ES2673426T3 - Compuestos de tioacetato, composiciones y métodos de uso - Google Patents

Compuestos de tioacetato, composiciones y métodos de uso Download PDF

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ES2673426T3
ES2673426T3 ES15166826.6T ES15166826T ES2673426T3 ES 2673426 T3 ES2673426 T3 ES 2673426T3 ES 15166826 T ES15166826 T ES 15166826T ES 2673426 T3 ES2673426 T3 ES 2673426T3
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halogen
och3
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Samedy Ouk
Esmir Gunic
Jean-Michel Vernier
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Ardea Biociences Inc
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Ardea Biociences Inc
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    • C07—ORGANIC CHEMISTRY
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    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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 ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/70—Sulfur atoms
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    • 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
    • A61K31/425—Thiazoles
    • A61K31/426—1,3-Thiazoles
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    • 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
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    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4418—Non condensed pyridines; Hydrogenated derivatives thereof having a carbocyclic group directly attached to the heterocyclic ring, e.g. cyproheptadine
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    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/443—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with oxygen as a ring hetero atom
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    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/4433—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with oxygen as a ring hetero atom
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    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
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    • 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
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
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    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
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    • 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
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/472—Non-condensed isoquinolines, e.g. papaverine
    • A61K31/4725—Non-condensed isoquinolines, e.g. papaverine containing further heterocyclic rings
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    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/4965—Non-condensed pyrazines
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    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/4965—Non-condensed pyrazines
    • A61K31/497—Non-condensed pyrazines containing further heterocyclic rings
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    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/50—Pyridazines; Hydrogenated pyridazines
    • A61K31/502—Pyridazines; Hydrogenated pyridazines ortho- or peri-condensed with carbocyclic ring systems, e.g. cinnoline, phthalazine
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    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
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    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
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    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
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    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
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    • C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members 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 ring carbon atoms
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Abstract

Un compuesto de la Fórmula (I):**Fórmula** en donde: Ra y Rb se seleccionan de H, halógeno, C1 a C6 alquilo; o Ra y Rb, junto con el átomo de carbono al que están unidos, forman un anillo de 3-, 4-, 5- o 6-miembros, que contiene opcionalmente uno o dos heteroátomos seleccionados de O, N y S; M es H, C1-3 alquilo o un catión farmacéuticamente aceptable; X1 es N, CH, C(halógeno) o C(C1-C4 alquilo); X2 es N o CH; X3 es N, CH, C(halógeno) o C(C1-C4 alquilo); X4 es N o CH; en donde uno de X1, X2, X3 o X4 es N; Y1 es N o CR1; Y2 es N o CR2; R1 es H, CF3, CH3, OCH3, F o Cl; R2 es H, metilo, etilo, propilo, isopropilo, terc-butilo, ciclopropilo, ciclobutilo, CF3, OH, OCH3, etoxi, SH, SCH3, SCH2CH3, CH2OH, C(CH3)2OH, Cl, F, CN, COOH, COOR2', CONH2, CONHR2' o SO2NH2; en donde R2' es H o C1-3 alquilo; R3 es H, halógeno, -CN, C1 a C6 alquilo, C1 a C6 alcoxi; y R4 es H, halógeno, -CN, C1 a C6 alquilo, C1 a C6 alcoxi; o R3 y R4 junto con los átomos de carbono a los que están unidos forman un anillo de 5- o 6-miembros opcionalmente sustituido, que contiene opcionalmente uno o dos heteroátomos seleccionados de O, N y S, en donde dicho anillo de 5- o 6- miembros es un anillo saturado, uno insaturado o uno aromático; con la condición de que el compuesto de la Fórmula (I) no sea ácido 1-(3-(4-cianofenil)piridin-4- iltio)ciclopropanocarboxílico.

Description

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DESCRIPCIÓN
Compuestos de tioacetato, composiciones y métodos de uso Antecedentes de la invención
El ácido úrico es el resultado de la oxidación de la xantina. Los trastornos del metabolismo del ácido úrico incluyen, entre otros, policitemia, metaplasia mieloide, gota, ataque recurrente de gota, artritis gotosa, hiperuricemia, hipertensión, enfermedad cardiovascular, enfermedad coronaria, síndrome de Lesch-Nyhan, síndrome de Kelley-Seegmiller, enfermedad renal, cálculos renales, insuficiencia renal, inflamación de las articulaciones, artritis, urolitiasis, plumbismo, hiperparatiroidismo, psoriasis o sarcoidosis. Se puede hacer referencia al documento US2010/056464 y al documento WO2011/159840.
Resumen de la invención
En ciertas modalidades, se proporcionan aquí compuestos, métodos y composiciones, por ejemplo, para la modulación de niveles de ácido úrico en suero (AUs) o el tratamiento de la gota o hiperuricemia en individuos que lo necesitan. En algunas modalidades, tales composiciones comprenden y tales métodos comprenden la administración a un individuo que lo necesita de una cantidad eficaz de un compuesto de la Fórmula I:
imagen1
en donde:
Ra y Rb se seleccionan de H, halógeno, C1 a Ce alquilo; o Ra y Rb, junto con el átomo de carbono al que están unidos, forman un anillo de 3-, 4-, 5- o 6-miembros, que contiene opcionalmente uno o dos heteroátomos seleccionados de O, N yS;
M es H, C1-3 alquilo o un catión farmacéuticamente aceptable;
X1 es N, CH, C(halógeno) o C(C1-C4 alquilo);
X2 es N o CH;
X3 es N, CH, C(halógeno) o C(C1-C4 alquilo);
X4 es N o CH; en donde uno de X1, X2, X3 o X4 es N;
Y1 es N oCR1;
Y2 es N o CR2;
R1 es H, CF3, CH3, OCH3, F o Cl;
R2 es H, metilo, etilo, propilo, isopropilo, tere-butilo, ciclopropilo, ciclobutilo, CF3, OH, OCH3, etoxi, SH, SCH3, SCH2CH3, CH2OH, C(CH3)2OH, Cl, F, CN, COOH, COOR2', CONH2, CONHR2' o SO2NH2; en donde R2' es H o C1-3 alquilo;
R3 es H, halógeno, -CN, C1 a Ce alquilo, C1 a Ce alcoxi; y R4 es H, halógeno, -CN, C1 a Ce alquilo, C1 a Ce alcoxi; o
R3 y R4 junto con los átomos de carbono a los que están unidos forman un anillo de 5- o e-miembros opcionalmente sustituido, que contiene opcionalmente uno o dos heteroátomos seleccionados de O, N y S, en donde dicho anillo de 5- o e- miembros puede ser un anillo saturado, insaturado o aromático;
(i) el compuesto de la Fórmula (I) no es ácido 1-(3-(4-cianofenil)piridin-4-iltio)ciclopropanocarboxílico.
En ciertas modalidades, se proporciona un compuesto de la Fórmula (I), en donde uno de X1, X2, X3 o X4 es N. Ciertas modalidades específicas proporcionadas en la presente descripción describen un compuesto de la Fórmula (I-A), (I-B), (I-C)o(I-D):
imagen2
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65
En algunas modalidades de la presente descripción se proporciona un compuesto de la Fórmula (I), en donde R3 es H, CH3, OCH3, CF3, F o Cl; y R4 es H, CH3, OCH3, CF3, F o Cl. En ciertas modalidades específicas, R3 y R4 son ambas H.
Algunas modalidades proporcionadas en la presente descripción describen un compuesto de la Fórmula (I), en donde R3 y R4 junto con los átomos de carbono a los que están unidos forman un anillo de 5- o 6-miembros opcionalmente sustituido, que contiene opcionalmente uno o dos heteroátomos seleccionados de O, N y S, en donde dicho anillo de 5- o 6- miembros puede ser un anillo saturado, insaturado o aromático.
Ciertas modalidades proporcionadas en la presente descripción describen un compuesto de la Fórmula (I), en donde R3 y R4 junto con los átomos de carbono a los que están unidos forman un anillo aromático de 6-miembros opcionalmente sustituido. Ciertas modalidades específicas proporcionadas en la presente descripción describen un compuesto de la Fórmula (I-K):
imagen3
en donde n es 1, 2, 3 o 4; y
cada R5 se selecciona independientemente de H, metilo, etilo, propilo, isopropilo, tere-butilo, ciclopropilo, ciclobutilo, CF3, OH, OCH3, etoxi, SH, SCH3, SCH2CH3, CH2OH, C(CH3)2OH, Cl, F, CN, COOH, COOR5', CONCH2, CONHR5' o SO2NH2; en donde R5' es H o C1-3 alquilo.
En ciertas modalidades de la presente descripción se proporciona un compuesto de la Fórmula (I), en donde Ra es H o CH3; y Rb es H o CH3. En modalidades específicas, Ra y Rb son ambos CH3. Ciertas modalidades específicas proporcionadas en la presente descripción describen un compuesto de la Fórmula (I-L):
imagen4
En otras modalidades o modalidades adicionales, X1 es CH; X2 es N; X3 es CH; y X4es CH. En otras modalidades o modalidades adicionales, Y1 es CR1; y Y2 es CR2.
Ciertas modalidades específicas proporcionadas en la presente descripción describen un compuesto de la Fórmula (IB), seleccionado del grupo que consiste en:

Claims (12)

  1. 5
    10
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    40
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    65
    Reivindicaciones
    1. Un compuesto de la Fórmula (I):
    imagen1
    en donde:
    Ra y Rb se seleccionan de H, halógeno, Ci a C6 alquilo; o Ra y Rb, junto con el átomo de carbono al que están unidos, forman un anillo de 3-, 4-, 5- o 6-miembros, que contiene opcionalmente uno o dos heteroátomos seleccionados de O, N y S;
    M es H, C1-3 alquilo o un catión farmacéuticamente aceptable;
    X1 es N, CH, C(halógeno) o C(C1-C4 alquilo);
    X2 es N o CH;
    X3 es N, CH, C(halógeno) o C(Ci-C4 alquilo);
    X4 es N o cH; en donde uno de X1, X2, X3 o X4 es N;
    Y1 es NoCR1;
    Y2 es N o CR2;
    R1 es H, CF3, CH3, OCH3, F o Cl;
    R2 es H, metilo, etilo, propilo, isopropilo, tere-butilo, ciclopropilo, ciclobutilo, CF3, OH, OCH3, etoxi, SH, SCH3, SCH2CH3, CH2OH, C(CH3)2OH, Cl, F, CN, COOH, COOR2', CONH2, CONHR2' o SO2NH2; en donde R2' es H o C1-3 alquilo;
    R3 es H, halógeno, -CN, C1 a C6 alquilo, C1 a C6 alcoxi; y
    R4 es H, halógeno, -CN, C1 a C6 alquilo, C1 a C6 alcoxi; o
    R3 y R4 junto con los átomos de carbono a los que están unidos forman un anillo de 5- o 6-miembros
    opcionalmente sustituido, que contiene opcionalmente uno o dos heteroátomos seleccionados de O, N y S, en
    donde dicho anillo de 5- o 6- miembros es un anillo saturado, uno insaturado o uno aromático;
    con la condición de que el compuesto de la Fórmula (I) no sea ácido 1-(3-(4-cianofenil)piridin-4-
    iltio)ciclopropanocarboxílico.
  2. 2. Un compuesto de la reivindicación 1, en donde:
    R3 es H, CH3, OCH3, CF3, F o Cl; and
    R4 es H, CH3, OCH3, CF3, F o Cl.
  3. 3. Un compuesto de la reivindicación 1, en donde R3 y R4 junto con los átomos de carbono a los que están unidos forman un anillo de 5- o 6-miembros opcionalmente sustituido, que contiene opcionalmente uno o dos heteroátomos seleccionados de O, N y S, en donde dicho anillo de 5- o 6- miembros puede ser un anillo saturado, insaturado o aromático.
  4. 4. Un compuesto de la reivindicación 3, de la Fórmula (I-K):
    imagen2
    en donde n es 1, 2, 3 o 4; y
    cada R5 se selecciona independientemente de H, metilo, etilo, propilo, isopropilo, tere-butilo, ciclopropilo, ciclobutilo, CF3, OH, OCH3, etoxi, SH, SCH3, SCH2CH3, CH2OH, C(CH3)2OH, Cl, F, CN, COOH, COOR5', CONCH2, CONHR5' o SO2NH2; en donde R5' es H o C1-3 alquilo.
  5. 5. Un compuesto de la reivindicación 1, en donde:
    Ra es H o CH3; y
    RbesHo CH3.
    5
  6. 6. Un compuesto de la reivindicación 5, de la Fórmula (I-L):
    imagen3
    20
    25
  7. 7.
    30
    35
    en donde X1 es CH;
    X2 es N;
    X3 es CH; y
    X4 es CH; y opcionalmente en donde Y1 es CR1 y Y2 es CR2.
    Un compuesto de la reivindicación 6, de la Fórmula (I-M):
    imagen4
    40 y opcionalmente en donde R1, R3 y R4 son todos H.
  8. 8. Un compuesto de la reivindicación 1, en donde Ra y Rb juntos con el átomo de carbono al que están unidos forman un anillo de 3-, 4-, 5- o 6-miembros, que contiene opcionalmente uno o dos heteroátomos seleccionados de O, N y S.
    45
  9. 9. Un compuesto de la reivindicación 1, en donde M es H.
  10. 10. Un compuesto de la Fórmula (I) de acuerdo con una cualquiera de las reivindicaciones 1 a 9 para usar en la reducción de los niveles séricos de ácido úrico en un ser humano, tratar la hiperuricemia en un humano con
    50 gota, tratar la hiperuricemia en un ser humano, tratar la gota en un ser humano, tratar o prevenir una afección
    caracterizada por niveles anormales de ácido úrico en tejidos u órganos en un individuo, y opcionalmente, en donde el compuesto se usa en combinación con un segundo agente eficaz para el tratamiento de la gota.
  11. 11. El compuesto de la Fórmula (I) como se define en las reivindicaciones 1-9 para usar de acuerdo con la
    55 reivindicación 10, en donde la afección es gota, un ataque recurrente de gota, artritis gotosa, hiperuricemia,
    hipertensión, una enfermedad cardiovascular, enfermedad coronaria, síndrome de Lesch-Nyhan, síndrome de Kelley-Seegmiller, enfermedad renal, cálculos renales, insuficiencia renal, inflamación de las articulaciones, artritis, urolitiasis, plumbismo, hiperparatiroidismo, soriasis, sarcoidosis, hipoxantina-guanina fosforribosiltransferasa (HPRT) deficiencia o una combinación de los mismos.
    60
  12. 12. El compuesto de la Fórmula (I) como se define en las reivindicaciones 1-9 para usar de acuerdo con la reivindicación 10, en donde el segundo agente es un inhibidor URAT 1, un inhibidor de xantina oxidasa, una xantina deshidrogenasa, un inhibidor de xantina oxidorreductasa, o combinaciones de estos; o, en donde el segundo agente es allopurinol, febuxostat, FYX-051, o combinaciones de los mismos.
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