AR071592A1 - Fenoxibenzamidas sustituidas - Google Patents

Fenoxibenzamidas sustituidas

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Publication number
AR071592A1
AR071592A1 ARP090101430A ARP090101430A AR071592A1 AR 071592 A1 AR071592 A1 AR 071592A1 AR P090101430 A ARP090101430 A AR P090101430A AR P090101430 A ARP090101430 A AR P090101430A AR 071592 A1 AR071592 A1 AR 071592A1
Authority
AR
Argentina
Prior art keywords
group
alkyl
independently
cycloalkyl
aryl
Prior art date
Application number
ARP090101430A
Other languages
English (en)
Inventor
Marion Hitchcock
Ingo Hartung
Original Assignee
Bayer Schering Pharma 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
Application filed by Bayer Schering Pharma Ag filed Critical Bayer Schering Pharma Ag
Publication of AR071592A1 publication Critical patent/AR071592A1/es

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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/06—Antipsoriatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
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    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
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    • A61P37/00—Drugs for immunological or allergic disorders
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    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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    • C07C237/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having carbon atoms of carboxamide groups, amino groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
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    • C07C275/34—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms having nitrogen atoms of urea groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C275/36—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms having nitrogen atoms of urea groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring with at least one of the oxygen atoms further bound to a carbon atom of a six-membered aromatic ring, e.g. N-aryloxyphenylureas
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    • C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
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    • C07C311/08—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
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    • C07C311/17—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
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    • C07C311/29—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
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Abstract

Métodos para preparar dichos compuestos, composiciones y combinaciones farmacéuticas que comprenden dichos compuestos, y uso de dichos compuestos para fabricar una composicion farmacéutica para el tratamiento o la profilaxis de una enfermedad, en particular, un trastorno hiper-proliferativo y/o de angiogénesis, como unico agente o en combinacion con otros ingredientes activos. Reivindicacion 1: Un compuesto caracterizado porque responde a la formula general (1), en donde R1 y R2 son iguales o diferentes y son en forma independiente un átomo de hidrogeno, halogeno, un grupo alquilo C1-6, alquenilo C2-6, alquinilo C2-6, o -CN, en donde al menos uno de R1 y R2 es un átomo de halogeno; R3 es, en cada instancia, en forma independiente, un átomo de halogeno, alquilo C1-4 o -CN; q es el entero 0, 1, 2, o 3; R4 es un átomo de hidrogeno o un grupo alquilo C1-6; R5 es un grupo -C(=O)R7, -C(=O)OR7, -C(=O)N(R7)(R8), - NHC(=O)R7, -S(=O)2R7, -NHS(=O)2R7, -S(=O)2NR7R8, -NO2, -CN, o un resto de formula (2), en donde: cada uno de Z1, Z2, Z3 y Z4 es en forma independiente -CH-, -C-alquil C1-6-, -C(=O)-, -S-, -O-, -N- o -NH, de manera que al menos uno de Z1, Z2, Z3 y Z4 es -N- o -NH-; X es -O-, -NH-, -N-alquil C1-6-, -S-, -S(=O)2-, - C(=O)-, -C(=O)O-, o -C(=O)NH-; R6 es -(CR152)n-(CR15 (OR11))-(CR152)m-R9, o -(CH2)n-Y; Y es: a) un grupo arilo, heteroarilo, cicloalquilo o heterocicloalquilo, donde dicho grupo arilo, heteroarilo, cicloalquilo o heterocicloalquilo está sustituido con uno o más grupos -(CH2)oY', en cada instancia de dicho grupo -(CH2)oY': o es el entero 0; y - Y' es, en forma independiente: alquilo C1-6, haloalquilo C1-6, alcoxialquilo C1-6, cicloalquilo, o heterocicloalquilo, o un grupo -ORc, en cada instancia del cual, Rc' es, en forma independiente: un grupo -C(=O)Re, en donde Re se define más adelante, o un grupo S(=O)2Re, en donde Re se define más adelante, o un grupo haloalquilo C1-6, cicloalquilo, heterocicloalquilo, arilo, o heteroarilo, en donde los grupos haloalquilo C1-6, cicloalquilo, heterocicloalquilo, arilo, o heteroarilo están, en forma independiente entre sí, opcionalmente sustituidos una o más veces con: un átomo de halogeno, o un -OH, o un grupo arilo, o un grupo -ORf, en donde Rf es como se define más adelante, o un grupo NRd1Rd2, en donde Rd1 y Rd2 son como se define más adelante, o un grupo -OP(=O) (ORf)2, en donde Rf es como se define más adelante o un grupo NRd1Rd2, como se define más adelante, con las siguientes condiciones: cuando uno de Rd1 y Rd2 es H, luego el otro de Rd1 y Rd2 no es H ni alquilo C1-6, y Rd1 y Rd2 no pueden ser simultáneamente alquilo C1-6; o un grupo NRaS(=O)2Rb, como se define más adelante, con la siguiente condicion: cuando Ra es H, luego Rb no es alquilo C1-6; o un grupo S(=O)2Rb, en donde Rb es como se define más adelante, con las siguientes condiciones cuando Rb es -NRd1Rd2; Rd1 y Rd2 no son ambos H, cuando Rd1 es H, luego Rd2 no es alquilo C1-6, Rd1 y Rd2 no son ambos alquilo C1-6, o un grupo -C(=O)Rb, en donde Rb es como se define más adelante; o b) un grupo arilo, heteroarilo, cicloalquilo o heterocicloalquilo, donde dicho grupo arilo, heteroarilo, cicloalquilo o heterocicloalquilo está sustituido con uno o más grupos -(CH2)oR14, en cada instancia de dicho grupo -(CH2)oR14, o es el entero 1 o 2; y R14 es como se define más adelante; o c) un grupo alquenilo C2-10 o cicloalquenilo C5-10, donde dicho grupo alquenilo C2-10 o cicloalquenilo C5-10 está opcionalmente sustituido con uno o más grupos -(CH2)oR14, en donde o y R14 son como se define más adelante; R7 y R8 son en forma independiente un átomo de hidrogeno, un grupo -N(R12)(R13), -OH, -alcoxi C1-6, -alquilo C1-6, -CF3, -O-(CH2)n-(CH(OR11))-(CH2)m-R9, -O-(CH2)n-cicloalquilo, arilo, heteroarilo, cicloalquilo o heterocicloalquilo, en donde arilo, heteroarilo, cicloalquilo, o heterocicloalquilo están, en forma independiente entre sí, opcionalmente sustituidos con uno o más átomos de halogeno, grupos alquilo C1-6 o alcoxi C1-6; R9 y R10 son en forma independiente -OH, alcoxi C1-6, halogeno, heteroarilo, NRd1Rd2 o -N(R12)(R13); R11, R12 y R13, son en forma independiente un átomo de hidrogeno, un grupo alquilo C1-6, arilo, heteroarilo, cicloalquilo o heterocicloalquilo, en donde alquilo C1-6, arilo, heteroarilo, cicloalquilo, o heterocicloalquilo están, en forma independiente entre sí, opcionalmente sustituidos con uno o más grupos -(CH2)oR14, o R12 y R13, junto con el átomo de nitrogeno al cual están unidos, forman un anillo heterocíclico de 5, 6 o 7 miembros que comprende opcionalmente uno o más heteroátomos adicionales, que comprende opcionalmente uno o más grupos -C(=O)- o -S(=O)2, y que está opcionalmente sustituido con uno o más grupos -(CH2)oR14; R14 es, en cada instancia, en forma independiente, un átomo de halogeno, un grupo alquilo C1-6, haloalquilo C1-6, alcoxialquilo C1-6, cicloalquilo, heterocicloalquilo, -ORc, NRd1Rd2, -CN, -NHS(=O)2H, -NraS(=O)2Rb, -S(=O)2Rb o -C(=O)Rb; R15 es, en cada instancia, en forma independiente, un átomo de hidrogeno o un grupo alquilo C1-6, en donde al menos un grupo R15 es alquilo C1-6; n es, en cada instancia, en forma independiente, el entero 0, 1, 2, 3, o 4; m es, en cada instancia, en forma independiente, el entero 0, 1, o 2; y o es, en cada instancia, en forma independiente, el entero 0, 1, o 2; Ra es, en cada instancia, en forma independiente, un átomo de hidrogeno o un grupo alquilo C1-6; Rb es, en cada instancia, en forma independiente, un grupo -OH, -ORc, -SRc, NRd1Rd2, alquilo C1-6, arilo, heteroarilo, cicloalquilo o heterocicloalquilo, en donde alquilo C1-6, heteroarilo, cicloalquilo y heterocicloalquilo están, en forma independiente entre sí, opcionalmente sustituidos una o más veces con un átomo de halogeno, un grupo -OH, alquilo C1-6, o alcoxi C1-6; Rc es, en cada instancia, en forma independiente, un átomo de hidrogeno, un grupo -C(=O)Re, -S(=O)2Re, alquilo C1-6, haloalquilo C1-6, cicloalquilo, heterocicloalquilo, arilo, o heteroarilo, en donde alquilo C1-6, haloalquilo C1-6, cicloalquilo, heterocicloalquilo, arilo, o heteroarilo, están, en forma independiente entre sí, opcionalmente sustituidos una o más veces con un átomo de halogeno un grupo -OH, arilo, -ORf, NRd1Rd2, o - OP(=O)(ORf)2; Rd1, Rd2, Rd1, Rd2: son, en cada instancia, en forma independiente entre sí, un átomo de H, un grupo alquilo C1-6, cicloalquilo, heterocicloalquilo, arilo, heteroarilo, -C(=O)Re, -S(=O)2Re, o -C(=O)NRg1Rg2, en donde alquilo C1-6, cicloalquilo, heterocicloalquilo, arilo, o heteroarilo, están, en forma independiente entre sí, opcionalmente sustituidos una o más veces, en forma igual o diferente, con un átomo de halogeno, un grupo alquilo C1-6, -OH o arilo, -NRg1Rg2, -ORf, -C(=O)Re, -S(=O)2Re, o -OP(=O)(ORf)2; o Rd1 y Rd2, junto con el átomo de N al cual están unidos, forman un anillo heterocicloalquilo de 3, 4, 5, 6, 7, 8, 9 o 10 miembros, que está opcionalmente sustituido una o más veces, en forma igual o diferente, con un átomo de halogeno, un grupo alquilo C1-6, -NRg1Rg2, -ORf, -C(=O)Re, -S(=O)2Re, o -OP(=O)(ORf)2; y cuya cadena de carbonos está opcionalmente interrumpida una o más veces, en forma igual o diferente, con NH, NRd3, O, o S, y está opcionalmente interrumpida una o más veces, en forma igual o diferente, con un grupo -C(=O)-, -S(=O)-, y/o -S(=O)2-, y contiene opcionalmente uno o más dobles enlaces, Rd3 es un átomo de hidrogeno, un grupo alquilo C1-6, cicloalquilo, heterocicloalquilo, arilo, o heteroarilo, en donde alquilo C1-6 o cicloalquilo están, en forma independiente entre sí, opcionalmente sustituidos una o más veces con un átomo de halogeno, un grupo -OH, alquilo C1-6, cicloalquilo, haloalquilo C1-6 o alcoxi C1-6; Re es un grupo -NRg1Rg2, alquilo C1-6, cicloalquilo, alcoxi C1-6, arilo o heteroarilo; Rf es un átomo de hidrogeno, un grupo -C(=O)Re, alquilo C1-6, haloalquilo C1-6, cicloalquilo, heterocicloalquilo, arilo, o heteroarilo, en donde alquilo C1-6, haloalquilo C1-6, cicloalquilo, heterocicloalquilo, arilo, o heteroarilo están, en forma independiente entre sí, opcionalmente sustituidos una o más veces con un átomo de halogeno, un grupo -OH, alcoxi C1-6, arilo, o -NRg1Rg2; Rg1, Rg2 son, en forma independiente entre sí, un átomo de hidrogeno, un grupo alquilo C1-6, cicloalquilo, heterocicloalquilo, arilo, o heteroarilo; o Rg1 y Rg2 junto con el átomo de nitrogeno al cual están unidos, forman un anillo heterocicloalquilo de 3, 4, 5, 6, 7, 8, 9, o 10 miembros, que está opcionalmente sustituido una o más veces, en forma igual o diferente, con un átomo de halogeno, un grupo -OH, alquilo C1-6, alcoxi C1-6; y cuya cadena de carbonos está opcionalmente interrumpida una o más veces, en forma igual o diferente, con NH, NRa, O, S, y está opcionalmente interrumpida una o más veces, en forma igual o diferente, con un grupo -C(=O)-, -S(=O)- , y/o -S(=O)2-, y contiene opcionalmente uno o más dobles enlaces; con la siguiente condicion: X-R6 no es (O o NH)-(CH2)r-Rr, donde Rr es NRs1Rs2 en donde r =1-4, y Rs1, Rs2 = en forma independiente hidrogeno, alquilo C1-8, o se toman junto con el nitrogeno que están unidos, para formar un anillo cíclico de 3-10 miembros que opcionalmente contiene un átomo de oxígeno o un átomo de azufre o un grupo NH o N-alquilo C1-8; o un tautomero, estereoisomero, sal fisiologicamente aceptable, hidrato, solvato, metabolito o prodroga del mismo.
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US20120263714A1 (en) * 2009-10-21 2012-10-18 Bayer Intellectual Property Gmbh Substituted halophenoxybenzamide derivatives
EA201200651A1 (ru) 2009-11-04 2012-12-28 Новартис Аг Гетероциклические сульфонамидные производные, применимые в качестве ингибиторов мек
CN102020651B (zh) 2010-11-02 2012-07-18 北京赛林泰医药技术有限公司 6-芳基氨基吡啶酮甲酰胺mek抑制剂
KR101599300B1 (ko) 2012-03-14 2016-03-03 시노켐 코포레이션 치환 디페닐아민 화합물 및 항종양제로서의 용도
AU2013337702A1 (en) 2012-11-02 2015-05-21 Merck Patent Gmbh Method of reducing adverse effects in a cancer patient undergoing treatment with a MEK inhibitor
US11465978B2 (en) 2013-09-11 2022-10-11 The Administrators Of The Tulane Educational Fund Anthranilic amides and the use thereof
WO2016155473A1 (zh) * 2015-03-27 2016-10-06 江苏恒瑞医药股份有限公司 一种mek激酶抑制剂的对甲苯磺酸盐、其结晶形式及制备方法
CN110960528A (zh) * 2018-09-30 2020-04-07 四川大学 Ar和bet双重抑制剂及其用途
TW202342018A (zh) 2022-03-04 2023-11-01 美商奇奈特生物製藥公司 Mek激酶抑制劑

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