CN101010312B - 化学趋化细胞因子受体2季盐拮抗剂 - Google Patents

化学趋化细胞因子受体2季盐拮抗剂 Download PDF

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CN101010312B
CN101010312B CN2005800286402A CN200580028640A CN101010312B CN 101010312 B CN101010312 B CN 101010312B CN 2005800286402 A CN2005800286402 A CN 2005800286402A CN 200580028640 A CN200580028640 A CN 200580028640A CN 101010312 B CN101010312 B CN 101010312B
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compound
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aryl
benzyl
phenyl
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CN101010312A (zh
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B·拉古
M·P·沃奇特
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Janssen Pharmaceutica NV
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Families Citing this family (48)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7799824B2 (en) 2004-06-25 2010-09-21 Orapharma, Inc. Quaternary salt CCR2 antagonists
JP2010513245A (ja) * 2006-12-14 2010-04-30 アクトジェニックス・エヌブイ 免疫調節を誘起するための結合分子の送達
WO2008131481A1 (en) * 2007-04-26 2008-11-06 Fibrotech Therapeutics Pty Ltd Treatment of mesangioproliferative diseases
WO2008145681A2 (en) 2007-05-31 2008-12-04 Boehringer Ingelheim International Gmbh Ccr2 receptor antagonists and uses thereof
AU2008299386B2 (en) 2007-09-14 2012-01-12 Barrick Gold Corporation Process for recovering platinum group metals using reductants
US8168829B2 (en) * 2007-10-26 2012-05-01 Janssen Pharmaceutica N.V. Synthesis of quaternary salt compounds
US8093428B2 (en) * 2007-10-26 2012-01-10 Janssen Pharmaceutica N.V. Synthesis of quaternary salt compounds
TW200927740A (en) * 2007-11-13 2009-07-01 Bial Portela & Ca Sa Process
KR100954138B1 (ko) * 2007-12-31 2010-04-20 부산대학교 산학협력단 지방조직 유래 줄기세포를 함유하는 알레르기 비염 또는천식 예방 및 치료제
CN101481323B (zh) * 2008-01-11 2013-11-20 中国人民解放军军事医学科学院毒物药物研究所 苯并环庚烯类衍生物、其制备方法及医药用途
CN102256963B (zh) 2008-12-19 2014-06-11 贝林格尔.英格海姆国际有限公司 作为ccr2受体拮抗剂用于治疗炎症、哮喘和copd的环状嘧啶-4-甲酰胺
EP2491030B1 (en) * 2009-10-22 2015-07-15 Fibrotech Therapeutics PTY LTD Fused ring analogues of anti-fibrotic agents
PT2513093E (pt) 2009-12-17 2014-10-22 Boehringer Ingelheim Int Novos antagonistas do receptor ccr2 e suas utilizações
US8946218B2 (en) 2010-05-12 2015-02-03 Boehringer Ingelheim International Gmbh CCR2 receptor antagonists, method for producing the same, and use thereof as medicaments
EP2569298B1 (en) 2010-05-12 2015-11-25 Boehringer Ingelheim International GmbH Novel ccr2 receptor antagonists, method for producing the same, and use thereof as medicaments
JP5647339B2 (ja) 2010-05-17 2014-12-24 ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング Ｃｃｒ２アンタゴニスト及びこれらの使用
JP5636094B2 (ja) 2010-05-25 2014-12-03 ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング Ｃｃｒ２受容体アンタゴニスト
US8962656B2 (en) 2010-06-01 2015-02-24 Boehringer Ingelheim International Gmbh CCR2 antagonists
WO2011156321A1 (en) 2010-06-07 2011-12-15 Novomedix, Llc Furanyl compounds and the use thereof
BR112012033657A2 (pt) * 2010-06-30 2016-11-29 Johnson & Johnson Vision Care dispositivos oftálmicos que contêm antagonistas de quimioquina
JP5722892B2 (ja) * 2010-07-15 2015-05-27 武田薬品工業株式会社 複素環化合物
US10451897B2 (en) 2011-03-18 2019-10-22 Johnson & Johnson Vision Care, Inc. Components with multiple energization elements for biomedical devices
WO2013009582A1 (en) * 2011-07-12 2013-01-17 Merck Sharp & Dohme Corp. TrkA KINASE INHIBITORS, COMPOSITIONS AND METHODS THEREOF
JP5786258B2 (ja) 2011-07-15 2015-09-30 ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング 新規かつ選択的なｃｃｒ２拮抗薬
US9812730B2 (en) 2011-08-02 2017-11-07 Johnson & Johnson Vision Care, Inc. Biocompatible wire battery
EP2771484A1 (en) 2011-10-28 2014-09-03 Galderma Research & Development New leukocyte infiltrate markers for rosacea and uses thereof
US8857983B2 (en) 2012-01-26 2014-10-14 Johnson & Johnson Vision Care, Inc. Ophthalmic lens assembly having an integrated antenna structure
DK2844250T3 (en) 2012-05-01 2018-01-08 Translatum Medicus Inc METHODS OF TREATMENT AND DIAGNOSTICATION OF EYE DISEASES CONCERNING BLINDNESS
US10627651B2 (en) 2014-08-21 2020-04-21 Johnson & Johnson Vision Care, Inc. Methods and apparatus to form biocompatible energization primary elements for biomedical devices with electroless sealing layers
US9941547B2 (en) 2014-08-21 2018-04-10 Johnson & Johnson Vision Care, Inc. Biomedical energization elements with polymer electrolytes and cavity structures
US9793536B2 (en) 2014-08-21 2017-10-17 Johnson & Johnson Vision Care, Inc. Pellet form cathode for use in a biocompatible battery
US9599842B2 (en) 2014-08-21 2017-03-21 Johnson & Johnson Vision Care, Inc. Device and methods for sealing and encapsulation for biocompatible energization elements
US9383593B2 (en) 2014-08-21 2016-07-05 Johnson & Johnson Vision Care, Inc. Methods to form biocompatible energization elements for biomedical devices comprising laminates and placed separators
US10361405B2 (en) 2014-08-21 2019-07-23 Johnson & Johnson Vision Care, Inc. Biomedical energization elements with polymer electrolytes
US9715130B2 (en) 2014-08-21 2017-07-25 Johnson & Johnson Vision Care, Inc. Methods and apparatus to form separators for biocompatible energization elements for biomedical devices
US10381687B2 (en) 2014-08-21 2019-08-13 Johnson & Johnson Vision Care, Inc. Methods of forming biocompatible rechargable energization elements for biomedical devices
US10361404B2 (en) 2014-08-21 2019-07-23 Johnson & Johnson Vision Care, Inc. Anodes for use in biocompatible energization elements
AU2016287584B2 (en) 2015-07-02 2020-03-26 Centrexion Therapeutics Corporation (4-((3R,4R)-3-methoxytetrahydro-pyran-4-ylamino)piperidin-1-yl)(5-methyl-6-(((2R,6S)-6-(p-tolyl)tetrahydro-2H-pyran-2-yl)methylamino)pyrimidin-4yl)methanone citrate
UY37124A (es) 2016-02-15 2017-09-29 Sanofi Sa Nuevos compuestos de 6,7-dihidro-5h-benzo[7]anuleno sustituidos, procesos para su preparación y usos terapéuticos de los mismos
US10345620B2 (en) 2016-02-18 2019-07-09 Johnson & Johnson Vision Care, Inc. Methods and apparatus to form biocompatible energization elements incorporating fuel cells for biomedical devices
RU2742278C2 (ru) 2016-11-17 2021-02-04 Санофи Новые соединения замещенного n-(3-фторпропил)пирролидина, способы их получения и их терапевтическое применение
CA3052036A1 (en) 2017-02-03 2018-08-09 Certa Therapeutics Pty Ltd. Anti-fibrotic compounds
EP3434272A1 (en) 2017-07-25 2019-01-30 Sanofi Combination comprising palbociclib and 6-(2,4-dichlorophenyl)-5-[4-[(3s)-1-(3-fluoropropyl)pyrrolidin-3-yl]oxyphenyl]-8,9-dihydro-7h-benzo[7]annulene-2-carboxylic acid
KR20210009315A (ko) 2018-04-11 2021-01-26 오하이오 스테이트 이노베이션 파운데이션 안약 전달용 서방형 마이크로 입자를 이용한 방법 및 조성물
EP3833762A4 (en) 2018-08-09 2022-09-28 Verseau Therapeutics, Inc. Oligonucleotide compositions for targeting ccr2 and csf1r and uses thereof
TW202026280A (zh) 2018-09-07 2020-07-16 法商賽諾菲公司 6-(2,4-二氯苯基)-5-[4-[(3s)-1-(3-氟丙基)吡咯啶-3-基]氧基苯基]-8,9-二氫-7h-苯並[7]輪烯-2-甲酸甲酯的鹽及其製備方法
TW202146007A (zh) 2020-02-27 2021-12-16 法商賽諾菲公司 包含阿培利司（ａｌｐｅｌｉｓｉｂ）與６－（２，４－二氯苯基）－５－［４－［（３ｓ）－１－（３－氟丙基）吡咯啶－３－基］氧苯基］－８，９－二氫－７ｈ－苯并［７］輪烯－２－羧酸之組合
CN111808062B (zh) * 2020-07-28 2022-09-13 遵义医科大学 一种蛇床子素磺酸酯类化合物及其应用

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000010965A2 (en) * 1998-08-20 2000-03-02 Takeda Chemical Industries, Ltd. Quaternary ammonium salts and their use as anti-hiv agents
WO2000037455A1 (en) * 1998-12-21 2000-06-29 Takeda Chemical Industries, Ltd. Benzothiepin-anilide derivatives, their production and their use for antagonizing ccr-5
CN1282326A (zh) * 1997-12-19 2001-01-31 武田药品工业株式会社 酰苯胺衍生物、其生产方法及其用途

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0873476A (ja) * 1994-07-04 1996-03-19 Takeda Chem Ind Ltd ホスホン酸誘導体およびそれを含んでなる医薬
JP4416198B2 (ja) * 1997-12-19 2010-02-17 武田薬品工業株式会社 アニリド誘導体、その製造法および用途
WO1999032100A2 (en) * 1997-12-19 1999-07-01 Takeda Chemical Industries, Ltd. Pharmaceutical composition for antagonizing ccr5 comprising anilide derivative
JP2001058988A (ja) * 1998-12-21 2001-03-06 Takeda Chem Ind Ltd アニリド誘導体、その製造法および用途
EP1182195A4 (en) * 1999-05-07 2003-03-26 Takeda Chemical Industries Ltd CYCLIC CONNECTIONS AND APPLICATIONS THEREOF
JP2001026586A (ja) * 1999-05-07 2001-01-30 Takeda Chem Ind Ltd 環状化合物およびその用途
AU1734401A (en) * 1999-12-09 2001-06-18 Mitsubishi Pharma Corporation Carboxyamido derivatives
AU2003235205A1 (en) * 2002-04-19 2003-11-03 Takeda Pharmaceutical Company Limited Preventives for hiv infection
JP2004043432A (ja) * 2002-04-19 2004-02-12 Takeda Chem Ind Ltd Ｈｉｖ感染予防剤
JP4145230B2 (ja) * 2002-11-01 2008-09-03 武田薬品工業株式会社 神経障害の予防・治療剤
US7799824B2 (en) 2004-06-25 2010-09-21 Orapharma, Inc. Quaternary salt CCR2 antagonists
EA200700007A1 (ru) 2004-06-25 2007-08-31 Басф Акциенгезельшафт Триазолопиримидиновые соединения и их применение для борьбы с патогенными грибами

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1282326A (zh) * 1997-12-19 2001-01-31 武田药品工业株式会社 酰苯胺衍生物、其生产方法及其用途
WO2000010965A2 (en) * 1998-08-20 2000-03-02 Takeda Chemical Industries, Ltd. Quaternary ammonium salts and their use as anti-hiv agents
WO2000037455A1 (en) * 1998-12-21 2000-06-29 Takeda Chemical Industries, Ltd. Benzothiepin-anilide derivatives, their production and their use for antagonizing ccr-5

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