AU568122B2 - Pharmaceutical bis(piperazinyl or homopiperazinyl) compounds - Google Patents

Pharmaceutical bis(piperazinyl or homopiperazinyl) compounds

Info

Publication number
AU568122B2
AU568122B2 AU25891/84A AU2589184A AU568122B2 AU 568122 B2 AU568122 B2 AU 568122B2 AU 25891/84 A AU25891/84 A AU 25891/84A AU 2589184 A AU2589184 A AU 2589184A AU 568122 B2 AU568122 B2 AU 568122B2
Authority
AU
Australia
Prior art keywords
carbon atoms
hydrogen
different
methyl
oxo
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.)
Ceased
Application number
AU25891/84A
Other versions
AU2589184A (en
Inventor
Edward Leon Barsumian
John P. Devlin
James J. Keirns
Daniel W. Mcneil
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.)
BOEHRINGER INGELHEIM Ltd
Original Assignee
BOEHRINGER INGELHEIM Ltd
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 BOEHRINGER INGELHEIM Ltd filed Critical BOEHRINGER INGELHEIM Ltd
Publication of AU2589184A publication Critical patent/AU2589184A/en
Application granted granted Critical
Publication of AU568122B2 publication Critical patent/AU568122B2/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/08—Antiallergic agents
    • 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
    • C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
    • C07D243/08—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 not condensed with other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/06—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals
    • C07D295/073—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals with the ring nitrogen atoms and the substituents separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/092—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings with aromatic radicals attached to the chain
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/10—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms
    • C07D295/104—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/108—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D295/145—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Immunology (AREA)
  • Engineering & Computer Science (AREA)
  • Pulmonology (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1. Bis-(piperazinyl- or homopiperazinyl) alkanes of the general formula I see diagramm : EP0122488,P21,F1 wherein R1 , R2 , R3 and R4 which may be identical to or different from each other, are each hydrogen, alkyl having 1 to 4 carbon atoms, hydroxyl, alkoxy having 1 to 4 carbon atoms, alkanoyloxy having up to 4 carbon atoms, halogen, trihalomethyl, di-C1-4 alkylamino, C1-4 alkoxycarbonyl, nitro, cyano or acyl having 1 to 3 carbon atoms ; R5 and R6 , which may be identical to or different from each other, are each hydrogen, methyl, hydroxyl, carboxyl, C1-4 alkoxycarbonyl, hydroxymethyl, phenyl or p-chlorophenyl, R7 and R8 are each hydrogen or methyl ; j and k are integers from 0 to 3, their sum being no more than 4 ; m and n are integers from 0 to 3, their sum being no more than 4 ; A is -CH2 - or -CH2 CH2 - ; or R5 and R7 together or R6 and R8 together are oxo, provided k or m is other than O ; or R5 and R7 together and R6 and R8 together are oxo, provided k or m are other than O ; R9 and R10 , which may be the same or different, represent hydrogen or from one to four methyl substituents on the carbon atoms of the piperazine ring (A = -CH2 -) ; R11 , R12 , R13 and R14 , which may be identical to or different from each other, are each hydrogen or methyl ; or R11 and R12 together and/or R13 and R14 together are oxo ; and X is alkylene of 1 to 2 carbon atoms, optionally hydroxy-substituted with the proviso that when A = -CH2 -, R1 to R14 are hydrogen and j, k, m and n are each zero, then X cannot be 1,2-ethylenediol, and physiologically acceptable acid addition salts thereof.
AU25891/84A 1983-03-21 1984-03-20 Pharmaceutical bis(piperazinyl or homopiperazinyl) compounds Ceased AU568122B2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US47700883A 1983-03-21 1983-03-21
US477008 1983-03-21

Publications (2)

Publication Number Publication Date
AU2589184A AU2589184A (en) 1984-09-27
AU568122B2 true AU568122B2 (en) 1987-12-17

Family

ID=23894132

Family Applications (1)

Application Number Title Priority Date Filing Date
AU25891/84A Ceased AU568122B2 (en) 1983-03-21 1984-03-20 Pharmaceutical bis(piperazinyl or homopiperazinyl) compounds

Country Status (24)

Country Link
EP (1) EP0122488B1 (en)
JP (1) JPS59176265A (en)
KR (1) KR890000487B1 (en)
AT (1) ATE43843T1 (en)
AU (1) AU568122B2 (en)
CA (1) CA1218652A (en)
CS (1) CS254971B2 (en)
DD (1) DD219642A5 (en)
DE (1) DE3478601D1 (en)
DK (1) DK166022C (en)
ES (4) ES8505992A1 (en)
FI (1) FI80269C (en)
GR (1) GR81827B (en)
HU (1) HU191599B (en)
IE (1) IE57136B1 (en)
IL (1) IL71291A (en)
NO (1) NO162907C (en)
NZ (1) NZ207554A (en)
PH (1) PH25216A (en)
PL (2) PL141127B1 (en)
PT (1) PT78278B (en)
SU (2) SU1574174A3 (en)
YU (2) YU45598B (en)
ZA (1) ZA842037B (en)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS645287Y2 (en) * 1984-11-20 1989-02-09
US4692448A (en) * 1984-11-20 1987-09-08 Boehringer Ingelheim Pharmaceuticals, Inc. Bis(arylpiperazinyl)sulfur compounds
CA2180190A1 (en) * 1995-07-10 1997-01-11 Kazumi Ogata Benzylpiperazine derivatives
DE69937045T2 (en) * 1998-02-19 2008-05-29 Kowa Co., Ltd., Nagoya CYCLIC AMID DERIVATIVES
US6897305B2 (en) * 1998-06-08 2005-05-24 Theravance, Inc. Calcium channel drugs and uses
US7101909B2 (en) 1998-10-12 2006-09-05 Theravance, Inc. Calcium channel drugs and uses
NZ515374A (en) 1999-05-18 2004-09-24 Teijin Ltd Remedies or prophylactics for diseases in association with chemokines
CA2378499A1 (en) * 1999-08-04 2001-02-15 Teijin Limited Cyclic amine ccr3 antagonists
CN1298715C (en) * 2001-03-13 2007-02-07 先灵公司 Non-imidazole compounds as histamine H3 antagonists

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU5964669A (en) * 1968-08-20 1971-02-25 LILLY INDUSTRIES LIMITED and ELI LILLY AND COMPANY Compounds having anti-schistolomiasis activity
JPS52131590A (en) * 1976-04-09 1977-11-04 Nippon Shinyaku Co Ltd Bis-trimethoxybenzylpiperazino-alkanes
AU5026885A (en) * 1984-11-20 1986-05-29 Boehringer Ingelheim Pharmaceuticals, Inc. Bis (arylpiperazinyl) Sulfur compounds

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA675224A (en) * 1963-12-03 Gabler Rudolf Piperazine derivatives

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU5964669A (en) * 1968-08-20 1971-02-25 LILLY INDUSTRIES LIMITED and ELI LILLY AND COMPANY Compounds having anti-schistolomiasis activity
JPS52131590A (en) * 1976-04-09 1977-11-04 Nippon Shinyaku Co Ltd Bis-trimethoxybenzylpiperazino-alkanes
AU5026885A (en) * 1984-11-20 1986-05-29 Boehringer Ingelheim Pharmaceuticals, Inc. Bis (arylpiperazinyl) Sulfur compounds

Also Published As

Publication number Publication date
IE840682L (en) 1984-09-21
CS254971B2 (en) 1988-02-15
ZA842037B (en) 1985-12-24
DD219642A5 (en) 1985-03-13
JPS59176265A (en) 1984-10-05
PL252632A1 (en) 1986-01-14
DK166022C (en) 1993-08-02
YU107286A (en) 1987-10-31
FI841081A0 (en) 1984-03-19
PT78278A (en) 1984-04-01
FI80269B (en) 1990-01-31
YU48284A (en) 1987-10-31
IE57136B1 (en) 1992-05-06
ES535439A0 (en) 1985-09-16
SU1574174A3 (en) 1990-06-23
ES530762A0 (en) 1985-06-16
FI80269C (en) 1990-05-10
NO162907C (en) 1990-03-07
ES8505992A1 (en) 1985-06-16
PT78278B (en) 1986-08-08
DK160184D0 (en) 1984-03-20
DK166022B (en) 1993-03-01
PL246774A1 (en) 1985-07-30
HU191599B (en) 1987-03-30
PH25216A (en) 1991-03-27
DK160184A (en) 1984-09-22
AU2589184A (en) 1984-09-27
CS196084A2 (en) 1987-07-16
EP0122488A1 (en) 1984-10-24
ATE43843T1 (en) 1989-06-15
NO162907B (en) 1989-11-27
NZ207554A (en) 1987-03-31
HUT34016A (en) 1985-01-28
CA1218652A (en) 1987-03-03
ES535438A0 (en) 1985-09-16
ES535440A0 (en) 1985-09-16
ES8600230A1 (en) 1985-09-16
SU1568887A3 (en) 1990-05-30
ES8600228A1 (en) 1985-09-16
NO841078L (en) 1984-09-24
ES8600229A1 (en) 1985-09-16
DE3478601D1 (en) 1989-07-13
GR81827B (en) 1984-12-12
KR840008007A (en) 1984-12-12
PL141127B1 (en) 1987-06-30
IL71291A0 (en) 1984-06-29
YU45598B (en) 1992-07-20
FI841081A (en) 1984-09-22
KR890000487B1 (en) 1989-03-18
EP0122488B1 (en) 1989-06-07
IL71291A (en) 1987-11-30

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