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AR048528A1 - Compuestos derivados de quinolina como antagonistas del receptor de pgd2 para el tratamiento de enfermedades inflamatorias y composiciones farmacéuticas que los contienen. - Google Patents

Compuestos derivados de quinolina como antagonistas del receptor de pgd2 para el tratamiento de enfermedades inflamatorias y composiciones farmacéuticas que los contienen.

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Publication number
AR048528A1
AR048528A1 ARP050101369A ARP050101369A AR048528A1 AR 048528 A1 AR048528 A1 AR 048528A1 AR P050101369 A ARP050101369 A AR P050101369A AR P050101369 A ARP050101369 A AR P050101369A AR 048528 A1 AR048528 A1 AR 048528A1
Authority
AR
Argentina
Prior art keywords
aromatic
group
ring
alkyl
optionally substituted
Prior art date
Application number
ARP050101369A
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English (en)
Inventor
Shomir Ghosh
Amy M Elder
Kenneth G Carson
Kevin T Sprott
Sean Harrison
Frederick Hicks
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Millennium Pharm Inc
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Filing date
Publication date
Application filed by Millennium Pharm Inc filed Critical Millennium Pharm Inc
Publication of AR048528A1 publication Critical patent/AR048528A1/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
    • C07D215/38—Nitrogen atoms
    • C07D215/42—Nitrogen atoms attached in position 4
    • C07D215/44—Nitrogen atoms attached in position 4 with aryl radicals attached to said nitrogen atoms
    • 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
    • A61K31/435—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
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/18—Drugs for disorders of the alimentary tract or the digestive system for pancreatic disorders, e.g. pancreatic enzymes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/06—Antiasthmatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/08—Bronchodilators
    • 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
    • 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
    • A61P17/04—Antipruritics
    • 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
    • A61P17/10—Anti-acne agents
    • 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
    • A61P21/00—Drugs for disorders of the muscular or neuromuscular system
    • A61P21/04—Drugs for disorders of the muscular or neuromuscular system for myasthenia gravis
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/16—Otologicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • 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
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/08—Antiallergic agents
    • 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
    • A61P5/14—Drugs for disorders of the endocrine system of the thyroid hormones, e.g. T3, T4
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • 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
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C07D215/50—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Immunology (AREA)
  • Pulmonology (AREA)
  • Diabetes (AREA)
  • Dermatology (AREA)
  • Neurology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Endocrinology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Rheumatology (AREA)
  • Emergency Medicine (AREA)
  • Hematology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Biomedical Technology (AREA)
  • Vascular Medicine (AREA)
  • Neurosurgery (AREA)
  • Pain & Pain Management (AREA)
  • Urology & Nephrology (AREA)
  • Obesity (AREA)
  • Cardiology (AREA)
  • Transplantation (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

Se describe el uso de dichos compuestos para inhibir el receptor acoplado a proteína G mencionados como molécula homologa al receptor quimioatrayante expresado en Th2, o simplemente ôCRTH2ö para el tratamiento de trastornos inflamatorios. Las variables en la Formula Estructural (1) se definen en la presente. Reivindicacion 1: Un compuesto de formula (1), o una sal farmacéuticamente aceptable del mismo, donde: El anillo A es un aromático monocíclico opcionalmente sustituido; R es -X1-R1; Rx ES -X2-R4; cada uno de X1 y X2 son independientemente -S(O)2-, -C(O)-, o -C(O)NH-; R1 es: A) un grupo aromático o grupo heteroaromático que 5-6 átomos en el anillo, condensado a un anillo heterocíclico monocíclico no aromático o anillo monocíclico aromático o heteroaromático donde el anillo heterocíclico no aromático, el anillo aromático, o el anillo heteroaromático están o opcionalmente sustituido; o B) un grupo aromático o grupo heteroaromático que tiene 5-6 átomos en el anillo, sustituido con: i) T1-V-T-Ry; ii) T1-V-T-M-Ry; o iii) V-R9, donde R9 es un grupo carbocíclico o heterocíclico no aromático opcionalmente sustituido; y donde el grupo aromático o heteroaromático que tiene 5-6 átomos en el anillo está opcionalmente sustituido también con 1-2 grupos seleccionados independientemente representados por Rz; cada Rz se selecciona independientemente entre halogeno, haloalquilo, Ro, -ORo, -O(haloalquilo), -SRo; -NO2, -CN, -N(R')2, -NR'CO2Ro, -NR??C(O)Ro, -NR??NR'C(O)Ro, -N(R??)C(O)N(R')2, -NR'NR??C(O)N(R??)2, -NR??NR'CO2Ro, -C(O)C(O)Ro, -C(O)CH2(O)Ro, -CO2Ro, -C(O)Ro, -C(O)N(Ro)2, -OC(O)Ro, -OC(O)N(Ro)2, -S(O)2Ro, -SO2N(R')2, -S(O)Ro, -NR'SO2N(R')2, -NR'SO2Ro, -C(=S)N(R')2 y -C(=NH)-N(R')2; cada R' es independientemente hidrogeno, alquilo, -C(O)ORo, S(O)2Ro o -C(O)Ro; cada Ro es independientemente hidrogeno o un grupo alquilo, grupo heterocíclico no aromático o grupo aromático y el alquilo, el grupo heterocíclico no aromático y el grupo aromático representados por Ro están opcionalmente sustituidos con uno o más grupos seleccionados independientemente representados por R ; R es R+, -OR+, -O(haloalquilo), -SR+; -NO2, -CN, -N(R+)2, -NHCO2R+, -NHC(O)R+, -NHNHC(O)R+, -NHC(O)N(R+)2, - NHNHC(O)N(R+)2, -NHNHCO2R+, -C(O)C(O)R+, -C(O)CH2(O)R+, -CO2R+, -C(O)R+, -C(O)N(R+)2, -OC(O)R+, -OC(O)N(R+)2, -S(O)2R+, -SO2N(R+)2, -S(O)R+, -NHSO2N(R+)2, -NHSO2R+, -C(=S)N(R+)2 y -C(=NH)-N(R+)2; R+ es -H, un grupo alquilo C1-3, un grupo heteroarilo monocíclico, un grupo heterocíclico no aromático o un grupo fenilo opcionalmente sustituido con alquilo, haloalquilo, alcoxi, haloalcoxi, halo, -CN, -NO2, amina, alquilamina o dialquilamina; o -N(R+)2 es un grupo heterocíclico no aromático, con la condicion de que los grupos heterocíclicos no aromáticos representados por R+ y -N(R+)2 que comprenden una amina de anillo secundario están opcionalmente acilados o alquilados; V es un enlace covalente, -O-, -C(O)-, -N(R')-, -S-, -S(O)-, -C(O)NR5-, - NR5C(O)-, -S(O)2NR5, -NR5S(O)2- o -S(O)2-; T es alquileno C1-10 de cadena lineal; T1 es un enlace covalente o un alquileno C1-10 de cadena lineal, donde T y T1 juntos no contienen más de 10 átomos de carbono y donde T y T1 están opcional e independientemente sustituidos en cualquiera de uno o más de los átomos de carbono sustituibles con haluro, alquilo, gem dialquilo, gem dihalo, haloalquilo, alcoxi, haloalcoxi, espiro cicloalquilo, nitrogeno opcionalmente N-sustituido que contiene un grupo heterocíclico no aromático espiro, amina, alquilamina, dialquilamina, alcoxi o hidroxilo; M es un grupo opcionalmente sustituido seleccionado entre grupo aromático monocíclico, heteroaromático, carbocíclico monocíclico no aromático o heterocíclico; Ry es -C(O)OR5, -C(O)R5, -OC(O)R5, -C(O)N(R5)2, -NR5C(O)R5, -NR5C(O)OR5, -S(O)2R5, -S(O)2COR5, -S(O)2N(R5)2, -NR5S(O)2R5, -NR5S(O)2R5, -S(O)2OR5, -S(O)OR5, -S(O)R5, -SR5, -C(O)NR5S(O)2R5, -CN, -NR5C(O)N(R5)2, -OC(O)N(R5)2, -N(R5)2, - OR5, un grupo heterocíclico no aromático opcionalmente sustituido o un grupo heteroarilo opcionalmente sustituido; con la condicion de que T es C2-10 cuando V es un enlace covalente y T es C2-10 cuando V es -O-, -S- o -N(R??)- y Ry es -CN, -OH, -SH, - N(R5)2; cada R5 es independientemente -H, alquilo, haloalquilo, hidroxialquilo, carboxialquilo, -C(O)OCH2C6H5, -S(O)2CH3, -C(O)OH, -C(O)OMe, -C(O)OEt, C(O)NH2, bencilo, pirrolidinilo, morfolinilo o -N(R5)2 es un grupo heterocíclico no aromático que contiene nitrogeno; R2 es alquilo C1-3; R3 es un grupo monocíclico o bicíclico opcionalmente sustituido seleccionado entre un grupo aromático, heteroaromático, carbocíclico no aromático y heterocíclico no aromático; y R4 es alquilo C1-3 o hidroxialquilo C1-3. Reivindicacion 48: El método de la reivindicacion 46 donde la enfermedad, trastorno o síntoma inflamatorio es rinitis alérgica o asma alérgica. Reivindicacion 53: Un método para preparar un compuesto producto representado por la formula estructural (2), a partir de un compuesto de partida representado por la formula estructural (3), comprendiendo dicho método la etapa de reducir el carbonilo de la amida del compuesto de partida para formar un intermedio y después ciclar el intermedio para formar el compuesto producto, donde -C(O)ORz es un grupo protector de amida.
ARP050101369A 2004-04-07 2005-04-07 Compuestos derivados de quinolina como antagonistas del receptor de pgd2 para el tratamiento de enfermedades inflamatorias y composiciones farmacéuticas que los contienen. AR048528A1 (es)

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EP (1) EP1740547A1 (es)
JP (1) JP2007532555A (es)
KR (1) KR20070002085A (es)
CN (1) CN101018770A (es)
AR (1) AR048528A1 (es)
AU (1) AU2005233125A1 (es)
BR (1) BRPI0509668A (es)
CA (1) CA2561564A1 (es)
CL (1) CL2008000069A1 (es)
CR (1) CR8659A (es)
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MA (1) MA28566B1 (es)
MX (1) MXPA06011540A (es)
NO (1) NO20065107L (es)
RU (1) RU2006138603A (es)
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