WO2000027378A3 - Cystine derivatives as therapeutic agents for matrix metalloprotease related diseases - Google Patents

Cystine derivatives as therapeutic agents for matrix metalloprotease related diseases Download PDF

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Publication number
WO2000027378A3
WO2000027378A3 PCT/EP1999/008460 EP9908460W WO0027378A3 WO 2000027378 A3 WO2000027378 A3 WO 2000027378A3 EP 9908460 W EP9908460 W EP 9908460W WO 0027378 A3 WO0027378 A3 WO 0027378A3
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WO
WIPO (PCT)
Prior art keywords
aromatic
heterocyclic ring
aromatic carbocyclic
diseases
interrupted
Prior art date
Application number
PCT/EP1999/008460
Other languages
French (fr)
Other versions
WO2000027378A2 (en
Inventor
Frank Grams
Hans-Willi Krell
Herbert Leinert
Gerd Zimmermann
Original Assignee
Roche Diagnostics Gmbh
Frank Grams
Krell Hans Willi
Herbert Leinert
Gerd Zimmermann
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 Roche Diagnostics Gmbh, Frank Grams, Krell Hans Willi, Herbert Leinert, Gerd Zimmermann filed Critical Roche Diagnostics Gmbh
Priority to KR1020017005616A priority Critical patent/KR20010100983A/en
Priority to BR9915127-8A priority patent/BR9915127A/en
Priority to JP2000580607A priority patent/JP2002529404A/en
Priority to EP99971709A priority patent/EP1143960A2/en
Priority to AU13796/00A priority patent/AU1379600A/en
Priority to CA002348946A priority patent/CA2348946A1/en
Publication of WO2000027378A2 publication Critical patent/WO2000027378A2/en
Publication of WO2000027378A3 publication Critical patent/WO2000027378A3/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
    • 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
    • A61K31/16—Amides, e.g. hydroxamic acids
    • 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
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
    • 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
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
    • A61K31/166—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the carbon of a carboxamide group directly attached to the aromatic ring, e.g. procainamide, procarbazine, metoclopramide, labetalol
    • 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
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A61K31/18—Sulfonamides
    • 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
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/27—Esters, e.g. nitroglycerine, selenocyanates of carbamic or thiocarbamic acids, meprobamate, carbachol, neostigmine
    • 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
    • A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
    • A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • 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
    • 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
    • A61P35/00—Antineoplastic agents
    • A61P35/04—Antineoplastic agents specific for metastasis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/60—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton with the carbon atom of at least one of the carboxyl groups bound to nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
    • 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
    • C07D295/145—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 attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/15—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 attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
    • C07C2603/18—Fluorenes; Hydrogenated fluorenes

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Epidemiology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Rheumatology (AREA)
  • Neurosurgery (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Oncology (AREA)
  • Psychiatry (AREA)
  • Hospice & Palliative Care (AREA)
  • Diabetes (AREA)
  • Pain & Pain Management (AREA)
  • Hematology (AREA)
  • Immunology (AREA)
  • Dermatology (AREA)
  • Communicable Diseases (AREA)
  • Emergency Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Subject of the present invention are pharmaceutical compositions containing nonpeptidic cystine derivatives of general formula (I) wherein R1 and R3 may be the same or different and are selected from hydrogen, an aromatic or non-aromatic carbocyclic or heterocyclic ring or a linear or branched saturated or unsaturated alkyl group of 1 to 15 carbon atoms which can be interrupted by a hetero atom and which can be substituted by an aromatic or non-aromatic carbocyclic or heterocyclic ring. R2 and R4 may be the same or different and are selected from hydrogen, a linear or branched, saturated or unsaturated alkyl group of 1 to 15 carbon atoms which can be interrupted by a hetero atom and which can be substituted by an aromatic or non-aromatic carbocyclic or heterocyclic ring and A is a valency bond or a -CO-, -SO2-, -NHCO-, -NHCS- or -O-CO- group, their pharmacologically acceptable salts and optically active forms thereof and pharmaceutically acceptable carriers, for the treatment of diseases selected from tumor growth and metastasis, inflammatory diseases like osteo- and rheumatoid arthritis, osteoporosis, multiple sclerosis, periodontitis, restenosis, diseases caused by bacteria such as meningitis, sun-induced skin aging and Alzheimers disease and new compounds.
PCT/EP1999/008460 1998-11-06 1999-11-05 Cystine derivatives as therapeutic agents for matrix metalloprotease related diseases WO2000027378A2 (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
KR1020017005616A KR20010100983A (en) 1998-11-06 1999-11-05 Cystine derivatives as therapeutic agents for matrix metalloprotease related diseases
BR9915127-8A BR9915127A (en) 1998-11-06 1999-11-05 Cystine derivatives as therapeutic agents for diseases related to matrix metalloprotease
JP2000580607A JP2002529404A (en) 1998-11-06 1999-11-05 Cystine derivatives as therapeutics for substrate metalloprotease-related diseases
EP99971709A EP1143960A2 (en) 1998-11-06 1999-11-05 Cystine derivatives as therapeutic agents for matrix metalloprotease related diseases
AU13796/00A AU1379600A (en) 1998-11-06 1999-11-05 Cystine derivatives as therapeutic agents for matrix metalloprotease related diseases
CA002348946A CA2348946A1 (en) 1998-11-06 1999-11-05 Cystine derivatives as therapeutic agents for matrix metalloprotease related diseases

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP98121073.5 1998-11-06
EP98121073 1998-11-06

Publications (2)

Publication Number Publication Date
WO2000027378A2 WO2000027378A2 (en) 2000-05-18
WO2000027378A3 true WO2000027378A3 (en) 2001-09-20

Family

ID=8232930

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1999/008460 WO2000027378A2 (en) 1998-11-06 1999-11-05 Cystine derivatives as therapeutic agents for matrix metalloprotease related diseases

Country Status (11)

Country Link
EP (1) EP1143960A2 (en)
JP (1) JP2002529404A (en)
KR (1) KR20010100983A (en)
CN (1) CN1346272A (en)
AR (1) AR025135A1 (en)
AU (1) AU1379600A (en)
BR (1) BR9915127A (en)
CA (1) CA2348946A1 (en)
TR (1) TR200101222T2 (en)
WO (1) WO2000027378A2 (en)
ZA (1) ZA200103605B (en)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN100453531C (en) 1998-10-09 2009-01-21 味之素株式会社 Cysteine derivatives
JP2002226457A (en) * 2001-02-02 2002-08-14 Ajinomoto Co Inc New cystine derivative and inflammation factor activation inhibitor
EP2586445A1 (en) * 2005-04-15 2013-05-01 University Of North Carolina At Chapel Hill Methods of facilitating cell survival using neurotrophin mimetics
US10273219B2 (en) 2009-11-12 2019-04-30 Pharmatrophix, Inc. Crystalline forms of neurotrophin mimetic compounds and their salts
AU2010319349B2 (en) 2009-11-12 2015-07-16 Pharmatrophix, Inc. Crystalline forms of neurotrophin mimetic compounds and their salts
WO2016199796A1 (en) * 2015-06-08 2016-12-15 公立大学法人大阪府立大学 Non-peptidic gapdh aggregation inhibitor

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2605182A1 (en) * 1975-02-12 1976-08-26 Eznpk Biolog I Mediko Biolog P MEDICINE AGAINST TUMOR

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2605182A1 (en) * 1975-02-12 1976-08-26 Eznpk Biolog I Mediko Biolog P MEDICINE AGAINST TUMOR

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
MÜLLER ET AL: "Non-peptide cysteine derivatives as inhibitors of matrix of matrix metalloproteases", BIOL. CHEM., vol. 378, 1997, pages 1475 - 1480, XP002105604 *

Also Published As

Publication number Publication date
AR025135A1 (en) 2002-11-13
WO2000027378A2 (en) 2000-05-18
BR9915127A (en) 2001-07-31
CN1346272A (en) 2002-04-24
CA2348946A1 (en) 2000-05-18
KR20010100983A (en) 2001-11-14
EP1143960A2 (en) 2001-10-17
TR200101222T2 (en) 2001-12-21
AU1379600A (en) 2000-05-29
JP2002529404A (en) 2002-09-10
ZA200103605B (en) 2001-12-11

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