Dihydropyridine compounds for treating or preventing metabolic disorders

US 20050203119A1
Filed: 09/10/2004
Published: 09/15/2005
Est. Priority Date: 09/10/2003
Status: Abandoned Application

First Claim

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1. A compound represented by the following structural formula:

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Abstract

This invention relates to dihydropyridine compounds of formula (I): embedded image
or a pharmaceutically acceptable salt, solvate, clathrate, or prodrug thereof wherein A₂, R₁₂, R₁₃, R₁₄, R₁₅, R₁₆, R₁₇, R₁₈, R₁₉, R₂₀, R₂₁, R₂₂, and m are defined herein, and compositions comprising such compounds. The invention also relates to methods of preventing or treating metabolic disorders, such as diabetes mellitus, and conditions and complications associated with diabetes mellitus, comprising administering to a subject in need thereof a compound of formula (1) or a composition comprising such a compound. The invention further relates to kits comprising a compound of formula (I).

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127 Claims

1. A compound represented by the following structural formula:
- View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 68, 69, 70, 117, 118)
- - 2. The compound of claim 1, wherein R₁₅and R₁₆taken together are ═
    - O and m is 1.
  - 3. The compound of claim 2, wherein A₂is selected from the group consisting of a substituted or unsubstituted phenyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted 1-oxo-pyridyl, a substituted or unsubstituted furanyl, a substituted or unsubstituted anthracenyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted indenyl, a substituted or unsubstituted azulenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted 5,6,7,8-tetrahydronaphthyl, a substituted or unsubstituted benzo[1,3]dioxolyl, a substituted or unsubstituted thienyl, a substituted or unsubstituted pyrrolyl, a substituted or unsubstituted oxazolyl, a substituted or unsubstituted imidazolyl, a substituted or unsubstituted thiazolyl, a substituted or unsubstituted isoxazolyl, a substituted or unsubstituted quinoliny, a substituted or unsubstituted pyrazolyl, a substituted or unsubstituted isothiazolyl, a substituted or unsubstituted pyridazinyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted pyrazinyl, a substituted or imsubstituted triazinyl, a substituted or unsubstituted triazolyl, a substituted or unsubstituted thiadiazolyl, a substituted or unsubstituted quinolyl, a substituted or unsubstituted isoquniolyl, a substituted or unsubstituted indazolyl, a substituted or unsubstituted benzoxazolyl, a substituted or unsubstituted benzofuryl, a substituted or unsubstituted benzothiazolyl, a substituted or unsubstituted indolizinyl, a substituted or unsubstituted imidazopyridyl, a substituted or unsubstituted isothiazolyl, a substituted or unsubstituted tetrazolyl, a substituted or unsubstituted benzimidazolyl, a substituted or unsubstituted benzoxazolyl, a substituted or unsubstituted benzothiazolyl, a substituted or unsubstituted benzothiadiazolyl, a substituted or unsubstituted benzoxadiazolyl, a substituted or unsubstituted indolyl, a substituted or unsubstituted tetrahydroindolyl, a substituted or unsubstituted azaindolyl, a substituted or unsubstituted imidazopyridyl, a substituted or unsubstituted qunizaolinyl, a substituted or unsubstituted purinyl, a substituted or unsubstituted pyrrolo[2,3]pyrimidyl, a substituted or unsubstituted pyrazolo[3,4]pyrimidyl, a substituted or unsubstituted imidazo[1,2-a]pyridyl, or a substituted or unsubstituted benzo(b)thienyl.
  - 4. The compound of claim 3, wherein A₂is substituted with one or more substituents selected from the group consisting of an alkyl, an alkenyl, an alkynyl, an cycloalkyl, an cycloalkenyl, a heterocycloalkyl, an aryl, a heteroaryl, an aralkyl, a heteraralkyl, a haloalkyl, —
    - C(O)NR₂₈R₂₉, —
      
      NR₃₀C(O)R₃₁, a halo, —
      
      OR₃₀, cyano, nitro, a haloalkoxy, —
      
      C(O)R₃₀, —
      
      NR₂₈R₂₉, —
      
      SR₃₀, —
      
      C(O)OR₃₀, —
      
      OC(O)R₃₀, —
      
      NR₃₀C(O)NR₂₈R₂₉, —
      
      OC(O)NR₂₈R₂₉, —
      
      NR₃₀C(O)OR₃₁, —
      
      S(O)_rR₃₀, and —
      
      S(O)_pNR₂₈R₂₉, wherein;
      
      R₂₈and R₂₉, for each occurrence are, independently, H, an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted cycloalkyl, an optionally substituted cycloalkenyl, an optionally substituted heterocycloalkyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted aralkyl, or an optionally substituted heteraralkyl;
      
      or R₂₈and R₂₉taken together with the nitrogen to which they are attached is optionally substituted heterocycloalkyl or optionally substituted heteroaryl; and
      
      R₃₀and R₃₁for each occurrence are, independently, H, an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted cycloalkyl, an optionally substituted cycloalkenyl, an optionally substituted heterocycloalkyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted aralkyl, or an optionally substituted heteraralkyl.
  - 5. The compound of claim 3, wherein A₂is selected from the group consisting of a substituted or unsubstituted phenyl, a substituted or unsubstituted benzo[1,3]dioxolyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted indolyl, a substituted or unsubstituted quinolinyl, a substituted or unsubstituted 1-oxo-pyridyl, a substituted or unsubstituted pyridazinyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted pyrazinyl, a substituted or unsubstituted furanyl, a substituted or unsubstituted thienyl, a substituted or unsubstituted [1,3,5]triazinyl, a substituted or unsubstituted thiazolyl, a substituted or unsubstituted imidazolyl, a substituted or unsubstituted oxazolyl, a substituted or unsubstituted indolizinyl, a substituted or unsubstituted imidazo[1,2-a]pyridyl, a substituted or unsubstituted 2,3-dihydro-benzo[1,4]dioxinyl, and a substituted or unsubstituted naphthyl.
  - 6. The compound of claim 5, wherein A₂is substituted with one, two or three substituents selected from the group consisting of halo, nitro, —
    - NR₃₂R₃₂, lower alkyl, lower alkoxy, lower alkyl sulfanyl, lower haloalkyl, phenyl, hydroxyl, cyano, and lower alkyl sulfonyl, wherein R₃₂, for each occurrence, is —
      
      H or a lower alkyl.
  - 7. The compound of claim 2, wherein R₁₉and R₂₀are each, independently, a lower alkyl.
  - 8. The compound of claim 2, wherein R₁₃is —
    - C(O)O-(lower alkyl), —
      
      C(O)OH, cyano, —
      
      C(O)NR₃₂R₃₂, —
      
      C(O)-(lower alkyl), wherein R₃₂, for each occurrence, is —
      
      H or a lower alkyl.
  - 9. The compound of claim 2, wherein R₁₄is cyclopropyl, ethoxymethyl, 2-amino-ethoxymethyl, 2-azido-ethoxymethyl, 2-(2-hydroxy-3-phenoxy-propylamino)-ethoxymethyl, propoxymethyl, isopropoxymethyl, N-mesyl-2-aminoethoxymethyl, N-acetyl-2-aminoethoxymethyl, N-ethyl-2-aminoethoxymethyl, N-methyl-2-aminoethoxymethyl, 2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethoxymethyl, morpholin-4-yl-methyl, 2-morpholin-4-yl-ethoxymethyl, N,N-dimethylaminomethyl, carbethoxycarbonylmethoxymethyl, N-(2-hydroxyethyl)-N-methylaminomethyl, piperazin-1-yl-methyl, 2-hydroxyethoxymethyl, N,N-dimethylamino-ethoxymethyl, 4-aminobutyl, imidazol-5-yl-methoxymethyl, imidazol-4-yl-methoxymethyl, 2-imidazol-1-yl-ethoxymethyl, 3-imidazol-1-yl-propyl, 3-pyrazol-1-yl-propyl, propoxymethyl, isopropoxymethyl, methoxyethoxymethyl, pyrrol-3-yl-methoxymethyl, pyrrol-2-yl-methoxymethyl, [1,2,4]triazol-3-yl-methoxymethyl, 2H-pyrazol-3-yl-methoxymethyl, 3H-[1,2,3]triazol-4-yl-methoxymethyl, or 2-pyrrol-1-yl-ethoxymethyl.
  - 10. The compound of claim 1, wherein R₁₄is —
    - NR₃₉R₄₀or —
      
      OR₄₁, wherein;
      
      R₃₉and R40 are each, independently, an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted cycloalkyl, an optionally substituted cycloalkenyl, an optionally substituted heterocycloalkyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted aralkyl, an optionally substituted heteraralkyl, —
      
      C(O)R₄₂, —
      
      C(O)OR₄₂, —
      
      C(O)NR₄₃R₄₄, —
      
      S(O)₂R₄₂, or —
      
      S(O)R₄₂;
      
      or R₃₉and R₄₀, taken together with the nitrogen to which they are attached are an optionally substituted heterocycloalkyl or optionally substituted heteroaryl;
      
      R₄₁, is —
      
      H, an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted cycloalkyl, an optionally substituted cycloalkenyl, an optionally substituted heterocycloalkyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted aralkyl, an optionally substituted heteraralkyl, —
      
      C(O)R₄₂, —
      
      C(O)OR₄₂, —
      
      C(O)NR₄₃R₄₄, —
      
      S(O)₂R₄₂, or —
      
      S(O)R₄₂;
      
      R₄₂is —
      
      H, an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted cycloalkyl, an optionally substituted cycloalkenyl, an optionally substituted heterocycloalkyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted aralkyl, or an optionally substituted heteraralkyl; and
      
      R₄₃and R₄₄are each, independently, —
      
      H, an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted cycloalkyl, an optionally substituted cycloalkenyl, an optionally substituted heterocycloalkyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted aralkyl, or an optionally substituted heteraralkyl, or R₄₃and R₄₄taken together with the nitrogen to which they are attached are an optionally substituted heterocycloalkyl or optionally substituted heteroaryl.
  - 68. A pharmaceutical composition comprising a compound according to claim 1, 2, 11, 12, 21, 23, 25, 26, 37, 38, 47, 48, 57, 58, or 67 and a pharmaceutically acceptable carrier or vehicle.
  - 69. The pharmaceutical composition according to claim 68, further comprising a one or more additional therapeutic agents.
  - 70. The pharmaceutical composition according to claim 69, wherein the additional therapeutic agent is selected from anti-diabetic agents, anti-obesity agents, lipid lowering agents or a suitable mixture thereof.
  - 117. A kit comprising a compound according to claim 1, 2, 11, 12, 21, 23, 25, 26, 37, 38, 47, 48, 57, 58, or 67 and a device for administering the compound.
  - 118. The kit of claim 117, comprising a label or printed instructions for use of the kit.

11. A compound represented by the following structural formula:
- View Dependent Claims (12, 13, 14, 15, 16, 17, 18, 19, 20)
- - 12. The compound of claim 11, wherein Y is ═
    - O, X₄is —
      
      O—
      
      , and m is 1.
  - 13. The compound of claim 12, wherein A₂is selected from the group consisting of a substituted or unsubstituted phenyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted 1-oxo-pyridyl, a substituted or unsubstituted furanyl, a substituted or unsubstituted anthracenyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted indenyl, a substituted or unsubstituted azulenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted 5,6,7,8-tetrahydronaphthyl, a substituted or unsubstituted benzo[1,3]dioxolyl, a substituted or unsubstituted benzo[1,4]dioinyl, a substituted or unsubstituted thienyl, a substituted or unsubstituted pyrrolyl, a substituted or unsubstituted oxazolyl, a substituted or unsubstituted imidazolyl, a substituted or unsubstituted thiazolyl, a substituted or unsubstituted isoxazolyl, a substituted or unsubstituted quinolinyl, a substituted or unsubstituted pyrazolyl, a substituted or unsubstituted isothiazolyl, a substituted or unsubstituted pyridazinyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted pyrazinyl, a substituted or unsubstituted triazinyl, a substituted or unsubstituted triazolyl, a substituted or unsubstituted thiadiazolyl, a substituted or unsubstituted isoquniolinyl, a substituted or unsubstituted indazolyl, a substituted or unsubstituted benzoxazolyl, a substituted or unsubstituted benzofuranyl, a substituted or unsubstituted benzothiazolyl, a substituted or unsubstituted indolizinyl, a substituted or unsubstituted imidazopyridyl, a substituted or unsubstituted isothiazolyl, a substituted or unsubstituted tetrazolyl, a substituted or unsubstituted benzimidazolyl, a substituted or unsubstituted benzoxazolyl, a substituted or unsubstituted benzothiazolyl, a substituted or unsubstituted benzothiadiazolyl, a substituted or unsubstituted benzoxadiazolyl, a substituted or unsubstituted indolyl, a substituted or unsubstituted tetrahydroindolyl, a substituted or unsubstituted azaindolyl, a substituted or unsubstituted imidazopyridyl, a substituted or unsubstituted quinazolinyl, a substituted or unsubstituted purinyl, a substituted or unsubstituted pyrrolo[2,3]pyrimidinyl, a substituted or unsubstituted pyrazolo[3,4]pyrimidinyl, a substituted or unsubstituted imidazo[1,2-a]pyridyl, or a substituted or unsubstituted benzo(b)thienyl.
  - 14. The compound of claim 13, wherein A₂is substituted with one or more substituents selected from the group consisting of an alkyl, an alkenyl, an alkynyl, an cycloalkyl, an cycloalkenyl, a heterocycloalkyl, an aryl, a heteroaryl, an aralkyl, a heteraralkyl, a haloalkyl, —
    - C(O)NR₂₈R₂₉, —
      
      NR₃₀C(O)R₃₁, a halo, —
      
      OR₃₀, cyano, nitro, a haloalkoxy, —
      
      C(O)R₃₀, —
      
      NR₂₈R₂₉, —
      
      SR₃₀, —
      
      C(O)OR₃₀, —
      
      OC(O)R₃₀, —
      
      NR₃₀C(O)NR₂₈R₂₉, —
      
      OC(O)NR₂₈R₂₉, —
      
      NR₃₀C(O)OR₃₁, —
      
      S(O)_rR₃₀, and —
      
      S(O)_pNR₂₈R₂₉, wherein;
      
      R₂₈and R₂₉, for each occurrence are, independently, H, an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted cycloalkyl, an optionally substituted cycloalkenyl, an optionally substituted heterocycloalkyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted aralkyl, or an optionally substituted heteraralkyl;
      
      or R₂₈and R₂₉taken together with the nitrogen to which they are attached is optionally substituted heterocycloalkyl or optionally substituted heteroaryl; and
      
      R₃₀and R₃₁for each occurrence are, independently, H, an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted cycloalkyl, an optionally substituted cycloalkenyl, an optionally substituted heterocycloalkyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted aralkyl, or an optionally substituted heteraralkyl.
  - 15. The compound of claim 13, wherein A₂is selected from the group consisting of a substituted or unsubstituted phenyl, a substituted or unsubstituted benzo[1,3]dioxolyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted indolyl, a substituted or unsubstituted quinolinyl, a substituted or unsubstituted 1-oxo-pyridyl, a substituted or unsubstituted pyridazinyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted pyrazinyl, a substituted or unsubstituted furanyl, a substituted or unsubstituted thienyl, a substituted or unsubstituted [1,3,5]triazinyl, a substituted or unsubstituted thiazolyl, a substituted or unsubstituted imidazolyl, a substituted or unsubstituted oxazolyl, a substituted or unsubstituted indolizinyl, a substituted or unsubstituted imidazo[1,2-a]pyridyl, a substituted or unsubstituted 2,3-dihydro-benzo[1,4]dioxinyl, and a substituted or unsubstituted naphthyl.
  - 16. The compound of claim 15, wherein A₂is substituted with one, two or three substituents selected from the group consisting of halo, nitro, —
    - NR₃₂R₃₂, lower alkyl, lower alkoxy, lower alkyl sulfanyl, lower haloalkyl, phenyl, hydroxyl, cyano, and lower alkyl sulfonyl, wherein R₃₂, for each occurrence, is —
      
      H or a lower alkyl.
  - 17. The compound of claim 12, wherein R₁₉and R₂₀are each, independently, a lower alkyl.
  - 18. The method of claim 12, wherein R₁₃is —
    - C(O)O-(lower alkyl), —
      
      C(O)OH, cyano, —
      
      C(O)NR₃₂R₃₂, —
      
      C(O)-(lower alkyl), wherein R₃₂, for each occurrence, is —
      
      H or a lower alkyl.
  - 19. The compound of claim 12, wherein R₁₄is cyclopropyl, ethoxymethyl, 2-amino-ethoxymethyl, 2-azido-ethoxymethyl, 2-(2-hydroxy-3-phenoxy-propylamino)-ethoxymethyl, propoxymethyl, isopropoxymethyl, N-mesyl-2-aminoethoxymethyl, N-acetyl-2-aminoethoxymethyl, N-ethyl-2-aminoethoxymethyl, N-methyl-2-aminoethoxymethyl, 2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethoxymethyl, morpholin-4-yl-methyl, 2-morpholin-4-yl-ethoxymethyl, N,N-dimethylaminomethyl, carbethoxycarbonylmethoxymethyl, N-(2-hydroxyethyl)-N-methylaminomethyl, piperazin-1-yl-methyl, 2-hydroxyethoxymethyl, N,N-dimethylamino-ethoxymethyl, 4-aminobutyl, imidazol-5-yl-methoxymethyl, imidazol-4-yl-methoxymethyl, 2-imidazol-1-yl-ethoxymethyl, 3-imidazol-1-yl-propyl, 3-pyrazol-1-yl-propyl, propoxymethyl, isopropoxymethyl, methoxyethoxymethyl, pyrrol-3-yl-methoxymethyl, pyrrol-2-yl-methoxymethyl, [1,2,4]triazol-3-yl-methoxymethyl, 2H-pyrazol-3-yl-methoxymethyl, 3H-[1,2,3]triazol-4-yl-methoxymethyl, or 2-pyrrol-1-yl-ethoxymethyl.
  - 20. The compound of claim 12, wherein R₁₄is —
    - NR₃₉R₄₀or —
      
      OR₄₁, wherein;
      
      R₃₉and R₄₀are each, independently, an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted cycloalkyl, an optionally substituted cycloalkenyl, an optionally substituted heterocycloalkyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted aralkyl, an optionally substituted heteraralkyl, —
      
      C(O)R₄₂, —
      
      C(O)OR₄₂, —
      
      C(O)NR₄₃R₄₄, —
      
      S(O)₂R₄₂, or —
      
      S(O)R₄₂;
      
      or R₃₉and R₄₀, taken together with the nitrogen to which they are attached are an optionally substituted heterocycloalkyl or optionally substituted heteroaryl;
      
      R₄₁is —
      
      H, an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted cycloalkyl, an optionally substituted cycloalkenyl, an optionally substituted heterocycloalkyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted aralkyl, an optionally substituted heteraralkyl, —
      
      C(O)R₄₂, —
      
      C(O)OR₄₂, —
      
      C(O)NR₄₃R₄₄, —
      
      S(O)R₄₂, or —
      
      S(O)R₄₂;
      
      R₄₂is —
      
      H, an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted cycloalkyl, an optionally substituted cycloalkenyl, an optionally substituted heterocycloalkyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted aralkyl, or an optionally substituted heteraralkyl; and
      
      R₄₃and R₄₄are each, independently, —
      
      H, an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted cycloalkyl, an optionally substituted cycloalkenyl, an optionally substituted heterocycloalkyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted aralkyl, or an optionally substituted heteraralkyl, or R₄₃and R₄₄taken together with the nitrogen to which they are attached are an optionally substituted heterocycloalkyl or optionally substituted heteroaryl.

21. A compound represented by the following structural formula:
- View Dependent Claims (22)
- - 22. A compound according to claim 21, wherein:
    - V is NH₂or N₃;
      
      X is O or CH₂;
      
      R₁and R₂are independently H or lower alkyl;
      
      R₄is CO₂-lower alkyl;
      
      R₃, R₅, R₆and R₇are each independently H or lower alkyl;
      
      n is an integer selected from 1-5; and
      
      p is an integer selected from 1-4.

23. A compound represented by the following structural formula:
- View Dependent Claims (24)
- - 24. The compound according to claim 23, wherein Ar′
    - is an ortho-substituted or unsubstituted phenyl or pyridyl, wherein if the phenyl or pyridyl is substituted, the substituents are independently selected from the group consisting of substituted or unsubstituted lower alkyl, -halo, —
      
      CN, —
      
      N(R′
      
      ₅)(R′
      
      ₅), —
      
      OR′
      
      ₅, —
      
      C(O)R′
      
      ₅, —
      
      C(O)₂R′
      
      ₅, —
      
      OC(O)R′
      
      ₅, —
      
      NO₂, and —
      
      C(O)N(R′
      
      ₅)(R′
      
      ₅);
      
      V′
      
      is NH₂or N₃;
      
      R′
      
      ₁and R′
      
      ₂may be independently selected from H and substituted or unsubstituted lower alkyl;
      
      R′
      
      ₃is H, —
      
      C(O)R₅or substituted or unsubstituted lower alkyl;
      
      R′
      
      ₄is —
      
      CO₂-lower alkyl;
      
      each R′
      
      ₅is independently H or substituted or unsubstituted —
      
      (C₁-C₁₀) alkyl; and
      
      n is 2 or 3.

25. A compound represented by the following structural formula:
- View Dependent Claims (26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36)
- - 26. The compound of claim 25, wherein R₁₅and R₁₆together are ═
    - O and m is 1.
  - 27. The compound of claim 26, wherein A₁is a substituted or unsubstituted alkyl or a substituted or tinsubstituted cycloalkyl.
  - 28. The compound of claim 27, wherein A₁is substituted with one or more substituents selected from the group consisting of an alkyl, an alkenyl, an alkynyl, an cycloalkyl, an cycloalkenyl, a heterocycloalkyl, an aryl, a heteroaryl, an aralkyl, a heteraralkyl, a haloalkyl, —
    - C(O)NR₂₈R₂₉, —
      
      NR₃₀C(O)R₃₁, a halo, —
      
      OR₃₀, cyano, nitro, a haloalkoxy, —
      
      C(O)R₃₀, —
      
      NR₂₈R₂₉, —
      
      SR₃₀, —
      
      C(O)OR₃₀, —
      
      OC(O)R₃₀, —
      
      NR₃₀C(O)NR₂₈R₂₉, —
      
      OC(O)NR₂₈R₂₉, —
      
      NR₃₀C(O)OR₃₁, —
      
      S(O)_rR₃₀, —
      
      S(O)_rNR₂₈R₂₉, ═
      
      O, ═
      
      S, and ═
      
      N—
      
      R₃₀, wherein;
      
      R₂₈and R₂₉, for each occurrence are, independently, H, an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted cycloalkyl, an optionally substituted cycloalkenyl, an optionally substituted heterocycloalkyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted aralkyl, or an optionally substituted heteraralkyl;
      
      or R₂₈and R₂₉taken together with the nitrogen to which they are attached is optionally substituted heterocycloalkyl or optionally substituted heteroaryl; and
      
      R₃₀and R₃₁for each occurrence are, independently, H, an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted cycloalkyl, an optionally substituted cycloalkenyl, an optionally substituted heterocycloalkyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted aralkyl, or an optionally substituted heteraralkyl.
  - 29. The compound of claim 27, wherein A₁is selected from the group consisting of methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, isopropyl, sec-butyl, isobutyl, tert-butyl, isopentyl, 2-methylbutyl, 3-methylbutyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 5-methylhexyl, 2,3-dimethylbutyl, 2,3-dimethylpentyl, 2,4-dimethylpentyl, 2,3-dimethylhexyl, 2,4-dimethylhexyl, 2,5-dimethylhexyl, 2,2-dimethylpentyl, 2,2-dimethylhexyl, 3,3-dimethylpentyl, 3,3-dimethylhexyl, 4,4-dimethylhexyl, 2-ethylpentyl, 3-ethylpentyl, 2-ethylhexyl, 3-ethylhexyl, 4-ethylhexyl, 2-methyl-2-ethylpentyl, 2-methyl-3-ethylpentyl, 2-methyl-4-ethylpentyl, 2-methyl-2-ethylhexyl, 2-methyl-3-ethylhexyl, 2-methyl-4-ethylhexyl, 2,2-diethylpentyl, 3,3-diethylhexyl, 2,2-diethylhexyl, 3,3-diethylhexyl, cyclopropyl, 1-methylcyclopropyl, cyclopropylmethyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, and cyclodecyl.
  - 30. The compound of claim 29, wherein A₁is methyl, isopropyl, cyclopropyl, cyclopentyl, cyclohexyl, 1-methylcyclopropyl, or cyclopropylmethyl.
  - 31. The compound of claim 26, wherein R₁₉and R₂₀are each, independently, a lower alkyl.
  - 32. The compound of claim 26, wherein R₁₃is —
    - C(O)O-(lower alkyl), —
      
      C(O)OH, cyano, —
      
      C(O)NR₃₂R₃₂, —
      
      C(O)-(lower alkyl), wherein R₃₂, for each occurrence, is —
      
      H or a lower alkyl.
  - 33. The compound of claim 26, wherein R₁₄is cyclopropyl, ethoxymethyl, 2-amino-ethoxymethyl, 2-azido-ethoxymethyl, 2-(2-hydroxy-3-phenoxy-propylamino)-ethoxymethyl, propoxymethyl, isopropoxymethyl, N-mesyl-2-aminoethoxymethyl, N-acetyl-2-aminoethoxymethyl, N-ethyl-2-aminoethoxymethyl, N-methyl-2-aminoethoxymethyl, 2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethoxymethyl, morpholin-4-yl-methyl, 2-morpholin-4-yl-ethoxymethyl, N,N-dimethylaminomethyl, carbethoxycarbonylmethoxymethyl, N-(2-hydroxyethyl)-N-methylaminomethyl, piperazin-1-yl-methyl, 2-hydroxyethoxymethyl, N,N-dimethylamino-ethoxymethyl, 4-aminobutyl, imidazol-5-yl-methoxymethyl, imidazol-4-yl-methoxymethyl, 2-imidazol-1-yl-ethoxymethyl, 3-imidazol-1-yl-propyl, 3-pyrazol-1-yl-propyl, propoxymethyl, isopropoxymethyl, methoxyethoxymethyl, pyrrol-3-yl-methoxymethyl, pyrrol-2-yl-methoxymethyl, [1,2,4]triazol-3-yl-methoxymethyl, 2H-pyrazol-3-yl-methoxymethyl, 3H-[1,2,3]triazol-4-yl-methoxymethyl, or 2-pyrrol-1-yl-ethoxymethyl.
  - 34. The compound of claim 26, wherein R₁₄is —
    - NR₃₉R₄₀or —
      
      OR₄₁, wherein;
      
      R₃₉and R₄₀are each, independently, an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted cycloalkyl, an optionally substituted cycloalkenyl, an optionally substituted heterocycloalkyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted aralkyl, an optionally substituted heteraralkyl, —
      
      C(O)R₄₂, —
      
      C(O)OR₄₂, —
      
      C(O)NR₄₃R₄₄, —
      
      S(O)₂R₄₂, or —
      
      S(O)R₄₂;
      
      or R₃₉and R₄₀, taken together with the nitrogen to which they are attached are an optionally substituted heterocycloalkyl or optionally substituted heteroaryl;
      
      R₄₁is —
      
      H, an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted cycloalkyl, an optionally substituted cycloalkenyl, an optionally substituted heterocycloalkyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted aralkyl, an optionally substituted heteraralkyl, —
      
      C(O)R₄₂, —
      
      C(O)OR₄₂, —
      
      C(O)NR₄₃NR₄₄, —
      
      S(O)₂R₄₂, or —
      
      S(O)R₄₂;
      
      R₄₂is —
      
      H, an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted cycloalkyl, an optionally substituted cycloalkenyl, an optionally substituted heterocycloalkyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted aralkyl, or an optionally substituted heteraralkyl; and
      
      R₄₃and R₄₄are each, independently, —
      
      H, an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted cycloalkyl, an optionally substituted cycloalkenyl, an optionally substituted heterocycloalkyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted aralkyl, or an optionally substituted heteraralkyl, or R₄₃and R₄₄taken together with the nitrogen to which they are attached are an optionally substituted heterocycloalkyl or optionally substituted heteroaryl.
  - 35. The compound of claim 26, wherein X₁is —
    - O—
      
      .
  - 36. The compound of claim 26, wherein X₁is >
    - CR₁₇R₁₈.

37. A compound represented by the following structural formula:
- View Dependent Claims (38, 39, 40, 41, 42, 43, 44, 45, 46)
- - 38. The compound of claim 37, wherein R₁₅and R₁₆together are ═
    - O and m is 1.
  - 39. The compound of claim 38, wherein A₁is a substituted or unsubstituted alkyl or a substituted or unsubstituted cycloalkyl.
  - 40. The compound of claim 39, wherein A₁is substituted with one or more substituents selected from the group consisting of an alkyl, an alkenyl, an alkynyl, an cycloalkyl, an cycloalkenyl, a heterocycloalkyl, an aryl, a heteroaryl, an aralkyl, a heteraralkyl, a haloalkyl, —
    - C(O)NR₂₈R₂₉, —
      
      NR₃₀C(O)R₃₁, a halo, —
      
      OR₃₀, cyano, nitro, a haloalkoxy, —
      
      C(O)R₃₀, —
      
      NR₂₈R₂₉, —
      
      SR₃₀, —
      
      C(O)OR₃₀, —
      
      OC(O)R₃₀, —
      
      NR₃₀C(O)NR₂₈R₂₉, —
      
      OC(O)NR₂₈R₂₉, —
      
      NR₃₀C(O)OR₃₁, —
      
      S(O)_rR₃₀, —
      
      S(O)_rNR₂₈R₂₉, ═
      
      O, ═
      
      S and ═
      
      N—
      
      R₃₀, wherein;
      
      R₂₈and R₂₉, for each occurrence are, independently, H, an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted cycloalkyl, an optionally substituted cycloalkenyl, an optionally substituted heterocycloalkyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted aralkyl, or an optionally substituted heteraralkyl;
      
      or R₂₈and R₂₉taken together with the nitrogen to which they are attached is optionally substituted heterocycloalkyl or optionally substituted heteroaryl; and
      
      R₃₀and R₃₁for each occurrence are, independently, H, an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted cycloalkyl, an optionally substituted cycloalkenyl, an optionally substituted heterocycloalkyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted aralkyl, or an optionally substituted heteraralkyl.
  - 41. The compound of claim 39, wherein A₁is selected from the group consisting of methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, isopropyl, sec-butyl, isobutyl, tert-butyl, isopentyl, 2-methylbutyl, 3-methylbutyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 5-methylhexyl, 2,3-dimethylbutyl, 2,3-dimethylpentyl, 2,4-dimethylpentyl, 2,3-dimethylhexyl, 2,4-dimethylhexyl, 2,5-dimethylhexyl, 2,2-dimethylpentyl, 2,2-dimethylhexyl, 3,3-dimethylpentyl, 3,3-dimethylhexyl, 4,4-dimethylhexyl, 2-ethylpentyl, 3-ethylpentyl, 2-ethylhexyl, 3-ethylhexyl, 4-ethylhexyl, 2-methyl-2-ethylpentyl, 2-methyl-3-ethylpentyl, 2-methyl-4-ethylpentyl, 2-methyl-2-ethylhexyl, 2-methyl-3-ethylhexyl, 2-methyl-4-ethylhexyl, 2,2-diethylpentyl, 3,3-diethylhexyl, 2,2-diethylhexyl, 3,3-diethylhexyl, cyclopropyl, 1-methylcyclopropyl, cyclopropylmethyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, and cyclodecyl.
  - 42. The compound of claim 41, wherein A₁is methyl, isopropyl, cyclopropyl, cyclopentyl, cyclohexyl, 1-methylcyclopropyl, or cyclopropylmethyl.
  - 43. The compound of claim 38, wherein R₁₉and R₂₀are each, independently, a lower alkyl.
  - 44. The compound of claim 38, wherein R₁₃is —
    - C(O)O-(lower alkyl), —
      
      C(O)OH, cyano, —
      
      C(O)NR₃₂R₃₂, —
      
      C(O)-(lower alkyl), wherein R₃₂, for each occurrence, is —
      
      H or a lower alkyl.
  - 45. The compound of claim 38, wherein R₁₄is cyclopropyl, ethoxymethyl, 2-amino-ethoxymethyl, 2-azido-ethoxymethyl, 2-(2-hydroxy-3-phenoxy-propylamino)-ethoxymethyl, propoxymethyl, isopropoxymethyl, N-mesyl-2-aminoethoxymethyl, N-acetyl-2-aminoethoxymethyl, N-ethyl-2-aminoethoxymethyl, N-methyl-2-aminoethoxymethyl, 2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethoxymethyl, morpholin-4-yl-methyl, 2-morpholin-4-yl-ethoxymethyl, N,N-dimethylaminomethyl, carbethoxycarbonylmethoxymethyl, N-(2-hydroxyethyl)-N-methylarninomethyl, piperazin-1-yl-methyl, 2-hydroxyethoxymethyl, N,N-dimethylamino-ethoxymethyl, 4-aminobutyl, imidazol-5-yl-methoxymethyl, imidazol-4-yl-methoxymethyl, 2-imidazol-1-yl-ethoxymethyl, 3-imidazol-1-yl-propyl, 3-pyrazol-1-yl-propyl, propoxymethyl, isopropoxymethyl, methoxyethoxymethyl, pyrrol-3-yl-methoxymethyl, pyrrol-2-yl-methoxymethyl, [1,2,4]triazol-3-yl-methoxymethyl, 2H-pyrazol-3-yl-methoxymethyl, 3H-[1,2,3]triazol-4-yl-methoxymethyl, or 2-pyrrol-1-yl-ethoxymethyl.
  - 46. The compound of claim 38, wherein R₁₄is —
    - NR₃₉R₄₀or —
      
      OR₄₁, wherein;
      
      R₃₉and R₄₀are each, independently, an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted cycloalkyl, an optionally substituted cycloalkenyl, an optionally substituted heterocycloalkyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted aralkyl, an optionally substituted heteraralkyl, —
      
      C(O)R₄₂, —
      
      C(O)OR₄₂, —
      
      C(O)NR₄₃R₄₄, —
      
      S(O)₂R₄₂, or —
      
      S(O)R₄₂;
      
      or R₃₉and R₄₀, taken together with the nitrogen to which they are attached are an optionally substituted heterocycloalkyl or optionally substituted heteroaryl;
      
      R₄₁, is —
      
      H, an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted cycloalkyl, an optionally substituted cycloalkenyl, an optionally substituted heterocycloalkyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted aralkyl, an optionally substituted heteraralkyl, —
      
      C(O)R₄₂, —
      
      C(O)OR₄₂, —
      
      C(O)NR₄₃R₄₄, —
      
      S(O)₂R₄₂, or —
      
      S(O)R₄₂;
      
      R₄₂is —
      
      H, an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted cycloalkyl, an optionally substituted cycloalkenyl, an optionally substituted heterocycloalkyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted aralkyl, or an optionally substituted heteraralkyl; and
      
      R₄₃and R₄₄are each, independently, —
      
      H, an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted cycloalkyl, an optionally substituted cycloalkenyl, an optionally substituted heterocycloalkyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted aralkyl, or an optionally substituted heteraralkyl, or R₄₃and R₄₄taken together with the nitrogen to which they are attached are an optionally substituted heterocycloalkyl or optionally substituted heteroaryl.

47. A compound represented by the following structural formula:
- View Dependent Claims (48, 49, 50, 51, 52, 53, 54, 55)
- - 48. The compound of claim 47, wherein Y is ═
    - O, X₄is —
      
      O—
      
      , and m is 1.
  - 49. The compound of claim 48, wherein A₁is a substituted or unsubstituted alkyl or a substituted or unsubstituted cycloalkyl.
  - 50. The compound of claim 49, wherein A₁is substituted with one or more substituents selected from the group consisting of an alkyl, an alkenyl, an alkynyl, an cycloalkyl, an cycloalkenyl, a heterocycloalkyl, an aryl, a heteroaryl, an aralkyl, a heteraralkyl, a haloalkyl, —
    - C(O)NR₂₈R₂₉, —
      
      NR₃₀C(O)R₃₁, a halo, —
      
      OR₃₀, cyano, nitro, a haloalkoxy, —
      
      C(O)R₃₀, —
      
      NR₂₈R₂₉, —
      
      SR₃₀, —
      
      C(O)OR₃₀, —
      
      OC(O)R₃₀, —
      
      NR₃₀C(O)NR₂₈R₂₉, —
      
      OC(O)NR₂₈R₂₉, —
      
      NR₃₀C(O)OR₃₁, —
      
      S(O)_rR₃₀, —
      
      S(O)_rNR₂₈R₂₉, ═
      
      O, ═
      
      S ═
      
      N—
      
      R₃₀, wherein;
      
      R₂₈and R₂₉, for each occurrence are, independently, H, an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted cycloalkyl, an optionally substituted cycloalkenyl, an optionally substituted heterocycloalkyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted aralkyl, or an optionally substituted heteraralkyl;
      
      or R₂₈and R₂₉taken together with the nitrogen to which they are attached is optionally substituted heterocycloalkyl or optionally substituted heteroaryl; and
      
      R₃₀and R₃₁for each occurrence are, independently, H, an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted cycloalkyl, an optionally substituted cycloalkenyl, an optionally substituted heterocycloalkyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted aralkyl, or an optionally substituted heteraralkyl.
  - 51. The compound of claim 49, wherein A₁is selected from the group consisting of methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, isopropyl, sec-butyl, isobutyl, tert-butyl, isopentyl, 2-methylbutyl, 3-methylbutyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 5-methylhexyl, 2,3-dimethylbutyl, 2,3-dimethylpentyl, 2,4-dimethylpentyl, 2,3-dimethylhexyl, 2,4-dimethylhexyl, 2,5-dimethylhexyl, 2,2-dimethylpentyl, 2,2-dimethylhexyl, 3,3-dimethylpentyl, 3,3-dimethylhexyl, 4,4-dimethylhexyl, 2-ethylpentyl, 3-ethylpentyl, 2-ethylhexyl, 3-ethylhexyl, 4-ethylhexyl, 2-methyl-2-ethylpentyl, 2-methyl-3-ethylpentyl, 2-methyl-4-ethylpentyl, 2-methyl-2-ethylhexyl, 2-methyl-3-ethylhexyl, 2-methyl-4-ethylhexyl, 2,2-diethylpentyl, 3,3-diethylhexyl, 2,2-diethylhexyl, 3,3-diethylhexyl, cyclopropyl, 1-methylcyclopropyl, cyclopropylmethyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, and cyclodecyl.
  - 52. The compound of claim 51, wherein A₁is methyl, isopropyl, cyclopropyl, cyclopentyl, cyclohexyl, 1-methylcyclopropyl, or cyclopropylmethyl.
  - 53. The compound of claim 48, wherein R₁₉and R₂₀are each, independently, a lower alkyl.
  - 54. The compound of claim 48, wherein R₁₃is —
    - C(O)O-(lower alkyl), —
      
      C(O)OH, cyano, —
      
      C(O)NR₃₂R₃₂, —
      
      C(O)-(lower alkyl), wherein R₃₂, for each occurrence, is —
      
      H or a lower alkyl.
  - 55. The compound of claim 48, wherein R₁₄is cyclopropyl, ethoxymethyl, 2-amino-ethoxymethyl, 2-azido-ethoxymethyl, 2-(2-hydroxy-3-phenoxy-propylamino)-ethoxymethyl, propoxymethyl, isopropoxymethyl, N-mesyl-2-aminoethoxymethyl, N-acetyl-2-aminoethoxymethyl, N-ethyl-2-aminoethoxymethyl, N-methyl-2-aminoethoxymethyl, 2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethoxymethyl, morpholin-4-yl-methyl, 2-morpholin-4-yl-ethoxymethyl, N,N-dimethylaminomethyl, carbethoxycarbonylmethoxymethyl, N-(2-hydroxyethyl)—
    - N-methylaminomethyl, piperazin-1-yl-methyl, 2-hydroxyethoxymethyl, N,N-dimethylamino-ethoxymethyl, 4-aminobutyl, imidazol-5-yl-methoxymethyl, imidazol-4-yl-methoxymethyl, 2-imidazol-1-yl-ethoxymethyl, 3-imidazol-1-yl-propyl, 3-pyrazol-1-yl-propyl, propoxymethyl, isopropoxymethyl, methoxyethoxymethyl, pyrrol-3-yl-methoxymethyl, pyrrol-2-yl-methoxymethyl, [1,2,4]triazol-3-yl-methoxymethyl, 2H-pyrazol-3-yl-methoxymethyl, 3H-[1,2,3]triazol-4-yl-methoxymethyl, or 2-pyrrol-1-yl-ethoxymethyl.

57. A compound represented by the following structural formula:
- View Dependent Claims (56, 58, 59, 60, 61, 62, 63, 64, 65, 66)
- - 56. The compound of claim 58, wherein R₁₄is —
    - NR₃₉R₄₀or —
      
      OR₄₁, wherein;
      
      R₃₉and R₄₀are each, independently, an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted cycloalkyl, an optionally substituted cycloalkenyl, an optionally substituted heterocycloalkyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted aralkyl, an optionally substituted heteraralkyl, —
      
      C(O)R₄₂, —
      
      C(O)OR₄₂, —
      
      C(O)NR₄₃R₄₄, —
      
      S(O)₂R₄₂, or —
      
      S(O)R₄₂;
      
      or R₃₉and R₄₀, taken together with the nitrogen to which they are attached are an optionally substituted heterocycloalkyl or optionally substituted heteroaryl;
      
      R₄₁is —
      
      H, an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted cycloalkyl, an optionally substituted cycloalkenyl, an optionally substituted heterocycloalkyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted aralkyl, an optionally substituted heteraralkyl, —
      
      C(O)R₄₂, —
      
      C(O)OR₄₂, —
      
      C(O)NR₄₃R₄₄, —
      
      S(O)₂R₄₂, or —
      
      S(O)R₄₂;
      
      R₄₂is —
      
      H, an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted cycloalkyl, an optionally substituted cycloalkenyl, an optionally substituted heterocycloalkyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted aralkyl, or an optionally substituted heteraralkyl; and
      
      R₄₃and R₄₄are each, independently, —
      
      H, an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted cycloalkyl, an optionally substituted cycloalkenyl, an optionally substituted heterocycloalkyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted aralkyl, or an optionally substituted heteraralkyl, or R₄₃and R₄₄taken together with the nitrogen to which they are attached are an optionally substituted heterocycloalkyl or optionally substituted heteroaryl.
  - 58. The compound of claim 57, wherein R₁₅and R₁₆taken together are ═
    - O, X₁is >
      
      CR₁₇R₁₈, and m is 1.
  - 59. The compound of claim 58, wherein A₁is a substituted or unsubstituted alkyl or a substituted or unsubstituted cycloalkyl.
  - 60. The compound of claim 59, wherein A₁is substituted with one or more substituents selected from the group consisting of an alkyl, an alkenyl, an alkynyl, an cycloalkyl, an cycloalkenyl, a heterocycloalkyl, an aryl, a heteroaryl, an aralkyl, a heteraralkyl, a haloalkyl, —
    - C(O)NR₂₈R₂₉, —
      
      NR₃₀C(O)R₃₁, a halo, —
      
      OR₃₀, cyano, nitro, a haloalkoxy, —
      
      C(O)R₃₀, —
      
      NR₂₈R₂₉, —
      
      SR₃₀, —
      
      C(O)OR₃₀, —
      
      OC(O)R₃₀, —
      
      NR₃₀C(O)NR₂₈R₂₉, —
      
      OC(O)NR₂₈R₂₉, —
      
      NR₃₀C(O)OR₃₁, —
      
      S(O)_rR₃₀, —
      
      S(O)_rNR₂₈R₂₉, ═
      
      O, ═
      
      S ═
      
      N—
      
      R₃₀, wherein;
      
      R₂₈and R₂₉, for each occurrence are, independently, H, an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted cycloalkyl, an optionally substituted cycloalkenyl, an optionally substituted heterocycloalkyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted aralkyl, or an optionally substituted heteraralkyl;
      
      or R₂₈and R₂₉taken together with the nitrogen to which they are attached is optionally substituted heterocycloalkyl or optionally substituted heteroaryl; and
      
      R₃₀and R₃₁for each occurrence are, independently, H, an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted cycloalkyl, an optionally substituted cycloalkenyl, an optionally substituted heterocycloalkyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted aralkyl, or an optionally substituted heteraralkyl.
  - 61. The compound of claim 59, wherein A₁is selected from the group consisting of methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, isopropyl, sec-butyl, isobutyl, tert-butyl, isopentyl, 2-methylbutyl, 3-methylbutyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 5-methylhexyl, 2,3-dimethylbutyl, 2,3-dimethylpentyl, 2,4-dimethylpentyl, 2,3-dimethylhexyl, 2,4-dimethylhexyl, 2,5-dimethylhexyl, 2,2-dimethylpentyl, 2,2-dimethylhexyl, 3,3-dimethylpentyl, 3,3-dimethylhexyl, 4,4-dimethylhexyl, 2-ethylpentyl, 3-ethylpentyl, 2-ethylhexyl, 3-ethylhexyl, 4-ethylhexyl, 2-methyl-2-ethylpentyl, 2-methyl-3-ethylpentyl, 2-methyl-4-ethylpentyl, 2-methyl-2-ethylhexyl, 2-methyl-3-ethylhexyl, 2-methyl-4-ethylhexyl, 2,2-diethylpentyl, 3,3-diethylhexyl, 2,2-diethylhexyl, 3,3-diethylhexyl, cyclopropyl, 1-methylcyclopropyl, cyclopropylmethyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, and cyclodecyl.
  - 62. The compound of claim 61, wherein A₁is methyl, isopropyl, cyclopropyl, cyclopentyl, cyclohexyl, 1-methylcyclopropyl, or cyclopropylmethyl.
  - 63. The compound of claim 58, wherein R₁₉and R₂₀are each, independently, a lower alkyl.
  - 64. The compound of claim 58, wherein R₁₃is —
    - C(O)O-(lower alkyl), —
      
      C(O)OH, cyano, —
      
      C(O)NR₃₂R₃₂, —
      
      C(O)-(lower alkyl), wherein R₃₂, for each occurrence, is —
      
      H or a lower alkyl.
  - 65. The compound of claim 58, wherein R₃₇is ethoxymethyl, 2-amino-ethoxymethyl, 2-azido-ethoxymethyl, propoxymethyl, isopropoxymethyl, N-mesyl-2-aminoethoxymethyl, N-acetyl-2-aminoethoxymethyl, N-ethyl-2-aminoethoxymethyl, N-methyl-2-aminoethoxymethyl, 2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethoxymethyl, morpholin-4-yl-methyl, 2-morpholin-4-yl-ethoxymethyl, N,N-dimethylaminomethyl, carbethoxycarbonylmethoxymethyl, N-(2-hydroxyethyl)—
    - N-methylaminomethyl, piperazin-1-yl-methyl, 2-hydroxyethoxymethyl, N,N-dimethylamino-ethoxymethyl, 4-aminobutyl, imidazol-5-yl-methoxymethyl, imidazol-4-yl-methoxymethyl, 2-imidazol-1-yl-ethoxymethyl, 3-imidazol-1-yl-propyl, 3-pyrazol-1-yl-propyl, isopropoxymethyl, methoxyethoxymethyl, pyrrol-3-yl-methoxymethyl, pyrrol-2-yl-methoxymethyl, [1,2,4]triazol-3-yl-methoxymethyl, 2H-pyrazol-3-yl-methoxymethyl, 3H-[1,2,3]triazol-4-yl-methoxymethyl, or 2-pyrrol-1-yl-ethoxymethyl.
  - 66. The compound of claim 58, wherein R₃₇is —
    - NR₃₉R₄₀or —
      
      OR₄₁, wherein;
      
      R₃₉and R₄₀are each, independently, an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted cycloalkyl, an optionally substituted cycloalkenyl, an optionally substituted heterocycloalkyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted aralkyl, an optionally substituted heteraralkyl, —
      
      C(O)R₄₂, —
      
      C(O)OR₄₂, —
      
      C(O)NR₄₃R₄₄, —
      
      S(O)₂R₄₂, or —
      
      S(O)R₄₂;
      
      or R₃₉and R₄₀, taken together with the nitrogen to which they are attached are an optionally substituted heterocycloalkyl or optionally substituted heteroaryl;
      
      R₄₁is —
      
      H, an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted cycloalkyl, an optionally substituted cycloalkenyl, an optionally substituted heterocycloalkyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted aralkyl, an optionally substituted heteraralkyl, —
      
      C(O)R₄₂, —
      
      C(O)OR₄₂, —
      
      C(O)NR₄₃R₄₄, —
      
      S(O)₂R₄₂, or —
      
      S(O)R₄₂;
      
      R₄₂is —
      
      H, an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, anoptionally substituted cycloalkyl, an optionally substituted cycloalkenyl, an optionally substituted heterocycloalkyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted aralkyl, or an optionally substituted heteraralkyl;
      
      and R₄₃and R₄₄are each, independently, —
      
      H, an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted cycloalkyl, an optionally substituted cycloalkenyl, an optionally substituted heterocycloalkyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted aralkyl, or an optionally substituted heteraralkyl, or R₄₃and R₄₄taken together with the nitrogen to which they are attached are an optionally substituted heterocycloalkyl or optionally substituted heteroaryl.

67. A compound selected from the group consisting of:
- 2-(2-amino-ethoxymethyl)-4-(2-chloro-phenyl)-7,7-dimethyl-5-oxo-1,4,5,6,7,8- hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-azido-ethoxymethyl)-4-(2-chloro-phenyl)-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-amino-ethoxymethyl)-4-benzo[1,3]dioxol-5-yl-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-amino-ethoxymethyl)-4-(2-chloro-phenyl)-1,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-amino-ethoxymethyl)-4-(2-chloro-phenyl)-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester (complex with benzenesulfonic acid);
  
  2-(2-amino-ethoxymethyl)-4-(2,3-dichloro-phenyl)-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-amino-ethoxymethyl)-7,7-dimethyl-4-(3- nitro-phenyl)-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-amino-ethoxymethyl)-4-(3-amino-phenyl)-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-amino-ethoxymethyl)-7,7-dimethyl-5-oxo-4-pyridin-2-yl-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-amino-ethoxymethyl)-4-(2-chloro-phenyl)-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-amino-ethoxymethyl)-7,7-dimethyl-4-(2-nitro-phenyl)-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-amino-ethoxymethyl)-4-(2-fluoro-phenyl)-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-amino-ethoxymethyl)-4-(2-chloro-phenyl)-7-isopropyl-5-oxo-1,4,5,6,7,8-hexa-hydroquinoline-3-carboxylic acid ethyl ester;
  
  2-(2-amino-ethoxymethyl)-4-(2-chloro-phenyl)-7- methyl-5-oxo-1,4,5,6,7,8-hexa-hydroquinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-4-(4-chloro-phenyl)-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-4-(2-methoxy-phenyl)-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-4-(2-cyano-phenyl)-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  4-(2-chloro-phenyl)-2-[2-(2-hydroxy-3-phenoxy-propylamino)-ethoxymethyl]-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-amino-ethoxymethyl)-4-(2-chloro-phenyl)-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid methyl ester;
  
  2-(2-amino-ethoxymethyl)-4-(2-chloro-phenyl)-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylic acid methyl ester (complex with benzenesulfonic acid);
  
  2-(2-Amino-ethoxymethyl)-4-{5-chloro-2-[4-(2-hydroxy-3-phenoxy-propylamino)-butoxy]-phenyl }-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylic acid ethyl ester;
  
  4-(2-chloro-phenyl)-2-[2-(2-hydroxy-3-phenoxy-propylamino)-ethoxymethyl1-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid methyl ester;
  
  2-(2-Amino-ethoxymethyl)-4-(2-chloro-phenyl)-6,6-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-4-(2-fluoro-phenyl)-7-methyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-4-(2-fluoro-phenyl)-7-isopropyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-4-(2-cyano-phenyl)-7-methyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-4-(2-cyano-phenyl)-7-isopropyl-5-oxo-1,4,5,6,7,8-hexahydro-quinolone-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-4-(2-cyano-phenyl)-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-4-(3,5-dichloro-phenyl)-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-4-(3,4-dichloro-phenyl)-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-4-(2,3-dichloro-phenyl)-7-isopropyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-4-(2,3-dichloro-phenyl)-7-methyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-4-(2,6-dichloro-phenyl)-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-4-(2,5-dichloro-phenyl)-7-methyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-4-(2,4-dichloro-phenyl)-7-methyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  S-(−
  
  )-2-(2-amino-ethoxymethyl)-4-(2-chloro-phenyl)-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester (complex with benzenesulfonic acid);
  
  2-(2-Acetylamino-ethoxymethyl)-4-(2-chloro-phenyl)-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-4-(2-chloro-phenyl)-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-5-oxo-4-pyridin-3-yl-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  4-(2-chloro-phenyl)-2-(2-ethylamino-ethoxymethyl)-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-4-(2-chloro-phenyl)-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile;
  
  Benzenesulfonate2-(3-ethoxycarbonyl-7,7-dimethyl-5-oxo-4-pyridin-3-yl-1,4,5,6,7,8-hexahydro-quinolin-2-ylmethoxy)-ethyl-ammonium;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-5-oxo-4-quinolin-3-yl-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  4-(2-chloro-phenyl)-7,7-dimethyl-2-(2-methylamino-ethoxymethyl)-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-5-oxo-4-pyridin-4-yl-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-5-oxo-4-pyridin-3-yl-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-4-(4-chloro-1,2,4,5-tetradeutium-phenyl)-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-[2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-ethoxymethyll-7,7-dimethyl-5-oxo-4-pyridin-4-yl-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-[2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-ethoxymethyl]-5-oxo-4-pyridin-3-yl-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Azido-ethoxymethyl)-7,7-dimethyl-4-(3-nitro-phenyl)-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-azido-ethoxymethyl)-4-benzo[1,3]dioxol-5-yl-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-azido-ethoxymethyl)-4-(2-chloro-phenyl)-1,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-amino-ethoxymethyl)-4-(2-chloro-phenyl)-5-oxo-4,5,6,7-tetrahydro-1H-[1]pyrindine-3-carboxylic acid ethyl ester;
  
  9-(2-chloro-phenyl)-6,6-dimethyl-5,6,7,9-tetrahydro-3H,4H-furo[3,4-b]quinoline-1,8-dione;
  
  (+)-(R)-2-(2-amino-ethoxymethyl)-4-(2-chloro-phenyl)-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexah,dro-quinoline-3-carboxylic acid ethyl ester;
  
  compound with benzenesulfonic acid;
  
  (+)-(R)-2-(2-amino-ethoxymethyl)-4-(2-chloro-phenyl)-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  (−
  
  )-(S)-2-(2-amino-ethoxymethyl)-4-(2-chloro-phenyl)-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-4-(1H-indol-3-yl)-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  4-(2-chloro-phenyl)-2-ethoxycarbonylmethoxymethyl-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  4-(2-chloro-phenyl)-2-(hydroxyl-ethoxymethyl)-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  9-(2-chloro-phenyl)-4-ethyl-6,6-dimethyl-5,6,7,9-tetrahydro-3H,4H-furo[3,4b]quinoline-1,8-dione;
  
  4-(2-chloro-phenyl)-7,7-dimethyl-5-oxo-2-piperazin-1-ylmethyl-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  4-(2-chloro-phenyl)-2-{[(2-hydroxy-ethyl)-methyl-amino]-methyl}-7,7-dimethyl-5-oxo-1,4,5,6,7.8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-4-(2-hydroxy-phenyl)-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-5-oxo-4-pyridin-3-yl-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid methyl ester;
  
  2-(2-Amino-ethoxymethyl)-1,7,7-trimethyl-5-oxo-4-pyridin-3-yl-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-hydroxy-ethoxymethyl)-7,7-dimethyl-5-oxo-4-pyridin-3-yl-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Dimethylamino-ethoxymethyl)-7,7-dimethyl-5-oxo-4-pyridin-3yl-1,4,5,6,7,8,-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(4-Amino-butyl)-7,7-dimethyl-5-oxo-4-pyridin-3yl-1,4,5,6,7,8,-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-4-(2-chloro-phenyl)-7,7-dimethyl-4,6,7,8-tetrahydro-1H-quinolin-5-one;
  
  4-(2-chloro-phenyl)-2-(2-dimethylamino-ethoxymethyl)-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  (+)-(R)-2-(2-Amino-ethoxymethyl)-7,7-dimethyl-5-oxo-4-pyridin-3-yl-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  (−
  
  )-(S)-2-(2-Amino-ethoxymethyl)-7,7-dimethyl-5-oxo-4-pyridin-3-yl-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-5-oxo-4-pyridin-3-yl-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-5-oxo-4-pyridin-4-yl-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-5-oxo-4-(6-trifluoromethyl-pyridin-3-yl)-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-4-(4-chloro-pyridin-3-yl)-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-5-oxo-4-(6-trifluoromethyl-pyridin-3-yl)-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile;
  
  2-(2-Amino-ethoxymethyl)-4-(4-chloro-pyridin-3-yl)-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile;
  
  2-(2-Amino-ethoxymethyl)-4-(3-chloro-pyridin-4-yl)-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-4-(3-chloro-pyridin-4-yl)-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile 2-(2-Amino-ethoxymethyl)-7,7-dimethyl-5-oxo-4-(1-oxy-pyridin-4-yl)-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-5-oxo-4-(1-oxy-pyridin-4-yl)-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-5-oxo-4-(1-oxy-pyridin-3-yl)-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-5-oxo-4-(1-oxy-pyridin-3-yl)-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-5-oxo-4-pyridazin-4-yl-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-5-oxo-4-pyridazin-4-yl-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-5-oxo-4-pyridazin-3-yl-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-5-oxo-4-pyridazin-3-yl-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-5-oxo-4-pyrimidin-5-yl-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-5-oxo-4-pyrimidin-5-yl-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-5-oxo-4-pyrazin-2-yl-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-5-oxo-4-pyrazin-2-yl-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-5-oxo-4-pyrimidin-4-yl-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-5-oxo-4-pyrimidin-4-yl-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile;
  
  2-(2-Amino-ethoxymethyl)-4-furan-2-yl-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-4-furan-2-yl-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-5-oxo-4-thiophen-2-yl-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-5-oxo-4-thiophen-2-yl-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-5-oxo-4-[1,3,5]triazin-2-yl-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-5-oxo-4-[1,3,5]triazin-2-yl-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-5-oxo-4-thiazol-5-yl-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-5-oxo-4-thiazol-5-yl-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-5-oxo-4-thiazol-2-yl-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester 2-(2-Amino-ethoxymethyl)-7,7-dimethyl-5-oxo-4-thiazol-2-yl-1,4,5,6,78-hexahydro-quinoline-3-carbonitrile;
  
  2-(2-Amino-ethoxymethyl)-4-(1H-imidazol-2-yl)-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-4-(1H-imidazol-2-yl)-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile;
  
  2-(2-Amino-ethoxymethyl)-4-(3H-imidazol-4-yl)-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-4-(3H-imidazol-4-yl)-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-4-oxazol-5-yl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-4-oxazol-5-yl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-4-oxazol-2-yl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-4-oxazol-2-yl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile;
  
  2-(2-Amino-ethoxymethyl)-4-indolizin-6-yl-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-4-indolizin-6-yl-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile;
  
  2-(2-Amino-ethoxymethyl)-4-indolizin-7-yl-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-4-indolizin-7-yl-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile;
  
  2-(2-Amino-ethoxymethyl)-4-imidazo[1,2-a]pyridin-7-yl-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-4-imidazo[1,2-a]pyridin-7-yl-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile;
  
  2-(2-Amino-ethoxymethyl)-4-imidazo[1,5-a]pyridin-7-yl-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-4-imidazo[1,5-a]pyridin-7-yl-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile;
  
  2-(2-Amino-ethoxymethyl)-4-imidazo[1,5-a]pyridin-6-yl-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-4-imidazo[1,5-a]pyridin-6-yl-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile;
  
  2-(2-Amino-ethoxymethyl)-4-imidazo[1,2-a]pyridin-6-yl-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-4-imidazo[1,2-a]pyridin-6-yl-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-5-oxo-4-thiophen-3-yl-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-5-oxo-4-thiophen-3-yl-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile;
  
  2-(2-Amino-ethoxymethyl)-4-furan-3-yl-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-4-furan-3-yl-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-4-oxazol-4-yl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-4-oxazol-4-yl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-5-oxo-4-thiazol-4-yl-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-5-oxo-4-thiazol-4-yl-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile 2-(2-Amino-ethoxymethyl)-4-imidazo[1,5-a]pyridin-1-yl-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-4-imidazo 1,5-a]pyridin-1-yl-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile;
  
  2-(2-Amino-ethoxymethyl)-4-imidazo[1,5-a]pyridin-3-yl-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-4-imidazo[1,5-a]pyridin-3-yl-7,7-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile;
  
  2-(2-Amino-ethoxymethyl)-4-imidazo[1,2-a]pyridin-3-yl-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-4-imidazo[1,2-a]pyridin-3-yl-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-5-oxo-4-pyridin-3-yl-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid propyl ester;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-5-oxo-4-pyridin-3-yl-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid amide;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-5-oxo-4-pyridin-3-yl-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid methylamide;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-5-oxo-4-pyridin-3-yl-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethylamide;
  
  3-Acetyl-2-(2-amino-ethoxymethyl)-7,7-dimethyl-4-pyridin-3-yl-4,6,7,8-tetrahydro-1H-quinolin-5-one;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-3-propionyl-4-pyridin-3-yl-4,6,7,8-tetrahydro-1H-quinolin-5-one;
  
  2-(2-Amino-ethoxymethyl)-3-butyryl-7,7-dimethyl-4-pyridin-3-yl-4,6,7,8-tetrahydro-1 H-quinolin-5-one;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-3-(5-methyl-oxazol-2-yl)-4-pyridin-3-yl-4,6,7,8-tetrahydro-1 H-quinolin-5-one;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-3-(3-methyl-[1,2,4]oxadiazol-5-yl)-4-pyridin-3-yl-4,6,7,8-tetrahydro-1H-quinolin-5-one;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-3-(5-methyl-[1,2,4]oxadiazol-3-yl)-4-pyridin-3-yl-4,6,7,8-tetrahydro-1H-quinolin-5-one;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-3-oxazol-2-yl-4-pyridin-3-yl-4,6,7,8-tetrahydro-1H-quinolin-5-one;
  
  2-(3H-Imidazol-4-ylmethoxymethyl)-7,7-dimethyl-5-oxo-4-pyridin-3-yl-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(1H-Imidazol-2-ylmethoxymethyl)-7,7-dimethyl-5-oxo-4-pyridin-3-yl-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(1H-Imidazol701-4-ylmethoxymethyl)-7,7-dimethyl-5-oxo-4-pyridin-3-yl-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  7,7-Dimethyl-5-oxo-4-pyridin-3-yl-2-(1H-pyrrol-3-ylmethoxymethyl)-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  7,7-Dimethyl-5-oxo-4-pyridin-3-yl-2-(1H-pyrrol-2-ylmethoxymethyl)-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  7,7-Dimethyl-5-oxo-4-pyridin-3-yl-2-(2H-[1,2,4]triazol-3-ylmethoxymethyl)-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  7,7-Dimethyl-5-oxo-2-(2H-pyrazol-3-ylmethoxymethyl)-4-pyridin-3-yl-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  7,7-Dimethyl-5-oxo-4-pyridin-3-yl-2-(3H-[1,2,3]triazol-4-ylmethoxymethyl)-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  7,7-Dimethyl-5-oxo-4-pyridin-3-yl-2-(2-pyrrol-1-yl-ethoxymethyl)-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Imidazol-1-yl-ethoxymethyl)-7,7-dimethyl-5-oxo-4-pyridin-3-yl-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(3-Imidazol-1-yl-propyl)-7,7-dimethyl-5-oxo-4-pyridin-3-yl-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  7,7-Dimethyl-5-oxo-2-(3-pyrazol-1-yl-propyl)-4-pyridin-3-yl-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  7,7-Dimethyl-2-(2-morpholin-4-yl-ethoxymethyl)-5-oxo-4-pyridin-3-yl-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-5-oxo-4-phenyl-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-5-oxo-4-(2-trifluoromethyl-phenyl)-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-5-oxo-4-(3-trifluoromethyl-phenyl)-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-4-(4-nitro-phenyl)-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-4-(3-hydroxy-phenyl)-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-4-(3-methoxy-phenyl)-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-4-(4-hydroxy-phenyl)-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-4-(4-methoxy-phenyl)-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-4-(3,5-dihydroxy-phenyl)-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-4-(3,5-dimethoxy-phenyl)-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-5-oxo-4-(3,4,5-trimethoxy-phenyl)-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-5-oxo-4-(3,4,5-trihydroxy-phenyl)-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-5-oxo-4-o-tolyl-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-5-oxo-4-m-tolyl-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-5-oxo-4-p-tolyl-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-4-naphthalen-2-yl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-4-biphenyl-4-yl-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-5-oxo-4-(2,4,6-trimethoxy-phenyl)-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-4-(4-methoxy-3-methyl-phenyl)-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-4-(2,3-dihydro-benzo [1,4]dioxin-6-yl)-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-4-(4-methanesulfonyl-phenyl)-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-4-(4-cyano-phenyl)-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-4-(4-methoxy-naphthalen-1-yl)-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-4-(2-methoxy-naphthalen-1-yl)-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester 2-(2-Amino-ethoxymethyl)-7,7-dimethyl-4-(4-methylsulfanyl-phenyl)-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-4-(2-chloro-4-fluoro-phenyl)-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-4-(2,4-dimethoxy-phenyl)-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-4-(2,5-dimethoxy-phenyl)-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-4-(2-fluoro-5-methoxy-phenyl)-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester; and
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-3-nitro-4-pyridin-3-yl-4,6,7,8-tetrahydro-1H-quinolin-5-one;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-4-(2-methoxypyrid-3-yl)-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-4-(3-chlorophenyl)-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-4-(2,4-dichlorophenyl)-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-4-(3-cyanophenyl)-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-4-(2-chlorophenyl)-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-4-(4-methylpyrid-3-yl)-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2,7,7-Trimethyl-4-(2-methoxyphenyl)-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-4-(4-methoxypyrid-3-yl)-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2,7,7-Trimethyl-4-(pyrid-3-yl)-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2,7,7-Trimethyl-4-(pyrid-3-yl)-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile;
  
  2-(2-Amino-ethyoxymethyl)-7,7-dimethyl-4-(2-methoxyphenyl)-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-4-(pyrid-3-yl)-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-4-(5-methyl-furan-2-yl)-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-Propoxymethyl-7,7-dimethyl-4-(pyrid-3-yl)-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-Ethoxymethyl-7,7-dimethyl-4-(5-methyl-furan-2-yl)-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-4-(5-chloro-6-methoxypyrid-3-yl)-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2,7,7-Trimethyl-4-(5-methyl-furan-2-yl)-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-Isopropoxymethyl-7,7-dimethyl-4-(pyrid-3-yl)-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-7,7-dimethyl-4-(6-hydroxypyrid-3-yl)-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2,7,7-Trimethyl-4-(2-methoxyphenyl)-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile;
  
  2,7,7-Trimethyl-4-(2-chlorophenyl)-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-Methoxymethyl-4-cyclopropyl-5-oxo-7,7-dimethyl-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2,7,7-Trimethyl-4-cyclopropyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid methyl ester;
  
  2,4,7,7-Tetramethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2,7,7-Trimethyl-4-cyclohexyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2,7,7-Trimethyl-4-propyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-4-propyl-5-oxo-7,7-dimethyl-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2,7,7-Trimethyl-4-cyclopentyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester 2,7,7-Trimethyl-4-cyclopropyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile;
  
  2-(Amino-ethoxymethyl)-4-cyclopentyl-5-oxo-7,7-dimethyl-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2,7,7-Trimethyl-4-(t-butyl)-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2,7,7-Trimethyl-4-(1-methyl-cyclopropyl)-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-Methyl-4-cyclopropyl-5-oxo-spiro[1,4,5,6,7,8-hexahydro-quinoline-7,1′
  
  -cyclopentane]-3-carboxylic acid ethyl ester;
  
  2-(Morpholin-4-yl-methyl)-4-cyclopropyl-5-oxo-7,7-dimethyl-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(Hydroxymethyl)-4-cyclopropyl-5-oxo-7,7-dimethyl-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile;
  
  2-[2-(Morpholin-4-yl)-ethoxymethyl]-4-cyclopropyl-5-oxo-7,7-dimethyl-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(2-Amino-ethoxymethyl)-4-trifluoromethyl-5-oxo-7,7-dimethyl-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-Trifluoromethyl-4-cyclopropyl-5-oxo-7,7-dimethyl-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2,4-Dicyclopropyl-5-oxo-7,7-dimethyl-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-Ethyl-4-cyclopropyl-5-oxo-7,7-dimethyl-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2,7,7-Trimethyl-4-(cyclopropyl-methyl)-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-(Morpholin-4-yl-methyl)-4-(isopropyl)-5-oxo-7,7-dimethyl-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  2-[2-(Morpholin-4-yl)-ethoxymethyl]-4-(isopropyl)-5-oxo-7,7-dimethyl-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester; and
  
  2-(2-Amino-ethoxymethyl)-4-cyclohexyl-5-oxo-7,7-dimethyl-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester;
  
  and pharmaceutically acceptable salts, solvates, clathrates or polymorphs thereof.

71. A method for treating or preventing a metabolic disorder in a subject, comprising administering to the subject an effective amount of a compound represented by the following structural formula:
- View Dependent Claims (76, 77, 78, 79, 80, 81, 82, 83, 95)
- - 76. The method of claim 71, 72, 73, 74, or 75, wherein R₁₅and R₁₆together are ═
    - O and m is 1.
  - 77. The method of claim 76, wherein A₂is selected from the group consisting of a substituted or unsubstituted phenyl, a substituted or unsubstituted benzo[1,3]dioxolyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted indolyl, a substituted or unsubstituted quinolinyl, a substituted or unsubstituted 1-oxo-pyridyl, a substituted or unsubstituted pyridazinyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted pyrazinyl, a substituted or unsubstituted furanyl, a substituted or unsubstituted thienyl, a substituted or unsubstituted [1,3,5]triazinyl, a substituted or unsubstituted thiazolyl, a substituted or unsubstituted imidazolyl, a substituted or unsubstituted oxazolyl, a substituted or unsubstituted indolizinyl, a substituted or unsubstituted imidazo[1,2-a]pyridyl, a substituted or unsubstituted 2,3-dihydro-benzo[1,4]dioxinyl, and a substituted or unsubstituted naphthyl.
  - 78. The method of claim 77, wherein A₂is substituted with one, two or three substituents selected from the group consisting of halo, nitro, —
    - NR₃₂R₃₂, lower alkyl, lower alkoxy, lower alkyl sulfanyl, lower haloalkyl, phenyl, hydroxyl, cyano, and lower alkyl sulfonyl, wherein R₃₂, for each occurrence, is —
      
      H or a lower alkyl.
  - 79. The method of claim 76, wherein R₁₉and R₂₀are each, independently, a lower alkyl.
  - 80. The method of claim 76, wherein R₁₃is —
    - C(O)O-(lower alkyl), —
      
      C(O)OH, cyano, —
      
      C(O)NR₃₂R₃₂, —
      
      C(O)-(lower alkyl), wherein R₃₂, for each occurrence, is —
      
      H or a lower alkyl.
  - 81. The method of claim 76, wherein R₁₄is cyclopropyl, ethoxymethyl, 2-amino-ethoxymethyl, 2-azido-ethoxymethyl, 2-(2-hydroxy-3-phenoxy-propylamino)-ethoxymethyl, propoxymethyl, isopropoxymethyl, N-mesyl-2-aminoethoxymethyl, N-acetyl-2-aminoethoxymethyl, N-ethyl-2-aminoethoxymethyl, N-methyl-2-aminoethoxymethyl, 2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethoxymethyl, morpholin-4-yl-methyl, 2-morpholin-4-yl-ethoxymethyl, N,N-dimethylaminomethyl, carbethoxycarbonylmethoxymethyl, N-(2-hydroxyethyl)-N-methylaminomethyl, piperazin-1-yl-methyl, 2-hydroxyethoxymethyl, N,N-dimethylamino-ethoxymethyl, 4-aminobutyl, imidazol-5-yl-methoxymethyl, imidazol-4-yl-methoxymethyl, 2-imidazol-1-yl-ethoxymethyl, 3-imidazol-1-yl-propyl, 3-pyrazol-1-yl-propyl, propoxymethyl, isopropoxymethyl, methoxyethoxymethyl, pyrrol-3-yl-methoxymethyl, pyrrol-2-yl-methoxymethyl, [1,2,4]triazol-3-yl-methoxymethyl, 2H-pyrazol-3-yl-methoxymethyl, 3H-[1,2,3]triazol-4-yl-methoxymethyl, or 2-pyrrol-1-yl-ethoxymethyl.
  - 82. The method of claim 76, wherein R₁₄is a lower alkyl, a lower haloalkyl, a cycloalkyl, a —
    - (C₁-C₆)alkyl-NHR₃₈, a —
      
      (C₁-C₆)alkyl-O—
      
      (C₁-C₆)alkyl-NHR₃₈, wherein R₃₈, for each occurrence is —
      
      S(O)—
      
      (C₁-C₆)alkyl, —
      
      S(O)₂—
      
      (C₁-C₆)alkyl, and —
      
      C(O)—
      
      (C₁-C₆)alkyl.
  - 83. The method of claim 76, wherein R₁₄is —
    - NR₃₉R₄₀or —
      
      OR₄₁, wherein;
      
      R₃₉and R₄₀are each, independently, an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted cycloalkyl, an optionally substituted cycloalkenyl, an optionally substituted heterocycloalkyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted aralkyl, an optionally substituted heteraralkyl, —
      
      C(O)R₄₂, —
      
      C(O)OR₄₂, —
      
      C(O)NR₄₃R₄₄, —
      
      S(O)₂R₄₂, or —
      
      S(O)R₄₂;
      
      or R₃₉and R₄₀, taken together with the nitrogen to which they are attached are an optionally substituted heterocycloalkyl or optionally substituted heteroaryl;
      
      R₄₁is —
      
      H, an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted cycloalkyl, an optionally substituted cycloalkenyl, an optionally substituted heterocycloalkyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted aralkyl, an optionally substituted heteraralkyl, —
      
      C(O)R₄₂, —
      
      C(O)OR₄₂, —
      
      C(O)NR₄₃R₄₄, —
      
      S(O)₂R₄₂, or —
      
      S(O)R₄₂;
      
      R₄₂is —
      
      H, an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted cycloalkyl, an optionally substituted cycloalkenyl, an optionally substituted heterocycloalkyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted aralkyl, or an optionally substituted heteraralkyl;
      
      and R₄₃and R₄₄are each, independently, —
      
      H, an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted cycloalkyl, an optionally substituted cycloalkenyl, an optionally substituted heterocycloalkyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted aralkyl, or an optionally substituted heteraralkyl, or R₄₃and R₄₄taken together with the nitrogen to which they are attached are an optionally substituted heterocycloalkyl or optionally substituted heteroaryl.
  - 95. The method of claim 79, wherein R₁₄is a lower alkyl, a lower haloalkyl, a cycloalkyl, a —
    - (C₁-C₆)alkyl-NHR₃₈, a —
      
      (C₁-C₆)alkyl-O—
      
      (C₁-C₆)alkyl-NHR₃₈, wherein R₃₈, for each occurrence, is —
      
      S(O)—
      
      (C₁-C₆)alkyl, —
      
      S(O)₂—
      
      (C₁-C₆)alkyl, and —
      
      C(O)—
      
      (C₁-C₆)alkyl.

72. A method for treating or preventing diabetes in a subject, comprising administering to the subject an effective amount of a compound represented by the following structural formula:

73. A method for reducing blood glucose levels in a subject, comprising administering to a subject an effective amount of a compound represented by the following structural formula:

74. A method for increasing insulin sensitivity in a subject, comprising administering to the subject an effective amount of a compound represented by the following structural formula:

75. A method for lowering triglyceride levels in a subject, comprising administering to the subject an effective amount of a compound represented by the following structural formula:

84. A method for treating or preventing a metabolic disorder in a subject, comprising administering to the subject an effective amount of a compound represented by the following structural formula:
- View Dependent Claims (89, 90, 91, 92, 93, 94, 96)
- - 89. The method of claim 84, 85, 86, 87, or 88, wherein Y is ═
    - O, X₄is —
      
      O— and
      
      m is 1.
  - 90. The method of claim 89, wherein A₂is selected from the group consisting of a substituted or unsubstituted phenyl, a substituted or unsubstituted benzo[1,3]dioxolyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted indolyl, a substituted or unsubstituted quinolinyl, a substituted or unsubstituted 1-oxo-pyridyl, a substituted or unsubstituted pyridazinyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted pyrazinyl, a substituted or unsubstituted furanyl, a substituted or unsubstituted thienyl, a substituted or unsubstituted [1,3,5]triazinyl, a substituted or unsubstituted thiazolyl, a substituted or unsubstituted imidazolyl, a substituted or unsubstituted oxazolyl, a substituted or unsubstituted indolizinyl, a substituted or unsubstituted imidazo[1,2-a]pyridyl, a substituted or unsubstituted 2,3-dihydro-benzo[1,4]dioxinyl, and a substituted or unsubstituted naphthyl.
  - 91. The method of claim 90, wherein A₂is substituted with one, two or three substituents selected from the group consisting of halo, nitro, —
    - NR₃₂R₃₂, lower alkyl, lower alkoxy, lower alkyl sulfanyl, lower haloalkyl, phenyl, hydroxyl, cyano, and lower alkyl sulfonyl, wherein R₃₂, for each occurrence, is —
      
      H or a lower alkyl.
  - 92. The method of claim 89, wherein R₁₉and R₂₀are each, independently, a lower alkyl.
  - 93. The method of claim 89, wherein R₁₃is —
    - C(O)O-(lower alkyl), —
      
      C(O)OH, cyano, —
      
      C(O)NR₃₂R₃₂, —
      
      C(O)-(lower alkyl), wherein R₃₂, for each occurrence, is —
      
      H or a lower alkyl.
  - 94. The method of claim 89, wherein R₁₄is cyclopropyl, ethoxymethyl, 2-amino-ethoxymethyl, 2-azido-ethoxymethyl, 2-(2-hydroxy-3-phenoxy-propylamino)-ethoxymethyl, propoxymethyl, isopropoxymethyl, N-mesyl-2-aminoethoxymethyl, N-acetyl-2-aminoethoxymethyl, N-ethyl-2-aminoethoxymethyl, N-methyl-2-aminoethoxymethyl, 2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethoxymethyl, morpholin-4-yl-methyl, 2-morpholin-4-yl-ethoxymethyl, N,N-dimethylaminomethyl, carbethoxycarbonylmethoxymethyl, N-(2-hydroxyethyl)—
    - N-methylaminomethyl, piperazin-1-yl-methyl, 2-hydroxyethoxymethyl, N,N-dimethylamino-ethoxymethyl, 4-aminobutyl, imidazol-5-yl-methoxymethyl, imidazol-4-yl-methoxymethyl, 2-imidazol-1-yl-ethoxymethyl, 3-imidazol-1-yl-propyl, 3-pyrazol-1-yl-propyl, propoxymethyl, isopropoxymethyl, methoxyethoxymethyl, pyrrol-3-yl-methoxymethyl, pyrrol-2-yl-methoxymethyl, [1,2,4]triazol-3-yl-methoxymethyl, 2H-pyrazol-3-yl-methoxymethyl, 3H-[1,2,3]triazol-4-yl-methoxymethyl, or 2-pyrrol-1-yl-ethoxymethyl.
  - 96. The method of claim 89, wherein R₁₄is —
    - NR₃₉R₄₀or —
      
      OR₄₁, wherein;
      
      R₃₉and R₄₀are each, independently, an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted cycloalkyl, an optionally substituted cycloalkenyl, an optionally substituted heterocycloalkyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted aralkyl, an optionally substituted heteraralkyl, —
      
      C(O)R₄₂, —
      
      C(O)OR₄₂, —
      
      C(O)NR₄₃R₄₄, —
      
      S(O)₂R₄₂, or —
      
      S(O)R₄₂;
      
      or R₃₉and R₄₀, taken together with the nitrogen to which they are attached are an optionally substituted heterocycloalkyl or optionally substituted heteroaryl;
      
      R₄₁is —
      
      H, an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted cycloalkyl, an optionally substituted cycloalkenyl, an optionally substituted heterocycloalkyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted aralkyl, an optionally substituted heteraralkyl, —
      
      C(O)R₄₂, —
      
      C(O)OR₄₂, —
      
      C(O)NR₄₃R₄₄, —
      
      S(O)₂R₄₂, or —
      
      S(O)R₄₂;
      
      R₄₂is —
      
      H, an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted cycloalkyl, an optionally substituted cycloalkenyl, an optionally substituted heterocycloalkyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted aralkyl, or an optionally substituted heteraralkyl;
      
      and R₄₃and R₄₄are each, independently, —
      
      H, an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted cycloalkyl, an optionally substituted cycloalkenyl, an optionally substituted heterocycloalkyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted aralkyl, or an optionally substituted heteraralkyl, or R₄₃and R₄₄taken together with the nitrogen to which they are attached are an optionally substituted heterocycloalkyl or optionally substituted heteroaryl.

85. A method for treating or preventing diabetes in a subject, comprising administering to the subject an effective amount of a compound represented by the following structural formula:

86. A method for reducing blood glucose levels in a subject, comprising administering to a subject an effective amount of a compound represented by the following structural formula:

87. A method for increasing insulin sensitivity in a subject, comprising administering to the subject an effective amount of a compound represented by the following structural formula:

88. A method for lowering triglyceride levels in a subject, comprising administering to the subject an effective amount of a compound represented by the following structural formula:

97. A method for treating or preventing a metabolic disorder, comprising administering to a subject in need thereof an effective amount of a compound represented by the following structural formula:
- View Dependent Claims (98)
- - 98. The method according to claim 97, wherein the disorder is diabetes mellitus, a condition associated with diabetes mellitus or complication of diabetes mellitus.

99. A method for reducing blood glucose levels in a subject in need thereof, comprising administering to the subject an effective amount of a compound represented by the following structural formula:

100. A method for increasing insulin sensitivity in a subject in need thereof, comprising administering to the subject an effective amount of a compound represented by the following structural formula:
- View Dependent Claims (102, 103, 104, 127)
- - 102. The method of claim 97, 99, 100, or 101, wherein the compound has the structure:
  - 103. The method of claim 97, 99, 100, or 101 wherein the compound has the structure:
  - 104. The method of claim 97, 99, 100, or 101, wherein the compound has the structure:
  - 127. The method of claim 71, 72, 73, 74, 75, 84, 85, 86, 87, 88, 97, 98, 99, 100, 103, 105, 106, 107, 108, 109, 119, or 120, further comprising administering one or more additional therapeutic agent selected from the group consisting of anti-diabetic agents, anti-obesity agents, lipid lowering agents, and combinations thereof.

101. A method for lowering elevated triglyceride levels in a subject in need thereof, comprising administering to the subject an effective amount of a compound represented by the following structural formula:

105. A method for treating or preventing a metabolic disorder in a subject, comprising administering to the subject an effective amount of a compound represented by the following structural formula:
- View Dependent Claims (110, 111, 112, 113, 114, 115, 116)
- - 110. The method of claim 105, 106, 107, 108, or 109, wherein R₁₅and R₁₆together are ═
    - O, X₁is >
      
      CR₁₇R₁₈, and m is 1.
  - 111. The method of claim 110, wherein A₁is methyl, isopropyl, cyclopropyl, cyclopentyl, cyclohexyl, 1-methylcyclopropyl, or cyclopropylmethyl.
  - 112. The method of claim 110, wherein R₁₉and R₂₀are each, independently, a lower alkyl.
  - 113. The method of claim 110, wherein R₁₃is —
    - C(O)O-(lower alkyl), —
      
      C(O)OH, cyano, —
      
      C(O)NR₃₂R₃₂, —
      
      C(O)-(lower alkyl), wherein R₃₂, for each occurrence, is —
      
      H or a lower alkyl.
  - 114. The method of claim 110, wherein R₁₄is cyclopropyl, ethoxymethyl, 2-amino-ethoxymethyl, 2-azido-ethoxymethyl, 2-(2-hydroxy-3-phenoxy-propylamino)-ethoxymethyl, propoxymethyl, isopropoxymethyl, N-mesyl-2-aminoethoxymethyl, N-acetyl-2-aminoethoxymethyl, N-ethyl-2-aminoethoxymethyl, N-methyl-2-aminoethoxymethyl, 2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethoxymethyl, morpholin-4-yl-methyl, 2-morpholin-4-yl-ethoxymethyl, N,N-dimethylaminomethyl, carbethoxycarbonylmethoxymethyl, N-(2-hydroxyethyl)—
    - N-methylaminomethyl, piperazin-1-yl-methyl, 2-hydroxyethoxymethyl, N,N-dimethylamino-ethoxymethyl, 4-aminobutyl, imidazol-5-yl-methoxymethyl, imidazol-4-yl-methoxymethyl, 2-imidazol-1-yl-ethoxymethyl, 3-imidazol-1-yl-propyl, 3-pyrazol-1-yl-propyl, propoxymethyl, isopropoxymethyl, methoxyethoxymethyl, pyrrol-3-yl-methoxymethyl, pyrrol-2-yl-methoxymethyl, [1,2,4]triazol-3-yl-methoxymethyl, 2H-pyrazol-3-yl-methoxymethyl, 3H-[1,2,3]triazol-4-yl-methoxymethyl, or 2-pyrrol-1-yl-ethoxymethyl.
  - 115. The method of claim 110, wherein R₁₄is a lower alkyl, a lower haloalkyl, a cycloalkyl, a —
    - (C₁-C₆)alkyl-NHR₃₈, a —
      
      (C₁-C₆)alkyl-O—
      
      (C₁-C₆)alkyl-NHR₃₈, wherein R₃₈, for each occurrence, is —
      
      S(O)—
      
      (C₁-C₆)alkyl, —
      
      S(O)₂—
      
      (C₁-C₆)alkyl, and —
      
      C(O)—
      
      (C₁-C₆)alkyl.
  - 116. The method of claim 110, wherein R₁₄is —
    - NR₃₉R₄₀or —
      
      OR₄₁, wherein;
      
      R₃₉and R₄₀are each, independently, an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted cycloalkyl, an optionally substituted cycloalkenyl, an optionally substituted heterocycloalkyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted aralkyl, an optionally substituted heteraralkyl, —
      
      C(O)R₄₂, —
      
      C(O)OR₄₂, —
      
      C(O)NR₄₃R₄₄, —
      
      S(O)₂R₄₂, or —
      
      S(O)R₄₂;
      
      or R₃₉and R₄₀, taken together with the nitrogen to which they are attached are an optionally substituted heterocycloalkyl or optionally substituted heteroaryl;
      
      R₄₁is —
      
      H, an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted cycloalkyl, an optionally substituted cycloalkenyl, an optionally substituted heterocycloalkyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted aralkyl, an optionally substituted heteraralkyl, —
      
      C(O)R₄₂, —
      
      C(O)OR₄₂, —
      
      C(O)NR₄₃R₄₄, —
      
      S(O)₂R₄₂, or —
      
      S(O)R₄₂;
      
      R₄₂is —
      
      H, an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted cycloalkyl, an optionally substituted cycloalkenyl, an optionally substituted heterocycloalkyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted aralkyl, or an optionally substituted heteraralkyl;
      
      and R₄₃and R₄₄are each, independently, —
      
      H, an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted cycloalkyl, an optionally substituted cycloalkenyl, an optionally substituted heterocycloalkyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted aralkyl, or an optionally substituted heteraralkyl, or R₄₃and R₄₄taken together with the nitrogen to which they are attached are an optionally substituted heterocycloalkyl or optionally substituted heteroaryl.

106. A method for treating or preventing diabetes in a subject, comprising administering to the subject an effective amount of a compound represented by the following structural formula:

107. A method for reducing blood glucose levels in a subject, comprising administering to a subject an effective amount of a compound represented by the following structural formula:

108. A method for increasing insulin sensitivity in a subject, comprising administering to the subject an effective amount of a compound represented by the following structural formula:

109. A method for lowering triglyceride levels in a subject, comprising administering to the subject an effective amount of a compound represented by the following structural formula:

119. A 3-substituted-1,4-dihydropyridine compound characterized by an ability to reduce elevated blood glucose levels without a significant cardiovascular effect, wherein the core scaffold of the compound is a 1,4-dihydropyridine.

120. A 4-substituted-1,4,5,6,7,8-hexahydroquinoline compound characterized by an ability to reduce elevated blood glucose levels without a significant cardiovascular effect, wherein the core scaffold of the compound is a 1,4,5,6,7,8-hexahydro-quinoline.
- View Dependent Claims (121, 122, 123, 124, 125, 126)
- - 121. The compound of claim 120, further comprising a 5-oxo substituent.
  - 122. The compound of claim 120, wherein the molecular weight of the compound is about 300 g/mol to about 500 g/mol.
  - 123. A pharmaceutical composition comprising a compound of claim 120, or a pharmaceutically acceptable salt, solvate, or hydrate thereof, and a pharmaceutically acceptable carrier, diluent or excipient.
  - 124. A method for reducing blood glucose levels in a subject in need thereof, comprising administering to the subject an effective amount of a compound of claim 120.
  - 125. A method for increasing insulin sensitivity in a subject in need thereof, comprising administering to the subject an effective amount of a compound of claim 120.
  - 126. A method for lowering elevated triglyceride levels in a subject in need thereof, comprising administering to the subject an effective amount of a compound of claim 120.

Specification

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Current Assignee
Synta Pharmaceuticals Corp. (Madrigal Pharmaceuticals, Inc.)
Original Assignee
Synta Pharmaceuticals Corp. (Madrigal Pharmaceuticals, Inc.)
Inventors
Sun, Lijun, Foley, Kevin, Wada, Yumiko, Zhang, Shijie, Li, Hao, Przewloka, Teresa, Borella, Christopher, Ono, Mitsunori, Chen, Shoujun, Koya, Keizo, Xia, Zhi-Qiang, Zhou, Dan

Application Number

US10/939,252
Publication Number

US 20050203119A1
Time in Patent Office

Days
Field of Search
US Class Current

514/300
CPC Class Codes

A61P 3/00   Drugs for disorders of the ...

A61P 3/06   Antihyperlipidemics

A61P 3/10   for hyperglycaemia, e.g. an...

C04B 35/632   Organic additives

C07D 215/54   attached in position 3

C07D 221/20   Spiro-condensed ring systems

C07D 401/04   directly linked by a ring-m...

C07D 401/12   linked by a chain containin...

C07D 401/14   containing three or more he...

C07D 405/04   directly linked by a ring-m...

C07D 491/04   Ortho-condensed systems

Dihydropyridine compounds for treating or preventing metabolic disorders

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Abstract

87 Citations

127 Claims

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Dihydropyridine compounds for treating or preventing metabolic disorders

First Claim

1 Assignment

Subscription Required

Subscription Required

0 Petitions

Subscription Required

Accused Products

Subscription Required

Abstract

87 Citations

127 Claims

Specification

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Use Cases

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