ES2577306T3 - Nuevos compuestos de tiofenilamida bicíclicos - Google Patents

Nuevos compuestos de tiofenilamida bicíclicos Download PDF

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ES2577306T3
ES2577306T3 ES13728748.8T ES13728748T ES2577306T3 ES 2577306 T3 ES2577306 T3 ES 2577306T3 ES 13728748 T ES13728748 T ES 13728748T ES 2577306 T3 ES2577306 T3 ES 2577306T3
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substituted
cycloalkyl
carbon atoms
heterocycloalkyl
heteroaryl
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Bernd Buettelmann
Simona M. Ceccarelli
Holger Kuehne
Bernd Kuhn
Werner Neidhart
Ulrike Obst Sander
Hans Richter
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F Hoffmann La Roche AG
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    • C07—ORGANIC CHEMISTRY
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    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 carbon atoms of the hetero ring
    • C07D333/66—Nitrogen atoms not forming part of a nitro radical
    • 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
    • A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
    • A61K31/381—Heterocyclic compounds having sulfur as a ring hetero atom having five-membered rings
    • 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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/42—Oxazoles
    • A61K31/422—Oxazoles not condensed and containing further heterocyclic 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
    • A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
    • 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
    • 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
    • A61P35/00—Antineoplastic 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • 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
    • C07D413/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/10—Spiro-condensed systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
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  • General Health & Medical Sciences (AREA)
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  • Urology & Nephrology (AREA)
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  • Heart & Thoracic Surgery (AREA)
  • Endocrinology (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Vascular Medicine (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Compuestos de fórmula (I)**Fórmula** en la que: R1 y R2 juntos forman un -CR14>=CR15-CR16>=CR17-, -CR14R15-O-(CR16R17)m-CR18R19-, -CR14R15-(CR16R17)m-O CR18R19-, -O-CR14R15-(CR16R17)m-CR18R19-, -CR14R15-NR22-CR16R17-CR18R19-, -CR14R15-S(O)2-CR16R17-CR18R19-, - CR14R15-CR20R21- o -CR14R15-CR16R17-(CR18R19)p-CR20R21-; R3 es un arilo sustituido, heterocicloalquilo sustituido o heteroarilo sustituido, en el que el arilo sustituido, heterocicloalquilo sustituido y heteroarilo sustituido están sustituidos con R23 y pueden estar sustituidos adicionalmente con R24 y/o R25; R4 es H o alquilo; R5 y R6 se seleccionan independientemente entre H, alquilo y cicloalquilo; R7 es H, alquilo o cicloalquilo; A es NR8 o CR9R10; E es NR11 o CR12R13; R8 y R11 se seleccionan independientemente entre H, alquilo y cicloalquilo; R9, R10, R12 y R13 se seleccionan independientemente entre H, halógeno, alquilo, haloalquilo y cicloalquilo; o R5 y R12, junto con los átomos de carbono a los que están unidos, forman un cicloalquilo sustituido, arilo sustituido, heterocicloalquilo sustituido o heteroarilo sustituido, en el que el cicloalquilo sustituido, arilo sustituido, heterocicloalquilo sustituido y heteroarilo sustituido están sustituidos con R26 y pueden estar sustituidos adicionalmente con R27 y/o R28, en el que en el caso de que R5 y R12 junto con los átomos de carbono a los que están unidos formen un arilo sustituido o heteroarilo sustituido, entonces R6 y R13 están ausentes; o R8 y R12, junto con los átomos de nitrógeno y de carbono a los que están unidos, forman un heterocicloalquilo sustituido o heteroarilo sustituido, en el que el heterocicloalquilo sustituido y heteroarilo sustituido están sustituidos con R26 y pueden estar sustituidos adicionalmente con R27 y/o R28, en el que, en el caso de que R8 y R12, junto con los átomos de carbono a los que están unidos, formen un heteroarilo sustituido, entonces R13 está ausente; o R9 y R11, junto con los átomos de nitrógeno y de carbono a los que están unidos, forman un heterocicloalquilo sustituido o heteroarilo sustituido, en el que el heterocicloalquilo sustituido y heteroarilo sustituido están sustituidos con R26 y pueden estar sustituidos adicionalmente con R27 y/o R28, en el que en el caso de que R9 y R11, junto con los átomos de carbono a los que están unidos, formen un heteroarilo sustituido, entonces R10 está ausente; o R9 y R12, junto con los átomos de carbono a los que están unidos, forman un cicloalquilo sustituido, arilo sustituido, heterocicloalquilo sustituido o heteroarilo sustituido, en el que el cicloalquilo sustituido, arilo sustituido, heterocicloalquilo sustituido y heteroarilo sustituido están sustituidos con R26 y pueden estar sustituidos adicionalmente con R27 y/o R28, en el que, en el caso de que R9 y R12 junto con los átomos de carbono a los que están unidos formen un arilo sustituido o heteroarilo sustituido, entonces R10 y R13 están ausentes; o R10 y R13 junto con los átomos de carbono a los que están unidos forman un cicloalquilo sustituido, arilo sustituido, heterocicloalquilo sustituido o heteroarilo sustituido, en el que el cicloalquilo sustituido, arilo sustituido, heterocicloalquilo sustituido y heteroarilo sustituido están sustituidos con R29 y pueden estar sustituidos adicionalmente con R30 y/o R31, en el que en el caso de que R10 y R13 junto con los átomos de carbono a los que están unidos formen un arilo sustituido o heteroarilo sustituido, entonces R9 y R12 están ausentes; o R10 y R13 junto con los átomos de carbono a los que están unidos forman un doble enlace; R14, R15, R16, R17, R18, R19, R20, R21, R23, R24, R25, R26, R27, R28, R29, R30 y R31 se seleccionan independientemente entre H, oxo, hidroxi, halógeno, alquilo, cicloalquilo, haloalquilo, alcoxi, alcoxialquilo, alcoxicarbonilo y carboxi; o R16 y R17 junto con los átomos de carbono a los que están unidos forman un cicloalquilo o heterocicloalquilo; o R14 y R20 junto con los átomos de carbono a los que están unidos forman un -CH2- o -CH2-CH2-; R22 es H, alquilo, cicloalquilo o alcoxicarbonilo; m es cero o 1; n es cero o 1; p es cero, 1 o 2; o las sales farmacéuticamente aceptables.
ES13728748.8T 2012-06-19 2013-06-14 Nuevos compuestos de tiofenilamida bicíclicos Active ES2577306T3 (es)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP12172528 2012-06-19
EP12172528 2012-06-19
PCT/EP2013/062314 WO2013189841A1 (en) 2012-06-19 2013-06-14 New bicyclic thiophenylamide compounds

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US (1) US9604977B2 (es)
EP (1) EP2861574B1 (es)
JP (1) JP6215924B2 (es)
KR (1) KR20150023804A (es)
CN (1) CN104395301B (es)
AR (1) AR091464A1 (es)
BR (1) BR112014030474A2 (es)
CA (1) CA2869232A1 (es)
ES (1) ES2577306T3 (es)
HK (1) HK1206340A1 (es)
MX (1) MX2014014708A (es)
RU (1) RU2644565C2 (es)
TW (1) TW201402560A (es)
WO (1) WO2013189841A1 (es)

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CN104693169A (zh) * 2015-02-11 2015-06-10 佛山市赛维斯医药科技有限公司 一种硝基取代的甲氧苯噻吩酰胺类双靶点抑制剂及其用途
CN104803946A (zh) * 2015-03-03 2015-07-29 佛山市赛维斯医药科技有限公司 含腈基噻唑和环戊二烯结构的ptp1b抑制剂及其用途
IL305371A (en) * 2017-10-04 2023-10-01 Verrica Pharmaceuticals Inc Synthesis of cantharidin
CN108191885B (zh) * 2018-01-29 2020-08-04 华东师范大学 一类哌啶并噻吩类小分子有机化合物及其应用
CN109884212A (zh) * 2019-03-27 2019-06-14 清华大学深圳研究生院 基于化学衍生化与hplc-ms的不饱和脂肪酸定量方法
CN115636724A (zh) * 2022-10-18 2023-01-24 浙大宁波理工学院 一种4-氟-4-甲基环己醇及其制备方法

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AU2004270394A1 (en) * 2003-09-10 2005-03-17 Gpc Biotech Ag Heterobicyclic compounds as pharmaceutically active agents
US20050085531A1 (en) * 2003-10-03 2005-04-21 Hodge Carl N. Thiophene-based compounds exhibiting ATP-utilizing enzyme inhibitory activity, and compositions, and uses thereof
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JP6215924B2 (ja) 2017-10-18
BR112014030474A2 (pt) 2017-06-27
JP2015520199A (ja) 2015-07-16
RU2644565C2 (ru) 2018-02-13
MX2014014708A (es) 2015-02-24
US9604977B2 (en) 2017-03-28
RU2014152350A (ru) 2016-08-10
CN104395301B (zh) 2017-07-28
EP2861574A1 (en) 2015-04-22
WO2013189841A1 (en) 2013-12-27
KR20150023804A (ko) 2015-03-05
EP2861574B1 (en) 2016-04-20
CA2869232A1 (en) 2013-12-27
CN104395301A (zh) 2015-03-04
US20150175594A1 (en) 2015-06-25
HK1206340A1 (en) 2016-01-08
AR091464A1 (es) 2015-02-04

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