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ES2367576T3 - Nuevos compuestos como moduladores de receptores opioides. - Google Patents

Nuevos compuestos como moduladores de receptores opioides. Download PDF

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ES2367576T3
ES2367576T3 ES05728171T ES05728171T ES2367576T3 ES 2367576 T3 ES2367576 T3 ES 2367576T3 ES 05728171 T ES05728171 T ES 05728171T ES 05728171 T ES05728171 T ES 05728171T ES 2367576 T3 ES2367576 T3 ES 2367576T3
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Henry J. Breslin
Chaozhong Cai
Wei He
Robert W. Kavash
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Janssen Pharmaceutica NV
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    • 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
    • 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
    • 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
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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
    • A61K31/4164—1,3-Diazoles
    • A61K31/4174—Arylalkylimidazoles, e.g. oxymetazolin, naphazoline, miconazole
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    • A61K9/2806—Coating materials
    • 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
    • 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
    • A61P1/10—Laxatives
    • 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
    • A61P1/12—Antidiarrhoeals
    • 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
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
    • 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
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • 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
    • A61P25/06—Antimigraine agents
    • 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]
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
    • C07C237/30—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having the nitrogen atom of the carboxamide group bound to hydrogen atoms or to acyclic 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
    • C07D275/04—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D275/06—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems with hetero atoms directly attached to the ring sulfur atom

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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Peptides Or Proteins (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Hydrogenated Pyridines (AREA)
  • Amplitude Modulation (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Steroid Compounds (AREA)
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Abstract

Un compuesto de Formula (I) **Fórmula** en la que: R1 se selecciona entre el grupo que consiste en hidrogeno, alquilo C1-6, cicloalquilo, heterociclilo, arilalquilo (C1- 6) y heteroarilalquilo (C1-6); en la que cuando R1 es fenilalquilo (C1-6), fenilo esta opcionalmente condensado a un heterociclilo o cicloalquilo; en la que cuando R1 es alquilo C1-2, dicho alquilo C1-2 esta opcionalmente sustituido con uno a dos sustituyentes seleccionados independientemente entre el grupo que consiste en alcoxi C1-6, arilo, cicloalquilo, heterociclilo, hidroxi, ciano, amino, alquilamino C1-6, (alquil C1-6)2amino, trifluorometilo y carboxi; y adicionalmente, en la que cuando R1 es alquilo C3-6, dicho alquilo C3-6 esta opcionalmente sustituido con uno a tres sustituyentes seleccionados independientemente entre el grupo que consiste en alcoxi C1-6, arilo, cicloalquilo, heterociclilo, hidroxi, ciano, amino, alquilamino C1-6, (alquil C1-6)2amino, trifluorometilo y carboxi; en la que el cicloalquilo y el heterociclilo de alquilo C1-2 y alquilo C3-6 estan opcionalmente sustituidos con uno a dos sustituyentes seleccionados independientemente entre el grupo que consiste en alquilo C1-6, hidroxialquilo (C1-6), alcoxi C1-6, hidroxi, ciano, amino, alquilamino C1-6, (alquil C1-6)2amino, trifluorometilo, carboxi, arilalcoxicarbonilo (C1-6), alcoxicarbonilo C1-6, aminocarbonilo, alquilaminocarbonilo C1-6, (alquil C1- 6)2aminocarbonilo y aminosulfonilo; ademas, en la que el cicloalquilo y el heterociclilo de R1 estan opcionalmente sustituidos con uno a dos sustituyentes seleccionados independientemente entre el grupo que consiste en alquilo C1-6, hidroxialquilo (C1-6), alcoxi C1-6, hidroxi, ciano, amino, alquilamino C1-6, (alquil C1-6)2amino, trifluorometilo, carboxi, arilalcoxicarbonilo (C1-6), alcoxicarbonilo C1-6, aminocarbonilo, alquilaminocarbonilo C1-6, (alquil C1-6)2aminocarbonilo y aminosulfonilo; ademas, en la que la porcion de arilo y heteroarilo de los sustituyentes R1 arilalquilo (C1-6) y heteroarilalquilo (C1- 6), esta opcionalmente sustituida con uno a tres sustituyentes R11 seleccionados independientemente entre el grupo que consiste en alquilo C1-6; hidroxialquilo (C1-6); alcoxi C1-6; aril C6-10-alquilo (C1-6); aril C6-10-alcoxi (C1-6); arilo C6-10; heteroarilo opcionalmente sustituido con uno a dos sustituyentes seleccionados independientemente entre el grupo que consiste en alquilo C1-4, alcoxi C1-4 y carboxi; cicloalquilo; heterociclilo; ariloxi C6-10; heteroariloxi; cicloalquiloxi; heterocicliloxi; amino; alquilamino C1-6; (alquil C1-6)2amino; cicloalquilaminocarbonilo C3-6; hidroxialquilaminocarbonilo (C1-6); arilaminocarbonilo C6-10 en la que arilo C6-10 esta opcionalmente sustituido con carboxi o alcoxicarbonilo C1-4; heterociclilcarbonilo; carboxi; alcoxicarbonilo C1-6; alcoxicarboniloxi C1-6; alquilcarbonilo C1-6; alquilcarbonilamino C1-6; aminocarbonilo; alquilaminocarbonilo C1-6; (alquil C1- 6)2aminocarbonilo; ciano; halogeno; trifluorometilo; trifluorometoxi; e hidroxi; con la condicion de que no mas de un sustituyente R11 se seleccione entre el grupo que consiste en aril C6-10- alquilo (C1-6); aril C6-10-alcoxi (C1-6); arilo C6-10; heteroarilo opcionalmente sustituido con uno a dos sustituyentes seleccionados independientemente entre el grupo que consiste en alquilo C1-4, alcoxi C1-4 y carboxi; cicloalquilo; heterociclilo; ariloxi C6-10; heteroariloxi; cicloalquiloxi; arilaminocarbonilo C6-10 en la que arilo C6-10 esta opcionalmente sustituido con carboxi o alcoxicarbonilo C1-4; heterociclilcarbonilo y heterocicliloxi; R2 es hidrogeno, alquilo C1-8, hidroxialquilo (C1-8), aril C6-10-alcoxi (C1-6)-alquilo (C1-6) o aril C6-10-alquilo (C1-8); en la que el grupo arilo C6-10 en los sustituyentes que contienen arilo C6-10 de R2 estan opcionalmente sustituidos con uno a dos sustituyentes seleccionados independientemente entre el grupo que consiste en alquilo C1-6, alcoxi C1-6, hidroxi, amino, alquilamino C1-6, (alquil C1-6)2amino, aminocarbonilo, alquilaminocarbonilo C1-6, (alquil C1-6)2aminocarbonilo, ciano, fluor, cloro, bromo, trifluorometilo y trifluorometoxi; y, en la que los sustituyentes alquilo C1-6 y alcoxi C1-6 de arilo estan opcionalmente sustituidos con hidroxi, amino, alquilamino C1-6, (alquil C1- 6)2amino o arilo; A es a-1, opcionalmente sustituido con R3 y R5; en la que A-B es N-C; R3 es de uno a dos sustituyentes seleccionados independientemente entre el grupo que consiste en alquilo C1-6, arilo, arilalquilo (C1-6), arilalquenilo (C2-6), arilalquinilo (C2-6), heteroarilo, heteroarilalquilo (C1-6), heteroarilalquenilo (C2-6), heteroarilalquinilo (C2-6), amino, alquilamino C1-6, (alquil C1-6)2amino, arilamino, heteroarilamino, ariloxi, heteroariloxi, trifluorometilo y halogeno; en la que el arilo, heteroarilo y el arilo y heteroarilo de arilalquilo (C1-6), arilalquenilo (C2-6), arilalquinilo (C2-6), heteroarilalquilo (C1-6), heteroarilalquenilo (C2-6), heteroarilalquinilo (C2-6), arilamino, heteroarilamino, ariloxi y heteroariloxi, estan opcionalmente sustituidos con uno a cinco sustituyentes fluor o uno a tres sustituyentes seleccionados independientemente entre el grupo que consiste en alquilo C1-6, hidroxialquilo (C1-6), alcoxi C1-6, aril C6-10-alquilo (C1-6), aril C6-10-alcoxi (C1-6), arilo C6-10, ariloxi C6-10, heteroarilalquilo (C1-6), heteroarilalcoxi (C1- 6), heteroarilo, heteroariloxi, arilamino C6-10, heteroarilamino, amino, alquilamino C1-6, (alquil C1-6)2amino, carboxialquilamino (C1-6), carboxi, alquilcarbonilo C1-6, alcoxicarbonilo C1-6, alquilcarbonilamino C1-6, aminocarbonilo, alquilaminocarbonilo C1-6, (alquil C1-6)2aminocarbonilo, carboxialquilaminocarbonilo (C1-6), ciano, halogeno, trifluorometilo, trifluorometoxi, hidroxi, alquilsulfonilo C1-6 y alquilsulfonilamino C1-6; con la condicion de que no mas de uno de dichos sustituyentes en la porcion arilo o heteroarilo de R3 se seleccione entre el grupo que consiste en aril C6-10-alquilo (C1-6), aril C6-10-alcoxi (C1-6), arilo C6-10, ariloxi C6-10, heteroarilalquilo (C1-6), heteroarilalcoxi (C1-6), heteroarilo, heteroariloxi, arilamino C6-10, heteroarilamino; y en la que alquilo C1-6 y alquilo C1-6 de arilalquilo (C1-6) y heteroarilalquilo (C1-6) estan opcionalmente sustituidos con un sustituyente seleccionado entre el grupo que consiste en hidroxi, carboxi, alcoxicarbonilo C1-4, amino, alquilamino C1-6, (alquil C1-6)2amino, aminocarbonilo, alquilaminocarbonilo (C1-4), dialquilaminocarbonilo (C1-4), arilo, heteroarilo, arilamino, heteroarilamino, ariloxi, heteroariloxi, arilalcoxi (C1-4) y heteroarilalcoxi (C1-4); R4 es arilo C6-10 o un heteroarilo seleccionado entre el grupo que consiste en furilo, tienilo, pirrolilo, oxazolilo, tiazolilo, imidazolilo, pirazolilo, piridinilo, pirimidinilo, pirazinilo, indolilo, isoindolilo, indolinilo, benzofurilo, benzotienilo, bencimidazolilo, benztiazolilo, benzoxazolilo, quinolizinilo, quinolinilo, isoquinolinilo y quinazolinilo; en la que R4 esta opcionalmente sustituido con uno a tres sustituyentes R41 seleccionados independientemente entre el grupo que consiste en alquilo (C1-6) opcionalmente sustituido con amino, alquilamino C1-6 o (alquil C1- 6)2amino; alcoxi (C1-6); fenilalcoxi (C1-6); fenilalquilcarboniloxi (C1-6) en la que alquilo C1-6 esta opcionalmente sustituido con amino; un heteroarilalquilcarboniloxi (C1-6) no condensado de 5 miembros; un heteroarilo no condensado de 5 miembros; hidroxi; halogeno; aminosulfonilo; formilamino; aminocarbonilo; alquilaminocarbonilo C1-6 en la que alquilo (C1-6) esta opcionalmente sustituido con amino, alquilamino C1-6 o (alquil C1-6)2amino; (alquil C1-6)2aminocarbonilo en la que cada alquilo (C1-6) esta opcionalmente sustituido con amino, alquilamino C1-6 o (alquil C1-6)2amino; heterociclilcarbonilo en la que heterociclilo es un anillo que contiene nitrogeno de 5-7 miembros y dicho heterociclilo esta unido al carbono carbonilo a traves de un atomo de nitrogeno; carboxi; o ciano; y en la que la porcion fenilo de fenilalquilcarboniloxi (C1-6) esta opcionalmente sustituida con alquilo (C1-6)-alcoxi (C1-6), halogeno, ciano, amino o hidroxi; con la condicion de que no mas de un R41 sea alquilo C1-6 sustituido con alquilamino C1-6 o (alquil C1-6)2amino; aminosulfonilo; formilamino; aminocarbonilo; alquilaminocarbonilo C1-6; (alquil C1-6)2aminocarbonilo; heterociclilcarbonilo; hidroxi; carboxi; o un sustituyente que contiene fenilo o heteroarilo; R5 es un sustituyente en un atomo de nitrogeno del anillo A seleccionado entre el grupo que consiste en hidrogeno y alquilo C1-4; R6 es hidrogeno o alquilo C1-6; R7 es hidrogeno o alquilo C1-6; Ra Rb y se seleccionan independientemente entre el grupo que consiste en hidrogeno, alquilo C1-6 y alcoxicarbonilo C1-6; como alternativa, cuando cada uno de Ra y Rb es distinto de hidrogeno, Ra y Rb se toman opcionalmente junto con el atomo de nitrogeno al que ambos estan unidos para formar un anillo monociclico de cinco a ocho miembros; L es O; y enantiomeros, diastereomeros, racematos y sales farmaceuticamente aceptables del mismo.
ES05728171T 2004-03-15 2005-03-14 Nuevos compuestos como moduladores de receptores opioides. Expired - Lifetime ES2367576T3 (es)

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US553342P 2004-03-15

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ES12194058.9T Expired - Lifetime ES2533176T3 (es) 2004-03-15 2005-03-14 Proceso para preparar intermedios de compuestos útiles como moduladores de receptores opioides
ES13173454.3T Expired - Lifetime ES2596434T3 (es) 2004-03-15 2005-03-14 Moduladores de receptores opioides
ES10182349T Expired - Lifetime ES2428008T3 (es) 2004-03-15 2005-03-14 Moduladores de receptores opioides
ES16178050T Expired - Lifetime ES2705077T3 (es) 2004-03-15 2005-03-14 Moduladores de receptores opioides
ES05728171T Expired - Lifetime ES2367576T3 (es) 2004-03-15 2005-03-14 Nuevos compuestos como moduladores de receptores opioides.

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ES12194058.9T Expired - Lifetime ES2533176T3 (es) 2004-03-15 2005-03-14 Proceso para preparar intermedios de compuestos útiles como moduladores de receptores opioides
ES13173454.3T Expired - Lifetime ES2596434T3 (es) 2004-03-15 2005-03-14 Moduladores de receptores opioides
ES10182349T Expired - Lifetime ES2428008T3 (es) 2004-03-15 2005-03-14 Moduladores de receptores opioides
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