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AR053992A1 - CHEMICAL COMPOUNDS WITH ANTI-TARGET ACTIVITY, A PROCEDURE FOR THEIR PREPARATION, ITS USE IN THE PREPARATION OF MEDICINES AND PHARMACEUTICAL COMPOSITION. - Google Patents

CHEMICAL COMPOUNDS WITH ANTI-TARGET ACTIVITY, A PROCEDURE FOR THEIR PREPARATION, ITS USE IN THE PREPARATION OF MEDICINES AND PHARMACEUTICAL COMPOSITION.

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Publication number
AR053992A1
AR053992A1 ARP050105491A ARP050105491A AR053992A1 AR 053992 A1 AR053992 A1 AR 053992A1 AR P050105491 A ARP050105491 A AR P050105491A AR P050105491 A ARP050105491 A AR P050105491A AR 053992 A1 AR053992 A1 AR 053992A1
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AR
Argentina
Prior art keywords
alkyl
amino
carbamoyl
sulfamoyl
optionally substituted
Prior art date
Application number
ARP050105491A
Other languages
Spanish (es)
Inventor
L Almeida
B Aquila
D Cook
S Cowen
L Dakin
J Ezjuthachan
S Ioannidis
J Lee
S Lee
P Lyne
T Pontz
D Scott
M Su
X Zheng
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Astrazeneca Ab
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Publication of AR053992A1 publication Critical patent/AR053992A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C07D213/72—Nitrogen atoms
    • C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C07D213/72—Nitrogen atoms
    • C07D213/76—Nitrogen atoms to which a second hetero atom is attached
    • 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
    • C07D401/12—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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—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
    • 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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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Estos compuestos poseen actividad inhibidora de la CSF-1R quinasa y son en consecuencia utiles por su actividad anticancerosa y por lo tanto en métodos de tratamiento del cuerpo humano o animal. La presente también se relaciona con procesos para la fabricacion de dichos compuestos químicos, de las composiciones farmacéuticas que los contienen y de su uso en la fabricacion de medicamentos aplicables a la produccion de un efecto anticanceroso en un animal de sangre caliente, tal como el ser humano. Reivindicacion 1: Un compuesto de la formula (1) caracterizado porque el anillo A es carbociclilo o heterociclilo, e donde si dicho heterociclilo contiene una porcion -NH- dicho N puede estar opcionalmente sustituido por un grupo seleccionado entre R5; R1 es un sustituyente sobre C y se selecciona entre halo, nitro, cian, hidroxi, trifluorometoxi, amino, carboxi, carbamoílo, mercapto, sulfamoílo, C1-6 alquilo, C2-6 alquenilo, C2-6 alquinilo, C1-6 alcoxi, C1-6 alcanoílo, C1-6 alcanoiloxi, N-(C1-6 alquil)-amino, N,N-(C1-6 alquil)2amino, C1-6 alcanoilamino, N-(C1-6 alquil)carbamoílo, N,N-(C1-6 alquil)2carbamoílo, C1-6alquilS(O)a en donde a es entre 0 y 2, C1-6 alcoxicarbonilo, C1-6 alcoxicarbonilamino, N-(C1-6 alquil)sulfamoílo, N,N-(C1-6 alquil)2sulfamoílo, N-(C1-6 alquil)-N-(C1-6 alcoxi)sulfamoílo, N,N'-(C1-6 alquil)2ureido, N,N'-(C1-6 alquil)2ureido, N-(C1-6 alquil)-N',N'-(C1-6 alquil)2ureido, C1-6 alquilsulfonilamino, carbociclil-R6- heterociclil-R7- ; en donde R1 puede estar opcionalmente sustituido sobre C por uno o más R8; y en donde si dicho heterociclilo contiene una porcion -NH- dicho N puede estar opcionalmente sustituido por un grupo seleccionado entre R9; n se selecciona entre 0-4; en donde los valores de R1 pueden ser iguales o diferentes; R2 se selecciona entre H, halo, nitro, ciano, hidroxi, trifluorometoxi, amino, carboxi, carbamoílo, mercapto, sulfamoílo, C1-6 alquilo, C2-6 alquenilo, C2-6 alquinilo, C1-6 alcoxi, C1-6 alcanoílo, C1-6 alcanoiloxi, N-(C1-6 alquil)-amino, N,N-(C1-6 alquil)2amino, C1-6 alcanoilamino, N-(C1-6 alquil)carbamoílo, N,N-(C1-6 alquil)2carbamoílo, C1-6alquilS(O)a en donde a es entre 0 y 2, C1-6 alcoxicarbonilo, N-(C1-6 alquil)sulfamoílo, N,N- (C1-6 alquil)2sulfamoílo, C1-6 alquilsulfonilamino, carbociclil-R10- o heterociclil-R11-; en donde R2 puede estar opcionalmente sustituido sobre C por un o más R12; y en donde si dicho heterociclilo contiene una porcion -NH- dicho N puede estar opcionalmente sustituido por un grupo seleccionado entre R13; R3 se selecciona entre halo, hidroxi, cano, metilo, metoxi o hidroximetilo; R4 se selecciona entre halo, nitro, ciano, hidroxi, trifluorometoxi, amino, carboxi, carbamoílo, mercapto, sulfamoílo, ureido, C1-6 alquilo, C2-6 alquenilo, C2-6 alquinilo, C1-6 alcoxi, C1-6 alcanoílo, C1-6 alcanoiloxi, N-(C1-6 alquil)-amino, N,N-(C1-6 alquil)2amino, C1-6 alcanoilamino, N-(C1-6 alquil)carbamoílo, N,N-(C1-6 alquil)2carbamoílo, C1- 6alquilS(O)a en donde a es entre 0 y 2, C1-6 alcoxicarbonilo, N-(C1-6 alquil)sulfamoílo, N,N-(C1-6 alquil)2sulfamoílo, C1-6 alquilsulfonilamino carbociclil- R14- o heterociclil-R15-; en donde R4 puede estar opcionalmente sustituido sobre C por uno o más R16; y en donde si dicho heterociclilo contiene una porcion -NH- dicho N puede estar opcionalmente sustituido por un grupo seleccionado entre R17; m se selecciona entre 0-4; en donde los valores de R4 pueden ser iguales o diferentes; R8 y R12 se seleccionan en forma independiente entre halo, nitro, ciano, hidroxi, trifluorometoxi, amino, carboxi, carbamoílo, mercapto, sulfamoílo, C1-6 alquilo, C2-6 alquenilo, C2-6 alquinilo, C1-6 alcoxi, C1-6 alcanoílo, C1-6 alcanoiloxi, N-(C1-6 alquil)- amino, N,N-(C1-6 alquil)2amino, N-(C1-6 alquil)-N-(C1-6 alcoxi)amino, C1-6 alcanoilamino, N-(C1-6 alquil)carbamoílo, N,N-(C1-6 alquil)2carbamoílo, C1-6alquilS(O)a en donde a es entre 0 y 2, C1-6 alcoxicarbonilo, N-(C1-6 alquil)sulfamoílo, N,N-(C1-6 alquil)2sulfamoílo, C1-6 alquilsulfonilamino, carbociclil-R18- o heterociclil-R19-; en donde R8 y R12 en forma independiente entre sí pueden estar opcionalmente sustituidos sobre C por uno más R20; y donde si dicho heterociclilo contiene una porcion -NH- dicho N puede estar opcionalmente sustituido por un grupo seleccionado entre R21; R16 se selecciona entre halo, nitro, ciano, hidroxi, trifluorometoxi, amino, carboxi, carbamoílo, mercapto, sulfamoílo, C1-6 alquilo, C2-6 alquenilo, C2-6 alquinilo, C1-6 alcoxi, C1-6 alcanoílo, C1-6 alcanoiloxi, N-(C1-6 alquil)-amino, N,N-(C1-6 alquil)2amino, C1-6 alcanoilamino, N-(C1-6 alquil)carbamoílo, N,N-(C1-6 alquil)2carbamoílo, C1-6alquilS(O)a en donde a es entre 0 y 2, C1-6 alcoxicarbonilo, N- (C1-6 alquil)sulfamoílo, N,N-(C1-6 alquil)2sulfamoílo, C1-6 alquilsulfonilamino, carbociclil-R22- o heterociclil-R23-; en donde R16 puede estar opcionalmente sustituido sobre C por uno más R24; y en donde si dicho heterociclilo contiene una porcion - NH- dicho N puede estar opcionalmente sustituido por un grupo seleccionado entre R25; R6, R7, R10, R11, R14, R15, R18, R19, R22 y R23 se seleccionan en forma independiente entre un enlace directo, -O-, -N(R26)-, -C(O)-, -N(R27)C(O)-, -C(O)N(R28)-, - S(O)s-, -SO2N(R29)- o -N(R30)SO2-; en donde R26, R27, R28, R29 y R30 se seleccionan en forma independiente entre H o C1-6 alquilo y s es 0-2; R5, R9, R13, R17, R21 y R25 se seleccionan en forma independiente entre C1-6 alquilo, C1-6 alcanoílo, C1-6 alquilsulfonilo, C1-6 alcoxicarbonilo, carbamoílo, N-(C1-6 alquil)carbamoílo, N,N-(C1-6 alquil)carbamoílo, bencilo, benciloxicarbonilo, benzoílo y fenilsulfonilo; R20 y R24 se seleccionan en forma independiente entre halo, nitro, ciano, hidroxi, trifluorometoxi, trifluorometilo, amino, carboxi, carbamoílo, mercapto, sulfamoílo, metilo, etilo, metoxi, etoxi, acetilo, acetoxi, metilamino, etilamino, dimetilamino, dietilamino, N-metil-N-etilamino, acetilamino, N-metilcarbamoílo, N- etilcarbamoílo, N,N-dimetilcarbamoílo, N,N-dietilcarbamoílo, N-metil-N-etilcarbamoílo, fenilo, metiltio, etiltio, metilsulfinilo, etilsulfinilo, mesilo, etilsulfonilo, metoxicarbonilo, etoxicarbonilo, N-metilsulfamoílo, N-etilsulfamoílo, N,N- dimetilsulfamoílo, N,N-dietilsulfamoílo o N-metil-N-etilsulfamoílo; o una de sus sales aceptables para uso farmacéutico; con la salvedad de que dicho compuesto no sea: N-[4-cloro-3-({[6-(4-metilpiperazin-1-il)piridin-3-il]amino}carbonil)fenil]-2- morfolin-4-ilisonicotinamida; N-[4-cloro-3-({[6-(4-etilpiperazin-1-il)piridin-3-il]amino}carbonil)fenil]-2-morfolin-4-ilisonicotinamida; N-[4-cloro-3-({[6-(4-dimetilamino)propil](metil)amino]piridin-3-il}amino)carbonil]fenil}-2-morfolin-4- ilisonicotinamida; N-[4-cloro-3-({[6-(4-dimetilamino)etil](metil)amino]piridin-3-il}amino)carbonil]fenil}-2-morfolin-4-ilisonicotinamida; o N-[4-cloro-3-({[6-(4-metil-1,4-diazepan-1-il)piridin-3-il]amino}carbonil)fenil]-2-morfolin-4- ilisonicotinamida;These compounds possess CSF-1R kinase inhibitory activity and are consequently useful for their anticancer activity and therefore in methods of treating the human or animal body. This also relates to processes for the manufacture of said chemical compounds, the pharmaceutical compositions that contain them and their use in the manufacture of medicines applicable to the production of an anticancer effect in a warm-blooded animal, such as being human. Claim 1: A compound of the formula (1) characterized in that the ring A is carbocyclyl or heterocyclyl, and where said heterocyclyl contains a portion -NH- said N may be optionally substituted by a group selected from R5; R1 is a substituent on C and is selected from halo, nitro, cyan, hydroxy, trifluoromethoxy, amino, carboxy, carbamoyl, mercapto, sulfamoyl, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 alkoxy, C1-6 alkanoyl, C1-6 alkanoyloxy, N- (C1-6 alkyl) -amino, N, N- (C1-6 alkyl) 2amino, C1-6 alkanoylamino, N- (C1-6 alkyl) carbamoyl, N, N- (C1-6 alkyl) 2carbamoyl, C1-6alkyl (O) a where a is between 0 and 2, C1-6 alkoxycarbonyl, C1-6 alkoxycarbonylamino, N- (C1-6 alkyl) sulfamoyl, N, N- (C1-6 alkyl) 2sulfamoyl, N- (C1-6 alkyl) -N- (C1-6 alkoxy) sulfamoyl, N, N '- (C1-6 alkyl) 2ureido, N, N' - (C1-6 alkyl ) 2ureido, N- (C1-6 alkyl) -N ', N' - (C1-6 alkyl) 2ureido, C1-6 alkylsulfonylamino, carbocyclyl-R6-heterocyclyl-R7-; wherein R1 may be optionally substituted on C by one or more R8; and wherein if said heterocyclyl contains a portion -NH- said N may be optionally substituted by a group selected from R9; n is selected from 0-4; where the values of R1 can be the same or different; R2 is selected from H, halo, nitro, cyano, hydroxy, trifluoromethoxy, amino, carboxy, carbamoyl, mercapto, sulfamoyl, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 alkoxy, C1-6 alkanoyl , C1-6 alkanoyloxy, N- (C1-6 alkyl) -amino, N, N- (C1-6 alkyl) 2amino, C1-6 alkanoylamino, N- (C1-6 alkyl) carbamoyl, N, N- (C1 -6 alkyl) 2carbamoyl, C1-6alkyl (O) a where a is between 0 and 2, C1-6 alkoxycarbonyl, N- (C1-6 alkyl) sulfamoyl, N, N- (C1-6 alkyl) 2sulfamoyl, C1 -6 alkylsulfonylamino, carbocyclyl-R10- or heterocyclyl-R11-; wherein R2 may be optionally substituted on C by one or more R12; and wherein if said heterocyclyl contains a portion -NH- said N may be optionally substituted by a group selected from R13; R3 is selected from halo, hydroxy, cano, methyl, methoxy or hydroxymethyl; R4 is selected from halo, nitro, cyano, hydroxy, trifluoromethoxy, amino, carboxy, carbamoyl, mercapto, sulfamoyl, ureido, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 alkoxy, C1-6 alkanoyl , C1-6 alkanoyloxy, N- (C1-6 alkyl) -amino, N, N- (C1-6 alkyl) 2amino, C1-6 alkanoylamino, N- (C1-6 alkyl) carbamoyl, N, N- (C1 -6 alkyl) 2carbamoyl, C1-6alkyl (O) a where a is between 0 and 2, C1-6 alkoxycarbonyl, N- (C1-6 alkyl) sulfamoyl, N, N- (C1-6 alkyl) 2sulfamoyl, C1 -6 alkylsulfonylamino carbocyclyl-R14- or heterocyclyl-R15-; wherein R4 may be optionally substituted on C by one or more R16; and wherein if said heterocyclyl contains a portion -NH- said N may be optionally substituted by a group selected from R17; m is selected from 0-4; where the values of R4 can be the same or different; R8 and R12 are independently selected from halo, nitro, cyano, hydroxy, trifluoromethoxy, amino, carboxy, carbamoyl, mercapto, sulfamoyl, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 alkoxy, C1 -6 alkanoyl, C1-6 alkanoyloxy, N- (C1-6 alkyl) -amino, N, N- (C1-6 alkyl) 2amino, N- (C1-6 alkyl) -N- (C1-6 alkoxy) amino , C1-6 alkanoylamino, N- (C1-6 alkyl) carbamoyl, N, N- (C1-6 alkyl) 2carbamoyl, C1-6alkyl (O) a where a is between 0 and 2, C1-6 alkoxycarbonyl, N - (C1-6 alkyl) sulfamoyl, N, N- (C1-6 alkyl) 2sulfamoyl, C1-6 alkylsulfonylamino, carbocyclyl-R18- or heterocyclyl-R19-; wherein R8 and R12 independently of each other may optionally be substituted on C by one plus R20; and where if said heterocyclyl contains a portion -NH- said N may be optionally substituted by a group selected from R21; R16 is selected from halo, nitro, cyano, hydroxy, trifluoromethoxy, amino, carboxy, carbamoyl, mercapto, sulfamoyl, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 alkoxy, C1-6 alkanoyl, C1 -6 alkanoyloxy, N- (C1-6 alkyl) -amino, N, N- (C1-6 alkyl) 2amino, C1-6 alkanoylamino, N- (C1-6 alkyl) carbamoyl, N, N- (C1-6 alkyl) 2carbamoyl, C1-6alkyl (O) a where a is between 0 and 2, C1-6 alkoxycarbonyl, N- (C1-6 alkyl) sulfamoyl, N, N- (C1-6 alkyl) 2sulfamoyl, C1-6 alkylsulfonylamino, carbocyclyl-R22- or heterocyclyl-R23-; wherein R16 may be optionally substituted on C by one plus R24; and wherein if said heterocyclyl contains a portion-NH- said N may be optionally substituted by a group selected from R25; R6, R7, R10, R11, R14, R15, R18, R19, R22 and R23 are independently selected from a direct link, -O-, -N (R26) -, -C (O) -, -N ( R27) C (O) -, -C (O) N (R28) -, - S (O) s-, -SO2N (R29) - or -N (R30) SO2-; wherein R26, R27, R28, R29 and R30 are independently selected from H or C1-6 alkyl and s is 0-2; R5, R9, R13, R17, R21 and R25 are independently selected from C1-6 alkyl, C1-6 alkanoyl, C1-6 alkylsulfonyl, C1-6 alkoxycarbonyl, carbamoyl, N- (C1-6 alkyl) carbamoyl, N , N- (C1-6 alkyl) carbamoyl, benzyl, benzyloxycarbonyl, benzoyl and phenylsulfonyl; R20 and R24 are independently selected from halo, nitro, cyano, hydroxy, trifluoromethoxy, trifluoromethyl, amino, carboxy, carbamoyl, mercapto, sulfamoyl, methyl, ethyl, methoxy, ethoxy, acetyl, acetoxy, methylamino, ethylamino, dimethylamino, diethylamino , N-methyl-N-ethylamino, acetylamino, N-methylcarbamoyl, N-ethylcarbamoyl, N, N-dimethylcarbamoyl, N, N-diethylcarbamoyl, N-methyl-N-ethylcarbamoyl, phenyl, methylthio, ethylthio, methylsulfinyl, mesylsulfinyl , ethylsulfonyl, methoxycarbonyl, ethoxycarbonyl, N-methylsulfamoyl, N-ethylsulfamoyl, N, N-dimethylsulfamoyl, N, N-diethylsulfamoyl or N-methyl-N-ethyl-sulfamoyl; or one of its salts acceptable for pharmaceutical use; with the proviso that said compound is not: N- [4-chloro-3 - ({[6- (4-methylpiperazin-1-yl) pyridin-3-yl] amino} carbonyl) phenyl] -2- morpholin- 4-ilisonicotinamide; N- [4-chloro-3 - ({[6- (4-ethylpiperazin-1-yl) pyridin-3-yl] amino} carbonyl) phenyl] -2-morpholin-4-ylisonicotinamide; N- [4-chloro-3 - ({[6- (4-dimethylamino) propyl] (methyl) amino] pyridin-3-yl} amino) carbonyl] phenyl} -2-morpholin-4-ylisonicotinamide; N- [4-chloro-3 - ({[6- (4-dimethylamino) ethyl] (methyl) amino] pyridin-3-yl} amino) carbonyl] phenyl} -2-morpholin-4-ylisonicotinamide; or N- [4-chloro-3 - ({[6- (4-methyl-1,4-diazepan-1-yl) pyridin-3-yl] amino} carbonyl) phenyl] -2-morpholin-4- ylisonicotinamide ;

ARP050105491A 2004-12-22 2005-12-22 CHEMICAL COMPOUNDS WITH ANTI-TARGET ACTIVITY, A PROCEDURE FOR THEIR PREPARATION, ITS USE IN THE PREPARATION OF MEDICINES AND PHARMACEUTICAL COMPOSITION. AR053992A1 (en)

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