ES2571741T3 - Bencimidazoles sustituidos como inhibidores de Mps-1 quinasa - Google Patents

Bencimidazoles sustituidos como inhibidores de Mps-1 quinasa

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ES2571741T3
ES2571741T3 ES12710760T ES12710760T ES2571741T3 ES 2571741 T3 ES2571741 T3 ES 2571741T3 ES 12710760 T ES12710760 T ES 12710760T ES 12710760 T ES12710760 T ES 12710760T ES 2571741 T3 ES2571741 T3 ES 2571741T3
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alkyl
aryl
heteroaryl
alkoxy
cycloalkyl
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Ulrich Klar
Marcus Koppitz
Duy Nguyen
Dirk Kosemund
Roland Neuhaus
Gerhard Siemeister
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Bayer Intellectual Property GmbH
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Bayer Intellectual Property GmbH
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    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D235/08—Radicals containing only hydrogen and carbon atoms
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    • A61K31/4164—1,3-Diazoles
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    • 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
    • A61K31/4196—1,2,4-Triazoles
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    • A61K31/42—Oxazoles
    • A61K31/422—Oxazoles not condensed and containing further heterocyclic 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
    • A61K31/435—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
    • A61K31/4439—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
    • 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
    • A61K31/535—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
    • A61K31/5375—1,4-Oxazines, e.g. morpholine
    • A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • 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
    • 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
    • A61P35/00—Antineoplastic agents
    • A61P35/02—Antineoplastic agents specific for leukemia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/04—Antineoplastic agents specific for metastasis
    • A—HUMAN NECESSITIES
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
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    • 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
    • C07D403/12—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 linked by a chain containing hetero atoms as chain links
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    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • 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
    • C07D413/12—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 linked by a chain containing hetero atoms as chain links

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  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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Abstract

Un compuesto de fórmula general (I) : **Fórmula** en la que: A representa **Fórmula** en las que * indica el punto de unión de dichos grupos con el resto de la molécula; Z representa un grupo -C(>=O)N(H)R1 o -C(>=S)N(H)R1; R1 representa un átomo de hidrógeno o un grupo alquil C1-C6- o cicloalquil C3-C6-; en el que dicho grupo alquil C1-C6- o cicloalquil C3-C6- está opcionalmente sustituido, de forma idéntica o diferente, con 1, 2, 3 o 4 grupos seleccionados entre: halógeno, -OH, -CN, alquil C1-C6-, alcoxi C1-C6-; R2 representa un átomo de hidrógeno o un grupo alquil C1-C6- o cicloalquil C3-C6-; en el que dicho grupo alquil C1-C6- o cicloalquil C3-C6- está opcionalmente sustituido, de forma idéntica o diferente, con 1, 2, 3 o 4 grupos seleccionados entre: halógeno, OH, -CN, alquil C1-C6-, alcoxi C1-C6-; R3 representa un átomo de hidrógeno o un átomo de halógeno o un grupo -CN, alquil C1-C6-, -(CH2)m-alquenilo C2-C6, -(CH2)mcicloalquenilo C4-C8, -(CH2)m-alquinilo C2-C6, -(CH2)m-cicloalquilo C3-C6, -(CH2)m-(heterocicloalquilo de 3 a 7 miembros), -(CH2)m-(heterocicloalquenilo de 4 a 8 miembros), -aril-alquil C1-C6-, heteroaril-alquil C1-C6-, halo-alquil C1-C6-, R6a(R6b)N-alquil C1-C6-, halo-alcoxi C1-C6-alquil C1-C6-, cicloalquil C3-C6-, heterocicloalquil de 3 a 7 miembros-, alquenil C2-C6-, cicloalquenil C4-C8-, alquinil C2-C6-, aril-, -alquil C1-C6-arilo, -alquil C1-C6-heteroarilo, heteroaril-, alquil C1-C6-X-, -X-(CH2)m-alquenilo C2-C6, -X-(CH2)mcicloalquenilo C4-C8, -X-(CH2)m-alquinilo C2-C6, -X-(CH2)m-cicloalquilo C3-C6, -X-(CH2)m-(heterocicloalquilo de 3 a 7 miembros), -X-(CH2)m-(heterocicloalquenilo de 4 a 8 miembros), aril-X-, heteroaril-X-, -C(>=O)R6, -C(>=O)N(H)R6a, -C(>=O)N(R6a)R6b, -C(>=O)O-R6, -N(R6a)R6b, -NO2, -N(H)C(>=O)R6, -OR6, -SR6, -S(>=O)R6, -S(>=O)2R6, -S(>=O)(>=NR6a)R6b, -S(>=O)2N(R6b)R6c, -S-(CH2)n-N(R6a)R6b, o -S-(CH2)n-(heterocicloalquilo de 3 a 7 miembros); estando dicho alquil C1-C6-, -(CH2)m-alquenilo C2-C6, -(CH2)m-alquinilo C2-C6, -(CH2)m-cicloalquilo C3-C6, aril-alquil C1-C6-, heteroaril-alquil C1-C6-, cicloalquil C3-C6-, heterocicloalquil de 3 a 7 miembros-, alquenil C2-C6-, cicloalquenil C4-C8-, alquinil C2-C6-, aril-, alquil C1-C6-X-, -X-(CH2)m-alquenilo C2-C6, -X-(CH2)mcicloalquenilo C4-C8, -X-(CH2)m-alquinilo C2-C6, -X-(CH2)m-cicloalquilo C3-C6, -X-(CH2)m-(heterocicloalquilo de 3 a 7 miembros), -X-(CH2)m-(heterocicloalquenilo de 4 a 8 miembros), aril-X-, heteroaril-X-, -alquil C1-C6-arilo, -alquil C1-C6-heteroarilo o heteroaril- que está opcionalmente sustituido, de forma idéntica o diferente, con 1, 2, 3, 4 o 5 grupos R7; 30 R4a, R4b, R4c, R4d, representan, independientemente entre sí, un átomo de hidrógeno o halógeno, o un grupo -CN, alquil C1-C6-, alcoxi C1-C6-, halo-alquil C1-C6-, halo-alcoxi C1-C6-, R6a(R6b)N-alquil C1-C6-, HO-alquil C1-C6-, NC-alquil C1-C6-, alcoxi C1-C6-alquil C1-C6-, halo-alcoxi C1-C6-alquil C1-C6-; R5 representa un átomo de hidrógeno o un grupo alquil C1-C6-, -(CH2)n-alquenilo C2-C6, -(CH2)n-alquinilo C2-C6, - (CH2)m-cicloalquilo C3-C6, -(CH2)m-(heterocicloalquilo de 3 a 7 miembros), aril-alquil C1-C6-, heteroaril-alquil C1-C6-, halo-alquil C1-C6-, R6a(R6b)N-alquil C1-C6-, HO-alquil C1-C6-, -alquil C1-C6-CN, alcoxi C1-C6-alquil C1-C6-, halo-alcoxi C1-C6-alquil C1-C6-, cicloalquil C3-C6-, heterocicloalquil de 3 a 7 miembros-, cicloalquenil C4-C8-, aril- o heteroaril-; estando dicho grupo alquil C1-C6-, -(CH2)n-alquenilo C2-C6, -(CH2)n-alquinilo C2-C6, -(CH2)m-cicloalquilo C3-C6, -(CH2)m-(heterocicloalquilo de 3 a 7 miembros), aril-alquil C1-C6-, heteroaril-alquil C1-C6-, halo-alquil C1-C6-, R6a(R6b)N-alquil C1-C6-, HO-alquil C1-C6-, -alquil C1-C6-CN, alcoxi C1-C6-alquil C1-C6-, halo-alcoxi C1-C6-alquil C1-C6-, cicloalquil C3-C6-, heterocicloalquil de 3 a 7 miembros-, cicloalquenil C4-C8-, aril- o heteroaril- opcionalmente sustituido, de forma idéntica o diferente, con 1, 2, 3, 4 o 5 grupos R8; R6, R6a, R6b, R6c representan, independientemente de si, un átomo de hidrógeno o un grupo alquil C1-C6-, HO-alquil C1-C6-, cicloalquil C3-C6-, alquenil C2-C6-, heterocicloalquil de 3 a 7 miembros-, aril-, heteroaril-, aril-alquil C1-C6- o heteroaril-alquil C1-C6-; R7 representa un átomo de hidrógeno o halógeno o un grupo HO-, -CN, alcoxi C1-C6-, halo-alcoxi C1-C6-, alquil C1-C6-, halo-alquil C1-C6-, R6a(R6b)N-alquil C1-C6-, HO-alquil C1-C6-, alcoxi C1-C6-alquil C1-C6-, halo-alcoxi C1-C6-alquil C1-C6-, alquenil C2-C6-, alquinil C2-C6-, heterocicloalquil de 3 a 7 miembros-, aril-, heteroaril-, -C(>=O)R6, -15 C(>=O)N(H)R6a, -C(>=O)N(R6a)R6b, -C(>=O)O-R6, -N(R6a)R6b, -NO2, -N(H)C(>=O)R6, -N(R6c)C(>=O)R6, -N(H)C(>=O)N(Rba)R6b, -N(R6c)C(>=O)N(R6a)R6b, -N(H)C(>=O)OR6, -N(R6c)C(>=O)OR6, -N(H)S(>=O)R6, -N(R6c)S(>=O)R6 -N(H)S(>=O)2R6, -N(R6c)S(>=O)2R6, -N>=S(>=O)(R6a)R6b, -OR6, -O(C>=O)R6, -O(C>=O)N(R6a)R6b, -O(C>=O)OR6, -SR6, -SF5, -S(>=O)R6, -S(>=O)N(H)R6, -S(>=O)N(R6a)R6b, -S(>=O)2R6, -S(>=O)2N(H)R6, -S(>=O)2N(R6a)R6b o -S(>=O)(>=NR6c)R6; en el que dicho grupo aril- o heteroaril- está opcionalmente sustituido, de forma idéntica o diferente, con 1, 2 o 3 grupos alquil C1-C6-; o cuando 2 grupos R7 están presentes en posición orto entre sí en un anillo de arilo, dichos 2 grupos R7 en conjunto forman un puente: *O(CH2)2O*, *O(CH2)O*, *NH(C(>=O))NH*, en los que * representa el punto de unión a dicho anillo de arilo; R8 representa un átomo de hidrógeno o halógeno o un grupo -CN, alcoxi C1-C6-, alquil C1-C6-, halo-alquil C1-C6-, R6a(R6b)N-alquil C1-C6-, HO-alquil C1-C6-, alcoxi C1-C6-alquil C1-C6-, halo-alcoxi C1-C6-alquil C1-C6-, alquenil C2-C6-, alquinil C2-C6-, heterocicloalquil de 3 a 7 miembros-, aril-, heteroaril-, -C(>=O)R6, -C(>=O)N(H)R6a, -C(>=O)N(R6a)R6b, -C(>=O)O-R6, -N(R6a)R6b, -NO2, -N(H)C(>=O)R6, -N(R6c)C(>=O)R6, -N(H)C(>=O)N(R6a)R6b, -N(R6c)C(>=O)N(R6a)R6b, -N(H)C(>=O)OR6, -N(R6c)C(>=O)OR6, -N(H)S(>=O)R6, -N(R6c)S(>=O)R6, -N(H)S(>=O)2R6, -N(R6c)S(>=O)2R6, -N>=S(>=O)(R6a)R6b, -OR6, -O(C>=O)R6, -O(C>=O)N(R6a)R6b, -O(C>=O)OR6, -SR6, -S(>=O)R6, -S(>=O)N(H)R6, -S(>=O)N(R6a)R6b, -S(>=O)2R6, -S(>=O)2N(H)R6, -S(>=O)2N(R6a)R6b, -S(>=O)(>=NR6c)R6 o -S(>=O)2-(heterocicloalquilo de 3 a 7 miembros); en el que dicho grupo heterocicloalquil de 3 a 7 miembros- o heteroaril-, está opcionalmente sustituido, de forma idéntica o diferente, con 1, 2, 3 o 4 grupos alquil C1-C6-; m es un número entero de 0, 1, 2, 3, 4, 5, o 6; n es un número entero de 0, 1, 2, 3, 4, o 5; y X es S, S(>=O), S(>=O)2, O, NR6, CR6aR6b, C(>=CR6aR6b), C(>=O) o C(OH)(R6a) ; o un estereoisómero, un tautómero, un N-óxido, un hidrato, un solvato, o una sal del mismo, o una mezcla de los mismos.
ES12710760T 2011-03-31 2012-03-28 Bencimidazoles sustituidos como inhibidores de Mps-1 quinasa Active ES2571741T3 (es)

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EP11160696 2011-03-31
EP11170306 2011-06-17
EP11190249 2011-11-23
PCT/EP2012/055562 WO2012130905A1 (en) 2011-03-31 2012-03-28 Substituted benzimidazoles

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US (1) US9388140B2 (es)
EP (1) EP2691375B1 (es)
JP (1) JP6001049B2 (es)
CN (1) CN103582632B (es)
CA (1) CA2831710A1 (es)
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WO (1) WO2012130905A1 (es)

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