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AR038922A1 - 2-HETEROARIL-PYRIMIDINES INHIBITORAS OF CDK, ITS PREPARATION AND ITS USE AS MEDICATIONS - Google Patents

2-HETEROARIL-PYRIMIDINES INHIBITORAS OF CDK, ITS PREPARATION AND ITS USE AS MEDICATIONS

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Publication number
AR038922A1
AR038922A1 ARP030100819A ARP030100819A AR038922A1 AR 038922 A1 AR038922 A1 AR 038922A1 AR P030100819 A ARP030100819 A AR P030100819A AR P030100819 A ARP030100819 A AR P030100819A AR 038922 A1 AR038922 A1 AR 038922A1
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Argentina
Prior art keywords
alkyl
alkoxy
optionally
hydroxy
halogen
Prior art date
Application number
ARP030100819A
Other languages
Spanish (es)
Inventor
Ulrich Luecking
Martin Krueger
Rolf Jautelat
Olaf Prien
Gerd Siemeister
Alexander Ernst
Original Assignee
Schering Ag
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from DE2002112100 external-priority patent/DE10212100A1/en
Priority claimed from DE10255984A external-priority patent/DE10255984A1/en
Application filed by Schering Ag filed Critical Schering Ag
Publication of AR038922A1 publication Critical patent/AR038922A1/en

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    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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    • A61P25/16—Anti-Parkinson drugs
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    • A61P25/00—Drugs for disorders of the nervous system
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    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A61P31/18—Antivirals for RNA viruses for HIV
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    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
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    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
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    • 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
    • C07D401/12—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 chain containing hetero atoms as chain links
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    • C07D401/14—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 three or more hetero rings
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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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    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur 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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    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

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Abstract

Inhibidores de las quinasas dependientes de las ciclinas, su preparación y su uso como medicamento para el tratamiento de diversas enfermedades. Reivindicación 1: Compuestos de la fórmula general (1), donde: Q es un resto de fórmula (2) ó (3); D, E, G, L, M y T son cada uno, independientemente entre sí, carbono, oxígeno, nitrógeno o azufre, donde al menos debe estar contenido en el anillo un heteroátomo; R1 es hidrógeno, halógeno, alquilo C1-6, alquinilo C1-6, nitro, ciano, heteroarilo o el grupo -COR5, -OCF3, -S-CF3 o -SO2CF3; R2 es hidrógeno, alquilo C1-10, alquenilo C2-10, alquinilo C2-10, arilo, heteroarilo o cicloalquilo C3-7 o alquilo C1-10, alquenilo C2-10, alquinilo C2-10, arilo, heteroarilo o cicloalquilo C3-7, opcionalmente mono polisustituido, igual o diferente, por hidroxi, halógeno, alcoxi C1-6, alquiltio C1-6, amino, ciano, alquilo C1-6, alquenilo C2-6, alcoxi(C1-6)-alquilo(C1-6), alcoxi(C1-6)- alcoxi(C1-6)-alquilo(C1-6), cicloalquilo C3-7, -NHalquilo C1-6, -NHcicloalquilo C3-7, -N(alquilo C1-6)2, -SO(alquilo C1-6), -SO2(alquilo C1-6), alcanoilo C1-6, -CONR3R4, -COR5, alquil(C1-6)OAc, fenilo o por el grupo -R6, el anillo del cicloalquilo C3-7 puede estar opcionalmente interrumpido por uno o varios átomos de nitrógeno, oxígeno y/o azufre y/o puede estar interrumpido en el anillo por uno o varios grupos =C=O y/u opcionalmente pueden estar contenidos en el anillo uno o varios enlaces dobles posibles, y el fenilo, arilo o cicloalquilo C3-7 en sí puede estar opcionalmente mono o polisustituido, igual o diferente, por halógeno, hidroxi, alquilo C1-6, alcoxi C1-6, o por el grupo -CF3 u -OCF3, X es halógeno, oxígeno, azufre o el grupo -NH- o -N(alquilo C1-3)-o X y R2 forman juntos un anillo de cicloalquilo C3-10, que opcionalmente puede contener uno o varios heteroátomos y que opcionalmente puede estar mono o polisustituido por hidroxi, alquilo C1-6, hidroxi-alquilo(C1-6) o halógeno; A y B son cada uno, independientemente entre sí, hidrógeno, hidroxi, halógeno o el grupo -SR7, -S(O)R7, -SO2R7, -NHSO2R7, -CH(OH)R7,-CR7(OH)-R7, alquil(C1-6)P(O)OR3OR4 o -COR7; o Ay B forman juntos un anillo cicloalquilo C3-7 que pueden estar opcionalmente interrumpido por uno o varios átomos de nitrógeno, oxígeno y/o azufre y/o puede estar interrumpido en el anillo por uno o varios grupos =C=O, y/u opcionalmente puede estar contenidos en el anillo uno o varios enlaces dobles posibles y el anillo cicloalquilo C3-7 puede estar opcionalmente mono o polisustituido, igual o diferente, por hidroxi, halógeno, alcoxi C1-6, alquiltio C1-6, amino, ciano, alquilo C1-6, alquenilo C2-6, cicloalquilo C3-7, alcoxi(C1-6)alquilo(C1-6), -NHalquilo C1-6, -N(alquilo C1-6)2, -SO(alquilo C1-6), -SO2(alquilo C1-6), alcanoilo C1-6, -CONR3R4, -COR5, alquil(C1-6)OAc, fenilo, o por el grupo R6, donde el fenilo a su vez puede estar opcionalmente mono o polisustituido, igual o diferente, por halógeno, hidroxi, alquilo C1-6, alcoxi C1-6, o por el grupo -CF3 u -OCF3; R3 y R4 son cada uno, independientemente entre sí, hidrógeno, hidroxi, alcoxi C1-6 o alquilo C1-6 opcionalmente mono o polisustituido, igual o diferente, por hidroxi, alcoxi C1-6, alquiltio C1-6, -N(alquilo C1-6)2, el grupo R6 o -N(alquilo C1-6)R6, R3 y R4 forman juntos un anillo cicloalquilo C3-7 que opcionalmente puede estar interrumpido por uno o varios átomos de nitrógeno, oxígeno y/o azufre y/o puede estar interrumpido en el anillo por uno o varios grupos =C=O, y/u opcionalmente pueden estar contenidos opcionalmente en el anillo uno o varios enlaces dobles posibles; R5 es hidroxi, benzoxi, alquilo C1-6, alquiltio C1-6, o alcoxi C1-6; R6 es un benciltio, feniloxi o anillo cicloalquilo C3-7 opcionalmente mono o polisustituido, igual o diferente, por halógeno, hidroxi, alquilo C1-6, alcoxi(C1-6) o -SO2NR3R4, donde el anillo cicloalquilo C3-7 tiene el significado indicado en R2; R7 es alquilo C1-6, alquenilo C2-6, alquinilo C2-6, bencilo, cicloalquilo C3-7, donde el anillo cicloalquilo C3-7 tiene el significado indicado en R2, o el grupo -NR3R4, o alquilo C1-10, alquenilo C2-10, alquinilo C2-10 o cicloalquilo C3-7, opcionalmente mono o polisustituido, igual o diferente, por hidroxi, alcoxi C1-6, halógeno, fenilo, -NR3R4 o fenilo que, a su vez, puede estar opcionalmente mono o polisustituido, igual o diferente, por halógeno, hidroxi, alquilo C1-6, alcoxi C1-6, halo-alquilo C1-6, halo-alcoxi C1-6, o fenilo que, a su vez, puede estar opcionalmente mono o polisustituido, igual o diferente, por halógeno, hidroxi, alquilo C1-6 o alcoxi C1-6, halo-alquilo C1-6, halo-alcoxi C1-6; y n es 0 ó 1, en caso de que n = 0, entonces X es halógeno, así como los isómeros, diastereómeros, enantiómeros y sales de los mismos.Inhibitors of cyclin-dependent kinases, their preparation and their use as a medicine for the treatment of various diseases. Claim 1: Compounds of the general formula (1), wherein: Q is a residue of formula (2) or (3); D, E, G, L, M and T are each, independently of each other, carbon, oxygen, nitrogen or sulfur, where at least one heteroatom must be contained in the ring; R1 is hydrogen, halogen, C1-6 alkyl, C1-6 alkynyl, nitro, cyano, heteroaryl or the group -COR5, -OCF3, -S-CF3 or -SO2CF3; R2 is hydrogen, C1-10 alkyl, C2-10 alkenyl, C2-10 alkynyl, aryl, heteroaryl or C3-7 cycloalkyl or C1-10 alkyl, C2-10 alkenyl, C2-10 alkynyl, aryl, heteroaryl or C3- cycloalkyl 7, optionally mono-polysubstituted, the same or different, by hydroxy, halogen, C1-6 alkoxy, C1-6 alkylthio, amino, cyano, C1-6 alkyl, C2-6 alkenyl, (C1-6) alkoxy (C1-) alkyl 6), (C1-6) alkoxy - (C1-6) alkoxy-(C1-6) alkyl, C3-7 cycloalkyl, -N C1-6 alkyl, -NH C3-7 cycloalkyl, -N (C1-6 alkyl) 2 , -SO (C1-6 alkyl), -SO2 (C1-6 alkyl), C1-6 alkanoyl, -CONR3R4, -COR5, (C1-6) alkyl OAc, phenyl or by the group -R6, the cycloalkyl ring C3-7 may be optionally interrupted by one or several nitrogen, oxygen and / or sulfur atoms and / or may be interrupted in the ring by one or more groups = C = O and / or optionally may be contained in the ring one or several possible double bonds, and the phenyl, aryl or C3-7 cycloalkyl itself may optionally be mono or polysubstituted, same or different, by halogen, hydroxy, C1-6 alkyl, C1-6 alkoxy, or by the group -CF3 or -OCF3, X is halogen, oxygen, sulfur or the group -NH- or -N (C1-3 alkyl ) -o X and R2 together form a C3-10 cycloalkyl ring, which may optionally contain one or more heteroatoms and which may optionally be mono or polysubstituted by hydroxy, C1-6 alkyl, hydroxy (C1-6) alkyl or halogen ; A and B are each, independently of each other, hydrogen, hydroxy, halogen or the group -SR7, -S (O) R7, -SO2R7, -NHSO2R7, -CH (OH) R7, -CR7 (OH) -R7, (C1-6) alkyl P (O) OR3OR4 or -COR7; or Ay B together form a C3-7 cycloalkyl ring that may be optionally interrupted by one or more nitrogen, oxygen and / or sulfur atoms and / or may be interrupted in the ring by one or more groups = C = O, and / or optionally one or several possible double bonds may be contained in the ring and the C3-7 cycloalkyl ring may optionally be mono or polysubstituted, the same or different, by hydroxy, halogen, C1-6 alkoxy, C1-6 alkylthio, amino, cyano , C1-6 alkyl, C2-6 alkenyl, C3-7 cycloalkyl, (C1-6) alkoxy (C1-6) alkyl, -N C1-6 alkyl, -N (C1-6 alkyl) 2, -SO (C1 alkyl -6), -SO2 (C1-6 alkyl), C1-6 alkanoyl, -CONR3R4, -COR5, (C1-6) alkyl OAc, phenyl, or by the R6 group, where the phenyl in turn may optionally be mono or polysubstituted, the same or different, by halogen, hydroxy, C1-6 alkyl, C1-6 alkoxy, or by the group -CF3 or -OCF3; R3 and R4 are each, independently of each other, hydrogen, hydroxy, C1-6 alkoxy or optionally mono- or polysubstituted C1-6 alkyl, same or different, by hydroxy, C1-6 alkoxy, C1-6 alkylthio, -N (alkyl C1-6) 2, the group R6 or -N (C1-6 alkyl) R6, R3 and R4 together form a C3-7 cycloalkyl ring which may optionally be interrupted by one or more nitrogen, oxygen and / or sulfur atoms and / or it may be interrupted in the ring by one or more groups = C = O, and / or optionally one or several possible double bonds may optionally be contained in the ring; R5 is hydroxy, benzoxy, C1-6 alkyl, C1-6 alkylthio, or C1-6 alkoxy; R 6 is a benzylthio, phenyloxy or C 3-7 cycloalkyl ring optionally mono or polysubstituted, the same or different, by halogen, hydroxy, C 1-6 alkyl, C 1-6 alkoxy or -SO 2 NR 3 R 4, where the C 3-7 cycloalkyl ring has meaning indicated in R2; R 7 is C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, benzyl, C 3-7 cycloalkyl, where the C 3-7 cycloalkyl ring has the meaning indicated in R 2, or the group -NR 3 R 4, or C 1-10 alkyl, C2-10 alkenyl, C2-10 alkynyl or C3-7 cycloalkyl, optionally mono or polysubstituted, the same or different, by hydroxy, C1-6 alkoxy, halogen, phenyl, -NR3R4 or phenyl which, in turn, may optionally be mono or polysubstituted, the same or different, by halogen, hydroxy, C1-6 alkyl, C1-6 alkoxy, halo- C1-6 alkyl, halo-C1-6 alkoxy, or phenyl which, in turn, may optionally be mono or polysubstituted , same or different, by halogen, hydroxy, C 1-6 alkyl or C 1-6 alkoxy, halo C 1-6 alkyl, halo C 1-6 alkoxy; and n is 0 or 1, in case n = 0, then X is halogen, as well as isomers, diastereomers, enantiomers and salts thereof.

ARP030100819A 2002-03-11 2003-03-11 2-HETEROARIL-PYRIMIDINES INHIBITORAS OF CDK, ITS PREPARATION AND ITS USE AS MEDICATIONS AR038922A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE2002112100 DE10212100A1 (en) 2002-03-11 2002-03-11 New 2-aminopyrimidine derivatives are cyclin-dependent kinase inhibitors useful for treating e.g. cancer, autoimmune diseases, cardiovascular diseases, infectious diseases or viral infections
DE10255984A DE10255984A1 (en) 2002-11-26 2002-11-26 New 2-aminopyrimidine derivatives are cyclin-dependent kinase inhibitors useful for treating e.g. cancer, autoimmune diseases, cardiovascular diseases, infectious diseases or viral infections

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AR038922A1 true AR038922A1 (en) 2005-02-02

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EP (1) EP1483260A1 (en)
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