CA2372962C - Novel interleukin-1 and tumor necrosis factor-.alpha. modulators, syntheses of said modulators and methods of using said modulators - Google Patents

Novel interleukin-1 and tumor necrosis factor-.alpha. modulators, syntheses of said modulators and methods of using said modulators Download PDF

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Publication number
CA2372962C
CA2372962C CA002372962A CA2372962A CA2372962C CA 2372962 C CA2372962 C CA 2372962C CA 002372962 A CA002372962 A CA 002372962A CA 2372962 A CA2372962 A CA 2372962A CA 2372962 C CA2372962 C CA 2372962C
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alkenyl
alkyl
substituted
hydrogen
compound
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Expired - Fee Related
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CA002372962A
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English (en)
French (fr)
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CA2372962A1 (en
Inventor
Michael Palladino
Emmanuel A. Theodorakis
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Nereus Pharmaceuticals Inc
University of California, San Diego
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Nereus Pharmaceuticals Inc
University of California, San Diego
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C62/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C62/30—Unsaturated compounds
    • C07C62/32—Unsaturated compounds containing hydroxy or O-metal 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
    • A61K31/12—Ketones
    • 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
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • 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
    • A61P11/02—Nasal agents, e.g. decongestants
    • 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
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/16—Otologicals
    • 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
    • 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
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • A61P31/06—Antibacterial agents for tuberculosis
    • 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
    • A61P31/12—Antivirals
    • 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
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
    • 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
    • A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C61/16—Unsaturated compounds
    • C07C61/28—Unsaturated compounds polycyclic
    • C07C61/29—Unsaturated compounds polycyclic having a carboxyl group bound to a condensed ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C61/16—Unsaturated compounds
    • C07C61/35—Unsaturated compounds having unsaturation outside the rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C69/753—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring of polycyclic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/05—Isotopically modified compounds, e.g. labelled
    • 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
    • C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
    • C07C2603/26—Phenanthrenes; Hydrogenated phenanthrenes

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Epidemiology (AREA)
  • Immunology (AREA)
  • Diabetes (AREA)
  • Emergency Medicine (AREA)
  • Communicable Diseases (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Oncology (AREA)
  • Pulmonology (AREA)
  • Pain & Pain Management (AREA)
  • Otolaryngology (AREA)
  • Obesity (AREA)
  • Virology (AREA)
  • Endocrinology (AREA)
  • Rheumatology (AREA)
  • Dermatology (AREA)
  • Hematology (AREA)
  • Transplantation (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (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)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Hydrogenated Pyridines (AREA)
CA002372962A 1999-05-14 2000-05-12 Novel interleukin-1 and tumor necrosis factor-.alpha. modulators, syntheses of said modulators and methods of using said modulators Expired - Fee Related CA2372962C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US13429599P 1999-05-14 1999-05-14
US60/134,295 1999-05-14
US18685300P 2000-03-03 2000-03-03
US60/186,853 2000-03-03
PCT/US2000/013202 WO2000073253A1 (en) 1999-05-14 2000-05-12 NOVEL INTERLEUKIN-1 AND TUMOR NECROSIS FACTOR-α MODULATORS, SYNTHESES OF SAID MODULATORS AND METHODS OF USING SAID MODULATORS

Publications (2)

Publication Number Publication Date
CA2372962A1 CA2372962A1 (en) 2000-12-07
CA2372962C true CA2372962C (en) 2008-04-08

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CA002372962A Expired - Fee Related CA2372962C (en) 1999-05-14 2000-05-12 Novel interleukin-1 and tumor necrosis factor-.alpha. modulators, syntheses of said modulators and methods of using said modulators

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Country Link
US (3) US6365768B1 (enExample)
EP (2) EP1178952B1 (enExample)
JP (2) JP5059996B2 (enExample)
KR (3) KR20060110013A (enExample)
CN (1) CN1361760A (enExample)
AT (2) ATE370928T1 (enExample)
AU (2) AU783372B2 (enExample)
BR (1) BR0011522A (enExample)
CA (1) CA2372962C (enExample)
DE (2) DE60043400D1 (enExample)
DK (1) DK1178952T5 (enExample)
ES (2) ES2337264T3 (enExample)
IL (3) IL146221A0 (enExample)
MX (1) MXPA01011613A (enExample)
NZ (3) NZ529505A (enExample)
PT (2) PT1178952E (enExample)
WO (1) WO2000073253A1 (enExample)

Families Citing this family (41)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2211030T3 (es) * 1998-01-26 2004-07-01 Sae Han Pharm. Co., Ltd. Derivados diterpenos y agentes analgesicos anti-inflamatorios que comprenden a los mismos.
US6326507B1 (en) 1998-06-19 2001-12-04 Trustees Of Dartmouth College Therapeutic compounds and methods of use
US7119223B2 (en) * 1999-05-14 2006-10-10 Nereus Pharmaceuticals, Inc. Interleukin-1 and tumor necrosis factor-α modulators, synthesis of said modulators and their enantiomers and methods of using said modulators
PT1178952E (pt) * 1999-05-14 2007-12-04 Univ California Novos moduladores da interleucina-1 e do factor alfa de necrose tumoral, síntese dos referidos moduladores e métodos de utilização dos referidos moduladores
US7435755B2 (en) 2000-11-28 2008-10-14 The Trustees Of Dartmouth College CDDO-compounds and combination therapies thereof
WO2002079137A1 (en) * 2001-03-28 2002-10-10 Nereus Pharmaceuticals, Inc. Interleukin-1 and tumor necrosis factor-alpha modulators and their enantiomers, their synthesis and use
US20030087334A1 (en) * 2001-04-02 2003-05-08 Libraria, Inc. Method of flexibly generating diverse reaction chemistries
DK1465615T3 (da) 2002-01-15 2012-11-12 Dartmouth College Tricykliske bisenonderivater og fremgangsmåder til anvendelse heraf
WO2003061553A2 (en) * 2002-01-25 2003-07-31 Korea Research Institute Of Bioscience And Biotechnology An extract of acanthopanax koreanum for the treatment or prevention of hepatitis or the liver protective drug
WO2005084141A2 (en) * 2004-03-03 2005-09-15 Korea Research Institute Of Bioscience And Biotechnology Novel abietane diterpenoid compound, and composition comprising extract of torreya nucifera, or abietane diterpenoid compounds or terpenoid compounds isolated from them for prevention and treatment of cardiovascular disease
ATE556046T1 (de) 2005-07-21 2012-05-15 Nereus Pharmaceuticals Inc Interleukin-1- und tumornekrosefaktor-a- modulatoren, synthese solcher modulatoren und verfahren unter anwendung solcher modulatoren
EP2094651A1 (en) 2006-11-17 2009-09-02 Trustees Of Dartmouth College Synthesis and biological activities of new tricyclic-bis-enones (tbes)
US8921340B2 (en) 2006-11-17 2014-12-30 Trustees Of Dartmouth College Methods for using synthetic triterpenoids in the treatment of bone or cartilage diseases or conditions
WO2008064132A2 (en) 2006-11-17 2008-05-29 Trustees Of Dartmouth College Synthetic triterpenoids and tricyclic-bis-enones for use in stimulating bone and cartilage growth
EP1925301A1 (en) * 2006-11-24 2008-05-28 DSMIP Assets B.V. Use of tricyclic diterpenes and their derivatives for the treatment, co-treatment or prevention of inflammatory disorders and/or joint disorders
US7875853B2 (en) * 2007-07-23 2011-01-25 Honeywell International Inc. Low-cost PIR scanning mechanism
ME03529B (me) 2008-01-11 2020-04-20 Reata Pharmaceuticals Inc Sintetički triterpenoidi i metode njihove upotrebe u tretmanu bolesti
RS58392B1 (sr) 2008-04-18 2019-04-30 Reata Pharmaceuticals Inc Antioksidantni modulatori inflamacije: derivati oleanoličke kiseline sa amino i drugim modifikacijama na c-17
EP2279197B1 (en) 2008-04-18 2014-11-05 Reata Pharmaceuticals, Inc. Antioxidant inflammation modulators: oleanolic acid derivatives with saturation in the c-ring
HUE033288T2 (en) 2008-04-18 2017-11-28 Reata Pharmaceuticals Inc Antioxidant inflammation modulators: C-17 homologated oleic acid derivatives
TW201006474A (en) 2008-04-18 2010-02-16 Reata Pharmaceuticals Inc Natural products including an anti-flammatory pharmacore and methods of use
US8071632B2 (en) 2008-04-18 2011-12-06 Reata Pharmaceuticals, Inc. Antioxidant inflammation modulators: novel derivatives of oleanolic acid
ES2449396T3 (es) 2008-07-22 2014-03-19 Trustees Of Dartmouth College Cianoenonas monocíclicas y métodos de uso de las mismas
US20110293653A1 (en) * 2010-03-11 2011-12-01 University Of Massachusetts Antagonists of mir-155 for the treatment of inflammatory liver disease
AU2011240690C1 (en) 2010-04-12 2014-11-06 Reata Pharmaceuticals Holdings, LLC Method of treating obesity using antioxidant inflammation modulators
CN103180288B (zh) * 2010-10-27 2015-03-25 希格马托制药工业公司 具有生物学特性的二萜类衍生物
EP2648706A4 (en) 2010-12-06 2014-07-23 Penn State Res Found COMPOSITIONS AND METHODS RELATING TO PROLIFERATIVE DISEASES
ES2653717T3 (es) 2010-12-17 2018-02-08 Reata Pharmaceuticals, Inc. Pirazolil- y pirimidinil-enonas tricíclicas como moduladores antioxidantes de la inflamación
EA026847B1 (ru) 2011-03-11 2017-05-31 Рита Фармасьютикалз, Инк. C4-монометилтритерпеноидные производные и способы их применения
EP2841445B1 (en) 2012-04-27 2017-06-14 Reata Pharmaceuticals, Inc. 2.2-difluoropropionamide derivatives of bardoxolone methyl, polymorphic forms and methods of use thereof
US8921419B2 (en) 2012-05-08 2014-12-30 Trustees Of Dartmouth College Triterpenoids and compositions containing the same
US9556222B2 (en) 2012-06-15 2017-01-31 Reata Pharmaceuticals, Inc. A-ring epoxidized triterpenoid-based anti-inflammation modulators and methods of use thereof
US9512094B2 (en) 2012-09-10 2016-12-06 Reata Pharmaceuticals, Inc. C17-heteroaryl derivatives of oleanolic acid and methods of use thereof
TWI630212B (zh) 2012-09-10 2018-07-21 瑞塔醫藥有限責任公司 丁香油素(oleanolic acid)之c17-烷二基與烯二基衍生物及其使用方法
US9278912B2 (en) 2012-09-10 2016-03-08 Reata Pharmaceuticals, Inc. C13-hydroxy derivatives of oleanolic acid and methods of use thereof
BR112018005861B1 (pt) 2015-09-23 2022-11-22 Reata Pharmaceuticals, Inc Compostos derivados de ácido oleanólico modificado com c4 para a inibição de il-17, composição farmacêutica e usos terapêuticos dos ditos compostos
BR112019009256A2 (pt) 2016-11-08 2019-07-16 Reata Pharmaceuticals, Inc. métodos para tratar síndrome de alport usando bardoxolona metil ou análogos do mesmo
CN106928095A (zh) * 2017-03-14 2017-07-07 华东师范大学 氰基烯酮类三环二萜类似物及其制备方法和应用
US10463631B2 (en) * 2017-06-12 2019-11-05 University Of South Carolina Pimarane diterpenoids for use in wound healing and angiogenesis
US12060340B2 (en) 2018-06-20 2024-08-13 Reata Pharmaceuticals, Inc Cysteine-dependent inverse agonists of nuclear receptors ROR-gamma/ROR-gamma-t and methods of treating diseases or disorders therewith
CN120248001A (zh) 2019-07-19 2025-07-04 里亚塔医药公司 C17极性的-取代的杂芳族合成三萜类化合物及其使用方法

Family Cites Families (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5212708B2 (enExample) 1974-05-14 1977-04-08
JPS522910B2 (enExample) 1974-05-17 1977-01-25
GB1452053A (en) 1974-08-28 1976-10-06 Nippon Shinyaku Co Ltd Abietamide derivatives and a method for the preparation thereof
US4874891A (en) 1986-05-01 1989-10-17 Washington University Open "D" ring hormone analogs
US5133974A (en) 1989-05-05 1992-07-28 Kv Pharmaceutical Company Extended release pharmaceutical formulations
WO1991013855A1 (en) 1990-03-06 1991-09-19 Otsuka Pharmaceutical Co., Ltd. Phenanthrene derivative
US5276182A (en) 1990-07-09 1994-01-04 The Dow Chemical Company Process for preparing polyurea oligomers
DE4039602A1 (de) 1990-12-12 1992-06-17 Bauer Kurt Heinz Prof Dr Pharmazeutische formulierungen
KR100221695B1 (ko) 1991-08-12 1999-09-15 그린 마틴, 브라이언 쥐 테슬리 약학적 구상 제형
US5653962A (en) 1991-12-12 1997-08-05 Glaxo Group Limited Aerosol formulations containing P134a and particulate medicaments
CA2149150C (en) 1992-11-27 2000-08-01 David R. Carver Injectable taxol composition with improved stability
US5654286A (en) 1993-05-12 1997-08-05 Hostetler; Karl Y. Nucleotides for topical treatment of psoriasis, and methods for using same
PL177323B1 (pl) 1993-10-01 1999-10-29 Syntex Inc Kompozycja farmaceutyczna zawierająca mykofenolan mofetylu lub kwas mykofenolowy i sposób wytwarzania kompozycji farmaceutycznej zawierającej mykofenolan mofetylu lub kwas mykofenolowy
KR0145941B1 (ko) * 1994-06-13 1998-08-17 김은영 인터루킨-1과 종양 괴사 인자-알파의 생산 억제에 유용한 아칸토산을 포함하는 약학적 조성물
US5707641A (en) 1994-10-13 1998-01-13 Pharmaderm Research & Development Ltd. Formulations comprising therapeutically-active proteins or polypeptides
IE80468B1 (en) 1995-04-04 1998-07-29 Elan Corp Plc Controlled release biodegradable nanoparticles containing insulin
US5653987A (en) 1995-05-16 1997-08-05 Modi; Pankaj Liquid formulations for proteinic pharmaceuticals
US5726181A (en) 1995-06-05 1998-03-10 Bionumerik Pharmaceuticals, Inc. Formulations and compositions of poorly water soluble camptothecin derivatives
US5667809A (en) 1995-06-07 1997-09-16 Alliance Pharmaceutical Corp. Continuous fluorochemical microdispersions for the delivery of lipophilic pharmaceutical agents
FR2741262B1 (fr) 1995-11-20 1999-03-05 Oreal Utilisation d'un antagoniste de tnf-alpha pour le traitement des rougeurs cutanees d'origine neurogene
ES2211030T3 (es) * 1998-01-26 2004-07-01 Sae Han Pharm. Co., Ltd. Derivados diterpenos y agentes analgesicos anti-inflamatorios que comprenden a los mismos.
US6051590A (en) 1999-05-13 2000-04-18 Merck & Co., Inc. Immunosuppressant tricyclic compounds
PT1178952E (pt) 1999-05-14 2007-12-04 Univ California Novos moduladores da interleucina-1 e do factor alfa de necrose tumoral, síntese dos referidos moduladores e métodos de utilização dos referidos moduladores
WO2002079137A1 (en) 2001-03-28 2002-10-10 Nereus Pharmaceuticals, Inc. Interleukin-1 and tumor necrosis factor-alpha modulators and their enantiomers, their synthesis and use

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Publication number Publication date
NZ515675A (en) 2004-06-25
US20030040640A1 (en) 2003-02-27
AU5013300A (en) 2000-12-18
NZ540001A (en) 2007-06-29
AU2006200240A1 (en) 2006-02-16
JP2012211162A (ja) 2012-11-01
EP1591437B1 (en) 2009-11-25
CA2372962A1 (en) 2000-12-07
JP2003500464A (ja) 2003-01-07
EP1591437A2 (en) 2005-11-02
AU2006200240B2 (en) 2009-05-28
US6881857B2 (en) 2005-04-19
DK1178952T5 (da) 2008-03-17
US20050209325A1 (en) 2005-09-22
WO2000073253A1 (en) 2000-12-07
PT1178952E (pt) 2007-12-04
EP1591437A3 (en) 2006-03-08
NZ529505A (en) 2005-09-30
CN1361760A (zh) 2002-07-31
MXPA01011613A (es) 2003-10-14
EP1178952B1 (en) 2007-08-22
KR100840925B1 (ko) 2008-06-24
JP5059996B2 (ja) 2012-10-31
ATE370928T1 (de) 2007-09-15
IL146221A0 (en) 2002-07-25
EP1178952A1 (en) 2002-02-13
US6365768B1 (en) 2002-04-02
US7342125B2 (en) 2008-03-11
ES2337264T3 (es) 2010-04-22
KR100856353B1 (ko) 2008-09-04
PT1591437E (pt) 2010-03-04
KR20060110013A (ko) 2006-10-23
AU783372B2 (en) 2005-10-20
KR20060135080A (ko) 2006-12-28
DK1178952T3 (da) 2008-01-28
IL146221A (en) 2007-07-04
ATE449754T1 (de) 2009-12-15
ES2295031T3 (es) 2008-04-16
BR0011522A (pt) 2002-06-04
DE60036101D1 (de) 2007-10-04
HK1084657A1 (en) 2006-08-04
KR20020028878A (ko) 2002-04-17
IL182272A0 (en) 2007-07-24
DE60043400D1 (de) 2010-01-07
DE60036101T2 (de) 2008-05-15
IL182272A (en) 2010-05-31

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