TWI407957B - Ｃｃｒ２拮抗劑之四級鹽 - Google Patents

Ｃｃｒ２拮抗劑之四級鹽 Download PDF

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TWI407957B
TWI407957B TW094121070A TW94121070A TWI407957B TW I407957 B TWI407957 B TW I407957B TW 094121070 A TW094121070 A TW 094121070A TW 94121070 A TW94121070 A TW 94121070A TW I407957 B TWI407957 B TW I407957B
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Taiwan
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compound
group
mmol
substituted
phenyl
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TW094121070A
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Chinese (zh)
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TW200612934A (en
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Bharat Lagu
Michael Wachter
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Janssen Pharmaceutica Nv
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    • C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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Families Citing this family (52)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2573845T3 (es) 2004-06-25 2016-06-10 Janssen Pharmaceutica Nv Antagonistas de CCR2 de sales cuaternarias
CA2672229A1 (en) * 2006-12-14 2008-06-19 Actogenix N.V. Delivery of binding molecules to induce immunomodulation
WO2008131481A1 (en) * 2007-04-26 2008-11-06 Fibrotech Therapeutics Pty Ltd Treatment of mesangioproliferative diseases
CA2687931C (en) 2007-05-31 2016-05-24 Boehringer Ingelheim International Gmbh Ccr2 receptor antagonists and uses thereof
RU2010114611A (ru) 2007-09-14 2011-10-20 Баррик Гольд Корпорейшн (CA) Способ восстановления металлов платиновой группы с использованием восстановителей
US8093428B2 (en) * 2007-10-26 2012-01-10 Janssen Pharmaceutica N.V. Synthesis of quaternary salt compounds
US8168829B2 (en) * 2007-10-26 2012-05-01 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
ES2551557T3 (es) 2008-12-19 2015-11-19 Boehringer Ingelheim International Gmbh Pirimidin-4-carboxamidas cíclicas como antagonistas del receptor CCR2 para el tratamiento de inflamaciones, asma y EPOC
EP2947073B1 (en) 2009-10-22 2019-04-03 Fibrotech Therapeutics Pty Ltd Fused ring analogues of anti-fibrotic agents
PL2513093T3 (pl) 2009-12-17 2015-03-31 Centrexion Therapeutics Corp Nowi antagoniści receptora CCR2 i ich zastosowanie
EP2569295B1 (en) 2010-05-12 2014-11-19 Boehringer Ingelheim International GmbH New ccr2 receptor antagonists, method for producing the same, and use thereof as medicaments
WO2011141474A1 (en) 2010-05-12 2011-11-17 Boehringer Ingelheim International Gmbh Novel ccr2 receptor antagonists, method for producing the same, and use thereof as medicaments
EP2571870B1 (en) 2010-05-17 2015-01-21 Boehringer Ingelheim International GmbH Ccr2 antagonists and uses thereof
US9018212B2 (en) 2010-05-25 2015-04-28 Boehringer Ingelheim International Gmbh Pyridazine carboxamides as CCR2 receptor antagonists
JP5721242B2 (ja) 2010-06-01 2015-05-20 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ｃｃｒ２アンタゴニスト
EP2576532B1 (en) 2010-06-07 2018-07-18 Novomedix, LLC Furanyl compounds and the use thereof
US20120004298A1 (en) * 2010-06-30 2012-01-05 Hassan Chaouk Ophthalmic devices containing chemokine antagonists
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
US9102673B2 (en) 2011-07-12 2015-08-11 Merck Sharp & Dohme Corp. Substituted pyrrolo[3,2-c]pyridines as TrkA kinase inhibitors
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
CA2852160A1 (en) 2011-10-28 2013-05-02 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
CA3095012C (en) 2012-05-01 2023-02-07 Translatum Medicus Inc. Methods for treating and diagnosing blinding eye diseases
US9793536B2 (en) 2014-08-21 2017-10-17 Johnson & Johnson Vision Care, Inc. Pellet form cathode for use in a biocompatible battery
US10381687B2 (en) 2014-08-21 2019-08-13 Johnson & Johnson Vision Care, Inc. Methods of forming biocompatible rechargable energization elements for biomedical devices
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
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
US9599842B2 (en) 2014-08-21 2017-03-21 Johnson & Johnson Vision Care, Inc. Device and methods for sealing and encapsulation for biocompatible energization elements
US9941547B2 (en) 2014-08-21 2018-04-10 Johnson & Johnson Vision Care, Inc. Biomedical energization elements with polymer electrolytes and cavity structures
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
US10361404B2 (en) 2014-08-21 2019-07-23 Johnson & Johnson Vision Care, Inc. Anodes for use in biocompatible energization elements
US10361405B2 (en) 2014-08-21 2019-07-23 Johnson & Johnson Vision Care, Inc. Biomedical energization elements with polymer electrolytes
MX383744B (es) 2015-07-02 2025-03-14 Centrexion Therapeutics Corp Citrato de (4-((3r,4r)-3-metoxitetrahidro-piran-4-ilamino)piperidin-1-il) (5-metil-6-(((2r, 6s)-6-(p-tolil)tetrahidro-2h-piran-2-il) metilamino) pirimidin-4-il) metanona.
SG11201806829TA (en) * 2016-02-15 2018-09-27 Sanofi Sa 6,7-dihydro-5h-benzo[7]annulene derivatives as estrogen receptor modulators
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
EP3541809B1 (en) 2016-11-17 2025-06-25 Sanofi Novel substituted n-(3-fluoropropyl)-pyrrolidine compounds, processes for their preparation and therapeutic uses thereof
EP3577103A1 (en) 2017-02-03 2019-12-11 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
WO2020033791A1 (en) 2018-08-09 2020-02-13 Verseau Therapeutics, Inc. Oligonucleotide compositions for targeting ccr2 and csf1r and uses thereof
DK3847157T3 (da) 2018-09-07 2022-08-08 Sanofi Sa Fremgangsmåde til fremstilling af methyl-[6-(2,4-dichlorphenyl)-5-[4-[(3s)-1-(3-fluorpropyl)pyrrolidin-3-yl]oxyphenyl]-8,9-dihydro-7h-benzo[7]annulen-2-carboxylat] og salt deraf
WO2021063967A1 (en) 2019-10-01 2021-04-08 Sanofi Novel substituted 6,7-dihydro-5h-benzo[7]annulene compounds, processes for their preparation and therapeutic uses thereof
CA3160897A1 (en) 2019-12-09 2021-06-17 Sanofi Crystalline form of a 7h-benzo[7]annulene-2-carboxylic acid derivative
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
IL302152B1 (en) 2020-10-19 2026-07-01 Sanofi Sa 6,7-DIHYDRO-5H-BENZO[7]ANNULENE COMPOUNDS AND THEIR DERIVATIVES, PROCESSES FOR THEIR PREPARATION AND THEIR THERAPEUTIC USES
IL302153B1 (en) 2020-10-19 2026-07-01 Sanofi Sa 6,7-DIHYDRO-5H-BENZO[7]ANNULENE COMPOUNDS AND THEIR DERIVATIVES, PROCESSES FOR THEIR PREPARATION AND THEIR THERAPEUTIC USES

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999032100A2 (en) * 1997-12-19 1999-07-01 Takeda Chemical Industries, Ltd. Pharmaceutical composition for antagonizing ccr5 comprising anilide derivative
WO2000068203A1 (en) * 1999-05-07 2000-11-16 Takeda Chemical Industries, Ltd. Cyclic compounds and uses thereof
US6166006A (en) * 1997-12-19 2000-12-26 Takeda Chemical Industries, Ltd. Anilide derivative, production and use thereof

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
EP1104416A2 (en) 1998-08-20 2001-06-06 Takeda Chemical Industries, Ltd. Quaternary ammonium salts and their use as anti-hiv agents
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
EP1140896A1 (en) 1998-12-21 2001-10-10 Takeda Chemical Industries, Ltd. Benzothiepin-anilide derivatives, their production and their use for antagonizing ccr-5
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
US20050154016A1 (en) * 2002-04-19 2005-07-14 Katsunori Takashima 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
ES2573845T3 (es) 2004-06-25 2016-06-10 Janssen Pharmaceutica Nv Antagonistas de CCR2 de sales cuaternarias
KR20070024646A (ko) * 2004-06-25 2007-03-02 바스프 악티엔게젤샤프트 트리아졸로피리미딘 화합물 및 그의 병원성 진균류 방제를위한 용도

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999032100A2 (en) * 1997-12-19 1999-07-01 Takeda Chemical Industries, Ltd. Pharmaceutical composition for antagonizing ccr5 comprising anilide derivative
US6166006A (en) * 1997-12-19 2000-12-26 Takeda Chemical Industries, Ltd. Anilide derivative, production and use thereof
WO2000068203A1 (en) * 1999-05-07 2000-11-16 Takeda Chemical Industries, Ltd. Cyclic compounds and uses thereof

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Shiraishi M, Discovery of novel, potent, and selective small-molecule CCR5 antagonists as anti-HIV-1 agents: synthesis and biological evaluation of anilide derivatives with a quaternary ammonium moiety, Journal of Medicinal Chemistry, 43, 2049-2063, 2000 *

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