AR053346A1 - Compuesto derivado de 8h -pirido (2,3-d) pirimidin -7 ona 2,4,8- trisustituida composicion farmaceutica y uso para preparar una composicion para tratamiento y profilxis de una enfermedad mediada por la quinasa csbp/ rk/p38 - Google Patents
Compuesto derivado de 8h -pirido (2,3-d) pirimidin -7 ona 2,4,8- trisustituida composicion farmaceutica y uso para preparar una composicion para tratamiento y profilxis de una enfermedad mediada por la quinasa csbp/ rk/p38Info
- Publication number
- AR053346A1 AR053346A1 ARP060101147A ARP060101147A AR053346A1 AR 053346 A1 AR053346 A1 AR 053346A1 AR P060101147 A ARP060101147 A AR P060101147A AR P060101147 A ARP060101147 A AR P060101147A AR 053346 A1 AR053346 A1 AR 053346A1
- Authority
- AR
- Argentina
- Prior art keywords
- alkyl
- aryl
- optionally substituted
- heteroaryl
- heterocyclyl
- Prior art date
Links
- 102100023482 Mitogen-activated protein kinase 14 Human genes 0.000 title abstract 3
- 239000008194 pharmaceutical composition Substances 0.000 title abstract 3
- 201000010099 disease Diseases 0.000 title abstract 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title abstract 2
- 230000001404 mediated effect Effects 0.000 title abstract 2
- 238000011282 treatment Methods 0.000 title abstract 2
- 239000002131 composite material Substances 0.000 title 1
- 239000000203 mixture Substances 0.000 title 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 23
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 abstract 11
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 abstract 10
- 125000003118 aryl group Chemical group 0.000 abstract 10
- 125000001072 heteroaryl group Chemical group 0.000 abstract 10
- 125000000623 heterocyclic group Chemical group 0.000 abstract 10
- 125000000217 alkyl group Chemical group 0.000 abstract 8
- -1 aryl-C1-10 alkyl Chemical group 0.000 abstract 6
- 229910052760 oxygen Inorganic materials 0.000 abstract 5
- 229910052717 sulfur Inorganic materials 0.000 abstract 5
- 125000005842 heteroatom Chemical group 0.000 abstract 4
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 abstract 3
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 abstract 3
- 125000003341 7 membered heterocyclic group Chemical group 0.000 abstract 3
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 abstract 3
- 125000004093 cyano group Chemical class *C#N 0.000 abstract 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 1
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 abstract 1
- WDHAAJIGSXNPFO-UHFFFAOYSA-N 8h-pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=CN=C2NC(=O)C=CC2=C1 WDHAAJIGSXNPFO-UHFFFAOYSA-N 0.000 abstract 1
- 101100149686 Caenorhabditis elegans snr-4 gene Proteins 0.000 abstract 1
- 108010084680 Heterogeneous-Nuclear Ribonucleoprotein K Proteins 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 238000011321 prophylaxis Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000012453 solvate Substances 0.000 abstract 1
- 125000003107 substituted aryl group Chemical group 0.000 abstract 1
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- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- C07D471/04—Ortho-condensed systems
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- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
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Abstract
Compuesto derivado de 8H-pirido[2,3-d]pirimidin-7-ona 2,4,8-trisustituida, caracterizado porque es de formula (1) o (2) donde G1 y G2 son independientemente N; G3 es CH2; G4 es CH; R1 es C(Z)N(R10')(CR10R20)vRb, C(Z)O(CR10R20)vRb, N(R10')C(Z)(CR10R20)vRb, N(R10')C(Z)N(R10')(CR!0R20)vRb o N(R10')OC(Z)(CR10R20)vRb; R1' se selecciona independientemente en cada caso entre halogeno, alquilo C1-4, halo-alquilo C1-4 sustituido, ciano, nitro, (CR10R20)v'NRdRd', (CR10R20)v'C(O)R12, SR5, S(O)R5, S(O)2R5 o (CR10R20)v'OR13; X es R2', OR2', S(O)mR2', (CH2)n'N(R10')S(O)mR2', (CH2)n'N(R10')C(O)R2', (CH2)n'NR4R14, (CH2)n'N(R2')(R2ö) o N(R10')RhNH-C(=N-CN)NRqRq'; X1 es N(R11), O, S(O)m o CR10R20; Rb es un resto H, alquilo C1-10, cicloalquilo C3-7, cicloalquil C3-7-alquilo C1-10, arilo, aril-alquilo C1-10, heteroarilo, heteroaril-alquilo C1-10, heterociclilo o heterociclil-alquilo C1-10, donde todos estos resto, excluyendo el H, pueden estar opcionalmente sustituidos; Rh se selecciona entre un alquilo C1-10 opcionalmente sustituido -CH2-C(O)-CH2-, -CH2-O-CH2-, -CH2-C(O)N(R10')CH2-CH2-, -CH2-N(R10')C(O)CH2-, -CH2-CH(OR10')-CH2-, -CH2-C(O)O-CH2-CH2- o -CH2-CH2-O-C(O)CH2-; Rq y Rq' se seleccionan independientemente en cada caso entre un resto H, alquilo C1-10, cicloalquilo C3-7, cicloalquil C3-7-alquilo C1-10, cicloalquenilo C5-7, cicloalquenil C5-7-alquilo C1-10, arilo, aril-alquilo C1-10, heteroarilo, heteroaril-alquilo C1-10, heterociclilo o heterociclil- alquilo C1-10 donde todos los restos excepto el resto H, están opcionalmente sustituidos, o Rq y Rq' junto con el N al que están unidos forman un anillo heterocíclico opcionalmente sustituido de 5 a 7 miembros, donde dicho anillo puede contener un heteroátomo adicional seleccionado entre O, N o S; R2 es un resto H, alquilo C1-10, cicloalquilo C3-7, cicloalquilalquilo C3-7, arilo, aril-alquilo C1-10, heteroarilo, heteroaril-alquilo C1-10, heterociclilo o heterociclil-alquilo C1-10, y donde cada uno de estos restos, excluyendo el H, pueden estar opcionalmente sustituido; o R2 es el resto (CR10R20)q'X1(CR10R20)qC(A1)(A2)(A3) o (CR10R20)q'C(A1)(A2)(A3); R2' es un resto H, alquilo C1-10, cicloalquilo C3-7, cicloalquilalquilo C3-7, arilo, aril-alquilo C1-10, heteroarilo, heteroaril-alquilo C1-10, heterociclilo o heterociclil-alquilo C1-10, y donde cada uno de estos restos, excluyendo el H, pueden estar opcionalmente sustituido; o R2ö es un resto H, alquilo C1-10, cicloalquilo C3-7, cicloalquilalquilo C3-7, arilo, aril-alquilo C1-10, heteroarilo, heteroaril-alquilo C1-10, heterociclilo o heterociclil-alquilo C1-10, y donde cada uno de estos restos, excluyendo el H, pueden estar opcionalmente sustituido; o donde R2ö es el resto (CR10R20)tX1(CR10R20)qC(A1)(A2)(A3); A1 es un alquilo C1-10 opcionalmente sustituido; A2 es un alquilo C1-10 opcionalmente sustituido, A3 es H o es un alquilo C1-10 opcionalmente sustituido; R3 es un resto alquilo C1-10, cicloalquilo C3-7, cicloalquil C3-7-alquilo C1-10, arilo, aril-alquilo C1-10, heteroarilo, heteroaril-alquilo C1-10, heterociclilo o heterociclil-alquilo C1-10, y donde cada uno de estos restos pueden estar opcionalmente sustituido; cada uno de R4 y R14 se selecciona independientemente en cada caso entre H, alquilo C1-4, cicloalquilo C3-7, cicloalquil C3-7-alquilo C1-4, arilo, aril-alquilo C1-4, heterociclilo, alquilo C1-4 heterocíclico, heteroarilo, heteroaril-alquilo C1-4, y donde cada uno de estos restos, excluyendo el H, pueden estar opcionalmente sustituido; o R4 y R14 junto con el N al que están unidos forman un anillo heterocíclico opcionalmente sustituido de 4 a 7 miembros, donde dicho anillo contiene opcionalmente un heteroátomo adicional seleccionado entre O, S o NR9; cada uno de R4' y R14' se selecciona independientemente en cada caso entre H o alquilo C1-4, o R4' y R14' junto con el N al que están unidos forman un anillo heterocíclico de 5 a 7 miembros, donde dicho anillo contiene opcionalmente un heteroátomo adicional seleccionado entre NR9'; R5 se selecciona independientemente en cada caso entre H, alquilo C1-4, alquenilo C2-4, alquinilo C2-4 o NR4'R14', excluyendo los restos SR5 que son SNR4'R14'; S(O)2R5 que son SO2H y S(O)R5 que son SOH; R6 se selecciona independientemente en cada caso entre un resto H, alquilo C1-10, cicloalquilo C3-7, heterociclilo, heterociclil-alquilo C1-10, arilo, aril-alquilo C1-10, heteroarilo o heteroaril-alquilo C1-10, y donde cada uno de estos restos, excluyendo el H, puede estar opcionalmente sustituido; R9 se selecciona independientemente en cada caso entre H, C(Z)R6, alquilo C1-10 opcionalmente sustituido, arilo opcionalmente sustituido o un aril-alquilo C1-14 opcionalmente sustituido; R9' se selecciona independientemente en cada caso entre H o alquilo C1-4; R10 y R20 se seleccionan independientemente en cada caso entre H o alquilo C1-4; R10' se selecciona independientemente en cada caso con H o alquilo C1-4; R11 se selecciona independientemente en cada caso entre H o alquilo C1-4; R12 se selecciona independientemente en cada caso entre un resto H, alquilo C1-4, halo-alquilo C1-4 sustituido, alquenilo C2-4, alquinilo C2-4, cicloalquilo C3-7, cicloalquil C3-7- alquilo C1-4, cicloalquenilo C5-7, cicloalquenil C5-7-alquilo C1-4, arilo, aril-alquilo C1-4, heteroarilo, heteroaril-alquilo C1-4, heterociclilo o heterociclil-alquilo C1-4, y donde cada uno de estos restos, excluyendo al H, puede estar opcionalmente sustituido; R13 se selecciona independientemente en cada caso entre un resto H, alquilo C1-4, halo-alquilo C1-4 sustituido, alquenilo C2-4, alquinilo C2-4, cicloalquilo C3-7, cicloalquil C3-7-alquilo C1-4, cicloalquenilo C5-7, cicloalquenil C5-7-alquilo C1-4, arilo, aril-alquilo C1-4, heteroarilo, heteroaril-alquilo C1-4, heterociclilo o heterociclil-alquilo C1-4, y donde cada uno de estos restos, excluyendo al H, puede estar opcionalmente sustituido; cada uno de Rd y Rd' se selecciona independientemente en cada caso entre un resto H, alquilo C1-4, cicloalquilo C3-6, cicloalquil C3-6-alquilo C1-4 y donde cada uno de estos restos, excluyendo al H, puede estar opcionalmente sustituido; o Rd y Rd' junto con el N al que están unidos forman un anillo heterocíclico opcionalmente sustituido de 5 a 6 miembros, donde dicho anillo contiene opcionalmente un heteroátomo adicional seleccionado entre O, S o NR9'; g es 0 o un numero entero que tiene el valor 1, 2, 3, o 4; n' es 0 o un numero entero que tiene un valor de 1 a 10; m es 0 o un numero entero que tiene el valor 1 o 2; q es 0 o un entero que tiene un valor de 1 a 10; q' es 0 o un numero entero que tiene un valor de 1 a 6; t es un numero entero que tiene un valor de 2 a 6; v es 0 o un numero entero que tiene el valor 1 o 2; v' es 0 o un numero entero que tiene el valor 1 o 2; Z se selecciona independientemente en cada caso entre O o S; y una sal farmacéuticamente aceptable, solvato o derivado fisiologicamente funcional del mismo. Composicion farmacéutica que lo comprende. Uso para preparar una composicion farmacéutica para el tratamiento, incluyendo profilaxis, de una enfermedad mediada por la quinasa CSBP/RK/p38.
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