CA2587444C - Guanidine derivatives as inhibitors of ddah - Google Patents

Guanidine derivatives as inhibitors of ddah Download PDF

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Publication number
CA2587444C
CA2587444C CA2587444A CA2587444A CA2587444C CA 2587444 C CA2587444 C CA 2587444C CA 2587444 A CA2587444 A CA 2587444A CA 2587444 A CA2587444 A CA 2587444A CA 2587444 C CA2587444 C CA 2587444C
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CA
Canada
Prior art keywords
alkyl
het
hydrogen
phenyl
amino
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.)
Expired - Lifetime
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CA2587444A
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English (en)
French (fr)
Other versions
CA2587444A1 (en
Inventor
Patrick John Thompson Vallance
James Mitchell Leiper
David Lawrence Selwood
Sharon Rossiter
Basil Hartzoulakis
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.)
Critical Pressure Ltd
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UCL Business Ltd
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Publication date
Priority claimed from GB0425039A external-priority patent/GB0425039D0/en
Priority claimed from GB0510348A external-priority patent/GB0510348D0/en
Application filed by UCL Business Ltd filed Critical UCL Business Ltd
Publication of CA2587444A1 publication Critical patent/CA2587444A1/en
Application granted granted Critical
Publication of CA2587444C publication Critical patent/CA2587444C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
    • C07C279/04—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton
    • C07C279/14—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton being further substituted by carboxyl groups
    • 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
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
    • A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid or pantothenic acid
    • A61K31/198—Alpha-amino acids, e.g. alanine or edetic acid [EDTA]
    • 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
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • A61K31/223—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin of alpha-aminoacids
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A61K31/4453—Non condensed piperidines, e.g. piperocaine only substituted in position 1, e.g. propipocaine, diperodon
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • A61K31/5375—1,4-Oxazines, e.g. morpholine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/06—Antiasthmatics
    • 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
    • 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
    • A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
    • 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
    • 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
    • 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
    • A61P9/10—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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
    • C07C279/16—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
    • C07C279/18—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to carbon atoms of six-membered aromatic rings
    • 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
    • C07C323/23—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 nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C323/39—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 nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
    • C07C323/43—Y being a hetero atom
    • C07C323/44—X or Y being nitrogen atoms
    • 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
    • C07D295/16—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 acylated on ring nitrogen atoms
    • C07D295/20—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 acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
    • C07D295/215—Radicals derived from nitrogen analogues of carbonic acid
    • 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
    • C07D295/28—Nitrogen atoms
    • C07D295/32—Nitrogen atoms acylated with carboxylic or carbonic acids, or their nitrogen or sulfur analogues
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring

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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)
  • Epidemiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Neurosurgery (AREA)
  • Rheumatology (AREA)
  • Pulmonology (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Emergency Medicine (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Oncology (AREA)
  • Immunology (AREA)
  • Hematology (AREA)
  • Urology & Nephrology (AREA)
  • Communicable Diseases (AREA)
  • Diabetes (AREA)
  • Vascular Medicine (AREA)
  • Pain & Pain Management (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Furan Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
CA2587444A 2004-11-12 2005-11-11 Guanidine derivatives as inhibitors of ddah Expired - Lifetime CA2587444C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
GB0425039A GB0425039D0 (en) 2004-11-12 2004-11-12 Chemical compounds
GB0425039.5 2004-11-12
GB0510348.6 2005-05-20
GB0510348A GB0510348D0 (en) 2005-05-20 2005-05-20 Chemical compounds
PCT/GB2005/004361 WO2006051314A2 (en) 2004-11-12 2005-11-11 Guanidine derivatives as inhibitors of ddah

Publications (2)

Publication Number Publication Date
CA2587444A1 CA2587444A1 (en) 2006-05-18
CA2587444C true CA2587444C (en) 2013-09-10

Family

ID=35908037

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2587444A Expired - Lifetime CA2587444C (en) 2004-11-12 2005-11-11 Guanidine derivatives as inhibitors of ddah

Country Status (6)

Country Link
US (1) US8063104B2 (https=)
EP (1) EP1828109B1 (https=)
JP (1) JP5274838B2 (https=)
AU (1) AU2005303610B2 (https=)
CA (1) CA2587444C (https=)
WO (1) WO2006051314A2 (https=)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8063104B2 (en) 2004-11-12 2011-11-22 Ucl Business Plc Guanidine derivatives as inhibitors of DDAH
EP3192788A1 (en) * 2006-10-03 2017-07-19 Arbutus Biopharma Corporation Lipid containing formulations
DE102008061247A1 (de) * 2008-12-10 2010-06-24 Christian-Albrechts-Universität Zu Kiel Inhibitoren der Dimethylarginin Dimethylaminohydrolase
WO2013123033A1 (en) * 2012-02-14 2013-08-22 The Board Of Trustees Of The Leland Stanford Junior University Dimethylarginine dimethylaminohydrolase inhibitors and methods of use thereof
WO2014160947A1 (en) * 2013-03-29 2014-10-02 The Board Of Trustees Of The Leland Stanford Junior University Dimethylarginine dimethylaminohydrolase inhibitors and methods of use thereof
US10226418B2 (en) 2014-05-12 2019-03-12 Susie Q, Ltd. Arginine-containing topical composition
AU2018354090B2 (en) 2017-10-23 2024-10-24 Epitracker, Inc. Fatty acid analogs and their use in the treatment of conditions related to metabolic syndrome
AU2019274431B2 (en) 2018-05-23 2025-03-13 Epitracker, Inc. Compositions and methods for diagnosis and treatment of conditions related to the quality of aging and longevity
EP3908374A4 (en) * 2019-01-09 2022-12-28 Epitracker, Inc. COMPOSITIONS AND METHODS FOR DIAGNOSIS AND TREATMENT OF NEURODEGENERATIVE DISEASES
WO2020180814A1 (en) 2019-03-04 2020-09-10 Epitracker, Inc. Fatty acid analogs and their use in the treatment of cognitive impairment, behavioral conditions, and chronic pain
EP4426130A1 (en) 2021-11-03 2024-09-11 Epitracker, Inc. Pentadecanoylcarnitine for treatment of conditions related to the quality of aging and longevity
CA3238205A1 (en) 2021-11-12 2023-05-19 Rajaram Samant A synergistic composition for activating intracellular secondary messenger(camp) pathway

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FI832053L (fi) 1982-06-10 1983-12-11 Syntex Inc Nonapeptid- och dekapeptidanaloger av lhrh anvaendbara som lhrh-antagonister samt deras framstaellningsfoerfarande
US4530920A (en) * 1983-11-07 1985-07-23 Syntex (U.S.A.) Inc. Nonapeptide and decapeptide analogs of LHRH, useful as LHRH agonist
US4659693A (en) * 1984-04-30 1987-04-21 Syntex (U.S.A.) Inc. N,N'-dialkyl substituted guanidino amino acyl residue substituted GRF-analog peptides
US4686283A (en) * 1985-04-16 1987-08-11 Syntex (U.S.A.) Inc. Analogs of transforming and epidermal growth factor fragments for therapy and diagnosis
IT1201511B (it) * 1985-12-23 1989-02-02 Italfarmaco Spa Derivati citoprotettivi in patologie a base ischemica,loro preparazione e composizioni che li cntengono
US5352796A (en) * 1989-10-30 1994-10-04 The Salk Institute For Biological Studies Amino acids useful in making GnRH analogs
US5318992A (en) * 1990-02-26 1994-06-07 Merrell Dow Pharmaceuticals Inc. Inhibitors of nitric oxide biosynthesis
MX9100717A (es) 1990-08-24 1992-04-01 Syntex Inc Antagonistas de la bradiquinina
US5554638A (en) * 1993-05-24 1996-09-10 Duke University Methods for improving therapeutic effectiveness of agents for the treatment of solid tumors and other disorders
US5859295A (en) * 1994-12-05 1999-01-12 University Of Kentucky Research Foundation Canavanine analogs and their use as chemotherapeutic agents
GB9504350D0 (en) * 1995-03-04 1995-04-26 Sod Conseils Rech Applic Arginine derivatives
BR9813554A (pt) 1997-12-12 2001-07-24 Fuji Yakuhin Kogyo Kk Composto, uso do mesmo, processo para produzi-lo, composição farmacêutica ou veterinária, e, inibidor de metaloproteinase
BR9912124A (pt) 1998-07-16 2001-09-25 Univation Tech Llc Co-catalisadores de ácido de lewis à base de alumìnio para a polimerização de olefina
JP2002534408A (ja) 1999-01-02 2002-10-15 アベンティス・ファーマ・ドイチユラント・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング アリールアルカノイル誘導体、その調製のための方法、その使用およびそれらを含有する医薬組成物
EP1022268A1 (en) 1999-01-02 2000-07-26 Aventis Pharma Deutschland GmbH Arylalkanoyl derivatives, processes for their preparation, their use and pharmaceutical compositions containing them
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Also Published As

Publication number Publication date
AU2005303610A1 (en) 2006-05-18
WO2006051314A3 (en) 2006-06-22
WO2006051314A8 (en) 2006-09-28
WO2006051314A2 (en) 2006-05-18
EP1828109A2 (en) 2007-09-05
AU2005303610B2 (en) 2011-07-21
CA2587444A1 (en) 2006-05-18
US20090069331A1 (en) 2009-03-12
JP5274838B2 (ja) 2013-08-28
EP1828109B1 (en) 2013-06-05
US8063104B2 (en) 2011-11-22
JP2008519815A (ja) 2008-06-12

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