WO1998056771A2 - Piperazine derivatives and their use as anti-inflammatory agents - Google Patents

Piperazine derivatives and their use as anti-inflammatory agents Download PDF

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Publication number
WO1998056771A2
WO1998056771A2 PCT/EP1998/003503 EP9803503W WO9856771A2 WO 1998056771 A2 WO1998056771 A2 WO 1998056771A2 EP 9803503 W EP9803503 W EP 9803503W WO 9856771 A2 WO9856771 A2 WO 9856771A2
Authority
WO
WIPO (PCT)
Prior art keywords
alkyl
methyl
carbonyl
glycιnamιdo
fluorobenzyl
Prior art date
Application number
PCT/EP1998/003503
Other languages
English (en)
French (fr)
Other versions
WO1998056771A3 (en
Inventor
John G. Bauman
Brad O. Buckman
Ameen F. Ghannam
Joseph E. Hesselgesser
Richard Horuk
Imadul Islam
Meina Liang
Karen B. May
Sean D. Monahan
Michael M. Morissey
Howard P. Ng
Guo Ping Wei
Wei Xu
Wei Zheng
Original Assignee
Schering Aktiengesellschaft
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
Priority to KR1019997011718A priority Critical patent/KR100549137B1/ko
Priority to SK1713-99A priority patent/SK285162B6/sk
Application filed by Schering Aktiengesellschaft filed Critical Schering Aktiengesellschaft
Priority to JP50161199A priority patent/JP2002503239A/ja
Priority to AU86258/98A priority patent/AU735462B2/en
Priority to CA002293382A priority patent/CA2293382C/en
Priority to EEP200200683A priority patent/EE200200683A/xx
Priority to AT98937467T priority patent/ATE232522T1/de
Priority to DE69811363T priority patent/DE69811363T2/de
Priority to EEP200200682A priority patent/EE200200682A/xx
Priority to IL13239898A priority patent/IL132398A/en
Priority to EP98937467A priority patent/EP0988292B1/en
Priority to EA199901063A priority patent/EA004038B1/ru
Priority to HU0003929A priority patent/HUP0003929A3/hu
Priority to EEP199900565A priority patent/EE04056B1/xx
Priority to DK98937467T priority patent/DK0988292T3/da
Priority to SK79-2005A priority patent/SK285445B6/sk
Priority to EEP200200684A priority patent/EE200200684A/xx
Publication of WO1998056771A2 publication Critical patent/WO1998056771A2/en
Publication of WO1998056771A3 publication Critical patent/WO1998056771A3/en
Priority to IS5258A priority patent/IS2241B/is
Priority to NO19996068A priority patent/NO317343B1/no
Priority to NO20031373A priority patent/NO20031373D0/no

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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
    • C07D295/16—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
    • C07D295/18—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 carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • 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
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/18—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/04—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
    • C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
    • C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D261/14—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
    • C07D295/18—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 carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/192—Radicals derived from carboxylic acids from aromatic carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
PCT/EP1998/003503 1997-06-12 1998-06-11 Piperazine derivatives and their use as anti-inflammatory agents WO1998056771A2 (en)

Priority Applications (20)

Application Number Priority Date Filing Date Title
SK79-2005A SK285445B6 (sk) 1997-06-12 1998-06-11 Piperazínové deriváty, farmaceutické prostriedky obsahujúce tieto zlúčeniny a ich použitie ako protizápalových činidiel
IL13239898A IL132398A (en) 1997-06-12 1998-06-11 History of piparazine and pharmaceutical preparations containing them
JP50161199A JP2002503239A (ja) 1997-06-12 1998-06-11 ピペラジン誘導体及び抗炎症剤としてのそれらの使用
AU86258/98A AU735462B2 (en) 1997-06-12 1998-06-11 Piperazine derivatives and their use as anti-inflammatory agents
CA002293382A CA2293382C (en) 1997-06-12 1998-06-11 Piperazine derivatives and their use as anti-inflammatory agents
EEP200200683A EE200200683A (et) 1997-06-12 1998-06-11 Piperasiini derivaadid ja nende kasutamine põletikuvastaste vahenditena
AT98937467T ATE232522T1 (de) 1997-06-12 1998-06-11 Piperazin-derivate und ihre verwendung als entzündungshemmende mittel
DE69811363T DE69811363T2 (de) 1997-06-12 1998-06-11 Piperazin-derivate und ihre verwendung als entzündungshemmende mittel
EA199901063A EA004038B1 (ru) 1997-06-12 1998-06-11 Пиперазиновые производные и их применение в качестве противовоспалительных агентов
KR1019997011718A KR100549137B1 (ko) 1997-06-12 1998-06-11 피페라진 유도체 및 소염제로서의 그의 용도
EP98937467A EP0988292B1 (en) 1997-06-12 1998-06-11 Piperazine derivatives and their use as anti-inflammatory agents
EEP200200682A EE200200682A (et) 1997-06-12 1998-06-11 Piperasiini derivaadid ja nende kasutamine põletikuvastaste vahenditena
HU0003929A HUP0003929A3 (en) 1997-06-12 1998-06-11 Piperazine derivatives and their use for producing pharmaceutical compositions as anti-inflammatory agents and pharmaceutical compositions containing them
EEP199900565A EE04056B1 (et) 1997-06-12 1998-06-11 Piperasiini derivaadid ja nende kasutamine põletikuvastaste vahenditena
DK98937467T DK0988292T3 (da) 1997-06-12 1998-06-11 Piperazinderivater og deres anvendelse som antiinflammationsmidler
SK1713-99A SK285162B6 (sk) 1997-06-12 1998-06-11 Piperazínové deriváty, farmaceutické prostriedky obsahujúce tieto zlúčeniny a ich použitie ako protizápalových činidiel
EEP200200684A EE200200684A (et) 1997-06-12 1998-06-11 Piperasiini derivaadid ja nende kasutamine põletikuvastaste vahenditena
IS5258A IS2241B (is) 1997-06-12 1999-11-19 Píperasín afleiður og notkun þeirra sem bólgueyðandi miðlar
NO19996068A NO317343B1 (no) 1997-06-12 1999-12-09 Piperazinderivater og deres anvendelse som anti-inflammatoriske midler
NO20031373A NO20031373D0 (no) 1997-06-12 2003-03-26 Piperazinderivater og deres anvendelse som antiinflammatoriske midler

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US87359997A 1997-06-12 1997-06-12
US08/873,599 1997-06-12
US09/094,397 US6207665B1 (en) 1997-06-12 1998-06-09 Piperazine derivatives and their use as anti-inflammatory agents
US09/094,397 1998-06-09

Publications (2)

Publication Number Publication Date
WO1998056771A2 true WO1998056771A2 (en) 1998-12-17
WO1998056771A3 WO1998056771A3 (en) 1999-03-11

Family

ID=26788818

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1998/003503 WO1998056771A2 (en) 1997-06-12 1998-06-11 Piperazine derivatives and their use as anti-inflammatory agents

Country Status (22)

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US (8) US6207665B1 (US20030139425A1-20030724-C00009.png)
EP (2) EP1254899B1 (US20030139425A1-20030724-C00009.png)
JP (1) JP2002503239A (US20030139425A1-20030724-C00009.png)
KR (1) KR100549137B1 (US20030139425A1-20030724-C00009.png)
AT (2) ATE296292T1 (US20030139425A1-20030724-C00009.png)
AU (1) AU735462B2 (US20030139425A1-20030724-C00009.png)
CA (1) CA2293382C (US20030139425A1-20030724-C00009.png)
CZ (1) CZ295784B6 (US20030139425A1-20030724-C00009.png)
DE (2) DE69811363T2 (US20030139425A1-20030724-C00009.png)
DK (2) DK0988292T3 (US20030139425A1-20030724-C00009.png)
EA (2) EA200200262A1 (US20030139425A1-20030724-C00009.png)
EE (4) EE04056B1 (US20030139425A1-20030724-C00009.png)
ES (2) ES2191320T3 (US20030139425A1-20030724-C00009.png)
HU (1) HUP0003929A3 (US20030139425A1-20030724-C00009.png)
IL (1) IL132398A (US20030139425A1-20030724-C00009.png)
IS (1) IS2241B (US20030139425A1-20030724-C00009.png)
NO (2) NO317343B1 (US20030139425A1-20030724-C00009.png)
PL (1) PL337758A1 (US20030139425A1-20030724-C00009.png)
PT (1) PT1254899E (US20030139425A1-20030724-C00009.png)
SK (2) SK285162B6 (US20030139425A1-20030724-C00009.png)
TR (1) TR199903034T2 (US20030139425A1-20030724-C00009.png)
WO (1) WO1998056771A2 (US20030139425A1-20030724-C00009.png)

Cited By (52)

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WO2000044408A2 (en) * 1999-01-29 2000-08-03 Millennium Pharmaceuticals, Inc. Method of treating demyelinating inflammatory disease using ccr1 antagonists
WO2001072728A2 (en) * 2000-03-31 2001-10-04 Pfizer Products Inc. Novel piperazine derivatives
WO2002032901A2 (en) * 2000-10-19 2002-04-25 Pfizer Products Inc. Bridged piperazine derivatives
WO2002036581A1 (en) * 2000-11-06 2002-05-10 Schering Aktiengesellschaft Radiopharmaceuticals for diagnosing alzheimer's disease
WO2002098856A2 (en) * 2001-06-06 2002-12-12 Schering Aktiengesellschaft Piperazine oxyquinoline (naphthaline) platelet adenosine diphosphate receptor antagonists
WO2002102787A2 (en) * 2001-06-20 2002-12-27 Pfizer Products Inc. Novel sulfonic acid derivatives
WO2003035037A1 (de) * 2001-10-18 2003-05-01 Schering Aktiengesellschaft Feste arzneimittelformulierung für ein piperazinharnstoffderivat
WO2003082834A2 (en) * 2002-03-28 2003-10-09 Glaxo Group Limited Morpholine derivatives and intermediates therefor
US6727241B2 (en) 2002-06-12 2004-04-27 Chemocentryx Anti-inflammatory compositions and methods of use
LT5132B (lt) 2000-07-31 2004-05-25 Schering Aktiengesellschaft Nepeptidiniai ccr1 receptorių antagonistai derinyje su ciklosporinu a širdies transplanto atmetimui gydyti
WO2004055031A1 (en) * 2002-12-13 2004-07-01 Pfizer Products Inc. Phosphorus-containing piperazine derivatives as ccr1 antagonists
US6812230B2 (en) * 2001-08-07 2004-11-02 Schering Aktiengesellschaft Non-peptide CCR1 receptor antagonists for the treatment of progressive renal fibrosis
KR100472086B1 (ko) * 2001-11-23 2005-02-21 한국화학연구원 항산화 활성을 갖는 3,5-디알콕시-4-히드록시페닐기로치환된 피페라진 유도체, 그의 제조방법 및 이를 포함하는약학적 조성물
WO2005080362A1 (en) * 2004-02-25 2005-09-01 Active Biotech Ab Cinnamic amides, process for their preparation, and pharmaceutical compositions containing them
WO2005103054A2 (en) * 2004-04-26 2005-11-03 Novartis Ag Bridged piperazine and piperidine derivatives as ccri antagonists
WO2006031922A2 (en) 2004-09-15 2006-03-23 Ordway Research Institute Thyroid hormone analogs for promoting angiogenesis
US7056923B2 (en) 2002-12-11 2006-06-06 Schering Aktiengesellschaft Platelet adenosine diphosphate receptor antagonists
US7098212B2 (en) 2001-10-22 2006-08-29 Blumberg Laura C Piperazine derivatives
US7157464B2 (en) 2002-06-12 2007-01-02 Chemocentryx, Inc. Substituted piperazines
EP1749519A1 (de) 2005-08-05 2007-02-07 Schering Aktiengesellschaft Arzneiform mit Retardtierter pH-unabhängiger Wirkstofffreisetzung für Wirkstoffe mit starker pH-abhängiger Löslichkeit
US7253172B2 (en) * 2001-06-20 2007-08-07 Merck & Co., Inc. Dipeptidyl peptidase inhibitors for the treatment of diabetes
US7339059B2 (en) 2004-02-25 2008-03-04 Active Biotech Ab Benzofurans and indols
US7435831B2 (en) 2004-03-03 2008-10-14 Chemocentryx, Inc. Bicyclic and bridged nitrogen heterocycles
US7435830B2 (en) 2004-03-03 2008-10-14 Chemocentryx, Inc. Bicyclic and bridged nitrogen heterocycles
US7589199B2 (en) 2002-06-12 2009-09-15 Chemocentryx, Inc. Substituted piperazines
US7622464B2 (en) 2002-03-28 2009-11-24 Glaxo Group Limited Morpholinyl-urea derivatives for use in the treatment of inflammatory diseases
US7785632B2 (en) 2003-09-15 2010-08-31 Ordway Research Institute, Inc. Thyroid hormone analogs and methods of use
US7842693B2 (en) 2002-06-12 2010-11-30 Chemocentryx, Inc. Substituted piperazines
US8044052B2 (en) 2006-10-18 2011-10-25 Pfizer Inc. Biaryl ether urea compounds
US8071134B2 (en) 2003-09-15 2011-12-06 Ordway Research Institute, Inc. Thyroid hormone analogs and methods of use
WO2013060865A1 (en) 2011-10-28 2013-05-02 Galderma Research & Development New leukocyte infiltrate markers for rosacea and uses thereof
US8668926B1 (en) 2003-09-15 2014-03-11 Shaker A. Mousa Nanoparticle and polymer formulations for thyroid hormone analogs, antagonists, and formulations thereof
CN103724296A (zh) * 2013-12-12 2014-04-16 南京医科大学 芳基取代的哌嗪羰基衍生物及其制备方法和应用
US8802240B2 (en) 2011-01-06 2014-08-12 Nanopharmaceuticals Llc Uses of formulations of thyroid hormone analogs and nanoparticulate forms thereof to increase chemosensitivity and radiosensitivity in tumor or cancer cells
WO2015008230A1 (en) 2013-07-18 2015-01-22 Novartis Ag Autotaxin inhibitors comprising a heteroaromatic ring-benzyl-amide-cycle core
US9180107B2 (en) 2009-03-31 2015-11-10 Nanopharmaceuticals Llc Combination treatment of cancer with cetuximab and tetrac
US9198887B2 (en) 2003-09-15 2015-12-01 Nanopharmaceuticals Llc Thyroid hormone analogs and methods of use
US9220788B2 (en) 2009-06-17 2015-12-29 Nanopharmaceuticals Llc Nanoparticle and polymer formulations for thyroid hormone analogs, antagonists, and formulations and uses thereof
US9272049B2 (en) 2005-09-16 2016-03-01 Nanopharmaceuticals Llc Methods of stimulating fat mobilization using a polymer conjugated polyphenol
US9289395B2 (en) 2006-12-22 2016-03-22 Nanopharmaceuticals Llc Nanoparticle and polymer formulations for thyroid hormone analogs, antagonists, and formulations and uses thereof
US9498536B2 (en) 2005-09-15 2016-11-22 Nanopharmaceuticals Llc Method and composition of thyroid hormone analogues and nanoformulations thereof for treating anti-inflammatory disorders
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US10130686B2 (en) 2005-09-15 2018-11-20 Nanopharmaceuticals Llc Method and composition of thyroid hormone analogues and nanoformulations thereof for treating inflammatory disorders
US10201616B2 (en) 2016-06-07 2019-02-12 Nanopharmaceuticals, Llc Non-cleavable polymer conjugated with αVβ3 integrin thyroid antagonists
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US7268140B2 (en) 2007-09-11
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SK285445B6 (sk) 2007-01-04
DE69830341D1 (de) 2005-06-30
ATE232522T1 (de) 2003-02-15
ATE296292T1 (de) 2005-06-15
US6555537B2 (en) 2003-04-29
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