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HK1065779A1 - Aryl aniline beta-2 adrenergic receptor agonists - Google Patents

Aryl aniline beta-2 adrenergic receptor agonists Download PDF

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Publication number
HK1065779A1
HK1065779A1 HK04108592.1A HK04108592A HK1065779A1 HK 1065779 A1 HK1065779 A1 HK 1065779A1 HK 04108592 A HK04108592 A HK 04108592A HK 1065779 A1 HK1065779 A1 HK 1065779A1
Authority
HK
Hong Kong
Prior art keywords
hydroxy
compound
alkyl
ethyl
aminophenyl
Prior art date
Application number
HK04108592.1A
Other languages
German (de)
English (en)
Chinese (zh)
Other versions
HK1065779B (en
Inventor
Edmund J. Moran
John R. Jacobsen
Michael R. Leadbetter
Matthew B. Nodwell
Sean G. Trapp
James Aggen
Timothy J. Church
Original Assignee
Theravance, Inc.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Theravance, Inc. filed Critical Theravance, Inc.
Publication of HK1065779A1 publication Critical patent/HK1065779A1/en
Publication of HK1065779B publication Critical patent/HK1065779B/en

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    • C07—ORGANIC CHEMISTRY
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    • C07D213/00—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
    • 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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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
    • C07C215/68—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings and hydroxy groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • 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
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    • 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
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    • A61P15/06—Antiabortive agents; Labour repressants
    • A—HUMAN NECESSITIES
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    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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    • C07C215/56—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by hydroxy groups
    • C07C215/58—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by hydroxy groups with hydroxy groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain
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    • C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
    • C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
    • C07C217/84—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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    • C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
    • C07C233/42—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
    • C07C233/43—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of a saturated carbon skeleton
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    • C07C317/32—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C317/34—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring
    • C07C317/36—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring with the nitrogen atoms of the amino groups bound to hydrogen atoms or to carbon atoms
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    • C07D413/12—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 chain containing hetero atoms as chain links

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Claims (24)

  1. Un composé de formule (I) dans laquelle:
    - chacun des substituants R1-R5 est, indépendamment l'un de l'autre, choisi dans le groupe consistant en l'atome d'hydrogène, les radicaux alkyl, alcényl, alcynyl, aryl, hétéroaryl, cycloalkyl, hétérocyclyl et Ra; ou
    - R1 et R2, R2 et R3, R3 et R4 ou R4 et R5 sont joints entre eux pour former un groupe choisi dans le groupe consistant en -C(Rd)=C(Rd)C(=O)NRd-, -CRdRd-CRdRd-C(=O)NRd-, -NRaC(=O)C(Rd)=C(Rd)-, -NRdC(=O)CRdRd-CRdRd-, -NRdC(=O)S-, -(CRdRd)p-, -SC(=O)NRd-, -S(CRdRd)q-, -(CRdRd)qS-, -S(CRdRd)rO-, -O(RdRd)rS-, ou -NHC(Rj)=C(Rk)-;
    - R6 est l'atome d'hydrogène, un radical alkyl ou alkoxy;
    - R7 est l'atome d'hydrogène ou un radical alkyl;
    - R8 est l'atome d'hydrogène ou un radical alkyl; ou R8 ensemble avec R9 forment un radical -CH2- ou -CH2CH2-;
    - R9 est, indépendamment l'un de l'autre, choisi dans le groupe comprenant les radicaux alkyl, alcényl, alcynyl, aryl, hétéroaryl, cycloalkyl, hétérocyclyl et Ra
    ou R9 ensemble avec R8 forment un radical -CH2- ou -CH2CH2- R10 est l'atome d'hydrogène ou un radical alkyl; R11, R12 et R13 sont, indépendamment l'un de l'autre, choisis dans le groupe comprenant l'atome d'hydrogène, les radicaux alkyl, cycloalkyl, alcényl, alcynyl, aryl, hétéroaryl, hétérocyclyl, -NO2, un atome d'halogène, -NRdRe, -C(=O)Rd, -CO2Rd, -OC(=O)Rd, -CN, -C(=O)NRdRe, -NRdC(=O)Re, -OC(=O)NRdRe, -NRdC(=O)ORe, -NRdC(=O)NRaRe, -ORd, -S(O)mRd, -NRd-NRd-C(=O)Rd, -NRd-N=CRdRd, -N(NRdRe)Rd et -S(O)2NRdRe; ou R11 et R12, ensemble avec les atomes auxquels ils sont attachés, forment un cycle benzo fusionné, lequel cycle benzo peut éventuellement être substitué par 1, 2, 3 ou 4 substituants Rc; ou R11 et R12, ensemble avec les atomes auxquels ils sont attachés, forment un noyau hétérocyclique; où:
    pour R1-R6, R9 et R11-R13, chacun des radicaux alkyl, alcényl et alcynyl est éventuellement substitué par Rm ou par 1, 2, 3 ou 4 substituants, choisis, indépendamment les uns des autres, parmi ceux cités pour Rb;
    pour R1-R6, R9 et R11-R13, chacun des radicaux aryl et hétéroaryl est éventuellement substitué par 1, 2, 3 ou 4 substituants, choisis, indépendamment les uns des autres, parmi ceux cités pour Rc et
    pour R1-R6, R9 et R11-R13 chacun des radicaux cycloalkyl et hétérocyclyl est éventuellement substitué par 1, 2, 3 ou 4 substituants, choisis, indépendamment les uns des autres, parmi ceux cités pour Rb et Rc;
    chaque Ra est, indépendamment l'un de l'autre, un groupe -ORd, -NO2, un atome d'halogène, -S(O)mRd, -S(O)2ORd, -S(O)mNRdRe, -NRdRe, -O-(CRfNRg)nNRdRe, -C(=O)Rd, -CO2Rd, -CO2(CRfRg)nCONRdRe, -OC(=O)Rd, -CN, -C(=O)NRdRe, -NRdC(=O)Re, -OC(=O)NRdRe, -NRdC(=O)ORe, -NRdC(=O)NRdRe, -CRd(=N-ORe), -CF3 ou -OCF3;
    chaque Rb est, indépendamment l'un de l'autre, un groupe Ra, oxo ou =N-ORe;
    chaque Rc est, indépendamment l'un de l'autre, un radical Ra, alkyl, alcényl ou alcynyl; où chaque alkyl, alcényl et alcynyl est éventuellement substitué par 1, 2, 3 ou 4 substituants choisis, indépendamment les uns des autres, parmi ceux cités pour Rb;
    chaque Rd et Re est, indépendamment l'un de l'autre, un atome d'hydrogène, un radical alkyl, alcényl, alcynyl, aryl, hétéroaryl, cycloalkyl ou hétérocyclyl; où chaque alkyl, alcényl, alcynyl, aryl, hétéroaryl, cycloalkyl et hétérocyclyl est éventuellement substitué par 1, 2, 3 ou 4 substituants, choisis, indépendamment les uns des autres, parmi ceux cités pour Rh;
    ou Rd et Re, ensemble avec les atomes auxquels ils sont attachés, forment un noyau hétérocyclique comportant de 5 à 7 atomes dans le noyau, le noyau hétérocyclique contenant éventuellement 1 ou 2 hétéroatomes supplémentaires, choisis indépendamment les uns des autres, parmi les atomes d'oxygène, de soufre ou d'azote;
    chaque Rf et Rg est, indépendamment l'un de l'autre, un atome d'hydrogène, un radical alkyl, aryl, hétéroaryl, cycloalkyl ou hétérocyclyl; où chaque alkyl, aryl, hétéroaryl, cycloalkyl et hétérocyclyl est éventuellement substitué par 1, 2, 3 ou 4 substituants, choisis, indépendamment les uns des autres, parmi ceux cités pour Rh;
    ou Rf et Rg, ensemble avec l'atome de carbone auquel ils sont liés forment un noyau comportant 5 à 7 atomes dans le noyau, le noyau contenant éventuellement 1 ou 2 hétéroatomes et sont choisis indépendamment l'un de l'autre, parmi les atomes d'oxygène, de soufre ou d'azote;
    chaque Rh est, indépendamment l'un de l'autre, un halogène, (C1-8)-alkyl, (C1-8)-alkoxy, -S-(C1-8)-alkyl, aryl, (aryl)-(C1-6)-alkyl, (aryl)-(C1-8)-alkoxy, hétéroaryl, (hétéroaryl)-(C1-6)-alkyl, (hétéroaryl)-(C1-8)-alkoxy, hydroxy, -NH(C1-6)-alkyl, -N[(C1-6)-alkyl]2, -OC(=O)(C1-6)-alkyl, -C(=O)(C1-6)-alkyl, amino, -C(=O)-O-(C1-6)-alkyl, -NHC(=O)(C1-6)-alkyl, -C(=O)NH(C1-6)-alkyl, carboxy, nitro, -CN ou -CF3;
    Rj et Rk, ensemble avec les atomes de carbone auxquels ils sont liés forment un noyau phényl qui est éventuellement substitué par 1, 2, 3 ou 4 substituants Rc;
    chaque Rm est, indépendamment l'un de l'autre, un radical aryl, hétéroaryl, cyclo-alkyl ou hétérocyclyl; chaque aryl ou hétéroaryl étant éventuellement substitué par 1, 2, 3 ou 4 substituants, choisis parmi ceux cités pour Rc et chaque radical cycloalkyl et hétérocyclyl étant éventuellement substitué par 1, 2, 3 ou 4 substituants, choisis parmi ceux cités pour Rb;
    m est 0, 1 ou 2;
    n est 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 ou 10;
    p est 3, 4 ou 5;
    q est 2, 3 ou 4;
    r est 1, 2 ou 3; et
    w est 0, 1, 2, 3 ou 4;
    ou un sel, solvate ou stéréoisomère pharmaceutiquement acceptable en dérivant
  2. Le composé selon la revendication 1, dans laquelle R1 est un atome d'hydrogène; R2 est un atome d'hydrogène; R3 est un groupe hydroxy; et R4 et R5 forment ensemble -NHC(=O)CH=CH-.
  3. Le composé selon la revendication 1, dans lequel
    - chacun des substituants R1-R5 est, indépendamment l'un de l'autre, choisi dans le groupe consistant en un atome d'hydrogène, le radical alkyl et Ra; dans lequel chaque Ra est, indépendamment l'un de l'autre, un groupe -ORd, un atome d'halogène, -NRdRe, -NRdC(=O)Re ou -OC(=O)NRdRe;
    ou R1 et R2 ou R4 et R5, joints entre eux forment un groupe consistant en -C(Rd)=C(Rd)C(=O)NRd-, -CRdRd -CRdRd -C(=O)NRd-, -NRdC(=O)C(Rd)=C(Rd)-, NRdC(=O)CRdRd-CRdRd, -NRdC(=O)S- ou -SC(=O)NRd-; R6, R8 et R10 sont tous des atomes d'hydrogène; chacun des R11 et R12 est, indépendamment l'un de l'autre, choisi dans le groupe consistant en un atome d'hydrogène, les radicaux alkyl, cycloalkyl, alcényl, alcynyl, aryl, hétéroaryl, hétérocyclyl, -NO2, les halogènes, -NRdRe, -CO2Rd, -OC(=O)Rd, -CN, -C(=O)NRdRe, -NRdC(=O)Re, -ORd, -S(O)mRd, -NRd-NRd-C(=O)Rd, -NRa-N=CRdRd, -N(NRdRe)Rd et -S(O)2NRdRe; où pour R1-R5, R11 et R12, chaque radical alkyl est éventuellement substitué par Rm ou par 1, 2, 3 ou 4 substituants, choisis, indépendamment les uns des autres, parmi ceux cités pour Rb; pour R11 et R12, chaque radical aryl et hétéroaryl est éventuellement substitué par 1, 2, 3 ou 4 substituants, choisis, indépendamment les uns des autres, parmi ceux cités pour Rc, et pour R11 et R12, chaque radical cycloalkyl et hétérocyclyl est éventuellement substitué par 1, 2, 3 ou 4 substituants, choisis, indépendamment les uns des autres, parmi ceux cités pour Rb et Rc;
    - R13 est un atome d'hydrogène;
    - le groupe comprenant -NR10 est en position méta ou para par rapport au groupe comprenant R7; et
    - w est 0, 1 ou 2.
  4. Le composé selon l'une quelconque des revendications 1-3, dans laquelle :
    - R7 est un atome d'hydrogène;
    - chacun des R11 et R12 est, indépendamment l'un de l'autre, choisi dans le groupe consistant en un atome d'hydrogène, les radicaux (C1-6)-alkyle, cyclohexyl, phényl, pyrazolinyl, -ORd, -S(O)mRd et -S(O)2NRdRe;
    - w est 0; et
    - Rd et Re sont choisis, indépendamment l'un de l'autre, dans le groupe consistant en un atome d'hydrogène, les radicaux (C1-6)-alkyl, phényl, -CF3 et (C1-3)-alkyl, pyridyl, thiazolyl, pyrimidinyl et pyrazolinyl, chaque radical phényl étant éventuellement substitué par 1 ou 2 substituants, choisis indépendamment l'un de l'autre, parmi un atome d'halogène, -CF3 et (C1-3)-alkyl, chaque radical pyrimidinyl est éventuellement substitué par 1 ou 2 substituants, choisis indépendamment l'un de l'autre, parmi (C1-3)-alkyl et -O-(C1-3)-alkyl et chaque radical pyrazolinyl est éventuellement substitué par 1 ou 2 substituants, choisis indépendamment l'un de l'autre, parmi les groupes (C1-3)-alkyl et carboxy;
    ou Rd et Re, ensemble avec l'atome d'azote auxquels ils sont liés sont des radicaux morpholino ou piperidino.
  5. Le composé selon l'une quelconque des revendications 1-4, dans laquel R11 est l'atome d'hydrogène ou le radical phényl et R12 est -O-(C1-3)-alkyl; ou R11 est le radical phényl et R12 est l'atome d'hydrogène.
  6. Un composé selon la revendication 1 de formule (II) dans laquelle:
    - R4 est -CH2OH ou -NHCHO et R5 est l'atome d'hydrogène; ou R4 et R5 forment ensemble un radical -NHC(=O)CH=CH-;
    - R11 est un radical phényl ou hétéroaryl, où chaque radical phényl est éventuellement substitué par 1 ou 2 substituants choisis parmi un atome d'halogène,
    - ORd, -CN, -NO2, -SO2Rd, -C(=O)NRdRe, -C(=O)Rd et (C1-3)-alkyl, où (C1-3)-alkyl est éventuellement substitué par 1 ou 2 substituants choisis parmi les substituants carboxy, hydroxy et amino et chaque Rd et Re est, indépendamment l'un de l'autre, un atome d'hydrogène ou un radical (C1-3)-alkyl; et chaque radical hétéroaryl est éventuellement substitué par 1 ou 2 substituants (C1-3)-alkyl; et
    - R12 est un atome d'hydrogène ou un radical -O-(C1-6)-alkyl;
    ou un sel, solvate ou stéréoisomère pharmaceutiquement acceptable en dérivant.
  7. Le composé selon la revendication 6, dans laquelle R11 est un radical phényl, éventuellement substitué par un substituant choisi parmi un atome d'halogène, -ORd, -CN, -NO2, -SO2Rd, -C(=O)Rd et (C1-3)-alkyl, où (C1-3)-alkyl est éventuellement substitué par 1 ou 2 substituants choisis parmi les carboxy, hydroxy et amino et Rd est un atome d'hydrogène ou un radical (C1-3)-alkyl.
  8. Le composé selon la revendication 6, dans laquelle
    - R11 est un radical phényl, pyridyl ou thiophényl, chaque radical phényl étant éventuellement substitué par un substituant choisi dans le groupe consistant en l'atome de chlore et les radicaux -OCH3, -CN et -CH2NH2; et
    - R12 est un atome d'hydrogène, un radical -OCH3 ou un radical -OC2H5.
  9. Le composé selon la revendication 8, dans lequel:
    - R4 et R5 forment ensemble un groupe -NHC(=O)CH=CH-;
    - R11 est un radical phényl ou pyridyl, chaque radical phényl étant éventuellement substitué par un substituant choisi dans le groupe consistant en l'atome de chlore ou les radicaux -OCH3, -CN et -CH2NH2; et R12 est le radical -OCH3.
  10. Le composé selon l'une quelconque des revendications 6-9, dans laquelle le composé est un mélange de stéréoisomères dans lequel la proportion de stéréoisomères présentant la configuration (R) au centre chiral auquel le groupe hydroxy est lié est supérieure à la proportion de stéréoisomères présentant la configuration (S) au centre chiral auquel le groupe hydroxy est attaché.
  11. Le composé selon l'une des revendications 6-9, dans laquelle le composé est un stéréoisomère présentant la configuration (R) au centre chiral auquel le groupe hydroxy est attaché.
  12. Le composé selon la revendication 6, dans laquelle le composé est choisi dans le groupe consistant en:
    N-{2-[4-(3-phényl-4-méthoxyphényl)aminophényl]éthyl}-(R)-2-hydroxy-2-(3-hydroxyméthyl-4-hydroxyphényl)éthylamine;
    N-{2-[4-(4-éthoxyphényl)aminophényl]éthyl}-(R)-2-hydroxy-2-(3-hydroxyméthyl-4-hydroxyphényl)éthylamine;
    N-{2-[4-(3-phénylphényl)aminophényl]éthyl}-(R)-2-hydroxy-2-(3-hydroxyméthyl-4-hydroxyphényl)éthylamine;
    N-{2-[4-(3-phényl-4-méthoxyphényl)aminophényl]éthyl}-(R)-2-hydroxy-2-[8-hydroxy-2(1H)-quinolinon-5-yl]éthylamine;
    N-{2-{4-(4-méthoxyphényl)aminophényl]éthyl}-(R)-2-hydroxy-2-(3-hydroxyméthyl-4-hydroxyphényl)éthylamine;
    N-{2-[4-(3-phényl-4-éthoxyphényl)aminophényl]éthyl}-(R)-2-hydroxy-2-(3-hydroxyméthyl-4-hydroxyphényl)éthylamine;
    N-{2-[4-(3-phényl-4-méthoxyphényl)aminophényl]éthyl}-(R)-2-hydroxy-2-(3-formamido-4-hydroxyphényl)éthylamine;
    N-{2-[4-(4-éthoxyphényl)aminophényl]éthyl}-(R)-2-hydroxy-2-(3-formamido-4-hydroxyphényl)éthylamine;
    N-{2-[4-(3-phénylphényl)aminophényl]éthyl}-(R)-2-hydroxy-2-(3-formamido-4-hydroxyphényl)éthylamine;
    N-{2-(4-(3-phényl-4-éthoxyphényl)aminophényl]éthyl}-(R)-2-hydroxy-2-(3-formamido-4-hydroxyphényl)éthylamine;
    N-{2-[4-(4-méthoxyphényl)aminophényl)éthyl}-(R)-2-hydroxy-2-(3-formamido-4-hydroxyphényl)éthylamine;
    N-{2-(4-(4-éthoxyphényl)aminophényl]éthyl}-(R)-2-hydroxy-2-[8-hydroxy-2(1H)-quinolinon-5-yl]éthylamine;
    N-{2-[4-(3-phénylphényl)aminophényl)éthyl}-(R)-2-hydroxy-2-[8-hydroxy-2(1H)-quinolinon-5-yl]éthylamine;
    N-{2-[4-(3-phényl-4-éthoxyphényl)aminophényl)éthyl}-(R)-2-hydroxy-2-[8-hydroxy-2(1H)-quinolinon-5-yl]éthylamine; et
    N-{2-[4-(4-méthoxyphényl)aminophényl)éthyl}-(R)-2-hydroxy-2-[8-hydroxy-2(1H)-quinolinon-5-yl]éthylamine.
  13. Le composé selon la revendication 6, dans lequel le composé est choisi dans le groupe consistant en:
    - N-{2-[4-(3-(2-chlorophényl)phényl)aminophényl)-éthyl}-(R)-2-hydroxy-2-[8-hydroxy-2(1H)-quinolinon-5-yl]éthylamine;
    - N-{2- [4-(3 -(2-méthoxyphényl)phényl)aminophényl] ethyl}-(R)-2-hydroxy-2-[8-hydroxy-2(1H)-quinolinon-5-yl] éthylamine;
    - N-{2-[4-(3-(3-cyanophényl)phényl)aminophényl]éthyl}-(R)-2-hydroxy-2-[8-hydroxy-2(1H)-quinolinon-5-yl]éthylamine;
    - N-{2-[4-(3-(4-aminométhylphényl)phényl)aminophényl]-éthyl}-(R)-2-hydroxy-2-[8-hydroxy-2(1H)-quinolinon-5-yl]éthylamine;
    - N-{2-[4-(3-(3-chlorophényl)phényl)aminophényl]éthyl}-(R)-2-hydroxy-2-[8-hydroxy-2(1H)-quinolinon-5-yl]éthylamine;
    - N-{2-[4-(3-(4-aminométhylphényl)-4-méthoxyphényl)aminophényl]éthyl}-(R)-2-hydroxy-2-[8-hydroxy-2(1H)-quinolinon-5-yl]éthylamine;
    - N-{2-[4-(3-(3-cyanophényl)-4-méthoxyphényl)aminophényl]éthyl}-(R)-2-hydroxy-2-[8-hydroxy-2(1H)-quinolinon-5-yl]éthylamine;
    - N-{2-[4-(3-(4-hydroxyphényl)-4-méthoxyphényl)aminophényl]-éthyl}-(R)-2-hydroxy-2-[8-hydroxy-2(1H)-quinolinon-5-yl]-éthylamine;
    - N-{2-(4-(3-(3-pyridyl)phényl)aminophényl]-éthyl}-(R)-2-hydroxy-2-[8-hydroxy-2(1H)-quinolinon-5-yl] éthylamine;
    - N-{2-(4-(3 -(3 -pyridyl)-4-méthoxyphényl)aminophényl]éthyl}-(R)-2-hydroxy-2-[8-hydroxy-2(1H)-quinolinon-5-yl]éthylamine
    - N-{2-(4-(3-(4-pyridyl)-4-méthoxyphényl)aminophényl]éthyl}-(R)-2-hydroxy-2-[8-hydroxy-2(1H)-quinolinon-5-yl] éthylamine;
    - N-{2-(4-(3-(thiophén-3-yl)-4-méthoxyphényl)aminophényl]éthyl}-(R)-2-hydroxy-2-[8-hydroxy-2(1H)-quinolinon-5-yl]éthylamine; et
    - N-{2-(4-(3-(3-chlorophényl)-4-méthoxyphényl)aminophényl]éthyl}-(R)-2-hydroxy-2-[8-hydroxy-2(1H)-quinolinon-5-yl] éthylamine.
  14. Le composé selon la revendication 6, ledit composé consistant en N-{2-[4-(3-phényl-4-méthoxyphényl)aminophényl]éthyl}-(R)-2-hydroxy-2-[8-hydroxy-2 {1H)-quinolinon-5-yl]éthylamine.
  15. Le composé selon la revendication 6, ledit composé consistant en N-{2-[4-(3-(3-chlorophényl)-4-méthoxyphényl)aminophényl]éthyl}-(R)-2-hydroxy-2-[8-hydroxy-2(1H)-quinolinon-5-yl]éthylamine.
  16. Une composition pharmaceutique comprenant une quantité thérapeutiquement efficace d'un composé selon l'une quelconque des revendications 1-15 et un support pharmaceutiquement acceptable.
  17. La composition pharmaceutique selon la revendication 16, laquelle composition étant sous une forme convenant à une administration par inhalation.
  18. La composition pharmaceutique selon la revendication 16, laquelle composition comprenant en outre une quantité thérapeutiquement efficace d'un agent anti-inflammatoire stéroïdien
  19. La composition pharmaceutique selon la revendication 16, laquelle composition comprend en outre une quantité thérapeutiquement efficace d'un composé choisi dans le groupe consistant en un agent antagoniste récepteur muscarinique, un agent inhibiteur de la phosphodiestérase, un anticorps immunoglobuline, un agent antagoniste de la leucotriène, un agent antagoniste de la cytokine, un inhibiteur de protéase, l'acide cromoglycique, le sodium nédocromil et le sodium cromoglycate.
  20. Un composé tel que revendiqué dans l'une quelconque des revendications 1-15 pour son utilisation en thérapie médicale.
  21. L'emploi d'un composé tel que revendiqué dans l'une quelconque des revendications 1-15 ou une composition pharmaceutique telle que revendiquée dans l'une quelconque des revendications 16-19 pour la fabrication d'un médicament pour traiter chez un mammifère une maladie ou une affection associée à l'activité du récepteur β2 adrénergique.
  22. L'utilisation selon la revendication 21, dans laquelle la maladie ou l'affection est une maladie pulmonaire.
  23. L'utilisation selon la revendication 22, dans laquelle la maladie pulmonaire est l'asthme ou une affection pulmonaire chronique obstructive.
  24. L'utilisation selon la revendication 21, dans laquelle la maladie ou l'affection est choisie dans le groupe consistant en les accouchements prématurés, les désordres neurologiques, les maladies cardiaques et les inflammations.
HK04108592.1A 2001-11-13 2002-11-12 Aryl aniline beta-2 adrenergic receptor agonists HK1065779B (en)

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PCT/US2002/036237 WO2003042164A1 (fr) 2001-11-13 2002-11-12 Agonistes arylaniline des recepteurs adrenergiques $g(b)2

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DK1446379T3 (da) 2009-07-27
RU2298545C2 (ru) 2007-05-10
AR037355A1 (es) 2004-11-03
PT1446379E (pt) 2009-06-26
KR20050044400A (ko) 2005-05-12
HUP0401876A3 (en) 2008-03-28
US7125892B2 (en) 2006-10-24
US20060178410A1 (en) 2006-08-10
US6670376B1 (en) 2003-12-30
NZ532030A (en) 2006-08-31
TWI249515B (en) 2006-02-21
TW200303298A (en) 2003-09-01
SI1446379T1 (sl) 2009-08-31
EP1446379B1 (fr) 2009-04-29
JP4303113B2 (ja) 2009-07-29
KR100908438B1 (ko) 2009-07-21
WO2003042164A1 (fr) 2003-05-22
RU2004117887A (ru) 2005-04-20
DE60232171D1 (de) 2009-06-10
EP1446379A1 (fr) 2004-08-18
KR20090045421A (ko) 2009-05-07
JP2005509024A (ja) 2005-04-07
NO20041817L (no) 2004-05-04
MXPA04004505A (es) 2004-09-10
PL371933A1 (en) 2005-07-11
CA2466962A1 (fr) 2003-05-22
US7553971B2 (en) 2009-06-30
JP2009167199A (ja) 2009-07-30
ATE430124T1 (de) 2009-05-15
HUP0401876A2 (hu) 2004-12-28

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