AR046615A1 - Pirrolidinas 3-(benzoil)-n-aciladas, como inhibidores de 11-beta-hsd1, utiles en el tratamiento de desordenes metabolicos - Google Patents

Pirrolidinas 3-(benzoil)-n-aciladas, como inhibidores de 11-beta-hsd1, utiles en el tratamiento de desordenes metabolicos

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Publication number
AR046615A1
AR046615A1 ARP040104086A ARP040104086A AR046615A1 AR 046615 A1 AR046615 A1 AR 046615A1 AR P040104086 A ARP040104086 A AR P040104086A AR P040104086 A ARP040104086 A AR P040104086A AR 046615 A1 AR046615 A1 AR 046615A1
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AR
Argentina
Prior art keywords
alkyl
heterocyclyl
amino
carbamoyl
pyrrolidine
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ARP040104086A
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English (en)
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Janet Pease
Peter Barton
Roger Butlin
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Astrazeneca Ab
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Publication of AR046615A1 publication Critical patent/AR046615A1/es

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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
    • 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
    • A61P25/24—Antidepressants
    • 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
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • 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
    • A61P27/02—Ophthalmic agents
    • A61P27/06—Antiglaucoma agents or miotics
    • 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
    • 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
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • A61P31/06—Antibacterial agents for tuberculosis
    • 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
    • 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
    • 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
    • A61P9/12—Antihypertensives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
    • C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • 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
    • C07D401/06—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 only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur 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
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Abstract

Reivindicación 13: Un compuesto caracterizado porque responde a la fórmula (1), en donde: El anillo A se selecciona entre fenilo, piridilo, tienilo, furilo o tiazolilo; R1 es un sustituyente sobre carbono y se selecciona entre halo, nitro, ciano, hidroxi, amino, carboxi, carbamoilo, mercapto, sulfamoilo, C1-4 alquilo, C2-4 alquenilo, C2-4 alquinilo, C1-4 alcoxi, C1-4 alcanoilo, C1-4 alcanoiloxi, N-(C1-4 alquil)amino, N,N-(C1-4 alquil)2amino, C1-4 alcanoilamino, N-(C1-4 alquil)carbamoilo, N,N- (C1-4 alquil)2carbamoilo, C1-4alquil(SO)a en donde a es entre 0 y 2, C1-4 alcoxicarbonilo, N-(C1-4 alquil)sulfamoilo, N,N-(C1-4 alquil)2sulfamoilo, C1-4 alquilsulfonilamino, carbociclilo, heterociclilo, carbociclil(C0-4)alquilen-Z- y heterociclil(C0- 4)alquilen-Z-; en donde R1 puede estar opcionalmente sustituido sobre carbono por uno o más grupos seleccionados entre R3; y en donde si dicho heterociclilo contiene una porción -NH- dicho nitrógeno puede estar opcionalmente sustituido por un grupo seleccionado entre R4; n es 0-5; en donde los valores de R1 pueden ser iguales o diferentes; X es a -C(O)-, -S(O)2-, -C(O)NR11-, -C(S)NR11-, -C(O)O-, -C(=R11)-; en donde R11 se selecciona entre hidrógeno, C1-4 alquilo, carbociclilo y heterociclilo; Y es C1-6 alquilo, C2-6 alquenilo, C2-6 alquinilo, carbociclilo o heterociclilo; en donde Y puede estar opcionalmente sustituido sobre carbono por uno o más R2; en donde si dicho heterociclilo contiene una porción -NH- dicho nitrógeno puede estar opcionalmente sustituido por un grupo seleccionado entre R5; R2 es un sustituyente sobre carbono y se selecciona entre halo, nitro, ciano, hidroxi, amino, carboxi, carbamoilo, mercapto, sulfamoilo, trifluorometilo, trifluorometoxi, C1-4 alquilo, C2- 4 alquenilo, C2-4 alquinilo, C1-4 alcoxi, C1-4 alcanoilo, C1-4 alcanoiloxi, N-(C1-4 alquil)amino, N,N-(C1-4 alquil)2amino, C1-4 alcanoilamino, N-(C1-4 alquil)carbamoilo, N,N-(C1-4 alquil)2carbamoilo, C1- 4alquil(SO)a en donde a es entre 0 y 2, C1-4 alcoxicarbonilo, C1-4 alcoxicarbonilamino, C1-4 alcoxicarbonil-N-(C1-4 alquil)amino, N-(C1-4 alquil)sulfamoilo, N,N-(C1-4 alquil)2sulfamoilo, C1-4 alquilsulfonilamino, aminotiocarboniltio, N-(C1-4 alquil)aminotiocarboniltio, N,N-(C1-4 alquil)2aminotiocarboniltio, carbociclilo, heterociclilo, carbociclil(C0-4)alquilen-Z- y heterociclil(C0-4)alquilen-Z-; en donde R2 puede estar opcionalmente sustituido sobre carbono por uno o más grupos seleccionados entre R6; y en donde si dicho heterociclilo contiene una porción -NH- dicho nitrógeno puede estar opcionalmente sustituido por un grupo seleccionado entre R7; R3 y R6 se seleccionan en forma independiente entre halo, nitro, ciano, hidroxi, amino, carboxi, carbamoilo, mercapto, sulfamoilo, trifluorometilo, trifluorometoxi, C1-4 alquilo, C2-4 alquenilo, C2-4 alquinilo, C1-4 alcoxi, C1-4 alcanoilo, C1-4 alcanoiloxi, N-(C1-4 alquil)amino, N,N-(C1-4 alquil)2amino, C1-4 alcanoilamino, N-(C1-4 alquil)carbamoilo, N,N-(C1-4 alquil)2carbamoilo, C1-4alquil(SO)a en donde a es entre 0 y 2, C1-4 alcoxicarbonilo, C1-4 alcoxicarbonilamino, C1-4 alcoxicarbonil-N-(C1-4 alquil)amino, N-(C1-4 alquil)sulfamoilo, N,N-(C1-4 alquil)2sulfamoilo, C1-4 alquilsulfonilamino, carbociclilo, heterociclilo, carbociclil(C0-4)alquilen-Z- y heterociclil(C0-4)alquilen-Z-; en donde R3 y R6 pueden estar sustituidos en forma independiente sobre carbono por uno o más R8; y en donde si dicho heterociclilo contiene una porción -NH- dicho nitrógeno puede estar opcionalmente sustituido por un grupo seleccionado entre R13; R4, R5, R7 y R13 se seleccionan en forma independiente entre C1-4 alquilo, C1-4 alcanoilo, C1-4 alquilsulfonilo, C1-4 alcoxicarbonilo, carbamoilo, N-(C1-4 alquil)carbamoilo, N,N-(C1-4 alquil)2carbamoilo, bencilo, benciloxicarbonilo, benzoilo y fenilsulfonilo; R8 se selecciona entre halo, nitro, ciano, hidroxi, trifluorometoxi, trifluorometilo, amino, carboxi, carbamoilo, mercapto, sulfamoilo, metilo, etilo, metoxi, etoxi, acetilo, acetoxi, metilamino, etilamino, dimetilamino, dietilamino, N-metil-N-etilamino, acetilamino, N-metilcarbamoilo, N-etilcarbamoilo, N,N-dimetilcarbamoilo, N,N-metilcarbamoilo, N- metil-N-etilcarbamoilo, metiltio, etiltio, metilsulfinilo, etilsulfinilo, mesilo, etilsulfonilo, metoxicarbonilo, etoxicarbonilo, N-metilsulfamoilo, N-etilsulfamoilo, N,N-dimetilsulfamoilo, N,N-dietilsulfamoilo o N-metil-N-etilsulfamoilo; R12 es hidroxi, metilo, etilo, propilo o trifluorometilo; m es 0 ó 1; Z es -S(O)a-, -O-, -NR10-, -C(O)-, -C(O)NR10-, -NR10C(O)-, -OC(O)NR10- o -SO2NR10-; en donde a es entre 0 y 2; en donde R10 se selecciona entre hidrógeno y C1-4 alquilo; o una sal aceptable para uso farmacéutico del mismo, con la salvedad de que dicho compuesto no sea: 1-(fenilsulfonil)-3-(4-metoxibenzoil)pirrolidina; 1-(etoxicarbonil)-3-(benzoil)pirrolidina; 1-(acetil)-3-(benzoil)pirrolidina; 1-(fenilsulfonil)-3-(4- metilbenzoil)pirrolidina; 1-[N- (ciclopentil)anilinocarbonil]-3-(benzoil)pirrolidina, 1-(benzoil)-3-(4-mesilaminobenzoil)pirrolidina; 1-(N-metilcarbamoil)-3(3-trifluorometilbenzoil)pirrolidina; 1-(fenilsulfonil)-3-(2-metilbenzoil)pirrolidina; o 1- (fenilsulfonil)-3- (benzoil)pirrolidina.
ARP040104086A 2003-11-05 2004-11-05 Pirrolidinas 3-(benzoil)-n-aciladas, como inhibidores de 11-beta-hsd1, utiles en el tratamiento de desordenes metabolicos AR046615A1 (es)

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GBGB0325745.8A GB0325745D0 (en) 2003-11-05 2003-11-05 Chemical compounds

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US (1) US20070219266A1 (es)
EP (1) EP1685101A1 (es)
JP (1) JP2007510702A (es)
CN (1) CN1902172A (es)
AR (1) AR046615A1 (es)
GB (1) GB0325745D0 (es)
TW (1) TW200519085A (es)
UY (1) UY28602A1 (es)
WO (1) WO2005047250A1 (es)

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TW200519085A (en) 2005-06-16
WO2005047250A1 (en) 2005-05-26
EP1685101A1 (en) 2006-08-02
JP2007510702A (ja) 2007-04-26
UY28602A1 (es) 2005-06-30
GB0325745D0 (en) 2003-12-10
US20070219266A1 (en) 2007-09-20

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