substituted-e-fused-[1,2,4]triazolo[1,5-c]pyrimidines, pharmaceutical compositions, and uses thereof
US4826854A (en) * 1986-11-25 1989-05-02 Ciba-Geigy Corporation Certain cycloalka-(b)-pyrazolo(3,4-d)-pyridin-3-one derivatives
DE3728278A1 (de) * 1986-12-17 1988-06-23 Bayer Ag Herbizide und fungizide mittel auf basis von substituierten pyrazolin-5-on derivaten
KR0169813B1 (ko) * 1995-07-12 1999-01-15 김종인 4-아미노-3-아실나프티리딘 유도체
GB9806102D0 (en) 1998-03-20 1998-05-20 Merck Sharp & Dohme Therapeutic agents
EP2166853B1 (en) * 2007-06-08 2014-05-28 Dart Neuroscience (Cayman) Ltd Therapeutic pyrazolonaphthyridine derivatives
EP2627655B1 (en) * 2010-10-14 2015-09-16 Dart Neuroscience (Cayman) Ltd FUSED 3-OXO-PYRAZOLO[4,3-c]PYRIDINE COMPOUNDS AS GABAA MODULATORS
RU2477596C2 (ru) * 2011-05-16 2013-03-20 Александр Иванович Леляк Способ стимуляции роста и защиты ягодных культур от болезней, вызываемых грибными патогенами
RU2481760C2 (ru) * 2011-05-16 2013-05-20 Александр Иванович Леляк Способ выращивания растений
TW201522337A (zh) * 2013-03-12 2015-06-16 Arqule Inc 經取代之三環吡唑並－嘧啶化合物類
PE20200608A1 (es) 2017-06-30 2020-03-10 Bayer Animal Health Gmbh Nuevos derivados de azaquinolina

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3697532A (en) * 1970-08-12 1972-10-10 Squibb & Sons Inc 5-methyldipyrazolo {8 3,4-b;3{40 ,4{40 -d{9 {0 pyridin-3(2h)-ones
US3669950A (en) * 1970-12-01 1972-06-13 Squibb & Sons Inc DIPYRAZOLO{8 3,4-b:3,4d{9 -PYRIDIN-3-ONES
US4146621A (en) * 1973-01-16 1979-03-27 The Regents Of The University Of Michigan Process of treating proliferative skin diseases
CY1357A (en) * 1979-06-21 1987-08-07 Ciba Geigy Ag Pyrazolo-quinolines, processes for their production, pharmaceutical compositions containing them and their therapeutical use
US4312870A (en) * 1979-06-21 1982-01-26 Ciba-Geigy Corporation Pyrazoloquinolines

Also Published As

Publication number Publication date
AU2317184A (en) 1984-07-12
EP0115469B1 (de) 1987-05-20
GR79458B (es) 1984-10-30
JPS59130882A (ja) 1984-07-27
IL70635A0 (en) 1984-04-30
PT77926A (en) 1984-02-01
PT77926B (en) 1986-06-02
US4479955A (en) 1984-10-30
DD216019A5 (de) 1984-11-28
NO840068L (no) 1984-07-11
ES8606343A1 (es) 1986-04-01
FI840053A0 (fi) 1984-01-06
ATE27276T1 (de) 1987-06-15
DK8084A (da) 1984-07-11
EP0115469A1 (de) 1984-08-08
CA1250579A (en) 1989-02-28
ES528750A0 (es) 1986-04-01
ZA84154B (en) 1984-08-29
DE3463769D1 (en) 1987-06-25
FI840053A (fi) 1984-07-11
DK8084D0 (da) 1984-01-09

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