AR096075A2 - Derivados fusionados de pirimidina para la inhibición de la actividad quinasa de tirosina - Google Patents
Derivados fusionados de pirimidina para la inhibición de la actividad quinasa de tirosinaInfo
- Publication number
- AR096075A2 AR096075A2 ARP140101695A ARP140101695A AR096075A2 AR 096075 A2 AR096075 A2 AR 096075A2 AR P140101695 A ARP140101695 A AR P140101695A AR P140101695 A ARP140101695 A AR P140101695A AR 096075 A2 AR096075 A2 AR 096075A2
- Authority
- AR
- Argentina
- Prior art keywords
- alkyl
- heterocyclic
- amino
- alkoxy
- heterocycle
- Prior art date
Links
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 title 1
- 108091000080 Phosphotransferase Proteins 0.000 title 1
- 230000005764 inhibitory process Effects 0.000 title 1
- 102000020233 phosphotransferase Human genes 0.000 title 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 title 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 21
- 125000000623 heterocyclic group Chemical group 0.000 abstract 13
- 125000000217 alkyl group Chemical group 0.000 abstract 6
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 abstract 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 4
- 125000001072 heteroaryl group Chemical group 0.000 abstract 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 3
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 abstract 3
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 abstract 3
- 125000003545 alkoxy group Chemical group 0.000 abstract 3
- 125000005153 alkyl sulfamoyl group Chemical group 0.000 abstract 3
- 125000003118 aryl group Chemical group 0.000 abstract 3
- 125000005843 halogen group Chemical group 0.000 abstract 3
- 229910052760 oxygen Inorganic materials 0.000 abstract 3
- 125000001424 substituent group Chemical group 0.000 abstract 3
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 abstract 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- 206010028980 Neoplasm Diseases 0.000 abstract 2
- 125000002431 aminoalkoxy group Chemical group 0.000 abstract 2
- 125000004103 aminoalkyl group Chemical group 0.000 abstract 2
- 125000005122 aminoalkylamino group Chemical group 0.000 abstract 2
- -1 aminocarbamoyl Chemical group 0.000 abstract 2
- 125000004391 aryl sulfonyl group Chemical group 0.000 abstract 2
- 125000002619 bicyclic group Chemical group 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 2
- 125000004122 cyclic group Chemical group 0.000 abstract 2
- 125000005343 heterocyclic alkyl group Chemical group 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- 229920006395 saturated elastomer Polymers 0.000 abstract 2
- 229910052717 sulfur Inorganic materials 0.000 abstract 2
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 abstract 1
- 125000006528 (C2-C6) alkyl group Chemical group 0.000 abstract 1
- 208000023275 Autoimmune disease Diseases 0.000 abstract 1
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 abstract 1
- 150000001204 N-oxides Chemical class 0.000 abstract 1
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 abstract 1
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 abstract 1
- 125000005115 alkyl carbamoyl group Chemical group 0.000 abstract 1
- 125000005596 alkyl carboxamido group Chemical group 0.000 abstract 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 abstract 1
- 125000005135 aryl sulfinyl group Chemical group 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 125000005243 carbonyl alkyl group Chemical group 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 201000010099 disease Diseases 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 abstract 1
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 abstract 1
- 125000005113 hydroxyalkoxy group Chemical group 0.000 abstract 1
- 125000005191 hydroxyalkylamino group Chemical group 0.000 abstract 1
- 125000005182 hydroxyalkylcarbonyl group Chemical group 0.000 abstract 1
- 208000027866 inflammatory disease Diseases 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- 230000001404 mediated effect Effects 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000005499 phosphonyl group Chemical group 0.000 abstract 1
- 150000003230 pyrimidines Chemical class 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
-
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
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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
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
-
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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
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
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- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/538—1,4-Oxazines, e.g. morpholine ortho- or peri-condensed with carbocyclic ring systems
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- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
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Abstract
La presente se refiere a un derivado fusionado de pirimidina que tiene una actividad inhibidora para las quinasas de tirosina, y una composición farmacéutica para prevenir o tratar cánceres, tumores, enfermedades inflamatorias, enfermedades autoinmunes, o enfermedades mediadas en forma inmunológica que lo comprende como principio activo. Reivindicación 1: Un compuesto de la fórmula (1) o una de sus sales aceptables desde el punto de vista farmacéutico, en donde, W es O; X se O, NH, S, SO o SO₂; Y es átomo de hidrógeno, átomo de halógeno, alquilo C₁₋₆ o alcoxi C₁₋₆; A y B son cada uno en forma independiente átomo de hidrógeno, átomo de halógeno, o di(alquil C₁₋₆)aminometilo; Z es arilo o heteroarilo que tiene uno o más sustituyentes seleccionados del grupo que consiste en: átomo de hidrógeno, átomo de halógeno, hidroxi, nitro, ciano, alquilo C₁₋₆, alcoxi C₁₋₆, alcoxicarbonilo C₁₋₆, alcoxi C₁₋₆carbonilo, di(alquil C₁₋₆)amino-alcoxicarbonilo C₂₋₆, amino, alquilamino C₁₋₆, di(alquil C₁₋₆)amino, carbamoilo, alquilcarbamoilo C₁₋₆, di(alquil C₁₋₆)carbamoilo, di(alquil C₁₋₆)amino-alquilcarbamoilo C₂₋₆, sulfamoilo, alquilsulfamoilo C₁₋₆, di(alquil C₁₋₆)sulfamoilo, di(alquil C₁₋₆)amino-alquilsulfamoilo C₂₋₆, arilsulfonilo C₁₋₆, arilsulfinilo C₁₋₆, di(alquil C₁₋₆)fosfonilo, hidroxialquilo C₁₋₆, hidroxicarbonilalquilo C₁₋₆, alcoxi C₁₋₆alquilo C₁₋₆, alquilsulfonil C₁₋₆alquilo C₁₋₆, alquilsulfinil C₁₋₆alquilo C₁₋₆, di(alquil C₁₋₆)fosfonilalquilo C₁₋₆, hidroxialcoxi C₂₋₆, alcoxi C₁₋₆alcoxi C₂₋₆, aminoalquilo C₁₋₆, alquilamino C₁₋₆alquilo C₁₋₆, di(alquil C₁₋₆)aminoalquilo C₁₋₆, di(alquil C₁₋₆)aminoacetilo, aminoalcoxi C₂₋₆, alquilamino C₁₋₆alcoxi C₂₋₆, di(alquil C₁₋₆)aminoalcoxi C₂₋₆, hidroxialquilamino C₂₋₆, alcoxi C₁₋₆alquilamino C₂₋₆, aminoalquilamino C₂₋₆, alquilamino C₁₋₆alquilamino C₂₋₆, di(alquil C₁₋₆)aminoalquilamino C₂₋₆, heteroarilo, heterociclo, oxi heterocíclico, tio heterocíclico, sulfinilo heterocíclico, sulfonilo heterocíclico, sulfamoilo heterocíclico, alquilo C₁₋₆heterocíclico, alcoxi C₁₋₆heterocíclico, amino heterocíclico, alquilamino heterocíclico C₁₋₆, aminoalquilo heterocíclico C₁₋₆, carbonilo heterocíclico, alcoxicarbonilo C₁₋₆ heterocíclico, carbonilalquilo C₁₋₆ heterocíclico, alquiltio C₁₋₆ heterocíclico, arilsulfinilo C₁₋₆ heterocíclico, arilsulfonilo C₁₋₆ heterocíclico amino carbonilo heterocíclico, alquilaminocarbonilo C₁₋₆ heterocíclico, amino carbonilalquilo heterocíclico C₁₋₆, carboxamido heterocíclico, y alquilcarboxamido C₁₋₆ heterocíclico; el arilo se refiere a un anillo aromático cíclico o bicíclico C₆₋₁₂; los heteroarilos cada uno en forma independiente se refieren a un anillo heteroaromático cíclico o bicíclico de 5 a 12 miembros que tiene uno o más N, O, o S; los heterociclos cada uno en forma independiente se refieren a un anillo heterocíclico o bicíclico de 3 a 12 miembros, saturado o parcialmente insaturado que tiene uno o más N, O, S, SO o SO₂, en donde un átomo de carbono que forma el heterociclo en forma opcional tiene uno o más sustituyentes seleccionados del grupo que consiste en alquilo C₁₋₆, hidroxi, hidroxialquilo C₁₋₆, hidroxicarbonilo, alcoxi C₁₋₆, amino, alquilamino C₁₋₆, di(alquil C₁₋₆)amino, di(alquil C₁₋₆)aminoalquilo C₁₋₆, di(alquil C₁₋₆)aminocarbonilo, heterociclo, alquilo C₁₋₆ heterocíclico, y heteroarilo, y en donde, siempre que el heterociclo en forma opcional comprende un átomo de nitrógeno, el átomo de nitrógeno en forma opcional tiene un sustituyente seleccionado del grupo que consiste en átomo de hidrógeno, alquilo C₁₋₆, alquilo C₁₋₆ monohalógeno, alquilo C₁₋₆ dihalógeno, alquilo C₁₋₆ trihalógeno, cicloalquilo C₃₋₆, hidroxialquilo C₂₋₆, alcoxi C₁₋₆alquilo C₂₋₆, alcoxicarbonilo C₁₋₆, hidroxialquilcarbonilo C₁₋₆, alcoxi C₁₋₆carbonilo, carbamoilo, alquilcarbamoilo C₁₋₆, di(alquil C₁₋₆)carbamoilo, sulfamoilo, alquilsulfamoilo C₁₋₆, di(alquil C₁₋₆)sulfamoilo, arilsulfonilo C₁₋₆, amino-alquilo C₂₋₆, alquilamino C₁₋₆alquilo C₂₋₆, di(alquil C₁₋₆)amino-alquilo C₂₋₆, di(alquil C₁₋₆)amino-alquilcarbonilo C₁₋₆, heterociclo, oxi heterocíclico, tio heterocíclico, sulfinilo heterocíclico, sulfonilo heterocíclico, alquilo C₁₋₆ heterocíclico, carbonilo heterocíclico, alcoxicarbonilo C₁₋₆ heterocíclico, arilsulfinilo C₁₋₆ heterocíclico, y alquilsulfonilo heterocíclico C₁₋₆ (en donde, cuando el átomo de nitrógeno forma una amina terciaria, en forma opcional es de forma de N-óxido); y en forma opcional, el alquilo C₁₋₆ está parcialmente saturado o tiene un resto cicloalquilo C₃₋₆ y un átomo de carbono en el heterociclo existe en forma de carbonilo.
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Date | Code | Title | Description |
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FG | Grant, registration |