ES2571409T3 - Antagonistas espiro-cíclicos de TRPV4 - Google Patents

Antagonistas espiro-cíclicos de TRPV4

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Publication number
ES2571409T3
ES2571409T3 ES12800913T ES12800913T ES2571409T3 ES 2571409 T3 ES2571409 T3 ES 2571409T3 ES 12800913 T ES12800913 T ES 12800913T ES 12800913 T ES12800913 T ES 12800913T ES 2571409 T3 ES2571409 T3 ES 2571409T3
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Prior art keywords
phenyl
3alkyl
het
halogen
hydrogen
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ES12800913T
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English (en)
Inventor
Carl Brooks
Mui Cheung
Hilary Eidam
Krista Goodman
Marlys Hammond
Mark Hilfiker
Jaclyn Patterson
Patrick Stoy
Guosen Ye
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GlaxoSmithKline Intellectual Property No 2 Ltd
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GlaxoSmithKline Intellectual Property No 2 Ltd
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    • 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
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/10—Laxatives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/12—Antidiarrhoeals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
    • 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
    • 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
    • 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
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/10—Drugs for disorders of the urinary system of the bladder
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/12—Drugs for disorders of the urinary system of the kidneys
    • 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
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
    • 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
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • 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
    • A61P25/08—Antiepileptics; Anticonvulsants
    • 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
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • 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
    • 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
    • A61P7/10—Antioedematous agents; Diuretics
    • 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
    • A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
    • 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
    • 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
    • A61P9/12—Antihypertensives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • 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
    • C07D413/06—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 carbon chain containing only aliphatic carbon atoms
    • 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
    • C07D413/08—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 carbon chain containing alicyclic rings

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Engineering & Computer Science (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Pulmonology (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Pain & Pain Management (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Urology & Nephrology (AREA)
  • Rheumatology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Hematology (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Psychology (AREA)
  • Vascular Medicine (AREA)
  • Hospice & Palliative Care (AREA)
  • Diabetes (AREA)
  • Otolaryngology (AREA)
  • Nutrition Science (AREA)
  • Immunology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Un compuesto de fórmula (I):**Fórmula** en donde: R1 es hidrógeno, alquilo C1-3, CH2OH, CH2-O-CH3, CH2OCH2Ph, CH2CN, CN, halógeno, o C(O)OCH3; R2 es independientemente hidrógeno, CN, CF3, halógeno, SO2-alquiloC1-3, alquilo C1-3 o C≡CH; R3 es hidrógeno, alquilo C1-2, CF3 o -OH; R4 es hidrógeno, halógeno, o alquilo C1-3; X es CR4 o N; A es (CH2)n-fenilo, (CH2)n-naftilo, (CH2)n-C(O)-fenilo, (CH2)n-dihidroindenilo, (CH2)n-tetrahidronaftalenilo, (CH2)nbenzodioxol, (CH2)n-dihidrobenzodioxinilo, (CH2)n-dihidroindenilo, (CH2)n-dimetildihidrobenzofuranilo, (CH2)noxotetrahidropirrolilfenilo o (CH2)n-tetrahidrofurilfenilo; en donde el fenilo puede estar sustituido con uno o más sustituyentes seleccionados de: halógeno, NO2, NH2, OH, OCF3, O-alquilo C1-3 , alquilo C1-4, C(CH3)2CO2CH3, C(CH3)2OH, C(CH3)2CN, CH2CN, OCH2CN, OCH2CH2OCH3, OCH2C(O)NHCH3, OCH2C(O)N(CH3)2, C(O)CH3, C(O)O-alquiloC1-3, cicloalquilo C3-6, OCHF2, fenilo, CHF2, CF3, O-fenilo, CN, SO2Me, OCH2-fenilo, CH2O-fenilo, piperidinilo, piperazinilo, oxetano, oxetano-CH3, tetrahidrofurilo, tetrahidropiranilo, morfolinilo, het, O-het, O-CH2-het, o CH2-het; het es piridina, pirimidina, piridazina, pirazina, pirazol, isoxazol, imidazol o triazol; y además, en donde el sustituyente fenilo o het en A puede estar además sustituido con uno o dos: halógeno, O- alquilo C1-3, CN, alquilo C1-4, CF3, C(O)NH2, N(alquilo C1-3)2 o SO2-alquilo C1-3; y el sustituyente alquilo C1-4, cicloalquilo C3-6 o O-alquilo C1-3 en A puede estar además sustituido con CN o OH; o A es (CH2)n-(CRaRb)-(CH2)m-Rx; Ra es hidrógeno o alquilo C1-3, en donde el alquilo C1-3 puede estar además sustituido con uno o más halógenos; Rb es alquilo C1-3; O Ra y Rb junto con el átomo de carbono al que están unidos para formar un grupo cicloalquilo C3-6; O uno de los átomos de carbono en el grupo cicloalquilo C3-6 formado por Ra y Rb se puede sustituir por un oxígeno para formar un grupo oxetano, tetrahidrofurilo o tetrahidropiranilo; Rx es O-fenilo, fenilo, C(O)NH-fenilo o OCH2-fenilo; en donde el fenilo puede estar sustituido con uno o dos sustituyentes seleccionados de: halógeno, O-alquilo C1-3, CN, alquilo C1-4 o CF3; m es 0 o 1; n es 0, 1 o 2; y es 1, 2 o 3; o una de sus sales farmacéuticamente aceptable.
ES12800913T 2011-06-17 2012-06-15 Antagonistas espiro-cíclicos de TRPV4 Active ES2571409T3 (es)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201161498104P 2011-06-17 2011-06-17
PCT/US2012/042607 WO2012174342A1 (en) 2011-06-17 2012-06-15 Trpv4 antagonists

Publications (1)

Publication Number Publication Date
ES2571409T3 true ES2571409T3 (es) 2016-05-25

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US (1) US9487507B2 (es)
EP (1) EP2720546B1 (es)
JP (1) JP5969016B2 (es)
ES (1) ES2571409T3 (es)
WO (1) WO2012174342A1 (es)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2595606T3 (es) 2011-06-17 2017-01-02 Glaxosmithkline Intellectual Property (No. 2) Limited Antagonistas TRPV4
JO3154B1 (ar) * 2011-06-17 2017-09-20 Glaxosmithkline Llc عوامل مضادة لـ trpv4
WO2013146754A1 (ja) 2012-03-27 2013-10-03 塩野義製薬株式会社 Ｔｒｐｖ４阻害活性を有する芳香族複素５員環誘導体
WO2015046193A1 (ja) 2013-09-25 2015-04-02 塩野義製薬株式会社 Ｔｒｐｖ４阻害活性を有する芳香族複素環式アミン誘導体
EP3116858B1 (en) 2014-03-14 2020-11-11 RaQualia Pharma Inc. Azaspiro derivatives as trpm8 antagonists
US10968209B2 (en) 2016-05-19 2021-04-06 Glaxosmithkline Intellectual Property (No.2) Limited TRPV4 antagonist
RU2018144774A (ru) * 2016-05-19 2020-06-19 Глэксосмитклайн Интеллекчуал Проперти (Но.2) Лимитед Антагонист trpv4
WO2018185701A1 (en) * 2017-04-06 2018-10-11 Glaxosmithkline Intellectual Property (No.2) Limited Trpv4 antagonists as antitussive agents
US20230339934A1 (en) 2020-04-30 2023-10-26 Raqualia Pharma Inc. Pyrimidin-4(3h)-one derivatives as trpv4 antagonists
CN111704613B (zh) * 2020-06-23 2021-07-06 中国人民解放军军事科学院军事医学研究院 咪唑类衍生物及其作为trpv4抑制剂的用途
JPWO2022014707A1 (es) 2020-07-16 2022-01-20
TW202409024A (zh) 2022-07-08 2024-03-01 美商愛克堤歐生物科學公司 治療性化合物及方法

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EP1086950B1 (en) * 1998-05-26 2010-09-29 Chugai Seiyaku Kabushiki Kaisha Heterocyclic indole derivatives and mono- or diazaindole derivatives
JP2007534624A (ja) * 2003-07-16 2007-11-29 ニューロジェン・コーポレーション ビアリールピペラジニル−ピリジン類縁体
TW200819457A (en) * 2006-08-30 2008-05-01 Actelion Pharmaceuticals Ltd Spiro antibiotic derivatives
US20100197699A1 (en) * 2007-02-01 2010-08-05 Glaxo Group Limited I-OXA-3-Azaspiro (4.5) Decan-2-One And 1-OXA-3, 8-Diazaspiro (4.5) Decan-2-One Derivatives For The Treatment of Eating Disorders
EP2118097A1 (en) * 2007-02-01 2009-11-18 Glaxo Group Limited 1-oxa-3-azaspiro[4,5]decan-2-one derivatives for the treatment of eating disorders
GB0707934D0 (en) * 2007-04-24 2007-05-30 Glaxo Group Ltd Chemical compounds
CA2708320A1 (en) * 2007-08-09 2009-02-19 Abbott Laboratories Amide derivatives as trpv1 antagonists
TW200944520A (en) * 2008-01-29 2009-11-01 Glaxo Group Ltd Spiro compounds as NPY Y5 receptor antagonists
WO2010011914A1 (en) * 2008-07-25 2010-01-28 Smithkline Beecham Corporation Trpv4 antagonists
JP2012006837A (ja) * 2008-09-30 2012-01-12 Mochida Pharmaceut Co Ltd ２−インドールアクリルアミド類縁体
ES2595606T3 (es) 2011-06-17 2017-01-02 Glaxosmithkline Intellectual Property (No. 2) Limited Antagonistas TRPV4
JO3154B1 (ar) 2011-06-17 2017-09-20 Glaxosmithkline Llc عوامل مضادة لـ trpv4

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EP2720546A4 (en) 2014-10-08
JP2014523420A (ja) 2014-09-11
EP2720546A1 (en) 2014-04-23
WO2012174342A1 (en) 2012-12-20
US9487507B2 (en) 2016-11-08
EP2720546B1 (en) 2016-04-06
US20140113916A1 (en) 2014-04-24
JP5969016B2 (ja) 2016-08-10

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