US 7,342,025 B2
Substituted C-imidazo[1,2-a]pyridin-3-yl-methylamines
Hagen-Heinrich Hennies, Simmerath (Germany); Corinna Sundermann, Aachen (Germany); Bernd Sundermann, Aachen (Germany); and Stefan Oberboersch, Aachen (Germany)
Assigned to Gruenenthal GmbH, Aachen (Germany)
Filed on Apr. 07, 2005, as Appl. No. 11/100,535.
Application 11/100535 is a continuation of application No. PCT/EP03/011011, filed on Oct. 06, 2003.
Claims priority of application No. 102 46 890 (DE), filed on Oct. 08, 2002.
Prior Publication US 2005/0239822 A1, Oct. 27, 2005
This patent is subject to a terminal disclaimer.
Int. Cl. A01N 43/42 (2006.01); A61K 31/44 (2006.01); C07D 471/02 (2006.01); C07D 491/02 (2006.01); C07D 498/02 (2006.01)
U.S. Cl. 514—300  [546/121] 14 Claims
 
1. A substituted C-imidazo[1,2-a]pyridin-3-yl-methylamine compound corresponding to formula I

OG Complex Work Unit Drawing
wherein
R1 represents OH, SH, NH2, NHCH3, N(CH3)2, CH3, CH2Cl, CH2F, CHF2, CF3, OCH3, OCH2Cl, OCH2F, OCHF2, OCF3, C2H5, CHClCH3, CH2CH2Cl, CHFCH3, CH2CH2F, CH2CHF2, CH2CF3, OC2H5, COOH, CH2OH, CHOHCH3 or CH2CH2OH,
R2 represents H or CH3,
R3 represents H;
R4 represents H; or
an alkyl radical selected from the group consisting of methyl, ethyl, 1-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-dimethylethyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl and dodecyl; wherein said alkyl radical is unsubstituted or mono- or polysubstituted by a substituent selected from the group consisting of F, Cl, Br, I, NH2, SH and OH; or
a cyclic radical selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclopentenyl, cyclohexenyl, cycloheptenyl and cyclooctenyl, wherein said cyclic radical is unsubstituted or mono- or polysubstituted by a substituent selected from the group consisting of methyl, ethyl, n-propyl, i-propyl, CF3, methoxy and ethoxy; or
a radical corresponding to formula II

OG Complex Work Unit Drawing
 wherein n represents a number from 0 to 6,
m represents a number from 0 to 6,
1≤m+n ≤6
X represents O, S, SO, SO2 or NR7, and
each R independently represents H, F, Br, I, Cl, OH, SH, NH2, NO2, CH3, C2H5, OCH3, OC2H5, or OCF3;
R5 represents H; an alkyl radical selected from the group consisting of methyl, ethyl, 1-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 and hexyl, wherein said alkyl radical is unsubstituted or mono- or polysubstituted by a substituent selected from the group consisting of F, Cl, Br, I, NH2, SH and OH; or a cyclic radical selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclopentenyl, cyclohexenyl, cycloheptenyl and cyclooctenyl, wherein said cyclic radical is unsubstituted or mono- or polysubstituted by a substituent selected from the group consisting of methyl, ethyl, n-propyl, i-propyl, CF3, methoxy and ethoxy;
R6 represents H; an alkyl radical selected from the group consisting of methyl, ethyl, 1-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 and hexyl; wherein said alkyl radical is unsubstituted or mono- or polysubstituted by a substituent selected from the group consisting of F, Cl, Br, I, NH2, SH and OH; or a cyclic radical selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclopentenyl, cyclohexenyl, cycloheptenyl and cyclooctenyl, wherein said cyclic radical is unsubstituted or mono- or polysubstituted by a substituent selected from the group consisting of methyl, ethyl, n-propyl, i-propyl, CF3, methoxy and ethoxy; or a radical corresponding to formula IIa

OG Complex Work Unit Drawing
or the radicals R5 and R6 together form a ring and denote CH2CH2OCH2CH2, CH2CH2NR11CH2CH2 or (CH2)3-6,
R7 represents H; or an alkyl radical selected from the group consisting of methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1,1-dimethylethyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl and hexyl; or a cyclic radical selected from the group consisting of cyclopropyl, 2-methylcyclopropyl, cyclopropylmethyl, cyclobutyl, 2-methylcyclobutyl, 3-methylcyclobutyl, cyclobutylmethyl, cyclopentyl, cyclohexyl, and cyclooctyl; or an acyl radical C(O)R8 or a sulfonyl radical S(O2)R9,
R8 represents H; or an unsubstituted alkyl radical selected from the group consisting of methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1,1-dimethylethyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, hexyl, and 1-methylpentyl; or an aryl radical selected from the group consisting of phenyl, 3-hydroxyphenyl, 3-methoxyphenyl, 2,3-dihydroxyphenyl, 2,3-dimethoxyphenyl and 1-naphthyl;
R9 represents H; or an unsubstituted alkyl radical selected from the group consisting of methyl, ethyl, propyl, methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1,1-dimethylethyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, hexyl, and 1-methylpentyl; or an aryl radical selected from the group consisting of phenyl, 3-hydroxyphenyl, 3-methoxyphenyl, 2,3-dihydroxyphenyl, 2,3-dimethoxyphenyl and 1-naphthyl;
R11represents H; or an unsubstituted alkyl radical selected from the group consisting of methyl, ethyl, propyl, I-methylethyl, butyl, I-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, hexyl, and 1-methylpentyl; or an unsubstituted cycloalkyl radical selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclopentenyl, cyclohexenyl, cycloheptenyl and cyclooctenyl; or an aryl radical selected from the group consisting of phenyl, 3-hydroxyphenyl, 3-methoxyphenyl, 2,3-dihydroxyphenyl, 2,3-dimethoxyphenyl and 1-naphthyl; or an unsubstituted heteroaryl radical selected from the group consisting of pyrrolyl, furyl, thienyl, pyrazolyl, imidazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, pyranyl, indolyl, indazolyl, purinyl, pyrimidinyl, indolizinyl, quinolinyl, isoquinolinyl, quinazolinyl, carbazolyl, phenazinyl and phenothiazinyl; or an aryl radical which is bonded via C1-3-alkylene and is selected from the group consisting of phenyl, 3-hydroxyphenyl, 3-methoxyphenyl, 2,3-dihydroxyphenyl, 2,3-dimethoxyphenyl and 1-naphthyl; or an unsubstituted heteroaryl radical which is bonded via C1,3-alkylene and is selected from the group consisting of pyrrolyl, furyl, thienyl, pyrazolyl, imidazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, pyranyl, indolyl, indazolyl, purinyl, pyrimidinyl, indolizinyl, quinolinyl, isoquinolinyl, quinazolinyl, carbazolyl, phenazinyl and phenothiazinyl; or an acyl radical C(O)R12; or a sulfonyl radical S(O2)R13;
R12 represents H; or an unsubstituted alkyl radical selected from the group consisting of methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, hexyl, and 1-methylpentyl; or an aryl radical selected from the group consisting of phenyl, 3-hydroxyphenyl, 3-methoxyphenyl, 2,3-dihydroxyphenyl, 2,3-dimethoxyphenyl and 1-naphthyl;
R13 represents H; an unsubstituted alkyl radical selected from the group consisting of methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, hexyl, and 1-methylpentyl; or an aryl radical selected from the group consisting of phenyl, 3-hydroxyphenyl, 3-methoxyphenyl, 2,3-dihydroxyphenyl, 2,3-dimethoxyphenyl and 1-naphthyl; and
R14 represents H, F, Br, I, Cl, OH, SH, NH2, NO2, CH3, C2H5, OCH3, OC2H5, or OCF3;
or a pharmaceutically acceptable salt thereof,
with the proviso that the following compounds:

OG Complex Work Unit Drawing
are excluded.