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AR045697A1 - Aril y heteroaril derivados fusionados como moduladores del metabolismo y la prevencion y tratamiento de trastornos relacionados con el mismo - Google Patents

Aril y heteroaril derivados fusionados como moduladores del metabolismo y la prevencion y tratamiento de trastornos relacionados con el mismo

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Publication number
AR045697A1
AR045697A1 ARP040102465A ARP040102465A AR045697A1 AR 045697 A1 AR045697 A1 AR 045697A1 AR P040102465 A ARP040102465 A AR P040102465A AR P040102465 A ARP040102465 A AR P040102465A AR 045697 A1 AR045697 A1 AR 045697A1
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AR
Argentina
Prior art keywords
alkyl
alkoxy
group
cycloalkyl
haloalkyl
Prior art date
Application number
ARP040102465A
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English (en)
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Arena Pharm Inc
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Publication of AR045697A1 publication Critical patent/AR045697A1/es

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C07D215/22—Oxygen atoms attached in position 2 or 4
    • C07D215/233—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 4
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/04—Anorexiants; Antiobesity agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/06—Antihyperlipidemics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00—Drugs for disorders of the endocrine system
    • A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
    • A61P5/50—Drugs for disorders of the endocrine system of the pancreatic hormones for increasing or potentiating the activity of insulin
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D473/00—Heterocyclic compounds containing purine ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/04—Ortho-condensed systems

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Diabetes (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Engineering & Computer Science (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Endocrinology (AREA)
  • Emergency Medicine (AREA)
  • Child & Adolescent Psychology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
  • Pyridine Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Hydrogenated Pyridines (AREA)

Abstract

Los compuestos de la presente son útiles para la prevención o el tratamiento de trastornos metabólicos y sus complicaciones, tales como diabetes y obesidad. Reivindicación 1: Un compuesto de fórmula (1), o una sal, hidrato o solvato del mismo aceptable desde el punto de vista farmacéutico; donde, A y B son cada uno independientemente alquileno C1-3 opcionalmente substituido con 1 a 4 substituyentes seleccionados del grupo formado por alquilo C1-3, alcoxi C1-4, carboxi, ciano, haloalquilo C1-3 y halógeno; D es O, S, S (O),S(O)2, CR1R2 o N-R2, donde R, se selecciona del grupo formado por H, alquilo C1-8, alcoxi C1-4, halógeno y hidroxilo; E es N, C o CR3, donde R3 es H o alquilo C1-8; la línea punteada es un enlace simple cuando E es N o CR3, o un doble enlace cuando E es C; K es un cicloalquileno C3-6 o alquileno C1-3 donde cada uno está opcionalmente substituido con 1 a 4 substituyentes seleccionados del grupo formado por alquilo C1-3, alcoxi C1-4, carboxi, ciano, haloalquilo C1-3 y halógeno; o K es un enlace; Q es NR4, O, S, S(O) o S(O)2, donde R4 es H o alquilo C1-8 y el alquilo C1-8 está opcionalmente substituido con dialquilamina C2-8; T es N o CR5; M es N o CR6; J es N o CR7; U es C o N; V es N, CR8 o V es un enlace; W es N o C; X es O, S, N, CR9 o NR11;Y es O, S, N, CR10 o NR12; Z es C o N; R5, R6, R7, R8, R9 y R10 se seleccionan cada uno independientemente del grupo formado por H, aciloxi C1-5, alquenilo C2-6, alcoxi C1-4, alquilo C1-8, alquilcarboxamida C1-4, alquinilo C2-6, alquilsulfonamida C1-4, alquilsulfinilo C1-4, alquilsulfonilo C1-4, alquiltio C1-4, alquilureilo C1-4, amino, alquilamino C1-4, dialquilamino C2-8, carboxamida, ciano, cicloalquilo C3-6, dialquilcarboxamida C2- 6, dialquilsulfonamida C2-6, halógeno, haloalquioxi C1-4, haloalquilo C1-4, haloalquilsulfinilo C1-4, haloalquilsulfonilo C1-4, haloalquiltio C1-4, hidroxilo, hidroxilamino y nitro; donde dicho alquenilo C2-6, alquilo C1-8, alquinilo C2-6 y cicloalquilo C3-6 están opcionalmente substituido con 1, 2, 3 o 4 substituyentes seleccionados del grupo formado por acilo C1-5, aciloxi C1-5, alcoxi C1-4, alquilamino C1-4, alquilcarboxamida C1-4, alquiltiocarboxamida C1-4, alquilsulfonamida C1-4, alquilsulfinilo C1-4, alquilsulfonilo C1-4, alquiltio C1-4, alquiltioureilo C1-4, alquilureilo C1-4, amino, carbo-alcoxi C1-6, carboxamida, carboxi, ciano, dialquilamino C2-8, dialquilcarboxamida C2-6, dialquiltiocarboxamida C1-4, dialquilsulfonamida C2-6, alquiltioureilo C1-4, haloalcoxi C1-4, haloalquilo C1-4, haloalquilsulfinilo, haloalquilsulfonilo C1-4, haloalquilo C1-4, haloalquiltio C1-4, halógeno, hidroxilo, hidroxilamino y nitro; R11 y R12 se seleccionan cada uno independientemente del grupo formado por alquenilo C2-6, alquilo C1-8, alquinilo C2-6 o cicloalquilo C3-6 cada uno opcionalmente substituido con 1, 2, 3 o 4 substituyentes seleccionados entre acilo C1-5, aciloxi C1-5, alcoxi C1-4, alquilamino C1-4, alquilcarboxamida C1-4, alquiltiocarboxamida C1-4, alquilsulfonamida C1-4, alquilsulfinilo C1-4, alquilsulfonilo C1-4, alquiltio C1-4, alquiltioureilo C1-4, alquilureilo C1-4, amino, carbo-alcoxi C1-6, carboxamida, carboxi, ciano, dialquilamino C2- 8, dialquilcarboxamida C2-6, dialquiltiocarboxamida C1-4, dialquilsulfonamida C2-6, alquiltioureilo C1-4, haloalcoxi C1-4, haloalquilo C1-4, haloalquilsulfinilo C1-4, haloalquilsulfonilo C1-4, haloalquilo C1-4, haloalquiltio C1-4, halógeno, hidroxilo, hidroxilamino y nitro; Ar1 es arilo o heteroarilo cada uno opcionalmente substituido con R13, R14, R15, R16, y R17; donde R13 se selecciona del grupo formado por acilo C1-5, acilsulfonamida C1-6, aciloxi C1-5, alquenilo C2-6, alcoxi C1-4, alquilo C1-8, alquilamino C1-4, alquilcarboxamida C1-6, alquiltiocarboxamida C1-4, alquinilo C2-6, alquilsulfonamida C1-4, alquilsulfinilo C1-4, alquilsulfonilo C1-4, alquiltio C1-4, alquiltioureilo C1-4, alquilureilo C1-4, amino, arilsulfonilo, carbamimidoilo, carbo-alcoxi C1-6, carboxamida, carboxi, ciano, cicloalquilo C3-7, cicloalquiloxi C3-7, dialquilamino C2-6, dialquilcarboxamida C2-6, dialquiltiocarboxamida C2-6, guanidinilo, halógeno, haloalcoxi C1-4, haloalquilo C1-4, haloalquilsulfinilo C1-4, haloalquilsulfonilo C1-4, haloalquiltio C1-4, heterocíclico, oxiheterocíclico, sulfoniloheterocíclico, carbonilo heterocíclico, heteroarilo, heteroarilcarbonilo, hidroxilo, nitro, oxo-cicloalquilo C4-7, fenoxi, fenilo, sulfonamida, ácido sulfónico, y tiol, y donde acilo C1-5, acilsulfonamida C1-6, alcoxi C1-4, alquilo C1-8, alquilamino C1-4, alquilsulfonamida C1-4, alquilsulfonilo C1-4, alquiltio C1-4, arilsulfonilo, carbamimidoilo, dialquilamino C2-6, heterocíclico, carbonilo heterocíclico, heteroarilo, fenoxi y fenilo están opcionalmente substituido con 1 a 5 substituyentes seleccionados independientemente del grupo formado por acilo C1-5, aciloxi C1-5, alquenilo C2-6, alcoxi C1-4, alquilo C1-7, alquilamino C1-4, alquilcarboxamida C1-4, alquinilo C2-6, alquilsulfonamida C1-4, alquilsulfinilo C1-4, alquilsulfonilo C1-4, alquiltio C1-4, alquilureílo C1-4, carbo-alcoxi C1-4, carboxamida, carboxi, ciano, cicloalquilo C3-7, cicloalquiloxi C3-7, dialquilamino C2-6, dialquilcaboxamida C2-6, halógeno, haloalcoxi C1-4, haloalquilo C1-4, halalquilsulfinilo C1-4, haloalquilsulfonilo C1-4, haloalquiltio C1-4, heteroarilo, heterocíclico, hidroxilo, nitro, fenilo y fosfonoxi, donde dichos alquilo C1-7 y alquilcarboxamida C1-4 están cada uno opcionalmente substituido con 1 a 5 substituyentes seleccionados del grupo formado por alcoxi C1-4 e hidroxi; o R13 es un grupo de fórmula (2), donde "p" y "r" son independientemente 0, 1, 2 ó 3; y R18 es H, acilo C1-5, alquenilo C2-6, alquilo C1-8, alquilcarboxamida C1-4, alquinilo C2-6, alquilsulfonamida C1-4, carbo-alcoxi C1-6, carboxamida, carboxi, ciano, cicloalquilo C3-7, dialquilcarboxamida C2-6, halógeno, heteroarilo o fenilo, y donde dichos heteroarilo o fenilo están opcionalmente substituidos con 1 a 5 substituyentes seleccionados independientemente del grupo formado por alcoxi C1-4, amino, alquilamino C1-4, alquinilo C2-6, dialquilamino C2-8, halógeno, haloalcoxi C1-4, haloalquilo C1- 4 e hidroxilo; R14, R15, R16, y R17 se seleccionan cada uno independientemente del grupo formado por H, acilo C1-5, aciloxi C1-5, alquenilo C2-6, alcoxi C1-4, alquilo C1-8, alquilcarboxamida C1-4, C2-6alquinilo C2-6, alquilsulfonamida C1-4, alquilsulfinilo C1-4, alquilsulfonilo C1-4, alquiltio C1-4, alquilureilo C1-4, carbo-alcoxi C1-6, carboxamida, carboxi, ciano, cicloalquilo C3-7, dialquilcarboxamida C2-6, halógeno, haloalcoxi C1-4, haloalquilo C1-4, haloalquilsulfinilo C1-4, haloalquilsulfonilo C1-4, haloalquiltio C1-4, hidroxilo y nitro; o dos grupos adyacentes seleccionados del grupo formado por R14, R15, R16 y R17 forman un grupo cicloalquilo, cicloalquenilo o heterocíclico de 5, 6 o 7 miembros con Ar1 donde el grupo de 5, 6 o 7 miembros está opcionalmente substituido con halógeno; y R2 se selecciona del grupo formado por alquilo C1-8, alquinilo C2-6, amino, arilo, carboxamida, carboxi, ciano, cicloalquilo C3-6, haloalcoxi C1-4, haloalquilo C1-4, halógeno, heteroarilo e hidroxilo; y donde alquilo C1-8, arilo y heteroarilo están opcionalmente substituidos con 1 a 5 substituyentes seleccionados del grupo formado por acilo C1-5, aciloxi C1-5, alcoxi C1-4, alquilo C1-8, alquilamino C1-4, alquilcarboxamida C1-4, alquiltiocarboxamida C1-4, alquilsulfonamida C1-4, alquilsulfinilo C1-4, alquilsulfonilo C1-4, alquiltio C1-4, alquiltioureilo C1-4, alquilureilo C1-4, amino, carbo-alcoxi C1-6, carboxamida, carboxi, ciano, cicloalquilo C3-6, cicloalquil C3-6- heteroalquileno C1-3, dialquilamino C2-8, dialquilcarboxamida C2-6, dialquiltiocarboxamida C2-6, dialquilsulfonamida C2-6, alquiltioureilo C1-4, haloalcoxi C1-4, haloalquilo C1-4, haloalquilsulfinilo C1-4, haloalquilsulfonilo C1-4, haloalquilo C1-4, haloalquiltio C1-4, halógeno, heterocíclico, hidroxilo, hidroxilamino y nitro; o R2 es -Ar2-Ar3 donde Ar2 y Ar3 son cada uno independientemente arilo o heteroarilo opcionalmente substituido con 1 a 5 substituyentes seleccionados del grupo formado por H, acilo C1-5, aciloxi C1-5, alcoxi C1-4, alquilo C1-8, alquilcarboxamida C1-4, alquiltiocarboxamida C1-4, alquilsulfinilo C1-4, alquilsulfonilo C1-4, alquiltio C1-4, amino, alquilamino C1-4, carbo-alcoxi C1-6, carboxamida, carboxi, ciano, cicloalquilo C3-6, dialquilamino C2-8, dialquilcarboxamida C2-6, haloalcoxi C1-4, haloalquilo C1-4, halógeno, hidroxilo y nitro; o R2 es un grupo de fórmula (3), donde R19 es H, alquilo C1-8, cicloalquilo C3-7, arilo, heteroarilo u OR21; y R20 es F, Cl, Br, CN o NR22R23; donde R21 es H, alquilo C1-8 o cicloalquilo C3-7, y R22 y R23 son independientemente H, alquilo C1-8, cicloalquilo C3-7, arilo o heteroarilo; o R2 es un grupo de fórmula (4), donde G es: i) -C(O)-, -C(O)NR25-, -NR25C(O)-, -NR25- , -NR25C(O)O-, -OC(O)NR25-, -CR25R26NR27C(O)-, -CR25R26C(O)NR27-, -C(O)O-, -OC(O)-, -C(S)-, -C(S)NR25-, -C(S)O-, -OC(S)-, -CR25R26-, -O-, -S-, -S(O)-, -S(O)2- o un enlace donde D es CR2R3; o ii) -CR25R26C(O)-, -C(O)-, -CR25R26C(O)NR27-, -C(O)NR25-, - C(O)O-, -C(S)-, -C(S)NR25-, -C(S)O-, -CR25R26-, -S(O)2-, o un enlace donde D es NR2; donde R25, R26 y R27 son cada uno independientemente H o alquilo C1-8; y R24 es H, alquilo C1-8, cicloalquilo C3-7, fenilo, heteroarilo, o heterocíclico cada uno opcionalmente substituido con 1 a 5 substituyentes seleccionados del grupo formado por acilo C1-5, aciloxi C1-5, alquenilo C2-6, alcoxi C1-4, alquilo C1-7, alquilamino C1-4, alquilcarboxamida C1-4, alquiltiocarboxamida C1-4, alquilsulfonamida C1-4, alquilsulfinilo C1-4, alquilsulfonilo C1-4, alquiltio C1-4, alquiltioureilo C1-4, alquilureilo C1-4, amino, carbo-alcoxi C1-6, carboxamida, carboxi, ciano, cicloalquilo C3-7, dialquilamino C2-8, dialquilcarboxamida C2-6, dialquiltiocarboxamida C2-6, dialquilsulfonamida C2-6, alquiltioureilo C1-4, haloalcoxi C1-4, haloalquilo C1-4, haloalquilsulfinilo C1-4, haloalquilsulfonilo C1-4, haloalquil
ARP040102465A 2003-07-14 2004-07-13 Aril y heteroaril derivados fusionados como moduladores del metabolismo y la prevencion y tratamiento de trastornos relacionados con el mismo AR045697A1 (es)

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ARP060101765A AR053863A2 (es) 2003-07-14 2006-05-02 Aril y heteroaril derivados fusionados como moduladores del metabolismo y la prevencion y tratamiento de trastornos ralacionados con el mismo

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