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AR043049A1 - Derivados de hidantoina, proceso de preparacion del mismo y composicion farmaceutica - Google Patents

Derivados de hidantoina, proceso de preparacion del mismo y composicion farmaceutica

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Publication number
AR043049A1
AR043049A1 ARP030103319A ARP030103319A AR043049A1 AR 043049 A1 AR043049 A1 AR 043049A1 AR P030103319 A ARP030103319 A AR P030103319A AR P030103319 A ARP030103319 A AR P030103319A AR 043049 A1 AR043049 A1 AR 043049A1
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AR
Argentina
Prior art keywords
alkyl
optionally substituted
halo
group
cycloalkyl
Prior art date
Application number
ARP030103319A
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English (en)
Inventor
Jeremy Nicholas Burrows
Howard Tucker
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Astrazeneca Ab
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Filing date
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Publication of AR043049A1 publication Critical patent/AR043049A1/es

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • 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
    • 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
    • A61P17/06—Antipsoriatics
    • 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
    • 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
    • A61P35/00—Antineoplastic agents
    • 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
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • 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
    • 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
    • C07D233/66—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 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
    • C07D233/72—Two oxygen atoms, e.g. hydantoin
    • C07D233/76—Two oxygen atoms, e.g. hydantoin with substituted hydrocarbon radicals attached to the third ring carbon atom
    • 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
    • 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
    • C07D401/14—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 three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—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
    • C07D413/06—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 only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/10—Spiro-condensed systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (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)
  • Public Health (AREA)
  • Immunology (AREA)
  • Dermatology (AREA)
  • Rheumatology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Vascular Medicine (AREA)
  • Urology & Nephrology (AREA)
  • Pain & Pain Management (AREA)
  • Transplantation (AREA)
  • Pulmonology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

Derivados de hidantoína de la fórmula (1) que son útiles en la inhibición de metaloproteinasas y en particular en la inhibición de la enzima convertidora de TNF-a (TACE). Reivindicación 1: Un compuesto caracterizado porque responde a la fórmula (1) o una sal aceptable para uso farmacéutico del mismo, donde: Y1 e Y2 son O; z es NR8, O ó S; n es 0 o 1; W es CR1R2 o un enlace; V es un grupo de la fórmula (2); donde el grupo de la fórmula (2) está unido a través de nitrógeno a W de la fórmula (1) y a través de carbono * a fenilo de la fórmula (1); t es 0 o 1; B es un grupo seleccionado entre arilo, heteroarilo y heterociclilo donde cada grupo está opcionalmente substituido con uno o más grupos seleccionados en forma independiente entre nitro, trifluorometilo, trifluorometoxi, halo, ciano, alquilo C1-4 (substituido opcionalmente con R9 o alcoxi C1-4 o uno o más halo),alquenilo C2-4 (substituido opcionalmente con halo o R9), alquinilo C2-4 (substituido opcionalmente con halo o R9),cicloalquilo C3-6 (substituido opcionalmente con R9 o uno o más halo), cicloalquenilo C5-6 (substituido opcionalmente con halo o R9), arilo (substituido opcionalmente con halo o alquilo C1-4), heteroarilo (substituido opcionalmente con halo o alquilo C1-4), heterociclilo (substituido opcionalmente con alquilo C1-4), -SR11, -SOR11, -SO2R11, -SO2NR9R10, -NR9SO2R11,- NHCONR9R10, -OR9, -NR9R10, -CONR9R10 y -NR9COR10; o B es alquenilo C2-4 o alquinilo C2-4, donde cada uno está opcionalmente substituido con a grupo seleccionado entre alquilo C1-4, cicloalquilo C3-6, arilo, heteroarilo, heterociclilo donde este grupo está opcionalmente substituido con uno o más halo, nitro, ciano, trifluorometilo, trifluorometoxi, -CONHR9, -CONR9R10, -SO2R11, -SO2NR9R10, -NR9SO2R11, alquilo C1-4 y alcoxi C1-4; R1 y R2 son en forma independiente hidrógeno o un grupo seleccionado entre alquilo C1-6, alquenilo C2-6, alquinilo C2-6, cicloalquilo C3-6 y cicloalquenilo C5-6 donde el grupo puede estar opcionalmente substituido con halo, ciano, hidroxi o alcoxi C1-4; R3, R4, R5 y R6 son en forma independiente hidrógeno o un grupo seleccionado entre alquilo C1-6, alquenilo C2-6,alquinilo C2-6, cicloalquilo C3-6, cicloalquenilo C5-6, arilo, heteroarilo y heterociclilo donde el grupo está opcionalmente substituido con uno o más substituyentes seleccionados en forma independiente entre halo, nitro, ciano, trifluorometilo, trifluorometoxi, alquilo C1-4, alquenilo C2-4, alquinilo C2-4, cicloalquilo C3-6 (substituido opcionalmente con uno o más R17), arilo (substituido opcionalmente con uno o más R17), heteroarilo (substituido opcionalmente con uno o más R17), heterociclilo, -OR18, -SR19, -SOR19, -SO2R19, -COR19, -CO2R18, -CONR18R20, -NR16COR18, -SO2NR18R20 y -NR16SO2R19; o R1 y R3 junto con los átomos de carbono a los cuales están unidos forman un anillo saturado de 3 a 7 miembros que contiene opcionalmente 1 o 2 grupos heteroatómicos seleccionados entre NH, O, S, SO y SO2 donde el anillo está opcionalmente substituido sobre carbono con alquilo, flúor o alcoxi y/o sobre nitrógeno con alquilo, -COalquilo C1-3 o -SO2alquilo C1-3; o R3 y R4 junto con el átomo de carbono a los cuales están unidos forman un anillo saturado de 3 a 7 miembros que contiene opcionalmente 1 o 2 grupos heteroatómicos seleccionados entre NH, O, S, SO y SO2 donde el anillo está opcionalmente substituido sobre carbono con alquilo C1-4, flúor o alcoxi C1-3 y/o sobre nitrógeno con alquilo, -COalquilo C1-3 o -SO2alquilo C1-3; o R3 y R5 junto con los átomos de carbono a los cuales están unidos forman un anillo saturado de 3 a 7 miembros que contiene opcionalmente 1 o 2 grupos heteroatómicos seleccionados entre NH, O, S, SO y SO2 donde el anillo está opcionalmente substituido sobre carbono con alquilo C1-4, flúor o alcoxi C1-3 y/o sobre nitrógeno con alquilo C1-4, -COalquilo C1-3 o -SO2alquilo C1-3; o R5 y R6 junto con el átomo de carbono al cual están unidos forman un anillo saturado de 3 a 7 miembros que contiene opcionalmente 1 o 2 grupos heteroatómicos seleccionados entre NH, O, S, SO y SO2 donde el anillo está opcionalmente substituido sobre carbono con alquilo, flúor o alcoxi y/o sobre nitrógeno con alquilo C1-4, -COalquilo C1-3 o -SO2alquilo C1-3; R7 es hidrógeno o un grupo seleccionado entre alquilo C1-6, alquenilo C2-6, alquinilo C2-6, heteroalquilo, cicloalquilo C3-7, arilo, heteroarilo o heterociclilo donde el grupo está opcionalmente substituido con halo, alquilo C1-4, alcoxi C1-4, cicloalquilo C3-7, heterociclilo, arilo, heteroarilo y heteroalquilo; y donde el grupo puede seleccionarse R7 está opcionalmente substituido sobre el grupo y/o sobre su substituyente opcional con uno o más substituyentes seleccionados en forma independiente entre halo, ciano, alquilo C1-4, nitro, haloalquilo C1-4, heteroalquilo, arilo, heteroarilo, hidroxialquilo C1-4, cicloalquilo C3-7, heterociclilo, alcoxi C1-4alquilo C1-4, haloalcoxi C1-4alquilo C1-4, -COalquilo C1-4, -OR21, -CO2R21, -SR25, -SOR25, -SO2R25, -NR21COR22, -CONR21R22 y -NHCONR21R22; o R3 y R7 junto con los átomos de carbono a los cuales cada uno está unido forman un anillo saturado de 3 a 7 miembros que contiene opcionalmente 1 o 2 grupos heteroatómicos seleccionados entre NH, O, S, SO y SO2 donde el anillo está opcionalmente substituido sobre carbono con alquilo C1-4, flúor o alcoxi C1-3 y/o sobre nitrógeno con alquilo C1-4, -COalquilo C1-3 o -SO2alquilo C1-3; R8 es hidrógeno o metilo; R9 y R10 son en forma independiente hidrógeno, alquilo C1-6 o cicloalquilo C3-6; o R9 y R10 junto con el átomo de nitrógeno al cual están unidos forman un anillo heterocíclico de 4 a 7 miembros; R11 es alquilo C1-6 o cicloalquilo C3-6; R12 y R13 se seleccionan en forma independiente entre hidrógeno, alquilo C1-6 y cicloalquilo C3-6; R14 es hidrógeno, nitrilo, -NR23R24 o alquilo C1-4 (substituido opcionalmente con halo, -OR23 y -NR23R24); R16, R23 y R24 son en forma independiente hidrógeno o alquilo C1-6; R17 se selecciona entre halo, alquilo C1-6, cicloalquilo C3-6 y alcoxi C1-6 ; R18 es hidrógeno o un grupo seleccionado entre alquilo C1-6, cicloalquilo C3-6, cicloalquenilo C5-6, heterociclilo saturado, arilo, heteroarilo, arilalquilo C1-4 y heteroarilalquilo C1-4 donde el grupo está opcionalmente substituido con uno o más halo; R19 y R25 son en forma independiente un grupo seleccionado entre alquilo C1-6, cicloalquilo C3-6, cicloalquenilo C5-6, heterociclilo saturado, arilo, heteroarilo, arilalquilo y heteroarilalquilo donde el grupo está opcionalmente substituido con uno o más halo; R20 es hidrógeno, alquilo C1-6 o cicloalquilo C3-6; o R18 y R20 junto con el átomo de nitrógeno al cual están unidos forman un anillo heterocíclico de 4 a 7 miembros; R21 y R22 son en forma independiente hidrógeno, alquilo C1-4, haloalquilo C1-4, arilo y arilalquilo C1-4. Reivindicación 13: Un proceso para preparar un compuesto de acuerdo con la cláusula 1, caracterizado porque comprende los pasos de convertir una cetona o aldehido de la fórmula (3) a un compuesto de la fórmula (1); y a continuación de ser necesario: i) convertir un compuesto de la fórmula (1) a otro compuesto de la fórmula (1); ii) eliminar cualquier grupo protector; iii) formar una sal o un éster hidrolizable in vivo aceptables para uso farmacéutico.
ARP030103319A 2002-09-13 2003-09-12 Derivados de hidantoina, proceso de preparacion del mismo y composicion farmaceutica AR043049A1 (es)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GBGB0221246.2A GB0221246D0 (en) 2002-09-13 2002-09-13 Compounds

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AR043049A1 true AR043049A1 (es) 2005-07-13

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ARP030103319A AR043049A1 (es) 2002-09-13 2003-09-12 Derivados de hidantoina, proceso de preparacion del mismo y composicion farmaceutica
ARP030103317A AR041250A1 (es) 2002-09-13 2003-09-12 Derivados de sulfonamida como inhibidores de enzimas convertidoras de tnf-alfa

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US (2) US20050256176A1 (es)
EP (2) EP1551826A1 (es)
JP (2) JP2006507248A (es)
KR (1) KR20050042499A (es)
CN (1) CN1681804A (es)
AR (2) AR043049A1 (es)
AU (2) AU2003263347A1 (es)
BR (1) BR0314275A (es)
CA (1) CA2497571A1 (es)
GB (1) GB0221246D0 (es)
IS (1) IS7792A (es)
MX (1) MXPA05002602A (es)
NO (1) NO20051788L (es)
PL (1) PL375877A1 (es)
RU (1) RU2005106353A (es)
TW (2) TW200409769A (es)
UY (1) UY27972A1 (es)
WO (2) WO2004024721A1 (es)
ZA (1) ZA200501677B (es)

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