AR107426A1 - DERIVADOS DE N-INDEN-AMIDA COMO MODULADORES DEL mGluR7 - Google Patents

DERIVADOS DE N-INDEN-AMIDA COMO MODULADORES DEL mGluR7

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Publication number
AR107426A1
AR107426A1 ARP170100186A ARP170100186A AR107426A1 AR 107426 A1 AR107426 A1 AR 107426A1 AR P170100186 A ARP170100186 A AR P170100186A AR P170100186 A ARP170100186 A AR P170100186A AR 107426 A1 AR107426 A1 AR 107426A1
Authority
AR
Argentina
Prior art keywords
substituted
alkyl
heterocyclic ring
halogen
cycloalkyl
Prior art date
Application number
ARP170100186A
Other languages
English (en)
Inventor
Katy White
Martin Teall
Stephen Mack
Gemma Liwicki
Anne Goldby
Original Assignee
Takeda Pharmaceuticals Co
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 Takeda Pharmaceuticals Co filed Critical Takeda Pharmaceuticals Co
Publication of AR107426A1 publication Critical patent/AR107426A1/es

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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
    • C07C233/41—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a ring other than a six-membered aromatic ring
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
    • C07C235/36—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring
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    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • C07C231/00—Preparation of carboxylic acid amides
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    • C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
    • C07C233/23—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a ring other than a six-membered aromatic ring
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    • C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C237/20—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton containing six-membered aromatic rings
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    • C07C271/24—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a ring other than a six-membered aromatic ring
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    • C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
    • C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C311/03—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C311/06—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms to acyclic carbon atoms of hydrocarbon radicals substituted by carboxyl groups
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    • C07C317/30—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of rings other than six-membered aromatic rings of the carbon skeleton
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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
    • C07D213/60—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
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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
    • C07D213/60—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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
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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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    • 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
    • C07D231/14—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 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
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    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
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    • C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
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    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
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    • C07D295/135—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
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  • Epoxy Compounds (AREA)
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Abstract

Procesos para su preparación, composiciones farmacéuticas que los contienen y su uso en la terapia de trastornos auditivos y del SNC. Reivindicación 1: Un compuesto de fórmula (1) donde R¹ representa hidroxilo, -CH₂OH, ciano, -SO₂R¹ᵃ, -(CH₂)ₘ-(O)ₙ-R⁵ o (CH₂)ₚNR⁶R⁷; m es 0 ó 1; n es 0 ó 1; p es 0 ó 1; R¹ᵃ representa alquilo C₁₋₆, cicloalquilo C₃₋₆ o cicloalquilmetilo C₃₋₆; cada uno de R² y R³ representa independientemente hidrógeno, halógeno, fluorometilo, difluorometilo, trifluorometilo, metoxi, fluorometoxi, difluorometoxi o trifluorometoxi; cualquier R⁴ᵃ representa (X)ₜ-(CH₂)ᵛ-R¹⁶ o -CH₂O-R¹⁷ y R⁴ᵇ representa hidrógeno, metilo o flúor, o R⁴ᵃ y R⁴ᵇ, junto con el átomo de carbono al cual se acoplan, forman un anillo heterocíclico o carbocíclico saturado de 3 a 6 miembros, donde el anillo heterocíclico comprende al menos un heteroátomo anular que se selecciona de átomos de nitrógeno y oxígeno, donde el anillo carbocíclico o heterocíclico no está sustituido o está sustituido con al menos un sustituyente que se selecciona de halógeno, oxo, alquilo C₁₋₃, alcoxi C₁₋₃, amino, metilamino, dimetilamino y haloalquilo C₁₋₃; R⁵ representa un grupo cicloalquilo C₃₋₆, un anillo heterocíclico de 4 a 6 miembros que contiene un heteroátomo anular individual que es un átomo de nitrógeno donde el anillo heterocíclico no está sustituido o está sustituido con al menos un sustituyente seleccionado de halógeno, alquilo C₁₋₃ y haloalquilo C₁₋₃ o un grupo alquilo C₁₋₆ que no está sustituido o está sustituido con al menos un sustituyente seleccionado de cicloalquilo C₃₋₆, NR²²R²³ y un anillo heterocíclico saturado de 4 a 6 miembros que comprende al menos un heteroátomo anular que se selecciona de átomos de nitrógeno y oxígeno, donde dicho anillo heterocíclico no está sustituido o está sustituido con halógeno; cada uno de R⁶ y R⁷ representa independientemente hidrógeno, -(CH₂)q-R⁸, -SO₂R⁹, alquilo C₁₋₆, alquilcarbonilo C₁₋₆, cicloalquilcarbonilo C₃₋₆ o alcoxicarbonilo C₁₋₆, donde cada uno de los restos alquilo, cicloalquilo o alcoxi en los últimos cuatro sustituyentes no está sustituido o está sustituido con al menos un sustituyente que se selecciona de halógeno, alcoxi C₁₋₄ y -NR¹⁰R¹¹, o R⁶ y R⁷, junto con el átomo de nitrógeno al cual se acoplan, forman un anillo heterocíclico saturado o no saturado de 4 a 7 miembros que comprende opcionalmente un heteroátomo anular adicional que se selecciona de nitrógeno, oxígeno y azufre, donde el anillo heterocíclico no está sustituido o está sustituido con al menos un sustituyente que se selecciona de halógeno, ciano, alquilo C₁₋₆, cicloalquilo C₃₋₆, cicloalquilmetilo C₃₋₆, haloalquilo C₁₋₆, alcoxi C₁₋₆, cicloalquiloxi C₃₋₆, cicloalquilmetiloxi C₃₋₆ y -NR¹²R¹³; q es 0, 1 ó 2; R⁸ representa un anillo carbocíclico o heterocíclico saturado o no saturado de 3 a 6 miembros donde el anillo heterocíclico comprende de 1 a 4 heteroátomos anulares que se seleccionan independientemente de nitrógeno, oxígeno y azufre, donde el anillo carbocíclico o heterocíclico no está sustituido o está sustituido con al menos un sustituyente que se selecciona de halógeno, ciano, alquilo C₁₋₆, cicloalquilo C₃₋₆, cicloalquilmetilo C₃₋₆, haloalquilo C₁₋₆, alcoxi C₁₋₆, cicloalquiloxi C₃₋₆, cicloalquilmetiloxi C₃₋₆ y -NR¹⁴R¹⁵; R⁹ representa alquilo C₁₋₆, cicloalquilo C₃₋₆ o cicloalquilmetilo C₃₋₆, cada uno de los cuales no está sustituido o está sustituido con al menos un átomo de halógeno; cada uno de R¹⁰ y R¹¹ representa independientemente hidrógeno, alquilo C₁₋₆, cicloalquilo C₃₋₆ o cicloalquilmetilo C₃₋₆, o R¹⁰ y R¹¹, junto con el átomo de nitrógeno al cual se acoplan, forman un anillo heterocíclico saturado de 4 a 6 miembros que comprende opcionalmente un heteroátomo anular adicional que se selecciona de átomos de nitrógeno y oxígeno, donde el anillo heterocíclico no está sustituido o está sustituido con al menos un sustituyente que se selecciona de halógeno y alquilo C₁₋₃; cada uno de R¹² y R¹³ representa independientemente hidrógeno, alquilo C₁₋₆, cicloalquilo C₃₋₆ o cicloalquilmetilo C₃₋₆, o R¹² y R¹³, junto con el átomo de nitrógeno al cual se acoplan, forman un anillo heterocíclico saturado de 4 a 6 miembros que comprende opcionalmente un heteroátomo anular adicional que se selecciona de átomos de nitrógeno y oxígeno, donde el anillo heterocíclico no está sustituido o está sustituido con al menos un sustituyente que se selecciona de halógeno y alquilo C₁₋₃; cada uno de R¹⁴ y R¹⁵ representa independientemente hidrógeno, alquilo C₁₋₆, cicloalquilo C₃₋₆ o cicloalquilmetilo C₃₋₆, o R¹⁴ y R¹⁵, junto con el átomo de nitrógeno al cual se acoplan, forman un anillo heterocíclico saturado de 4 a 6 miembros que comprende opcionalmente un heteroátomo anular adicional que se selecciona de átomos de nitrógeno y oxígeno, donde el anillo heterocíclico no está sustituido o está sustituido con al menos un sustituyente que se selecciona de halógeno y alquilo C₁₋₃; t es 0 ó 1; v es 0, 1 ó 2; R¹⁶ representa -R¹⁷, -NR¹⁸R¹⁹ o un anillo heterocíclico saturado o no saturado de 4 a 6 miembros que comprende de 1 a 4 heteroátomos anulares que se seleccionan independientemente de nitrógeno, oxígeno y azufre, donde el anillo heterocíclico no está sustituido o está sustituido con al menos un sustituyente seleccionado de oxo, halógeno, ciano, fluorometoxi, difluorometoxi, trifluorometoxi, alquilo C₁₋₆, alcoxi C₁₋₆ y haloalquilo C₁₋₆; X es O, NH, -NHC(O)-, -NHC(O)O-, -C(O)NH-, -NHSO₂- o -SO₂NH-, siempre que cuando X sea O, NH, -C(O)NH- o -SO₂NH- y R¹⁶ represente -NR¹⁸R¹⁹, v sea 2; R¹⁷ representa alquilo C₁₋₆, cicloalquilo C₃₋₆ o cicloalquilmetilo C₃₋₆, cada uno de los cuales no está sustituido o está sustituido con al menos un sustituyente que se selecciona de hidroxilo, halógeno y -NR²⁰R²¹; cada uno de R¹⁸ y R¹⁹ representa independientemente hidrógeno, alquilo C₁₋₆, alquilcarbonilo C₁₋₆, cicloalquilcarbonilo C₃₋₆, alquilsulfonilo C₁₋₆ o cicloalquilsulfonilo C₃₋₆, donde cada uno de los restos alquilo o cicloalquilo en los últimos cinco sustituyentes no está sustituido o está sustituido con al menos un sustituyente que se selecciona de halógeno y alcoxi C₁₋₄, o R¹⁸ y R¹⁹, junto con el átomo de nitrógeno al cual se acoplan, forman un anillo heterocíclico saturado de 4 a 6 miembros que comprende opcionalmente un heteroátomo anular adicional que se selecciona de átomos de nitrógeno y oxígeno, donde el anillo heterocíclico no está sustituido o está sustituido con al menos un sustituyente que se selecciona de halógeno y alquilo C₁₋₃; cada uno de R²⁰ y R²¹ representa independientemente hidrógeno, alquilo C₁₋₆, cicloalquilo C₃₋₆ o cicloalquilmetilo C₃₋₆, o R²⁰ y R²¹, junto con el átomo de nitrógeno al cual se acoplan, forman un anillo heterocíclico saturado de 4 a 6 miembros que comprende opcionalmente un heteroátomo anular adicional que se selecciona de átomos de nitrógeno y oxígeno, donde el anillo heterocíclico no está sustituido o está sustituido con al menos un sustituyente que se selecciona de halógeno y alquilo C₁₋₃; y cada uno de R²² y R²³ representa independientemente hidrógeno, alquilo C₁₋₆, cicloalquilo C₃₋₆ o cicloalquilmetilo C₃₋₆, o R²² y R²³, junto con el átomo de nitrógeno al cual se acoplan, forman un anillo heterocíclico saturado de 4 a 6 miembros que comprende opcionalmente un heteroátomo anular adicional que se selecciona de átomos de nitrógeno y oxígeno, donde el anillo heterocíclico no está sustituido o está sustituido con al menos un sustituyente que se selecciona de halógeno y alquilo C₁₋₃; siempre que el compuesto de fórmula (1) no sea N-[(1S,2S)-1-amino-2,3-dihidro-1H-inden-2-il]-1-(4-fluorofenil)ciclopropano-1-carboxamida; o una sal farmacéuticamente aceptable de este.
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