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AR041734A1 - Compuestos de alquino con efecto antagonico de la hcm y medicamentos que contienen estos compuestos - Google Patents

Compuestos de alquino con efecto antagonico de la hcm y medicamentos que contienen estos compuestos

Info

Publication number
AR041734A1
AR041734A1 ARP030103994A ARP030103994A AR041734A1 AR 041734 A1 AR041734 A1 AR 041734A1 AR P030103994 A ARP030103994 A AR P030103994A AR P030103994 A ARP030103994 A AR P030103994A AR 041734 A1 AR041734 A1 AR 041734A1
Authority
AR
Argentina
Prior art keywords
alkyl
amino
group
phenyl
atoms
Prior art date
Legal status (The legal status 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 status listed.)
Suspension/Interruption
Application number
ARP030103994A
Other languages
English (en)
Inventor
Dirk Stenkamp
Lustenberger Philipp Dr
Stephan Georg Mueller
Gerald Juergen Roth
Thorsten Lehmann-Lintz
Rudolf Klaus Dr
Kirsten Arndt
Ralf R H Lotz
Martin Lenter
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Boehringer Ingelheim Pharma GmbH Co KG
Original Assignee
Boehringer Ingelheim Pharma GmbH Co KG
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 Boehringer Ingelheim Pharma GmbH Co KG filed Critical Boehringer Ingelheim Pharma GmbH Co KG
Publication of AR041734A1 publication Critical patent/AR041734A1/es
Suspension/Interruption legal-status Critical Current

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    • 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
    • C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
    • C07D213/46—Oxygen atoms
    • C07D213/48—Aldehydo radicals
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    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4418—Non condensed pyridines; Hydrogenated derivatives thereof having a carbocyclic group directly attached to the heterocyclic ring, e.g. cyproheptadine
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    • 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
    • C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
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    • 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
    • C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
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    • 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
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Abstract

La presente se refiere a compuestos de alquino de fórmula general (1) en la cual R1, R2 son, en forma independiente entre sí, H, un grupo alquilo C1-8 o cicloalquilo C3-7 opcionalmente sustituido con el radical R11, donde un grupo -CH2- puede estar reemplazado en la posición 3 o 4 de un grupo cicloalquilo de 5, 6 o 7 miembros por -O-, -S- o -NR13-, o un radical fenilo o piridinilo opcionalmente mono o polisustituido con el radical R12 y/o monosustituido con nitro, o R1 y R2 forman un puente alquileno C2-8, en el que uno o dos grupos -CH2- pueden estar reemplazados, en forma independiente entre sí, por -CH=N- o -CH=CH- y/o uno o dos grupo -CH2-, en forma independiente entre sí, pueden estar reemplazados por -O-; -S-; -SO;-(SO2)-, -C=N-R18, -C=N-O-R18, -CO-, -C(=CH2)- o -NR13- de modo tal que los heteroátomos no estén unidos entre sí en forma directa; donde en el puente alquileno definido con anterioridad pueden estar reemplazados uno o varios átomos de H por R14, y donde el puente alquileno definido con anterioridad puede estar sustituido con uno o dos grupos Cy carbo- o heterocíclicos iguales o diferentes de modo tal que la unión entre el puente alquileno y el grupo Cy se realiza a través de un enlace simple o doble; a través de un átomo de C común, formando un sistema de anillos espirocíclicos; a través de dos átomos de C y/o N comunes adyacentes, formando un sistema de anillos bicíclicos condensados o a través de tres o más átomos de C y/ o N, formando un sistema de anillos en puente; X es un enlace simple o un puente alquileno C1-6, en el que un grupo -CH2- puede estar reemplazado por -CH=CH- o -C:::C- y/o uno o dos grupos -CH2-, en forma independiente entre sí, pueden estar reemplazados por -O-; -S-; -(SO)-; -(SO2)-;-CO- o -NR4- de modo tal que cada uno de dos átomos de O, S o N o un átomo de O con un átomo de S no estén unidos entre sí de forma directa, donde el puente X puede estar unido con R1 incluyendo el átomo de N unido con R1 y X, formando un grupo heterocíclico, donde el puente X también puede estar unido adicionalmente con R2, incluyendo el átomo de N unido con R2 y X, formando un grupo heterocíclico, y donde los átomos de C o un átomo de C y de N del puente alquileno pueden estar unidos entre sí a través de un puente alquileno C1-4 adicional, y donde un átomo de C puede estar sustituido con R10 y/o uno o dos átomos de C pueden estar sustituidos con uno o dos sustituyentes iguales o diferentes seleccionados entre alquilo C1-6, alquenilo C2-6, alquinilo C2-6, cicloalquilo C3-7, cicloalquil C3-7-alquilo C1-3, cicloalquenilo C4-7 y cicloalquenil C4-7-alquilo C1-3, donde dos sustituyentes de alquilo y/o alquenilo pueden estar unidos entre sí, formando un sistema de anillos carbocíclicos, y W, Z son, en forma independiente entre sí, un enlace simple o un puente alquileno C1-4, donde en el grupo W y/o Z un grupo -CH2- no adyacente con el grupo -C:::C- puede estar reemplazado por -O- o -NR5-, y donde dos átomos de C adyacentes o un átomo de C y un átomo de N adyacente pueden estar unidos entre sí con un puente de alquileno C1-4 adicional, y donde en el puente alquileno y/o en el puente alquileno adicional un átomo de C puede estar sustituido con R10 y/o uno o dos átomos de C en forma independiente entre sí, pueden estar sustituidos con uno o dos radicales alquilo C1-6 iguales o diferentes, donde dos radicales alquilo pueden estar unidos entre sí, formando un anillo carbocíclico, e Y tiene uno de los significados indicados para Cy, donde R1 puede estar unido con Y incluyendo el grupo X y el átomo de N unido con R1 y X, formando un grupo heterocíclico condensado en Y, y/o donde X puede estar unido con Y, formando un grupo carbo- o heterocíclico condensado en Y, y A tiene uno de los significados indicados para Cy y B tiene uno de los significados indicados para Cy o es alquilo C1-6, alquenilo C1-6, alquinilo C1-6, cicloalquil C3-7-alquilo C1-3, cicloalquenil C3-7-alquilo C1-3, cicloalquil C3-7-alquenilo C1-3 o cicloalquil C3-7-alquinilo C1-3, donde uno o varios átomos de C pueden estar mono o polisustituidos con halógeno y/o monosustituidos con hidroxi o ciano y/o grupos cíclicos pueden estar mono o polisustituidos con R20; Cy es un grupo carbo- o heterocíclico seleccionado de uno de los siguientes significados: un grupo carbocíclico saturado de 3 a 7 miembros, un grupo carbocíclico insaturado de 4 a 7 miembros, un grupo fenilo, un grupo heterocíclico saturado de 4 a 7 miembros o insaturado de 5 a 7 miembros con un átomo de N, O o S como heteroátomo, un grupo heterocíclico saturado o insaturado de 5 a 7 miembros con dos o varios átomos de N o con uno o dos átomos de N y un átomo de O o de S como heteroátomos, un grupo heterocíclico aromático de 5 o 6 miembros con uno o varios heteroátomos iguales o diferentes seleccionados entre N, O y/o S, donde los grupos de 4, 5, 6 o 7 miembros indicados con anterioridad pueden estar unidos a través de dos átomos de C comunes adyacentes en forma condensada con un anillo fenilo o piridina, y donde en los grupos de 5, 6 o 7 miembros indicados con anterioridad uno o dos grupos -CH2- no adyacentes pueden estar reemplazados, en forma independiente entre sí, por un grupo -CO-, -C(=CH2)-, -(SO)- o -(SO2)-, y donde los grupos saturados de 6 o 7 miembros indicados con anterioridad también pueden estar presentes como sistema de anillos en puente con un puente imino, (alquil C1-4)-imino, metileno, (alquil C1-4)-metileno o di(alquil C1-4)-metileno y donde los grupos cíclicos mencionados con anterioridad pueden estar mono o polisustituidos en uno o varios átomos de C con R20, en el caso de un grupo fenilo, también pueden estar adicionalmente monosustituidos con nitro y/o uno o varios grupos NH con R21; R4 y R5 tienen, en forma independiente entre sí, uno de los significados indicados para R17, R10 es hidroxi, omega-hidroxi-alquilo C1-3, alcoxi C1-4, omega-(alcoxi C1-4)-alquilo C1-3, carboxi, alcoxicarbonilo C1-4, amino, alquil C1-4-amino, di-(alquil C1-4)-amino, ciclo-alquilenimino C3-6, amino-alquilo C1-3, alquil C1-4-amino-alquilo C1-3, di-(alquil C1-4)-aminoalquilo C1-3, cicloalquilenimino-C3-6-alquilo C1-3, amino-alcoxi C2-3, alquil C1-4-amino-alcoxi C2-3, di-(alquil C1-4)-amino-alcoxi C2-3, cicloalquilenimino C3-6-alcoxi C2-3, aminocarbonilo, alquil C1-4-amino-carbonilo, di-(alquil C1-4)-aminocarbonilo o ciclo-alquilenimino C3-6-carbonilo; R11 es alquenilo C2-6, alquinilo C2-6, -R15-O-, -R15-O-CO-, R15-CO-O-, R16R17N-, R18R19N-CO- o Cy-; R12 tiene uno de los significados indicados para R20; R13 tiene uno de los significados indicados para R 17, excepto carboxi; R14 es halógeno, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, R15-O-, -R15-O-CO-, -R15-CO-, R15-CO-O-, -R16R17N-, R18R19N-CO, R15-O-alquilo C1-3, R15-O-CO-alquilo C1-3, R15-O-CO-NH-, R15-SO2-NH-, R15-CO-alquilo C1-3, R15-CO-O-alquilo C1-3, R1617N-alquilo C1-3, R18R19N-CO-alquilo C1-3 o Cy-alquilo C1-3; R15 es H, alquilo C1-4, cicloalquilo C3-7, cicloalquil C3-7-alquilo C1-3, fenilo, fenil-alquilo C1-3, piridinilo o piridinil-alquilo C1-3M; R16 es H, alquilo C1-6, cicloalquilo C3-7, cicloalquil C3-7-alquilo C1-3, cicloalquenilo C4-7, cicloalquenil C4-7-alquilo C1-3, omega-hidroxi-alquilo C2-3, omega-(alcoxi C1-4)-alquilo C2-3, amino-alquilo C2-6, alquil C1-4-amino-alquilo C2-6, di-(alquil C1-4)-amino-alquilo C2-6 o cicloalquilenimino C3-6-alquilo C2-6; R17 tiene uno de los significados indicados para 16 o es fenilo, fenil-alquilo C1-3, piridinilo, dioxolan-2-ilo, -CHO, alquilcarbonilo C1-4, carboxi, hidroxicarbonil-alquilo C1-3, alcoxicarbonilo C1-4, alcoxicarbonil C1-4-alquilo C1-3, alquilcarbonilamino C1-4-alquilo C2-3, N-(alquilcarbonil C1-4)-N-(alquil C1-4)-amino-alquilo C2-3, alquilsulfonilo C1-4, alquilsulfonilamino C1-4-alquilo C2-3 o N-(alquilsulfonil C1-4)-N-(alquil C1-4)-amino-alquilo C2-3; R18, R19 son, en forma independiente entre sí, H o alquilo C1-6; R20 es halógeno, hidroxi, ciano, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, cicloalquilo C3-7, cicloalquil C3-7-alquilo C1-3, hidroxi-alquilo C1-3, R22-alquilo C1-3 o uno de los significados indicados para R22; R21 es alquilo C1-4, omega-hidroxi-alquilo C2-6, omega-alcoxi C1-4-alquilo C2-6, omega-alquil C1-4-amino-alquilo C2-6, omega-di-(alquil C1-4)-amino-alquilo C2-6, omega-ciclo-alquilenimino C3-6-alquilo C2-6, fenilo, fenil-alquilo C1-3, alquil C1-4-carbonilo, alcoxi C1-4-carbonilo, alquilsulfonilo C1-4, fenilcarbonilo o fenil-C1-3-alquil-carbonilo, R22 es piridinilo, fenilo, fenil-alcoxi C1-3, -OHC, -HO-N=HC, alcoxi C1-4-N=HC-, alcoxi C1-4, alquiltio C1-4, carboxi, alquilcarbonilo C1-4, alcoxicarbonilo C1-4, aminocarbonilo, alquilaminocarbonilo C1-4, di-(alquil C1-4)-aminocarbonilo, ciclo-alquil C3-6-amino-carbonilo, ciclo-alquilenimino C3-6-carbonilo, ciclo-alquilenimino-C3-6-alquil-C2-4-aminocarbonilo, alquil C1-4-sulfonilo, alquil C1-4-sulfinilo, alquil C1-4-sulfonilamino, amino, alquilamino C1-4, di-(alquil C1-4)-amino, alquil C1-4-carbonil-amino, ciclo-alquilenimino C3-6, fenil-alquilamino C1-3, N-(alquil C1-4)-fenil-alquilamino C1-3, acetilamino, propionilamino, fenilcarbonilo, fenilcarbonilamino, fenilcarbonilmetilamino, hidroxi-alquilaminocarbonilo C2-3, (4-morfolinil)carbonilo, (1-pirrolidinil)carbonilo, (1-piperidinil)carbonilo, (hexahidro-1-azepinil)carbonilo, (4-metil-1-piperazinil)carbonilo, metilendioxi, aminocarbonilamino o alquilaminocarbonilamino, donde en los grupos y radicales mencionados con anterioridad, en especial en A, B, W, X, Y, Z, R1 a R5 y R10 a R22, uno o varios átomos de C pueden estar adicionalmente mono o polisustituidos con F y/o uno o dos átomos de C en forma independiente entre sí, pueden estar adicionalmente monosustituidos con Cl, o Br y/o uno o varios anillo fenilo, en forma independiente entre sí, pueden tener adicionalmente uno, dos o tres sustituyentes seleccionados del grupo F, Cl, Br, I, ciano, alquilo C1-4, alcoxi C1-4-, difluorometilo, trifluorometilo, hidroxi, amino, alquilamino C1-3, di-(alquil C1-3)-amino
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