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IE862297L - Sulfamic acid derivatives. - Google Patents

Sulfamic acid derivatives.

Info

Publication number
IE862297L
IE862297L IE862297A IE229786A IE862297L IE 862297 L IE862297 L IE 862297L IE 862297 A IE862297 A IE 862297A IE 229786 A IE229786 A IE 229786A IE 862297 L IE862297 L IE 862297L
Authority
IE
Ireland
Prior art keywords
hydrogen
acid derivatives
sulfamic acid
group
provides
Prior art date
Application number
IE862297A
Other versions
IE51393B1 (en
Original Assignee
Squibb & Sons Inc
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 Squibb & Sons Inc filed Critical Squibb & Sons Inc
Publication of IE862297L publication Critical patent/IE862297L/en
Publication of IE51393B1 publication Critical patent/IE51393B1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/397—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having four-membered rings, e.g. azetidine
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/425—Thiazoles
    • A61K31/427—Thiazoles not condensed and containing further heterocyclic rings
    • 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
    • C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
    • C07D205/085—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a nitrogen atom directly attached in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
    • C07F9/65583—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
    • C12P17/10—Nitrogen as only ring hetero atom
    • 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)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Zoology (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Genetics & Genomics (AREA)
  • Microbiology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Oncology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • Biotechnology (AREA)
  • Communicable Diseases (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Cephalosporin Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pyridine Compounds (AREA)

Abstract

This invention concerns intermediates for use in preparing beta -lactam antibiotics. More specifically the invention provides a compound of the formula <IMAGE> wherein R1 is hydrogen or acyl or the group R1-NH- is protected amino; R3 and R4 are the same or different and each is hydrogen, alkyl, cycloalkyl, phenyl or substituted phenyl, or one of R3 and R4 is hydrogen and the other is alkoxycarbonyl, alken-1-yl, alkyn-1-yl, 2-phenylethenyl or 2-phenylethynyl; V is a leaving group; and M<+> is hydrogen or a cation. It also provides similar compounds where R1 is a protecting group. [GB2139618A]
IE2297/86A 1980-02-07 1981-02-06 Sulfamic acid derivatives IE51393B1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US11927680A 1980-02-07 1980-02-07
US18889380A 1980-09-29 1980-09-29
IE230/81A IE51392B1 (en) 1980-02-07 1981-02-06 Beta-lactam antibiotics

Publications (2)

Publication Number Publication Date
IE862297L true IE862297L (en) 1981-08-07
IE51393B1 IE51393B1 (en) 1986-12-24

Family

ID=26817179

Family Applications (2)

Application Number Title Priority Date Filing Date
IE2297/86A IE51393B1 (en) 1980-02-07 1981-02-06 Sulfamic acid derivatives
IE230/81A IE51392B1 (en) 1980-02-07 1981-02-06 Beta-lactam antibiotics

Family Applications After (1)

Application Number Title Priority Date Filing Date
IE230/81A IE51392B1 (en) 1980-02-07 1981-02-06 Beta-lactam antibiotics

Country Status (29)

Country Link
JP (3) JPS56125362A (en)
KR (1) KR860001289B1 (en)
AR (1) AR245932A1 (en)
AU (1) AU569407B2 (en)
CA (1) CA1338670C (en)
CH (2) CH651020A5 (en)
DD (1) DD156180A5 (en)
DE (1) DE3104145C2 (en)
DK (1) DK166280C (en)
ES (1) ES499171A0 (en)
FI (1) FI80271C (en)
FR (1) FR2509299B1 (en)
GB (2) GB2071650B (en)
GR (1) GR74151B (en)
HK (1) HK57785A (en)
IE (2) IE51393B1 (en)
IL (1) IL62082A (en)
IT (1) IT1135360B (en)
KE (1) KE3539A (en)
LU (1) LU83117A1 (en)
MY (1) MY8600179A (en)
NL (1) NL192924C (en)
NO (2) NO161065C (en)
NZ (2) NZ196202A (en)
PH (3) PH24729A (en)
PT (1) PT72465B (en)
SE (3) SE457954B (en)
SG (1) SG39185G (en)
YU (1) YU44829B (en)

Families Citing this family (51)

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Publication number Priority date Publication date Assignee Title
EP0050965A1 (en) * 1980-10-23 1982-05-05 Takeda Chemical Industries, Ltd. Beta-lactamase inhibitory composition
WO1982001873A1 (en) * 1980-12-05 1982-06-10 Takeda Chemical Industries Ltd 1-sulfo-2-oxoazetidine derivatives and process for their preparation
WO1983000690A1 (en) * 1981-08-25 1983-03-03 Takeda Chemical Industries Ltd Azetidine derivatives and process for their preparation
JPS57131758A (en) * 1980-12-05 1982-08-14 Takeda Chem Ind Ltd 1-sulfo-2-oxoazetidine derivative, its preparation and use
US4673739A (en) * 1980-12-05 1987-06-16 Takeda Chemical Industries, Ltd. 4-carbamoyloxymethyl-1-sulfo-2-oxoazetidine derivatives and their production
MX7096E (en) * 1980-12-05 1987-06-19 Takeda Chemical Industries Ltd METHOD FOR PREPARATION OF 2-OXOAZETIDINE DERIVATIVES
US4675397A (en) * 1980-12-05 1987-06-23 Takeda Chemical Industries, Ltd. 1-sulfo-2-oxoazetidine derivatives and their production
US4782147A (en) * 1980-12-05 1988-11-01 Takeda Chemical Industries, Ltd. 1-sulfo-2-oxoazetidine derivatives and their production
JPS58210061A (en) * 1982-05-31 1983-12-07 Takeda Chem Ind Ltd 1-sulfo-2-oxoazetidine derivative, its preparation and use
US4572801A (en) * 1981-04-30 1986-02-25 Takeda Chemical Industries, Ltd. 4-Carbamoyloxymethyl-1-sulfo-2-oxoazetidine derivatives and their production
CA1181075A (en) * 1981-07-13 1985-01-15 David M. Floyd CRYSTALLINE ANHYDROUS FORM OF [3-S-[3.alpha.(Z),4 .beta.]]-3-[[(2-AMINO-4-THIAZOLYL) [(1-CARBOXY-1-METHYLETHOXY)IMINO]ACETYL] AMINO]-4-METHYL-2-OXO-1-AZETIDINESULFONIC ACID
FR2515182B1 (en) * 1981-10-23 1986-05-09 Roussel Uclaf NOVEL PRODUCTS DERIVED FROM 3-AMINO 2-OXO AZETIDINE 1-SULFAMIC ACID, THEIR PREPARATION PROCESS, THEIR APPLICATION AS MEDICAMENTS AND THE INTERMEDIATE PRODUCTS NECESSARY FOR THEIR PREPARATION
FR2538389B2 (en) * 1981-10-23 1986-05-16 Roussel Uclaf NEW PRODUCTS DERIVED FROM 3-AMINO 2-OXO AZETIDINE-1-SULFAMIC ACID, NEW PROCESS FOR THE PREPARATION OF OPTICALLY ACTIVE PRODUCTS, APPLICATION OF NEW PRODUCTS AS MEDICAMENTS AND PRODUCTS NECESSARY FOR THEIR PREPARATION
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AU564150B2 (en) * 1982-04-30 1987-08-06 Takeda Chemical Industries Ltd. 1-sulfo-2-azetidinone derivatives
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EP0096297B1 (en) * 1982-06-03 1988-06-15 F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft Process for the preparation of 1-sulfo-2-oxoazetidine derivatives
US4704457A (en) * 1982-06-21 1987-11-03 E. R. Squibb & Sons, Inc. Process for the preparation of (3S)-3-[[[2-(protected amino)-4-thiazolyl]-oxoacetyl]amino]-2-oxo-1-azetidinesulfonic acid and 4-substituted derivatives thereof
US4939253A (en) * 1982-08-04 1990-07-03 E. R. Squibb & Sons, Inc. 2-oxoazetidin-1-yloxy acetic acids and analogs
US4681937A (en) * 1982-09-27 1987-07-21 E. R. Squibb & Sons, Inc. 3-acylamino-2-oxo-1-azetidinyl esters of phosphonic acids, phosphoric acid and phosphoric acid esters
US4551276A (en) * 1982-10-06 1985-11-05 E. R. Squibb & Sons, Inc. 2-Oxoazetidin-1-yloxymethyl sulfonic acid and analogs
US4533495A (en) * 1982-12-30 1985-08-06 Takeda Chemical Industries, Ltd. Method of producing 2-azetidinone-1-sulfonic acid compounds
US4548747A (en) * 1983-05-02 1985-10-22 E. R. Squibb & Sons, Inc. 3-Acylamino-1-sulfonylaminocarbonylmethoxy-2-azetidinones
US4670554A (en) * 1983-05-31 1987-06-02 E. R. Squibb & Sons, Inc. ((3-Acylamino-2-oxo-1-azetidinyl)oxy)methyl)phosphinic acids
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US4501697A (en) * 1983-06-17 1985-02-26 E. R. Squibb & Sons, Inc. 4-[[(Amidomethyl)oxy]methyl]-2-oxo-1-azetidinesulfonic acid salts
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US4918185A (en) * 1984-05-22 1990-04-17 Eli Lilly And Company Process for carbon-carbon bond formation at the C-4 position of 3-acylaminoazetidinones and products and starting materials therefor
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US4680409A (en) * 1984-10-09 1987-07-14 E. R. Squibb & Sons, Inc. Hydrazide containing derivatives of 2-amino-4-thiazole-acetic acid
US4647660A (en) * 1985-05-02 1987-03-03 E. R. Squibb & Sons, Inc. 3-acylamino-2-oxo-1-azetidinesulfonic acids
US4632985A (en) * 1985-06-03 1986-12-30 E. R. Squibb & Sons, Inc. 3-acylamino-2-oxo-1-azetidinesulfonic acids
US4754041A (en) * 1985-06-17 1988-06-28 E. R. Squibb & Sons, Inc. 3-acylamino-2-oxo-1-azetidinesulfonic acids
US4638062A (en) * 1985-06-17 1987-01-20 E. R. Squibb & Sons, Inc. 3-acylamino-2-oxo-1-azetidinesulfonic acids
FR2588867B1 (en) * 1985-10-23 1988-12-09 Roussel Uclaf NOVEL PRODUCTS DERIVED FROM THE 3-AMINO 2-OXO AZETIDINE SERIES, THEIR PREPARATION PROCESS AND THEIR APPLICATION
ES2321336T3 (en) * 2005-05-09 2009-06-04 Sicor Inc. PROCEDURE FOR THE MANUFACTURE OF AZTREONAM.
JP5648250B2 (en) * 2007-11-21 2015-01-07 国立大学法人東京工業大学 Polymer organic compounds and organic compounds having sulfonated nitrogen-containing heterocycles, methods for producing them, ion exchangers, electrolyte membranes, pharmaceuticals, catalysts, membrane electrode assemblies, fuel cells using them
EP2804589A1 (en) 2012-01-16 2014-11-26 Mahmut Bilgic Pharmaceutical formulations comprising aztreonam
PL3122745T3 (en) 2014-03-24 2019-08-30 Novartis Ag Monobactam organic compounds for the treatment of bacterial infections
JP6837480B2 (en) 2015-09-23 2021-03-03 ノバルティス アーゲー Monobactam antibiotic salt and solid form
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Also Published As

Publication number Publication date
MY8600179A (en) 1986-12-31
JPH0670006B2 (en) 1994-09-07
NO170015B (en) 1992-05-25
PT72465B (en) 1982-02-04
DD156180A5 (en) 1982-08-04
GR74151B (en) 1984-06-06
PT72465A (en) 1981-03-01
ES8205397A1 (en) 1982-06-01
GB2071650A (en) 1981-09-23
GB2139618B (en) 1985-05-01
NO170015C (en) 1992-09-02
IT8119587A0 (en) 1981-02-06
AU569407B2 (en) 1988-01-28
NO860225L (en) 1981-08-10
JPH0623188B2 (en) 1994-03-30
GB2139618A (en) 1984-11-14
YU31981A (en) 1984-02-29
NZ196202A (en) 1984-07-31
DE3104145C2 (en) 1999-05-12
NL8100571A (en) 1981-09-01
SE8602194D0 (en) 1986-05-14
KE3539A (en) 1985-07-12
CH653993A5 (en) 1986-01-31
JPH0586023A (en) 1993-04-06
FI80271B (en) 1990-01-31
DE3104145A1 (en) 1981-12-17
GB8333191D0 (en) 1984-01-18
FI80271C (en) 1990-05-10
DK166280C (en) 1993-08-30
KR830005131A (en) 1983-08-03
SE8602194L (en) 1986-05-14
SG39185G (en) 1985-12-13
PH24729A (en) 1990-10-01
NZ205240A (en) 1984-07-31
SE8602193D0 (en) 1986-05-14
DK166280B (en) 1993-03-29
CH651020A5 (en) 1985-08-30
JPH02160764A (en) 1990-06-20
NO161065B (en) 1989-03-20
PH23316A (en) 1989-07-14
NL192924B (en) 1998-01-05
IT1135360B (en) 1986-08-20
AU6698581A (en) 1981-08-13
CA1338670C (en) 1996-10-22
GB2071650B (en) 1984-12-05
NO810410L (en) 1981-08-10
IE51392B1 (en) 1986-12-24
IL62082A (en) 1986-08-31
IE51393B1 (en) 1986-12-24
AR245932A1 (en) 1994-03-30
AU548896B2 (en) 1986-01-09
HK57785A (en) 1985-08-09
SE457954B (en) 1989-02-13
PH23317A (en) 1989-07-14
LU83117A1 (en) 1982-09-10
FI810352L (en) 1981-08-08
DK52381A (en) 1981-08-08
NL192924C (en) 1998-05-07
IL62082A0 (en) 1981-03-31
JPS56125362A (en) 1981-10-01
SE8100861L (en) 1981-08-08
YU44829B (en) 1991-04-30
SE500216C2 (en) 1994-05-09
FR2509299B1 (en) 1985-08-30
NO161065C (en) 1989-06-28
ES499171A0 (en) 1982-06-01
FR2509299A1 (en) 1983-01-14
AU4574885A (en) 1985-11-07
SE8602193L (en) 1986-05-14
IE810230L (en) 1981-08-07
KR860001289B1 (en) 1986-09-10

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