ES2581565T3 - Aminotriazolopiridinas y su uso como inhibidores de cinasas - Google Patents
Aminotriazolopiridinas y su uso como inhibidores de cinasas Download PDFInfo
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- ES2581565T3 ES2581565T3 ES09789271.5T ES09789271T ES2581565T3 ES 2581565 T3 ES2581565 T3 ES 2581565T3 ES 09789271 T ES09789271 T ES 09789271T ES 2581565 T3 ES2581565 T3 ES 2581565T3
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Abstract
Un compuesto de fórmula (I):**Fórmula** o una sal, tautómero, estereoisómero o solvato farmacéuticamente aceptable del mismo, en donde: 5 R1 es un arilo sustituido o sin sustituir o un heterociclilo sustituido o sin sustituir; R2 es un alquilo C1-8 sustituido o sin sustituir, un cicloalquilo sustituido o sin sustituir, un heterociclilalquilo sustituido o sin sustituir, un aralquilo sustituido o sin sustituir, -OR3, -C(>=O)R5, -C(>=O)NR3R4, -NHC(>=O)R3, - (CH2)0-2CR6(OR3)R4 o un heterociclilo sustituido o sin sustituir seleccionado de 1,2,3,6-tetrahidropiridilo, bencisoxazolilo o isoindolin-1-onilo. R3 y R4 son cada vez que aparecen, independientemente, -H, un alquilo C1-8 sustituido o sin sustituir, un arilo sustituido o sin sustituir, un heteroarilo sustituido o sin sustituir, un cicloalquilo sustituido o sin sustituir, un heterociclilo sustituido o sin sustituir, un aralquilo sustituido o sin sustituir o un heterociclilalquilo sustituido o sin sustituir; R5 es alquilo C1-8 sustituido o sin sustituir, un arilo sustituido o sin sustituir, un heteroarilo sustituido o sin sustituir, un cicloalquilo sustituido o sin sustituir, un heterociclilo sustituido o sin sustituir, un aralquilo sustituido o sin sustituir o un heterociclilalquilo sustituido o sin sustituir; y R6 es -H, o un alquilo C1-8 sustituido o sin sustituir, o junto con R4 y los átomos a los que están unidos forman un heterociclilo sustituido o sin sustituir.
Description
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y sales farmacéuticamente aceptables, tautómeros, estereoisómeros y solvatos de los mismos, en donde:
R1 es un arilo sustituido o sin sustituir o un heterociclilo sustituido o sin sustituir;
R2 es un alquilo C1-8 sustituido o sin sustituir, un cicloalquilo sustituido o sin sustituir, un heterociclilalquilo sustituido o sin sustituir, un aralquilo sustituido o sin sustituir, -NR3R4, -OR3, -C(=O)R5, -C(=O)NR3R4, -NHC(=O)R3, -(CH2)02CR6(OR3)R4, o un heterociclilo sustituido o sin sustituir seleccionado de 1,2,3,6-tetrahidropiridilo, bencisoxazolilo o isoindolin-1-onilo.
R3 y R4 son cada vez que aparecen, independientemente, -H, un alquilo C1-8 sustituido o sin sustituir, un arilo sustituido o sin sustituir, un heteroarilo sustituido o sin sustituir, un cicloalquilo sustituido o sin sustituir, un heterociclilo sustituido o sin sustituir, un aralquilo sustituido o sin sustituir o un heterociclilalquilo sustituido o sin sustituir;
R5 es alquilo C1-8 sustituido o sin sustituir, un arilo sustituido o sin sustituir, un heteroarilo sustituido o sin sustituir, un cicloalquilo sustituido o sin sustituir, un heterociclilo sustituido o sin sustituir, un aralquilo sustituido o sin sustituir o un heterociclilalquilo sustituido o sin sustituir; y
R6 es -H, o un alquilo C1-8 sustituido o sin sustituir, o junto con R4 y los átomos a los que están unidos forman un heterociclilo sustituido o sin sustituir.
En una realización, el compuesto de heteroarilo es un compuesto de fórmula (I), en donde R1 es un arilo sustituido o sin sustituir, por ejemplo, un fenilo sustituido o sin sustituir. En algunas de dichas realizaciones, R1 es fenilo, sustituido con uno o más de alquilo C1-4 sustituido o sin sustituir, heterociclilo sustituido o sin sustituir, halógeno, hidroxilo, alcoxi, carboxi, -CN, -(alquil C0-4)NR2, -O(alquil C1-4)NR2, -NR2, o -C(=O)NR2, en donde cada R es independientemente H, un alquilo C1-6 sustituido o sin sustituir, o un heterociclilo sustituido o sin sustituir. Por ejemplo, en ciertas realizaciones, R1 es fenilo, sustituido con uno o más de -F, -Cl, -CF3, -CN, hidroxi, carboxi, metilo, -(alquil C0-4)NH2, -(alquil C0-4)NH(alquilo C1-4), -O(alquilo C1-4), -O(alquil C1-4)O(alquilo C1-4), -O(alquil C1-4)NH2, N(alquilo C1-4)2, -C(=O)NH2, -C(=O)NH(alquilo C1-4), -C(=O)NH(piperidilo sustituido o sin sustituir) o un heterociclilo sustituido o sin sustituir seleccionado de morfolinilo, triazolilo, pirrolidilo, imidazolilo o pirrolidinonilo.
En algunas realizaciones, el compuesto de heteroarilo es un compuesto de fórmula (I), en donde R1 es un heterociclilo sustituido o sin sustituir. Por ejemplo, en ciertas realizaciones, R1 es un heterociclilo sustituido o sin sustituir seleccionado de isoindolin-1-onilo, piridilo, pirimidilo, indazolilo, indolinilo, isoindolinilo, indolin-2-onilo, quinolinilo, dihidroisoquinolin-1-onilo, benzotriazolilo, bencimidazolilo, 1H-pirazolo[3,4-b]piridilo, 1H-pirazolo[4,3b]piridilo, 1H-benzo[d]imidazol-2(3H)-onilo, benzoisoxazolilo, isoquinolinilo, dihidrobencisotiazol-1,1-dionilo o pirrolopiridilo. En algunas de dichas realizaciones, R1 está sustituido con uno o más de alquilo C1-4 sustituido o sin sustituir, heterociclilo sustituido o sin sustituir, halógeno, hidroxilo, hidroxialquilo, alcoxi, -CN, -OR, -NR2, -(alquil C14)NR2, -C(=O)NR2 o -C(O)R, en donde cada R es independientemente -H, un alquilo C1-6 sustituido o sin sustituir, un heterociclilo sustituido o sin sustituir o un heterociclilalquilo sustituido o sin sustituir.
En algunas de dichas realizaciones, R1 es
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En algunas realizaciones, R' es -H, -CH3, -CH2CH3, isopropilo, -(CH2)2OH, -(CH2)2NH2 o -(CH2)2OCH3. En otras realizaciones, R" es -F, -CH3, -CH2CH3, isopropilo, -NH(alquil C1-3)NH2, -NH(CH2)2OH, -CF3, -OH, -OCH3, O(CH2)2OCH3, -O(CH2)2OH, -O(CH2)2NH2, -O(CH2)2pirrolidilo, -CH2OH, -(CH2)2OH, -CH2OCH3, -(CH2)2OCH3, -CH2NH2, -CH2NHCH3, -CH2N(CH3)2, -C(CH3)2OH, -CN, -NH2, -NHCH3, -N(CH3)2, -NH(CH2)2NH2, -C(=O)NH2, C(=O)NHCH3, -NH(CH2)2pirrolidilo, -NH(piperidilo sustituido o sin sustituir), piperidilo sustituido o sin sustituir, NH(tetrahidropiranilo sustituido o sin sustituir) o morfolinilo sustituido o sin sustituir.
En algunas realizaciones, el compuesto de heteroarilo es un compuesto de fórmula (I), en donde R2 es un alquilo C16 sustituido o sin sustituir. Por ejemplo, en ciertas realizaciones, R2 es metilo, etilo, n-propilo, isopropilo, n-butilo, secbutilo, isobutilo o terc-butilo, opcionalmente sustituido con uno o más de -OH, -C(O)NH2, -NH2, alquilamino, NHCH2C(=O)NH2, ciclopentilo, ciclopentanol, ciclohexilo, ciclohexanol o 1-metilciclohexanol-4-ilo. En algunas realizaciones, R2 es un cicloalquilo sustituido o sin sustituir, por ejemplo, R2 es ciclohexilo. En otras realizaciones, R2 es un heterociclilalquilo sustituido o sin sustituir, por ejemplo, -CH2-azetidinilo, -CH2-piperidilo, -CH2-piridin-2(1H)onilo, -CH2-piridilo, -CH2-piperazin-2-onilo, -CH2-piperazin-2,6-dionilo, -CH2-piperazinilo, -CH2-pirrolidilo, -CH2-1,4dioxanilo, -CH2-piperidin-2,6-dionilo, -CH2-imidazolidinilo, -CH2-imidazolidin-4-onilo, -CH2-morfolinilo, -CH2tetrahidropirimidin-2(1H)-onilo, -CH2-1,4-diazepan-5-onilo, -CH2-tetrahidro-2H-piranilo o -CH2-imidazolidin-2,4-dionilo; en donde el heterociclilalquilo está opcionalmente sustituido con uno o más de metilo, etilo, isopropilo, halógeno, -OH, -(CH2)OH o -C(=O)NH2. Por ejemplo, en algunas realizaciones, R2 es -CF2-(tetrahidro-2H-piran-4-ilo) o -CF2(1,4-dioxan-2-ilo).
En algunas realizaciones, el compuesto de heteroarilo es un compuesto de fórmula (I), en donde R2 es -NR3R4. Por ejemplo, en ciertas realizaciones, R2 es -NH(alquilo C1-6), -N(alquilo C1-6)2, -N(alquil C1-6)(cicloalquilo), -NH(arilo), NH(heteroarilo), -NH(cicloalquilo), -NH(cicloalquilalquilo), -NH(heterociclilo), -N(alquil C1-6)(heterociclilo) o NH(heterociclilalquilo), en donde cada alquilo, arilo, heteroarilo, cicloalquilo, cicloalquilalquilo, heterociclilo y heterociclilalquilo está independientemente sustituido o sin sustituir. En algunas realizaciones, R2 es -NH(metilo), N(metilo)2, -N(metil)(etilo), -NH(etilo), -NH(propilo), -NH(isopropilo), -NH(ciclopentilo), -NH(ciclohexilo), N(ciclohexil)(metilo), -NHCH2(ciclopentilo), -NHCH2(ciclohexilo), -NH(fenilo), -NH(piridilo), -NH(piperidilo), NH(tetrahidro-2H-piranilo), -N(metil)(tetrahidro-2H-piranilo), -NH(azepanilo), -NH(tetrahidrofuranilo), N(metil)(tetrahidrofuranilo), -NH(pirrolidilo) o -NHCH2(tetrahidro-2H-piranilo), en donde cada metilo, etilo, propilo, isopropilo, ciclopentilo, ciclohexilo, fenilo, piridilo, piperidilo, pirrolidilo, tetrahidro-2H-piranilo, azepanilo o tetrahidrofuranilo está independientemente sustituido o sin sustituir. En algunas de dichas realizaciones, el metilo, etilo, propilo, isopropilo, ciclopentilo, ciclohexilo, fenilo, piridilo, piperidilo, pirrolidilo, tetrahidro-2H-piranilo, azepanilo
o tetrahidrofuranilo, está sustituido con uno o más de fenilo, alquilo C1-4, hidroxialquilo, -NR2, -OR o -C(=O)NR2, en donde cada R es independientemente -H, un alquilo C1-6 sustituido o sin sustituir, un heterociclilo sustituido o sin sustituir o un heterociclilalquilo sustituido o sin sustituir.
En algunas realizaciones, el compuesto de heteroarilo es un compuesto de fórmula (I), en donde R2 es -NHC(=O)R3, en donde R3 es un alquilo C1-4 sustituido o sin sustituir. En otras, R2 es -C(=O)NR3R4, y R3 y R4 son
12
independientemente -H o un alquilo C1-4 sustituido o sin sustituir, o un heterociclilo sustituido o sin sustituir. En otras más, R2 es -OR3. En algunas de dichas realizaciones, R3 es ciclohexilo, metilo, etilo, propilo, piperidilo, tetrahidro-2Hpiranilo, tetrahidrofuranilo, -CH2(pirrolidilo) o fenilo, opcionalmente sustituido con uno o más de -OH, -NH2, o (C=O)NH2. En otras realizaciones más, R2 es -C(=O)R5. Por ejemplo, en ciertas realizaciones, R5 es fenilo.
5 En algunas realizaciones, el compuesto de heteroarilo es un compuesto de fórmula (I), en donde R2 es -(CH2)02CR6(OR3)R4. Por ejemplo, en ciertas realizaciones, R2 es -CH(OR3)R4. En algunas de dichas realizaciones, R3 es -H y R4 es fenilo, piperidilo, piridilo, pirimidin-4(3H)-onilo o tetrahidrofuranilo. En algunas otras realizaciones, R3 es -H y R4 y R6, junto con los átomos a los que están unidos, forman un grupo piperidilo.
En algunas realizaciones, el compuesto de heteroarilo es un compuesto de fórmula (I), en donde R2 es un
10 heterociclilo sustituido o sin sustituir seleccionado de 1,2,3,6-tetrahidropiridilo, bencisoxazolilo o isoindolin-1-onilo. En algunas de dichas realizaciones, R2 está sustituido con uno o más de alquilo C1-4 sustituido o sin sustituir, heterociclilalquilo sustituido o sin sustituir, hidroxilo, -OR, -NR2, o -C(=O)NR2, en donde cada R es independientemente -H, un alquilo C1-6 sustituido o sin sustituir, un heterociclilo sustituido o sin sustituir, o un heterociclilalquilo sustituido o sin sustituir.
15 En algunas realizaciones, R2 es
en donde R' es -H, o un alquilo C1-6 sustituido o sin sustituir; cada R" es independientemente un alquilo C1-4 sustituido o sin sustituir, un heterociclilo sustituido o sin sustituir, un heterociclilalquilo sustituido o sin sustituir,
20 hidroxilo, halógeno, alcoxi, -CN, -OR, -NR2, -(alquil C1-4)NR2, -C(=O)NR2, en donde cada R es independientemente -H, un alquilo C1-6 sustituido o sin sustituir, un heterociclilo sustituido o sin sustituir o un heterociclilalquilo sustituido o sin sustituir; y n = 0-2. Por ejemplo, en ciertas realizaciones, R" es -CH3, -CH2CH3, isopropilo, -CH2OH, -CH2OCH3, -CH(CH3)OH, -(CH2)2NH2, -CH2NHCH3, -CH2N(CH3)2, -OH, -OCH3, -O(CH2)2NH2, -NH2, -NHCH3, -N(CH3)2, -NH(CH2)2OH, -NH(CH2)2NH2, -C(=O)NH2, -CH2(pirrolidilo) o piperazinilo sustituido o sin sustituir.
25 Se entenderá por los expertos en la técnica que cualquiera de los sustituyentes R" puede estar unido a cualquier átomo adecuado de cualquiera de los anillos en los sistemas de anillos condensados. Por ejemplo, en algunas realizaciones, R2 es -(alquilo C1-4), -(alquil C1-4)OH,
13
en donde R' es –H, o un alquilo C1-6 sustituido o sin sustituir; cada R" es independientemente un alquilo C1-4 sustituido o sin sustituir, un heterociclilo sustituido o sin sustituir, un heterociclilalquilo sustituido o sin sustituir, hidroxilo, halógeno, alcoxi, -CN, -OR, -NR2, -(alquil C1-4)NR2, -C(=O)NR2, en donde cada R es independientemente -H, un alquilo C1-6 sustituido o sin sustituir, un heterociclilo sustituido o sin sustituir o un heterociclilalquilo sustituido o sin sustituir; y X = CH2, CF2 o NR'.
En ciertas realizaciones, los compuestos de heteroarilo tienen un grupo R1 expuesto en la presente memoria y un grupo R2 expuesto en la presente memoria. En algunas de dichas realizaciones donde R2 es como se describe en la presente memoria, R1 es
14
(1R,2R)-2-(2-(4-(trifluorometil)fenilamino)-[1,2,4]triazolo[1,5-a]piridin-5-ilamino)ciclopentanol; cis-4-(2-(2-metoxipiridin-4-ilamino)-[1,2,4]triazolo[1,5-a]piridin-5-ilamino)ciclohexanol; 2-(6-(2-(4-(trifluorometil)fenilamino)-[1,2,4]triazolo[1,5-a]piridin-5-il)-1H-benzo[d]imidazol-2-il)propan-2-ol; 5-(1H-imidazo[4,5-b]piridin-6-il)-N-(4-(trifluorometil)fenil)-[1,2,4]triazolo[1,5-a]piridin-2-amina;
5 cis-5-(5-(4-hidroxiciclohexilamino)-[1,2,4]triazolo[1,5-a]piridin-2-ilamino)picolinonitrilo; cis-4-((2-(4-(trifluorometil)fenilamino)-[1,2,4]triazolo[1,5-a]piridin-5-ilamino)metil)ciclohexanol; trans-1-metil-4-(2-(4-(trifluorometil)fenilamino)-[1,2,4]triazolo[1,5-a]piridin-5-ilamino)ciclohexanol; cis-1-metil-4-(2-(4-(trifluorometil)fenilamino)-[1,2,4]triazolo[1,5-a]piridin-5-ilamino)ciclohexanol; cis-2-(4-(2-(4-(trifluorometil)fenilamino)-[1,2,4]triazolo[1,5-a]piridin-5-ilamino)ciclohexil)propan-2-ol;
10 cis-4-(5-(4-hidroxiciclohexilamino)-[1,2,4]triazolo[1,5-a]piridin-2-ilamino)-N-metilbenzamida; trans-4-(5-(4-hidroxiciclohexilamino)-[1,2,4]triazolo[1,5-a]piridin-2-ilamino)-N-metilbenzamida; 4-((2-(4-(trifluorometil)fenilamino)-[1,2,4]triazolo[1,5-a]piridin-5-il)metil)piperazin-2-ona; cis-4-(2-(piridin-4-ilamino)-[1,2,4]triazolo[1,5-a]piridin-5-ilamino)ciclohexanol; cis-4-(2-(5-metilpiridin-3-ilamino)-[1,2,4]triazolo[1,5-a]piridin-5-ilamino)ciclohexanol;
15 cis-4-(2-(6-metoxipiridin-3-ilamino)-[1,2,4]triazolo[1,5-a]piridin-5-ilamino)ciclohexanol; cis-4-(2-(6-(dimetilamino)piridin-3-ilamino)-[1,2,4]triazolo[1,5-a]piridin-5-ilamino)ciclohexanol; 5-(piperazin-1-ilmetil)-N-(4-(trifluorometil)fenil)-[1,2,4]triazolo[1,5-a]piridin-2-amina; trans-4-(5-(4-aminociclohexilamino)-[1,2,4]triazolo[1,5-a]piridin-2-ilamino)-N-metilbenzamida; 5-(piperidin-4-ilmetil)-N-(4-(trifluorometil)fenil)-[1,2,4]triazolo[1,5-a]piridin-2-amina;
20 1-((2-(4-(trifluorometil)fenilamino)-[1,2,4]triazolo[1,5-a]piridin-5-il)metil)piperidin-4-ol; trans-2-(4-(2-(4-(trifluorometil)fenilamino)-[1,2,4]triazolo[1,5-a]piridin-5-ilamino)ciclohexil)propan-2-ol; trans-4-((2-(4-(trifluorometil)fenilamino)-[1,2,4]triazolo[1,5-a]piridin-5-il)metil)ciclohexanol; cis-4-((2-(4-(trifluorometil)fenilamino)-[1,2,4]triazolo[1,5-a]piridin-5-il)metil)ciclohexanol; 4-(5-(ciclopentilamino)-[1,2,4]triazolo[1,5-a]piridin-2-ilamino)-N-metilbenzamida;
25 5-(2-(metoximetil)-1H-benzo[d]imidazol-6-il)-N-(4-(trifluorometil)fenil)-[1,2,4]triazolo[1,5-a]piridin-2-amina; 1-(6-(2-(4-(trifluorometil)fenilamino)-[1,2,4]triazolo[1,5-a]piridin-5-il)-1H-benzo[d]imidazol-2-il)etanol; cis-4-(2-(6-metilpiridin-3-ilamino)-[1,2,4]triazolo[1,5-a]piridin-5-ilamino)ciclohexanol; (S)-N2-(2-(2-aminoetoxi)piridin-4-il)-N5-(piperidin-3-il)-[1,2,4]triazolo[1,5-a]piridin-2,5-diamina; trans-4-(2-(4-(trifluorometil)fenilamino)-[1,2,4]triazolo[1,5-a]piridin-5-iloxi)ciclohexanocarboxamida;
30 (1R,2S)-2-(2-(4-(trifluorometil)fenilamino)-[1,2,4]triazolo[1,5-a]piridin-5-ilamino)ciclopentanol; 5-((1-etilpiperidin-4-il)metil)-N-(4-(trifluorometil)fenil)-[1,2,4]triazolo[1,5-a]piridin-2-amina; 6-(2-(4-(trifluorometil)fenilamino)-[1,2,4]triazolo[1,5-a]piridin-5-il)-1H-benzo[d]imidazol-2-carboxamida; (6-(2-(4-(trifluorometil)fenilamino)-[1,2,4]triazolo[1,5-a]piridin-5-il)-1H-benzo[d]imidazol-2-il)metanol; cis-(4-(2-(4-(trifluorometil)fenilamino)-[1,2,4]triazolo[1,5-a]piridin-5-ilamino)ciclohexil)metanol;
35 (S)-N2-(6-morfolinopiridin-3-il)-N5-(piperidin-3-il)-[1,2,4]triazolo[1,5-a]piridin-2,5-diamina; (R)-2-fenil-2-(2-(4-(trifluorometil)fenilamino)-[1,2,4]triazolo[1,5-a]piridin-5-ilamino)etanol; (S)-2-fenil-2-(2-(4-(trifluorometil)fenilamino)-[1,2,4]triazolo[1,5-a]piridin-5-ilamino)etanol;
23
TABLA 1.
Claims (2)
-
imagen1 imagen2 imagen3 imagen4 imagen5 imagen6 3,3,4-trimetil-6-(5-((tetrahidro-2H-piran-4-il)metil)-[1,2,4]triazolo[1,5-a]piridin-2-ilamino)indolin-2-ona; 4-((2-(2-(metoximetil)-1H-benzo[d]imidazol-6-ilamino)-[1,2,4]triazolo[1,5-a]piridin-5-il)metil)piridin-2-ol; N-(2-(metoximetil)-1H-benzo[d]imidazol-6-il)-5-((tetrahidro-2H-piran-4-il)metil)-[1,2,4]triazolo[1,5-a]piridin-2-amina; (S)-3,3-dimetil-6-(5-(tetrahidrofuran-3-iloxi)-[1,2,4]triazolo[1,5-a]piridin-2-ilamino)indolin-2-ona; (R)-3,3-dimetil-6-(5-(tetrahidrofuran-3-iloxi)-[1,2,4]triazolo[1,5-a]piridin-2-ilamino)indolin-2-ona; 1,3,3-trimetil-6-(5-((3-oxopiperazin-1-il)metil)-[1,2,4]triazolo[1,5-a]piridin-2-ilamino)indolin-2-ona; 3,3-dimetil-6-(5-(piperidin-4-ilmetil)-[1,2,4]triazolo[1,5-a]piridin-2-ilamino)indolin-2-ona; cis-6-(5-((4-hidroxi-4-metilciclohexil)metil)-[1,2,4]triazolo[1,5-a]piridin-2-ilamino)-3,3-dimetilindolin-2-ona; trans-6-(5-((4-hidroxi-4-metilciclohexil)metil)-[1,2,4]triazolo[1,5-a]piridin-2-ilamino)-3,3-dimetilindolin-2-ona; 1,3,3-trimetil-6-(5-((tetrahidro-2H-piran-4-il)metil)-[1,2,4]triazolo[1,5-a]piridin-2-ilamino)indolin-2-ona; 2-metil-5-(5-((tetrahidro-2H-piran-4-il)metil)-[1,2,4]triazolo[1,5-a]piridin-2-ilamino)isoindolin-1-ona; N-(1,4-dimetil-1H-indazol-6-il)-5-((tetrahidro-2H-piran-4-il)metil)-[1,2,4]triazolo[1,5-a]piridin-2-amina; 4-((2-(3-(trifluorometil)-1H-indazol-6-ilamino)-[1,2,4]triazolo[1,5-a]piridin-5-il)metil)piperazin-2-ona; 3,3-dimetil-6-(5-((2-oxo-1,2-dihidropiridin-4-il)metil)-[1,2,4]triazolo[1,5-a]piridin-2-ilamino)indolin-2-ona; 5-(5-((2-hidroxipiridin-4-il)metil)-[1,2,4]triazolo[1,5-a]piridin-2-ilamino)isoindolin-1-ona; 3,3-dimetil-6-(5-(1-(tetrahidro-2H-piran-4-il)etil)-[1,2,4]triazolo[1,5-a]piridin-2-ilamino)indolin-2-ona; N-(1-metil-1H-indazol-6-il)-5-((tetrahidro-2H-piran-4-il)metil)-[1,2,4]triazolo[1,5-a]piridin-2-amina; (±)-cis-4-(2-(3-metil-1H-indazol-6-ilamino)-[1,2,4]triazolo[1,5-a]piridin-5-iloxi)tetrahidrofuran-3-ol; 3,3-dimetil-6-(5-(tetrahidro-2H-piran-4-iloxi)-[1,2,4]triazolo[1,5-a]piridin-2-ilamino)indolin-2-ona; 3-metil-1-((2-(3-metil-1H-indazol-6-ilamino)-[1,2,4]triazolo[1,5-a]piridin-5-il)metil)azetidin-3-ol; 3,3-dimetil-6-(5-((3-oxopiperazin-1-ilmetil))-[1,2,4]triazolo[1,5-a]piridin-2-ilamino)indolin-2-ona; 6-(5-(hidroxi(tetrahidro-2H-piran-4-il)metil)-[1,2,4]triazolo[1,5-a]piridin-2-ilamino)-3,3-dimetilindolin-2-ona; 3,3-dimetil-6-(5-((tetrahidro-2H-piran-4-il)metil)-[1,2,4]triazolo[1,5-a]piridin-2-ilamino)indolin-2-ona; 4-((2-(3-metil-1H-indazol-6-ilamino)-[1,2,4]triazolo[1,5-a]piridin-5-il)metil)piridin-2(1H)ona; 5-((3,3-difluoropiperidin-1-il)metil)-N-(3-metil-1H-indazol-6-il)-[1,2,4]triazolo[1,5-a]piridin-2-amina; 2-((2-(3-metil-1H-indazol-6-ilamino)-[1,2,4]triazolo[1,5-a]piridin-5-il)metilamino)acetamida; cis-1-(metoximetil)-4-((2-(4-(trifluorometil)fenilamino)-[1,2,4]triazolo[1,5-a]piridin-5-il)metil)ciclohexanol; 4-((2-(1-isopropil-1H-indazol-6-ilamino)-[1,2,4]triazolo[1,5-a]piridin-5-il)metil)piperazin-2-ona; 6-(hidroxi(2-(4-(trifluorometil)fenilamino)-[1,2,4]triazolo[1,5-a]piridin-5-il)metil)pirimidin-4(3H)-ona; N-(3-metil-1H-indazol-6-il)-5-((tetrahidro-2H-piran-4-il)metil)-[1,2,4]triazolo[1,5-a]piridin-2-amina; (2-(3-metil-1H-indazol-6-ilamino)-[1,2,4]triazolo[1,5-a]piridin-5-il)(tetrahidro-2H-piran-4-il)metanol; (R)-3-((2-(4-(trifluorometil)fenilamino)-[1,2,4]triazolo[1,5-a]piridin-5-il)metilamino)pirrolidin-2-ona; (±)-3-((2-(4-(trifluorometil)fenilamino)-[1,2,4]triazolo[1,5-a]piridin-5-il)metilamino)pirrolidin-2-ona; 4-((2-(3-amino-1H-indazol-6-ilamino)-[1,2,4]triazolo[1,5-a]piridin-5-il)metil)ciclohexanol; 4-(1-(2-(4-(trifluorometil)fenilamino)-[1,2,4]triazolo[1,5-a]piridin-5-il)ctil)piridin-2(1H)-ona; N-metil-2-((2-(4-(trifluorometil)fenilamino)-[1,2,4]triazolo[1,5-a]piridin-5-il)metilamino)acetamida; 4-(5-((3-hidroxiciclopentil)metil)-[1,2,4]triazolo[1,5-a]piridin-2-ilamino)-N-metilbenzamida (diastereómero 2);3354-((2-(4-fluoro-3-metilfenilamino)-[1,2,4]triazolo[1,5-a]piridin-5-il)metil)piridin-2-ol; 4-((2-(6-(4-hidroxipiperidin-1-il)piridin-3-ilamino)-[1,2,4]triazolo[1,5-a]piridin-5-il)metil)piperazin-2-ona; (S)-2-((2-(4-(trifluorometil)fenilamino)-[1,2,4]triazolo[1,5-a]piridin-5-il)metilamino)propanamida; 4-((2-(4-fluoro-3-metilfenilamino)-[1,2,4]triazolo[1,5-a]piridin-5-il)metil)piperazin-2-ona; 4-((2-(1H-pirrolo[2,3-b]piridin-5-ilamino)-[1,2,4]triazolo[1,5-a]piridin-5-il)metil)piperazin-2-ona; (±)-5-isopropil-4-((2-(4-(trifluorometil)fenilamino)-[1,2,4]triazolo[1,5-a]piridin-5-il)metil)piperazin-2-ona; 4-(5-((3-hidroxiciclopentil)metil)-[1,2,4]triazolo[1,5-a]piridin-2-ilamino)-N-metilbenzamida (diastereómero1); (±)-2-((2-(4-(trifluorometil)fenilamino)-[1,2,4]triazolo[1,5-a]piridin-5-il)metilamino)propanamida; 1-(3-metil-1H-indazol-6-il)-4-((2-(3-metil-1H-indazol-6-ilamino)-[1,2,4]triazolo[1,5-a]piridin-5-il)metil)piperazin-2ona; 4-((2-(3-metil-1H-indazol-6-ilamino)-[1,2,4]triazolo[1,5-a]piridin-5-il)metil)piperazin-2-ona; cis-4-((2-(3-metil-1H-indazol-6-ilamino)-[1,2,4]triazolo[1,5-a]piridin-5-il)metil)ciclohexanol; trans-4-((2-(3-metil-1H-indazol-6-ilamino)-[1,2,4]triazolo[1,5-a]piridin-5-il)metil)ciclohexanol; 1-((2-(4-(trifluorometil)fenilamino)-[1,2,4]triazolo[1,5-a]piridin-5-il)metil)imidazolidin-2,4-diona; N-metil-4-(5-(2-(piperidin-4-il)etil)-[1,2,4]triazolo[1,5-a]piridin-2-ilamino)benzamida; 1-((2-(4-(trifluorometil)fenilamino)-[1,2,4]triazolo[1,5-a]piridin-5-il)metil)piperidin-3-carboxamida; 5-metil-4-((2-(4-(trifluorometil)fenilamino)-[1,2,4]triazolo[1,5-a]piridin-5-il)metil)piperazin-2-ona; 4-(5-((4-aminociclohexil)metil)-[1,2,4]triazolo[1,5-a]piridin-2-ilamino)-N-metilbenzamida; 4-(1-(2-(4-(trifluorometil)fenilamino)-[1,2,4]triazolo[1,5-a]piridin-5-il)etil)piperazin-2-ona; 4-((2-(4-(trifluorometil)fenilamino)-[1,2,4]triazolo[1,5-a]piridin-5-il)metil)piperazin-2,6-diona; N-metil-4-(5-(pirrolidin-3-ilmetil)-[1,2,4]triazolo[1,5-a]piridin-2-ilamino)benzamida; 1-((2-(4-(trifluorometil)fenilamino)-[1,2,4]triazolo[1,5-a]piridin-5-il)metil)-1,4-diazepan-5-ona; (S)-(1-((2-(4-(trifluorometil)fenilamino)-[1,2,4]triazolo[1,5-a]piridin-5-il)metil)pirrolidin-2-il)metanol; (R)-(1-((2-(4-(trifluorometil)fenilamino)-[1,2,4]triazolo[1,5-a]piridin-5-il)metil)pirrolidin-2-il)metanol; (1-((2-(4-(trifluorometil)fenilamino)-[1,2,4]triazolo[1,5-a]piridin-5-il)metil)piperidin-3-il)metanol; (1-((2-(4-(trifluorometil)fenilamino)-[1,2,4]triazolo[1,5-a]piridin-5-il)metil)piperidin-4-il)metanol; (S)-3-Metil-4-((2-(4-(trifluorometil)fenilamino)-[1,2,4]triazolo[1,5-a]piridin-5-il)metil)piperazin-2-ona; N-metil-4-(5-(piperidin-4-ilmetil)-[1,2,4]triazolo[1,5-a]piridin-2-ilamino)benzamida; 3-metil-4-((2-(4-(trifluorometil)fenilamino)-[1,2,4]triazolo[1,5-a]piridin-5-il)metil)piperazin-2-ona; 6-metil-4-((2-(4-(trifluorometil)fenilamino)-[1,2,4]triazolo[1,5-a]piridin-5-il)metil)piperazin-2-ona; cis-4-(5-(4-aminociclohexiloxi)-[1,2,4]triazolo[1,5-a]piridin-2-ilamino)-N-metilbenzamida; N-metil-4-(5-(piperidin-4-iloxi)-[1,2,4]triazolo[1,5-a]piridin-2-ilamino)benzamida; 1-((2-(4-(trifluorometil)fenilamino)-[1,2,4]triazolo[1,5-a]piridin-5-il)metil)tetrahidropirimidin-2(1H)-ona; 2-((2-(4-(trifluorometil)fenilamino)-[1,2,4]triazolo[1,5-a]piridin-5-il)metilamino)acetamida; trans-4-(5-(4-aminociclohexiloxi)-[1,2,4]triazolo[1,5-a]piridin-2-ilamino)-N-metilbenzamida; 4-(5-(3-hidroxibencil)-[1,2,4]triazolo[1,5-a]piridin-2-ilamino)-N-metilbenzamida; 5-(2-aminoetoxi)-N-(4-(trifluorometil)fenil)-[1,2,4]triazolo[1,5-a]piridin-2-amina;336imagen7 imagen8 imagen9 (R)-3,3-dimetil-6-(5-(tetrahidrofuran-3-ilamino)-[1,2,4]triazolo[1,5-a]piridin-2-ilamino)indolin-2-ona; 1,3,3-trimetil-6-(5-(tetrahidro-2H-piran-4-ilamino)-[1,2,4]triazolo[1,5-a]piridin-2-ilamino)indolin-2-ona; cis-6-(5-(4-hidroxiciclohexilamino)-[1,2,4]triazolo[1,5-a]piridin-2-ilamino)-1,3,3-trimetilindolin-2-ona; 6-(5-((2-hidroxietil)(metil)amino)-[1,2,4]triazolo[1,5-a]piridin-2-ilamino)-3,3-dimetilindolin-2-ona; (S)-3,3-Dimetil-6-(5-(piperidin-3-ilamino)-[1,2,4]triazolo[1,5-a]piridin-2-ilamino)indolin-2-ona; 3,3-dimetil6-(5-(metil(tetrahidro-2H-piran-4-il)amino)-[1,2,4]triazolo[1,5-a]piridin-2-ilamino)indolin-2-ona; N2-(1-metil-1H-indazol-6-il)-N5-(tetrahidro-2H-piran-4-il)-[1,2,4]triazolo[1,5-a]piridin-2,5-diamina; trans-6-(5-(4-hidroxi-4-metilciclohexilamino)-[1,2,4]triazolo[1,5-a]piridin-2-ilamino)-3,3-dimetilindolin-2-ona; cis-6-(5-(4-hidroxi-4-metilciclohexilamino)-[1,2,4]triazolo[1,5-a]piridin-2-ilamino)-3,3-dimetilindolin-2-ona; cis-4-(2-(4-fluoro-3-metil-1H-indazol-6-ilamino)-[1,2,4]triazolo[1,5-a]piridin-5-ilamino)ciclohexanol; (±)-trans-4-(2-(3-metil-1H-indazol-6-ilamino)-[1,2,4]triazolo[1,5-a]piridin-5-ilamino)tetrahidrofurano-3-ol; (R)-N2-(3-metil-1H-indazol-6-il)-N5-(tetrahidrofurano-3-il)-[1,2,4]triazolo[1,5-a]piridin-diamina; 2,5-cis-5-(5-(4-hidroxiciclohexilamino)-[1,2,4]triazolo[1,5-a]piridin-2-ilamino)-2-(2-metoxietil)isoindolin-1-ona; trans-6-(5-(4-hidroxiciclohexilamino)-[1,2,4]triazolo[1,5-a]piridin-2-ilamino)-3,3-dimetilindolin-2-ona; 3,3-dimetil-6-(5-(tetrahidro-2H-piran-4-ilamino)-[1,2,4]triazolo[1,5-a]piridin-2-ilamino)indolin-2-ona; (1S,3R)-3-((2-(3-metil-1H-indazol-6-ilamino)-[1,2,4]triazolo[1,5-a]piridin-5-ilamino)metil)ciclopentanol; (1R,3R)-3-((2-(3-metil-1H-indazol-6-ilamino)-[1,2,4]triazolo[1,5-a]piridin-5-ilamino)metil)ciclopentanol; (1R,3S)-3-((2-(3-metil-1H-indazol-6-ilamino)-[1,2,4]triazolo[1,5-a]piridin-5-ilamino)metil)ciclopentanol; (1S,3S)-3-((2-(3-metil-1H-indazol-6-ilamino)-[1,2,4]triazolo[1,5-a]piridin-5-ilamino)metil)ciclopentanol; (S)-N2-(3-metil-1H-indazol-6-il)-N5-(tetrahidrofurano-3-il)-[1,2,4]triazolo[1,5-a]piridin-2,5-diamina; cis-6-(5-(4-hidroxiciclohexilamino)-[1,2,4]triazolo[1,5-a]piridin-2-ilamino)-1-(2-hidroxietil)indolin-2-ona; N5-metil-N2-(3-metil-1H-indazol-6-il)-N5-(tetrahidro-2H-piran-4-il)-[1,2,4]triazolo[1,5-a]piridin-2,5-diamina; 2-(metil(2-(3-metil-1H-indazol-6-ilamino)-[1,2,4]triazolo[1,5-a]piridin-5-il)amino)etanol; cis-4-(2-(1-(2-hidroxietil)-3-metil-1H-indazol-6-ilamino)-[1,2,4]triazolo[1,5-a]piridin-5-ilamino)ciclohexanol; cis-6-(5-(4-hidroxiciclohexilamino)-[1,2,4]triazolo[1,5-a]piridin-2-ilamino)-1-metilindolin-2-ona; cis-4-(2-(1-(2-metoxietil)-3-metil-1H-indazol-6-ilamino)-[1,2,4]triazolo[1,5-a]piridin-5-ilamino)ciclohexanol; cis-4-(2-(2-(hidroximetil)-1H-benzo[d]imidazol-6-ilamino)-[1,2,4]triazolo[1,5-a]piridin-5-ilamino)ciclohexanol; cis-4-(2-(2-(metoximetil)-1H-benzo[d]imidazol-6-ilamino)-[1,2,4]triazolo[1,5-a]piridin-5-ilamino)ciclohexanol; cis-4-(2-(1-etil-3-metil-1H-indazol-6-ilamino)-[1,2,4]triazolo[1,5-a]piridin-5-ilamino)ciclohexanol; cis-5-(5-(4-hidroxiciclohexilamino)-[1,2,4]triazolo[1,5-a]piridin-2-ilamino)-2-(2-hidroxietil)isoindolin-1-ona; trans-4-(2-(3-metil-1H-indazol-6-ilamino)-[1,2,4]triazolo[1,5-a]piridin-5-ilamino)ciclohexanol; cis-6-(5-(4-hidroxiciclohexilamino)-[1,2,4]triazolo[1,5-a]piridin-2-ilamino)-3,3-dimetilindolin-2-ona; cis-6-(5-(4-hidroxiciclohexilamino)-[1,2,4]triazolo[1,5-a]piridin-2-ilamino)-3,4-dihidroisoquinolin-1(2H)-ona; cis-4-(2-(4-metil-1H-indazol-6-ilamino)-[1,2,4]triazolo[1,5-a]piridin-5-ilamino)ciclohexanol; cis-6-(5-(4-hidroxiciclohexilamino)-[1,2,4]triazolo[1,5-a]piridin-2-ilamino)-2-(2-hidroxietil)isoindolin-1-ona; N2-(3-metil-1H-indazol-6-il)-N5-(tetrahidro-2H-piran-4-il)-[1,2,4]triazolo[1,5-a]piridin-2,5-diamina; cis-4-(2-(4-fluoro-3-(2-metoxietoxi)fenilamino)-[1,2,4]triazolo[1,5-a]piridin-5-ilamino)ciclohexanol;340imagen10 imagen11 imagen12 imagen13 6-(5-(isopropilamino)-[1,2,4]triazolo[1,5-a]piridin-2-ilamino)-3,3-dimetilindolin-2-ona; N2-(1-metil-1H-indazol-5-il)-N5-(tetrahidro-2H-piran-4-il)-[1,2,4]triazolo[1,5-a]piridin-2,5-diamina; cis-4-(2-(1H-pirazolo[4,3-b]piridin-6-ilamino)-[1,2,4]triazolo[1,5-a]piridin-5-ilamino)ciclohexanol; cis-4-(5-(4-hidroxiciclohexilamino)-[1,2,4]triazolo[1,5-a]piridin-2-ilamino)-1,6-dimetilindolin-2-ona; cis-6-(5-(4-hidroxiciclohexilamino)-[1,2,4]triazolo[1,5-a]piridin-2-ilamino)-1,4-dimetilindolin-2-ona; 4-(5-(ciclohexilamino)-[1,2,4]triazolo[1,5-a]piridin-2-ilamino)benzamida; N2-(4-(1H-1,2,4-triazol-3-il)fenil)-N5-(tetrahidro-2H-piran-4-il)-[1,2,4]triazolo[1,5-a]piridin-2,5-diamina; 6-(5-(dimetilamino)-[1,2,4]triazolo[1,5-a]piridin-2-ilamino)-3,3-dimetilindolin-2-ona; cis-4-(2-(4-(1H-1,2,4-triazol-3-il)fenilamino)-[1,2,4]triazolo[1,5-a]piridin-5-ilamino)ciclohexanol; cis-4-(2-(3-metil-[1,2,4]triazolo[4,3-a]piridin-7-ilamino)-[1,2,4]triazolo[1,5-a]piridin-5-ilamino)ciclohexanol; 1-metil-5-(5-(tetrahidro-2H-piran-4-ilamino)-[1,2,4]triazolo[1,5-a]piridin-2-ilamino)-1H-benzo[d]imidazol-2(3H)ona;o cis-5-(5-(4-hidroxiciclohexilamino)-[1,2,4]triazolo[1,5-a]piridin-2-ilamino)-1-metil-1H-benzo[d]imidazol-2(3H)ona. - 14. Un compuesto o una sal, tautómero, estereoisómero o solvato farmacéuticamente aceptable del mismo, en donde el compuesto es N-metil-4-(5-(2-metil-1H-benzo[d]imidazol-6-il)-[1,2,4]triazolo[1,5-a]piridin-2-ilamino)benzamida; 5-(5-(2-(hidroximetil)-1H-benzo[d]imidazol-6-il)-[1,2,4]triazolo[1,5-a]piridin-2-ilamino)piridin-2-ol; (6-(2-(6-metoxipiridin-3-ilamino)-[1,2,4]triazolo[1,5-a]piridin-5-il)-1H-benzo[d]imidazol-2-il)metanol; (6-(2-(6-metilpiridin-3-ilamino)-[1,2,4]triazolo[1,5-a]piridin-5-il)-1H-benzo[d]imidazol-2-il)metanol; (6-(2-(6-(dimetilamino)piridin-3-ilamino)-[1,2,4]triazolo[1,5-a]piridin-5-il)-1H-benzo[d]imidazol-2-il)metanol; 2-(6-(2-(4-(trifluorometil)fenilamino)-[1,2,4]triazolo[1,5-a]piridin-5-il)-1H-benzo[d]imidazol-2-il)propan-2-ol; 5-(2-(metoximetil)-1H-benzo[d]imidazol-6-il)-N-(4-(trifluorometil)fenil)-[1,2,4]triazolo[1,5a]piridin-2-amina; 1-(6-(2-(4-(trifluorometil)fenilamino)-[1,2,4]triazolo[1,5-a]piridin-5-il)-1H-benzo[d]imidazol-2-il)etanol; 6-(2-(4-(trifluorometil)fenilamino)-[1,2,4]triazolo[1,5-a]piridin-5-il)1H-benzo[d]imidazol-2-carboxamida; (6-(2-(4-(trifluorometil)fenilamino)-[1,2,4]triazolo[1,5-a]piridin-5-il)-1H-benzo[d]imidazol-2-il)metanol; 5-(2-((metilamino)metil)benzo[d]oxazol-6-il)-N-fenil-[1,2,4]triazolo[1,5-a]piridin-2-amina; 4-(5-(1H-indazol-5-il)-[1,2,4]triazolo[1,5-a]piridin-2-ilamino)-N-metilbenzamida; N-fenil-5-(2-(pirrolidin-1-ilmetil)-1H-benzo[d]imidazol-6-il)-[1,2,4]triazolo[1,5-a]piridin-2-amina; 5-(4-metilisoxazol-3-il)-N-fenil-[1,2,4]triazolo[1,5-a]piridin-2-amina; N-(4-fluorofenil)-5-(1H-indazol-6-il)-[1,2,4]triazolo[1,5-a]piridin-2-amina; N-(4-fluorofenil)-5-(2-((metilamino)metil)-1H-benzo[d]imidazol-6-il)-[1,2,4]triazolo[1,5-a]piridin-2-amina; 5-(3-amino-1H-indazol-6-il)-N-fenil-[1,2,4]triazolo[1,5-a]piridin-2-amina; 5-(2-((metilamino)metil)-1H-benzo[d]imidazol-6-il)-N-(4-(trifluorometil)fenil)-[1,2,4]triazolo[1,5-a]piridin-2-amina; 5-(5-metilisoxazol-3-il)-N-fenil-[1,2,4]triazolo[1,5-a]piridin-2-amina; 5-(2-(metilamino)-1H-benzo[d]imidazol-5-il)-N-fenil-[1,2,4]triazolo[1,5-a]piridin-2-amina;5-(1H-indazol-6-il)-N-fenil-[1,2,4]triazolo[1,5-a]piridin-2-amina; 5-(2-((dimetilamino)metil)-1H-benzo[d]imidazol-5-il)-N-fenil-[1,2,4]triazolo[1,5-a]piridin-2-amina;345
imagen14 imagen15 imagen16 imagen17 en donde la afección inmunológica es el síndrome de Behcet, la enfermedad mastocitaria no alérgica, la espondilitis anquilosante, la osteoartritis, la artritis reumatoide, la esclerosis múltiple, el lupus, la enfermedad inflamatoria del intestino, la colitis ulcerosa, la enfermedad de Crohn, la miastenia grave, la enfermedad de Grave, el rechazo de trasplantes, el rechazo humoral de trasplantes, el rechazo no humoral de trasplantes, el 5 rechazo celular de trasplantes, la púrpura trombocitopénica inmune, la púrpura trombocitopénica idiopática, la diabetes, la respuesta inmunológica a la infestación bacteriana, parasitaria, helmíntica o a la infección viral, el eccema, la dermatitis, la enfermedad de injerto contra hospedador, la enfermedad de Goodpasture, la enfermedad hemolítica del recién nacido, la anemia hemolítica autoinmune, el síndrome antifosfolipídico, la vasculitis asociada a ANCA, el síndrome de Churg-Strauss, la granulomatosis de Wegener, el pénfigo vulgar, la10 enfermedad del suero, la crioglobulinemia mixta, la neuropatía periférica asociada al anticuerpo IgM, la poliangitis microscópica, la tiroiditis de Hashimoto, el síndrome de Sjogren, una afección fibrótica o la cirrosis biliar primaria; oen donde la afección inflamatoria es la vasculitis no-ANCA, la psoriasis, el asma, la rinitis alérgica, la conjuntivitis alérgica, la urticaria crónica, la urticaria, la anafilaxia, la bronquitis, la enfermedad pulmonar obstructiva crónica,15 la fibrosis quística, la enfermedad inflamatoria del intestino, el síndrome del intestino irritable, la gota, la enfermedad de Crohn, la colitis mucosa, la colitis ulcerosa, la alergia a un antígeno intestinal, la diabetes o la obesidad; oen donde la enfermedad cardiovascular es la reestenosis, la aterosclerosis, el accidente cerebrovascular, el infarto de miocardio, el daño isquémico al corazón, pulmón, intestino, riñón, hígado, páncreas, bazo o cerebro; o20 en donde la enfermedad neurodegenerativa o neuroinflamatoria es la enfermedad de Huntington, la enfermedad de Alzheimer, o la encefalitis o el daño asociados a virus o bacterias.350
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- 2009-09-08 BR BRPI0918854-1A patent/BRPI0918854A2/pt not_active IP Right Cessation
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- 2009-09-08 JP JP2011526054A patent/JP5689060B2/ja not_active Expired - Fee Related
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- 2009-09-08 AU AU2009288618A patent/AU2009288618B2/en not_active Ceased
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|---|---|
| CO6531502A2 (es) | 2012-09-28 |
| US20100093698A1 (en) | 2010-04-15 |
| EP2344494A1 (en) | 2011-07-20 |
| RU2011113540A (ru) | 2012-10-20 |
| NI201100048A (es) | 2011-11-17 |
| TW201024293A (en) | 2010-07-01 |
| CN104910148B (zh) | 2017-06-27 |
| CN104910148A (zh) | 2015-09-16 |
| AU2009288618B2 (en) | 2014-10-02 |
| US20130005707A1 (en) | 2013-01-03 |
| AU2009288618A1 (en) | 2010-03-11 |
| IL211549A0 (en) | 2011-05-31 |
| NZ591551A (en) | 2011-10-28 |
| ZA201101586B (en) | 2012-05-30 |
| JP5689060B2 (ja) | 2015-03-25 |
| PE20110387A1 (es) | 2011-06-22 |
| CN102203093A (zh) | 2011-09-28 |
| EP2344494B1 (en) | 2016-04-20 |
| ECSP11010945A (es) | 2011-05-31 |
| CN102203093B (zh) | 2015-05-13 |
| TWI453207B (zh) | 2014-09-21 |
| RU2552642C2 (ru) | 2015-06-10 |
| WO2010027500A1 (en) | 2010-03-11 |
| US8299056B2 (en) | 2012-10-30 |
| CL2011000480A1 (es) | 2011-09-16 |
| JP2012502029A (ja) | 2012-01-26 |
| CA2735806A1 (en) | 2010-03-11 |
| BRPI0918854A2 (pt) | 2019-02-26 |
| MX2011002536A (es) | 2011-04-04 |
| KR20110053266A (ko) | 2011-05-19 |
| CR20110132A (es) | 2011-06-20 |
| IL211549A (en) | 2017-04-30 |
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