YU46147B - Postupak za dobijanje karbapenem derivata - Google Patents

Postupak za dobijanje karbapenem derivata

Info

Publication number
YU46147B
YU46147B YU42084A YU42084A YU46147B YU 46147 B YU46147 B YU 46147B YU 42084 A YU42084 A YU 42084A YU 42084 A YU42084 A YU 42084A YU 46147 B YU46147 B YU 46147B
Authority
YU
Yugoslavia
Prior art keywords
formula
defined above
hydrogen
protecting group
group
Prior art date
Application number
YU42084A
Other languages
English (en)
Other versions
YU42084A (en
Inventor
P. Dextraze
Original Assignee
Bristol-Myers Squibb 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 Bristol-Myers Squibb Co. filed Critical Bristol-Myers Squibb Co.
Priority to YU49486A priority Critical patent/YU46305B/sh
Publication of YU42084A publication Critical patent/YU42084A/xx
Publication of YU46147B publication Critical patent/YU46147B/sh

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D477/00—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring
    • 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
    • C07D213/06—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 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C07D213/16—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 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
    • C07D213/20—Quaternary compounds thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • 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
    • C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/30—Oxygen atoms
    • 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/65—One oxygen atom attached in position 3 or 5
    • 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/70—Sulfur atoms
    • 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
    • C07D213/73—Unsubstituted amino or imino radicals
    • 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
    • C07D233/66—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 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
    • C07D233/84—Sulfur 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
    • C07D295/04—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
    • C07D477/00—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring
    • C07D477/02—Preparation
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Molecular Biology (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pyridine Compounds (AREA)

Abstract

ili grupa formule: gde su R10, R11, R12 i R13 svaki nezavisno vodonik ili C1-4alkil; R2 je vodonik, anjonski naboj ili karboksi-zaštitna grupa kao što je p-nitrobenzil, pri čemu je, kada R2 predstavlja vodonik ili zaštitnu grupu, takodje prisutan i suprotan anjon kao što je Cl, Br, CH3SO3- ili CF3SO3-; i R14 je heterociklična grupa koja sadrži kvaternerizovani aazotov atom, formule: gde su R i R" nezavisno odabrani od vodonika, CH3, CH2OH, OCH3, SCH3 i NH2; i B je odabrano od O, S, S------ O, N---- CH3 ili N+------CH3 CH3 i njihovih farmacutski prihvatljivih soli, naznačen time, što intermedijer formule: u kojoj su R1 i R8 kao što je definisano gore, R2 je karboksi-zaštitna grupa kao što je p-nitrobenzil i L je odlazeća grupa kao što je difenoksifosfiniloksi, reaguje sa tiolnim jedinjenjem formule: HS------A----R14 X-- u kojoj su A i R14 kao što je definisano gore i X-- 0 je suprotan anjon kao što je definisan gore, u inertnom rastvaraču kao što je acetonitril, dimetilformamid, tetrahidrofuran, voda ili njihove smeše, u prisustvu baze kao što je ne-nukleofilni amin ili tri (C1-4)alkilamin i na temperaturi od -15В°C do sobne temperature, da bi se dobio karbapenem proizvod formule: u kojoj su R1, R8, R2, A, R14 i X-- 0 kao što je definisano gore; što se, po potrebi, vrši uklanjanje zaštitne grupe R2 da bi se dobilo jedinjenje formule (I) u kojoj R2 predstavlja vodonik ili anjonski naboj; i što se, po potrebi, proizvod formule (I) prevodi u svoju farmaceutski prihvatljivu so.
YU42084A 1983-03-08 1984-03-08 Postupak za dobijanje karbapenem derivata YU46147B (sh)

Priority Applications (1)

Application Number Priority Date Filing Date Title
YU49486A YU46305B (sh) 1983-03-08 1986-03-28 Postupak za dobijanje kvaternernih aminskih tiola

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US47137883A 1983-03-08 1983-03-08
US49969183A 1983-06-07 1983-06-07
US55729583A 1983-12-01 1983-12-01

Publications (2)

Publication Number Publication Date
YU42084A YU42084A (en) 1986-08-31
YU46147B true YU46147B (sh) 1993-05-28

Family

ID=27413179

Family Applications (2)

Application Number Title Priority Date Filing Date
YU42084A YU46147B (sh) 1983-03-08 1984-03-08 Postupak za dobijanje karbapenem derivata
YU49486A YU46305B (sh) 1983-03-08 1986-03-28 Postupak za dobijanje kvaternernih aminskih tiola

Family Applications After (1)

Application Number Title Priority Date Filing Date
YU49486A YU46305B (sh) 1983-03-08 1986-03-28 Postupak za dobijanje kvaternernih aminskih tiola

Country Status (31)

Country Link
JP (1) JPH05255250A (sh)
KR (1) KR900002247B1 (sh)
AR (1) AR241016A1 (sh)
AT (1) AT387968B (sh)
AU (2) AU572124B2 (sh)
CA (1) CA1284324C (sh)
CH (1) CH658248A5 (sh)
CY (1) CY1546A (sh)
DD (1) DD228258A5 (sh)
DE (1) DE3408347A1 (sh)
DK (1) DK140584A (sh)
ES (2) ES8505205A1 (sh)
FI (1) FI840863A (sh)
FR (1) FR2542316B1 (sh)
GB (1) GB2136802B (sh)
GR (1) GR81871B (sh)
HK (1) HK82990A (sh)
HU (1) HU193895B (sh)
IE (1) IE57098B1 (sh)
IL (1) IL71149A (sh)
IT (1) IT1178465B (sh)
LU (1) LU85241A1 (sh)
NL (1) NL8400702A (sh)
NO (1) NO166038C (sh)
NZ (1) NZ207346A (sh)
OA (1) OA07674A (sh)
PT (1) PT78211B (sh)
SE (2) SE8401278L (sh)
SG (1) SG35490G (sh)
YU (2) YU46147B (sh)
ZW (1) ZW3884A1 (sh)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4683301A (en) * 1982-04-08 1987-07-28 Bristol-Myers Company Carbapenem antibiotics
US4552696A (en) * 1982-04-09 1985-11-12 Bristol-Myers Company Carbapenem antibiotics
CA1285940C (en) * 1984-07-02 1991-07-09 Merck & Co., Inc. Carbapenems having a 2-quaternary heteroarylalkylthio substituent
IE851586L (en) * 1984-07-02 1986-01-02 Interchem Internat S A I methylcarbapenems having a 2-quaternary¹heteroarylalkylthio substituent
US4665169A (en) * 1985-09-11 1987-05-12 Bristol-Myers Company Carbapenem antibiotics
US4880922A (en) * 1985-11-22 1989-11-14 Bristol-Myers Company Carbapenems with quaternized heterothioalkylthio substitution at position 2
NZ219892A (en) * 1986-04-15 1991-02-26 Merck & Co Inc N-amino quaternised heteroarylium carbapenem derivatives and pharmaceutical compositions thereof
CA2036941A1 (en) * 1990-02-23 1991-08-24 Isao Kawamoto Carbapenem derivatives having antibiotic activity, their preparation and their use
US5712267A (en) * 1991-06-04 1998-01-27 Sankyo Company,. Limited Carbapenem derivatives, their preparation and their use as antibiotics
CA2526209A1 (en) 2003-06-12 2004-12-23 Btg International Limited Cyclic hydroxylamine as psychoactive compounds
FR2921258A1 (fr) * 2007-09-24 2009-03-27 Oreal Composition tinctoriale comprenant au moins un precurseur incolore disulfures/thiol, proced de coloration a partir de la composition

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS55147284A (en) * 1979-04-17 1980-11-17 Sanraku Inc Novel beta-lactam derivative and its preparation
IE52147B1 (en) * 1980-03-27 1987-07-08 Merck & Co Inc 4-(3-carboxy-2-oxopropyl)-azetidin-2-ones and process for their preparation
EP0038869A1 (en) * 1980-04-30 1981-11-04 Merck & Co. Inc. Process for the preparation of 1-carbapenems, and intermediates for their preparation
EP0060612A1 (en) * 1981-02-04 1982-09-22 Beecham Group Plc Process for the preparation of azabicyclo(3.2.0)-hept-2-ene derivatives
US4552873A (en) * 1981-08-19 1985-11-12 Sankyo Company Limited Carbapenem compounds, and compositions containing them
EP0074599A1 (en) * 1981-09-09 1983-03-23 Takeda Chemical Industries, Ltd. 5,6-cis-Carbapenem derivatives, their production and use
US4552696A (en) * 1982-04-09 1985-11-12 Bristol-Myers Company Carbapenem antibiotics
US4536335A (en) * 1982-06-18 1985-08-20 Bristol-Myers Company Carbapenem antibiotics

Also Published As

Publication number Publication date
IL71149A0 (en) 1984-06-29
FI840863A0 (fi) 1984-03-05
AU572124B2 (en) 1988-05-05
DE3408347A1 (de) 1984-09-13
ES530337A0 (es) 1985-05-16
IT8419945A0 (it) 1984-03-07
AR241016A2 (es) 1991-04-30
ES537349A0 (es) 1985-08-16
YU46305B (sh) 1993-05-28
NL8400702A (nl) 1984-10-01
LU85241A1 (fr) 1984-11-14
NO166038B (no) 1991-02-11
CY1546A (en) 1991-03-22
ES8505205A1 (es) 1985-05-16
IT1178465B (it) 1987-09-09
KR840008157A (ko) 1984-12-13
NO166038C (no) 1991-05-22
DK140584D0 (da) 1984-02-29
SE8901162D0 (sv) 1989-04-03
GB2136802B (en) 1987-05-20
CA1284324C (en) 1991-05-21
HUT34980A (en) 1985-05-28
SE8901162L (sv) 1989-04-03
JPH05255250A (ja) 1993-10-05
OA07674A (fr) 1985-05-23
CH658248A5 (de) 1986-10-31
PT78211B (en) 1986-08-12
DD228258A5 (de) 1985-10-09
SE8401278D0 (sv) 1984-03-07
YU49486A (en) 1987-12-31
AT387968B (de) 1989-04-10
ZW3884A1 (en) 1984-10-10
SE8401278L (sv) 1984-09-09
GR81871B (sh) 1984-12-12
IL71149A (en) 1990-03-19
ES8507145A1 (es) 1985-08-16
GB8405984D0 (en) 1984-04-11
GB2136802A (en) 1984-09-26
YU42084A (en) 1986-08-31
AR241016A1 (es) 1991-04-30
HK82990A (en) 1990-10-19
NZ207346A (en) 1987-01-23
ATA76984A (de) 1988-09-15
AU605491B2 (en) 1991-01-17
IE840549L (en) 1984-09-08
DK140584A (da) 1984-09-09
FR2542316A1 (fr) 1984-09-14
IE57098B1 (en) 1992-04-22
FI840863A (fi) 1984-09-09
HU193895B (en) 1987-12-28
FR2542316B1 (fr) 1988-10-07
AU7592487A (en) 1987-10-22
KR900002247B1 (ko) 1990-04-07
AU2536084A (en) 1984-09-13
NO840865L (no) 1984-09-10
PT78211A (en) 1984-04-01
SG35490G (en) 1990-07-13

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