AR078996A1 - Compuestos de 4-amino-2-butenamida, composicion farmaceutica que lo comprende, uso de los anteriores para preparar un medicamento util para tratar la enfermedad pulmonar obstructiva cronica y procedimiento para la preparacion de dicho compuesto o dicha composicion - Google Patents

Compuestos de 4-amino-2-butenamida, composicion farmaceutica que lo comprende, uso de los anteriores para preparar un medicamento util para tratar la enfermedad pulmonar obstructiva cronica y procedimiento para la preparacion de dicho compuesto o dicha composicion

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Publication number
AR078996A1
AR078996A1 ARP100102946A ARP100102946A AR078996A1 AR 078996 A1 AR078996 A1 AR 078996A1 AR P100102946 A ARP100102946 A AR P100102946A AR P100102946 A ARP100102946 A AR P100102946A AR 078996 A1 AR078996 A1 AR 078996A1
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AR
Argentina
Prior art keywords
alkyl
aryl
heteroaryl
cycloalkyl
amino
Prior art date
Application number
ARP100102946A
Other languages
English (en)
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Glaxo Group Ltd
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Publication date
Application filed by Glaxo Group Ltd filed Critical Glaxo Group Ltd
Publication of AR078996A1 publication Critical patent/AR078996A1/es

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    • 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
    • C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C237/22—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • 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
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • 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
    • A61P11/08—Bronchodilators
    • 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
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    • C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D205/04—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
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    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
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    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
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    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
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    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
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    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
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    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
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    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
    • C07D213/72—Nitrogen atoms
    • C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
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    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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
    • C07D231/38—Nitrogen atoms
    • C07D231/40—Acylated on said nitrogen atom
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    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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
    • C07D277/38—Nitrogen atoms
    • C07D277/44—Acylated amino or imino radicals
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    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
    • C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
    • C07D285/135—Nitrogen atoms
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    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
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    • C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings 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
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    • C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings 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
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    • 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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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Epidemiology (AREA)
  • Pulmonology (AREA)
  • Immunology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Hydrogenated Pyridines (AREA)
  • Pyrane Compounds (AREA)
  • Indole Compounds (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pyridine Compounds (AREA)
  • Furan Compounds (AREA)
  • Medicinal Preparation (AREA)

Abstract

Compuesto de 4-amino-2-butenamida de la formula (1) o una sal farmacéuticamente aceptable del mismo en la que R1 y R2 se seleccionan independientemente cada uno del grupo que consiste en hidrogeno, alquilo C1-8, alquenilo C2-8, alquinilo C2-8, cicloalquilo C3-8, cicloalquenilo C5-8, bicicloalquilo C6-10, heterocicloalquilo, cicloalquil C3-8-alquilo C1-6, cicloalquenil C5-8-alquilo C1-6, heterocicloalquil-alquilo C1-6, arilo, heteroarilo, arilalquilo C1-6 y heteroaril-alquilo C1-6; en donde cualquier alquilo C1-8, alquenilo C2-8 o alquinilo C2-8 está opcionalmente sustituido una a tres veces, independientemente, por CF3, ciano, -CO2-alquilo C1-4, -CONHalquilo C1-4, -CON-alquil C1-4-alquilo C1-4, -SO2-alquilo C1-4, -SO2NH-alquilo C1-4, -SO2N-alquil C1-4-alquilo C1-4, amino, alquil C1-4-amino, alquil C1-4-alquil C1-4-amino, hidroxilo o alcoxi C1-4; y en donde cualquier grupo cicloalquilo, cicloalquenilo, bicicloalquilo o heterocicloalquilo está opcionalmente sustituido una a tres veces, independientemente, por alquilo C1-4, haloalquilo C1-4, ciano, -CO2-alquilo C1-4, -CONH-alquilo C1-4, -CON-alquil C1-4-alquilo C1-4, -SO2-alquilo C1-4 , -SO2NH-alquilo C1-4, -SO2N-alquil C1-4-alquilo C1-4 , amino, alquil C1-4-amino, alquil C1-4-alquil C1-4-amino, hidroxilo, alcoxi C1-4, arilo, o aril-alquilo C1-4, en donde el resto arilo de dicho arilo o arilalquilo C1-4 está opcionalmente sustituido una a tres veces, independientemente, por halogeno, -CF3, alquilo C1-4, hidroxilo o alcoxi C1-4; y en donde cualquier grupo arilo o heteroarilo está opcionalmente sustituido una a tres veces, independientemente, por halogeno, alquilo C1-6, cicloalquilo C3-6, cicloalquenilo C5-6, haloalquilo C1-6, ciano, -CO2-alquilo C1-4, -CONH-alquilo C1-4,-CON-alquil C1-4-alquilo C1-4, -SO2-alquilo C1-4,-SO2NH-alquilo C1-4, -SO2N-alquil C1-4-alquilo C1-4, amino, alquil C1-4amino, alquil C1-4-alquil C1-4-amino, hidroxilo, alcoxi C1-C4, alquil C1-4tio-, arilo, heteroarilo, aril-alquilo C1-4 o heteroarilaiquilo C1-4; en donde cualquier resto arilo o heteroarilo de dicho arilo, heteroarilo, aril-alquilo C1-4 o heteroaril-alquilo C1-4 está opcionalmente sustituido una a tres veces, independientemente, por halogeno, -CF3, alquilo C1-4, hidroxilo o alcoxi C1-4; y en donde cualquier cicloalquilo C3-6 está opcionalmente sustituido una a tres veces, independientemente, por alquilo C1-4, arilo o heteroarilo; en donde dicho arilo o heteroarilo está opcionalmente sustituido una a tres veces, independientemente, por halogeno, -CF3, alquilo C1-4, hidroxilo o alcoxi C1-4; o R1 y R2 tomados junto con el nitrogeno al que están unidos representan un anillo saturado o insaturado de 5 a 7 miembros que contiene opcionalmente otro heteroátomo que es oxígeno, nitrogeno o azufre, en donde dicho anillo está opcionalmente condensado a un anillo cicloalquilo C3-8, heterocicloalquilo, arilo o heteroarilo; o R1 y R2 tomados junto con el nitrogeno al que están unidos representan un sistema anular bicíclico con puente de 6 a 10 miembros opcionalmente condensado a un anillo cicloalquilo C3-8, heterocicloalquilo, arilo o heteroarilo; R3 es hidrogeno, alquilo C1-8, haloalquilo C1-8, alquenilo C2-8, alquinilo C2-8, cicloalquilo C3-6, cicloalquenilo C5-6, cicloalquil C3-6-alquilo C1-4, cicloalquenil C5-6-alquilo C1-4, o aril-alquilo C1-4, en donde el resto arilo del arilalquilo C1-4 está opcionalmente sustituido una a tres veces, independientemente, por halogeno, alquilo C1-4 o -CF3; R4 es hidrogeno, alquilo C1-4, alquenilo C2-5, alquinilo C2-5, cicloalquilo C3-5, cicloalquil C3-4-alquilo C1-2, ciano-alquilo C1-2, hidroxi-alquilo C1-2, metoxi-alquilo C1-2, aril-alquilo C1-2 o heteroaril-alquilo C1-2, en donde el resto heteroarilo de dicho heteroaril-alquilo C1-2 es un anillo aromático de 5 miembros que contiene un heteroátomo que es oxígeno o azufre y que contiene opcionalmente uno o dos átomos de nitrogeno; y R5 es hidrogeno o metilo; o R4 y R5 tomados junto con los átomos mediante los cuales están conectados forman un anillo saturado de 4 a 6 miembros opcionalmente sustituido una o dos veces, independientemente, por halogeno, -CF3, ciano, alquilo C1-4, amino, alquil C1-4-amino, alquil C1-4-alquil C1-4-amino, hidroxilo, alcoxi C1-4 o alquil C1-4-tio-; en donde dicho anillo está opcionalmente condensado a un anillo cicloalquilo C3-5. Reivindicacion 35: Una composicion farmacéutica caracterizada porque comprende el compuesto o sal acorde con una cualquiera de las reivindicaciones 1 a 34, y un excipiente farmacéuticamente aceptable. Reivindicacion 37: Uso del compuesto o sal acorde con una cualquiera de las reivindicaciones 1 a 34, caracterizado porque es para preparar un medicamento util para tratar la enfermedad pulmonar obstructiva cronica. Reivindicacion 39: Un procedimiento para la preparacion del compuesto o sal acorde con la reivindicacion 1, dicho procedimiento caracterizado porque comprende: 1) hacer reaccionar un alfa-aminoaldehído protegido con Boc en N de la formula (2) en la que R3 es como se define en la reivindicacion 1, con un reactivo de Wittig estabilizado con amida de la formula Ph3PCHC(O)NR1R2, en la que R1 y R2 son como se define en la reivindicacion 1, para formar una aminoenamida protegida con Boc en N que tiene la formula (3); 2) desproteger la aminoenamida protegida con Boc en N mediante la retirada del grupo protector Boc para formar una aminoenamida que tiene la formula (4); 3) acoplar la aminoenamida con un alfa-aminoácido protegido con Boc en N de la formula BocNR5CHR4CO2H, en la que R4 y R5 son como se define en la reivindicacion 1, para formar una acilaminoenamida protegida con Boc en N que tiene la formula (4); 4) desproteger la acilaminoenamida protegida con Boc en N mediante la retirada del grupo protector Boc.
ARP100102946A 2009-08-12 2010-08-11 Compuestos de 4-amino-2-butenamida, composicion farmaceutica que lo comprende, uso de los anteriores para preparar un medicamento util para tratar la enfermedad pulmonar obstructiva cronica y procedimiento para la preparacion de dicho compuesto o dicha composicion AR078996A1 (es)

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