AR059956A1 - PHENETALONAMINE DERIVATIVES, PREPARATION PROCESSES AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM - Google Patents

PHENETALONAMINE DERIVATIVES, PREPARATION PROCESSES AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM

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Publication number
AR059956A1
AR059956A1 ARP070100967A ARP070100967A AR059956A1 AR 059956 A1 AR059956 A1 AR 059956A1 AR P070100967 A ARP070100967 A AR P070100967A AR P070100967 A ARP070100967 A AR P070100967A AR 059956 A1 AR059956 A1 AR 059956A1
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AR
Argentina
Prior art keywords
ring
alkyl
optionally substituted
halogen
phenyl
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ARP070100967A
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Spanish (es)
Inventor
Michael Stocks
Premji Meghani
Lilian Alcaraz
Andrew Bailey
Garry Pairaudeau
Rhona Cox
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Astrazeneca Ab
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Publication of AR059956A1 publication Critical patent/AR059956A1/en

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    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
    • C07D215/20—Oxygen atoms
    • C07D215/24—Oxygen atoms attached in position 8
    • C07D215/26—Alcohols; Ethers thereof
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    • A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
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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
    • C07D401/12—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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    • 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

Procesos para su preparacion y composiciones farmacéuticas que los contienen y su uso en terapia. Reivindicacion 1: Un compuesto caracterizado porque responde a la formula (1) en donde Ar es un compuesto seleccionado del grupo de formulas (2); M es C(O), NR6, S o CR7R8; R2, R3, R4 y R5 son, en forma independiente, hidrogeno, halogeno, trifluorometilo, ciano, carboxi, hidroxi, nitro, S(O)2R9, NR10S(O)2R11, C(O)NR12R13, NR14C(O)R15, alquilo C1-6, alcoxi C1-6, C(O)(alquilo C1-6) o C(O)2(alquilo C1-6); R3 también puede ser CH2OH o NHS(O)2NR17R18; X es un enlace, CR27R28 o CR29R30CR31R32; Y es CR33R34CR35R36, CR37R38CR39R40CR41R42 o CR43R44CR45R46CR47R48CR49R50; o Y es CR51R52 con la condicion de que E es C(O)O-; Z es un enlace, CR51R52, CR53R54CR55R56, CR57R58CR59R60CR61R62 o CR63R64CR65R66CR67R68CR69R70; A es un grupo cicloalquilamino seleccionado entre un compuesto del grupo de formulas (3), en donde dicho anillo cicloalquilo no está sustituido o está sustituido con 1 o 2 sustituyentes seleccionados en forma independiente entre halogeno, alquilo C1-4 (opcionalmente sustituido con OR116, NR117R118 o NR119C(O)R120), OR19, NR20R21, C(O)NR22R23, NR24C(O)R25, CN, S(O)2R16, o S(O)2NR114R115; cuando A es un grupo cicloalquilamino A está unido a X a través de un átomo de carbono del anillo y a Y a través de NR26; o cuando A es un grupo cicloalquilamino y X es CR29R30CR31R32 A puede estar unido a X a través de NR26 y a Y a través de un átomo de carbono del anillo; cuando X es un enlace A no está conectado a X a través del átomo de carbono del anillo que lleva a NR26; o A es un anillo heterociclilo seleccionado entre un compuesto del grupo de formulas (4) en donde el anillo heterociclilo no está sustituido o está sustituido con 1 o 2 sustituyentes (por ejemplo un sustituyente está en el mismo átomo de carbono del anillo que el que une A a X o Y) seleccionados en forma independiente entre halogeno, alquilo C1-4 (opcionalmente sustituido con OR121, NR122R123 o NR124C(O)R125), OR19, NR20R21, C(O)NR22R23, NR24C(O)R25, CN, S(O)2R126 o S(O)2NR114R115; cuando A es un anillo heterociclilo A está unido a Y a través de un átomo de nitrogeno del anillo; cuando A es un anillo heterociclilo A puede estar unido a X a través de un átomo de carbono del anillo; o, cuando A es heterociclilo con 2 átomos de nitrogeno del anillo y X es CR29R30CR31R32, A puede estar unido a X a través del segundo átomo de nitrogeno del anillo; E es O, S, S(O)2, NR71, C(O)NR72, NR73C(O), C(O)O, S(O)2NR74 o NR75S(O)2; R1 es arilo, ariloxi, NR76-arilo, S(O)2arilo, heteroarilo o cicloalquilo C3-10 (opcionalmente sustituido con alquilo C1-6, halogeno o fenilo), en donde los anillos arilo y heteroarilo están opcionalmente sustituidos con halogeno, ciano, trifluorometilo, fenilo, OCF3, O(CF2)nO, O(CH2)mO, OR78, SR79, NR80R81, C(O)NR82R83, NR84S(O)2R85, C(O)R86, S(O)2R87, S(O)2NR88R89, NR90C(O)R91, C(O)OR92, alquilo C1-6 (opcionalmente sustituido con fluoro, trifluorometilo, fenilo, heteroarilo, OR93, NR94R95, C(O)NR96R97, NR98S(O)2R99, S(O)2R100 o S(O)2NR101R102) o alcoxi C1-6 (opcionalmente sustituido con fluoro, trifluorometilo, fenilo, heteroarilo, OR103, NR104R105, C(O)NR106R107, NR108S(O)2R109, S(O)2R110 o S(O)2NR111R112); en donde 2 sustituyentes sobre el anillo arilo o heteroarilo que es R1 pueden juntarse para formar un anillo de entre 4 y 8 miembros que es carbocíclico o heterocíclico (por ejemplo que contiene 1, 2, 3 o 4 heteroátomos seleccionados en forma independiente entre O, N y S), dicho anillo de entre 4 y 8 miembros está fusionado y está opcionalmente sustituido con halogeno, alquilo C1-4, CF3 o alcoxi C1-4; cuando Z es un enlace E también puede ser C(O) con la condicion de que R1 sea un grupo seleccionado entre un compuesto del grupo de formulas (5) que está opcionalmente sustituido como para R1; n y m son, en forma independiente, 1 o 2; R6, R7, R8, R10, R12, R13, R14, R15, R17, R18, R19, R20, R21, R22, R23, R24, R25, R26, R27, R28, R29, R30, R31, R32, R33, R34, R35, R36, R37, R38, R39, R40, R41, R42, R43, R44, R45, R46, R47, R48, R49, R50, R51, R52, R53, R54, R55, R56, R57, R58, R59, R60, R61, R62, R63, R64, R65, R66, R67, R68, R69, R70, R71, R72, R73, R74, R75, R76, R77, R78, R79, R80, R81, R82, R83, R84, R86, R88, R89, R90, R91, R92, R93, R94, R95, R96, R97, R98, R101, R102, R103, R104, R105, R106, R107, R108, R111, R112, R113, R114, R115, R116, R117, R118, R119, R120, R121, R122, R123, R124 y R125 son, en forma independiente, hidrogeno o alquilo C1-6; R52 también puede ser fenilo; R72 también puede ser fenil(alquilo C1-4) (por ejemplo bencilo); R9, R11, R16, R85, R87, R99, R100, R109, R110 y R126 son, en forma independiente, alquilo C1-6; con la condicion de que cuando R1 es ariloxi, NR76-arilo o S(O)2arilo, y E es O, S, S(O)2, NR71, C(O)NR72, S(O)2NR74 o NR75S(O)2, entonces Z es CR53R54CR55R56, CR57R58CR59R60CR61R62 o CR63R64CR65R66CR67R68CR69R70; o una sal aceptable para uso farmacéutico del mismo.Processes for their preparation and pharmaceutical compositions containing them and their use in therapy. Claim 1: A compound characterized in that it responds to formula (1) wherein Ar is a compound selected from the group of formulas (2); M is C (O), NR6, S or CR7R8; R2, R3, R4 and R5 are, independently, hydrogen, halogen, trifluoromethyl, cyano, carboxy, hydroxy, nitro, S (O) 2R9, NR10S (O) 2R11, C (O) NR12R13, NR14C (O) R15 , C1-6 alkyl, C1-6 alkoxy, C (O) (C1-6 alkyl) or C (O) 2 (C1-6 alkyl); R3 can also be CH2OH or NHS (O) 2NR17R18; X is a link, CR27R28 or CR29R30CR31R32; Y is CR33R34CR35R36, CR37R38CR39R40CR41R42 or CR43R44CR45R46CR47R48CR49R50; or Y is CR51R52 with the proviso that E is C (O) O-; Z is a link, CR51R52, CR53R54CR55R56, CR57R58CR59R60CR61R62 or CR63R64CR65R66CR67R68CR69R70; A is a cycloalkylamino group selected from a compound of the group of formulas (3), wherein said cycloalkyl ring is not substituted or substituted with 1 or 2 substituents independently selected from halogen, C1-4 alkyl (optionally substituted with OR116, NR117R118 or NR119C (O) R120), OR19, NR20R21, C (O) NR22R23, NR24C (O) R25, CN, S (O) 2R16, or S (O) 2NR114R115; when A is a cycloalkylamino group A is linked to X through a carbon atom of the ring and Y through NR26; or when A is a cycloalkylamino group and X is CR29R30CR31R32 A can be linked to X through NR26 and Y through a ring carbon atom; when X is a link A is not connected to X through the carbon atom of the ring leading to NR26; or A is a heterocyclyl ring selected from a compound of the group of formulas (4) wherein the heterocyclyl ring is not substituted or is substituted with 1 or 2 substituents (for example a substituent is on the same carbon atom of the ring as the one binds A to X or Y) independently selected from halogen, C1-4 alkyl (optionally substituted with OR121, NR122R123 or NR124C (O) R125), OR19, NR20R21, C (O) NR22R23, NR24C (O) R25, CN , S (O) 2R126 or S (O) 2NR114R115; when A is a heterocyclyl ring A is attached to Y through a ring nitrogen atom; when A is a heterocyclyl ring A can be attached to X through a carbon atom of the ring; or, when A is heterocyclyl with 2 ring nitrogen atoms and X is CR29R30CR31R32, A may be attached to X through the second ring nitrogen atom; E is O, S, S (O) 2, NR71, C (O) NR72, NR73C (O), C (O) O, S (O) 2NR74 or NR75S (O) 2; R1 is aryl, aryloxy, NR76-aryl, S (O) 2aryl, heteroaryl or C3-10 cycloalkyl (optionally substituted with C1-6 alkyl, halogen or phenyl), wherein the aryl and heteroaryl rings are optionally substituted with halogen, cyano , trifluoromethyl, phenyl, OCF3, O (CF2) nO, O (CH2) mO, OR78, SR79, NR80R81, C (O) NR82R83, NR84S (O) 2R85, C (O) R86, S (O) 2R87, S (O) 2NR88R89, NR90C (O) R91, C (O) OR92, C1-6 alkyl (optionally substituted with fluoro, trifluoromethyl, phenyl, heteroaryl, OR93, NR94R95, C (O) NR96R97, NR98S (O) 2R99, S (O) 2R100 or S (O) 2NR101R102) or C1-6 alkoxy (optionally substituted with fluoro, trifluoromethyl, phenyl, heteroaryl, OR103, NR104R105, C (O) NR106R107, NR108S (O) 2R109, S (O) 2R110 or S (O) 2NR111R112); wherein 2 substituents on the aryl or heteroaryl ring which is R1 can be joined to form a ring of between 4 and 8 members that is carbocyclic or heterocyclic (for example containing 1, 2, 3 or 4 heteroatoms independently selected from O, N and S), said 4 to 8 member ring is fused and is optionally substituted with halogen, C1-4 alkyl, CF3 or C1-4 alkoxy; when Z is a bond E can also be C (O) with the proviso that R1 is a group selected from a compound of the group of formulas (5) that is optionally substituted as for R1; n and m are, independently, 1 or 2; R6, R7, R8, R10, R12, R13, R14, R15, R17, R18, R19, R20, R21, R22, R23, R24, R25, R26, R27, R28, R29, R30, R31, R32, R33, R34, R35, R36, R37, R38, R39, R40, R41, R42, R43, R44, R45, R46, R47, R48, R49, R50, R51, R52, R53, R54, R55, R56, R57, R58, R59, R60, R61, R62, R63, R64, R65, R66, R67, R68, R69, R70, R71, R72, R73, R74, R75, R76, R77, R78, R79, R80, R81, R82, R83, R84, R86, R88, R89, R90, R91, R92, R93, R94, R95, R96, R97, R98, R101, R102, R103, R104, R105, R106, R107, R108, R111, R112, R113, R114, R115, R116, R117, R118, R119, R120, R121, R122, R123, R124 and R125 are, independently, hydrogen or C1-6 alkyl; R52 can also be phenyl; R72 may also be phenyl (C1-4 alkyl) (for example benzyl); R9, R11, R16, R85, R87, R99, R100, R109, R110 and R126 are, independently, C1-6 alkyl; with the proviso that when R1 is aryloxy, NR76-aryl or S (O) 2aryl, and E is O, S, S (O) 2, NR71, C (O) NR72, S (O) 2NR74 or NR75S (O ) 2, then Z is CR53R54CR55R56, CR57R58CR59R60CR61R62 or CR63R64CR65R66CR67R68CR69R70; or a salt acceptable for pharmaceutical use thereof.

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