AR247569A1 - Procedimiento para preparar derivados de gem-difosfonato sustituidos por fenol - Google Patents

Procedimiento para preparar derivados de gem-difosfonato sustituidos por fenol

Info

Publication number
AR247569A1
AR247569A1 AR89313527A AR31352789A AR247569A1 AR 247569 A1 AR247569 A1 AR 247569A1 AR 89313527 A AR89313527 A AR 89313527A AR 31352789 A AR31352789 A AR 31352789A AR 247569 A1 AR247569 A1 AR 247569A1
Authority
AR
Argentina
Prior art keywords
formula
alkyl
zero
phenol
diphosphonate
Prior art date
Application number
AR89313527A
Other languages
English (en)
Original Assignee
Symphar Sa
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 Symphar Sa filed Critical Symphar Sa
Application granted granted Critical
Publication of AR247569A1 publication Critical patent/AR247569A1/es

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Classifications

    • 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
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
    • 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
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
    • C07F9/3839—Polyphosphonic acids
    • C07F9/386—Polyphosphonic acids containing hydroxy substituents in the hydrocarbon radicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/06—Antihyperlipidemics
    • 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
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
    • C07F9/3839—Polyphosphonic acids
    • C07F9/3865—Polyphosphonic acids containing sulfur substituents
    • 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
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/40—Esters thereof
    • C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4025—Esters of poly(thio)phosphonic acids
    • C07F9/404—Esters of poly(thio)phosphonic acids containing hydroxy substituents in the hydrocarbon radicals
    • 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
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/40—Esters thereof
    • C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4025—Esters of poly(thio)phosphonic acids
    • C07F9/4043—Esters of poly(thio)phosphonic acids containing sulfur substituents
    • 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
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/44—Amides thereof
    • C07F9/4403—Amides thereof the acid moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4423—Amides of poly (thio)phosphonic acids
    • 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
    • C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
    • C07F9/65515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a five-membered ring
    • C07F9/65517—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a five-membered ring condensed with carbocyclic rings or carbocyclic ring systems
    • 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
    • C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
    • C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
    • C07F9/657163—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom
    • C07F9/657181—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom the ring phosphorus atom and, at least, one ring oxygen atom being part of a (thio)phosphonic acid derivative

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)
  • Obesity (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Hematology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Diabetes (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

PROCEDIMIENTO PARA PREPARAR DERIVADOS DE GEMDIFOSFONATO SUSTITUIDOS POR FENOL DE FORMULA (I), EN DONDE: Z1, Z2, Z3 Y Z4 SON: OR EN DONDE R ES H, ALQUILO, OM EN DONDE M ES UN ION DE METAL ALCALINO O ALCALINO-TERREO O AMONIO NR4; NR2, Z1, Z2 Y Z3, Z4 PUEDEN FORMAR UN ANILLO ALQUILIDENDIOXI CON EL ATOMO DE P QUE COMPRENDE DE 2 A 8 ATOMOS DE CARBONO; X1, X2, SON H, HALOGENO, ALQUILO O ALCOXI;X3 ES H, ALQUILO R1, ACILO C(O)R1, CARBAMILO C(O)NHR1; X3O Y UNO DE LOS OTROS DOS SUSTITUYENTES X1 O X2 PUEDEN FORMAR UN ANILLO ALQUILIDENDIOXI; A ES -CH=CH-CH2, -(CH2)N-, EN DONDE N ES UN NUMERO DE 1 A 7, -(CH=CH)K - (CH2)D-CH= EN DONDE K ES CERO O 1 Y D ES UN ENTERO DE CERO A 4; B ES H, ALQUILO; T ES CERO O 1, CON LA CONDICION DE QUE T ES CERO SOLAMENTE CUANDO A ES (CH=CH)K-(CH2)D-CH= QUE CONSISTE EN HACER REACCIONAR UN ALDEHIDO DE FORMULA IV, CON UN DIFOSFONATO DE FORMULA V, EN PRESENCIA DE TETRACLORURO DE TITANIO Y UNA AMINA TERCIARIA, COMO N-METIL MORFOLINA Y PIRIDINA EN TETRAHIDRO FURANO, PA RA DAR EL ALQUENILIDENDISFOSFONATO SUSTITUIDO POR FENOL DE FORMULA (IB), HACIENDO REACCIONAR LUEGO EL COMPUESTO (IB) CON UN AGENTE REDUCTOR PARA DAR EL ALQUILIDEN-DIFOSFONATOSUSTITUIDO POR FENOL DE FORMULA (IA), EN LA CUAL A= (CH=CH)K-(CH2)D-CH2 O (CH2-CH2)K-(CH2)D-CH2; COMPRENDIENDO, CUANDO A= (CH=CH)K-(CH2)D-CH2, LA REDUCCION SELECTIVA DE LOS ENLACES DOBLES VINILIDENO-DIFOSFONATO DE LOS COMPUESTOS (IB) MEDIANTE BOROHIDRURO DE LITIO EN ETANOL O METANOL.
AR89313527A 1988-03-31 1989-03-29 Procedimiento para preparar derivados de gem-difosfonato sustituidos por fenol AR247569A1 (es)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH1239/88A CH675422A5 (es) 1988-03-31 1988-03-31

Publications (1)

Publication Number Publication Date
AR247569A1 true AR247569A1 (es) 1995-01-31

Family

ID=4205733

Family Applications (1)

Application Number Title Priority Date Filing Date
AR89313527A AR247569A1 (es) 1988-03-31 1989-03-29 Procedimiento para preparar derivados de gem-difosfonato sustituidos por fenol

Country Status (25)

Country Link
US (2) US5043330A (es)
EP (1) EP0339237B1 (es)
JP (1) JPH0822865B2 (es)
KR (1) KR0147830B1 (es)
CN (2) CN1086820A (es)
AR (1) AR247569A1 (es)
AT (1) ATE84040T1 (es)
AU (1) AU612475B2 (es)
CA (1) CA1338495C (es)
CH (1) CH675422A5 (es)
DE (2) DE68904104T2 (es)
DK (1) DK173936B1 (es)
ES (1) ES2011210T3 (es)
FI (1) FI92933C (es)
GR (2) GR900300002T1 (es)
HU (1) HU203556B (es)
IE (1) IE62692B1 (es)
IL (1) IL89649A (es)
MY (1) MY103850A (es)
NO (1) NO891317L (es)
NZ (1) NZ228516A (es)
PH (1) PH27603A (es)
PT (1) PT90175B (es)
ZA (1) ZA892126B (es)
ZW (1) ZW3789A1 (es)

Families Citing this family (38)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0377894A (ja) * 1989-08-18 1991-04-03 Toray Ind Inc メチレンジホスホン酸化合物
CA2067974A1 (en) * 1991-05-13 1992-11-14 Scott A. Biller Method for lowering cholesterol employing a phosphonomethylphosphinate squalene synthetase inhibitor
JPH05163150A (ja) * 1991-05-13 1993-06-29 E R Squibb & Sons Inc アテローム性動脈硬化症の抑制・治療剤
US5157027A (en) * 1991-05-13 1992-10-20 E. R. Squibb & Sons, Inc. Bisphosphonate squalene synthetase inhibitors and method
DE69225325T2 (de) * 1991-09-05 1998-08-27 Toray Industries Methandiphosphonsäurederivat, herstellung davon und verwendung davon als arzneimittel
JPH06172372A (ja) * 1991-11-06 1994-06-21 Takeda Chem Ind Ltd スクアレン合成酵素阻害剤およびその用途
EP0541037A3 (en) * 1991-11-06 1997-02-26 Takeda Chemical Industries Ltd Squalene synthetase inhibitory composition and use thereof
FR2683529B1 (fr) * 1991-11-12 1994-02-04 Bretagne Occidentale Universite Composes pharmaceutiques gem-diphosphonates analogues du cis-platine.
CH683996A5 (fr) * 1992-03-05 1994-06-30 Symphar Sa Dérivés aminophosphonates substitués, leur procédé de préparation et compositions pharmaceutiques les contenant.
CA2111670A1 (en) * 1992-07-10 1994-01-20 Norio Kawabe A methanediphosphonic acid derivative, process for production thereof and use for pharmaceuticals
US5332728A (en) * 1992-11-23 1994-07-26 Bristol-Myers Squibb Company Method for treating a fungal infection
US5434288A (en) * 1992-12-01 1995-07-18 Monsanto Company PLA2 inhibitors
ZA941088B (en) * 1993-02-19 1995-09-27 Symphar Sa Substituted ketophosphonates the processes for their preparation and pharmaceutical compositions containing them
KR950701338A (ko) * 1993-02-25 1995-03-23 마에다 가쓰노스케 메탄디포스폰산 화합물의 제조방법(Process for producing methanediphosphonate compound)
US5419845A (en) * 1994-03-15 1995-05-30 Basf Corporation Perfluorinated gemdiphosphonates as corrosion inhibitors for antifreeze coolants and other functional fluids
US5886206A (en) * 1994-08-24 1999-03-23 Toray Industries, Inc. Process for production of methanediphosphonic acid compound
CH690163A5 (fr) * 1995-07-28 2000-05-31 Symphar Sa Dérivés gem-diphosphonates substitués utiles en tant qu'agents anti-cancers.
GB9603637D0 (en) * 1996-02-21 1996-04-17 Smithkline Beecham Plc Process
WO1997043437A2 (en) * 1996-05-15 1997-11-20 The University Of Sheffield Isopentenyl pyrophosphate isomerase (ipi) and/or prenyl transferase inhibitors
EA200800375A1 (ru) 1997-05-14 2008-06-30 Атеродженикс, Инк. Соединения и способы ингибирования экспрессии vcam-1
US6670398B2 (en) 1997-05-14 2003-12-30 Atherogenics, Inc. Compounds and methods for treating transplant rejection
US7008645B2 (en) 1998-07-14 2006-03-07 Yissum Research Development Company Of The Hebrew University Of Jerusalem Method of inhibiting restenosis using bisphosphonates
US6984400B2 (en) 1998-07-14 2006-01-10 Yissum Research Development Company Of The Hebrew University Of Jerusalem Method of treating restenosis using bisphosphonate nanoparticles
IL125336A0 (en) * 1998-07-14 1999-03-12 Yissum Res Dev Co Compositions for inhibition and treatment of restinosis
AUPQ872800A0 (en) * 2000-07-12 2000-08-03 Heart Research Institute, The Compositions and methods for treating cardiovascular disorders
GB0019272D0 (en) * 2000-08-04 2000-09-27 Symphar Sa Pharmaceutical compounds
JP4334233B2 (ja) * 2001-04-11 2009-09-30 アセロジエニクス・インコーポレイテツド プロブコールモノエステルによって血漿ｈｄｌコレステロールレベルを上昇させ、ｈｄｌの機能性を改善するための方法
EP1435970A4 (en) * 2001-10-18 2005-05-04 Ilex Products Inc METHOD OF TREATING SKIN WITH DIPHOSPHONATE DERIVATIVES
WO2003070179A2 (en) * 2002-02-19 2003-08-28 Ilex Products, Inc. Phosphonate-phosphate and diphosphonate apolipoprotein e modulators
US20060205692A1 (en) * 2002-05-11 2006-09-14 Montes Imber F 1,1-and 1,2-Bisphosphonates as apoliprotein e modulators
US7479507B2 (en) * 2003-01-14 2009-01-20 Adam Heller Anti-inflammatory substituted phenols and elastomeric compositions for oral delivery of drugs
US10517883B2 (en) 2003-06-27 2019-12-31 Zuli Holdings Ltd. Method of treating acute myocardial infarction
KR20080111070A (ko) * 2006-03-17 2008-12-22 더 보오드 오브 트러스티스 오브 더 유니버시티 오브 일리노이즈 비스포스포네이트 화합물 및 방법
AU2008230861A1 (en) * 2007-03-26 2008-10-02 Salutria Pharmaceuticals, Llc Methods and compositions of derivatives of probucol for the treatment of diabetes
US20080280985A1 (en) * 2007-03-27 2008-11-13 Scott Robert A D Methods and Compositions Using Certain Phenolic Derivatives for the Treatment of Diabetes
US9993427B2 (en) 2013-03-14 2018-06-12 Biorest Ltd. Liposome formulation and manufacture
EP3209671B8 (en) * 2014-10-21 2019-07-31 Council of Scientific and Industrial Research Alkylidene phosphonate esters as p-glycoprotein inducers
WO2018236221A2 (en) * 2017-06-03 2018-12-27 Can Holding B.V. DISSOLUTION OF NEURODEGENERATIVE PEPTIDE DEPOSITION

Family Cites Families (7)

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Publication number Priority date Publication date Assignee Title
CA777769A (en) * 1963-03-18 1968-02-06 H. Roy Clarence Substituted methylene diphosphonic acid compounds and detergent compositions
DE1302557B (es) * 1963-04-09 1971-08-26
GB2043072B (en) * 1979-02-13 1983-11-23 Symphar Sa Diphosphonate compounds
US4416877A (en) * 1979-02-13 1983-11-22 Symphar S.A. Anti-atherosclerotic pharmaceutical compositions containing diphosphonate compounds
FR2531088B1 (fr) * 1982-07-29 1987-08-28 Sanofi Sa Produits anti-inflammatoires derives de l'acide methylenediphosphonique et leur procede de preparation
CH664158A5 (fr) * 1984-07-18 1988-02-15 Symphar Sa Derives propylidenediphosphonates-1,3 substitues en position 2, leur procede de preparation et compositions pharmaceutiques les contenant.
US6259935B1 (en) * 1997-06-24 2001-07-10 Matsushita Electrical Industrial Co., Ltd. Electro-mechanical-acoustic transducing device

Also Published As

Publication number Publication date
FI891538A (fi) 1989-10-01
NO891317L (no) 1989-10-02
NO891317D0 (no) 1989-03-29
US5128331A (en) 1992-07-07
GR3007442T3 (es) 1993-07-30
IL89649A0 (en) 1989-09-28
FI92933B (fi) 1994-10-14
IE890802L (en) 1989-09-30
PT90175B (pt) 1994-06-30
ZW3789A1 (en) 1989-08-23
EP0339237B1 (en) 1992-12-30
DK173936B1 (da) 2002-02-25
ES2011210A4 (es) 1990-01-01
DE68904104D1 (de) 1993-02-11
PT90175A (pt) 1989-11-10
NZ228516A (en) 1990-12-21
DE68904104T2 (de) 1993-06-17
KR0147830B1 (ko) 1998-08-17
CA1338495C (en) 1996-07-30
GR900300002T1 (en) 1991-06-07
CN1024555C (zh) 1994-05-18
DK148189A (da) 1989-10-17
MY103850A (en) 1993-09-30
FI92933C (fi) 1995-01-25
JPH0222285A (ja) 1990-01-25
FI891538A0 (fi) 1989-03-30
EP0339237A2 (en) 1989-11-02
KR890014569A (ko) 1989-10-24
CH675422A5 (es) 1990-09-28
IL89649A (en) 1995-07-31
CN1086820A (zh) 1994-05-18
EP0339237A3 (en) 1991-01-09
US5043330A (en) 1991-08-27
HU203556B (en) 1991-08-28
DE339237T1 (de) 1990-02-08
CN1036772A (zh) 1989-11-01
ATE84040T1 (de) 1993-01-15
JPH0822865B2 (ja) 1996-03-06
HUT50482A (en) 1990-02-28
PH27603A (en) 1993-08-31
AU612475B2 (en) 1991-07-11
ES2011210T3 (es) 1994-01-01
AU3224389A (en) 1989-10-05
DK148189D0 (da) 1989-03-28
IE62692B1 (en) 1995-02-22
ZA892126B (en) 1989-11-29

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