AU3301493A - 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
AU3301493A
AU3301493A AU33014/93A AU3301493A AU3301493A AU 3301493 A AU3301493 A AU 3301493A AU 33014/93 A AU33014/93 A AU 33014/93A AU 3301493 A AU3301493 A AU 3301493A AU 3301493 A AU3301493 A AU 3301493A
Authority
AU
Australia
Prior art keywords
equal
medicament
ortho
alkyl
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
AU33014/93A
Other versions
AU658262B2 (en
Inventor
Udo Albus
Heinrich Englert
Florian Lang
Hans-Jochen Lang
Wolfgang Scholz
Andreas Weichert
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sanofi Aventis Deutschland GmbH
Original Assignee
Sanofi Aventis Deutschland GmbH
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 Sanofi Aventis Deutschland GmbH filed Critical Sanofi Aventis Deutschland GmbH
Publication of AU3301493A publication Critical patent/AU3301493A/en
Application granted granted Critical
Publication of AU658262B2 publication Critical patent/AU658262B2/en
Assigned to AVENTIS PHARMA DEUTSCHLAND GMBH reassignment AVENTIS PHARMA DEUTSCHLAND GMBH Alteration of Name(s) in Register under S187 Assignors: HOECHST AKTIENGESELLSCHAFT
Assigned to SANOFI-AVENTIS DEUTSCHLAND GMBH reassignment SANOFI-AVENTIS DEUTSCHLAND GMBH Request to Amend Deed and Register Assignors: AVENTIS PHARMA DEUTSCHLAND GMBH
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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

Abstract

Ortho-substituted benzoylguanidines of the formula I <IMAGE> where: R(1) is equal to halogen, alkyl, -X-R(6), where X is equal to O, S, NR(7) or Y-ZO and R(6) is equal to H, (cyclo)(halo)alkyl(methyl), -CnH2n-phenyl, R(3) is equal to H, -X-R(6), R(2) and R(4) are equal to R(11)-SO1-2-, (di)-alkyl-N-SO2-, or one of the two radicals R(2) or R(4) is equal to hydrogen or is defined as R(1), R(5) is equal to H, methyl, F, Cl, methoxy, and their pharmaceutically acceptable salts. They are obtained by a process in which compounds of the formula II <IMAGE> in which R(1) to R(5) have the meaning mentioned and L represents a leaving group which can be easily substituted nucleophilically, are reacted with guanidine. The compounds I are used for producing a medicament for the treatment and the prophylaxis of heart-rhythm disorders and ischaemically induced damage, as well as for producing a medicament for the inhibition of cell proliferation.
AU33014/93A 1992-02-15 1993-02-12 Ortho-substituted benzoylguanidines, process for their preparation, their use as a medicament or diagnostic and medicaments containing them Ceased AU658262B2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4204576 1992-02-15
DE4204576 1992-02-15

Publications (2)

Publication Number Publication Date
AU3301493A true AU3301493A (en) 1993-08-19
AU658262B2 AU658262B2 (en) 1995-04-06

Family

ID=6451808

Family Applications (1)

Application Number Title Priority Date Filing Date
AU33014/93A Ceased AU658262B2 (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 (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU658261B2 (en) * 1992-02-15 1995-04-06 Hoechst Aktiengesellschaft Amino-substituted benzoylguanidines, process for their preparation, their use as a medicament and medicament containing them
US5708034A (en) * 1995-11-03 1998-01-13 Hoechst Aktiengesellschaft Substituted sulfonimidamides, processes for their preparation, their use as a medicament or diagnostic, and medicament comprising them
US5731350A (en) * 1995-11-20 1998-03-24 Hoechst Aktiengesellschaft Substituted benzenedicarboxylic acid diguanides, process for their preparation, their use as a medicament or diagnostic, and medicament containing them
US5747541A (en) * 1995-09-27 1998-05-05 Hoechst Aktiengesellschaft Substituted benzoylguanidines, a process for their preparation, their use as medicament of diagnostic agent, and medicament comprising them
US5811448A (en) * 1995-12-14 1998-09-22 Hoechst Aktiengesellschaft Substituted chromanysulfonyl (thio) ureas, processing for their preparation and pharmaceutical uses thereof
AU698225B2 (en) * 1994-10-22 1998-10-29 Merck Patent Gesellschaft Mit Beschrankter Haftung Alkyl-5-methylsulfonylbenzoylguanidin derivatives
US5834454A (en) * 1996-02-02 1998-11-10 Sumitomo Pharmaceuticals Company, Limited Substituted guanidine derivatives, process for production thereof, and pharmaceutical uses thereof
US5856344A (en) * 1995-11-14 1999-01-05 Hoechst Aktiengesellschaft Sulfonylamino-substituted benzoylguanidines, a process for their preparation, their use as a medicament or diagnostic aid, and medicament containing them
CN1064954C (en) * 1993-08-27 2001-04-25 赫彻斯特股份公司 Orthosubstituted benzoylguanidine, preparation of same, pharmaceutical containing same and application of same

Families Citing this family (25)

* 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
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
DE4328352A1 (en) * 1993-08-24 1995-03-02 Hoechst Ag Substituted N, N'-di-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
DE4430212A1 (en) * 1994-08-28 1996-02-29 Merck Patent Gmbh Ortho-substituted benzoic acid derivatives
DE4430861A1 (en) * 1994-08-31 1996-03-07 Merck Patent Gmbh Heterocyclyl-benzoylguanidines
DE4430916A1 (en) * 1994-08-31 1996-03-07 Merck Patent Gmbh Alkyl benzoylguanidine 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
ATE183498T1 (en) * 1995-04-18 1999-09-15 Hoechst Ag SUBSTITUTED INDENOYLGUANIDINES WITH ANTIARRHYTHMIC AND CARDIOPROTECTIVE EFFECTS
DE19517848A1 (en) * 1995-05-16 1996-11-21 Merck Patent Gmbh Fluorine-containing benzoylguanidines
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
CA2485681C (en) 2002-05-24 2012-10-16 Millennium Pharmaceuticals, Inc. Ccr9 inhibitors and methods of use thereof
EP2256116A3 (en) 2002-11-18 2011-11-16 ChemoCentryx, Inc. Aryl sulfonamides
US7227035B2 (en) 2002-11-18 2007-06-05 Chemocentryx Bis-aryl sulfonamides
US7420055B2 (en) 2002-11-18 2008-09-02 Chemocentryx, Inc. Aryl sulfonamides
US7741519B2 (en) 2007-04-23 2010-06-22 Chemocentryx, Inc. Bis-aryl sulfonamides

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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 (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU658261B2 (en) * 1992-02-15 1995-04-06 Hoechst Aktiengesellschaft Amino-substituted benzoylguanidines, process for their preparation, their use as a medicament and medicament containing them
CN1064954C (en) * 1993-08-27 2001-04-25 赫彻斯特股份公司 Orthosubstituted benzoylguanidine, preparation of same, pharmaceutical containing same and application of same
AU698225B2 (en) * 1994-10-22 1998-10-29 Merck Patent Gesellschaft Mit Beschrankter Haftung Alkyl-5-methylsulfonylbenzoylguanidin derivatives
US5747541A (en) * 1995-09-27 1998-05-05 Hoechst Aktiengesellschaft Substituted benzoylguanidines, a process for their preparation, their use as medicament of diagnostic agent, and medicament comprising them
US5708034A (en) * 1995-11-03 1998-01-13 Hoechst Aktiengesellschaft Substituted sulfonimidamides, processes for their preparation, their use as a medicament or diagnostic, and medicament comprising them
US5856344A (en) * 1995-11-14 1999-01-05 Hoechst Aktiengesellschaft Sulfonylamino-substituted benzoylguanidines, a process for their preparation, their use as a medicament or diagnostic aid, and medicament containing them
US5731350A (en) * 1995-11-20 1998-03-24 Hoechst Aktiengesellschaft Substituted benzenedicarboxylic acid diguanides, process for their preparation, their use as a medicament or diagnostic, and medicament containing them
US5811448A (en) * 1995-12-14 1998-09-22 Hoechst Aktiengesellschaft Substituted chromanysulfonyl (thio) ureas, processing for their preparation and pharmaceutical uses thereof
US5834454A (en) * 1996-02-02 1998-11-10 Sumitomo Pharmaceuticals Company, Limited Substituted guanidine derivatives, process for production thereof, and pharmaceutical uses thereof
US5977100A (en) * 1996-02-02 1999-11-02 Sumitomo Pharmaceuticals Company, Limited Substituted guanidine derivatives, process for production thereof, and pharmaceutical uses thereof
US6271251B1 (en) 1996-02-02 2001-08-07 Sumitomo Pharmaceuticals Company Limited Substituted guanidine derivatives, process for production thereof, and pharmaceutical uses thereof

Also Published As

Publication number Publication date
FI112076B (en) 2003-10-31
GR3025523T3 (en) 1998-02-27
NO179002C (en) 1996-07-17
JP3558224B2 (en) 2004-08-25
EP0556673A1 (en) 1993-08-25
NZ245895A (en) 1995-02-24
NO930511L (en) 1993-08-16
NO930511D0 (en) 1993-02-12
HU220219B (en) 2001-11-28
IL104714A0 (en) 1993-06-10
FI930602A0 (en) 1993-02-11
EP0556673B1 (en) 1997-09-17
DK0556673T3 (en) 1998-04-14
ES2108144T3 (en) 1997-12-16
HU9300369D0 (en) 1993-04-28
JPH069545A (en) 1994-01-18
ZA93985B (en) 1993-09-20
AU658262B2 (en) 1995-04-06
IL104714A (en) 1996-12-05
CA2089440A1 (en) 1993-08-16
DE59307360D1 (en) 1997-10-23
FI930602A (en) 1993-08-16
CA2089440C (en) 2006-04-11
HUT65868A (en) 1994-07-28
NO179002B (en) 1996-04-09
ATE158278T1 (en) 1997-10-15

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