CA2089440A1 - Ortho-substituted benzoylguanidines, process for their preparation, their use as a medicament or diagnostic and medicaments containing them - Google Patents

Ortho-substituted benzoylguanidines, process for their preparation, their use as a medicament or diagnostic and medicaments containing them

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Publication number
CA2089440A1
CA2089440A1 CA002089440A CA2089440A CA2089440A1 CA 2089440 A1 CA2089440 A1 CA 2089440A1 CA 002089440 A CA002089440 A CA 002089440A CA 2089440 A CA2089440 A CA 2089440A CA 2089440 A1 CA2089440 A1 CA 2089440A1
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Canada
Prior art keywords
medicament
ortho
alkyl
formula
diagnostic
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.)
Granted
Application number
CA002089440A
Other languages
French (fr)
Other versions
CA2089440C (en
Inventor
Florian Lang
Hans-Jochen Lang
Andreas Weichert
Heinrich Englert
Wolfgang Scholz
Udo Albus
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Sanofi Aventis Deutschland GmbH
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Individual
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Publication of CA2089440A1 publication Critical patent/CA2089440A1/en
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Publication of CA2089440C publication Critical patent/CA2089440C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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    • 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
    • C07D295/22—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 hetero atoms directly attached to ring nitrogen atoms
    • C07D295/26—Sulfur atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • 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
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • 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
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/06—Antiarrhythmics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/08—Vasodilators for multiple indications
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/12—Antihypertensives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C311/21—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/37—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
    • C07C311/38—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring having sulfur atoms of sulfonamide groups and amino groups bound to carbon atoms of six-membered rings of the same carbon skeleton
    • C07C311/39—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring having sulfur atoms of sulfonamide groups and amino groups bound to carbon atoms of six-membered rings of the same carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
    • 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
    • C07D295/155—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 separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Health & Medical Sciences (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Diabetes (AREA)
  • Endocrinology (AREA)
  • Obesity (AREA)
  • Emergency Medicine (AREA)
  • Urology & Nephrology (AREA)
  • Hematology (AREA)
  • Hospice & Palliative Care (AREA)
  • Vascular Medicine (AREA)
  • Reproductive Health (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)

Abstract

Ortho-substituted benzoylguanidines of the formula I
(see formula I) are described where:
R(1) is halogen, alkyl or -X-R(6), where X is O, S, NR(7) or Y-ZO and R(6) is H, (cyclo)-(halo)alkyl(methyl) or -C n H2n-phenyl, R(3) is H or -X-R(6), R(2) and R(4) are R(11)-SO1-2- or (di)-alkyl-N-SO2-, or one of the two radicals R(2) or R(4) is hydrogen or is defined as R(1), R(5) is H, methyl, F, Cl or methoxy, and their pharmaceutically tolerable salts.
They are obtained by a process in which compounds of the formula II
(see formula II) are reacted with guanidine, in which R(1) to R(5) have the given meaning and L is a leaving group which can be easily nucleophilically substituted. The compounds I are used for preparing a medicament for the treatment and for the prophylaxis of cardiac arrhythmias and of ischemically induced damage; as well as for preparing a medicament for inhibiting the proliferation of cells.
CA002089440A 1992-02-15 1993-02-12 Ortho-substituted benzoylguanidines, process for their preparation, their use as a medicament or diagnostic and medicaments containing them Expired - Fee Related CA2089440C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4204576 1992-02-15
DEP4204576.2 1992-02-15

Publications (2)

Publication Number Publication Date
CA2089440A1 true CA2089440A1 (en) 1993-08-16
CA2089440C CA2089440C (en) 2006-04-11

Family

ID=6451808

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002089440A Expired - Fee Related CA2089440C (en) 1992-02-15 1993-02-12 Ortho-substituted benzoylguanidines, process for their preparation, their use as a medicament or diagnostic and medicaments containing them

Country Status (15)

Country Link
EP (1) EP0556673B1 (en)
JP (1) JP3558224B2 (en)
AT (1) ATE158278T1 (en)
AU (1) AU658262B2 (en)
CA (1) CA2089440C (en)
DE (1) DE59307360D1 (en)
DK (1) DK0556673T3 (en)
ES (1) ES2108144T3 (en)
FI (1) FI112076B (en)
GR (1) GR3025523T3 (en)
HU (1) HU220219B (en)
IL (1) IL104714A (en)
NO (1) NO179002C (en)
NZ (1) NZ245895A (en)
ZA (1) ZA93985B (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5753680A (en) * 1994-08-31 1998-05-19 Merck Patent Gesellschaft Mit Beschrankter Haftung Heterocyclyl-benzoylguanidines
US5849796A (en) * 1994-08-28 1998-12-15 Merck Patent Gelsellschaft Mit Beschrankter Haftung Ortho-substituted benzoil acid derivatives
EP0921117A2 (en) † 1993-08-24 1999-06-09 Hoechst Aktiengesellschaft Acylguanidines
US6169107B1 (en) 1993-04-28 2001-01-02 Sumitomo Pharmaceutical Co., Ltd. Indoloylguanidine derivatives

Families Citing this family (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CZ284456B6 (en) * 1992-02-15 1998-12-16 Hoechst Aktiengesellschaft Amino substituted benzylguanidines, process of their preparation and their use for preparing medicaments
IL109570A0 (en) * 1993-05-17 1994-08-26 Fujisawa Pharmaceutical Co Guanidine derivatives, pharmaceutical compositions containing the same and processes for the preparation thereof
DE4318756A1 (en) * 1993-06-05 1994-12-08 Hoechst Ag Substituted benzoylguanidines, process for their preparation, their use as medicament or diagnostic agent, and medicament containing them
DE4328869A1 (en) * 1993-08-27 1995-03-02 Hoechst Ag Ortho-substituted benzoylguanidines, process for their preparation, their use as a medicament or diagnostic agent, and medicament containing them
DE4412334A1 (en) * 1994-04-11 1995-10-19 Hoechst Ag Substituted N-heteroaroylguanidines, process for their preparation, their use as a medicament or diagnostic agent, and medicament containing them
DE4415873A1 (en) * 1994-05-05 1995-11-09 Hoechst Ag Substituted bicyclic heteroaroylguanidines, process for their preparation, their use as medicament or diagnostic agent and medicament containing them
DE4417004A1 (en) * 1994-05-13 1995-11-16 Hoechst Ag Perfluoroalkyl-substituted benzoylguanidines, process for their preparation, their use as a medicament or diagnostic agent, and medicament containing them
DE4422685A1 (en) * 1994-06-29 1996-01-04 Hoechst Ag Ortho-amino-substituted benzoylguanidines, processes for their preparation, their use as medicaments or diagnostic agents and medicaments containing them
IL114670A0 (en) * 1994-08-05 1995-11-27 Fujisawa Pharmaceutical Co Guanidine derivatives pharmaceutical compositions containing the same and processes for the preparation thereof
DE4430213A1 (en) * 1994-08-28 1996-02-29 Merck Patent Gmbh Arylbenzoylguanidine
DE4430916A1 (en) * 1994-08-31 1996-03-07 Merck Patent Gmbh Alkyl benzoylguanidine derivatives
DE4437874A1 (en) * 1994-10-22 1996-04-25 Merck Patent Gmbh Alkyl 5-methylsulfonylbenzoylguanidine derivatives
DE4441880A1 (en) * 1994-11-24 1996-05-30 Hoechst Ag Substituted benzoylguanidines, processes for their preparation, their use as medicaments or diagnostic agents and medicaments containing them
DE19502895A1 (en) * 1995-01-31 1996-08-01 Merck Patent Gmbh 4-mercapto-benzoylguanidine derivatives
DE69603771T2 (en) * 1995-04-18 2000-09-07 Hoechst Ag Substituted indenoylguanidines with antiarrhythmic and cardioprotective effects
DE19517848A1 (en) * 1995-05-16 1996-11-21 Merck Patent Gmbh Fluorine-containing benzoylguanidines
EP0765867A1 (en) * 1995-09-27 1997-04-02 Hoechst Aktiengesellschaft Substituted benzoyl guanidines, process for their preparation, their use as antiarrhythmics or diagnostic agent as well as pharmaceuticals containing them
DE19540995A1 (en) * 1995-11-03 1997-05-07 Hoechst Ag Substituted sulfonimidamides, process for their preparation, their use as a medicament or diagnostic agent, and medicament containing them
DE19542306A1 (en) * 1995-11-14 1997-05-15 Hoechst Ag Sulfonylamino-substituted benzoylguanidines, process for their preparation, their use as a medicament or diagnostic agent, and medicament containing them
PL316439A1 (en) * 1995-11-20 1997-05-26 Hoechst Ag Novel substituted derivatives of benzoyloguanidine, method of obtaining them, their application in production of pharmaceutic and diagnostic agents and pharmaceutic agent as such
DE19546736A1 (en) * 1995-12-14 1997-06-19 Hoechst Ag Substituted chromanylsulfonyl (thio) ureas, process for their preparation and their use in the manufacture of pharmaceutical preparations
CA2195697A1 (en) * 1996-02-02 1997-08-03 Masahumi Kitano Novel substituted guanidine derivatives, process for production thereof, and pharmaceutical uses thereof
DE19621319A1 (en) * 1996-05-28 1997-12-04 Hoechst Ag Bis-ortho-substituted benzoylguanidines, process for their preparation, their use as a medicament or diagnostic agent and medicament containing them
DE19737224A1 (en) 1997-08-27 1999-03-18 Hoechst Marion Roussel De Gmbh Pharmaceutical preparation for cardiovascular treatment
DE10001879A1 (en) * 2000-01-19 2001-07-19 Aventis Pharma Gmbh New benzoylguanidine derivatives are Na+/H+ exchange inhibitors useful for the treatment and prevention of e.g. ischemic disorders, infarction, arrhythmia, angina pectoris and stroke
WO2003099773A1 (en) 2002-05-24 2003-12-04 Millennium Pharmaceuticals, Inc. Ccr9 inhibitors and methods of use thereof
US7741519B2 (en) 2007-04-23 2010-06-22 Chemocentryx, Inc. Bis-aryl sulfonamides
US7420055B2 (en) 2002-11-18 2008-09-02 Chemocentryx, Inc. Aryl sulfonamides
US7227035B2 (en) 2002-11-18 2007-06-05 Chemocentryx Bis-aryl sulfonamides
ATE517102T1 (en) 2002-11-18 2011-08-15 Chemocentryx Inc ARYLSULFONAMIDE

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US3780027A (en) * 1970-04-29 1973-12-18 Merck & Co Inc Anthranilic acid derivatives
DE3929582A1 (en) * 1989-09-06 1991-03-07 Hoechst Ag BENZOYLGUANIDINE, METHOD FOR THE PRODUCTION THEREOF, THEIR USE AS A MEDICINE AND THE MEDICINE CONTAINING IT

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6169107B1 (en) 1993-04-28 2001-01-02 Sumitomo Pharmaceutical Co., Ltd. Indoloylguanidine derivatives
US6248772B1 (en) 1993-04-28 2001-06-19 Sumitomo Pharmaceuticals Co., Ltd. Indoloylguanidine derivatives
EP0921117A2 (en) † 1993-08-24 1999-06-09 Hoechst Aktiengesellschaft Acylguanidines
EP0921117A3 (en) * 1993-08-24 1999-09-22 Hoechst Aktiengesellschaft Acylguanidines
US6436999B1 (en) 1993-08-24 2002-08-20 Hoechst Aktiengesellschaft Diacyl-substituted guanidines, a process for their preparation, their use as medicine or diagnostic aid, and medicine containing them
US6632840B1 (en) 1993-08-24 2003-10-14 Hoechst Aktiengesellschaft Monoacyl-substituted guanidines, a process for their preparation, their use as a medicament or diagnostic aid, and pharmaceutical compositions containing them
EP0921117B2 (en) † 1993-08-24 2009-01-07 Sanofi-Aventis Deutschland GmbH Acylguanidines
US5849796A (en) * 1994-08-28 1998-12-15 Merck Patent Gelsellschaft Mit Beschrankter Haftung Ortho-substituted benzoil acid derivatives
US5753680A (en) * 1994-08-31 1998-05-19 Merck Patent Gesellschaft Mit Beschrankter Haftung Heterocyclyl-benzoylguanidines

Also Published As

Publication number Publication date
GR3025523T3 (en) 1998-02-27
ES2108144T3 (en) 1997-12-16
AU3301493A (en) 1993-08-19
EP0556673A1 (en) 1993-08-25
JPH069545A (en) 1994-01-18
NZ245895A (en) 1995-02-24
ZA93985B (en) 1993-09-20
FI930602A (en) 1993-08-16
NO179002C (en) 1996-07-17
DK0556673T3 (en) 1998-04-14
FI930602A0 (en) 1993-02-11
CA2089440C (en) 2006-04-11
HU220219B (en) 2001-11-28
HUT65868A (en) 1994-07-28
JP3558224B2 (en) 2004-08-25
NO930511D0 (en) 1993-02-12
EP0556673B1 (en) 1997-09-17
AU658262B2 (en) 1995-04-06
NO930511L (en) 1993-08-16
ATE158278T1 (en) 1997-10-15
HU9300369D0 (en) 1993-04-28
FI112076B (en) 2003-10-31
DE59307360D1 (en) 1997-10-23
IL104714A0 (en) 1993-06-10
IL104714A (en) 1996-12-05
NO179002B (en) 1996-04-09

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