AR112139A1 - DERIVATIVE OF NITROCATECOL - Google Patents

DERIVATIVE OF NITROCATECOL

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Publication number
AR112139A1
AR112139A1 ARP180101599A ARP180101599A AR112139A1 AR 112139 A1 AR112139 A1 AR 112139A1 AR P180101599 A ARP180101599 A AR P180101599A AR P180101599 A ARP180101599 A AR P180101599A AR 112139 A1 AR112139 A1 AR 112139A1
Authority
AR
Argentina
Prior art keywords
group
optionally substituted
ring
atom
alkyl
Prior art date
Application number
ARP180101599A
Other languages
Spanish (es)
Original Assignee
Fujiyakuhin Co Ltd
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 Fujiyakuhin Co Ltd filed Critical Fujiyakuhin Co Ltd
Publication of AR112139A1 publication Critical patent/AR112139A1/en

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/415—1,2-Diazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/4164—1,3-Diazoles
    • A61K31/417—Imidazole-alkylamines, e.g. histamine, phentolamine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/4192—1,2,3-Triazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/4196—1,2,4-Triazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/42—Oxazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/42—Oxazoles
    • A61K31/421—1,3-Oxazoles, e.g. pemoline, trimethadione
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    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/4245—Oxadiazoles
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    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/425—Thiazoles
    • A61K31/426—1,3-Thiazoles
    • A—HUMAN NECESSITIES
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    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
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    • 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
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
    • A—HUMAN NECESSITIES
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    • 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
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
    • A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
    • A—HUMAN NECESSITIES
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    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/50—Pyridazines; Hydrogenated pyridazines
    • A61K31/501—Pyridazines; Hydrogenated pyridazines not condensed and containing further heterocyclic rings
    • 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
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
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    • A—HUMAN NECESSITIES
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
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    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
    • C07D249/06—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles with aryl radicals directly attached to ring atoms
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    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
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    • C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
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    • C—CHEMISTRY; METALLURGY
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/04—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
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    • C07D—HETEROCYCLIC COMPOUNDS
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    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole 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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    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
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    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
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    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole 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
    • C07D277/28—Radicals substituted by nitrogen atoms
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    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole 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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    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
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    • C07D413/08—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 carbon chain containing alicyclic rings

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Neurosurgery (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Psychology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Un derivado de nitrocatecol o una de sus sales que muestra una actividad inhibidora de COMT y una actividad inhibidora de DDC y una composición farmacéutica que lo comprende. Reivindicación 1: Un compuesto caracterizado por la fórmula (1) o una de sus sales farmacéuticamente aceptables, en donde R¹ y R² representa cada uno, de modo independiente, un átomo de hidrógeno, un grupo alquilo C₁₋₆ opcionalmente sustituido, un grupo alquil C₁₋₆-carbonilo opcionalmente sustituido, un grupo alcoxi C₁₋₆-carbonilo opcionalmente sustituido o un grupo alquil C₁₋₆-aminocarbonilo opcionalmente sustituido; R³ representa un átomo de hidrógeno, un átomo de halógeno, un grupo haloalquilo, un grupo ciano o un grupo carboxi; R⁴ representa un átomo de hidrógeno, un átomo de halógeno, un grupo alquilo C₁₋₆ opcionalmente sustituido, un grupo haloalquilo, un grupo ciano, un grupo carboxi, un grupo aminocarbonilo, un grupo alquil C₁₋₆-sulfanilo opcionalmente sustituido, un grupo haloalquilsulfanilo, un grupo arilsulfanilo opcionalmente sustituido, un grupo un grupo alcoxi C₁₋₆ opcionalmente sustituido, un grupo ariloxi opcionalmente sustituido, un grupo heteroariloxi opcionalmente sustituido, un grupo alcoxi C₁₋₆-carbonilo opcionalmente sustituido, un grupo alquil C₁₋₆-carbonilo opcionalmente sustituido, un grupo arilcarbonilo opcionalmente sustituido, un grupo heteroarilcarbonilo opcionalmente sustituido, un grupo alquil C₁₋₆-sulfonilo opcionalmente sustituido, un grupo alquil C₁₋₆-sulfinilo opcionalmente sustituido, un grupo arilsulfonilo opcionalmente sustituido, un grupo heteroarilsulfonilo opcionalmente sustituido, un grupo arilsulfinilo opcionalmente sustituido, un grupo heteroarilsulfinilo opcionalmente sustituido, un grupo alquil C₁₋₆-aminocarbonilo opcionalmente sustituido, un grupo aminosulfonilo opcionalmente sustituido, un grupo heterocicloalquilcarbonilo opcionalmente sustituido, benzofurano opcionalmente sustituido, 2,3-dihidrofurano opcionalmente sustituido, un anillo cromano, un anillo 2-cromanona opcionalmente sustituido, un anillo 3-cromanona opcionalmente sustituido, un anillo 4-cromanona opcionalmente sustituido, un anillo cumarina opcionalmente sustituido, un anillo cromona opcionalmente sustituido, un anillo 2-cumaranona opcionalmente sustituido, un anillo indeno opcionalmente sustituido, un anillo indenona opcionalmente sustituido o un anillo ftalida opcionalmente sustituido; R⁵ - R¹⁰ representa cada uno, de modo independiente, un átomo de hidrógeno, un átomo de halógeno, un grupo alquilo C₁₋₆ o un grupo ciano o sus restos adyacentes forman opcionalmente un grupo carbonilo o un grupo cicloalquilo; R¹¹ representa un átomo de hidrógeno, un grupo alquil C₁₋₆-carbonilo opcionalmente sustituido, un grupo alcoxi C₁₋₆-carbonilo opcionalmente sustituido o un grupo alquil C₁₋₆-aminocarbonilo opcionalmente sustituido; X, Y y Z representan cada uno un enlace simple, un átomo de carbono, un átomo de oxígeno, un átomo de nitrógeno o un átomo de azufre; ⁻ ⁻ ⁻ ⁻ ⁻ representa un enlace simple o un enlace doble; Q¹ - Q⁶ representa cada uno, de modo independiente, un átomo de carbono (cada átomo de carbono tiene opcionalmente cualquier sustituyente de un átomo de hidrógeno, un grupo alquilo C₁₋₆ opcionalmente sustituido, un grupo alquil C₁₋₆-tio opcionalmente sustituido, un grupo alcoxi C₁₋₆ opcionalmente sustituido, un átomo de halógeno, un grupo nitro, un grupo trifluorometilo, un grupo ciano y un grupo carboxi u opcionalmente forma un anillo por medio de un átomo de carbono o un heteroátomo) o un átomo de nitrógeno o sus restos adyacentes forman opcionalmente un anillo o Q² y Q³ representan juntos un átomo de azufre o un átomo de oxígeno; n representa un número entero de 0 a 3 (siempre que n represente un número entero de 1 a 3 cuando uno de Q² - Q⁶ es un átomo de nitrógeno y los otros átomos son átomos de carbono); y anillo A representa un anillo heterocíclico de 3 a 6 miembros opcionalmente sustituido.A derivative of nitrocatechol or one of its salts which exhibits a COMT inhibitory activity and a DDC inhibitory activity and a pharmaceutical composition comprising it. Claim 1: A compound characterized by formula (1) or a pharmaceutically acceptable salt thereof, wherein R¹ and R² each independently represent a hydrogen atom, an optionally substituted C₁₋₆ alkyl group, an alkyl group Optionally substituted C₁₋₆-carbonyl, optionally substituted C₁₋₆-alkoxycarbonyl group, or optionally substituted C₁₋₆-alkylcarbonyl group; R³ represents a hydrogen atom, a halogen atom, a haloalkyl group, a cyano group or a carboxy group; R⁴ represents a hydrogen atom, a halogen atom, an optionally substituted C₁₋₆ alkyl group, a haloalkyl group, a cyano group, a carboxy group, an aminocarbonyl group, an optionally substituted C₁₋₆-alkyl sulfanyl group, a haloalkylsulfanyl, an optionally substituted arylsulfanyl group, an optionally substituted C₁₋₆ alkoxy group, an optionally substituted aryloxy group, an optionally substituted heteroaryloxy group, an optionally substituted C₁₋₆-alkoxy-carbonyl group, a C₁₋₆-alkylcarbonyl group optionally substituted, an optionally substituted arylcarbonyl group, an optionally substituted heteroarylcarbonyl group, an optionally substituted C₁₋₆-alkyl sulfonyl group, an optionally substituted C₁₋₆-alkyl-sulfinyl group, an optionally substituted arylsulfonyl group, an optionally substituted heteroarylsulfonyl group, a optionally substituted arylsulfinyl group, an optionally heteroarylsulfinyl group substituted, an optionally substituted C-alkylcarbonyl group, an optionally substituted aminosulfonyl group, an optionally substituted heterocycloalkylcarbonyl group, optionally substituted benzofuran, optionally substituted 2,3-dihydrofuran, a chroman ring, an optionally substituted 2-chromanone ring, a optionally substituted 3-chromanone ring, optionally substituted 4-chromanone ring, optionally substituted coumarin ring, optionally substituted chromone ring, optionally substituted 2-coumaranone ring, optionally substituted indene ring, optionally substituted indenone ring or phthalide ring optionally substituted; R⁵ - R¹⁰ each independently represents a hydrogen atom, a halogen atom, a C₁₋₆ alkyl group or a cyano group or their adjacent moieties optionally form a carbonyl group or a cycloalkyl group; R¹¹ represents a hydrogen atom, an optionally substituted C₁₋₆-alkylcarbonyl group, an optionally substituted C₁₋₆-alkoxy-carbonyl group or an optionally substituted C₁₋₆-alkyl-aminocarbonyl group; X, Y and Z each represent a single bond, a carbon atom, an oxygen atom, a nitrogen atom, or a sulfur atom; ⁻ ⁻ ⁻ ⁻ ⁻ Represents a single bond or a double bond; Q¹ - Q⁶ each independently represents a carbon atom (each carbon atom optionally has any substituent of a hydrogen atom, an optionally substituted C₁₋₆ alkyl group, an optionally substituted C₁₋₆ alkyl-thio group, an optionally substituted C₁₋₆ alkoxy group, a halogen atom, a nitro group, a trifluoromethyl group, a cyano group and a carboxy group or optionally forms a ring by means of a carbon atom or a heteroatom) or a nitrogen atom or their adjacent moieties optionally form a ring or Q² and Q³ together represent a sulfur atom or an oxygen atom; n represents an integer from 0 to 3 (provided that n represents an integer from 1 to 3 when one of Q² - Q⁶ is a nitrogen atom and the other atoms are carbon atoms); and Ring A represents an optionally substituted 3- to 6-membered heterocyclic ring.

ARP180101599A 2017-06-13 2018-06-12 DERIVATIVE OF NITROCATECOL AR112139A1 (en)

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