SE501541C2 - Fosforhaltiga HMG-CoA reduktasinhibitorer, nya mellanprodukter och metod - Google Patents

Fosforhaltiga HMG-CoA reduktasinhibitorer, nya mellanprodukter och metod

Info

Publication number
SE501541C2
SE501541C2 SE8801904A SE8801904A SE501541C2 SE 501541 C2 SE501541 C2 SE 501541C2 SE 8801904 A SE8801904 A SE 8801904A SE 8801904 A SE8801904 A SE 8801904A SE 501541 C2 SE501541 C2 SE 501541C2
Authority
SE
Sweden
Prior art keywords
hydroxybutanoic acid
mmol
phenyl
hydroxyphosphinyl
fluorophenyl
Prior art date
Application number
SE8801904A
Other languages
English (en)
Swedish (sv)
Other versions
SE8801904L (sv
SE8801904D0 (sv
Inventor
Donald Steven Karanewsky
Michael Christopher Badia
Scott Adams Biller
Eric Michael Gordon
Michael Joseph Sofia
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 SE8801904D0 publication Critical patent/SE8801904D0/xx
Publication of SE8801904L publication Critical patent/SE8801904L/xx
Publication of SE501541C2 publication Critical patent/SE501541C2/sv

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/28Phosphorus compounds with one or more P—C bonds
    • C07F9/38Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/40Esters thereof
    • C07F9/4003Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4006Esters of acyclic acids which can have further substituents on alkyl
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/547Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00Drugs for disorders of the metabolism
    • A61P3/06Antihyperlipidemics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • A61P9/10Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/28Phosphorus compounds with one or more P—C bonds
    • C07F9/30Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
    • C07F9/301Acyclic saturated acids which can have further substituents on alkyl
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/28Phosphorus compounds with one or more P—C bonds
    • C07F9/30Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
    • C07F9/302Acyclic unsaturated acids
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/28Phosphorus compounds with one or more P—C bonds
    • C07F9/30Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
    • C07F9/303Cycloaliphatic acids
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/28Phosphorus compounds with one or more P—C bonds
    • C07F9/30Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
    • C07F9/306Arylalkanephosphinic acids, e.g. Ar-(CH2)n-P(=X)(R)(XH), (X = O,S, Se; n>=1)
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/28Phosphorus compounds with one or more P—C bonds
    • C07F9/30Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
    • C07F9/32Esters thereof
    • C07F9/3205Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/3211Esters of acyclic saturated acids which can have further substituents on alkyl
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/28Phosphorus compounds with one or more P—C bonds
    • C07F9/30Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
    • C07F9/32Esters thereof
    • C07F9/3205Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/3217Esters of acyclic unsaturated acids
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/28Phosphorus compounds with one or more P—C bonds
    • C07F9/30Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
    • C07F9/32Esters thereof
    • C07F9/3205Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/3241Esters of arylalkanephosphinic acids
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/547Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/553Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
    • C07F9/572Five-membered rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/547Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/553Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
    • C07F9/572Five-membered rings
    • C07F9/5728Five-membered rings condensed with carbocyclic rings or carbocyclic ring systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/547Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/645Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
    • C07F9/6503Five-membered rings
    • C07F9/65031Five-membered rings having the nitrogen atoms in the positions 1 and 2
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/547Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/645Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
    • C07F9/6503Five-membered rings
    • C07F9/6506Five-membered rings having the nitrogen atoms in positions 1 and 3

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Public Health (AREA)
  • Urology & Nephrology (AREA)
  • Obesity (AREA)
  • Vascular Medicine (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Hematology (AREA)
  • Diabetes (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Steroid Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
SE8801904A 1987-05-22 1988-05-20 Fosforhaltiga HMG-CoA reduktasinhibitorer, nya mellanprodukter och metod SE501541C2 (sv)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US5323887A 1987-05-22 1987-05-22
US10968187A 1987-10-19 1987-10-19

Publications (3)

Publication Number Publication Date
SE8801904D0 SE8801904D0 (sv) 1988-05-20
SE8801904L SE8801904L (sv) 1988-11-23
SE501541C2 true SE501541C2 (sv) 1995-03-06

Family

ID=26731613

Family Applications (3)

Application Number Title Priority Date Filing Date
SE8801904A SE501541C2 (sv) 1987-05-22 1988-05-20 Fosforhaltiga HMG-CoA reduktasinhibitorer, nya mellanprodukter och metod
SE9201587A SE9201587D0 (sv) 1987-05-22 1992-05-14 Fosforhaltiga hmg-coa-reduktasinhibitorer, nya mellanprodukter och metod
SE9201588A SE9201588A0 (sv) 1987-05-22 1992-05-20 Fosforhaltiga HMG-CoA-reduktasinhibitorer, nya mellanprodukter och metod

Family Applications After (2)

Application Number Title Priority Date Filing Date
SE9201587A SE9201587D0 (sv) 1987-05-22 1992-05-14 Fosforhaltiga hmg-coa-reduktasinhibitorer, nya mellanprodukter och metod
SE9201588A SE9201588A0 (sv) 1987-05-22 1992-05-20 Fosforhaltiga HMG-CoA-reduktasinhibitorer, nya mellanprodukter och metod

Country Status (24)

Country Link
JP (1) JPH01139589A (nl)
KR (1) KR880013959A (nl)
CN (1) CN1030761A (nl)
AU (2) AU610174B2 (nl)
BE (1) BE1002251A3 (nl)
CH (3) CH675582A5 (nl)
DE (1) DE3817298C2 (nl)
DK (1) DK277388A (nl)
ES (1) ES2009919A6 (nl)
FI (1) FI87927C (nl)
FR (1) FR2615516B1 (nl)
GB (1) GB2205838B (nl)
GR (1) GR880100332A (nl)
HU (1) HU201085B (nl)
IE (1) IE63715B1 (nl)
IL (1) IL86463A (nl)
IT (1) IT1217684B (nl)
NL (1) NL8801331A (nl)
NO (1) NO882219L (nl)
NZ (1) NZ224734A (nl)
PH (2) PH25581A (nl)
PL (1) PL157761B1 (nl)
PT (1) PT87540B (nl)
SE (3) SE501541C2 (nl)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3817375C2 (de) * 1987-05-22 1997-04-30 Squibb & Sons Inc Phosphorhaltige HMG-CoA-Reduktase-Inhibitoren und ihre Verwendung
IE903606A1 (en) * 1989-10-10 1991-04-24 Glaxo Group Ltd Chemical compounds
US5025000A (en) * 1990-03-02 1991-06-18 E. R. Squibb & Sons, Inc. Phosphorus-containing HMG-CoA reductase inhibitor compounds
US5124453A (en) * 1990-03-02 1992-06-23 E. R. Squibb & Sons, Inc. Process for preparing certain 5,6,7,8-tetrahydroindolizinyl (ethyl or ethynyl)-hydroxy or methoxy-phosphinyl-3-hydroxy-butanoates and derivatives thereof
CA2042526A1 (en) * 1990-06-11 1991-12-12 Adeoye Y. Olukotun Method for preventing a second heart attack employing an hmg coa reductase inhibitor
CA2043525A1 (en) * 1990-06-24 1991-12-25 Donald S. Karanewsky Phosphorus-containing hmg-coa reductase inhibitors, new intermediates and method
DE4023308A1 (de) * 1990-07-21 1992-01-23 Bayer Ag Substituierte pyrido-oxazine
DE4025818A1 (de) * 1990-08-16 1992-02-20 Bayer Ag Phenylsulfonamid substituierte pyridinalken- und -aminooxyalkancarbonsaeure-derivate
NZ241574A (en) * 1991-02-22 1993-08-26 Ishihara Sangyo Kaisha Substituted phenyl derivatives of hydrazone and pesticidal compositions
US5202327A (en) * 1991-07-10 1993-04-13 E. R. Squibb & Sons, Inc. Phosphorus-containing hmg-coa reductase inhibitors
US5256692A (en) * 1992-01-07 1993-10-26 E. R. Squibb & Sons, Inc. Sulfur-containing HMG-COA reductase inhibitors
US20010006644A1 (en) 1997-07-31 2001-07-05 David J. Bova Combinations of hmg-coa reductase inhibitors and nicotinic acid and methods for treating hyperlipidemia once a day at night
WO2003076409A1 (en) * 2002-03-14 2003-09-18 Syngenta Participations Ag Derivatives of 1-phenyl-3-phenylpyrazole as herbicides
JP4407237B2 (ja) * 2002-12-24 2010-02-03 三菱化学株式会社 非水系電解液及びそれを用いる非水系電解液二次電池
JP4485169B2 (ja) 2003-05-16 2010-06-16 花王株式会社 腸管ミネラル吸収能改善剤
CN1760363B (zh) * 2004-10-14 2010-04-28 蒋继宏 杜仲3-羟基-3-甲基戊二酰辅酶a还原酶蛋白编码序列
TW200736225A (en) * 2006-01-16 2007-10-01 Sankyo Agro Co Ltd A (3-sulfur substituted phenyl) pyrazole derivative

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR339233A (fr) * 1903-12-23 1905-01-26 Cyanidgesellschaft Mit Beschra Nouveau procédé pour l'obtention d'explosifs
DE803645C (de) * 1949-10-11 1951-04-05 Dynamit Act Ges Vormals Alfred Schagwettersichere Sprengkapsel in Verbindung mit elektrischen Zuendern
DE918196C (de) * 1952-12-23 1954-09-20 J G W Berckholtz Fa Masse zur Erzeugung von farbigem Rauch
US3274035A (en) * 1964-06-15 1966-09-20 Lohr A Burkardt Metallic composition for production of hygroscopic smoke
US3862866A (en) * 1971-08-02 1975-01-28 Specialty Products Dev Corp Gas generator composition and method
DE2841815C2 (de) * 1978-09-26 1985-02-21 Buck Chemisch-Technische Werke GmbH & Co, 7347 Bad Überkingen Verfahren zur Herstellung einer Geschoßfüllung
US4438700A (en) * 1982-07-19 1984-03-27 The United States Of America As Represented By The Secretary Of The Army White smoke spotting composition for training ammunition
FR2596393B1 (fr) * 1986-04-01 1988-06-03 Sanofi Sa Derives de l'acide hydroxy-3 dihydroxyoxophosphorio-4 butanoique, leur procede de preparation, leur application comme medicament et les compositions les renfermant
DE3817375C2 (de) * 1987-05-22 1997-04-30 Squibb & Sons Inc Phosphorhaltige HMG-CoA-Reduktase-Inhibitoren und ihre Verwendung

Also Published As

Publication number Publication date
PL157761B1 (pl) 1992-06-30
NL8801331A (nl) 1988-12-16
DE3817298A1 (de) 1988-12-01
BE1002251A3 (fr) 1990-11-06
CH675582A5 (nl) 1990-10-15
IL86463A0 (en) 1988-11-15
NZ224734A (en) 1991-04-26
FR2615516B1 (fr) 1991-04-12
HUT47123A (en) 1989-01-30
GB8811931D0 (en) 1988-06-22
AU7126691A (en) 1991-05-02
SE9201588D0 (sv) 1992-05-20
SE9201587D0 (sv) 1992-05-20
PH26578A (en) 1992-08-19
SE8801904L (sv) 1988-11-23
PT87540B (pt) 1992-09-30
GB2205838A (en) 1988-12-21
AU643501B2 (en) 1993-11-18
AU1650288A (en) 1988-11-24
IT8820681A0 (it) 1988-05-20
GR880100332A (el) 1989-02-23
FR2615516A1 (fr) 1988-11-25
IL86463A (en) 1994-10-07
DK277388A (da) 1988-11-23
IE881544L (en) 1988-11-22
AU610174B2 (en) 1991-05-16
FI882385A0 (fi) 1988-05-20
SE8801904D0 (sv) 1988-05-20
FI87927B (fi) 1992-11-30
IT1217684B (it) 1990-03-30
FI882385A (fi) 1988-11-23
HU201085B (en) 1990-09-28
CN1030761A (zh) 1989-02-01
ES2009919A6 (es) 1989-10-16
JPH01139589A (ja) 1989-06-01
GB2205838B (en) 1991-12-11
PT87540A (pt) 1989-05-31
SE9201587A0 (sv) 1992-05-14
CH678625A5 (nl) 1991-10-15
SE9201588A0 (sv) 1992-05-20
FI87927C (fi) 1993-03-10
CH678626A5 (nl) 1991-10-15
DK277388D0 (da) 1988-05-20
KR880013959A (ko) 1988-12-22
NO882219L (no) 1988-11-23
IE63715B1 (en) 1995-06-14
PH25581A (en) 1991-08-08
NO882219D0 (no) 1988-05-20
DE3817298C2 (de) 1997-02-13

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