AR084507A1 - Derivados de indazoliltriazol - Google Patents
Derivados de indazoliltriazolInfo
- Publication number
- AR084507A1 AR084507A1 ARP110104813A ARP110104813A AR084507A1 AR 084507 A1 AR084507 A1 AR 084507A1 AR P110104813 A ARP110104813 A AR P110104813A AR P110104813 A ARP110104813 A AR P110104813A AR 084507 A1 AR084507 A1 AR 084507A1
- Authority
- AR
- Argentina
- Prior art keywords
- alkyl
- hal
- denotes
- cycloalkyl
- het1
- Prior art date
Links
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 44
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 14
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 abstract 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 8
- 125000005010 perfluoroalkyl group Chemical group 0.000 abstract 8
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 abstract 8
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 7
- 125000004432 carbon atom Chemical group C* 0.000 abstract 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 5
- 125000005842 heteroatom Chemical group 0.000 abstract 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 5
- 229910052760 oxygen Inorganic materials 0.000 abstract 5
- 229910052717 sulfur Inorganic materials 0.000 abstract 5
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 4
- 229920006395 saturated elastomer Polymers 0.000 abstract 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 abstract 3
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 2
- 125000005330 8 membered heterocyclic group Chemical group 0.000 abstract 2
- 125000002619 bicyclic group Chemical group 0.000 abstract 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- 125000002950 monocyclic group Chemical group 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 125000003003 spiro group Chemical group 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
- 208000023275 Autoimmune disease Diseases 0.000 abstract 1
- 206010061218 Inflammation Diseases 0.000 abstract 1
- 229910003827 NRaRb Inorganic materials 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 abstract 1
- 125000002837 carbocyclic group Chemical group 0.000 abstract 1
- 150000004677 hydrates Chemical class 0.000 abstract 1
- 230000004054 inflammatory process Effects 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000012453 solvate Substances 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- 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
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- 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
- A61K31/4192—1,2,3-Triazoles
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
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- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/537—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines spiro-condensed or forming part of bridged ring systems
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- A61K31/5375—1,4-Oxazines, e.g. morpholine
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- A61K31/551—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
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Abstract
Compuestos de la fórmula (1) se usan para el tratamiento de inflamación y trastornos autoinmunes. Composición farmacéutica, proceso de preparación y uso como moduladores de interleuquina-IRAK.Reivindicación 1: Un compuesto de la formula (1) en donde Q denota Ar o Het; E denota -(CH2)mCO-, -(CH2)mSO2, -(CH2)mNHCO- o un enlace simple; R1 denota H, OH, NH-alquilo C1-6, O-alquilo C1-6, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, Cyc, Hal, Het1, O-Het1, CO-Het1, NH-Het1, CO-Ar1, O-Ar1, Ar1, NH-Ar1, -(CH2)qHet1, -CONH-(CH2)qHet1, -CONH-Het1, -(CH2)qO-Het1, -(CH2)qO-Ar1, -(CH2)qAr1, -CONH-(CH2)qAr1, -CONH-Ar1, -CONH-cicloalquilo C3-6, -(CH2)qHal, -(CH2)qCyC, CF3, -(CH2)sNH-(CH2)q-Het1, -(CH2)sNH-(CH2)q-Ar1, en donde NH-alquilo C1-6, O-alquilo C1-6, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, cicloalquilo C3-6 puede estar sustituido con 1 a 3 grupos seleccionados, de modo independiente, de O-alquilo C1-3, OH, CONH2, NH2; R2 denota H, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, Hal, CF3, con preferencia H; R3 denota Het1, Ar1, NRaRb, COOH, -(CH2)qHet1, -(CH2)qAr1, -(CH2)qNRaRb, -(CH2)qCOOH o alquilo C1-6, en donde 1 a 3 átomos de hidrógeno pueden estar reemplazados, de modo independiente, por OH o CF3; R4 denota H, alquilo C1-6, alquenilo C2-6, Hal; Ra denota H, alquilo C1-6 lineal, ramificado o cíclico; Rb denota H, Hetb, Arb, -CO-Hetb, -CO-Arb, un cicloalquilo C3-8 o un alquilo C1-6 lineal o ramificado, en donde 1 a 3 átomos de hidrógeno pueden estar reemplazados por Hetb, Arb, NH2, N(alquilo C1-6)2, NH(alquilo C1-6), N(alquilo C1-6)(cicloalquilo C3-8), NH(cicloalquilo C3-8), O(alquilo C1-6), CN, OH, CF3, Hal; n es 0, 1, 2, 3 ó 4; m es 0, 1, 2, 3 ó 4; q es 1, 2 ó 3; s es 0, 1, 2 ó 3; Hal denota Cl, Br, I, F, con preferencia Cl o F; Ar denota un grupo arileno monocíclico divalente o bicíclico fusionado que tiene 6 a 14 átomos de carbono, que también puede estar sustituido con 1 a 4 sustituyentes seleccionados de Hal, alquilo C1-6, -(CH2)mO-alquilo C1-6, CN, OH, NO2, CF3, -(CH2)mCOOH, -(CH2)mCOO-alquilo C1-6; Het denota un grupo heterocíclico insaturado, saturado o aromático monocíclico divalente o bicíclico fusionado que tiene 1 a 5 heteroátomos seleccionados de modo independiente de N, O, S y/o un grupo -C=O que también puede estar sustituido con 1 a 4 sustituyentes seleccionados de Hal, alquilo C1-6, -(CH2)mO-alquilo C1-6, CN, OH, NO2, CF3, -(CH2)mCOOH, -(CH2)mCOO-alquilo C1-6; Ar1 denota un anillo carbocíclico aromático monocíclico o bicíclico que tiene 6 a 14 átomos de carbono, que no está sustituido o que está monosustituido, disustituido o trisustituido con Hal, -CF3, -OCF3, -NO2, -CN, perfluoroalquilo, Hal, -CF3, -OCF3, -NO2, -CN, perfluoroalquilo, alquilo C1-6 lineal o ramificado, cicloalquilo, -OH, -O-alquilo C1-6, -COalquilo C1-6, -NH2, -COH, -COOH, -CONH2, un grupo Rb tales como -CH2O(alquilo C1-6), -SO2NRaRb o SO2(alquilo C1-6); Het1 denota un anillo heterocíclico saturado, insaturado o aromático monocíclico o bicíclico (fusionado, en puente o espiro) que tiene 1 a 4 heteroátomos seleccionados de modo independiente de N, O, S y/o un grupo CO, que no está sustituido o que está monosustituido, disustituido o trisustituido con Hal, -CF3, -OCF3, -NO2, -CN, perfluoroalquilo, alquilo C1-6 lineal o ramificado, cicloalquilo C3-8, -OH, -O-alquilo C1-6, -NH2, -N(alquilo C1-6)2, -COH, -COOH, -CONH2, -COalquilo C1-6, -NHCO(cicloalquilo C3-6), un grupo Rb tales como -SO2NRaRb o SO2(alquilo C1-6); Hetb denota un anillo heterocíclico saturado, insaturado o aromático monocíclico o bicíclico (fusionado o espiro) que tiene 1 a 4 heteroátomos seleccionados de modo independiente de N, O, S y/o un grupo CO, que no está sustituido o que está monosustituido, disustituido o trisustituido con Hal, -CF3, -OCF3, -NO2, CN, perfluoroalquilo, -OH, -O-alquilo C1-6, -NH2, -COH, -COOH, - CONH2 o con un alquilo C1-6 lineal o ramificado, en donde 1 a 3 átomos de hidrógeno pueden estar reemplazados por NH2, N(alquilo C1-6)2, NH(alquilo C1-6), N(alquilo C1-6)(cicloalquilo C3-8), NH(cicloalquilo C3-8), O(alquilo C1-6), CN, OH, CF3, Hal, cicloalquilo C3-8, o con un anillo heterocíclico de 4 a 8 miembros que contiene un heteroátomo seleccionado de O, S y N; Arb denota un anillo carbocíclico aromático monocíclico o bicíclico que tiene 6 a 14 átomos de carbono, que no está sustituido o que está monosustituido, disustituido o trisustituido con Hal, -CF3, -OCF3, -NO2, -CN, perfluoroalquilo, Hal, -CF3, -OCF3, -NO2, -CN, perfluoroalquilo, -OH, -O-alquilo C1-6, -NH2, -COH, -COOH, -CONH2 o con un alquilo C1-6 lineal o ramificado, en donde 1 a 3 átomos de hidrógeno pueden estar reemplazados por NH2, N(alquilo C1-6)2, NH(alquilo C1-6), N(alquilo C1-6)(cicloalquilo C3-8), NH(cicloalquilo C3-8), O(alquilo C1-6), CN, OH, CF3, Hal, cicloalquilo C3-8 o con un anillo heterocíclico de 4 a 8 miembros que contiene un heteroátomo seleccionado de O, S y N; Cyc denota un anillo carbocíclico saturado o insaturado que tiene 3 a 8 átomos de carbono, con preferencia 5 ó 6 átomos de carbono, en donde 1 a 5 átomos de H están reemplazados por Hal, -CF3, -OCF3, -NO2, -CN, perfluoroalquilo, Hal, -CF3, -OCF3, -NO2, -CN, perfluoroalquilo, alquilo C1-6 lineal o ramificado, cicloalquilo, -OH, -O-alquilo C1-6, -COalquilo C1-6, -NH2, -COH, -COOH, -CONH2, un grupo Rb tales como -CH2O(alquilo C1-6), -SO2NRaRb o SO2(alquilo C1-6); y sus derivados, solvatos, tautómeros, sales, hidratos y estereoisómeros farmacéuticamente aceptables, incluyendo sus mezclas en todas las proporciones.
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| US201061424890P | 2010-12-20 | 2010-12-20 | |
| EP10195867 | 2010-12-20 |
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| EA (1) | EA023544B1 (es) |
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| SI (1) | SI2655357T1 (es) |
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- 2011-12-16 HU HUE11801711A patent/HUE029617T2/en unknown
- 2011-12-16 RS RS20160779A patent/RS55165B1/sr unknown
- 2011-12-16 PT PT118017110T patent/PT2655357T/pt unknown
- 2011-12-16 EA EA201300730A patent/EA023544B1/ru not_active IP Right Cessation
- 2011-12-16 AU AU2011347711A patent/AU2011347711B2/en not_active Ceased
- 2011-12-16 HR HRP20161127TT patent/HRP20161127T1/hr unknown
- 2011-12-16 SI SI201130961A patent/SI2655357T1/sl unknown
- 2011-12-16 JP JP2013545217A patent/JP6007189B2/ja not_active Expired - Fee Related
- 2011-12-16 KR KR1020137019290A patent/KR101842098B1/ko not_active Expired - Fee Related
- 2011-12-16 ES ES11801711.0T patent/ES2592713T3/es active Active
- 2011-12-20 AR ARP110104813A patent/AR084507A1/es active IP Right Grant
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2013
- 2013-06-13 IL IL226912A patent/IL226912A/en active IP Right Grant
- 2013-07-19 ZA ZA2013/05483A patent/ZA201305483B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KR20130133252A (ko) | 2013-12-06 |
| CN103429585A (zh) | 2013-12-04 |
| EA201300730A1 (ru) | 2013-12-30 |
| AU2011347711B2 (en) | 2017-02-02 |
| WO2012084704A1 (en) | 2012-06-28 |
| LT2655357T (lt) | 2016-10-10 |
| PL2655357T3 (pl) | 2016-12-30 |
| EP2655357B1 (en) | 2016-06-22 |
| AU2011347711A1 (en) | 2013-08-01 |
| US20130274241A1 (en) | 2013-10-17 |
| ES2592713T3 (es) | 2016-12-01 |
| SG191205A1 (en) | 2013-07-31 |
| HK1191938A1 (en) | 2014-08-08 |
| US9073892B2 (en) | 2015-07-07 |
| HRP20161127T1 (hr) | 2016-11-18 |
| RS55165B1 (sr) | 2017-01-31 |
| JP2014500286A (ja) | 2014-01-09 |
| PT2655357T (pt) | 2016-09-28 |
| CN103429585B (zh) | 2015-07-08 |
| HUE029617T2 (en) | 2017-03-28 |
| EA023544B1 (ru) | 2016-06-30 |
| IL226912A (en) | 2017-01-31 |
| BR122021014375B1 (pt) | 2021-11-30 |
| MX2013007149A (es) | 2013-10-30 |
| CA2822166C (en) | 2019-10-29 |
| BR112013015460A2 (pt) | 2016-09-20 |
| KR101842098B1 (ko) | 2018-03-26 |
| EP2655357A1 (en) | 2013-10-30 |
| BR112013015460B1 (pt) | 2022-01-25 |
| SI2655357T1 (sl) | 2016-10-28 |
| ZA201305483B (en) | 2014-06-25 |
| CA2822166A1 (en) | 2012-06-28 |
| JP6007189B2 (ja) | 2016-10-12 |
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