US 7,345,055 B2
Substituted C-imidazo [1,2-α] pyridin-3-yl-methylamines
Stefan Oberboersch, Aachen (Germany); Bernd Sundermann, Aachen (Germany); Corinna Sundermann, Aachen (Germany); and Hagen-Heinrich Hennies, Simmerath (Germany)
Assigned to Gruenenthal GmbH, Aachen (Germany)
Filed on Apr. 08, 2005, as Appl. No. 11/101,471.
Application 11/101471 is a continuation of application No. PCT/EP03/11079, filed on Oct. 07, 2003.
Claims priority of application No. 102 47 269 (DE), filed on Oct. 10, 2002.
Prior Publication US 2005/0239823 A1, Oct. 27, 2005
This patent is subject to a terminal disclaimer.
Int. Cl. A61K 31/44 (2006.01); C07D 471/02 (2006.01); C07D 491/02 (2006.01); C07D 498/02 (2006.01); C07D 513/02 (2006.01)
U.S. Cl. 514—300  [546/121] 18 Claims
 
1. A substituted C-imidazo[1,2-α]pyridin-3-yl-methylamine compound corresponding to formula I,

OG Complex Work Unit Drawing
wherein,
R1 denotes OH, SH, NH2, NHCH3, N(CH3)2, CH3, CH2Cl, CH2F, CHF2, CF3, OCH3, OCH2Cl, OCH2F, OCHF2, OCF3, SCH3, SCF3, C2H5, CHClCH3, CH2CH2Cl, CHFCH3, CH2CH2F, CH2CHF2, CH2CF3, OC2H5, COOH, CH2OH, CHOHCH3, CH2CH2OH, CN, NO2, F, Br, I or Cl,
R2 denotes H or CH3,
R3 denotes H; C1-6-alkyl, singly or multiply substituted or unsubstituted, saturated or unsaturated, branched or unbranched; methyl, ethyl, methylethyl, 1,1-dimethylethyl, propyl, 2-methylpropyl, 1-methylpropyl, 1-ethylpropyl, butyl, i-butyl, n-butyl, tert.-butyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylbutyl, pentyl, 2-methylpentyl, 3-methylpentyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl or hexyl, in each case singly or multiply substituted or unsubstituted, branched or unbranched, or in each case optionally singly or multiply substituted or unsubstituted, branched or unbranched; C3-8-cycloalkyl, in each case singly or multiply substituted or unsubstituted, singly unsaturated or saturated; cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, 2-methylcyclopropyl, cyclopropylmethyl, 2-methylcyclobutyl, 3-methylcyclobutyl, cyclobutylmethyl, in each case substituted or unsubstituted; or aryl or heteroaryl, in each case substituted or unsubstituted; or COOR10,
R4 denotes H; C1-12-alkyl, singly or multiply substituted with F, Cl, Br, I, NH2, SH, or OH or unsubstituted, saturated or unsaturated, branched or unbranched; methyl, ethyl, methylethyl, 1,1-dimethylethyl, propyl, 2-methylpropyl, 1-methylpropyl, 1-ethylpropyl, butyl, i-butyl, n-butyl, tert.-butyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylbutyl, pentyl, 2-methylpentyl, 3-methylpentyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl or hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, in each case singly or multiply substituted with F, Cl, Br, I, NH2, SH, or OH or unsubstituted, branched or unbranched; C3-8-cycloalkyl, in each case singly or multiply substituted with F, Cl, Br, I, NH2, SH, or OH or unsubstituted, singly unsaturated or saturated; cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, 2-methylcyclopropyl, cyclopropylmethyl, 2-methylcyclobutyl, 3-methylcyclobutyl, cyclobutylmethyl, in each case substituted with F, Cl, Br, I, NH2, SH, or OH or unsubstituted; or a radical according to formula II,

OG Complex Work Unit Drawing
wherein, in each case,
n denotes a number between 0 and 6,
m denotes a number between 0 and 6, and 1≤m+n≤6,
X denotes O, S, SO, SO2 or NR7,
R independently of one another denotes H, F, Br, I, Cl, OH, SH, NH2, NO2, CH3, C2H5, OCH3, OC2H5, OCF3,
R5 denotes H; C1-6-alkyl, singly or multiply substituted with F, Cl, Br, I, NH2, SH, or OH or unsubstituted, saturated or unsaturated, branched or unbranched; methyl, ethyl, methylethyl, 1,1-dimethylethyl, propyl, 2-methylpropyl, 1-methylpropyl, 1-ethylpropyl, butyl, i-butyl, n-butyl, tert.-butyl, 1-methylbutyl, 2-methylbutyl, 3-ethylbutyl, 2,2-dimethylbutyl, pentyl, 2-methylpentyl, 3-methylpentyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl or hexyl, in each case singly or multiply substituted with F, Cl, Br, I, NH2, SH, or OH or unsubstituted, branched or unbranched, or C3-8-cycloalkyl, in each case optionally singly or multiply substituted with F, Cl, Br, I, NH2, SH, or OH or unsubstituted, singly unsaturated or saturated; cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, 2-methylcyclopropyl, cyclopropylmethyl, 2-methylcyclobutyl, 3-methylcyclobutyl, cyclobutylmethyl, in each case substituted with F, Cl, Br, I, NH2, SH, or OH or unsubstituted;
R6 denotes H; C1-6-alkyl, singly or multiply substituted with F, Cl, Br, I, NH2, SH, or OH or unsubstituted, saturated or unsaturated, branched or unbranched; methyl, ethyl, methylethyl, 1,1-dimethylethyl, propyl, 2-methylpropyl, 1-methylpropyl, 1-ethylpropyl, butyl, i-butyl, n-butyl, tert.-butyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylbutyl, pentyl, 2-methylpentyl, 3-methylpentyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl or hexyl, in each case singly or multiply substituted with F, Cl, Br, I, NH2, SH, or OH or unsubstituted, branched or unbranched, or unbranched, or C3-8-cycloalkyl, in each case singly or multiply substituted with F, Cl, Br, I, NH2, SH, or OH or unsubstituted, singly unsaturated or saturated; cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, 2-methylcyclopropyl, cyclopropylmethyl, 2-methylcyclobutyl, 3-methylcyclobutyl, cyclobutylmethyl, in each case substituted with F, Cl, Br, I, NH2, SH, or OH or unsubstituted; or aryl, heteroaryl, C1-4-alkyl aryl or C1-4-alkyl heteroaryl unsubstituted or singly or multiply substituted;
or the radicals R5 and R6 together form a ring and denote CH2CH2OCH2CH2, CH2CH2NR11CH2CH2 or (CH2)3-6,
R7 denotes H, C1-6-alkyl, methyl, ethyl, propyl, methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl or hexyl, C3-8-cycloalkyl, cyclopropyl, 2-methylcyclopropyl, cycloprophlmethyl, cyclobutyl, 2-methylcyclobutyl, 3-methylcyclobutyl, cyclobutylmethyl, cyclopentyl, cyclohexyl or cyclooctyl, acyl, C(O)R8, sulfonyl or S(O2)R9,
R8 denotes H, a C1-6-alkyl radical or an aryl radical,
R9 denotes H, a C1-6-alkyl radical or an aryl radical,
R10 denotes H, a C1-6-alkyl radical or an aryl radical,
R11 denotes H, C1-6-alkyl or C3-8-cycloalkyl, aryl or heteroaryl, aryl or heteroaryl bonded via C1-3-alkylene, acyl C(O)R12 or sulfonyl S(O2)R13,
R12 denotes H, a C1-6-alkyl radical or an aryl radical,
R13 denotes H, a C1-6-alkyl radical or an aryl radical,
or a salt thereof with a physiologically tolerated acid,
provided that the compounds:

OG Complex Work Unit Drawing
are excluded.