AR091464A1 - Compuestos biciclicos de tiofenilamida - Google Patents

Compuestos biciclicos de tiofenilamida

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Publication number
AR091464A1
AR091464A1 ARP130102125A AR091464A1 AR 091464 A1 AR091464 A1 AR 091464A1 AR P130102125 A ARP130102125 A AR P130102125A AR 091464 A1 AR091464 A1 AR 091464A1
Authority
AR
Argentina
Prior art keywords
substituted
cycloalkyl
carbon atoms
attached form
heterocycloalkyl
Prior art date
Application number
Other languages
English (en)
Inventor
Buettelmann Bernd
M Ceccarelli Simona
Kuehne Holger
Kuhn Bernd
Neidhart Werner
Obst Sander Ulrike
Richter Hans
Original Assignee
Hoffmann La Roche
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
Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche
Publication of AR091464A1 publication Critical patent/AR091464A1/es

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    • 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
    • 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
    • C07D417/04—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
    • 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

Abstract

Composiciones que incluyen los compuestos y métodos de uso de los compuestos para diabetes tipo 2, aterosclerosis, cáncer, esteatohepatitis, enfermedades renales crónicas. Son inhibidores de las proteínas FABP 4 y/o 5. Reivindicación 1: Compuestos de la fórmula (1) 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, dichos arilo sustituido, heterocicloalquilo sustituido y heteroarilo sustituido están sustituidos por R²³ y también pueden estar sustituidos por R²⁴ y/o R²⁵; R⁴ es H o alquilo; R⁵ y R⁶ se eligen con independencia 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 eligen con independencia entre H, alquilo y cicloalquilo; R⁹, R¹⁰, R¹² y R¹³ se eligen con independencia 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, dichos cicloalquilo sustituido, arilo sustituido, heterocicloalquilo sustituido y heteroarilo sustituido están sustituidos por R²⁶ y también pueden estar sustituidos por R²⁷ y/o R²⁸, pero 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 estarán 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, dichos heterocicloalquilo sustituido y heteroarilo sustituido están sustituidos por R²⁶ y también pueden estar sustituidos por R²⁷ y/o R²⁸, pero 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 estará 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, dichos heterocicloalquilo sustituido y heteroarilo sustituido están sustituidos por R²⁶ y también pueden estar sustituidos por R²⁷ y/o R²⁸, pero 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 estará 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, dichos cicloalquilo sustituido, arilo sustituido, heterocicloalquilo sustituido y heteroarilo sustituido están sustituidos por R²⁶ y también pueden estar sustituidos por R²⁷ y/o R²⁸, pero 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 estarán 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, dichos cicloalquilo sustituido, arilo sustituido, heterocicloalquilo sustituido y heteroarilo sustituido están sustituidos por R²⁹ y también pueden estar sustituidos por R³⁰ y/o R³¹, pero 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 estarán 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 eligen con independencia 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 ó 2; o las sales farmacéuticamente aceptables.
ARP130102125 2012-06-19 2013-06-17 Compuestos biciclicos de tiofenilamida AR091464A1 (es)

Applications Claiming Priority (1)

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EP12172528 2012-06-19

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AR091464A1 true AR091464A1 (es) 2015-02-04

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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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WO2005023818A2 (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
US7772232B2 (en) * 2004-04-15 2010-08-10 Bristol-Myers Squibb Company Quinazolinyl compounds as inhibitors of potassium channel function
EP1676834A1 (en) * 2004-12-30 2006-07-05 Sanofi-Aventis Deutschland GmbH Fused bicyclic carboxamide derivates for use as CXCR2 inhibitors in the treatment of inflammation
AU2006218403A1 (en) * 2005-03-03 2006-09-08 Sirtris Pharmaceuticals, Inc. Fused heterocyclic compounds and their use as sirtuin modulators
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JP5232144B2 (ja) * 2006-06-28 2013-07-10 サノフイ Ｃｘｃｒ２阻害剤
RU2364597C1 (ru) * 2007-12-14 2009-08-20 Андрей Александрович Иващенко ГЕТЕРОЦИКЛИЧЕСКИЕ ИНГИБИТОРЫ Hh-СИГНАЛЬНОГО КАСКАДА, ЛЕКАРСТВЕННЫЕ КОМПОЗИЦИИ НА ИХ ОСНОВЕ И СПОСОБ ЛЕЧЕНИЯ ЗАБОЛЕВАНИЙ, СВЯЗАННЫХ С АББЕРАНТНОЙ АКТИВНОСТЬЮ Hh СИГНАЛЬНОЙ СИСТЕМЫ

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WO2013189841A1 (en) 2013-12-27
JP6215924B2 (ja) 2017-10-18
RU2644565C2 (ru) 2018-02-13
EP2861574B1 (en) 2016-04-20
JP2015520199A (ja) 2015-07-16
HK1206340A1 (en) 2016-01-08
EP2861574A1 (en) 2015-04-22
KR20150023804A (ko) 2015-03-05
ES2577306T3 (es) 2016-07-14
US9604977B2 (en) 2017-03-28
CN104395301B (zh) 2017-07-28
CN104395301A (zh) 2015-03-04
BR112014030474A2 (pt) 2017-06-27
MX2014014708A (es) 2015-02-24
US20150175594A1 (en) 2015-06-25
RU2014152350A (ru) 2016-08-10
TW201402560A (zh) 2014-01-16
CA2869232A1 (en) 2013-12-27

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