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SUBSTITUTED 3-AMINO-4 -HYDROXY PYRROLIDINES COMPOUNDS, THEIR PREPARATION AND USE AS MEDICAMENTS

  • US 20100168093A1
  • Filed: 04/30/2007
  • Published: 07/01/2010
  • Est. Priority Date: 04/28/2006
  • Status: Abandoned Application
First Claim
Patent Images

1. Substituted pyrrolidine compounds of general formula (I), wherein R1 represents a hydrogen atom, an unbranched or branched, saturated, optionally at least mono-substituted C1-6-aliphatic radical;

  • a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloalkyl group, which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring system;

    a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing alkyl-cycloalkyl group in which the cycloalkyl group may be optionally at least mono-substituted;

    an optionally at least mono-substituted aryl group which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring system;

    an optionally at least mono-substituted heteroaryl group which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring system;

    a branched or unbranched, optionally at least mono-substituted alkyl-aryl group in which the aryl group may be optionally at least mono-substituted and/or condensed with a mono- or polycyclic ring system;

    a branched or unbranched, optionally at least mono-substituted alkyl-heteroaryl group in which the heteroaryl group may be optionally at least mono-substituted and/or condensed with a mono- or polycyclic ring system;

    an optionally at least mono-substituted benzhydryl group;

    a (C═

    O)—

    R5 group;

    a group;

    a (SO2)—

    R6 group;

    or a (C═

    O)—

    NR7R7a group;

    R2 represents a hydrogen atom;

    a substituted or unsubstituted aliphatic group;

    a (C═

    O)—

    R8 group;

    a benzyl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH2, SH, OH;

    R3 and R4, equal or different, represent a hydrogen atom;

    an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical;

    a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloalkyl group, which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring system;

    a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing alkyl-cycloalkyl group in which the cycloalkyl group may be optionally at least mono-substituted;

    an optionally at least mono-substituted aryl group which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring system;

    an optionally at least mono-substituted heteroaryl group which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring system;

    a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted alkyl-aryl group in which the aryl group may be optionally at least mono-substituted and/or condensed with a mono- or polycyclic ring system;

    a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted alkyl-heteroaryl group in which the heteroaryl group may be optionally at least mono-substituted and/or condensed with a mono- or polycyclic ring system;

    with the condition (proviso) that R3 and R4 may not at the same time represent a hydrogen atom;

    or R3 and R4 together with their bridging nitrogen atom form1) a saturated or unsaturated ring system A, comprising 1 to 3 optionally condensed rings, in which additionally at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH2, SH, OH, CF3, a C1-6-aliphatic group;

    a C1-6-alkyl-aryl group;

    a C1-6-alkyl-heteroaryl group;

    a C1-6-alkoxy group;

    a (C═

    O)—

    R9 group;

    a (C═

    O)—

    OR10 group;

    a CH2-(C═

    O)—

    O—

    R11 group;

    a (SO2)—

    R11 group;

    a NH—

    R11 group;

    or a (C═

    O)—

    NR12R12a group;

    2) an A-X—

    B group,whereinA represents a saturated or unsaturated ring system comprising 1 to 3 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH2, SH, OH, CF3, a C1-6-aliphatic group;

    a C1-6-alkyl-aryl group;

    a C1-6-alkyl-heteroaryl group;

    a C1-6-alkoxy group;

    a (C═

    O)—

    R9 group;

    a (C═

    O)—

    OR10 group;

    a CH2-(C═

    O)—

    O—

    R11 group;

    a (SO2)—

    R11 group;

    a NH—

    R11 group;

    or a (C═

    O)—

    NR12R12a group;

    X represents a bond, a —

    NH—

    group, a —

    (C═

    O)—

    group, a branched or linear, optionally substituted C1-6-aliphatic chain, —

    O—

    , or a —

    SO2

    group;

    B represents a saturated or unsaturated ring system comprising 1 to 2 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH2, SH, OH, oxo, CF3, a C1-6-aliphatic group;

    a C1-6-alkyl-aryl group;

    a C1-6-alkyl-heteroaryl group;

    a C1-6-alkoxy group;

    a (C═

    O)—

    R9 group;

    a (C═

    O)—

    OR10 group;

    a CH2-(C═

    O)—

    O—

    R11 group;

    a (SO2)—

    R11 group;

    a NH—

    R11 group;

    or a (C═

    O)—

    NR12R12a group;

    3) an A-X—

    B—

    Y—

    C group,whereinA represents a saturated or unsaturated ring system comprising 1 to 3 optionally condensed rings, in which additionally at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH2, SH, OH, CF3, a C1-6-aliphatic group;

    a C1-6-alkyl-aryl group;

    a C1-6-alkyl-heteroaryl group;

    a C1-6-alkoxy group;

    a (C═

    O)—

    R9 group;

    a (C═

    O)—

    OR10 group;

    a CH2-(C═

    O)—

    O—

    R11 group;

    a (SO2)—

    R11 group;

    a NH—

    R11 group;

    or a (C═

    O)—

    NR12R12a group;

    X represents a bond, a —

    NH—

    group, a —

    (C═

    O)—

    group, a branched or linear, optionally substituted C1-6-aliphatic chain, —

    O—

    , or a —

    SO2

    group;

    B represents a saturated or unsaturated ring system comprising 1 to 2 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH2, SH, OH, oxo, CF3, a C1-6-aliphatic group;

    a C1-6-alkyl-aryl group;

    a C1-6-alkyl-heteroaryl group;

    a C1-6-alkoxy group;

    a (C═

    O)—

    R9 group;

    a (C═

    O)—

    OR10 group;

    a CH2-(C═

    O)—

    O—

    R11 group;

    a (SO2)—

    R11 group;

    a NH—

    R11 group;

    or a (C═

    O)—

    NR12R12a group;

    Y represents a bond, a —

    NH—

    group, a —

    (C═

    O)—

    group, a branched or linear, optionally substituted C1-6-aliphatic chain, —

    O—

    , or a —

    SO2

    group;

    C represents a saturated or unsaturated ring system comprising 1 to 2 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N1 S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH2, SH, OH, oxo, CF3, a C1-6-aliphatic group;

    a C1-6-alkyl-aryl group;

    a C1-6-alkyl-heteroaryl group;

    a C1-6-alkoxy group;

    a (C═

    O)—

    R9 group;

    a (C═

    O)—

    OR10 group;

    a CH2-(C═

    O)—

    O—

    R11 group;

    a (SO2)—

    R11 group;

    a NH—

    R11 group;

    or a (C═

    O)—

    NR12R12a group;

    R5 and R6 represent a hydrogen atom, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical;

    a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloalkyl group, which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring system;

    a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing alkyl-cycloalkyl group;

    an optionally at least mono-substituted aryl group which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring system;

    an optionally at least mono-substituted heteroaryl group which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring system;

    a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted alkyl-aryl group in which the aryl group may be condensed with a mono- or polycyclic ring system;

    a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted alkyl-heteroaryl group in which the heteroaryl group may be condensed with a mono- or polycyclic ring system;

    R7 and R7a, identical or different, represent a hydrogen atom, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical;

    a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloalkyl group, which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring system;

    a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing alkyl-cycloalkyl group;

    an optionally at least mono-substituted aryl group which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring system;

    an optionally at least mono-substituted heteroaryl group which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring system;

    a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted alkyl-aryl group in which the aryl group may be condensed with a mono- or polycyclic ring system;

    a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted alkyl-heteroaryl group in which the heteroaryl group may be condensed with a mono- or polycyclic ring system;

    R8 represents a hydrogen atom;

    a branched or unbranched, saturated or unsaturated, unsubstituted aliphatic group;

    R9, R10 and R11 represent a hydrogen atom, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical;

    a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing alkyl-cycloalkyl group;

    a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted alkyl-aryl group in which the aryl group may be condensed with a mono- or polycyclic ring system;

    a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted alkyl-heteroaryl group in which the heteroaryl group may be condensed with a mono- or polycyclic ring system;

    R12 and R12a, identical or different, represent a hydrogen atom, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical;

    a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing alkyl-cycloalkyl group;

    a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted alkyl-aryl group in which the aryl group may be condensed with a mono- or polycyclic ring system;

    a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted alkyl-heteroaryl group in which the heteroaryl group may be condensed with a mono- or polycyclic ring system;

    with the provisos that if R2 represents a hydrogen atom;

    and R1 represents a hydrogen atom or a condensed aryl group;

    R3 and R4 may not form together with their bridging nitrogen atom a triazole group;

    if R2 represents a hydrogen atom;

    and R1 represents a hydrogen atom;

    a substituted C1-2 alkyl group;

    a condensed aryl group;

    a benzyl group;

    R3 and R4 may not form together with their bridging nitrogen atom a substituted, unsaturated, condensed ring system containing at least 4 nitrogen atoms as ring members;

    an unsaturated, (C═

    O)-substituted, uncondensed, 6-membered ring system in which one additional carbon atom is replaced by nitrogen. if R2 represents a hydrogen atom;

    and R3 and R4 form together with their bridging nitrogen atom a pyrrolidine ring, a piperidine ring, a piperazine ring or a morpholine ring;

    R1 may not represent a hydrogen atom;

    a methyl group;

    an unsaturated tert-butyl group;

    a (C═

    O)-substituted alkyl-heteroaryl group;

    if R2 represents a hydrogen atom;

    and R1 does not represent a benzyl group;

    and either R3 or R4 represents a hydrogen atom;

    either R3 or R4 may not represent a substituted alkyl-heteroaryl group;

    an alkyl-aryl group;

    a substituted heteroaryl group;

    an unsubstituted methyl group;

    a substituted alkyl group;

    an aryl group;

    a cyclohexyl group;

    an alkyl-cycloalkyl group wherein the cycloalkyl group contains at least one heteroatom;

    if R2 represents a hydrogen atom;

    and R1 represents an alkyl group;

    and either R3 or R4 represents a hydrogen atom;

    the other of R3 or R4 may not represent a substituted or unsubstituted C1-2 alkyl group;

    a branched C1-4 alkyl group;

    a substituted or unsubstituted C3-6 cycloalkyl group in which optionally at least one carbon atom is optionally replaced by N, S or O;

    a cycloheptyl group;

    if R2 represents a hydrogen atom;

    and R1 represents an alkyl group;

    either R3 or R4 may not represent a cyclohexyl group while the other represents at the same time an alkyl-aryl group;

    or either R3 or R4 may not represent an alkyl group while the other represents at the same time an alkyl-aryl group;

    if R2 represents a hydrogen atom;

    and R1 represents a benzhydryl group;

    and either R3 or R4 represents a hydrogen atom;

    either R3 or R4 may not represent a (C═

    O)-substituted alkyl-aryl group;

    a (C═

    O)-substituted aryl group;

    if R2 represents a hydrogen atom;

    and R1 represents benzyl;

    and either R3 or R4 represents a hydrogen atom;

    the other of R3 or R4 may not represent a substituted or unsubstituted C1-2 alkyl group;

    an unsubstituted benzyl group;

    a C3-8 substituted alkyl group;

    a substituted alkyl-aryl group;

    or R3 or R4, together with their bridging nitrogen atom may not form a tetrahydropyrimidine ring;

    a triazolo pyrimidine ring;

    if R2 represents a benzyl group;

    and either R3 or R4 represents a hydrogen atom either R3 or R4 may not represent a (C═

    O)-substituted alkyl-aryl group;

    if R2 represents a C1-3 alkyl group;

    and either R3 or R4 represents a hydrogen atom either R3 or R4 may not represent an unsubstituted C1-2 alkyl group;

    a substituted alkyl group;

    a substituted or unsubstituted aryl group;

    a substituted heteroaryl group;

    a (C═

    O)-substituted alkyl-aryl group;

    optionally in form of one of the stereoisomers, preferably enantiomers or diastereomers, a racemate or in form of a mixture of at least two of the stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a corresponding salt thereof, or a corresponding solvate thereof.

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