Substituted bicyclic imidazo-3-ylamine compounds

Description

CROSS-REFERENCE TO RELATED APPLICATIONS

This application is a continuation of International patent application Serial No. PCT/EP2005/054436 filed Sep. 8, 2007 which claims benefit to German patent application Serial No. 10 2004 044 884.1 filed Sep. 14, 2004, the entire disclosures of which are hereby incorporated in their entirety.

FIELD OF THE INVENTION

The present invention relates to substituted bicyclic imidazo-3-yl-amine compounds, to processes for the production thereof, to pharmaceutical formulations containing these compounds, the use of these compounds for the production of pharmaceutical formulations and related methods of treatment.

BACKGROUND OF THE INVENTION

Pain is one of the basic clinical symptoms. There is a worldwide need for effective pain treatments. The urgency of the requirement for therapeutic methods for providing tailored and targeted treatment of chronic and non-chronic pain, this being taken to mean pain treatment which is effective and satisfactory from the patient's standpoint, is also evident from the large number of scientific papers relating to applied analgesia and to basic nociception research which have appeared in recent times.

Conventional opioids, such as for example morphine, are effective in the treatment of severe to very severe pain, but they often lead to unwanted accompanying symptoms, such as for example respiratory depression, vomiting, sedation, constipation or the development of tolerance. Moreover, they are frequently insufficiently effective in the case of neuropathic pain, suffered in particular by tumour patients.

SUMMARY OF THE INVENTION

One object of the present invention was accordingly to provide novel compounds which are suitable in particular as pharmaceutical active ingredients in pharmaceutical formulations, preferably in pharmaceutical formulations for the treatment of pain.

It has now surprisingly been found that the substituted bicyclic imidazo-3-yl-amine compounds of the general formula I stated hereinafter are suitable for mGluR5 receptor regulation (mGluR5=metabotropic glutamate receptor 5) and may therefore be used in particular as pharmaceutical active ingredients in pharmaceutical formulations for the prevention and/or treatment of disorders or diseases associated with these receptors or processes.

The present invention accordingly provides substituted imidazo-3-yl-amine compounds of the general formula I,

embedded image

in which

A1 represents a nitrogen atom or a C—R1a group,

A2 represents a nitrogen atom or a C—R1b group,

A3 represents a nitrogen atom or a C—R1c group,

A4 represents a nitrogen atom or a C—R1d group,

R1a, R1b, R1c, R1d, mutually independently, in each case represent a hydrogen; a halogen; —NO2; —CN; —NH2; —NHR4; —NR5R6; —NH—C(═O)—R7; —C(═O)—R8, —C(═O)—NH2; —C(═O)—NHR9; —C(═O)—NR10R11; —C(═O)—OR12; —(CH2)m-C(═O)—OR13 with m=1, 2, 3, 4 or 5; —O—C(═O)—R14; —(CH2)n-O—C(═O)—R15 with n=1, 2, 3, 4 or 5; —OR16; —(CH2)o-O—R17 with o=1, 2, 3; 4 or 5; —SR18; —(CH2)p-S(═O)t-R19 with p=1, 2, 3, 4 or 5 and t=0, 1 or 2; —NH—S(═O)2-R26R27; —S(═O)2-NR28R29, —SF5; a linear or branched, saturated or unsaturated, unsubstituted or at least monosubstituted aliphatic group; a saturated or unsaturated, unsubstituted or at least monosubstituted cycloaliphatic group optionally comprising at least one heteroatom as a ring member, which cycloaliphatic group may be attached via a linear or branched alkylene group and/or may be fused with an unsubstituted or at least monosubstituted mono- or polycyclic ring system; or represent an unsubstituted or at least monosubstituted aryl or heteroaryl group, which may be attached via a linear or branched alkylene group and/or may be fused with an unsubstituted or at least monosubstituted mono- or polycyclic ring system,

or optionally R1a and R1b form an unsubstituted or at least monosubstituted anellated phenyl group with the C—C bridge joining them together,

or optionally R1b and R1c form an unsubstituted or at least monosubstituted anellated phenyl group with the C—C bridge joining them together,

or optionally R1c and R1d form an unsubstituted or at least monosubstituted anellated phenyl group with the C—C bridge joining them together,

R2 and R3, mutually independently, in each case represent a hydrogen; —C(═O)—R20; —(CH2)q-C(═O)—R21 with q=1, 2, 3, 4 or 5; —C(═O)—O—R22; —(CH2)r-C(═O)—O—R23 with r=1, 2, 3, 4 or 5; —C(═O)—NHR24; —(CH2)s-C(═O)—NHR25 with s=1, 2, 3, 4 or 5; a linear or branched, saturated or unsaturated, unsubstituted or at least monosubstituted aliphatic group; a saturated or unsaturated, unsubstituted or at least monosubstituted cycloaliphatic group optionally comprising at least one heteroatom as a ring member, which cycloaliphatic group may be attached via a linear or branched alkylene group and/or may be fused with an unsubstituted or at least monosubstituted mono- or polycyclic ring system; or represent an unsubstituted or at least monosubstituted aryl or heteroaryl group, which may be attached via a linear or branched alkylene group and/or may be fused with an unsubstituted or at least monosubstituted mono- or polycyclic ring system,

or R2 and R3, together with the nitrogen atom joining them together as a ring member, form a saturated or unsaturated heterocycloaliphatic group optionally comprising at least one further heteroatom as a ring member, which heterocycloaliphatic group may be fused with an unsubstituted or at least monosubstituted mono- or polycyclic ring system,

R4, R5, R6, R7, R9, R10, R11, R14 and R15, in each case mutually independently, represent a linear or branched, saturated or unsaturated aliphatic group or an unsubstituted or at least monosubstituted aryl or heteroaryl group, which may be attached via a linear or branched alkylene group and/or may be fused with an unsubstituted or at least monosubstituted mono- or polycyclic ring system,

R8, R12, R13, R16, R17, R18, R19, R20, R21, R22, R23, R24, R25, R26, R27, R28 and R29, in each case mutually independently, represent a hydrogen; a linear or branched, saturated or unsaturated aliphatic group or an unsubstituted or at least monosubstituted aryl or heteroaryl group, which may be attached via a linear or branched alkylene group and/or may be fused with an unsubstituted or at least monosubstituted mono- or polycyclic ring system,

M1 represents an aryl or heteroaryl group, which may be substituted with at least one further substituent and/or fused with an unsubstituted or at least monosubstituted mono- or polycyclic ring system,

M2 represents an aryl or heteroaryl group, which is unsubstituted or at least monosubstituted and optionally fused with an unsubstituted or at least monosubstituted mono- or polycyclic ring system,

in each case optionally in the form of one of the pure stereoisomers thereof, in particular enantiomers or diastereomers, the racemates thereof or in the form of a mixture of stereoisomers, in particular the enantiomers and/or diastereomers, in any desired mixing ratio, or in each case in the form of corresponding salts or in each case in the form of corresponding solvates.

If one or more of the substituents R1a, R1b, R1c, R1d and R2 to R29 represent a saturated or unsaturated aliphatic group, i.e. an alkyl-, alkenyl- or alkynyl group, which is mono- or polysubstituted, this may preferably be substituted with 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, —NO2, —CN, —OH, —SH and —NH2. Alkenyl groups comprise at least one, preferably 1, 2, 3 or 4 C—C double bonds and alkynyl groups comprise at least one, preferably 1, 2, 3 or 4 C—C triple bonds.

Examples of suitable alkyl, alkenyl and alkynyl groups, which may be mono- or polysubstituted, are methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, 2-pentyl, 3-pentyl, iso-pentyl, neopentyl, n-hexyl, 2-hexyl, 3-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, —C(H)(n-C3H7)2, —CH2-CH2-C(H)(CH3)-(CH2)3-CH3, (1,1,3,3-tetramethyl)-butyl, (1,1)-dimethyl-pentyl, (1,1)-dimethyl-butyl, vinyl, ethynyl, 1-propenyl, 2-propenyl, 1-propynyl, 2-propynyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, hexenyl, hexynyl, —CH═CH—CH═CH—CH3 and —CH2-CH2-CH═CH2.

Examples of suitable substituted alkyl and alkenyl groups are trifluoromethyl, difluoromethyl, monofluoromethyl, —(CH2)-OH, —(CH2)-NH2, —(CH2)-CN, —(CH2)-(CF3), —(CH2)-(CHF2), —(CH2)-(CH2F), —(CH2)-(CH2)-OH, —(CH2)-(CH2)-NH2, —(CH2)-(CH2)-CN, —(CF2)-(CF3), —(CH2)-(CH2)-(CF3), —CH═CH—(CH2)-OH, —CH═CH—(CH2)-NH2, —CH═CH—CN and —(CH2)-(CH2)-(CH2)-OH.

If one or more of the substituents R1a, R1b, R1c, R1d, R2 and R3 represent a cycloaliphatic group or comprise a cycloaliphatic group, which is mono- or polysubstituted, this may preferably optionally be substituted with 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —CN, —CF3, —SF5, —OH, —NH2, —O—CF3, —SH, —O—C1-5-alkyl, —(CH2)-O—C1-5-alkyl, —S—C1-5-alkyl, —C1-5 alkyl, —C2-5 alkenyl, —C2-5 alkynyl, —C(═O)—O—C1-5-alkyl, —C(═O)—CF3, —S(═O)2-C1-5-alkyl, —S(═O)—C1-5-alkyl, —S(═O)2-phenyl, oxo (═O), thioxo (═S), —N(C1-5-alkyl)2, —N(H)(C1-5-alkyl), —NO2, —S—CF3, —C(═O)—OH, —NH—S(═O)2-C1-5-alkyl, —NH—C(═O)-C1-5-alkyl, —C(═O)—H; —C(═O)—C1-5-alkyl, —C(═O)—NH2, —C(═O)—N(C1-5-alkyl)2, —C(═O)—N(H)(C1-5-alkyl) and phenyl, wherein the above-stated C1-5 alkyl groups may in each case be linear or branched and the phenyl groups may in each case be unsubstituted or substituted with 1, 2, 3 or 4 substituents mutually independently selected from the group consisting of F, Cl, Br, I, methyl, ethyl, methoxy and ethoxy.

Particularly preferably, the substituents may be selected, in each case mutually independently, from the group consisting of F, Cl, Br, I, —CN, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, ethenyl, propenyl, ethynyl, propynyl, —OH, oxo, thioxo, —O—CH3, —O—C2H5, —O—C3H7, —(CH2)-O—CH3, —(CH2)-O—C2H5, —NH2, —N(CH3)2, —N(C)2H5)2, —NH—CH3, —NH—C2H5, —NO2, —CF3, —SF5, —O—CF3, —S—CF3, —SH, —S—CH3, —S—C2H5, —S(═O)—CH3, —S(═O)—C2H5, —S(═O)2-CH3, —S(═O)2-C2H5, —NH—S(═O)2-CH3, —C(═O)—OH, —C(═O)—H, —C(═O)—CH3, —C(═O)—C2H5, —C(═O)—N(CH3)2, —C(═O)—NH—CH3, —C(═O)—NH2, —NH—C(═O)—CH3, —NH—C(═O)—C2H5, —C(═O)—O—CH3, —C(═O)—O—C2H5, —C(═O)—O—C(CH3)3 and phenyl, wherein the phenyl group may be substituted with 1, 2 or 3 substituents mutually independently selected from the group consisting of F, Cl, Br, methyl and methoxy.

If the cycloaliphatic groups comprise one or more heteroatoms as ring members, these may preferably optionally comprise 1, 2, 3, 4 or 5, particularly preferably 1, 2 or 3, heteroatoms as ring member(s), which may be selected in each case mutually independently from the group consisting of nitrogen, oxygen and sulfur.

Examples of cycloaliphatic groups which may be mono- or polysubstituted are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cycloundecyl, cyclododecyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, oxiranyl, aziridinyl, tetrahydrofuranyl, tetrahydrothienyl, pyrrolidinyl, isoxazolidinyl, isothioazolidinyl, pyrazolidinyl, oxazolidinyl, thiazolidinyl, imidazolidinyl, (1,2,4)-oxadiazolidinyl, (1,2,4)-thiadiazolidinyl, (1,2,4)-triazolidin-3-yl, (1,3,4)-thiadiazolidinyl, (1,3,4)-triazolidin-1-yl, (1,3,4)-triazolidin-2-yl, (2,3)-dihydrofuryl, (2,5)-dihydrofuryl, (2,3)-dihydrothienyl, (2,5)-dihydrothienyl, (2,3)-dihydropyrrolyl, (2,5)-dihydropyrrolyl, (2,3)-dihydroisoxazolyl, (4,5)-dihydroisoxazolyl, (2,5)-dihydroisothiazolyl, (2,3)-dihydropyrazolyl, (4,5)-dihydropyrazolyl, (2,5)-dihydropyrazolyl, (2,3)-dihydrooxazolyl, (4,5)-dihydrooxazolyl, (2,5)-dihydrooxazolyl, (2,3)-dihydrothiazolyl, (4,5)-dihydrothiazolyl, (2,5)-dihydrothiazolyl, (2,3)-dihydroimidazolyl, (4,5)-dihydroimidazolyl, (2,5)-dihydroimidazolyl, morpholinyl, piperidinyl, piperazinyl, azocanyl, tetrahydropyridazinyl, tetrahydropyrimidinyl, tetrahydropyrazinyl, (1,3,5)-tetrahydrotriazinyl, (1,2,4)-tetrahydrotriazin-1-yl, (1,2,4)-tetrahydrotriazin-3-yl, (1,3)-dihydrooxazinyl, (1,3)-dithian-2-yl, tetrahydropyranyl, (1,3)-dioxolan-2-yl, (3,4,5,6)-tetrahydropyridin-2-yl, (1,2,5,6)-tetrahydropyridin-1-yl, (1,2,3,4)-tetrahydropyridin-1-yl, (1,2)-dihydropyridin-1-yl, (1,4)-dihydropyridin-1-yl, 4H-1,3-thiazinyl, (1,3)-dihydrooxazin-2-yl, azepanyl, (1,4)-diazepanyl, thiomorpholinyl and dithiolanyl.

Particularly preferred examples of cycloaliphatic groups, which may be mono- or polysubstituted, are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, imidazolidinyl, tetrahydrofuranyl(tetrahydrofuryl), piperidinyl, piperazinyl, morpholinyl, pyrrolidinyl, tetrahydrothiophenyl, tetrahydropyranyl, thiomorpholinyl, dioxolanyl, azepanyl, diazepanyl, azocanyl and dithiolanyl.

If the cycloaliphatic group is fused with an unsubstituted or at least monosubstituted mono- or polycyclic ring system, suitable unsubstituted or at least monosubstituted groups may be selected from the group consisting of 2,3-dihydro-benzo[1,4]dioxinyl; 3,4-dihydro-2H-benzo[1,4]oxazinyl; benzo[1,3]dioxolyl; (1,2,3,4)-tetrahydroquinazolinyl; indanyl; (1,2,3,4)-tetrahydronaphthyl; 1H-indenyl; (1,2,3,4)-tetrahydroquinolinyl; (1,2,3,4)-tetrahydroisochinolinyl; (2,3)-dihydro-1H-indolyl, (2,3)-dihydro-1H-isoindolyl and decahydroisoquinolinyl.

If the substituents R2 and R3, together with the nitrogen atom joining them together as a ring member, form a saturated or unsaturated heterocycloaliphatic group, which is mono- or polysubstituted, this may preferably optionally be substituted with 1, 2, 3, 4, or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —CN, —CF3, —SF5, —OH, —NH2, —O—CF3, —SH, —O—C1-5-alkyl, —(CH2)-O—C1-5-alkyl, —S—C1-5-alkyl, —C1-5 alkyl, —C2-5 alkenyl, —C2-5 alkynyl, —C(═O)—O—C1-5-alkyl, —C(═O)—CF3, —S(═O)2-C1-5-alkyl, —S(═O)—C1-5-alkyl, —S(═O)2-phenyl, oxo (═O), thioxo (═S), —N(C1-5-alkyl)2, —N(H)(C1-5-alkyl), —NO2, —S—CF3, —C(═O)—OH, —NH—S(═O)2-C1-5-alkyl, —NH—C(═O)—C1-5-alkyl, —C(═O)—H; —C(═O)—C1-5-alkyl, —C(═O)—NH2, —C(═O)—N(C1-5-alkyl)2, —C(═O)—N(H)(C1-5-alkyl) and phenyl, wherein the above-stated C1-5 alkyl groups may in each case be linear or branched and the phenyl groups may in each case be unsubstituted or substituted with 1, 2, 3 or 4 substituents mutually independently selected from the group consisting of F, Cl, Br, I, methyl, ethyl, methoxy and ethoxy.

Particularly preferably, the substituents may be selected, in each case mutually independently, from the group consisting of F, Cl, Br, I, —CN, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, ethenyl, propenyl, ethynyl, propynyl, —OH, oxo, thioxo, —O—CH3, —O—C2H5, —O—C3H7, —(CH2)-O—CH3, —(CH2)-O—C2H5, —NH2, —N(CH3)2, —N(C2H5)2, —NH—CH3, —NH—C2H5, —NO2, —CF3, —SF5, —O—CF3, —S—CF3, —SH, —S—CH3, —S—C2H5, —S(═O)—CH3, —S(═O)—C2H5, —S(═O)2-CH3, —S(═O)2-C2H5, —NH—S(═O)2-CH3, —C(═O)—OH, —C(═O)—H, —C(═O)—CH3, —C(═O)—C2H5, —C(═O)—N(CH3)2, —C(═O)—NH—CH3, —C(═O)—NH2, —NH—C(═O)—CH3, —NH—C(═O)—C2H5, —C(═O)—O—CH3, —C(═O)—O—C2H5, —C(═O)—O—C(CH3)3 and phenyl, wherein the phenyl group may be substituted with 1, 2 or 3 substituents mutually independently selected from the group consisting of F, Cl, Br, methyl and methoxy.

If the heterocycloaliphatic groups comprise one or more heteroatoms as ring members, these may preferably optionally comprise 1, 2, 3, 4 or 5, particularly preferably 1, 2 or 3, heteroatoms as ring member(s), which may, in each case mutually independently, be selected from the group consisting of nitrogen, oxygen and sulfur.

Examples of suitable heterocycloaliphatic groups, which may be mono- or polysubstituted, are imidazolidinyl, piperidinyl, piperazinyl, morpholinyl, pyrrolidinyl, thiomorpholinyl, azepanyl, diazepanyl and azocanyl.

If the cycloaliphatic group is fused with an unsubstituted or at least monosubstituted mono- or polycyclic ring system, suitable unsubstituted or at least monosubstituted groups may be selected from the group consisting of (3,4)-dihydro-2H-benzo[1,4]oxazinyl; (1,2,3,4)-tetrahydroquinazolinyl; (1,2,3,4)-tetrahydroquinolinyl; (1,2,3,4)-tetrahydroisoquinolinyl; (2,3)-dihydro-1H-indolyl, (2,3)-dihydro-1H-isoindolyl and decahydroisoquinolinyl.

If one or more of the substituents R1a, R1b, R1c, R1d, R2 to R29 and M1 and M2 represent an aryl or heteroaryl group or comprise an aryl or heteroaryl group, which is mono- or polysubstituted, this may preferably optionally be substituted with 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of halogen, —CN, —CH2-CN, —NO2, —OH, —SH, —NH2, —CH2-NH2, —C(═O)—OH, C1-5-alkyl, —(CH2)-OH, —(CH2)-O—C1-5-alkyl, —C2-5-alkenyl, —C2-5alkynyl, —S—C1-5-alkyl, —O—C1-5alkyl, —CF3, —SF5, —CHF2, —CH2F, —O—CF3, —O—CHF2, —O—CH2F, —C(═O)—CF3, —S—CF3, —S—CHF2, —S—CH2F, —S(═O)2-phenyl, —S(═O)2-C1-5-alkyl, —S(═O)—C1-5alkyl, —NH—C1-5alkyl, —N—(C1-5-alkyl)2, —CH2-NH—C1-5-alkyl, —CH2-N—(C1-5-alkyl)2, —C(═O)—O—C1-5-alkyl, —C(═O)—H, —C(═O)—C1-5-alkyl, —CH2-O—C(═O)-phenyl, —O—C(═O)-phenyl, —NH—S(═O)2-C1-5-alkyl, —NH—C(═O)—C1-5-alkyl, —S(═O)2-NH2, —S(═O)2-NH—C1-5-alkyl, —S(═O)2-N(C1-5-alkyl)2, —NH—C(═NH)—NH2, —NH—S(═O)2-OH, —C(═O)—NH—C1-5-alkyl, —C(═O)—NH2, —C(═O)—N(C1-5-alkyl)2, —Si(phenyl)2[C1-5-alkyl], pyrazolyl, pyrrolyl, (1,3)-dioxolanyl, phenyl, furyl (furanyl), thiazolyl, thiadiazolyl, thiophenyl (thienyl), phenoxy, benzyl and phenethyl, wherein the cyclic substituents may themselves in each case optionally be substituted with 1, 2, 3 or 4 substituents mutually independently selected from the group consisting of F, Cl, Br, I), —CF3, methyl, ethyl, methoxy and ethoxy.

Particularly preferably, the substituents may be selected, in each case mutually independently, from the group consisting of F, Cl, Br, I, —CN, —CH2-CN, —NO2, —OH, —SH, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, neo-pentyl, ethenyl, propenyl, ethynyl, propynyl, —CH2-OH, —CH2-O—CH3, —CH2-O—C2H5, —OH, —SH, —NH2, —CH2-NH2, —C(═O)—OH, —S—CH3, —S—C2H5, —S(═O)—CH3, —S(═O)—C2H5, —S(═O)2-CH3, —S(═O)2-C2H5, —O—CH3, —O—C2H5, —O—C3H7, —O—C(CH3)3, —CF3, —SF5, —CHF2, —CH2F, —O—CF3, —O—CHF2, —O—CH2F, C(═O)—CF3, —S—CF3, —S—CHF2, —S—CH2F, —S(═O)2-phenyl, pyrazolyl, pyrrolyl, —N(CH3)2, —N(C2H5)2, —NH—CH3, —NH—C2H5, —CH2-O—C(═O)-phenyl, —S(═O)2-NH2, —S(═O)2-NH—CH3, —S(═O)2-N(CH3)2, —NH—C(═NH)—NH2, —NH—S(═O)2-OH, —NH—S(═O)2-CH3, —C(═O)—O—CH3, —C(═O)—O—C2H5, —C(═O)—O—C(CH3)3, —C(═O)—H, —C(═O)—CH3, —C(═O)—C2H5, —C(═O)—C(CH3)3, —NH—C(═O)—CH3, —NH—C(═O)—C2H5, —O—C(═O)-phenyl, —C(═O)—NH2, —C(═O)—NH—CH3, —C(═O)—N(CH3)2, —Si(phenyl)2[C(CH3)3], phenyl, (1,3)-dioxolanyl, furyl (furanyl), thiadiazolyl, thiophenyl (thienyl), phenoxy and benzyl, wherein the cyclic substituents may themselves in each case optionally be substituted with 1, 2, 3 or 4 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —CF3, methyl and methoxy.

Examples of suitable aryl groups which may be mentioned are phenyl, 1-naphthyl, 2-naphthyl and anthracenyl.

If one or more of the substituents R1a, R1b, R1c, R1d, R2 to R29 and M1 and M2 represent a heteroaryl group or comprise a heteroaryl group, the heteroatom(s) thereof may preferably be selected, mutually independently, from the group consisting of oxygen, sulfur and nitrogen. Preferably, a heteroaryl group may optionally comprise 1, 2, 3, 4 or 5, particularly preferably 1, 2 or 3 heteroatoms.

Examples of suitable heteroaryl groups are for example furyl (furanyl), thienyl (thiophenyl), pyrazolyl, imidazolyl, thiazolyl, thiadiazolyl, triazolyl, pyrrolyl, oxazolyl, oxadiazolyl, isoxazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, pyranyl, diazinyl, triazinyl, tetrazinyl, tetrazolyl, purinyl, dithiazolyl and pentazolyl.

If the heteroaryl group is fused with an unsubstituted or at least monosubstituted mono- or polycyclic ring system, suitable unsubstituted or at least monosubstituted heteroaryl groups may be selected from the group consisting of indolyl, isoindolyl, benzo[b]furanyl, isobenzo[b]furanyl, indazolyl, indolizinyl, quinolinyl, isoquinolinyl, quinazolinyl, benzo[b]thiophenyl and isobenzo[b]thiophenyl.

If the substituents R1a and R1b or R1b and R1c or R1c and R1d, together with the C—C bridge joining them together, form an anellated phenyl group, which is mono- or polysubstituted, this may preferably be substituted with 1, 2, 3 or 4 substituents mutually independently selected from the group consisting of halogen, —CN, —CH2-CN, —NO2, —OH, —SH, —NH2, —CH2-NH2, —C(═O)—OH, C1-5 alkyl, —(CH2)-O—C1-5-alkyl, —C2-5 alkenyl, —C2-5 alkynyl, —S—C1-5-alkyl, —O—C1-5-alkyl, —CF3, —SF5, —CHF2, —CH2F, —O—CF3, —O—CHF2, —O—CH2F, —C(═O)—CF3, —S—CF3, —S—CHF2, —S—CH2F, —S(═O)2-phenyl, —S(═O)2-C1-5-alkyl, —S(═O)—C1-5-alkyl, —NH—C1-5-alkyl, —N—(C1-5-alkyl)2, —CH2-NH—C1-5-alkyl, —CH2-N—(C1-5-alkyl)2, —C(═O)—O—C1-5-alkyl, —C(═O)—H, —C(═O)—C1-5-alkyl, —CH2- O—C(═O)-phenyl, —O—C(═O)-phenyl, —NH—S(═O)2-C1-5-alkyl, —NH—C(═O)—C1-5-alkyl, —C(═O)—NH—C1-5-alkyl, —C(═O)—NH2, —C(═O)—N(C1-5-alkyl)2, —Si(phenyl)2[C1-5-alkyl], pyrazolyl, pyrrolyl, (1,3)-dioxolanyl, phenyl, furyl(furanyl), thiazolyl, thiadiazolyl, thiophenyl(thienyl), phenoxy, benzyl and phenethyl, wherein the cyclic substituents themselves may in each case optionally be substituted with 1, 2, 3 or 4 substituents mutually independently selected from the group consisting of F, Cl, Br, I), —CF3, methyl, ethyl, methoxy and ethoxy.

Particularly preferably, the substituents may be selected, in each case mutually independently, from the group consisting of F, Cl, Br, I, —CN, —CH2-CN, —NO2, —OH, —SH, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, neo-pentyl, ethenyl, propenyl, ethynyl, propynyl, —CH2-O—CH3, —CH2-O—C2H5, —OH, —SH, —NH2, —CH2-NH2, —C(═O)—OH, —S—CH3, —S—C2H5, —S(═O)—CH3, —S(═O)—C2H5, —S(═O)2-CH3, —S(═O)2-C2H5, —O—CH3, —O—C2H5, —O—C3H7, —O—C(CH3)3, —CF3, —SF5, —CHF2, —CH2F, —O—CF3, —O—CHF2, —O—CH2F, C(═O)—CF3, —S—CF3, —S—CHF2, —S—CH2F, —S(═O)2-phenyl, pyrazolyl, pyrrolyl, —N(CH3)2, —N(C2H5)2, —NH—CH3, —NH—C2H5, —CH2-O—C(═O)-phenyl, —NH—S(═O)2-CH3, —C(═O)—O—CH3, —C(═O)—O—C2H5, —C(═O)—O—C(CH3)3, —C(═O)—H, —C(═O)—CH3, —C(═O)—C2H5, —C(═O)—C(CH3)3, —NH—C(═O)—CH3, —NH—C(═O)—C2H5, —O—C(═O)-phenyl, —C(═O)—NH2, —C(═O)—NH—CH3, —C(═O)—N(CH3)2, —Si(phenyl)2[C(CH3)3], phenyl, (1,3)-dioxolanyl, furyl(furanyl), thiadiazolyl, thiophenyl(thienyl), phenoxy and benzyl, wherein the cyclic substituents may themselves in each case optionally be substituted with 1, 2, 3 or 4 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —CF3, methyl and methoxy.

For the purposes of the present invention, a mono- or polycyclic ring system should be understood to mean mono- or polycyclic hydrocarbon groups which may be saturated, unsaturated or aromatic and optionally comprise one or more heteroatoms as ring members. Such a mono- or polycyclic ring system may, for example, be fused (anellated) with a cycloaliphatic group, an aryl group or a heteroaryl group.

If a polycyclic ring system, such as for example a bicyclic ring system, is present, the various rings may in each case mutually independently be of a different degree of saturation, i.e. be saturated, unsaturated or aromatic. The heteroatoms of each ring may, in each case mutually independently, preferably be selected from the group consisting of oxygen, nitrogen and sulfur. Preferably a ring contains 0, 1, 2 or 3 heteroatoms. Preferably, the respective rings of the mono- or polycyclic ring system are 5-, 6- or 7-membered, particularly preferably 5- or 6-membered.

If one or more of the substituents R1a, R1b, R1c, R1d, R2 to R29 and M1 and M2 comprise a monocyclic or polycyclic ring system, which is mono- or polysubstituted, this may preferably optionally be substituted with 1, 2, 3, 4 or 5 substituents, which may mutually independently be selected from the group consisting of halogen, —CN, —NO2, —OH, —SH, —NH2, oxo (═O), thioxo (═S), —C(═O)—OH, —C1-5 alkyl, —C2-5 alkenyl, —C2-5 alkynyl, —(CH2)-O—C1-5-alkyl, —S—C1-5-alkyl, —O—C1-5-alkyl, —CF3, —SF5, —CHF2, —CH2F, —O—CF3, —O—CHF2, —O—CH2F, —C(═O)—CF3, —S—CF3, —S—CHF2, —S—CH2F, —S(═O)2-phenyl, —S(═O)2-C1-5-alkyl, —S(═O)—C1-5-alkyl, —NH—C1-5-alkyl, —N(C1-5-alkyl)(C1-5-alkyl), —C(═O)—O—C1-5-alkyl, —C(═O)—H, —C(═O)—C1-5-alkyl, —CH2-O—C(═O)-phenyl, —O—C(═O)-phenyl, —NH—S(═O)2-C1-5-alkyl, —NH—C(═O)—C1-5-alkyl, —C(═O)—NH2, —C(═O)—NH—C1-5-alkyl, —C(═O)—N(C1-5-alkyl)2, pyrazolyl, phenyl, furyl (furanyl), thiadiazolyl, thiophenyl (thienyl), phenoxy and benzyl, wherein the cyclic substituents may themselves in each case optionally be substituted with 1, 2, 3 or 4 substituents mutually independently selected from the group consisting of F, Cl, Br, I, methyl, ethyl, methoxy and ethoxy.

Particularly preferably, the substituents may be selected, in each case mutually independently, from the group consisting of F, Cl, Br, I, —CN, —NO2, —OH, —SH, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, neo-pentyl, ethenyl, propenyl, ethynyl, propynyl, —CH2-O—CH3, —CH2-O—C2H5, —OH, —SH, —NH2, oxo, thioxo, —C(═O)—OH, —S—CH3, —S—C2H5, —S(═O)—CH3, —S(═O)2-CH3, —S(═O)—C2H5, —S(═O)2-C2H5, —O—CH3, —O—C2H5, —O—C3H7, —O—C(CH3)3, —CF3, —SF5, —CHF2, —CH2F, —O—CF3, —O—CHF2, —O—CH2F, —C(═O)—CF3, —S—CF3, —S—CHF2, —S—CH2F, —S(═O)2-phenyl, pyrazolyl, —N(CH3)2, —N(C2H5)2, —NH—CH3, —NH—C2H5, —CH2-O—C(═O)-phenyl, —NH—S(═O)2-CH3, —C(═O)—O—CH3, —C(═O)—O—C2H5, —C(═O)—H, —C(═O)—CH3, —C(═O)—C2H5, —NH—C(═O)—CH3, —NH—C(═O)—C2H5, —O—C(═O)-phenyl, —C(═O)—NH2, —C(═O)—NH—CH3, —C(═O)—N(CH3)2, phenyl, furyl(furanyl), thiadiazolyl, thiophenyl(thienyl), phenoxy and benzyl, wherein the cyclic substituents may themselves in each case optionally be substituted with 1, 2, 3 or 4 substituents mutually independently selected from the group consisting of F, Cl, Br, I, methyl and methoxy.

If one of the above-stated substituents R1a, R1b, R1c, R1d and R2 to R29 comprises a linear or branched alkylene group, the alkylene group may preferably be selected from the group consisting of —(CH2)-, —(CH2)2-, —C(H)(CH3)-, —(CH2)3-, —(CH2)4-, —(CH2)5- and —C(C2H5)(H)—.

The person skilled in the art will understand that some of the substituted imidazo-3-yl-amine compounds of the general formula I according to the invention may be present in the form of tautomers, which the present invention also provides and which may in each case also be present as active ingredients in the pharmaceutical formulations described below.

Preference is given to substituted imidazo-3-yl-amine compounds of the general formula I, in which

A1 represents a nitrogen atom or a C—R1a group,

A2 represents a nitrogen atom or a C—R1b group,

A3 represents a nitrogen atom or a C—R1c group,

A4 represents a nitrogen atom or a C—R1d group,

R1a, R1b, R1c, R1d, mutually independently, in each case represent a hydrogen; a halogen; —NO2; —CN; —NH2; —NHR4; —NR5R6; —NH—C(═O)—R7; —C(═O)—R8, —C(═O)—NH2; —C(═O)—NHR9; —C(═O)—NR10R11; —C(═O)—OR12; —(CH2)m-C(═O)—OR13 with m=1, 2, 3, 4 or 5; —O—C(═O)—R14; —(CH2)n-O—C(═O)—R15 with n=1, 2, 3, 4 or 5; —OR16; —(CH2)o-O—R17 with o=1, 2, 3, 4 or 5; —SR18; —(CH2)p-S(═O)t-R19 with p=1, 2, 3, 4 or 5 and t=0, 1, or 2; —NH—S(═O)2-R26R27; —S(═O)2-NR28R29, —SF5; a linear or branched, saturated or unsaturated, unsubstituted or at least monosubstituted aliphatic C1-10 group; a saturated or unsaturated, unsubstituted or at least monosubstituted, cycloaliphatic C3-8 group, optionally comprising at least one heteroatom as a ring member, which cycloaliphatic C3-8 group may be attached via a linear or branched C1-5 alkylene group; or represent an unsubstituted or at least monosubstituted 5- to 14-membered aryl or heteroaryl group, which may be attached via a linear or branched C1-5 alkylene group,

or optionally R1a and R1b form an unsubstituted or at least monosubstituted anellated phenyl group with the C—C bridge joining them together

or optionally R1b and R1c form an unsubstituted or at least monosubstituted anellated phenyl group with the C—C bridge joining them together,

or optionally R1c and R1d form an unsubstituted or at least monosubstituted anellated phenyl group with the C—C bridge joining them together,

R2 and R3, mutually independently, in each case represent a hydrogen; —C(═O)—R20; —(CH2)q-C(═O)—R21 with q=1, 2, 3, 4 or 5; —C(═O)—O—R22; —(CH2)r-C(═O)—O—R23 with r=1, 2, 3, 4 or 5; —C(═O)—NHR24; —(CH2)s-C(═O)—NHR25 with s=1, 2, 3, 4 or 5 represent a linear or branched, saturated or unsaturated, unsubstituted or at least monosubstituted aliphatic C1-16 group; a saturated or unsaturated, unsubstituted or at least monosubstituted cycloaliphatic C4-8 group optionally comprising at least one heteroatom as a ring member, which cycloaliphatic C4-8 group may be attached via a linear or branched C1-5 alkylene group; or represent an unsubstituted or at least monosubstituted 5- to 14-membered aryl or heteroaryl group, which may be attached via a linear or branched C1-5 alkylene group,

or R2 and R3, together with the nitrogen atom joining them together as a ring member, form a saturated or unsaturated heterocycloaliphatic C4-10 group optionally comprising at least one further heteroatom as a ring member, which heterocycloaliphatic C4-10 group is optionally fused with an unsubstituted or at least monosubstituted mono- or polycyclic ring system, wherein the rings of the ring system are in each case 5-, 6- or 7-membered;

R4, R5, R6, R7, R9, R10, R11, R14 and R15, in each case mutually independently, represent a linear or branched, saturated or unsaturated aliphatic C1-4 group or represent an unsubstituted or at least monosubstituted 5- to 14-membered aryl or heteroaryl group, which may be attached via a linear or branched C1-5 alkylene group,

R8, R12, R13, R16, R17, R18, R19, R20, R21, R22, R23, R24, R25, R26, R27, R28 and R29, in each case mutually independently, represent a hydrogen; a linear or branched, saturated or unsaturated aliphatic C1-4 group or an unsubstituted or at least monosubstituted 5- to 14-membered aryl or heteroaryl group, which may be attached via a linear or branched C1-5 alkylene group,

M1 represents a 5- or 6-membered aryl or heteroaryl group, which may be substituted with at least one further substituent and is optionally fused with an unsubstituted or at least monosubstituted mono- or bicyclic ring system, wherein the rings of the ring system are in each case 5-, 6- or 7-membered, and

M2 represents a 5- or 6-membered aryl or heteroaryl group, which may be unsubstituted or at least monosubstituted and may be fused with an unsubstituted or at least monosubstituted mono- or bicyclic ring system, wherein the rings of the ring system are in each case 5-, 6- or 7-membered, wherein the above-stated cycloaliphatic groups may optionally comprise 1, 2, 3, 4 or 5 heteroatom(s) as ring member(s), which may be selected, in each case mutually independently, from the group consisting of nitrogen, oxygen and sulfur, the above-stated heterocycloaliphatic groups may optionally comprise a further 1, 2, 3, 4 or 5 heteroatom(s) as ring member(s), which may be selected, in each case mutually independently, from the group consisting of nitrogen, oxygen and sulfur, the rings of the mono- or polycyclic ring system in each case optionally comprise 0, 1, 2 or 3 heteroatom(s) as ring member(s), which are selected mutually independently from the group consisting of oxygen, nitrogen and sulfur; and the above-stated heteroaryl groups may optionally comprise 1, 2, 3, 4 or 5 heteroatom(s) as ring member(s), which may be selected, in each case mutually independently, from the group consisting of nitrogen, oxygen and sulfur; in each case optionally in the form of one of the pure stereoisomers thereof, in particular enantiomers or diastereomers, the racemates thereof or in the form of a mixture of stereoisomers, in particular the enantiomers and/or diastereomers, in any desired mixing ratio, or in each case in the form of corresponding salts or in each case in the form of corresponding solvates.

Also preferred are substituted imidazo-3-yl-amine compounds of the above-stated general formula I, in which

A1 represents a C—R1a group, A2 represents a C—R1b group, A3 represents a C—R1c group and A4 represents a C—R1d group, or

A1 represents a nitrogen atom, A2 represents a C—R1b group, A3 represents a C—R1c group and A4 represents a C—R1d group, or

A1 represents a C—R1a group, A2 represents a nitrogen atom, A3 represents a C—R1c group and A4 represents a C—R1d group, or

A1 represents a C—R1a group, A2 represents a C—R1b group, A3 represents a nitrogen atom and A4 represents a C—R1d group, or

A1 represents a C—R1a group, A2 represents a C—R1b group, A3 represents a C—R1c group and A4 represents a nitrogen atom, or

A1 and A3 in each case represent a nitrogen atom, A2 represents a C—R1b group, and A4 represents a C—R1d group,

and the respective remaining groups R1a, R1b, R1c, R1d, R2 to R29, M1 and M2 have the above-stated meaning, in each case optionally in the form of one of the pure stereoisomers thereof, in particular enantiomers or diastereomers, the racemates thereof or in the form of a mixture of stereoisomers, in particular the enantiomers and/or diastereomers, in any desired mixing ratio, or in each case in the form of corresponding salts, or in each case in the form of corresponding solvates.

Also preferred are substituted imidazo-3-yl-amine compounds of the above-stated general formula I, in which

A1 represents a C—R1a group, A2 represents a C—R1b group, A3 represents a C—R1c group and A4 represents a C—R1d group, or

A1 represents a nitrogen atom, A2 represents a C—R1b group, A3 represents a C—R1c group and A4 represents a C—R1d group, or

A1 represents a C—R1a group, A2 represents a nitrogen atom, A3 represents a C—R1c group and A4 represents a C—R1d group, or

A1 represents a C—R1a group, A2 represents a C—R1b group, A3 represents a C—R1c group and A4 represents a nitrogen atom,

Likewise preferred are substituted imidazo-3-yl-amine compounds of the above-stated general formula I, in which

A1 represents a C—R1a group, A2 represents a C—R1b group, A3 represents a C—R1c group and A4 represents a C—R1d group, or

A1 represents a C—R1a group, A2 represents a nitrogen atom, A3 represents a C—R1c group and A4 represents a C—R1d group, or

A1 represents a nitrogen atom, A2 represents a C—R1b group, A3 represents a C—R1c group and A4 represents a C—R1d group,

Also preferred are substituted imidazo-3-yl-amine compounds of the above-stated general formula I, in which R1a, R1b, R1c, R1d, mutually independently, in each case represent —H; —F; —Cl, —Br; —I; —NO2; —CN; —CF3; —SF5; —NH2; —S(═O)2-NH2; —NHR4; —NR5R6; —C(═O)—OR12; —(CH2)m-C(═O)—OR13 with m=1, 2 or 3; —O—C(═O)—R14; —OR16; —(CH2)o-O—R17 with o=1, 2 or 3; a linear or branched C1-10 alkyl group; or represent an unsubstituted or at least monosubstituted 5- or 6-membered aryl or heteroaryl group, which may be attached via a linear or branched C1-4 alkylene group,

preferably R1a, R1b, R1c, R1d, mutually independently, in each case represent —H; —F; —Cl, —Br; —I; —NO2; —CN; —CF3; —SF5; —NH2; —S(═O)2-NH2; —NHR4; —NR5R6; —C(═O)—OR12; —(CH2)m-C(═O)—OR13 with m=1, 2 or 3; —O—C(═O)—R14; —OR16; —(CH2)o-O—R17 with o=1, 2 or 3; a linear or branched alkyl group selected from the group consisting of methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl and tert-butyl, or an aryl or heteroaryl group selected from the group consisting of phenyl, furanyl, thiophenyl and pyridinyl, which is in each case unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, —CN, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, —OH, —O—CH3, —O—C2H5 and is optionally attached via a —(CH2), —(CH2)2 or —(CH2)3 group,

particularly preferably R1a, R1b, R1c, R1d, mutually independently, in each case represent —H; —F; —Cl, —Br; —CF3; —CN; —SF5; —C(═O)—OR12; —S(═O)2-NH2; —(CH2)m-C(═O)—OR13 with m=1 or 2; —OR16; —(CH2)o-O—R17 with o=1 or 2; a linear or branched alkyl group selected from the group consisting of methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl and tert-butyl, or a phenyl group, which is unsubstituted or substituted with 1, 2 or 3 substituents mutually independently selected from the group consisting of F, Cl, Br, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, —O—CH3, —O—C2H5 and optionally attached via a —(CH2), —(CH2)2 or —(CH2)3 group,

very particularly preferably R1a, R1b, R1c, R1d, mutually independently, in each case represent —H; —F; —Cl, —Br; —CF3; —CN; —SF5; —S(═O)2-NH2; —C(═O)—OR12; —(CH2)m-C(═O)—OR13 with m=1; —OR16; —(CH2)o-O—R17 with o=1; a linear or branched alkyl group selected from the group consisting of methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl and tert-butyl; or represent an unsubstituted phenyl group, which is optionally attached via a —(CH2), —(CH2)2 or —(CH2)3 group,

and the respective remaining groups A1, A2, A3, A4, R2 to R29, M1 and M2 have the above-stated meaning, in each case optionally in the form of one of the pure stereoisomers thereof, in particular enantiomers or diastereomers, the racemates thereof or in the form of a mixture of stereoisomers, in particular the enantiomers and/or diastereomers, in any desired mixing ratio, or in each case in the form of corresponding salts, or in each case in the form of corresponding solvates.

Also preferred are substituted imidazo-3-yl-amine compounds of the above-stated general formula I, in which R1a and R1b or R1b and R1c or R1c and R1d, together with the C—C bridge joining them together, form an anellated phenyl group, which may be substituted with 1, 2, 3 or 4 substituents mutually independently selected from the group consisting of F, Cl, Br, —CN, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, —OH, —O—CH3, —O—C2H5;

The person skilled in the art will understand that, where R1a and R1b, together with the C—C bridge joining them together, form an anellated phenyl group, the following general formula Ia is obtained:

embedded image

The person skilled in the art will understand that, where R1b and R1c, together with the C—C bridge joining them together, form an anellated phenyl group, the following general formula Ib is obtained:

embedded image

The person skilled in the art will understand that, where R1c and R1d, together with the C—C bridge joining them together, form an anellated phenyl group, the following general formula Ic is obtained:

embedded image

Also preferred are substituted imidazo-3-yl-amine compounds of the above-stated general formula I, in which R2 and R3, mutually independently, in each case represent a hydrogen; —C(═O)—R20; —(CH2)q-C(═O)—R21 with q=1, 2, 3, 4 or 5; —(CH2)r-C(═O)—O—R23 with r=1, 2, 3, 4 or 5; —C(═O)—NHR24; a linear or branched C1-16 alkyl group; an unsubstituted or at least monosubstituted C4-8 cycloalkyl group, which may be attached via a linear or branched C1-3 alkylene group; or represent an unsubstituted or at least monosubstituted, 5- or 6-membered aryl or heteroaryl group, which may be attached via a linear or branched C1-3 alkylene group,

preferably R2 and R3, mutually independently, in each case represent a hydrogen; —C(═O)—R20; —(CH2)q-C(═O)—R21 with q=1, 2 or 3; —(CH2)r-C(═O)—O—R23 with r=1, 2 or 3; a linear or branched C1-10 alkyl group; a C4-8 cycloalkyl group, which is in each case unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, —CN, —CF3, —SF5, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, —OH, —O—CH3 and —O—C2H5 and is optionally attached via a linear or branched C1-3 alkylene group; or represent an aryl or heteroaryl group selected from the group consisting of phenyl, thiophenyl, furanyl and pyridinyl, which is in each case unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, —CN, —CF3, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, —OH, —O—CH3 and —O—C2H5 and is optionally attached via a linear or branched C1-3 alkylene group,

particularly preferably R2 and R3, mutually independently, in each case represent a hydrogen; —C(═O)—R20; —(CH2)q-C(═O)—R21 with q=1 or 2; —(CH2)r-C(═O)—O—R23 with r=1 or 2; an alkyl group selected from the group consisting of methyl; ethyl; propyl; iso-propyl; n-butyl; tert-butyl; sec-butyl; iso-butyl; n-pentyl; n-hexyl; n-heptyl; n-octyl; (1,1,3,3)-tetramethyl-butyl; an unsubstituted cyclopentyl or cyclohexyl group, which may in each case be attached via a —(CH2)-, —(CH2)2 or —(CH2)3 group; or represent a phenyl or pyridinyl group, which is in each case unsubstituted or substituted with 1, 2 or 3 substituents mutually independently selected from the group consisting of F, Cl, Br, —CN, —CF3, methyl, ethyl, n-propyl, iso-propyl, tert-butyl, —O—CH3 and —O—C2H5 and is optionally attached via a —(CH2), —(CH2)2, —C(H)(CH3) or —(CH2)3 group,

and the respective remaining groups A1, A2, A3, A4, R1a, R1b, R1c, R1d, R4 to R29, M1 and M2 have the above-stated meaning, in each case optionally in the form of one of the pure stereoisomers thereof, in particular enantiomers or diastereomers, the racemates thereof or in the form of a mixture of stereoisomers, in particular the enantiomers and/or diastereomers, in any desired mixing ratio, or in each case in the form of corresponding salts, or in each case in the form of corresponding solvates.

Likewise preferred are substituted imidazo-3-yl-amine compounds of the above-stated general formula I, in which one the groups R2 and R3 represents a hydrogen; or represents a linear or branched C1-16 alkyl group and the other one of these two groups represents a hydrogen; —C(═O)—R20; —(CH2)q-C(═O)—R21 with q=1, 2, 3, 4 or 5; —(CH2)r-C(═O)—O—R23 with r=1, 2, 3, 4 or 5; —C(═O)—NHR24; a linear or branched C1-16 alkyl group; an unsubstituted or at least monosubstituted C4-8 cycloalkyl group, which may be attached via a linear or branched C1-3 alkylene group; or represents an unsubstituted or at least monosubstituted, 5- or 6-membered aryl or heteroaryl group, which may be attached via a linear or branched C1-3 alkylene group,

preferably one of the two groups R2 and R3 represents a hydrogen; or represents a linear or branched C1-10 alkyl group and the other one of these two groups represents a hydrogen; —C(═O)—R20; —(CH2)q-C(═O)—R21 with q=1, 2 or 3; —(CH2)r-C(═O)—O—R23 with r=1, 2 or 3; a linear or branched C1-10 alkyl group; a C4-8 cycloalkyl group, which is in each case unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, —CN, —CF3, —SF5, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, —OH, —O—CH3 and —O—C2H5 and is optionally attached via a linear or branched C1-3 alkylene group; or represents an aryl or heteroaryl group selected from the group consisting of phenyl, thiophenyl, furanyl and pyridinyl, which is in each case unsubstituted or optionally substituted with 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, —CN, —CF3, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, —OH, —O—CH3 and —O—C2H5 and is optionally attached via a linear or branched C1-3 alkylene group,

particularly preferably one of the two groups R2 and R3 represents a hydrogen or an alkyl group selected from the group consisting of methyl; ethyl; propyl; iso-propyl; n-butyl; tert-butyl; sec-butyl; iso-butyl; n-pentyl; n-hexyl; n-heptyl; n-octyl; (1,1,3,3)-tetramethyl-butyl and the other one of these two groups represents a hydrogen; —C(═O)—R20; —(CH2)q-C(═O)—R21 with q=1 or 2; —(CH2)r-C(═O)—O—R23 with r=1 or 2; an alkyl group selected from the group consisting of methyl; ethyl; propyl; iso-propyl; n-butyl; tert-butyl; sec-butyl; iso-butyl; n-pentyl; n-hexyl; n-heptyl; n-octyl; (1,1,3,3)-tetramethyl-butyl, (1,1)-dimethyl-pentyl and (1,1)-dimethyl-butyl; an unsubstituted cyclopentyl or cyclohexyl group, which may in each case be attached via a —(CH2), —(CH2)2 or —(CH2)3 group; or represents a phenyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 2-furanyl, 3-furanyl, 2-thiophenyl or 3-thiophenyl group, which is in each case unsubstituted or optionally substituted with 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, —CN, —CF3, methyl, ethyl, n-propyl, iso-propyl, tert-butyl, —O—CH3 and —O—C2H5 and is optionally attached via a —(CH2), —(CH2)2, —C(H)(CH3) or —(CH2)3 group,

Likewise preferred are substituted imidazo-3-yl-amine compounds of the above-stated general formula I, in which R2 and R3, together with the nitrogen atom joining them together as a ring member, form a group selected from the group consisting of imidazolidinyl, piperidinyl, piperazinyl, morpholinyl, pyrrolidinyl, thiomorpholinyl, azepanyl, diazepanyl and azocanyl, which is in each case unsubstituted or optionally substituted with 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —CN, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, —OH, oxo, thioxo, —O—CH3, —O—C2H5, —O—C3H7, —NH2, —N(CH3)2, —N(C2H5)2, —NH—CH3, —NH—C2H5, —O—CF3, —S—CF3, —S(═O)—CH3, —S(═O)—C2H5, —S(═O)2-CH3, —S(═O)2-C2H5, —C(═O)—OH, —C(═O)—H, —C(═O)—CH3, —C(═O)—C2H5, —C(═O)—N(CH3)2, —C(═O)—NH—CH3, —C(═O)—NH2, —C(═O)—O—CH3, —C(═O)—O—C2H5 and —C(═O)—O—C(CH3)3,

preferably R2 and R3, together with the nitrogen atom joining them together as a ring member, form a group selected from the group consisting of imidazolidinyl, piperidinyl, piperazinyl, morpholinyl, pyrrolidinyl, thiomorpholinyl, azepanyl, diazepanyl and azocanyl;

Also preferred are substituted imidazo-3-yl-amine compounds of the above-stated general formula I preferably, in which R4, R5, R6, R7, R9, R10, R11, R14 and R15, in each case mutually independently, represent a linear or branched C1-4 alkyl group or an unsubstituted or at least monosubstituted 5- to 14-membered aryl or heteroaryl group, which may be attached via a linear or branched C1-5 alkylene group,

preferably R4, R5, R6, R7, R9, R10, R11, R14 and R15, in each case mutually independently, represent an alkyl group selected from the group consisting of methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl and tert-butyl, or represent an unsubstituted or at least monosubstituted 5- or 6-membered aryl or heteroaryl group, which may be attached via a linear or branched C1-3 alkylene group,

particularly preferably R4, R5, R6, R7, R9, R10, R11, R14 and R15, in each case mutually independently, represent an alkyl group selected from the group consisting of methyl, ethyl, n-propyl and iso-propyl, or represent a phenyl group, which is in each case unsubstituted or substituted with 1, 2 or 3 substituents mutually independently selected from the group consisting of F, Cl, Br, —CN, —CF3, —SF5, methyl, ethyl, n-propyl, iso-propyl, tert-butyl, —O—CH3 and —O—C2H5 and is optionally attached via a —(CH2), —(CH2)2 or —(CH2)3 group, and in each case the remaining groups A1, A2, A3, A4, R1a, R1b, R1c, R1d, R2, R3, R8, R12, R13 and R16 to R29, M1 and M2 have the above-stated meaning, in each case optionally in the form of one of the pure stereoisomers thereof, in particular enantiomers or diastereomers, the racemates thereof or in the form of a mixture of stereoisomers, in particular the enantiomers and/or diastereomers, in any desired mixing ratio, or in each case in the form of corresponding salts or in each case in the form of corresponding solvates.

Also preferred are substituted imidazo-3-yl-amine compounds of the above-stated general formula I, in which R8, R12, R13, R16, R17, R18, R19, R20, R21, R22, R23, R24, R25, R26, R27, R28 and R29, in each case mutually independently, represent a hydrogen; a linear or branched C1-8 alkyl group, or an unsubstituted or at least monosubstituted 5- to 14-membered aryl or heteroaryl group, which may be attached via a linear or branched C1-5 alkylene group,

preferably R8, R12, R13, R16, R17, R18, R19, R20, R21, R22, R23, R24, R25, R26, R27, R28 and R29, in each case mutually independently, represent a hydrogen; a linear or branched, saturated or unsaturated aliphatic C1-4 group or an unsubstituted or at least monosubstituted 5- to 6-membered aryl or heteroaryl group, which may be attached via a linear or branched C1-3 alkylene group,

particularly preferably R8, R12, R13, R16, R17, R18, R19, R20, R21, R22, R23, R24, R25, R26, R27, R28 and R29, in each case mutually independently, represent a hydrogen; an alkyl group selected from the group consisting of methyl, ethyl, n-propyl and iso-propyl and tert-butyl, or represent a phenyl group, which is in each case unsubstituted or substituted with 1, 2 or 3 substituents mutually independently selected from the group consisting of F, Cl, Br, —CN, —CF3, —SF5, methyl, ethyl, n-propyl, iso-propyl, tert-butyl, —O—CH3 and —O—C2H5 and is optionally attached via a —(CH2), —(CH2)2 or —(CH2)3 group,

and in each case the remaining groups A1, A2, A3, A4, R1a, R1b, R1c, R1d, R2 to R7, R9 to R11, R14 and R15, M1 and M2 have the above-stated meaning, in each case optionally in the form of one of the pure stereoisomers thereof, in particular enantiomers or diastereomers, the racemates thereof or in the form of a mixture of stereoisomers, in particular the enantiomers and/or diastereomers, in any desired mixing ratio, or in each case in the form of corresponding salts or in each case in the form of corresponding solvates.

Likewise preferred are substituted imidazo-3-yl-amine compounds of the above-stated general formula I, in which M1 represents a 5- or 6-membered aryl or heteroaryl group, which may be substituted with at least one further substituent, wherein the heteroaryl group optionally comprises 1, 2, 3, 4 or 5 heteroatom(s) as ring member(s), which are mutually independently selected from the group consisting of nitrogen, oxygen and sulfur,

preferably M1 represents an aryl or heteroaryl group selected from the group consisting of phenyl, furanyl, thiophenyl, pyrazolyl, pyrazinyl, pyridazinyl, pyrimidinyl, pyridinyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, thiadiazolyl, imidazolyl, oxadiazolyl, triazolyl, diazinyl, triazinyl, tetrazinyl and tetrazolyl, which may be substituted with at least one further substituent, particularly preferably represents a group selected from the group consisting of groups 1 to 38,

embedded image

which may be attached in any desired direction at the indicated positions in the parent structure and may be substituted with at least one further substituent,

very particularly preferably represents a group selected from the group consisting of groups 1 to 38,

embedded image

which may be attached in any desired direction at the indicated positions in the parent structure and is optionally substituted with 1, 2, 3 or 4 further substituents, which may mutually independently be selected from the group consisting of F, Cl, Br, —CN, —CH2-CN, —CF3, —SF5, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, —OH, —O—CH3, —O—C2H5, —O—C3H7, —NH2, —N(CH3)2, —N(C2H5)2, —NO2, —O—CF3, —S—CF3, —SH, —C(═O)—CH3 and —C(═O)—C2H5,

still more preferably represents a group selected from the group consisting of groups 1 to 9, 11, 21, 22 and 36 to 38,

embedded image

most preferably represents a group selected from the group consisting of groups 1 to 9, 11, 21, 22 and 36 to 38,

embedded image

which may be attached in any desired direction at the indicated positions in the parent structure and is optionally substituted with 1 or 2 further substituents, which may mutually independently be selected from the group consisting of F, Cl, Br, —CN, —CH2-CN, —CF3, —SF5, methyl, ethyl, n-propyl, iso-propyl, tert-butyl, —O—CH3 and —O—CF3,

and the respective remaining groups A1, A2, A3, A4, R1a, R1b, R1c, R1d, R2 to R29 and M2 have the above-stated meaning, in each case optionally in the form of one of the pure stereoisomers thereof, in particular enantiomers or diastereomers, the racemates thereof or in the form of a mixture of stereoisomers, in particular the enantiomers and/or diastereomers, in any desired mixing ratio, or in each case in the form of corresponding salts, or in each case in the form of corresponding solvates.

Also preferred are substituted imidazo-3-yl-amine compounds of the above-stated general formula I, in which M2 represent an unsubstituted or at least monosubstituted 5- or 6-membered aryl or heteroaryl group, wherein the heteroaryl group comprises 1, 2, 3, 4 or 5 heteroatom(s) as ring member(s), which are mutually independently selected from the group consisting of nitrogen, oxygen and sulfur, and wherein the aryl or heteroaryl group may be fused with an unsubstituted or at least monosubstituted mono- or bicyclic ring system, wherein the rings of the ring system are in each case 5- or 6-membered and may in each case comprise 1, 2, 3 or 4 heteroatom(s) as ring member(s), which are mutually independently selected from the group consisting of nitrogen, oxygen and sulfur,

preferably M2 represents a group selected from the group consisting of phenyl, furanyl, thiophenyl, pyrazolyl, pyrazinyl, pyridazinyl, pyrimidinyl, pyridinyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, thiadiazolyl, oxadiazolyl, triazolyl, diazinyl, triazinyl, tetrazinyl, tetrazolyl, pentazolyl, imidazolyl, quinolinyl, isoquinolinyl, naphthyl, indolyl, isoindolyl, benzofuranyl, isobenzofuranyl, benzothiophenyl and isobenzothiophenyl, wherein the group may in each case be unsubstituted or at least monosubstituted,

particularly preferably M2 represents a group selected from the group consisting of phenyl, furanyl, thiophenyl, pyrazolyl, pyrazinyl, pyridazinyl, pyrimidinyl, pyridinyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, thiadiazolyl, oxadiazolyl, triazolyl, diazinyl, triazinyl, tetrazinyl, tetrazolyl, pentazolyl, imidazolyl, quinolinyl, isoquinolinyl, naphthyl, indolyl, isoindolyl, benzofuranyl, isobenzofuranyl, benzothiophenyl and isobenzothiophenyl, wherein the respective group may be unsubstituted or optionally substituted with 1, 2, 3, 4 or 5 substituents, which are mutually independently selected from the group consisting of F, Cl, Br, —CN, —CF3, —SF5, —S—CH3, —S—C2H5, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, ethenyl, propenyl, —OH, —O—CH3, —O—C2H5, —O—C3H7, —NH2, —N(CH3)2, —NH—CH3, —CH2-NH2, —N(C2H5)2, —NO2, —O—CF3, —C(═O)—H, —S—CF3, —SH, —C(═O)—O—CH3, —C(═O)—O—C2H5, phenyl, pyrrolyl, (1,3)-dioxolanyl, —Si(phenyl)2[C(CH3)3], —C(═O)—CH3, —C(═O)—C2H5, NH—S(═O)2-CH3, —NH—S(═O)2-C2H5, —S(═O)2-NH2, —S(═O)2-NH—CH3, —CH2-OH, —C(═O)—OH, —CH2- O—CH3, —C(═O)—NH2, —C(═O)—NH—CH3, —NH—C(═O)—CH3, —NH—C(═NH)—NH2, —NH—S(═O)2-OH and —S(═O)2-N(CH3)2;

very particularly preferably M2 represents a group selected from the group consisting of groups 1 to 36,

embedded image

which is attached at the indicated point in the parent structure, wherein the respective group may be unsubstituted or optionally substituted with 1, 2, 3, 4, or 5 substituents, which are mutually independently selected from the gropu consisting of F, Cl, Br, —CN, —CF3, —SF5, —S—CH3, —S—C2H5, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, ethenyl, propenyl, —OH, —O—CH3, —O—C2H5, —O—C3H7, —NH2, —N(CH3)2, —NH—CH3, —CH2-NH2, —N(C2H5)2, —NO2, —O—CF3, —S—CF3, —SH, —C(═O)—H, —C(═O)—O—CH3, —C(═O)—O—C2H5, phenyl, pyrrolyl, (1,3)-dioxolanyl, Si(phenyl)2[C(CH3)3], —C(═O)—CH3, —C(═O)—C2H5, NH—S(═O)2-CH3, —NH—S(═O)2-C2H5, —S(═O)2-NH2, —S(═O)2-NH—CH3, —CH2-OH, —C(═O)—OH, —CH2-O—CH3, —C(═O)—NH2, —C(═O)—NH—CH3, —NH—C(═O)—CH3, —NH—C(═NH)—NH2, —NH—S(═O)2-OH and —S(═O)2-N(CH3)2;

most preferably M2 represents a group selected from the group consisting of groups 1 to 36,

embedded image

which is attached at the indicated point in the parent structure, wherein the respective group may be unsubstituted or substituted with 1, 2 or 3 substituents, which are mutually independently selected from the group consisting of F, Cl, Br, —CN, —CF3, —SF5, —S—CH3, —S—C2H5, methyl, ethyl, iso-propyl, tert-butyl, ethenyl, propenyl, —O—CH3, —O—C2H5, —NH2, —N(CH3)2, —NH—CH3, —CH2-NH2, —O—CF3, —C(═O)—H, —C(═O)—O—CH3, —C(═O)—O—C2H5, phenyl, pyrrolyl, (1,3)-dioxolanyl, —Si(phenyl)2[C(CH3)3)], —NO2, NH—S(═O)2-CH3, —NH—S(═O)2-C2H5, —S(═O)2-NH2, —S(═O)2-NH—CH3, —CH2-OH, —C(═O)—CH3, —C(═O)—OH, —CH2-O—CH3, —C(═O)—NH2, —C(═O)—NH—CH3, —NH—C(═O)—CH3, —NH—C(═NH)—NH2, —NH—S(═O)2-OH and —S(═O)2-N(CH3)2;

and the respective remaining groups A1, A2, A3, A4, R1a, R1b, R1c, R1d, R2 to R29 and M1 have the above-stated meaning, in each case optionally in the form of one of the pure stereoisomers thereof, in particular enantiomers or diastereomers, the racemates thereof or in the form of a mixture of stereoisomers, in particular the enantiomers and/or diastereomers, in any desired mixing ratio, or in each case in the form of corresponding salts, or in each case in the form of corresponding solvates.

Particular preference is given to substituted imidazo-3-yl-amine compounds of the general formula I,

A1 represents a C—R1a group, A2 represents a C—R1b group, A3 represents a C—R1c group and A4 represents a C—R1d group; or

A1 represents a nitrogen atom, A2 represents a C—R1b group, A3 represents a C—R1c group and A4 represents a C—R1d group; or

A1 represents a C—R1a group, A2 represents a nitrogen atom, A3 represents a C—R1c group and A4 represents a C—R1d group;

R1a, R1b, R1c, R1d, mutually independently, in each case represent —H; —F; —Cl, —Br; —I; —NO2; —CN; —CF3; —SF5; —NH2; —S(═O)—NH2, —NHR4; —NR5R6; —C(═O)—OR12; —(CH2)m-C(═O)—OR13 with m=1, 2 or 3; —O—C(═O)—R14; —OR16; —(CH2)o-O—R17 with o=1, 2 or 3; a linear or branched alkyl group selected from the group consisting of methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl and tert-butyl, or an aryl or heteroaryl group selected from the group consisting of phenyl, furanyl, thiophenyl and pyridinyl, which is in each case unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, —CN, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, —OH, —O—CH3, —O—C2H5 and optionally attached via a —(CH2)-, —(CH2)2- or —(CH2)3 group;

or optionally R1a and R1b or optionally R1b and R1c or optionally R1c and R1d, together with the C—C bridge joining them together, form an anellated phenyl group, which may be substituted with 1, 2, 3 or 4 substituents mutually independently selected from the group consisting of F, Cl, Br, —CN, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, —OH, —O—CH3, —O—C2H5;

R2 and R3, mutually independently, in each case represent a hydrogen; —C(═O)—R20; —(CH2)q-C(═O)—R21 with q=1, 2 or 3; —(CH2)r-C(═O)—O—R23 with r=1, 2 or 3; a linear or branched C1-10 alkyl group; a C4-8 cycloalkyl group, which is in each case unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, —CN, —CF3, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, —OH, —O—CH3 and —O—C2H5 and is optionally attached via a linear or branched C1-3 alkylene group; or represent an aryl or heteroaryl group selected from the group consisting of phenyl, thiophenyl, furanyl and pyridinyl, which is in each case unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, —CN, —CF3, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, —OH, —O—CH3 and —O—C2H5 and is optionally attached via a linear or branched C1-3 alkylene group;

or R2 and R3, together with the nitrogen atom joining them together as a ring member, form a group selected from the group consisting of imidazolidinyl, piperidinyl, piperazinyl, morpholinyl, pyrrolidinyl, thiomorpholinyl, azepanyl, diazepanyl and azocanyl, which may be in each case unsubstituted or optionally substituted with 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —CN, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, —OH, oxo, thioxo, —O—CH3, —O—C2H5, —O—C3H7, —NH2, —N(CH3)2, —N(C2H5)2, —NH—CH3, —NH—C2H5, —O—CF3, —S—CF3, —S(═O)—CH3, —S(═O)—C2H5, —S(═O)2-CH3, —S(═O)2-C2H5, —C(═O)—OH, —C(═O)—H, —C(═O)—CH3, —C(═O)—C2H5, —C(═O)—N(CH3)2, —C(═O)—NH—CH3, —C(═O)—NH2, —C(═O)—O—CH3, —C(═O)—O—C2H5 and —C(═O)—O—C(CH3)3;

R4, R5, R6 and R14, in each case mutually independently, represent an alkyl group selected from the group consisting of methyl, ethyl, n-propyl and iso-propyl, or represent a phenyl group, which is in each case unsubstituted or substituted with 1, 2 or 3 substituents mutually independently selected from the group consisting of F, Cl, Br, —CN, —CF3, —SF5, methyl, ethyl, n-propyl, iso-propyl, tert-butyl, —O—CH3 and —O—C2H5 and is optionally attached via a —(CH2), —(CH2)2 or —(CH2)3 group;

R12, R13, R16, R17, R20, R21 and R23, in each case mutually independently, represent a hydrogen; an alkyl group selected from the group consisting of methyl, ethyl, n-propyl, iso-propyl and tert-butyl, or a phenyl group, which is in each case unsubstituted or substituted with 1, 2 or 3 substituents mutually independently selected from the group consisting of F, Cl, Br, —CN, —CF3, —SF5, methyl, ethyl, n-propyl, iso-propyl, tert-butyl, —O—CH3 and —O—C2H5 and is optionally attached via a —(CH2), —(CH2)2 or —(CH2)3 group;

M1 represents a group selected from the group consisting of groups 1, 9, 11, 21, 22 and 36 to 38,

embedded image

which may in each case be linked in any desired direction via the positions indicated with a wavy line to the bicyclic ring system and to the carbon atom of the triple bond and is optionally substituted with 1 or 2 further substituents, which are mutually independently selected from the group consisting of F, Cl, Br, —CN, —CH2-CH, —CF3, —SF5, methyl, ethyl, n-propyl, iso-propyl, n-bulyl, iso-butyl, sec-butyl, tert-butyl, —O—CH3 and —O—CF3; and

M2 represents a group selected from the group consisting of groups 1 to 36,

embedded image

which is in each case linked via the position indicated with a wavy line to the carbon atom of the triple bond and is unsubstituted or optionally substituted with 1, 2 or 3 substituents, which are mutually independently selected from the group consisting of F, Cl, Br, —CN, —CF3, —SF5, —S—CH3, —S—C2H5, methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl, ethenyl, propenyl, —O—CH3, —O—C2H5, —NH2, —N(CH3)2, —NH—CH3, —CH2-NH2, —O—CF3, —C(═O)—H, —C(═O)—O—CH3, —C(═O)—O—C2H5, phenyl, pyrrolyl, (1,3)-dioxolanyl, —Si(phenyl)2[C(CH3)3], —NO2, NH—S(═O)2-CH3, —NH—S(═O)2-C2H5, —S(═O)2-NH2, —S(═O)2-NH—CH3, —CH2-OH, —C(═O)—CH3, —C(═O)—OH, —CH2- O—CH3, —C(═O)—NH2, —C(═O)—NH—CH3, —NH—C(═O)—CH3, —S(═O)2-N(CH3)2, —NH—S(═O)2-OH and —NH—C(═NH)—NH2;

Very particular preference is given to substituted imidazo-3-yl-amine compounds of the general formula I,

embedded image

in which

A1 represents a C—R1a group, A2 represents a C—R1b group, A3 represents a C—R1c group and A4 represents a C—R1d group, or

A1 represents a nitrogen atom, A2 represents a C—R1b group, A3 represents a C—R1c group and A4 represents a C—R1d group, or

A1 represents a C—R1a group, A2 represents a nitrogen atom, A3 represents a C—R1c group and A4 represents a C—R1d group,

R1a, R1b, R1c, R1d, in each case mutually independently, represent a hydrogen; —OR16; —F; —Cl, —Br; —CF3, —CN; —S(═O)2-NH2; —C(═O)—OR12, an alkyl group selected from the group consisting of methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl and tert-butyl; a phenyl group; a benzyl group; a phenethyl group or a (3-phenyl)-prop-1-yl group,

or optionally R1a and R1b, together with the C—C bridge joining them together, form an unsubstituted anellated phenyl group;

or optionally R1c and R1d, together with the C—C bridge joining them together, form an unsubstituted anellated phenyl group;

R2 and R3, mutually independently, in each case represent a hydrogen; —C(═O)—R20; —(CH2)q-C(═O)—R21 with q=1; —(CH2)r-C(═O)—O—R23 with r=1; an alkyl group selected from the group consisting of methyl; ethyl; propyl; iso-propyl; n-butyl; tert-butyl; sec-butyl; iso-butyl; n-pentyl; n-hexyl; n-heptyl; n-octyl; (1,1,3,3)-tetramethyl-butyl; (1,1)-dimethyl-pentyl and (1,2)-dimethylbutyl; an unsubstituted cyclopentyl or cyclohexyl group, which may in each case be attached via a —(CH2), —(CH2)2 or —(CH2)3 group; or a phenyl, pyridinyl, thiophenyl or furanyl group, which is in each case unsubstituted or optionally substituted with 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, —CN, —CF3, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, —O—CH3 and —O—C2H5 and is optionally attached via a —(CH2), —(CH2)2, —(CH(CH3) or —(CH2)3 group,

or R2 and R3, together with the nitrogen atom joining them together as a ring member, form a heterocycloaliphatic group selected from the group consisting of pyrrolidinyl, piperidinyl, piperazinyl and morpholinyl,

R12 represents a hydrogen or an alkyl group selected from the group consisting of methyl, ethyl, n-propyl, iso-propyl and tert-butyl;

R16, R20, R21 and R23, in each case mutually independently represent an alkyl group selected from the group consisting of methyl, ethyl, n-propyl, iso-propyl and tert-butyl, or a phenyl group, which is in each case unsubstituted or substituted with 1 or 2 substituents mutually independently selected from the group consisting of F, Cl, Br, methyl, ethyl, —O—CH3 and —O—C2H5 and is optionally attached via a —(CH2) group,

M1 represents a group selected from the group consisting of groups 1 to 6, 21, 22, 36 and 37,

embedded image

M2 represents a group selected from the group consisting of phenyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 2-thiophenyl, 3-thiophenyl, 2-imidazolyl, 4-imidazolyl, 5-imidazolyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 5-quinolinyl, 6-quinolinyl, 7-quinolinyl and 8-quinolinyl, wherein the respective group is unsubstituted or optionally substituted with 1, 2, 3, 4 or 5 substituents, which are mutually independently selected from the group consisting of F, Cl, Br, —CN, —CF3, —SF5, —S—CH3, —S—C2H5, methyl, ethyl, iso-propyl, tert-butyl, ethenyl, propenyl, —OH, —O—CH3, —O—C2H5, —NH2, —N(CH3)2, —NH—CH3, —CH2-NH2, —NO2, —O—CF3, —C(═O)—H; —C(═O)—OCH3, —C(═O)—O—C2H5, phenyl, pyrrolyl, (1,3)-dioxolanyl, NH—S(═O)2-CH3, —NH—S(═O)2-C2H5, —S(═O)2-NH2, —S(═O)2-NH—CH3, - CH2-OH, —C(═O)—CH3, —C(═O)—OH, —CH213 O—CH3, —C(═O)—NH2, —C(═O)—NH—CH3, —NH—C(═O)—CH3, —NH—C(═NH)—NH2, —NH—S(═O)2-OH; —S(═O)2-N(CH3)2 and —Si(phenyl)2[C(CH3)3],

Very particularly preferred compounds are those of the general formula Id,

embedded image

in which R1a, R1c, R1d, R2 and R3 in each case have the above-stated meaning;

W1 represents C and W2 represents C

or W1 represents C and W2 represents N

or W1 represents N and W2 represents C; and

R30 and R31, mutually independently, in each case represent a group selected from the group consisting of H, F, Cl, Br, —CN, —CF3, —SF5, —S—CH3, —S—C2H5, methyl, ethyl, iso-propyl, tert-butyl, ethenyl, propenyl, —OH, —O—CH3, —O—C2H5, —NH2, —N(CH3)2, —NH—CH3, —CH2-NH2, —NO2, —O—CF3, —C(═O)—H; —C(═O)—OCH3, —C(═O)—O—C2H5, phenyl, pyrrolyl, (1,3)-dioxolanyl, —Si(phenyl)2[C(CH3)3], NH—S(═O)2-CH3, —NH—S(═O)2-C2H5, —S(═O)2-NH2, —S(═O)2-NH—CH3, —CH2-OH, —C(═O)—CH3, —C(═O)—OH, —CH2- O—CH3, —C(═O)—NH2, —C(═O)—NH—CH3, —NH—C(═O)—CH3, —NH—C(═NH)—NH2, —NH—S(═O)2-OH and —S(═O)2-N(CH3)2;

in each case optionally in the form of corresponding salts, or in each case optionally in the form of corresponding solvates.

Very particularly preferred compounds are those of the general formula Ie,

embedded image

in which R1a, R1b, R1c, R1d, R2 and R3 in each case have the above-stated meaning;

W1 represents C and W2 represents C

or W1 represents C and W2 represents N

or W1 represents N and W2 represents C; and

R30 and R31, mutually independently, in each case represent a group selected from the group consisting of H, F, Cl, Br, —CN, —CF3, —SF5, —S—CH3, —S—C2H5, methyl, ethyl, iso-propyl, tert-butyl, ethenyl, propenyl, —OH, —O—CH3, —O—C2H5, —NH2, —N(CH3)2, —NH—CH3, —CH2-NH2, —NO2, —O—CF3, —C(═O)—H; —C(═O)-OCH3, —C(═O)—O—C2H5, phenyl, pyrrolyl, (1,3)-dioxolanyl, —Si(phenyl)2 [C(CH3)3], NH—S(═O)2-CH3, —NH—S(═O)2-C2H5, —S(═O)2-NH2, —S(═O)2-NH—CH3, —CH2-OH, —C(═O)—CH3, —C(═O)—OH, —CH2- O—CH3, —C(═O)—NH2, —C(═O)—NH—CH3, —NH—C(═O)—CH3, —NH—C(═NH)—NH2, —NH—S(═O)2-OH and —S(═O)2-N(CH3)2;

in each case optionally in the form of corresponding salts, or in each case optionally in the form of corresponding solvates.

Very particularly preferred compounds are those of the general formula If,

embedded image

in which

R1a, R1c, R1d, R2 and R3 in each case have the above-stated meaning;

W1 represents C and W2 represents C

or W1 represents C and W2 represents N

or W1 represents N and W2 represents C;

W3 represents C—R32; W4 represents C—R33 and W5 represents C—R34;

or one of the groups W3, W4 and W5 represents N and the other two groups selected from the group consisting of W3, W4 and W5 represent C—R32 or C—R33;

and R32, R33, R34, R35 and R36, mutually independently, in each case represent a group selected from the group consisting of H, F, Cl, Br, —CN, —CF3, —SF5, —S—CH3, —S—C2H5, methyl, ethyl, iso-propyl, tert-butyl, ethenyl, propenyl, —OH, —O—CH3, —O—C2H5, —NH2, —N(CH3)2, —NH—CH3, —CH2-NH2, —NO2, —O—CF3, —C(═O)—H; —C(═O)—OCH3, —C(═O)—O—C2H5, phenyl, pyrrolyl, (1,3)-dioxolanyl, —Si(phenyl)2[C(CH3)3], NH—S(═O)2-CH3, —NH—S(═O)2-C2H5, —S(═O)2-NH2, —S(═O)2-NH—CH3, —CH2-OH, —C(═O)—CH3, —C(═O)—OH, —CH2- O—CH3, —C(═O)—NH2, —C(═O)—NH—CH3, —NH—C(═O)—CH3, —NH—C(═NH)—NH2, —NH—S(═O)2-OH and —S(═O)2-N(CH3)2;

in each case optionally in the form of corresponding salts, or in each case optionally in the form of corresponding solvates.

Very particularly preferred compounds are those of the general formula Ig,

embedded image

in which

R1a, R1b, R1c, R1d, R2 and R3 in each case have the above-stated meaning;

W1 represents C and W2 represents C

or W1 represents C and W2 represents N

or W1 represents N and W2 represents C;

W3 represents C—R32; W4 represents C—R33 and W5 represents C—R34;

or one of the groups W3, W4 and W5 represent N and the other two groups selected from the group consisting of W3, W4 and W5 represent C—R32 or C—R33;

and R32, R33, R34, R35 and R36, mutually independently, in each case represent a group selected from the group consisting of H, F, Cl, Br, —CN, —CF3, —SF5, —S—CH3, —S—C2H5, methyl, ethyl, iso-propyl, tert-butyl, ethenyl, propenyl, —OH, —O—CH3, —O—C2H5, —NH2, —N(CH3)2, —NH—CH3, —CH2-NH2, —NO2, —O—CF3, —C(═O)—H; —C(═O)—OCH3, —C(═O)—O—C2H5, phenyl, pyrrolyl, (1,3)-dioxolanyl, —Si(phenyl)2[C(CH3)3], NH—S(═O)2-CH3, —NH—S(═O)2-C2H5, —S(═O)2-NH2, S(═O)2-NH—CH3, —CH2-OH, —C(═O)—CH3, —C(═O)—OH, —CH2- O—CH3, —C(═O)—NH2, —C(═O)—NH—CH3, —NH—C(═O)—CH3, —NH—C(═NH)—NH2, —NH—S(═O)2-OH and —S(═O)2-N(CH3)2;

in each case optionally in the form of corresponding salts, or in each case optionally in the form of corresponding solvates.

Very particularly preferred compounds are those of the general formula Ih,

embedded image

in which

R1a, R1c, R1d, R2 and R3 in each case have the above-stated meaning;

W6 represents C or N; and

R30 and R31, mutually independently, in each case represent a group selected from the group consisting of H, F, Cl, Br, —CN, —CF3, —SF5, —S—CH3, —S—C2H5, methyl, ethyl, iso-propyl, tert-butyl, ethenyl, propenyl, —OH, —O—CH3, —O—C2H5, —NH2, —N(CH3)2, —NH—CH3, —CH2-NH2, —NO2, —O—CF3, —C(═O)—H; —C(═O)—OCH3, —C(═O)—O—C2H5, phenyl, pyrrolyl, (1,3)-dioxolanyl, —Si(phenyl)2[C(CH3)3], NH—S(═O)2-CH3, —NH—S(═O)2-C2H5, —S(═O)2-NH2, —S(═O)2-NH—CH3, —CH2-OH, —C(═O)—CH3, —C(═O)—OH, —CH2-O—CH3, —C(═O)—NH2, —C(═O)—NH—CH3, —NH—C(═O)—CH3, —NH—C(═NH)—NH2, —NH—S(═O)2-OH and —S(═O)2-N(CH3)2;

in each case optionally in the form of corresponding salts, or in each case optionally in the form of corresponding solvates.

Very particularly preferred compounds are those of the general formula Ik,

embedded image

in which

R1a, R1b, R1c, R1d, R2 and R3 in each case have the above-stated meaning;

W6 represents C or N; and

R30 and R31, mutually independently, in each case represent a group selected from the group consisting of H, F, Cl, Br, —CN, —CF3, —SF5, —S—CH3, —S—C2H5, methyl, ethyl, iso-propyl, tert-butyl, ethenyl, propenyl, —OH, —O—CH3, —O—C2H5, —NH2, —N(CH3)2, —NH—CH3, —CH2-NH2, —NO2, —O—CF3, —C(═O)—H; —C(═O)—OCH3, —C(═O)—O—C2H5, phenyl, pyrrolyl, (1,3)-dioxolanyl, —Si(phenyl)2[C(CH3)3], NH—S(═O)2-CH3, —NH—S(═O)2-C2H5, —S(═O)2-NH2, —S(═O)2-NH—CH3, —CH2-OH, —C(═O)—CH3, —C(═O)—OH, —CH2-O—CH3, —C(═O)—NH2, —C(═O)—NH—CH3, —NH—C(═O)—CH3, —NH—C(═NH)—NH2, —NH—S(═O)2-OH and —S(═O)2-N(CH3)2;

in each case optionally in the form of corresponding salts, or in each case optionally in the form of corresponding solvates.

Very particularly preferred compounds are those of the general formula Im,

embedded image

in which

R1a, R1c, R1d, R2 and R3 in each case have the meaning according to claim 14;

W6 represents C or N;

W3 represents C—R32; W4 represents C—R33 and W5 represents C—R34;

or one of the groups W3, W4 and W5 represents N and the other two groups selected from the group consisting of W3, W4 and W5 represent C—R32 or C—R33;

in each case optionally in the form of corresponding salts, or in each case optionally in the form of corresponding solvates.

Very particularly preferred compounds are those of the general formula In,

embedded image

in which

R1a, R1b, R1c, R1d, R2 and R3 in each case have the above-stated meaning;

W6 represents C or N;

W3 represents C—R32; W4 represents C—R33 and W5 represents C—R34;

or one of the groups W3, W4 and W5 represent N and the other two groups selected from the group consisting of W3, W4 and W5 represent C—R32 or C—R33;

and R32, R33, R34, R35 and R36, mutually independently, in each case represents a group selected from the group consisting of H, F, Cl, Br, —CN, —CF3, —SF5, —S—CH3, —S—C2H5, methyl, ethyl, iso-propyl, tert-butyl, ethenyl, propenyl, —OH, —O—CH3, —O—C2H5, —NH2, —N(CH3)2, —NH—CH3, —CH2-NH2, —NO2, —O—CF3, —C(═O)—H; —C(═O)—OCH3, —C(═O)—O—C2H5, phenyl, pyrrolyl, (1,3)-dioxolanyl, —Si(phenyl)2[C(CH3)3], NH—S(═O)2-CH3, —NH—S(═O)2-C2H5, —S(═O)2-NH2, S(═O)2-NH—CH3, —CH2-OH, —C(═O)—CH3, —C(═O)—OH, —CH2- O—CH3, —C(═O)—NH2, —C(═O)—NH—CH3, —NH—C(═O)—CH3, —NH—C(═NH)—NH2, —NH—S(═O)2-OH and —S(═O)2-N(CH3)2;

in each case optionally in the form of corresponding salts, or in each case optionally in the form of corresponding solvates.

Still more preferred substituted imidazo-3-yl-amine compounds of the above general formula I are those selected from the group consisting of

[1] cyclopentyl-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine,
[2] cyclohexylmethyl-[5-methyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-amine,
[3] cyclohexylmethyl-[6-methyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-amine,
[4] cyclohexylmethyl-[7-methyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-amine,
[5] cyclohexylmethyl-[8-methyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-amine,
[6] cyclohexylmethyl-[5,7-dimethyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-amine,
[7] [8-benzyloxy-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-cyclohexylmethyl-amine,
[8] cyclohexylmethyl-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine,
[9] cyclohexylmethyl-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrimidin-3-yl]-amine,
[10] (4-methoxy-benzyl)-[5-methyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-amine,
[11] (4-methoxy-benzyl)-[6-methyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-amine,
[12] (4-methoxy-benzyl)-[7-methyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-amine,
[13] (4-methoxy-benzyl)-[8-methyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-amine,
[14] [5,7-dimethyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(4-methoxy-benzyl)-amine,
[15] [8-benzyloxy-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(4-methoxy-benzyl)-amine,
[16] (4-methoxy-benzyl)-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-amine,
[17] (4-methoxy-benzyl)-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine,
[18] tert-butyl-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine,
[19] tert-butyl-[6-methyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-amine,
[20] [8-benzyloxy-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(3-methoxy-phenyl)-amine,
[21] (3-methoxy-benzyl)-[5-methyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-amine,
[22] (3-methoxy-benzyl)-[8-methyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-amine,
[23] [5,7-dimethyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(3-methoxy-benzyl)-amine,
[24] [8-benzyloxy-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(3-methoxy-benzyl)-amine,
[25] (3-methoxy-benzyl)-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-amine,
[26] (3-methoxy-benzyl)-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine,
[27] [6-methyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(1-phenyl-ethyl)-amine,
[28] [7-methyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(1-phenyl-ethyl)-amine,
[29] [5,7-dimethyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(1-phenyl-ethyl)-amine,
[30] [8-benzyloxy-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(1-phenyl-ethyl)-amine,
[31] (1-phenyl-ethyl)-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine,
[32] (2-chloro-benzyl)-[5,7-dimethyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-amine,
[33] (3-chloro-4-fluoro-phenyl)-[7-phenyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-amine,
[34] (4-methoxy-benzyl)-[7-methyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrimidin-3-yl]-amine,
[35] [8-methyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(1-phenyl-ethyl)-amine,
[36] [7-methyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrimidin-3-yl]-(1-phenyl-ethyl)-amine,
[37] (2-methoxy-benzyl)-[7-methyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-amine,
[38] (2-methoxy-benzyl)-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-amine,
[39] (2-chloro-benzyl)-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-amine,
[40] (2-methoxy-benzyl)-[7-methyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrimidin-3-yl]-amine,
[41] (3-methoxy-phenyl)-[6-methyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-amine,
[42] [5,7-dimethyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(3-methoxy-phenyl)-amine,
[43] (3-methoxy-phenyl)-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine,
[44] [7-ethyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(2-methoxy-benzyl)-amine,
[45] (2-chloro-benzyl)-[7-ethyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-amine,
[46] [7-tert-butyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(3-chloro-4-fluoro-phenyl)-amine,
[47] (3-methoxy-benzyl)-[7-methyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrimidin-3-yl]-amine,
[48] [7-ethyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(2-fluoro-phenyl)-amine,
[49] [7-tert-butyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(2-fluoro-phenyl)-amine,
[50] (2,4-difluoro-phenyl)-[2-(5-phenylethynyl-thiophen-2-yl)-7-(3-phenyl-propyl)-imidazo[1,2-a]pyridin-3-yl]-amine,
[51] (4-fluoro-benzyl)-[7-methyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-amine,
[52] [5,7-dimethyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(4-fluoro-benzyl)-amine,
[53] [7-ethyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(3-trifluoromethyl-benzyl)-amine,
[54] [7-isopropyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(3-trifluoromethyl-benzyl)-amine,
[55] tert-butyl-[2-(4-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine,
[56] [2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-(1,1,3,3-tetramethyl-butyl)-amine,
[57] butyl-[2-(4-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine,
[59] [2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(1,1,3,3-tetramethyl-butyl)-amine,
[60] [2-(5-pyridinyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-(1,1,3,3-tetramethyl-butyl)-amine,
[61] [2-(5-pyridin-4-ylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-(1,1,3,3-tetramethyl-butyl)-amine,
[62] [6-chloro-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(1,1,3,3-tetramethyl-butyl)-amine,
[63] [6,8-dichloro-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(1,1,3,3-tetramethyl-butyl)-amine,
[64] [2-(5-pyridin-2-ylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-(1,1,3,3-tetramethyl-butyl)-amine,
[65] dimethyl-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine,
[66] methyl-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine,
[67] N-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-acetamide,
[68] ethyl-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine,
[69] propyl-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine,
[70] butyl-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine,
[71] (2-methylpropyl)-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine,
[72] pentyl-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine,
[73] {(methoxycarbonylmethyl)-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amino}-acetic acid methyl ester,
[74] benzyl-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine,
[75] [2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-ylamino]-acetic acid methyl ester,
[76] tert-butyl-[2-(5-pyridin-4-ylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine,
[77] tert-butyl-[2-(5-pyridin-2-ylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine,
[78] N-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-benzamide,
[79] [2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-bis-pyridin-3-ylmethyl-amine,
[80] 2,2-dimethyl-N-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-propionamide,
[81] 3-methoxy-N-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-benzamide,
[82] tert-butyl-[2-(5-pyridin-3-ylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine
[83] 2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-ylamine
[84] methyl-2-(5-(phenylethynyl)thiophen-2-yl)-3-(2,4,4-trimethylpentan-2-ylamino)imidazo[1,2-a]pyrazine-8-carboxylate
[85] 2-(5-(phenylethynyl)thiophen-2-yl)-N-(2,4,4-trimethylpentan-2-yl)imidazo[1,2-a]pyrimidin-3-amine
[86] 2-(5-((6-methylpyridin-2-yl)ethynyl)thiophen-2-yl)-N-(2,4,4-trimethylpentan-2-yl)imidazo[1,2-a]pyrazin-3-amine
[87] N-cyclohexyl-2-(5-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine
[88] 2-(5-(phenylethynyl)thiophen-2-yl)-3-(piperidin-1-yl)imidazo[1,2-a]pyrazine
[89] N-tert-butyl-N-methyl-2-(5-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine
[90] methyl-2-(5-(phenylethynyl)thiophen-2-yl)-3-(2,4,4-trimethylpentan-2-ylamino)imidazo[1,2-a]pyridine-6-carboxylate
[91] N-tert-butyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride
[92] 8-bromo-N-cyclopentyl-6-methyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine
[93] N,N-diethyl-2-(5-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine
[94] N-tert-butyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine
[95] N-tert-butyl-2-(5-(phenylethynyl)furan-2-yl)imidazo[1,2-a]pyrazin-3-amine
[96] 8-bromo-N-tert-butyl-6-methyl-2-(3-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyridin-3-amine
[97] N-tert-butyl-8-methyl-2-(5-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine
[98] N-methyl-2-(5-(phenylethynyl)thiophen-2-yl)-N-(2,4,4-trimethylpentan-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride
[99] 2-(5-(phenylethynyl)thiophen-2-yl)-3-(pyrrolidin-1-yl)imidazo[1,2-a]pyrazine hydrochloride
[100] N-tert-butyl-2-(5-((4-fluorophenyl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride
[101] N-tert-butyl-7-methyl-2-(5-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine
[102] N-tert-butyl-5-methyl-2-(5-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine
[103] 8-chloro-2-(3-(pyridin-2-ylethynyl)phenyl)-6-(trifluoromethyl)-N-(2,4,4-trimethylpentan-2-yl)imidazo[1,2-a]pyridin-3-amine
[104] N-tert-butyl-2-(5-((3-fluorophenyl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride
[105] N-tert-butyl-2-(5-((2-fluorophenyl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride
[106] methyl-3-(tert-butylamino)-2-(5-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazine-8-carboxylate
[107] N-tert-butyl-2-(5-(pyrazin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine
[108] 2-(5-((4-aminophenyl)ethynyl)thiophen-2-yl)-N-tert-butylimidazo[1,2-a]pyrazin-3-amine
[109] N-isopropyl-2-(5-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine
[110] N-tert-butyl-2-(5-(thiophen-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride
[111] N-tert-butyl-2-(3-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyrazin-3-amine
[112] N-tert-butyl-2-(5-((2-methoxyphenyl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride
[113] N-tert-butyl-2-(5-((3-methoxyphenyl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride
[114] N-tert-butyl-2-(5-((4-methoxyphenyl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride
[115] N-tert-butyl-2-(5-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]quinolin-1-amine
[116] N-tert-butyl-2-(4-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyrazin-3-amine
[117] N-tert-butyl-2-(3-((6-methylpyridin-2-yl)ethynyl)phenyl)imidazo[1,2-a]pyrazin-3-amine
[118] N-tert-butyl-2-(2-methyl-6-(phenylethynyl)pyridin-3-yl)imidazo[1,2-a]pyrazin-3-amine
[119] N-tert-butyl-2-(5-(pyridin-2-ylethynyl)furan-2-yl)imidazo[1,2-a]pyrazin-3-amine
[120] 3-(tert-butylamino)-2-(5-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazine-8-carboxylic acid
[121] 4-((5-(3-(tert-butylamino)imidazo[1,2-a]pyrazin-2-yl)thiophen-2-yl)ethynyl)phenol hydrochloride
[122] 3-((5-(3-(tert-butylamino)imidazo[1,2-a]pyrazin-2-yl)thiophen-2-yl)ethynyl)phenol
[123] 2-(5-((3-aminophenyl)ethynyl)thiophen-2-yl)-N-tert-butylimidazo[1,2-a]pyrazin-3-amine hydrochloride
[124] 2-(5-((2-aminophenyl)ethynyl)thiophen-2-yl)-N-tert-butylimidazo[1,2-a]pyrazin-3-amine hydrochloride
[125] N-tert-butyl-2-(5-(phenylethynyl)thiophen-2-yl)imidazo[2,1-a]isoquinolin-3-amine
[126] N-tert-butyl-2-(6-(phenylethynyl)pyridin-3-yl)imidazo[1,2-a]pyrazin-3-amine
[127] N-tert-butyl-2-(5-(pyridin-4-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride
[128] 2-(5-((6-aminopyridin-3-yl)ethynyl)thiophen-2-yl)-N-tert-butylimidazo[1,2-a]pyrazin-3-amine hydrochloride
[129] N-tert-butyl-2-(5-(pyrimidin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride
[130] N-tert-butyl-2-(5-((4-methylpyridin-2-yl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride
[131] N-tert-butyl-2-(5-((5-methylpyridin-2-yl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride
[132] N-tert-butyl-2-(5-(pyridin-4-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine hydrochloride
[133] N-tert-butyl-2-(5-(thiazol-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine
[134] 2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride
[135] N-tert-butyl-2-(5-((5-methylthiophen-2-yl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride
[136] 2-(5-((6-aminopyridin-2-yl)ethynyl)thiophen-2-yl)-N-tert-butylimidazo[1,2-a]pyrazin-3-amine hydrochloride
[137] N-tert-butyl-2-(5-((3-methylthiophen-2-yl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine
[138] N-tert-butyl-2-(4-(phenylethynyl)thiazol-2-yl)imidazo[1,2-a]pyrazin-3-amine
[139] N-tert-butyl-2-(5-(m-tolylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine
[140] 3-((5-(3-(tert-butylamino)imidazo[1,2-a]pyrazin-2-yl)thiophen-2-yl)ethynyl)benzonitrile hydrochloride
[141] N-tert-butyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrimidin-3-amine
[142] N-tert-butyl-2-(6-(phenylethynyl)pyridin-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride
[143] N-tert-butyl-N-methyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine
[144] 4-((5-(3-(tert-butylamino)imidazo[1,2-a]pyrazin-2-yl)thiophen-2-yl)ethynyl)benzonitrile hydrochloride
[145] 2-(5-((1H-indol-6-yl)ethynyl)thiophen-2-yl)-N-tert-butylimidazo[1,2-a]pyrazin-3-amine hydrochloride
[146] N-tert-butyl-2-(2-(phenylethynyl)thiazol-5-yl)imidazo[1,2-a]pyrazin-3-amine
[147] N-tert-butyl-2-(5-(quinolin-6-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride
[148] 2-(5-((3-(1H-pyrrol-1-yl)phenyl)ethynyl)thiophen-2-yl)-N-tert-butylimidazo[1,2-a]pyrazin-3-amine hydrochloride
[149] 2-(5-((1H-indol-4-yl)ethynyl)thiophen-2-yl)-N-tert-butylimidazo[1,2-a]pyrazin-3-amine hydrochloride
[150] N-tert-butyl-2-(5-((3-nitrophenyl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride
[151] N-tert-butyl-2-(5-((4-nitrophenyl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride
[152] N-tert-butyl-2-(5-(thiazol-4-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride
[153] 2-((5-(3-(tert-butylamino)imidazo[1,2-a]pyrazin-2-yl)thiophen-2-yl)ethynyl)phenol
[154] 2-(5-((3-(aminomethyl)phenyl)ethynyl)thiophen-2-yl)-N-tert-butylimidazo[1,2-a]pyrazin-3-amine
[155] 2-(5-(biphenyl-3-ylethynyl)thiophen-2-yl)-N-tert-butylimidazo[1,2-a]pyrazin-3-amine hydrochloride
[156] N-tert-butyl-2-(5-(thiophen-3-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride
[157] N-tert-butyl-2-(5-((3-(dimethylamino)phenyl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride
[158] N-tert-butyl-2-(5-((6-methylpyridin-2-yl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride
[159] N-tert-butyl-2-(5-((3-fluoropyridin-2-yl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride
[160] N-tert-butyl-2-(5-((3-(methylamino)phenyl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride
[161] N-tert-butyl-2-(5-(p-tolylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine
[162] N-tert-butyl-2-(5-(o-tolylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride
[163] N-tert-butyl-2-(4-methyl-5-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride
[164] N-tert-butyl-2-(4-methyl-5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride
[165] N-tert-butyl-2-(5-((6-fluoropyridin-2-yl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine
[166] N-tert-butyl-2-(5-((2-nitrophenyl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine
[167] N-tert-butyl-8-chloro-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine
[168] N-tert-butyl-2-(5-((6-methoxypyridin-2-yl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine
[169] N-tert-butyl-2-(5-((5-fluoropyridin-2-yl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride
[170] 2-(4-(3-(tert-butylamino)imidazo[1,2-a]pyrazin-2-yl)-2-(phenylethynyl)phenyl)acetonitrile
[171] N-tert-butyl-2-(5-((5-methoxypyridin-3-yl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride
[172] 5-((5-(3-(tert-butylamino)imidazo[1,2-a]pyrazin-2-yl)thiophen-2-yl)ethynyl)nicotinonitrile hydrochloride
[173] N-tert-butyl-2-(5-((3-(methylthio)phenyl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine
[174] methyl-3-((5-(3-(tert-butylamino)imidazo[1,2-a]pyrazin-2-yl)thiophen-2-yl)ethynyl)benzoate
[175] N-tert-butyl-2-(5-((3,5-difluoropyridin-2-yl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine
[176] N-tert-butyl-2-(5-(phenylethynyl)thiazol-2-yl)imidazo[1,2-a]pyrazin-3-amine
[177] N-tert-butyl-2-(2-(pyridin-4-ylethynyl)thiazol-5-yl)imidazo[1,2-a]pyrazin-3-amine
[178] 3-((5-(3-(tert-butylamino)imidazo[1,2-a]pyrazin-2-yl)thiophen-2-yl)ethynyl)benzaldehyde
[179] 3-((5-(3-(tert-butylamino)imidazo[1,2-a]pyrazin-2-yl)thiophen-2-yl)ethynyl)-4-fluorobenzonitrile
[180] N-tert-butyl-2-(5-((3-(trifluoromethyl)phenyl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride
[181] N-tert-butyl-2-(2-(pyridin-2-ylethynyl)thiazol-5-yl)imidazo[1,2-a]pyrazin-3-amine
[182] N-tert-butyl-2-(3-methyl-5-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride
[183] N-tert-butyl-2-(3-methyl-5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride
[184] N-tert-butyl-2-(5-((3-vinylphenyl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine
[185] 2-(5-((1H-imidazol-4-yl)ethynyl)thiophen-2-yl)-N-tert-butylimidazo[1,2-a]pyrazin-3-amine hydrochloride
[186] N-tert-butyl-2-(5-((3-methylpyridin-2-yl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine
[187] N,N-dimethyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine
[188] N-tert-butyl-2-(5-((2-(tert-butyldiphenylsilyl)thiazol-5-yl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine
[189] 3-((5-(3-(tert-butylamino)imidazo[1,2-a]pyridin-2-yl)thiophen-2-yl)ethynyl)benzonitrile
[190] N-tert-butyl-2-(5-(phenylethynyl)thiazol-2-yl)imidazo[1,2-a]pyridin-3-amine
[191] N-tert-butyl-2-(5-(thiazol-5-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine
[192] N-tert-butyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine hydrochloride
[321] 6-chloro-N-cyclohexyl-2-(3-((6-methylpyridin-2-yl)ethynyl)phenyl)imidazo[1,2-a]pyridin-3-amine
[194] 5,7-dimethyl-N-phenethyl-2-(5-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrimidin-3-amine
[195] N-(3-methoxyphenethyl)-5,7-dimethyl-2-(5-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrimidin-3-amine
[196] N-(3-methoxyphenethyl)-5,7-dimethyl-2-(4-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrimidin-3-amine
[197] N-(3-methoxyphenethyl)-5,7-dimethyl-2-(5-(phenylethynyl)furan-2-yl)imidazo[1,2-a]pyrimidin-3-amine
[198] N-(4-chlorobenzyl)-8-methyl-2-(5-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine
[199] N-(3-methoxyphenethyl)-5-methyl-2-(4-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine
[200] N-(2-methylhexan-2-yl)-2-(4-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine
[201] N-phenethyl-2-(4-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine
[202] N-(3-methoxyphenethyl)-2-(4-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine
[203] 2-(4-(phenylethynyl)thiophen-2-yl)-N-(2-(thiophen-2-yl)ethyl)imidazo[1,2-a]pyrazin-3-amine
[204] N-(4-chlorobenzyl)-2-(5-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine
[205] N-(2-methylpentan-2-yl)-2-(5-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine
[206] N-(cyclohexylmethyl)-2-(4-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine
[207] N-(2-methoxybenzyl)-2-(5-(phenylethynyl)furan-2-yl)imidazo[1,2-a]pyrazin-3-amine
[208] N-(cyclohexylmethyl)-2-(4-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine
[209] N-(2-methylpentan-2-yl)-2-(4-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine
[210] 8-bromo-6-methyl-2-(3-((6-methylpyridin-2-yl)ethynyl)phenyl)-N-(2,4,4-trimethylpentan-2-yl)imidazo[1,2-a]pyridin-3-amine
[211] 8-bromo-N-cyclopentyl-6-methyl-2-(3-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyridin-3-amine
[212] N-cyclopentyl-2-(4-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine
[213] N-(1-phenylethyl)-2-(4-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine
[214] N-(2-methylpentan-2-yl)-2-(4-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine
[215] 8-bromo-N-cyclohexyl-6-methyl-2-(5-(pyridin-2-ylethynyl)furan-2-yl)imidazo[1,2-a]pyridin-3-amine
[216] N-cyclopentyl-2-(5-(phenylethynyl)furan-2-yl)imidazo[1,2-a]pyrazin-3-amine
[217] N-(3-methoxyphenethyl)-7-methyl-2-(4-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrimidin-3-amine
[218] 8-(benzyloxy)-2-(5-(phenylethynyl)thiophen-2-yl)-N-(2,4,4-trimethylpentan-2-yl)imidazo[1,2-a]pyridin-3-amine
[219] 8-(benzyloxy)-N-cyclopentyl-2-(4-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine
[220] 8-(benzyloxy)-N-(2-methylpentan-2-yl)-2-(4-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine
[221] 6-chloro-N-(4-fluorobenzyl)-2-(5-(phenylethynyl)furan-2-yl)imidazo[1,2-a]pyridin-3-amine
[222] 6-bromo-N-butyl-5-methyl-2-(4-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine
[223] N-(furan-2-yl)-8-methyl-2-(5-(phenylethynyl)furan-2-yl)imidazo[1,2-a]pyridin-3-amine
[224] N-(furan-2-yl)-2-(5-(phenylethynyl)furan-2-yl)imidazo[1,2-a]pyridin-3-amine
[225] N-(furan-2-yl)-2-(5-(phenylethynyl)furan-2-yl)-7-propylimidazo[1,2-a]pyridin-3-amine
[226] 5,7-dimethyl-2-(4-(phenylethynyl)thiophen-2-yl)-N-(3-(trifluoromethyl)phenyl)imidazo[1,2-a]pyrimidin-3-amine
[227] 6-bromo-N-(4-chlorophenethyl)-8-methyl-2-(4-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine
[228] N-(4-chlorophenethyl)-7-phenyl-2-(4-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine
[229] N-phenethyl-7-phenyl-2-(4-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine
[230] N-(4-chlorobenzyl)-5,7-dimethyl-2-(4-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine
[231] 6-bromo-N-(4-chlorobenzyl)-5-methyl-2-(4-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine
[232] 8-bromo-N-(4-chlorobenzyl)-6-methyl-2-(4-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine
[233] N-(3-methoxyphenethyl)-2-(4-(phenylethynyl)thiophen-2-yl)-5-propylimidazo[1,2-a]pyridin-3-amine
[234] 6-bromo-8-methyl-2-(4-(phenylethynyl)thiophen-2-yl)-N-(2-(thiophen-2-yl)ethyl)imidazo[1,2-a]pyridin-3-amine
[235] 7-phenyl-2-(4-(phenylethynyl)thiophen-2-yl)-N-(2-(thiophen-2-yl)ethyl)imidazo[1,2-a]pyridin-3-amine
[236] 6,8-dibromo-N-(2-methylpentan-2-yl)-2-(5-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine
[237] 6-bromo-N-(2,6-dimethylphenyl)-8-methyl-2-(4-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine
[238] N-cyclohexyl-2-(3-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyrazin-3-amine
[239] 2-(3-(pyridin-2-ylethynyl)phenyl)-N-(2,4,4-trimethylpentan-2-yl)imidazo[1,2-a]pyrazin-3-amine
[240] N-cyclopentyl-2-(4-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyrazin-3-amine
[241] 8-chloro-2-(4-(pyridin-2-ylethynyl)phenyl)-6-(trifluoromethyl)-N-(2,4,4-trimethylpentan-2-yl)imidazo[1,2-a]pyridin-3-amine
[242] N-(4-fluorophenyl)-2-(4-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyrazin-3-amine
[243] N-cyclopentyl-2-(2-methyl-6-(phenylethynyl)pyridin-3-yl)imidazo[1,2-a]pyrazin-3-amine
[244] N-cyclohexyl-2-(2-methyl-6-(phenylethynyl)pyridin-3-yl)imidazo[1,2-a]pyrazin-3-amine
[245] N-cyclopentyl-2-(5-(pyridin-2-ylethynyl)furan-2-yl)imidazo[1,2-a]pyrazin-3-amine
[246] 8-bromo-N-cyclopentyl-6-methyl-2-(5-(pyridin-2-ylethynyl)furan-2-yl)imidazo[1,2-a]pyridin-3-amine
[247] N-cyclohexyl-2-(5-(pyridin-2-ylethynyl)furan-2-yl)imidazo[1,2-a]pyrazin-3-amine
[248] 2-(5-(pyridin-2-ylethynyl)furan-2-yl)-N-(2,4,4-trimethylpentan-2-yl)imidazo[1,2-a]pyrazin-3-amine
[249] N-cyclopentyl-2-(3-((6-methylpyridin-2-yl)ethynyl)phenyl)imidazo[1,2-a]pyrazin-3-amine
[250] 8-bromo-N-cyclopentyl-6-methyl-2-(4-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyridin-3-amine
[251] N-cyclohexyl-2-(3-((6-methylpyridin-2-yl)ethynyl)phenyl)imidazo[1,2-a]pyrazin-3-amine
[252] N-(4-fluorophenyl)-2-(3-((6-methylpyridin-2-yl)ethynyl)phenyl)imidazo[1,2-a]pyrazin-3-amine
[253] 2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)-N-(2,4,4-trimethylpentan-2-yl)imidazo[1,2-a]pyrimidin-3-amine
[254] N-cyclohexyl-2-(3-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyrimidin-3-amine
[255] 2-(3-(pyridin-2-ylethynyl)phenyl)-N-(2,4,4-trimethylpentan-2-yl)imidazo[1,2-a]pyrimidin-3-amine
[256] 2-(6-(phenylethynyl)pyridin-3-yl)-N-(2,4,4-trimethylpentan-2-yl)imidazo[1,2-a]pyrimidin-3-amine
[257] N-cyclopentyl-2-(5-(pyridin-2-ylethynyl)furan-2-yl)imidazo[1,2-a]pyrimidin-3-amine
[258] N-tert-butyl-2-(5-(pyridin-2-ylethynyl)furan-2-yl)imidazo[1,2-a]pyrimidin-3-amine
[259] N-cyclopentyl-2-(3-((6-methylpyridin-2-yl)ethynyl)phenyl)imidazo[1,2-a]pyrimidin-3-amine
[260] N-cyclopentyl-2-(3-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyridin-3-amine
[261] N-tert-butyl-2-(3-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyridin-3-amine
[262] 2-(3-(pyridin-2-ylethynyl)phenyl)-N-(2,4,4-trimethylpentan-2-yl)imidazo[1,2-a]pyridin-3-amine
[263] N-(4-fluorophenyl)-2-(3-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyridin-3-amine
[264] N-tert-butyl-2-(4-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyridin-3-amine
[265] N-cyclopentyl-2-(2-methyl-6-(phenylethynyl)pyridin-3-yl)imidazo[1,2-a]pyridin-3-amine
[266] N-(4-fluorophenyl)-2-(2-methyl-6-(phenylethynyl)pyridin-3-yl)imidazo[1,2-a]pyridin-3-amine
[267] N-cyclopentyl-6-methyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine
[268] N-tert-butyl-6-methyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine
[269] N-cyclohexyl-6-methyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine
[270] 6-methyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)-N-(2,4,4-trimethylpentan-2-yl)imidazo[1,2-a]pyridin-3-amine
[271] 6-methyl-2-(2-methyl-6-(phenylethynyl)pyridin-3-yl)-N-(2,4,4-trimethylpentan-2-yl)imidazo[1,2-a]pyridin-3-amine
[272] N-cyclopentyl-6-methyl-2-(5-(pyridin-2-ylethynyl)furan-2-yl)imidazo[1,2-a]pyridin-3-amine
[273] N-cyclohexyl-6-methyl-2-(3-((6-methylpyridin-2-yl)ethynyl)phenyl)imidazo[1,2-a]pyridin-3-amine
[274] N-cyclohexyl-7-methyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine
[275] 7-methyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)-N-(2,4,4-trimethylpentan-2-yl)imidazo[1,2-a]pyridin-3-amine
[276] N-tert-butyl-7-methyl-2-(3-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyridin-3-amine
[277] N-(4-fluorophenyl)-7-methyl-2-(3-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyridin-3-amine
[278] N-tert-butyl-7-methyl-2-(4-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyridin-3-amine
[279] N-(4-fluorophenyl)-7-methyl-2-(5-(pyridin-2-ylethynyl)furan-2-yl)imidazo[1,2-a]pyridin-3-amine
[280] N-cyclohexyl-8-methyl-2-(6-(phenylethynyl)pyridin-3-yl)imidazo[1,2-a]pyridin-3-amine
[281] N-cyclopentyl-2-(6-(phenylethynyl)pyridin-3-yl)imidazo[1,2-a]pyridin-3-amine
[282] N-tert-butyl-2-(6-(phenylethynyl)pyridin-3-yl)imidazo[1,2-a]pyridin-3-amine
[283] N-cyclohexyl-2-(6-(phenylethynyl)pyridin-3-yl)imidazo[1,2-a]pyridin-3-amine
[284] 2-(6-(phenylethynyl)pyridin-3-yl)-N-(2,4,4-trimethylpentan-2-yl)imidazo[1,2-a]pyridin-3-amine
[285] N-tert-butyl-2-(5-(pyridin-2-ylethynyl)furan-2-yl)imidazo[1,2-a]pyridin-3-amine
[286] N-cyclohexyl-2-(5-(pyridin-2-ylethynyl)furan-2-yl)imidazo[1,2-a]pyridin-3-amine
[287] N-(4-fluorophenyl)-2-(5-(pyridin-2-ylethynyl)furan-2-yl)imidazo[1,2-a]pyridin-3-amine
[288] N-cyclohexyl-2-(3-((6-methylpyridin-2-yl)ethynyl)phenyl)imidazo[1,2-a]pyridin-3-amine
[289] 2-(3-((6-methylpyridin-2-yl)ethynyl)phenyl)-N-(2,4,4-trimethylpentan-2-yl)imidazo[1,2-a]pyridin-3-amine
[290] N-tert-butyl-5-methyl-2-(3-((6-methylpyridin-2-yl)ethynyl)phenyl)imidazo[1,2-a]pyridin-3-amine
[291] 5-methyl-2-(3-((6-methylpyridin-2-yl)ethynyl)phenyl)-N-(2,4,4-trimethylpentan-2-yl)imidazo[1,2-a]pyridin-3-amine
[292] N-cyclohexyl-5,7-dimethyl-2-(3-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyrimidin-3-amine
[293] N-cyclohexyl-5,7-dimethyl-2-(2-methyl-6-(phenylethynyl)pyridin-3-yl)imidazo[1,2-a]pyrimidin-3-amine
[294] N-cyclopentyl-5,7-dimethyl-2-(5-(pyridin-2-ylethynyl)furan-2-yl)imidazo[1,2-a]pyrimidin-3-amine
[295] N-tert-butyl-5,7-dimethyl-2-(5-(pyridin-2-ylethynyl)furan-2-yl)imidazo[1,2-a]pyrimidin-3-amine
[296] N-(4-fluorophenyl)-8-methyl-2-(3-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyridin-3-amine
[297] N-cyclohexyl-8-methyl-2-(4-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyridin-3-amine
[298] N-cyclohexyl-7-ethyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine
[299] 7-ethyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)-N-(2,4,4-trimethylpentan-2-yl)imidazo[1,2-a]pyridin-3-amine
[300] N-cyclohexyl-7-ethyl-2-(3-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyridin-3-amine
[301] N-cyclopentyl-7-ethyl-2-(4-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyridin-3-amine
[302] N-cyclopentyl-7-ethyl-2-(6-(phenylethynyl)pyridin-3-yl)imidazo[1,2-a]pyridin-3-amine
[303] N-tert-butyl-7-ethyl-2-(6-(phenylethynyl)pyridin-3-yl)imidazo[1,2-a]pyridin-3-amine
[304] N-tert-butyl-7-ethyl-2-(5-(pyridin-2-ylethynyl)furan-2-yl)imidazo[1,2-a]pyridin-3-amine
[305] 7-isopropyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)-N-(2,4,4-trimethylpentan-2-yl)imidazo[1,2-a]pyridin-3-amine
[306] N-tert-butyl-7-isopropyl-2-(3-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyridin-3-amine
[307] N-tert-butyl-7-isopropyl-2-(4-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyridin-3-amine
[308] N-cyclohexyl-7-isopropyl-2-(5-(pyridin-2-ylethynyl)furan-2-yl)imidazo[1,2-a]pyridin-3-amine
[309] N-tert-butyl-7-isopropyl-2-(3-((6-methylpyridin-2-yl)ethynyl)phenyl)imidazo[1,2-a]pyridin-3-amine
[310] 6-chloro-N-cyclopentyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine
[311] N-tert-butyl-6-chloro-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine
[312] 6-chloro-N-cyclohexyl-2-(3-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyridin-3-amine
[313] 6-chloro-2-(3-(pyridin-2-ylethynyl)phenyl)-N-(2,4,4-trimethylpentan-2-yl)imidazo[1,2-a]pyridin-3-amine
[314] N-tert-butyl-6-chloro-2-(4-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyridin-3-amine
[315] 6-chloro-N-cyclohexyl-2-(4-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyridin-3-amine
[316] N-tert-butyl-6-chloro-2-(5-(pyridin-2-ylethynyl)furan-2-yl)imidazo[1,2-a]pyridin-3-amine
[317] 6-chloro-N-cyclohexyl-2-(5-(pyridin-2-ylethynyl)furan-2-yl)imidazo[1,2-a]pyridin-3-amine
[318] 6-chloro-2-(5-(pyridin-2-ylethynyl)furan-2-yl)-N-(2,4,4-trimethylpentan-2-yl)imidazo[1,2-a]pyridin-3-amine
[319] 6-chloro-N-cyclopentyl-2-(3-((6-methylpyridin-2-yl)ethynyl)phenyl)imidazo[1,2-a]pyridin-3-amine
[320] N-tert-butyl-6-chloro-2-(3-((6-methylpyridin-2-yl)ethynyl)phenyl)imidazo[1,2-a]pyridin-3-amine
[321] N-tert-butyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine bis-hydrochloride
[322] N-methyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine
[323] N-tert-butyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine bis-hydrochloride
[324] [2-(5-pyridin-2-ylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(1,1,3,3-tetramethyl-butyl)-amine
[325] tert-butyl-[2-(5-pyrimidin-2-ylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-amine hydrochloride
[326] {2-[5-(3-amino-pyridin-2-ylethynyl)-thiophen-2-yl]-imidazo[1,2-a]pyridin-3-yl}-tert-butyl-amine
[327] tert-butyl-[2-(5-pyridin-2-ylethynyl-thiazol-2-yl)-imidazo[1,2-a]pyridin-3-yl]-amine
[328] tert-butyl-[2-(2-pyridin-2-ylethynyl-thiazol-5-yl)-imidazo[1,2-a]pyridin-3-yl]-amine
[329] tert-butyl-{2-[5-(6-fluoro-pyridin-2-ylethynyl)-thiophen-2-yl]-imidazo[1,2-a]pyridin-3-yl}-amine hydrochloride
[330] tert-butyl-{2-[5-(3-chloro-5-fluoro-phenylethynyl)-thiophen-2-yl]-imidazo[1,2-a]pyridin-3-yl}-amine hydrochloride
[331] tert-butyl-[2-(5-pyridin-2-ylethynyl-thiophen-2-yl)-imidazo[1,2-b]pyridazin-3-yl]-amine hydrochloride
[332] tert-butyl-[2-(5-thiazol-2-ylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-amine hydrochloride
[333] tert-butyl-{2-[5-(3-trifluoromethoxy-phenylethynyl)-thiophen-2-yl]-imidazo[1,2-a]pyrazin-3-yl}-amine
[334] tert-butyl-{2-[5-(3-[1,3]dioxolan-2-yl-phenylethynyl)-thiophen-2-yl]-imidazo[1,2-a]pyridin-3-yl}-amine
[335] tert-butyl-{2-[5-(3,5-dimethyl-phenylethynyl)-thiophen-2-yl]-imidazo[1,2-a]pyridin-3-yl}-amine hydrochloride
[336] tert-butyl-{2-[5-(3-fluoro-pyridin-2-ylethynyl)-thiophen-2-yl]-imidazo[1,2-a]pyridin-3-yl}-amine hydrochloride
[337] tert-butyl-{2-[5-(3-methyl-3H-imidazol-4-ylethynyl)-thiophen-2-yl]-imidazo[1,2-a]pyridin-3-yl}-amine hydrochloride
[338] tert-butyl-{2-[5-(5-chloro-thiophen-2-ylethynyl)-thiophen-2-yl]-imidazo[1,2-a]pyridin-3-yl}-amine hydrochloride
[339] tert-butyl-{2-[5-(5-methyl-pyridin-2-ylethynyl)-thiophen-2-yl]-imidazo[1,2-a]pyridin-3-yl}-amine hydrochloride
[340] 1-{3-[5-(3-tert-butylamino-imidazo[1,2-a]pyridin-2-yl)-thiophen-2-ylethynyl]-phenyl}-ethanone hydrochloride
[341] {3-[5-(3-tert-butylamino-imidazo[1,2-a]pyridin-2-yl)-thiophen-2-ylethynyl]-phenyl}-methanol hydrochloride
[342] N-tert-butyl-2-(5-((3-methoxypyridin-2-yl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine
[343] N-tert-butyl-2-(5-(thiophen-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine hydrochloride
[344] 5-((5-(3-(tert-butylamino)imidazo[1,2-a]pyridin-2-yl)thiophen-2-yl)ethynyl)-2-fluorobenzonitrile hydrochloride
[345] N-tert-butyl-2-(5-((3,4-difluorophenyl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine
[346] N-tert-butyl-2-(5-((3-(methoxymethyl)phenyl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine
[347] 2-(5-((3-aminophenyl)ethynyl)thiophen-2-yl)-N-tert-butylimidazo[1,2-a]pyridin-3-amine hydrochloride
[348] N-tert-butyl-2-(5-((4-fluoro-3-methylphenyl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine hydrochloride
[349] N-tert-butyl-2-(5-((3,5-difluorophenyl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine
[350] N-tert-butyl-2-(5-(thiophen-3-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine hydrochloride
[351] N-tert-butyl-2-(5-((3-methylpyridin-2-yl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine hydrochloride
[352] 3-((5-(3-(tert-butylamino)imidazo[1,2-a]pyridin-2-yl)thiophen-2-yl)ethynyl)benzenesulfonamide hydrochloride
[353] 3-((5-(3-(tert-butylamino)imidazo[1,2-a]pyridin-2-yl)hiophen-2-yl)ethynyl)benzoic acid
[354] 3-((5-(3-(tert-butylamino)imidazo[1,2-a]pyridin-2-yl)thiophen-2-yl)ethynyl)benzamide hydrochloride
[355] N-(3-((5-(3-(tert-butylamino)imidazo[1,2-a]pyridin-2-yl)thiophen-2-yl)ethynyl)phenyl)acetamide
[356] N-tert-butyl-N-methyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine
[357] N,N-dimethyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine
[358] N-tert-butyl-N-methyl-2-(5-(pyridin-2-ylethynyl)thiazol-2-yl)imidazo[1,2-a]pyridin-3-amine
[359] (6-((5-(3-(tert-butylamino)imidazo[1,2-a]pyridin-2-yl)thiophen-2-yl)ethynyl)pyridin-2-yl)methanol
[360] N-(3-((5-(3-(tert-butylamino)imidazo[1,2-a]pyridin-2-yl)thiophen-2-yl)ethynyl)phenyl)methanesulfonamide
[361] N-tert-butyl-8-methyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride
[362] 2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine
[363] N-tert-butyl-2-(5-((3-chlorophenyl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine
[364] N-tert-butyl-2-(5-((2,3-difluorophenyl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine and
[365] N-tert-butyl-7-chloro-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine

and in each case the corresponding salts thereof, in particular the hydrochlorides thereof, and in each case the corresponding solvates thereof.

The present invention also provides a process for the production of compounds of the above-stated general formula I, in accordance with which at least one compound of the general formula II,

embedded image

in which A1, A2, A3 and A4 have the above-stated meaning, is reacted in a reaction medium, optionally in the presence of at least one organic or inorganic acid or at least one transition metal salt, with at least one isocyanide of the general formula III,

embedded image

in which R2 has the above-stated meaning, and with at least one aldehyde of the general formula IV,

embedded image

in which M1 and M2 have the above-stated meaning, and the resultant compound of the general formula V,

embedded image

in which A1, A2, A3, A4, R2, M1 and M2 have the above-stated meaning, is optionally purified and/or isolated, and optionally converted into a corresponding salt and this is optionally purified and/or isolated,

or at least one compound of the general formula II,

embedded image

in which R2 has the above-stated meaning, and with at least one aldehyde of the general formula IV,

embedded image

in which M1 has the above-stated meaning and X represents a leaving group, preferably a halogen or a sulfonic acid ester, particularly preferably chlorine, bromine or trifluoromethanesulfonate, and the resultant compound of the general formula VII,

embedded image

in which A1, A2, A3, A4, R2, M1 and X have the above-stated meaning, is optionally purified and/or isolated, and optionally converted into a corresponding salt and this is optionally purified and/or isolated, and

by reaction with at least one acetylene of the general formula XI,

embedded image

in which R, mutually independently, in each case represents a linear or branched alkyl group or represents an unsubstituted phenyl group, is converted in a reaction medium, optionally in the presence of at least one suitable catalyst, optionally in the presence of at least one copper(I) salt, preferably in the presence of copper(I) iodide, and optionally in the presence of at least one inorganic and/or organic base, into a correspondingly substituted compound of the general formula

embedded image

in which A1, A2, A3, A4, R2 and M1 have the above-stated meaning and R, mutually independently, in each case represents a linear or branched alkyl group or represents an unsubstituted phenyl group, and is optionally purified and/or isolated, and optionally converted into a corresponding salt and this is optionally purified and/or isolated,

and at least one compound of the general formula XII is converted in a reaction medium, optionally in the presence of at least one inorganic and/or organic base, optionally in the presence of at least one inorganic salt, and optionally in the presence of at least one ammonium salt, into a correspondingly substituted compound of the general formula XIII,

embedded image

in which A1, A2, A3, A4, R2 and M1 have the above-stated meaning, and is optionally purified and/or isolated, and optionally converted into a corresponding salt and this is optionally purified and/or isolated,

and at least one compound of the general formula XIII and/or at least one compound of the general formula XII, is converted by reaction with at least one compound of the general formula M2-X, in which M2 has the above-stated meaning and X represents a leaving group, preferably a halogen or a sulfonic acid ester, particularly preferably chlorine, bromine or trifluoromethanesulfonate, in a reaction medium, optionally in the presence of at least one suitable catalyst, optionally in the presence of at least one inorganic and/or organic base, optionally in the presence of at least one inorganic salt and optionally in the presence of at least one ammonium salt, into a correspondingly substituted compound of the general formula V,

embedded image

in which A1, A2, A3, A4, R2, M1 and M2 have the above-stated meaning, and is optionally purified and/or isolated, and optionally converted into a corresponding salt and this is optionally purified and/or isolated,

or a compound of the general formula VII is converted by reaction with at least one acetylene of the general formula VIII,

embedded image

in which M²has the above-stated meaning, in a reaction medium, optionally in the presence of at least one suitable catalyst, optionally in the presence of at least one copper(I) salt, preferably in the presence of copper(I) iodide and optionally in the presence of at least one inorganic and/or organic base, into a correspondingly substituted compound of the general formula V,

embedded image

and optionally the compound of the general formula V is converted by reaction with at least one compound of the general formula R3-X, in which R3 has the above-stated meaning and X represents a leaving group, preferably a halogen or a sulfonic acid ester, particularly preferably chlorine, in a reaction medium, in the presence of at least one organic or inorganic base, preferably in the presence of at least one metal hydride salt,

or by reaction with at least one compound of the general formula R20-C(═O)—OH, in which R20 has the above-stated meaning, in a reaction medium, optionally in the presence of at least one organic or inorganic base and/or in the presence of at least one coupling agent,

or by reaction with at least one compound of the general formula R20-C(═O)—X, in which R20 has the above-stated meaning and X represents a leaving group, preferably a halogen or a sulfonic acid ester, particularly preferably chlorine, bromine or trifluoromethanesulfonate, in a reaction medium, optionally in the presence of at least one organic or inorganic base,

or by reaction with at least one compound of the general formula R20-C(═O)—H, in which R20 has the above-stated meaning, in a reaction medium, optionally in the presence of at least one reducing agent,

into a compound of the general formula I, optionally in the form of a corresponding salt,

embedded image

in which A1, A2, A3, A4, R2, R3, M1 and M2 have the above-stated meaning, and this is optionally purified and/or isolated.

The present invention also provides a process for the production of compounds of the above-stated general formula I, in accordance with which at least one compound of the general formula V,

embedded image

in which A1, A2, A3, A4, R2, M1 and M2 have the above-stated meaning, is converted optionally in a reaction medium in the presence of at least one organic or inorganic acid, and the resultant compound of the general formula IX,

embedded image

in which A1, A2, A3, A4, M1 and M2 have the above-stated meaning, is optionally purified and/or isolated, and optionally converted into a corresponding salt and this is optionally purified and/or isolated and converted in a reaction medium, in the presence of at least one inorganic or organic base, preferably in the presence of at least one metal hydride salt, with at least one compound of the general formula R3-X, in which R3 has the above-stated meaning and X represents a leaving group, preferably a halogen or a sulfonic acid ester, particularly preferably chlorine, or

in a reaction medium, optionally in the presence of at least one organic or inorganic base and/or optionally in the presence of at least one coupling agent with at least one compound of the general formula R20-C(═O)—OH, in which R20 has the above-stated meaning,

or in a reaction medium, optionally in the presence of at least one organic or inorganic base with at least one compound of the general formula R20-C(═O)—X, in which R20 has the above-stated meaning and X represents a leaving group, preferably a halogen or a sulfonic acid ester, particularly preferably chlorine, bromine or trifluoromethanesulfonate,

or in a reaction medium, optionally in the presence of at least one reducing agent with at least one compound of the general formula R20-C(═O)—H, in which R20 has the above-stated meaning,

into a corresponding compound of the general formula X, optionally in the form of a corresponding salt,

embedded image

in which A1, A2, A3, A4, R3, M1 and M2 have the above-stated meaning, and this is optionally purified and/or isolated,

and optionally the compound of the general formula X is converted, by reaction with at least one compound of the general formula R2-X, in which R2 has the above-stated meaning and X represents a leaving group, preferably a halogen or a sulfonic acid ester, particularly preferably chlorine, in a reaction medium, in the presence of at least one organic or inorganic base, preferably in the presence of at least one metal hydride salt,

into a compound of the above-stated general formula I, optionally in the form of a corresponding salt,

embedded image

in which A1, A2, A3, A4, R2, R3, M1 and M2 have the above-stated meaning, and this is optionally purified and/or isolated.

The processes according to the invention for the production of substituted imidazo-3-yl-amine compounds of the above-stated general formula I are also indicated in the following schemes 1 to 4.

embedded image

In a three-component coupling reaction, amines of the general formula II are reacted with isocyanides of the general formula III and aldehydes of the general formula IV in a reaction medium, preferably selected from the group consisting of chloroform, dichloromethane, acetonitrile, methanol and ethanol, with the addition of at least one organic or inorganic acid, preferably trifluoroacetic acid or perchloric acid, or with the addition of at least one transition metal salt, preferably with the addition of at least one transition metal triflate (transition metal trifluoromethanesulfonate), particularly preferably with the addition of at least one transition metal triflate selected from the group consisting of scandium(III) trifluoromethanesulfonate, ytterbium trifluoromethanesulfonate and indium(III) trifluoromethanesulfonate, preferably at temperatures of 0° C. to 150° C. to yield compounds of the general formula V.

A further process for the production of substituted imidazo-3-yl-amine compounds of the above-stated general formula I is indicated in scheme 2.

embedded image

In stage 1, in a three-component coupling reaction, amines of the general formula II are reacted with isocyanides of the general formula III and aldehydes of the general formula VI, in which X represents a leaving group, preferably a halogen or a sulfonic acid ester, particularly preferably chlorine, bromine or trifluoromethanesulfonate, in a reaction medium, preferably selected from the group consisting of chloroform, dichloromethane, acetonitrile, methanol and ethanol, with the addition of at least one organic or inorganic acid, preferably selected from the group consisting of trifluoroacetic acid or perchloric acid, or with the addition of at least one transition metal salt, preferably with the addition of at least one transition metal triflate(transition metal trifluoromethanesulfonate), particularly preferably with the addition of at least one transition metal trifluoromethanesulfonate selected from the group consisting of scandium(III) trifluoromethanesulfonate, ytterbium trifluoromethanesulfonate and indium(III) trifluoromethanesulfonate, preferably at temperatures of 0° C. to 150° C. to yield compounds of the general formula VII, in which X represents a leaving group, preferably a halogen or a sulfonic acid ester, particularly preferably chlorine, bromine or trifluoromethanesulfonate.

In stage 2, compounds of the above-stated general formula VII, in which X represents a halogen or a sulfonic acid ester, particularly preferably chlorine, bromine or trifluoromethanesulfonate, are reacted with acetylenes of the general formula VIII in a reaction medium, preferably selected from the group consisting of methanol, ethyl acetate, ethanol, isopropanol, n-butanol, dioxane, chloroform, dichloromethane, pyridine, dimethyl sulfoxide, toluene, tetrahydrofuran, dimethylformamide, acetonitrile, diethyl ether, water and corresponding mixtures, particularly preferably selected from the group consisting of dimethylformamide, ethyl acetate, tetrahydrofuran, water and corresponding mixtures, preferably with the addition of at least one palladium catalyst, preferably selected from the group consisting of palladium(II) dichloride [PdCl2], bis(triphenylphosphine)palladium(II) acetate [Pd(PPh3)2(OAc)2], bis(triphenylphosphine)palladium(II) chloride [PdCl2(PPh3)2], palladium(II) acetate [Pd(OAc)2; Ac=acetate], bis(acetonitrile)palladium(II) chloride [(CH3CN)2)PdCl2], bis(benzonitrile)palladium(II) chloride [(PhCN)2PdCl2]and tetrakis(triphenylphosphine)palladium [(PPh3)4Pd], particularly preferably selected from the group consisting of Pd(PPh3)2(OAc)2, (PPh3)4Pd and PdCl2(PPh3)2, optionally in the presence of at least one copper(I) salt, preferably in the presence of copper(I) iodide, optionally in the presence of at least one phosphine, preferably a phosphine selected from the group consisting of triphenylphosphine, tri(tert-butyl)phosphine, triphenylarsine and tri(ortho-toluyl)phosphine, particularly preferably in the presence of triphenylphosphine, optionally with the addition of at least one inorganic salt, preferably with the addition of lithium and/or zinc chloride, optionally with the addition of at least one organic base, preferably an organic base selected from the group consisting of triethylamine, diisopropylamine, diisopropylethylamine and [1,4]-diazabicyclo-[2.2.2]octane and/or the addition of at least one inorganic base, preferably selected from the group consisting of potassium carbonate, sodium hydrogencarbonate and caesium carbonate, wherein in particular the organic base may also be the reaction medium, at temperatures of preferably −70° C. to 300° C., particularly preferably −70° C. to 150° C., to yield compounds of the general formula V.

In stage 3, compounds of the above-stated general formula VII are reacted with compounds of the above-stated general formula XI under the conditions stated in scheme 2, stage 2, to yield compounds of the general formula XII.

In stage 4, compounds of the above-stated general formula XII are reacted in a reaction medium, preferably selected from the group consisting of methanol, ethyl acetate, ethanol, isopropanol, n-butanol, dioxane, chloroform, dichloromethane, pyridine, dimethyl sulfoxide, toluene, tetrahydrofuran, dimethylformamide, acetonitrile, diethyl ether, water and corresponding mixtures, particularly preferably selected from the group consisting of dimethylformamide, ethyl acetate, tetrahydrofuran, water and corresponding mixtures, optionally in the presence of at least one inorganic base, preferably in the presence of at least one inorganic base selected from the group consisting of potassium carbonate, sodium hydroxide, potassium hydrogencarbonate, sodium hydrogencarbonate, potassium hydroxide and lithium hydroxide, optionally in the presence of at least one inorganic base, preferably at least one inorganic base selected from the group consisting of triethylamine and pyridine, optionally in the presence of at least one inorganic salt, preferably in the presence of at least one ammonium salt or in the presence of potassium fluoride and/or sodium fluoride, particularly preferably in the presence of at least one ammonium salt selected from the group consisting of tetra-n-butylammonium fluoride, tetra-n-butyl-ammonium iodide and tetrabutylammonium bromide, at temperatures of preferably −70° C. to 300° C., particularly preferably of −70° C. to 150° C., to yield compounds of the general formula XIII.

In stage 5, compounds of the above-stated general formulae XII and XIII are reacted with compounds of the general formula M2-X, in which X represents a halogen or a sulfonic acid ester, particularly preferably chlorine, bromine or trifluoromethanesulfonate, in a reaction medium, preferably selected from the group consisting of methanol, ethyl acetate, ethanol, isopropanol, n-butanol, dioxane, chloroform, dichloromethane, pyridine, dimethyl sulfoxide, toluene, tetrahydrofuran, dimethylformamide, acetonitrile, diethyl ether, water and corresponding mixtures, particularly preferably selected from the group consisting of dimethylformamide, ethyl acetate, tetrahydrofuran, water and corresponding mixtures, preferably with the addition of at least one palladium catalyst, preferably selected from the group consisting of palladium(II) dichloride [PdCl2], bis(triphenylphosphine)palladium(II) acetate [Pd(PPh3)2(OAc)2], bis(triphenylphosphine)palladium(II) chloride [PdCl2(PPh3)2], palladium(II) acetate [Pd(OAc)2; Ac=acetate], bis(acetonitrile)palladium(II) chloride [(CH3CN)2)PdCl2], bis(benzonitrile)-palladium(II) chloride [(PhCN)2PdCl2] and tetrakis(triphenylphosphine)palladium [(PPh3)4Pd], particularly preferably selected from the group consisting of Pd(PPh3)2(OAc)2, (PPh3)4Pd and PdCl2(PPh3)2, optionally in the presence of at least one copper(I) salt, preferably in the presence of copper(I) iodide, optionally in the presence of at least one phosphine, preferably a phosphine selected from the group consisting of triphenylphosphine, tri(tert-butyl)phosphine, triphenylarsine and tri(ortho-toluyl)phosphine, particularly preferably in the presence of triphenylphosphine, optionally with the addition of at least one inorganic salt, preferably with the addition of lithium and/or zinc chloride, optionally in the presence of at least one ammonium salt or in the presence of potassium fluoride and/or sodium fluoride, preferably in the presence of at least one ammonium salt selected from the group consisting of tetra-n-butyl-ammonium fluoride, tetra-n-butyl-ammonium iodide and tetrabutyl-ammonium bromide, optionally with the addition at least one organic base, preferably an organic base selected from the group consisting of triethylamine, diisopropylamine, diisopropylethylamine and [1,4]-diazabicyclo-[2.2.2]octane and/or the addition of at least one inorganic base, preferably selected from the group consisting of potassium carbonate, sodium hydrogencarbonate and caesium carbonate, wherein in particular the organic base may also be the reaction medium, at temperatures of preferably −70° C. to 300° C., particularly preferably of −70° C. to 150° C., to yield compounds of the general formula V.

The reaction of compounds of the general formula XII with compounds of the general formula M2-X preferably proceeds in the presence of at least one ammonium salt or in the presence of potassium fluoride and/or sodium fluoride.

The compounds of the general formula V may be reacted as described in scheme 3 to yield compounds of the formula X.

embedded image

In stage 1, compounds of the above-stated general formula V are reacted in a reaction medium, preferably selected from the group consisting of ethanol, methanol and acetone, with the addition of at least one organic acid, preferably acetic acid or trifluoroacetic acid and/or with the addition of at least one inorganic acid, preferably hydrochloric acid or sulfuric acid, at temperatures of preferably 0° C. to 80° C. to yield compounds of the general formula IX.

In stage 2, compounds of the above-stated general formula IX are reacted with carboxylic acids of the general formula R20-(C═O)—OH, in which R20 has the above-stated meaning, in a reaction medium, preferably selected from the group consisting of diethyl ether, tetrahydrofuran, acetonitrile, methanol, ethanol, dimethylformamide and dichloromethane, optionally in the presence of at least one coupling reagent, preferably selected from the group consisting of 1-benzotriazolyloxy-tris-(dimethylamino)-phosphonium hexafluorophosphate (BOP), dicyclohexylcarbodiimide (DCC), N′-(3-dimethylaminopropyl)-N-ethylcarbodiimide (EDCI), N-[(dimethylamino)-1H-1,2,3-triazolo[4,5-b]pyridino-1-ylmethylene]-N-methylmethanaminium hexafluorophosphate N-oxide (HATU), O-(benzotriazol-1-yl)-N,N N′, N′-tetramethyluronium hexafluorophosphate (HBTU) and 1-hydroxy-7-azabenzotriazole (HOAt), optionally in the presence of at least one inorganic base, preferably selected from the group consisting of potassium carbonate and caesium carbonate, or an organic base, preferably selected from the group consisting of triethylamine, pyridine, dimethylaminopyridine and diisopropylethylamine preferably at temperatures of −70° C. to 100° C. to yield compounds of the general formula X.

Alternatively, compounds of the general formula IX are reacted with carboxylic acid derivatives or carbonic acid derivatives of the general formula R20-(C=O)—X, wherein X represents a halogen, preferably chlorine or bromine, in a reaction medium, preferably selected from the group consisting of diethyl ether, tetrahydrofuran, acetonitrile, methanol, ethanol, dimethylformamide and dichloromethane, with or without the addition of at least one organic or inorganic base, for example triethylamine, dimethylaminopyridine, pyridine or diisopropylamine, optionally in the presence of at least one organic base, preferably selected from the group consisting of triethylamine, dimethylaminopyridine, pyridine and diisopropylamine, or an inorganic base at temperatures of preferably −70° C. to 100° C. to yield compounds of the general formula X.

As a further alternative, compounds of the general formula IX are reacted with aldehydes of the general formula R20-C(═O)—H in a reaction medium, preferably selected from the group consisting of diethyl ether, tetrahydrofuran, methanol, ethanol, dichloromethane and toluene, with the addition of at least one reducing agent, preferably selected from the group consisting of sodium borohydride, sodium acetoxyborohydride or sodium cyanoborohydride, at temperatures of preferably −70° C. to 100° C. to yield compounds of the general formula X.

Likewise, compounds of the general formula IX may be reacted with compounds of the general formula R3-X, in which X represents a halogen, preferably chlorine, in a reaction medium, preferably selected from the group consisting of toluene, tetrahydrofuran and diethyl ether, with the addition of at least one metal hydride salt, preferably with the addition of at least one metal hydride salt selected from the group consisting of sodium hydride, potassium hydride and lithium hydroxide, at temperatures of preferably 0° C. to 40° C. to yield compounds of the general formula X.

Compounds of the general formulae X and V may, as indicated in scheme 4, be further reacted to yield the compounds of the general formula I, wherein the same methods as described under scheme 3, stage 2 may be used.

embedded image

The compounds of the above-stated formulae II, III, IV, VI and VIII, and the above-stated general formulae R2-X, R3-X, R20-C(═O)—OH, R20-C(═O)—X and R20-C(═O)—H are in each case commercially available and/or may be produced using conventional processes known to the person skilled in the art.

The above-described reactions may in each case be performed under conventional conditions familiar to the person skilled in the art, for example with regard to pressure or the sequence of addition of the components. Optimum control of the process under the respective conditions may optionally be established by the person skilled in the art by simple preliminary testing.

The intermediate and final products obtained by the above-described reactions may in each case, if desired and/or necessary, be purified and/or isolated by conventional methods known to the person skilled in the art. Suitable purification methods are, for example, extraction methods and chromatographic methods such as column chromatography or preparative chromatography.

All the above-described process steps and in each case also the purification and/or isolation of intermediate or final products may be performed in part or entirely under an inert gas atmosphere, preferably under a nitrogen atmosphere.

The substituted imidazo-3-yl-amine compounds according to the invention of the above-stated general formulae I, Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ik, Im and In, hereinafter designated only as compounds of the general formula I, and corresponding stereoisomers may be isolated both in the form of the free bases thereof, the free acids thereof and in the form of corresponding salts, in particular physiologically acceptable salts.

The free bases of the particular substituted imidazo-3-yl-amine compounds according to the invention of the above-stated general formula I and corresponding stereoisomers may, for example, be converted into the corresponding salts, preferably physiologically acceptable salts by reaction with an inorganic or organic acid, preferably with hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, methanesulfonic acid, p-toluenesulfonic acid, carbonic acid, formic acid, acetic acid, oxalic acid, succinic acid, tartaric acid, mandelic acid, fumaric acid, lactic acid, citric acid, glutamic acid or aspartic acid.

The free bases of the respective substituted imidazo-3-yl-amine compounds of the above-stated general formula I and corresponding stereoisomers may likewise be converted into the corresponding physiologically acceptable salts with the free acid or a salt of a sugar substitute, such as for example saccharin, cyclamate or acesulfame.

The free acids of the substituted imidazo-3-yl-amine compounds of the above-stated general formula I and corresponding stereoisomers may correspondingly be converted into the corresponding physiologically acceptable salts by reaction with a suitable base. Alkali metal salts, alkaline earth metal salts or ammonium salts [NHxR4-x]+, in which x=0, 1, 2, 3 or 4 and R represents a linear or branched C1-4 alkyl group may be mentioned by way of example.

The substituted imidazo-3-yl-amine compounds according to the invention of the above-stated general formula I and corresponding stereoisomers may optionally, like the corresponding acids, the corresponding bases or salts of these compounds, also be obtained in the form of the solvates thereof, preferably in the form of the hydrates thereof, by conventional methods known to the person skilled in the art.

If the substituted imidazo-3-yl-amine compounds according to the invention of the above-stated general formula I are obtained after the production thereof in the form of the stereoisomers thereof, preferably in the form of the racemates thereof or other mixtures of their various enantiomers and/or diastereomers, these may be separated and optionally isolated by conventional methods known to the person skilled in the art. Examples which may be mentioned are chromatographic separation methods, in particular liquid chromatography methods at standard pressure or at elevated pressure, preferably MPLC and HPLC methods, and fractional crystallisation methods. Individual enantiomers, e.g. diastereomeric salts formed by means of HPLC on a chiral stationary phase or by means of crystallisation with chiral acids, such as (+)-tartaric acid, (−)-tartaric acid or (+)-10-camphorsulfonic acid, may here in particular be separated from one another.

The substituted imidazo-3-yl-amine compounds according to the invention of the above-stated general formula I and corresponding stereoisomers as well as in each case the corresponding acids, bases, salts and solvates are toxicologically safe and are therefore suitable as pharmaceutical active ingredients in pharmaceutical formulations.

The present invention accordingly also provides a pharmaceutical formulation containing at least one imidazo-3-yl-amine compound according to the invention of the above-stated general formula I, in each case optionally in the form of one of the pure stereoisomers thereof, in particular enantiomers or diastereomers, the racemates thereof or in the form of a mixture of stereoisomers, in particular the enantiomers and/or diastereomers, in any desired mixing ratio, or in each case in the form of a corresponding salt, or in each case in the form of a corresponding solvate, and optionally one or more pharmaceutically acceptable auxiliary substances.

The pharmaceutical formulation according to the invention is suitable for mGluR5 receptor regulation, in particular for inhibiting the mGluR5 receptor and thus also for the prevention and/or treatment of disorders and/or diseases, which are mediated at least in part by mGluR5 receptors.

The pharmaceutical formulation according to the invention is therefore preferably suitable for the treatment and/or prevention of pain, preferably of pain selected from the group consisting of acute pain, chronic pain, neuropathic pain and visceral pain; of migraine; depression; neurodegenerative diseases, preferably selected from the group consisting of Parkinson's disease, Alzheimer's disease, Huntington's chorea and multiple sclerosis; cognitive disorders, preferably cognitive deficiency states, particularly preferably of attention deficit syndrome (ADS); panic attacks; anxiety disorder; epilepsy; coughing; urinary incontinence; diarrhoea; pruritus; schizophrenia; cerebral ischaemia; muscle spasms; cramps; irritable bowel syndrome; disorders of food intake, preferably selected from the group consisting of bulimia, cachexia, anorexia and obesity; abuse of alcohol and/or drugs (in particular nicotine and/or cocaine) and/or medicines, dependency on alcohol and/or drugs (in particular nicotine and/or cocaine) and/or dependency on medicines, preferably for the prevention and/or reduction of withdrawal symptoms associated with dependency on alcohol and/or drugs (in particular nicotine and/or cocaine) and/or dependency on medicines; the development of tolerance phenomena with regard to drugs and/or medicines, in particular with regard to opioids; of gastro-oesophageal reflux syndrome; of gastro-oesophageal reflux; for diuresis; for antinatriuresis; for influencing the cardiovascular system; for anxiolysis; for increasing vigilance; for increasing libido; for modulating locomotor activity, and for local anaesthesia.

Particularly preferably, the pharmaceutical formulation according to the invention is suitable for the treatment and/or prevention of pain preferably selected from the group consisting of acute pain, chronic pain, neuropathic pain and visceral pain; depression; epilepsy; neurodegenerative diseases, preferably selected from the group consisting of Parkinson's disease, Alzheimer's disease, Huntington's chorea and multiple sclerosis; abuse of alcohol and/or drugs (in particular nicotine and/or cocaine) and/or abuse of medicines, dependency on alcohol and/or drugs (in particular nicotine and/or cocaine) and/or dependency on medicines, preferably for the prevention and/or reduction of withdrawal symptoms associated with dependency on alcohol and/or drugs (in particular nicotine and/or cocaine) and/or dependency on medicines; the development of tolerance phenomena with regard to drugs and/or medicines, in particular with regard to opioids; or for anxiolysis.

The pharmaceutical formulation according to the invention is very particularly preferably suitable for the treatment and/or prevention of pain, preferably of pain selected from the group consisting of acute pain, chronic pain, neuropathic pain and visceral pain.

The present invention also provides the use of at least one imidazo-3-yl-amine compound according to the invention of the above-stated general formula I, in each case optionally in the form of one of the pure stereoisomers thereof, in particular enantiomers or diastereomers, the racemates thereof or in the form of a mixture of stereoisomers, in particular the enantiomers and/or diastereomers, in any desired mixing ratio, or in each case in the form of a corresponding salt, or in each case in the form of a corresponding solvate, and optionally one or more pharmaceutically compatible auxiliary substances for the production of a pharmaceutical formulation for mGluR5 receptor regulation, preferably for inhibiting the mGluR5-receptor.

It is preferred to use at least one substituted imidazo-3-yl-amine compound of the above-stated general formula I, in each case optionally in the form of one of the pure stereoisomers thereof, in particular enantiomers or diastereomers, the racemates thereof or in the form of a mixture of stereoisomers, in particular the enantiomers and/or diastereomers, in any desired mixing ratio, or in each case in the form of a corresponding salt, or in each case in the form of a corresponding solvate, and optionally one or more pharmaceutically compatible auxiliary substances for the production of a pharmaceutical formulation for the prevention and/or treatment of disorders and/or diseases which are mediated at least in part by mGluR5 receptors.

It is particularly preferred to use at least one substituted imidazo-3-yl-amine compound the above-stated general formula I, in each case optionally in the form of one of the pure stereoisomers thereof, in particular enantiomers or diastereomers, the racemates thereof or in the form of a mixture of stereoisomers, in particular the enantiomers and/or diastereomers, in any desired mixing ratio, or in each case in the form of a corresponding salt, or in each case in the form of a corresponding solvate, and optionally one or more pharmaceutically compatible auxiliary substances for the production of a pharmaceutical formulation for the treatment and/or prevention of pain preferably selected from the group consisting of acute pain, chronic pain, neuropathic pain and visceral pain; of migraine; depression; neurodegenerative diseases, preferably selected from the group consisting of Parkinson's disease, Alzheimer's disease, Huntington's chorea and multiple sclerosis; cognitive disorders, preferably cognitive deficiency states, particularly preferably of attention deficit syndrome (ADS); panic attacks; anxiety disorder; epilepsy; coughing; urinary incontinence; diarrhoea; pruritus; schizophrenia; cerebral ischaemia; muscle spasms; cramps; irritable bowel syndrome; disorders of food intake, preferably selected from the group consisting of bulimia, cachexia, anorexia and obesity; abuse of alcohol and/or drugs (in particular nicotine and/or cocaine) and/or abuse of medicines, dependency on alcohol and/or drugs (in particular nicotine and/or cocaine) and/or dependency on medicines, preferably for the prevention and/or reduction of withdrawal symptoms associated with dependency on alcohol and/or drugs (in particular nicotine and/or cocaine) and/or dependency on medicines; the development of tolerance phenomena with regard to drugs and/or medicines, in particular with regard to opioids; of gastro-oesophageal reflux syndrome; of gastro-oesophageal reflux; for diuresis; for antinatriuresis; for influencing the cardiovascular system; for anxiolysis; for increasing vigilance; for increasing libido; for modulating locomotor activity, and for local anaesthesia.

It is very particularly preferred to use at least one substituted imidazo-3-yl-amine compound of the above-stated general formula I, in each case optionally in the form of one of the pure stereoisomers thereof, in particular enantiomers or diastereomers, the racemates thereof or in the form of a mixture of stereoisomers, in particular the enantiomers and/or diastereomers, in any desired mixing ratio, or in each case in the form of a corresponding salt, or in each case in the form of a corresponding solvate, and optionally one or more pharmaceutically compatible auxiliary substances for the production of a pharmaceutical formulation for the treatment and/or prevention of pain preferably selected from the group consisting of acute pain, chronic pain, neuropathic pain and visceral pain.

The pharmaceutical formulation according to the invention is suitable for administration to adults and children including small children and babies.

The pharmaceutical formulation according to the invention may be formulated as a liquid, semisolid or solid dosage form, for example in the form of solutions for injection, drops, succi, syrups, sprays, suspensions, tablets, patches, capsules, dressings, suppositories, ointments, creams, lotions, gels, emulsions, aerosols or in multiparticulate form, for example in the form of pellets or granules, optionally pressed into tablets, packaged in capsules or suspended in a liquid, and may also be administered as such.

In addition to at least one substituted imidazo-3-yl-amine compound of the above-stated general formula I, optionally in the form of one of the pure stereoisomers thereof, in particular enantiomers or diastereomers, the racemate thereof or in the form of mixtures of the stereoisomers, in particular the enantiomers or diastereomers, in any desired mixing ratio, or optionally in the form of a corresponding salt or in each case in the form of a corresponding solvate, the pharmaceutical formulation according to the invention conventionally contains further physiologically acceptable pharmaceutical auxiliary substances, which may preferably be selected from the group consisting of matrix materials, fillers, solvents, diluents, surface-active substances, dyes, preservatives, disintegrants, slip agents, lubricants, aromas and binders.

Selection of the physiologically acceptable auxiliary substances and the quantities thereof which are to be used depends upon whether the pharmaceutical formulation is to be administered orally, subcutaneously, parenterally, intravenously, intraperitoneally, intradermally, intramuscularly, intranasally, buccally, rectally or topically, for example onto infections of the skin, mucous membranes and eyes. Preparations in the form of tablets, coated tablets, capsules, granules, pellets, drops, succi and syrups are preferred for oral administration, while solutions, suspensions, readily reconstitutible dried preparations and sprays are preferred for parenteral, topical and inhalatory administration.

The substituted imidazo-3-yl-amine compounds according to the invention used in the pharmaceutical formulation according to the invention in a depot in dissolved form or in a dressing, optionally with the addition of skin penetration promoters, are suitable percutaneous administration preparations.

Orally or percutaneously administrable formulations may also release the particular substituted imidazo-3-yl-amine compound according to the invention in delayed manner.

Production of the pharmaceutical formulations according to the invention proceeds with the assistance of conventional means, devices, methods and processes known from the prior art, as are described for example in “Remington's Pharmaceutical Sciences”, ed. A. R. Gennaro, 17th ed., Mack Publishing Company, Easton, Pa. (1985), in particular in part 8, chapters 76 to 93. The corresponding description is hereby introduced as a reference and is deemed to be part of the disclosure.

The quantity of the particular substituted imidazo-3-yl-amine compounds according to the invention of the above-stated general formula I to be administered to the patient may vary and is for example dependent on the weight or age of the patient and on the mode of administration, the indication and the severity of the complaint. Conventionally, 0.005 to 2000 mg/kg, preferably 0.05 to 500 mg/kg, particularly preferably 0.05 to 100 mg/kg of patient body weight of at least one such compound according to the invention are administered per day.

Pharmacological Methods:

1. Method for Determining Affinity for the mGluR5 Receptor

Pig brain homogenate is produced by homogenisation (Polytron Pt 3000, Kinematica AG, 10,000 revolutions per minute for 90 seconds) of pig brain hemispheres without medulla, cerebellum and pons in a buffer of pH 8.0 (30 mM Hepes, Sigma, order number H3375+1 tablet Complete Roche Diagnostics, order number 1836145 made up to 100 ml) in a ratio of 1:20 (brain weight/volume) and differential centrifugation at 900×g and 40,000×g. 450 μg of protein from brain homogenate is incubated in each case in 250 μl incubation batches in 96-well microtitre plates with 5 nM 3[H]-MPEP (Tocris, order number R1212) (MPEP=2-methyl-6-(3-methoxyphenyl)-ethynylpyridine) and the compounds to be investigated (10 μM in the test) in the buffer (as above) at room temperature for 60 minutes.

The batches are then filtered with the assistance of a Brandel Cell Harvester (Brandel, Grade Robotic 9600) on Unifilter plates with glass filter mats (Perkin Elmer, order number 6005177) and then washed 3 times with buffer (as above) using 250 μl per sample. The filter plates are then dried for 60 minutes at 55° C. Then 30 μl of Ultima Gold™ scintillating material (Packard BioScience, order number 6013159) is added per well and after 3 hours the samples are measured using the β counter (Microbeta, Perkin Elmer). Nonspecific binding is determined by the addition of 10 μM MPEP (Tocris, order number 1212).

2. Neuropathic Pain in Rats

Efficacy against neuropathic pain was investigated in the Bennett model (chronic constriction injury; Bennett and Xie, 1988, Pain 33: 87-107). The corresponding parts of the literature are hereby deemed to be part of the present disclosure.

Sprague-Dawley rats weighing 140-160 g are provided under Nembutal anaesthesia with four loose ligatures of the right ischial nerve. On the paw innervated by the damaged nerve, the animals develop hypersensitivity which, after one week's convalescence, is quantified over a period of approx. four weeks by means of a cold metal plate at 4° C. (cold allodynia). The animals are observed on this plate for a period of 2 min. and the number of withdrawal responses by the damaged paw is measured. Relative to the preliminary value prior to administration of the substance, the action of the substance is determined on four occasions over a period of one hour (15, 30, 45, 60 min. after administration) and the resultant area under the curve (AUC) and the inhibition of cold allodynia at the individual measuring points is stated as a percentage action relative to the vehicle control (AUC) or to the initial value (individual measurement points). The size of the group is n=10. The significance of an antiallodynic action is determined with reference to the AUC values by means of a paired T-test (*0.05≧p>0.01; **0.01≧p>0.001; ***p≦0.001; Armitage and Berry, 1987, Stat. Methods in Medical Research, London: Blackwell Scientific Publications).

3. “Elevated Plus Maze” Model

Compounds are tested for a possible anxiolytic effect in the “elevated plus maze” (EPM) model. The tests are carried out on male Sprague-Dawley rats (200-250 g) using 2 “elevated plus mazes” (Med Associates) with electronically controlled infrared photobeams for determining the location of the animals in the maze. Each maze has 2 open and 2 closed arms and a central platform. The edges of the open arms are delimited by narrow strips. The entire maze is mounted on a metal stand.

At the beginning of a 5 minute test, each animal is individually placed on the central platform with its head in the direction of a closed arm.

The following parameters are determined or calculated and evaluated:

the number and percentage of entries into the open and closed arms,

and the percentage of time spent in the open and closed arms and on the central platform.

The data are analysed by means of single factor ANOVA (comparison of treatment groups vs. vehicle group). The significance level is set at p<0.05. All groups have a size of N=10.

The test is also described in Hogg, S. (1996) A review of the validity and variability of the elevated plus-maze as an animal model of anxiety. Pharmacol. Biochem. Behav. 54, 21-30 and Rodgers, R. J., Cole, J. C. (1994) The elevated plus-maze: pharmacology, methodology and ethology, in: Cooper, S. J., Hendrie, C. A. (eds.) Ethology and Psychopharmacology, Wiley & Sons; pp. 9-44. The corresponding passages of the literature are hereby deemed to be part of the disclosure.

4. Formaldehyde Test

a. Formaldehyde Test (Rat)

The formaldehyde test as described in Dubuisson, D. and Dennis, S. G., 1977, Pain, 4, 161-174 is a model of acute and chronic pain. The corresponding passages from the literature are hereby deemed to be part of the disclosure. A biphasic nociceptive response is induced in freely mobile test animals by a single formaldehyde injection into the dorsal side of a hind paw, said response being detected by the observation of three clearly distinguishable behaviour patterns. The response is in two phases: phase 1= immediate response (duration up to 10 min; paw shaking, licking), phase 2=late response (after a resting phase; likewise paw shaking, licking; duration up to 60 min). The 1st phase reflects direct stimulation of the peripheral nocisensors with an elevated spinal nociceptive input or glutamate release (acute pain phase); the 2nd phase reflects spinal and peripheral hypersensitisation (chronic pain phase). In the investigations presented here, it was the chronic pain component (phase 2) which was evaluated.

Formaldehyde is administered subcutaneously in a volume of 50 μl and a concentration of 5% into the dorsal side of the right hind paw of each animal. The substances to be tested are administered intraperitoneally (i.p.) 15 min before the formaldehyde injection, or intravenously (i.v.) 5 min before the formaldehyde injection. The specific behavioural changes, such as raising and shaking the paw, changes in weight bearing of the animal and biting and licking responses are observed and recorded over the observation period of 21 to 27 min after the formaldehyde injection. The various behaviours are summarised as a “pain rate” (PR), which is the calculated nociceptive response averaged over 3 min sub-intervals. The PR is calculated on the basis of a numerical weighting (=in each case a factor of 1, 2, 3) of the observed behaviours (corresponding behaviour score 1, 2, 3) and is calculated using the following formula: PR=[(T0×0)+(T1×1)+(T2×2)+(T3×3)]/180

wherein T0, T1, T2, and T3 correspond to the time in seconds for which the animal exhibited behaviour 0, 1, 2 or 3 respectively. Group size is 10 animals (n=10).

b. Formaldehyde Test in Mice

Formaldehyde is administered subcutaneously in a volume of 20 μl and a concentration of 1% into the dorsal side of the right hind paw of each animal. The substances to be tested are administered intraperitoneally (i.p.) 15 min before the formaldehyde injection. The specific behavioural changes, such as raising and shaking the paw (score 3, Dubuisson & Dennis, 1977) are observed and recorded over the observation period of 21 to 24 min after the formaldehyde injection. Group size is 10 animals (n=10).

The invention is explained below with reference to Examples. These explanations are given merely by way of example and do not restrict the general concept of the invention.

EXAMPLES

Certain embodiments of the present invention may be further understood by reference to the following specific examples. These examples and the terminology used herein are for the purpose of describing particular embodiments only and are not intended to be limiting.

The yields of the compounds produced are not optimised.

All temperatures are uncorrected.

Abbreviations:

equivalent
molar equivalent

aq.
aqueous

d
days

DCC
dicyclohexylcarbodiimide

DCM
dichloromethane

DMAP
4-dimethylaminopyridine

DMF
N,N-dimethylformamide

DIPE
diisopropyl ether

EA
ethyl acetate

EDCI
N′-(3-dimethylaminopropyl)-N-ethylcarbodiimide

ether
diethyl ether

EtOH
ethanol

sat.
saturated

H2O
water

HATU
N-[(dimethyamino)-1H-1,2,3-triazolo[4,5-b]pyri-

dino-1-ylmethylene]-N-methylmethanaminium

hexafluorophosphate N-oxide

HBTU
O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium

hexafluorophosphate

MeCN
acetonitrile

MeOH
methanol

NEt3
triethylamine

RT
room temperature

CC
column chromatography

THF
tetrahydrofuran

The chemicals and solvents used were purchased from conventional suppliers (Acros, Avocado, Aldrich, Bachem, Fluka, Lancaster, Maybridge, Merck, Sigma, TCI, etc.) or synthesised by conventional methods known to the person skilled in the art.

Silica gel 60 (0.040-0.063 mm) from E. Merck, Darmstadt, was used as the stationary phase for the column chromatography.

Thin-layer chromatography was performed with pre-coated silica gel 60 F 254 HPTLC plates from E. Merck, Darmstadt.

The mixture ratios of solvents, mobile solvents or for chromatographic investigations are always stated by volume/volume.

Analysis was carried out by mass spectroscopy and NMR.

General Methods for the Production of Substituted Bicyclic imidazo-3-yl-amines According to the Examples

embedded image

Amines (1 equivalent) of the general formula II (1 equivalent) were reacted at temperatures of 0° C. to 150° C. with isocyanides of the general formula III and aldehydes (1 equivalent) of the general formula IV to yield compounds of the general formula V in organic solvents or solvent mixtures, for example of chloroform, DCM, MeCN, MeOH or EtOH, with addition of an organic or inorganic acid, for example trifluoroacetic acid or perchloric acid, or with addition of a transition metal triflate, for example scandium(III) triflate, ytterbium triflate or indium(III) triflate.

embedded image

In stage 1, amines (1 equivalent) of the general formula II were reacted at temperatures of 0° C. to 150° C. with isocyanides (1 equivalent) of the general formula III and aldehydes (1 equivalent) of the general formula VI, in which X represents a halogen, to yield compounds of the general formula VII in organic solvents or solvent mixtures, for example of chloroform, DCM, MeCN, MeOH or EtOH, with addition of an organic or inorganic acid, for example trifluoroacetic acid or perchloric acid, or with addition of a transition metal triflate, for example scandium(III) triflate, ytterbium triflate or indium(III) triflate.

In stage 2, compounds of the general formula VII (1 equivalent), in which X represents a halogen, were reacted at temperatures of −70° C. to 150° C. with acetylenes (2.5 equivalents) of the general formula VIII to yield compounds of the general formula V in a solvent or solvent mixture, for example of toluene, THF, DMF, MeCN, ether, NEt3 or diisopropylamine, with addition of a palladium catalyst, for example bis(triphenylphosphine)palladium(II) chloride, of copper(I) iodide and an organic base, for example NEt3 or diisopropylamine, and/or inorganic base, for example potassium carbonate or caesium carbonate.

embedded image

In stage 1, compounds of the general formula V were reacted at temperatures of 0° C. to 80° C. to yield amines of the general formula IX in a solvent or solvent mixture, for example of EtOH, MeOH or acetone, with addition of an organic or inorganic acid, for example acetic acid, trifluoroacetic acid, hydrochloric acid or sulfuric acid.

In stage 2, compounds of the general formula IX (1 equivalent) were reacted at temperatures of −70° C. to 100° C. with carboxylic acids (1 equivalent) of the general formula R20-(C═O)—OH in a solvent or solvent mixture, for example of ether, THF, MeCN, MeOH, EtOH, DMF or DCM, with or without addition of a coupling reagent (1 equivalent), for example DCC, BOP, HATU or EDCI and optionally in the presence of at least one inorganic or organic base, for example NEt3 or diisopropylethylamine, to yield compounds of the general formula X.

Alternatively, compounds of the general formula IX (1 equivalent) were reacted at temperatures of −70° C. to 100° C. with carboxylic acid halides (1 equivalent) or carbonic acid derivatives of the general formula R20-(C═O)—X, wherein X represents a halogen, in a solvent or solvent mixture, for example of ether, THF, MeCN, MeOH, EtOH, DMF or DCM, with or without addition of an organic or inorganic base, for example NEt3, DMAP, pyridine or diisopropylamine, to yield compounds of the general formula X.

As a further alternative, compounds of the general formula IX (1 equivalent) were reacted at temperatures of −70° C. to 100° C. with aldehydes (1 equivalent) of the general formula R20-C(═O)—H in a solvent or solvent mixture, for example of ether, THF, MeOH, EtOH, DCM or toluene, and subsequent addition of a reducing agent, for example sodium borohydride, sodium acetoxyborohydride or sodium cyanoborohydride, to yield compounds of the general formula X.

Compounds of the general formula IX (1 equivalent) were likewise reacted at temperatures of 0° C. to 40° C. with compounds of the general formula R3-X (1.1 equivalents), in which X represents a halogen, preferably chlorine, in a solvent or solvent mixture, for example of toluene, THF or ether, with addition of a metal hydride salt (1.1 equivalents), preferably with addition of sodium hydride, to yield compounds of the general formula X.

embedded image

The compounds of the general formula V or X may be reacted using the same methods as described in general synthesis scheme 3, stage 2 to yield compounds of the general formula I.

The above-described methods for the production of substituted bicyclic imidazo-3-yl-amines are described in greater detail below with reference to some example compounds:

Example 1
Synthesis of cyclopentyl-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine

10 μl (0.022 mmol) of 20% aq. perchloric acid, a solution of 31.8 mg (0.15 mmol) of 5-phenylethynyl-thiophene-2-carbaldehyde in a mixture of MeOH and DCM (0.5 ml, 1:1 vol/vol) and a solution of 11.1 mg (0.115 mmol) of cyclopentyl isocyanide in MeOH (0.5 ml) were added in succession to a solution of 9.5 mg (0.1 mmol) of 2-aminopyrazine in MeOH (1 ml). The reaction solution was stirred at RT for 36 h and then combined with sat. aq. NaCl solution (3 ml) and stirred at RT for a further 45 min. The phases were separated and the aq. phase was extracted with DCM (2×3 ml). The collected organic phases were dried over MgSO4, filtered and evaporated under a vacuum. The group was purified by means of preparative HPLC, wherein 18 mg (0.047 mmol, 47%) of cyclopentyl-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine were obtained.

Example 18
tert-Butyl-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine

a) Synthesis of [2-(5-bromothiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-tert-butyl-amine

237 mg (2.50 mmol) of 2-aminopyrazine were dissolved together with 208 mg (2.50 mmol) of tert-butylisonitrile and 0.27 ml (2.50 mmol) of 5-bromothiophene-2-carbaldehyde in DCM (5 ml). After addition of perchloric acid (0.25 ml), the mixture was stirred at RT for 5 d. Washing was then performed with a sat. aq. sodium carbonate solution and a sat. aq. common salt solution. The organic phase was dried over magnesium sulfate, filtered and evaporated under a vacuum. After carrying out column chromatography (EA/DIPE/DCM 2:2:1) with the group, 471 mg (1.3 mmol, 54% of theoretical) of [2-(5-bromothiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-tert-butyl-amine were obtained.

b) Synthesis of tert-butyl-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine

420 mg (1.2 mmol) of [2-(5-bromothiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-tert-butyl-amine were dissolved together with 0.33 ml (3.0 mmol) of phenylacetylene, 42 mg (0.06 mmol) of bis(triphenylphosphine)-palladium(II) chloride and 22 mg (0.12 mmol) of copper(I) iodide in DMF (9 ml). After addition of 1.6 ml (12.0 mmol) of triethylamine, the mixture was stirred at 50° C. for 16 h. The reaction solution was then diluted with EA and combined with a sat. aq. sodium carbonate solution. The phases were separated and the aqueous phase extracted with EA. The combined organic phases were washed 2× with a sat. aq. sodium carbonate solution and 2× with a sat. aq. common salt solution and dried over magnesium sulfate. After filtration and removal of the solvents under a vacuum, column chromatography (EA/DCM 1:4) was carried out with the group, after which 326 mg (0.88 mmol, 73% of theoretical) of tert-butyl-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine were obtained.

Example 31
(1-Phenyl-ethyl)-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine

a) Synthesis of [2-(5-bromothiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-(1-phenyl-ethyl)-amine

951 mg (10.0 mmol) of 2-aminopyrazine were dissolved together with 1.31 g (10.0 mmol) of 1-phenylethylisonitrile and 1.08 ml (10.0 mmol) of 5-bromothiophene-2-carbaldehyde in chloroform (24 ml). After addition of perchloric acid (1.00 ml), the mixture was stirred at RT for 5 d. The mixture was then combined with a sat. aq. sodium carbonate solution and the phases were separated. The aqueous phase was extracted with DCM. The combined organic phases were washed with a sat. aq. sodium carbonate solution and dried over magnesium sulfate, filtered and evaporated under a vacuum. After carrying out column chromatography (EA/DCM 1:1) with the group, 831 mg (2.1 mmol, 21% of theoretical) of [2-(5-bromothiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-(1-phenyl-ethyl)-amine were obtained.

b) Synthesis of (1-phenyl-ethyl)-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine

497 mg (1.25 mmol) of [2-(5-bromothiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-(1-phenyl-ethyl)-amine were dissolved together with 0.34 ml (3.13 mmol) of phenylacetylene, 43 mg (0.06 mmol) of bis(triphenylphosphine)-palladium(II) chloride and 24 mg (0.13 mmol) of copper(I) iodide in DMF (10 ml) After addition of 1.7 ml (12.5 mmol) of triethylamine, the mixture was stirred at 50° C. for 16 h. The reaction solution was then diluted with EA and combined with a sat. aq. sodium carbonate solution. The phases were separated and the aqueous phase extracted with EA. The combined organic phases were washed 2× with a sat. aq. sodium carbonate solution and 2× with a sat. aq. common salt solution and dried over magnesium sulfate. After filtration and removal of the solvents under a vacuum, column chromatography (EA/DCM 1:3) was carried out with the group, after which 158 mg (0.38 mmol, 30% of theoretical) of (1-phenyl-ethyl)-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine were obtained.

Example 56
[2-(5-Phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-(1,1,3,3-tetramethyl-butyl)-amine

a) Synthesis of [2-(5-bromothiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-(1,1,3,3-tetramethyl-butyl)-amine

4.76 g (50.0 mmol) of 2-aminopyrazine were dissolved together with 8.76 ml (50.0 mmol) of 1,1,3,3-tetramethyl-butylisonitrile and 5.42 ml (50.0 mmol) of 5-bromothiophene-2-carbaldehyde in chloroform (40 ml) After addition of perchloric acid (5 ml), the mixture was stirred at 50° C. for 16 h. After cooling to RT, washing was performed 2× with a sat. aq. sodium carbonate solution. The organic phase was dried over magnesium sulfate, filtered and evaporated under a vacuum. After carrying out column chromatography (EA/DCM 1:3) with the group, 11.39 g (28.0 mmol, 56% of theoretical) of [2-(5-bromothiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-(1,1,3,3-tetramethyl-butyl)-amine were obtained.

b) Synthesis of [2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-(1,1,3,3-tetramethyl-butyl)-amine

3.65 g (9.0 mmol) of [2-(5-bromothiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-(1,1,3,3-tetra-methyl-butyl)-amine were dissolved together with 1.18 ml (10.8 mmol) of phenylacetylene, 0.16 g (0.23 mmol) of bis(triphenylphosphine)-palladium(II) chloride and 0.08 g (0.45 mmol) of copper(I) iodide in DMF (30 ml). After addition of 2.50 ml (18.00 mmol) of triethylamine, the mixture was stirred at 50° C. for 16 h. The reaction solution was then diluted with EA and combined with a sat. aq. sodium carbonate solution. The phases were separated and the aqueous phase extracted with EA. The combined organic phases were washed 2× with a sat. aq. sodium carbonate solution and dried over magnesium sulfate. After filtration and removal of the solvents under a vacuum, column chromatography (EA/DIPE/DCM 3:3:4) was carried out with the group, after which 3.38 g (7.9 mmol, 88% of theoretical) of [2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-(1,1,3,3-tetramethyl-butyl)-amine were obtained.

Example 59
[2-(5-Phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(1,1,3,3-tetramethyl-butyl)-amine

a) Synthesis of [2-(5-bromothiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(1,1,3,3-tetramethyl-butyl)-amine

235 mg (2.5 mmol) of 2-aminopyridine were dissolved together with 0.42 ml (2.5 mmol) of 1,1,3,3-tetramethyl-butylisonitrile and 0.27 ml (2.5 mmol) of 5-bromothiophene-2-carbaldehyde in DCM (5 ml). After addition of perchloric acid (0.25 ml), the mixture was stirred at RT for 5 d. Washing was then performed with a sat. aq. sodium carbonate solution and a sat. aq. common salt solution. The organic phase was dried over magnesium sulfate, filtered and evaporated under a vacuum. After carrying out column chromatography (EA/DIPE/DCM 2:2:1) with the group, 724 mg (1.7 mmol, 71% of theoretical) of [2-(5-bromothiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(1,1,3,3-tetramethyl-butyl)-amine were obtained.

b) Synthesis of [2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(1,1,3,3-tetramethyl-butyl)-amine

324 mg (0.80 mmol) of [2-(5-bromothiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(1,1,3,3-tetramethyl-butyl)-amine were dissolved together with 0.11 ml (0.96 mmol) of phenylacetylene, 14 mg (0.02 mmol) of bis(triphenylphosphine)-palladium(II) chloride and 7 mg (0.04 mmol) of copper(I) iodide in DMF (6 ml) After addition of 1.1 ml (8.0 mmol) of triethylamine, the mixture was stirred at 50° C. for 2 d. The reaction solution was then diluted with EA and combined with a sat. aq. sodium carbonate solution. The phases were separated and the aqueous phase extracted with EA. The combined organic phases were washed 2× with a sat. aq. sodium carbonate solution and 2× with a sat. aq. common salt solution and dried over magnesium sulfate. After filtration and removal of the solvents under a vacuum, column chromatography (EA/DIPE/DCM 3:3:4) was carried out with the group, after which 54 mg (0.13 mmol, 16% of theoretical) of [2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(1,1,3,3-tetramethyl-butyl)-amine were obtained.

Example 60
[2-(5-Pyridin-3-ylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-(1,1,3,3-tetramethyl-butyl)-amine

Synthesis of [2-(5-pyridin-3-ylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-(1,1,3,3-tetramethyl-butyl)-amine

600 mg (1.48 mmol) of [2-(5-bromothiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-(1,1,3,3-tetra-methyl-butyl)-amine were dissolved together with 183 mg (1.77 mmol) of 3-ethynylpyridine, 104 mg (0.15 mmol) of bis(triphenylphosphine)-palladium(II) chloride and 28 mg (0.15 mmol) of copper(I)-iodide in DMF (10 ml). After addition of 2.00 ml (14.78 mmol) of triethylamine, the mixture was stirred at 50° C. for 3 d. The reaction solution was then diluted with EA and combined with a sat. aq. sodium carbonate solution. The phases were separated and the aqueous phase extracted with EA. The combined organic phases were washed 2× with a sat. aq. sodium carbonate solution and dried over sodium sulfate. After filtration and removal of the solvents under a vacuum, column chromatography (EA) was carried out with the group. After crystallisation of the resultant crude product, 310 mg (0.72 mmol, 49% of theoretical) of [2-(5-pyridin-3-ylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-(1,1,3,3-tetramethyl-butyl)-amine were obtained.

Example 83
2-(5-Phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-ylamine hydrochloride

2.32 g (5.44 mmol) of [2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-(1,1,3,3-tetramethylbutyl)-amine (Example 60) were dissolved in methanol (90 ml) and combined with 5.3 ml (54.4 mmol) of a 32% HCl solution. The reaction solution was stirred at RT for 16 h. The resultant precipitate was filtered out and rewashed with methanol, 1.39 g (3.95 mmol, 73% of theoretical) of 2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-ylamine hydrochloride being obtained as a solid.

Example 65
Dimethyl-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine

790 mg (2.5 mmol) of 2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-ylamine hydrochloride (Example 83) were dissolved in DMF (8 ml). After addition of 300 mg (7.5 mmol) of sodium hydride (60% dispersion in mineral oil) in portions, the mixture was stirred at RT for 30 min. 0.3 ml (5.0 mmol) of methyl iodide dissolved in DMF (2 ml) was then added dropwise. The reaction solution was stirred at RT for a further 4 h and then quenched with water (20 ml) and extracted with EA (2×50 ml). The combined organic phases were dried over MgSO4, filtered and evaporated under a vacuum. 351 mg (1.0 mmol, 40% of theoretical) of dimethyl-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine were obtained from the group by crystallisation (EA).

Example 68
Ethyl-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine

395 mg (1.25 mmol) of 2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-ylamine hydrochloride (Example 83) were dissolved in DMF (8 ml). After addition of 100 mg (2.5 mmol) of sodium hydride (60% dispersion in mineral oil), the mixture was stirred at RT for 1 h. A solution of 74 μl (0.8 mmol) of ethyl bromide in DMF (2 ml) was then added dropwise. The reaction solution was stirred at RT for 16 h, quenched with water (10 ml) and extracted with EA (2×50 ml). The combined organic phases were dried over MgSO4, filtered and evaporated under a vacuum. 253 mg (0.74 mmol, 58% of theoretical) of ethyl-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine were obtained by means of column chromatography (silica gel, EA/DCM 4:1).

Example 94
Synthesis of N-tert-butyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine

1.32 g (14.1 mmol) of 2-aminopyrazine were dissolved together with 3.00 g (14.1 mmol) of 5-pyridin-2-ylethynyl-thiophene-2-carbaldehyde, 1.59 ml (14.1 mmol) of tert.-butyl-isonitrile and 2.07 g (4.2 mmol) of scandium(III) trifluoromethanesulfonate in chloroform (40 ml). The reaction solution was heated to 80° C. for 60 min in the microwave (800 watt, MLS-Ethos1600) and then diluted with DCM. Washing was then performed with a 1M Na2CO3 solution and a sat. aq. NaCl solution. The mixture was then dried over Na2SO4, filtered and evaporated under a vacuum. 3.43 g (9.2 mmol, 65%) of N-tert-butyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine were obtained by crystallisation of the group from EA.

Example 116
Synthesis of N-tert-butyl-2-(4-(pyridin-2-ylethynyl)phenyl)-imidazo[1,2-a]pyrazin-3-amine

500 mg (2.4 mmol) of 4-pyridin-2-ylethynyl-benzaldehyde, 200 mg (2.4 mmol) of tert.-butyl-isonitrile and 215 μl (0.48 mmol) of 20% aq. perchloric acid were added in succession to a solution of 229 mg (2.4 mmol) of 2-aminopyrazine in chloroform (20 ml). The reaction solution was stirred at 45° C. for 16 h and then diluted with DCM. Washing was then performed with a 1M Na2CO3 solution and a sat. aq. NaCl solution. The mixture was then dried over MgSO4, filtered and evaporated under a vacuum. CC (EA) was carried out with the group, 565 mg (1.5 mmol, 64%) of N-tert-butyl-2-(4-(pyridin-2-ylethynyl)phenyl)-imidazo[1,2-a]pyrazin-3-amine being obtained.

Example 120
Synthesis of 3-(tert-butylamino)-2-(5-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazine-8-carboxylic acid

A solution of 200 mg (0.47 mmol) of 3-(tert-butylamino)-2-(5-(phenylethynyl)-thiophen-2-yl)imidazo[1,2-a]pyrazine-8-carboxylic acid methyl ester (Example 106) in a mixture of MeOH (5 ml) and MeCN (5.5 ml) was combined with 5 ml (0.51 mmol) of a 0.1M aq. NaOH solution and stirred at RT for 1 h. The reaction mixture was then combined with 26 μl of a 5 N aq. acetic acid solution. The solvents were then largely removed by distillation under a vacuum. The residual aq. phase was repeatedly extracted with EA. The combined organic phases were dried over MgSO4, filtered and evaporated under a vacuum. 87 mg (0.21 mmol, 44%) of 3-(tert-butylamino)-2-(5-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazine-8-carboxylic acid were obtained by crystallisation of the group from DCM/hexane (1:2).

Example 141
Synthesis of N-tert-butyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrimidin-3-amine

A solution of 222 mg (2.34 mmol) of 2-aminopyrimidine, 499 mg (2.34 mmol) of 5-pyridin-2-ylethynyl-thiophene-2-carbaldehyde, 195 mg (2.34 mmol) of tert.-butyl-isonitrile and 234 μl of a 20% aq. perchloric acid in chloroform (20 ml) was stirred at 47° C. for 3 d. The mixture was then diluted with DCM and combined with a 1M aq. Na2CO3 solution. The phases were separated and the organic phase was washed with a sat. NaCl solution and dried over MgSO4. After filtration and removal of the solvents under a vacuum, CC (EA) was carried out with the group, 80 mg (0.21 mmol, 9%) of N-tert-butyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrimidin-3-amine being obtained.

Example 143
Synthesis of N-tert-butyl-N-methyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine

43 mg (1.08 mmol, 60% in mineral oil) of sodium hydride were added to a solution of 135 mg (0.36 mmol) of tert-butyl-[2-(5-pyridin-2-ylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine (Example 77) in DMF (3 ml) and the mixture was stirred at RT for 1 h. A solution of 67 μl (1.08 mmol) of methyl iodide in DMF (500 μl) was then added dropwise thereto and the mixture stirred at RT for a further 16 h. A further 43 mg (1.08 mmol, 60% in mineral oil) of sodium hydride and a solution of 67 μl (1.08 mmol) of methyl iodide in DMF (500 μl) were then added and the mixture stirred at RT for a further 16 h. The reaction solution was combined in succession with water, a 1M aq. Na2CO3 solution and a mixture of EA/THF (3:1). The organic phase was separated off and the aq. phase was extracted with EA. The combined organic phases were dried over MgSO4, filtered and evaporated under a vacuum. 33 mg (0.09 mmol, 24%) of N-tert-butyl-N-methyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine were obtained by CC (acetone/MeCN 1:1).

Example 156
Synthesis of N-tert-butyl-2-(5-(thiophen-3-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride

94 mg (0.5 mmol) of copper(I) iodide, 129 mg (0.5 mmol) of triphenylphosphine, 1.32 ml (9.5 mmol) of NEt3, 701 mg (1.9 mmol) of tetra-n-butyl-ammonium iodide and 173 mg (0.25 mmol) of bis(triphenylphosphine)-palladium(II) chloride were added to a solution of 699 mg (1.9 mmol) of tert-butyl-[2-(5-trimethylsilanylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine (synthesis described in Example 158, part a) and 402 mg (2.5 mmol) of 3-bromo-thiophene in DMF (20 ml). 2.5 ml (2.5 mmol) of a 1M solution of tetra-n-butyl-ammonium fluoride in THF were added dropwise to the reaction solution over a period of 1 h. The mixture was then stirred at 70° C. for 18 h. After cooling to RT, the mixture was diluted with EA and combined with a 0.5M aq. Na2CO3 solution. The phases were separated and the aq. phase was extracted with EA. The combined organic phases were dried over MgSO4, filtered and evaporated under a vacuum. CC (acetonitrile/EA 1:3) was carried out with the group, 912 mg of slightly contaminated product being isolated. 304 mg (0.73 mmol, 38%) of N-tert-butyl-2-(5-(thiophen-3-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride were obtained by hydrochloride precipitation in accordance with the method described in Example 192.

Example 158
N-tert-butyl-2-(5-((6-methylpyridin-2-yl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride

a) Synthesis of tert-butyl-[2-(5-trimethylsilanylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine

21.4 ml (155 mmol) of trimethylsilylacetylene, 2.4 g (12.9 mmol) of copper(I) iodide and 4.5 g (6.5 mmol) of bis(triphenylphosphine)-palladium(II) chloride were added to a solution of 45.3 g (129 mmol) of [2-(5-bromo-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-tert-butyl-amine (synthesis described in Example 18, part a) in DMF (760 ml) and NEt3 (90 ml). The reaction solution was heated to 60° C. for 4 h and stirred at RT for 16 h. The mixture was then combined with a 1M aq. Na2CO3 solution and diluted with EA. The phases were separated and the aq. phase was extracted with EA. The combined organic phases were washed with water and dried over MgSO4. After filtration and removal of the solvents under a vacuum, the resultant group was redissolved with an EA/DCM (1:1) mixture and filtered through diatomaceous earth. The filtrate was evaporated under a vacuum. 30.8 g (84 mmol, 65%) of tert-butyl-[2-(5-trimethylsilanylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine were obtained from the group were by crystallisation from tert.-butyl-methyl ether.

b) Synthesis of tert-butyl-[2-(5-ethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine

A solution of 14.0 g (38.0 mmol) of tert-butyl-[2-(5-trimethylsilanylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine in a mixture of MeOH (385 ml) and MeCN (440 ml) was combined with 417 ml (41.8 mmol) of a 0.1M aq. NaOH solution. The reaction solution was stirred at RT for 1 h. The solvents were then largely removed under a vacuum. The resultant aq. solution was repeatedly extracted with EA and the combined organic phases were dried over MgSO4, filtered and evaporated under a vacuum, 11.1 g (37.4 mmol, 99%) of tert-butyl-[2-(5-ethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine being obtained.

c) Synthesis of N-tert-butyl-2-(5-((6-methylpyridin-2-yl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine

300 mg (1.0 mmol) of tert-butyl-[2-(5-ethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine were dissolved together with 138 μl (1.2 mmol) of 2-bromo-6-methyl-pyridine in DMF (7 ml). 1.4 ml (10.0 mmol) of NEt3, 19 mg (0.1 mmol) of copper(I) iodide and 71 mg (0.1 mmol) bis(triphenylphosphine)-palladium(II) chloride were added to this solution. The reaction mixture was heated to 50° C. for 6 h. The mixture was then diluted with EA and combined with a 1M aq. Na2CO3 solution. The phases were separated and the aq. phase was extracted with EA. The combined organic phases were dried over MgSO4, filtered and evaporated under a vacuum. 166 mg (0.42 mmol, 42%) of N-tert-butyl-2-(5-((6-methylpyridin-2-yl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine were obtained by CC (acetone/MeCN 1:1) of the group.

d) Synthesis of N-tert-butyl-2-(5-((6-methylpyridin-2-yl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride

115 mg (0.27 mmol, 65%) of N-tert-butyl-2-(5-((6-methylpyridin-2-yl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride were obtained from 161 mg (0.42 mmol) of N-tert-butyl-2-(5-((6-methylpyridin-2-yl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine in accordance with the method described in Example 192.

Example 165
Synthesis of N-tert-butyl-2-(5-((6-fluoropyridin-2-yl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine

500 mg (1.69 mmol) of tert-butyl-[2-(5-ethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine (synthesis described in Example 158 part b) were dissolved together with 355 mg (2.02 mmol) of 2-bromo-6-fluoro-pyridine in DMF (20 ml). 2.4 ml (16.9 mmol) of NEt3, 32 mg (0.17 mmol) of copper(I) iodide and 119 mg (0.17 mmol) bis(triphenylphosphine)-palladium(II) chloride were added to this solution. The reaction mixture was heated to 50° C. for 6 h. The mixture was then diluted with EA and combined with a 1M aq. Na2CO3 solution. The phases were separated and the aq. phase was extracted with EA. The combined organic phases were washed with a 1M aq. Na2CO3 solution, dried over MgSO4, filtered and evaporated under a vacuum. 200 mg (0.51 mmol, 30%) of N-tert-butyl-2-(5-((6-fluoropyridin-2-yl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine were obtained by CC (EA) of the group.

Example 176
Synthesis of N-tert-butyl-2-(5-(phenylethynyl)thiazol-2-yl)imidazo[1,2-a]pyrazin-3-amine

A solution of 290 mg (3.0 mmol) of 2-aminopyrazine, 650 mg (3.0 mmol) of 5-pyridin-2-ylethynyl-thiazole-2-carbaldehyde, 344 μl (3.0 mmol) of tert.-butyl-isonitrile and 305 μl of a 20% aq. perchloric acid in DCM (6 ml) was stirred at RT for 6 d. The mixture was then diluted with ether and the phases were separated. The organic phase was washed with water and dried over MgSO4. After filtration and removal of the solvents under a vacuum, CC (hexane/tert.-butyl-methyl ether 3:2) was carried out with the group, 170 mg (0.46 mmol, 15%) of N-tert-butyl-2-(5-(phenylethynyl)thiazol-2-yl)imidazo[1,2-a]pyrazin-3-amine being obtained.

Example 192
Synthesis of N-tert-butyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine hydrochloride

A solution of 6.93 g (18.6 mmol) of N-tert-butyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine (Example 94) in DCM (180 ml) was combined with 335 μl (18.6 mmol) of water and 2.35 ml (18.6 mmol) of chlorotrimethylsilane and stirred at RT for 16 h. The resultant precipitate was filtered out and dried under a vacuum at 40° C., 6.09 g (14.8 mmol, 80%) of N-tert-butyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine hydrochloride being obtained.

Example 331
tert-Butyl-[2-(5-pyridin-2-ylethynyl-thiophen-2-yl)-imidazo[1,2-b]pyridazin-3-yl]-amine hydrochloride

a) Synthesis of [2-(5-bromo-thiophen-2-yl)-imidazo[1,2-b]pyridazin-3-yl]-tert-butyl-amine

13.1 g (158 mmol) of tert.-butyl-isonitrile, 30.2 g (158 mmol) of 5-bromo-thiophene-2-carboxaldehyde and 5.2 g of a 20% aq. perchloric acid solution were added to a solution of 15.0 g (158 mmol) of 3-amino-pyridazine in DCM (150 ml). The reaction solution was stirred at 40° C. for 5 hours. The mixture was then combined with water (200 ml) and the phases were separated. The aq. phase was extracted with DCM. The combined organic phases were washed in succession with a sat. NaHCO3 solution and a sat. aq. NaCl solution, dried over Na2SO4, filtered and evaporated under a vacuum. CC (alumina, EA/hexane 2:98) was carried out with the group, 1.7 g (4.8 mmol, 3%) of [2-(5-bromo-thiophen-2-yl)-imidazo[1,2-b]pyridazin-3-yl]-tert-butyl-amine being obtained.

b) Synthesis of tert-butyl-[2-(5-pyridin-2-ylethynyl-thiophen-2-yl)-imidazo[1,2-b]pyridazin-3-yl]-amine hydrochloride

0.42 ml (7.4 mmol) of 2-ethynylpyridine, 7.9 ml (57.0 mmol) of NEt3, 280 mg (0.26 mmol) of copper(I) iodide and 519 mg (0.74 mmol) of bis(triphenylphosphine)-palladium(II) chloride were added to a solution of 2.0 g (5.7 mmol) of [2-(5-bromo-thiophen-2-yl)-imidazo[1,2-b]pyridazin-3-yl]-tert-butyl-amine in DMF (50 ml). The reaction solution was heated to 50° C. for 6 h. The mixture was then diluted with EA and combined with a 1M aq. Na2CO3 solution. The phases were separated and the aq. phase was extracted with EA. The combined organic phases were dried over MgSO4, filtered and evaporated under a vacuum. 546 mg of amine were obtained by CC (EA) with the group. Using the method described in Example 192, 440 mg (1.1 mmol, 19%) of tert-butyl-[2-(5-pyridin-2-ylethynyl-thiophen-2-yl)-imidazo[1,2-b]pyridazin-3-yl]-amine hydrochloride were produced therefrom.

Example 332
tert-Butyl-[2-(5-thiazol-2-ylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-amine hydrochloride

a) Synthesis of [2-(5-bromo-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-tert-butyl-amine

A solution of 32.3 g (343.4 mmol) of 2-aminopyridine, 37.2 ml (343.4 mmol) of 5-pyridin-2-ylethynyl-thiophene-2-carbaldehyde, 28.6 g (343.4 mmol) of tert.-butyl-isonitrile and 34.3 ml of a 20% aq. perchloric acid in DCM (660 ml) was stirred at RT for 10 d. The reaction solution was then diluted with DCM and washed in succession with a 1M aq. Na2CO3 solution and a sat. aq. NaCl solution. The organic phase was dried over MgSO4, filtered and evaporated under a vacuum. 56.3 g (160.7 mmol, 47%) of [2-(5-bromo-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-tert-butyl-amine were obtained from the group by crystallisation from EA.

b) Synthesis of tert-butyl-[2-(5-trimethylsilanylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-amine

5.0 ml (36.0 mmol) of trimethylsilylacetylene, 0.57 g (3.0 mmol) of copper(I) iodide and 2.1 g (3.0 mmol) of bis(triphenylphosphine)-palladium(II) chloride were added to a solution of 10.5 g (30.0 mmol) of [2-(5-bromo-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-tert-butyl-amine in DMF (180 ml) and NEt3 (21 ml). The reaction solution was stirred at 50° C. for 16 hours. The mixture was then combined with a 1M aq. Na2CO3 solution and diluted with EA. This mixture was filtered through diatomaceous earth. The phases were then separated and the aq. phase was extracted with EA. The combined organic phases were dried over MgSO4, filtered and evaporated under a vacuum. CC (EA/DCM 1:1) was carried out with the group, 8.0 g (21.8 mmol, 73%) of tert-butyl-[2-(5-trimethylsilanylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-amine being obtained.

c) Synthesis of tert-butyl-[2-(5-ethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-amine

11.5 g (31.3 mmol) of tert-butyl-[2-(5-trimethylsilanylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-amine were dissolved in a mixture of MeOH (230 ml) and DCM (50 ml) and combined with 431 mg (3.13 mmol) of potassium carbonate The reaction solution was stirred at RT for 30 min and then combined with water (200 ml). The mixture was then extracted with DCM and the organic phase was washed with water and dried over MgSO4. After filtration and evaporation under a vacuum, 9.0 g (30.5 mmol, 97%) of tert-butyl-[2-(5-ethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-amine were obtained.

d) Synthesis of tert-butyl-[2-(5-thiazol-2-ylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-amine hydrochloride

383 μl (4.3 mmol) of 2-bromothiazole, 882 μl (6.36 mmol) of triethylamine, 43 mg (0.23 mmol) of copper(I) iodide and 87 mg (0.13 mmol) of bis(triphenylphosphine)-palladium(II) chloride were added to a solution of 1.0 g (3.4 mmol) of tert-butyl-[2-(5-ethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-amine in EA (20 ml). This reaction solution was stirred at 50° C. for 16 hours. The mixture then filtered through diatomaceous earth and evaporated under a vacuum. CC (EA/DCM 3:7) was carried out with the group, 902 mg (2.4 mmol, (70%) of tert-butyl-[2-(5-thiazol-2-ylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-amine being obtained. Using the method described in Example 192, tert-butyl-[2-(5-thiazol-2-ylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-amine hydrochloride was produced therefrom.

The production, not described in detail above, of the other compounds according to the Examples stated below also proceeded in a similar manner to the above-stated production methods, the educts used in each case being known to the person skilled in the art on the basis of these methods.

Example
Name

1
cyclopentyl-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine

2
cyclohexylmethyl-[5-methyl-2-(5-phenylethynyl-thiophen-2-yl)-

imidazo[1,2-a]pyridin-3-yl]-amine

3
cyclohexylmethyl-[6-methyl-2-(5-phenylethynyl-thiophen-2-yl)-

imidazo[1,2-a]pyridin-3-yl]-amine

4
cyclohexylmethyl-[7-methyl-2-(5-phenylethynyl-thiophen-2-yl)-

imidazo[1,2-a]pyridin-3-yl]-amine

5
cyclohexylmethyl-[8-methyl-2-(5-phenylethynyl-thiophen-2-yl)-

imidazo[1,2-a]pyridin-3-yl]-amine

6
cyclohexylmethyl-[5,7-dimethyl-2-(5-phenylethynyl-thiophen-2-yl)-

imidazo[1,2-a]pyridin-3-yl]-amine

7
[8-benzyloxy-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-

cyclohexylmethyl-amine

8
cyclohexylmethyl-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-

amine

9
cyclohexylmethyl-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrimidin-3-yl]-

amine

10
(4-methoxy-benzyl)-[5-methyl-2-(5-phenylethynyl-thiophen-2-yl)-

imidazo[1,2-a]pyridin-3-yl]-amine

11
(4-methoxy-benzyl)-[6-methyl-2-(5-phenylethynyl-thiophen-2-yl)-

imidazo[1,2-a]pyridin-3-yl]-amine

12
(4-methoxy-benzyl)-[7-methyl-2-(5-phenylethynyl-thiophen-2-yl)-

imidazo[1,2-a]pyridin-3-yl]-amine

13
(4-methoxy-benzyl)-[8-methyl-2-(5-phenylethynyl-thiophen-2-yl)-

imidazo[1,2-a]pyridin-3-yl]-amine

14
[5,7-dimethyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(4-

methoxy-benzyl-amine

15
[8-benzyloxy-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(4-

methoxy-benzyl)-amine

16
(4-methoxy-benzyl)-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-

amine

17
(4-methoxy-benzyl)-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-

amine

18
tert-Butyl-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine

19
tert-butyl-[6-methyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-

amine

20
[8-benzyloxy-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(3-

methoxy-phenyl)-amine

21
(3-methoxy-benzyl)-[5-methyl-2-(5-phenylethynyl-thiophen-2-yl)-

imidazo[1,2-a]pyridin-3-yl]-amine

22
(3-methoxy-benzyl)-[8-methyl-2-(5-phenylethynyl-thiophen-2-yl)-

imidazo[1,2-a]pyridin-3-yl]-amine

23
[5,7-dimethyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(3-

methoxy-benzyl)-amine

24
[8-benzyloxy-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(3-

methoxy-benzyl)-amine

25
(3-methoxy-benzyl)-[2-(5-phenylethyyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-

amine

26
(3-methoxy-benzyl)-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-

amine

27
[6-methyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(1-phenyl-

ethyl)-amine

28
[7-methyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(1-phenyl-

ethyl)-amine

29
[5,7-dimethyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(1-

phenyl-ethyl)-amine

30
[8-benzyloxy-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(1-

phenyl-ethyl)-amine

31
(1-phenyl-ethyl)-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-

amine

32
(2-chloro-benzyl)-[5,7-dimethyl-2-(5-phenylethynyl-thiophen-2-yl)-

imidazo[1,2-a]pyridin-3-yl]-amine

33
(3-chloro-4-fluoro-phenyl)-[7-phenyl-2-(5-phenylethynyl-thiophen-2-yl)-

imidazo[1,2-a]pyridin-3-yl]-amine

34
(4-methoxy-benzyl)-[7-methyl-2-(5-phenylethynyl-thiophen-2-yl)-

imidazo[1,2-a]pyrimidin-3-yl]-amine

35
[8-methyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(1-phenyl-

ethyl)-amine

36
[7-methyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrimidin-3-yl]-(1-

phenyl-ethyl)-amine

37
(2-methoxy-benzyl)-[7-methyl-2-(5-phenylethynyl-thiophen-2-yl)-

imidazo[1,2-a]pyridin-3-yl]-amine

38
(2-methoxy-benzyl)-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-

amine

39
(2-chloro-benzyl)-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-

amine

40
(2-methoxy-benzyl)-[7-methyl-2-(5-phenylethynyl-thiophen-2-yl)-

imidazo[1,2-a]pyrimidin-3-yl]-amine

41
(3-methoxy-phenyl)-[6-methyl-2-(5-phenylethynyl-thiophen-2-yl)-

imidazo[1,2-a]pyridin-3-yl]-amine

42
[5,7-dimethyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(3-

methoxy-phenyl)-amine

43
(3-methoxy-phenyl)-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-

amine

44
[7-ethyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(2-methoxy-

benzyl)-amine

45
(2-chloro-benzyl)-[7-ethyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-

3-yl]-amine

46
[7-tert-butyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(3-

chloro-4-fluoro-phenyl)-amine

47
(3-methoxy-benzyl)-[7-methyl-2-(5-phenylethynyl-thiophen-2-yl)-

imidazo[1,2-a]pyrimidin-3-yl]-amine

48
[7-ethyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(2-fluoro-

phenyl)-amine

49
[7-tert-butyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(2-fluoro-

phenyl)-amine

50
(2,4-difluoro-phenyl)-[2-(5-phenylethynyl-thiophen-2-yl)-7-(3-phenyl-propyl)-

imidazo[1,2-a]pyridin-3-yl]-amine

51
(4-fluoro-benzyl)-[7-methyl-2-(5-phenylethynyl-thiophen-2-yl)-

imidazo[1,2-a]pyridin-3-yl]-amine

52
[5,7-dimethyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(4-

fluoro-benzyl)-amine

53
[7-ethyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(3-

trifluoromethyl-benzyl)-amine

54
[7-isopropyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(3-

trifluoromethyl-benzyl)-amine

55
tert-butyl-[2-(4-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine

56
[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-(1,1,3,3-tetramethyl-

butyl)-amine

57
butyl-[2-(4-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine

59
[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(1,1,3,3-tetramethyl-

butyl)-amine

60
[2-(5-pyridin-3-ylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-(1,1,3,3-

tetramethyl-butyl)-amine

61
[2-(5-pyridin-4-ylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-

(1,1,3,3-tetramethyl-butyl)-amine

62
[6-chloro-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(1,1,3,3-

tetramethyl-butyl)-amine

63
[6,8-dichloro-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(1,1,3,3-

tetramethyl-butyl)-amine

64
[2-(5-pyridin-2-ylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-

(1,1,3,3-tetramethyl-butyl)-amine

65
dimethyl-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine

66
methyl-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine

67
N-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-acetamide

68
ethyl-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine

69
propyl-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine

70
butyl-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine

71
(2-methylpropyl)-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-

amine

72
pentyl-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine

73
{(methoxycarbonylmethyl)-[2-(5-phenylethynyl-thiophen-2-yl)-

imidazo[1,2-a]pyrazin-3-yl]-amino}-acetic acid methyl ester

74
benzyl-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine

75
[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-ylamino]-acetic acid

methyl ester

76
tert-butyl-[2-(5-pyridin-4-ylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine

77
tert-butyl-[2-(5-pyridin-2-ylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine

78
N-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-benzamide

79
[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-bis-pyridine-3-

ylmethyl-amine

80
2,2-dimethyl-N-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-

propionamide

81
3-methoxy-N-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-

benzamide

82
tert-butyl-[2-(5-pyridin-3-ylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine

83
2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-ylamine

84
methyl-2-(5-(phenylethynyl)thiophen-2-yl)-3-(2,4,4-trimethylpentan-2-

ylamino)imidazo[1,2-a]pyrazine-8-carboxylate

85
2-(5-(phenylethynyl)thiophen-2-yl)-N-(2,4,4-trimethylpentan-2-

yl)imidazo[1,2-a]pyrimidin-3-amine

86
2-(5-((6-methylpyridin-2-yl)ethynyl)thiophen-2-yl)-N-(2,4,4-trimethylpentan-2-

yl)imidazo[1,2-a]pyrazin-3-amine

87
N-cyclohexyl-2-(5-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine

88
2-(5-(phenylethynyl)thiophen-2-yl)-3-(piperidin-1-yl)imidazo[1,2-a]pyrazine

89
N-tert-butyl-N-methyl-2-(5-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-

amine

90
methyl-2-(5-(phenylethynyl)thiophen-2-yl)-3-(2,4,4-trimethylpentan-2-

ylamino)imidazo[1,2-a]pyridine-6-carboxylate

91
N-tert-butyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine

hydrochloride

92
8-bromo-N-cyclopentyl-6-methyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-

yl)imidazo[1,2-a]pyridin-3-amine

93
N,N-diethyl-2-(5-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine

94
N-tert-butyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine

95
N-tert-butyl-2-(5-(phenylethynyl)furan-2-yl)imidazo[1,2-a]pyrazin-3-amine

96
8-bromo-N-tert-butyl-6-methyl-2-(3-(pyridin-2-ylethynyl)phenyl)imidazo-

[1,2-a]pyridin-3-amine

97
N-tert-butyl-8-methyl-2-(5-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-

98
N-methyl-2-(5-(phenylethynyl)thiophen-2-yl)-N-(2,4,4-trimethylpentan-2-

yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride

99
2-(5-(phenylethynyl)thiophen-2-yl)-3-(pyrrolidin-1-yl)imidazo[1,2-a]pyrazine

hydrochloride

100
N-tert-butyl-2-(5-((4-fluorophenyl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-

amine hydrochloride

101
N-tert-butyl-7-methyl-2-(5-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-

amine

102
N-tert-butyl-5-methyl-2-(5-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-

amine

103
8-chloro-2-(3-(pyridin-2-ylethynyl)phenyl)-6-(trifluoromethyl)-N-(2,4,4-

trimethylpentan-2-yl)imidazo[1,2-a]pyridin-3-amine

104
N-tert-butyl-2-(5-((3-fluorophenyl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-

amine hydrochloride

105
N-tert-butyl-2-(5-((2-fluorophenyl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-

amine hydrochloride

106
methyl-3-(tert-butylamino)-2-(5-(phenylethynyl)thiophen-2-yl)imidazo-

[1,2-a]pyrazine-8-carboxylate

107
N-tert-butyl-2-(5-(pyrazin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine

108
2-(5-((4-aminophenyl)ethynyl)thiophen-2-yl)-N-tert-butylimidazo[1,2-a]pyrazin-3-

amine

109
N-isopropyl-2-(5-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine

110
N-tert-butyl-2-(5-(thiophen-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-

amine hydrochloride

111
N-tert-butyl-2-(3-(pyridine-2-ylethynyl)phenyl)imidazo[1,2-a]pyrazin-3-amine

112
N-tert-butyl-2-(5-((2-methoxyphenyl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-

amine hydrochloride

113
N-tert-butyl-2-(5-((3-methoxyphenyl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-

3-amine hydrochloride

114
N-tert-butyl-2-(5-((4-methoxyphenyl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-

amine hydrochloride

115
N-tert-butyl-2-(5-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]quinolin-1-amine

116
N-tert-butyl-2-(4-(pridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyrazin-3-amine

117
N-tert-butyl-2-(3-((6-methylpyridin-2-yl)ethynyl)phenyl)imidazo[1,2-a]pyrazin-3-

amine

118
N-tert-butyl-2-(2-methyl-6-(phenylethynyl)pyridin-3-yl)imidazo[1,2-a]pyrazin-3-

amine

119
N-tert-butyl-2-(5-(pyridin-2-ylethynyl)furan-2-yl)imidazo[1,2-a]pyrazin-3-amine

120
3-(tert-butylamino)-2-(5-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazine-8-

carboxylic acid

121
4-((5-(3-(tert-butylamino)imidazo[1,2-a]pyrazin-2-yl)thiophen-2-yl)ethynyl)phenol

hydrochloride

122
3-((5-(3-(tert-butylamino)imidazo[1,2-a]pyrazin-2-yl)thiophen-2-yl)ethynyl)phenol

123
2-(5-((3-aminophenyl)ethynyl)thiophen-2-yl)-N-tert-butylimidazo[1,2-a]pyrazin-3-

amine hydrochloride

124
2-(5-((2-aminophenyl)ethynyl)thiophen-2-yl)-N-tert-butylimidazo[1,2-a]pyrazin-3-

amine hydrochloride

125
N-tert-butyl-2-(5-(phenylethynyl)thiophen-2-yl)imidazo[2,1-a]isoquinolin-3-amine

126
N-tert-butyl-2-(6-(phenylethynyl)pyridin-3-yl)imidazo[1,2-a]pyrazin-3-amine

127
N-tert-butyl-2-(5-(pyridin-4-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine

hydrochloride

128
2-(5-((6-aminopyridin-3-yl)ethynyl)thiophen-2-yl)-N-tert-butylimidazo[1,2-a]pyrazin-

3-amine hydrochloride

129
N-tert-butyl-2-(5-(pyrimidin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-

amine hydrochloride

130
N-tert-butyl-2-(5-((4-methylpyridin-2-yl)ethynyl)thiophen-2-

yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride

131
N-tert-butyl-2-(5-((5-methylpyridin-2-yl)ethynyl)thiophen-2-yl)imidazo-

[1,2-a]pyrazin-3-amine hydrochloride

132
N-tert-butyl-2-(5-(pyridin-4-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine

hydrochloride

133
N-tert-butyl-2-(5-(thiazol-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine

134
2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine

hydrochloride

135
N-tert-butyl-2-(5-((5-methylthiophen-2-yl)ethylnyl)thiophen-2-yl)imidazo-

[1,2-a]pyrazin-3-amine hydrochloride

136
2-(5-((6-aminopyridin-2-yl)ethynyl)thiophen-2-yl)-N-tert-butylimidazo[1,2-a]pyrazin-

3-amine hydrochloride

137
N-tert-butyl-2-(5-((3-methylthiophen-2-yl)ethynyl)thiophen-2-

yl)-imidazo[1,2-a]pyrazin-3-amine

138
N-tert-butyl-2-(4-(phenylethynyl)thiazol-2-yl)imidazo[1,2-a]pyrazin-3-amine

139
N-tert-butyl-2-(5-(m-tolylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine

140
3-((5-(3-(tert-butylamino)imidazo[1,2-a]pyrazin-2-yl)thiophen-2-

yl)ethynyl)benzonitrile hydrochloride

141
N-tert-butyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrimidin-3-

amine

142
N-tert-butyl-2-(6-(phenylethynyl)pyridin-2-yl)imidazo[1,2-a]pyrazin-3-amine

hydrochloride

143
N-tert-butyl-N-methyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo-

[1,2-a]pyrazin-3-amine

144
4-((5-(3-(tert-butylamino)imidazo[1,2-a]pyrazin-2-yl)thiophen-2-

yl)ethynyl)benzonitrile hydrochloride

145
2-(5-((1H-indol-6-yl)ethynyl)thiophen-2-yl)-N-tert-butylimidazo[1,2-a]pyrazin-3-

amine hydrochloride

146
N-tert-butyl-2-(2-(phenylethynyl)thiazol-5-yl)imidazo[1,2-a]pyrazin-3-amine

147
N-tert-butyl-2-(5-(quinolin-6-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine

hydrochloride

148
2-(5-((3-(1H-pyrrol-1-yl)phenyl)ethynyl)thiophen-2-yl)-N-tert-butylimidazo-

[1,2-a]pyrazin-3-amine hydrochloride

149
2-(5-((1H-indol-4-yl)ethynyl)thiophen-2-yl)-N-tert-butylimidazo[1,2-a]pyrazin-3-

amine hydrochloride

150
N-tert-butyl-2-(5-((3-nitrophenyl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-

amine hydrochloride

151
N-tert-butyl-2-(5-((4-nitrophenyl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-

amine hydrochloride

152
N-tert-butyl-2-(5-(thiazol-4-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine

hydrochloride

153
2-((5-(3-(tert-butylamino)imidazo[1,2-a]pyrazin-2-yl)thiophen-2-yl)ethynyl)phenol

154
2-(5-((3-(aminomethyl)phenyl)ethynyl)thiophen-2-yl)-N-tert-butylimidazo-

[1,2-a]pyrazin-3-amine

155
2-(5-(biphenyl-3-ylethynyl)thiophen-2-yl)-N-tert-butylimidazo[1,2-a]pyrazin-3-

amine hydrochloride

156
N-tert-butyl-2-(5-(thiophen-3-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-

amine hydrochloride

157
N-tert-butyl-2-(5-((3-(dimethylamino)phenyl)ethynyl)thiophen-2-yl)imidazo-

[1,2-a]pyrazin-3-amine hydrochloride

158
N-tert-butyl-2-(5-((6-methylpyridin-2-yl)ethynyl)thiophen-2-yl)imidazo-

[1,2-a]pyrazin-3-amine hydrochloride

159
N-tert-butyl-2-(5-((3-fluoropyridin-2-yl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-

3-amine hydrochloride

160
N-tert-butyl-2-(5-((3-(methylamino)phenyl)ethynyl)thiophen-2-yl)imidazo-

[1,2-a]pyrazin-3-amine hydrochloride

161
N-tert-butyl-2-(5-(p-tolylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine

162
N-tert-butyl-2-(5-(o-tolylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine

hydrochloride

163
N-tert-butyl-2-(4-methyl-5-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-

amine hydrochloride

164
N-tert-butyl-2-(4-methyl-5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-

3-amine hydrochloride

165
N-tert-butyl-2-(5-((6-fluoropyridin-2-yl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-

3-amine

166
N-tert-butyl-2-(5-((2-nitrophenyl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-

amine

167
N-tert-butyl-8-chloro-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-

3-amine

168
N-tert-butyl-2-(5-((6-methoxypyridin-2-yl)ethynyl)thiophen-2-yl)imidazo[1,2-a]-

pyrazin-3-amine

169
N-tert-butyl-2-(5-((5-fluoropyridin-2-yl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-

3-amine hydrochloride

170
2-(4-(3-(tert-butylamino)imidazo[1,2-a]pyrazin-2-yl)-2-(phenylethynyl)-

phenyl)acetonitrile

171
N-tert-butyl-2-(5-((5-methoxypyridin-3-yl)ethynyl)thiophen-2-yl)imidazo-

[1,2-a]pyrazin-3-amine hydrochloride

172
5-((5-(3-(tert-butylamino)imidazo[1,2-a]pyrazin-2-yl)thiophen-2-yl)ethynyl)-

nicotinonitrile hydrochloride

173
N-tert-butyl-2-(5-((3-(methylthio)phenyl)ethynyl)thiophen-2-yl)imidazo-

[1,2-a]pyrazin-3-amine

174
methyl-3-((5-(3-(tert-butylamino)imidazo[1,2-a]pyrazin-2-yl)thiophen-2-

yl)ethynyl)benzoate

175
N-tert-butyl-2-(5-((3,5-difluoropyridin-2-yl)ethynyl)thiophen-2-yl)imidazo-

[1,2-a]pyrazin-3-amine

176
N-tert-butyl-2-(5-(phenylethynyl)thiazol-2-yl)imidazo[1,2-a]pyrazin-3-amine

177
N-tert-butyl-2-(2-(pyridin-4-ylethynyl)thiazol-5-yl)imidazo[1,2-a]pyrazin-3-amine

178
3-((5-(3-(tert-butylamino)imidazo[1,2-a]pyrazin-2-yl)thiophen-2-yl)ethynyl)-

benzaldehyde

179
3-((5-(3-(tert-butylamino)imidazo[1,2-a]pyrazin-2-yl)thiophen-2-yl)ethynyl)-4-

fluorobenzonitrile

180
N-tert-butyl-2-(5-((3-(trifluoromethyl)phenyl)ethynyl)thiophen-2-

yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride

181
N-tert-butyl-2-(2-(pyridin-2-ylethynyl)thiazol-5-yl)imidazo[1,2-a]pyrazin-3-amine

182
N-tert-butyl-2-(3-methyl-5-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-

amine hydrochloride

183
N-tert-butyl-2-(3-methyl-5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-

3-amine hydrochloride

184
N-tert-butyl-2-(5-((3-vinylphenyl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-

amine

185
2-(5-((1H-imidazol-4-yl)ethynyl)thiophen-2-yl)-N-tert-butylimidazo[1,2-a]pyrazin-3-

amine hydrochloride

186
N-tert-butyl-2-(5-((3-methylpyridin-2-yl)ethynyl)thiophen-2-yl)imidazo[1,2-a]-

pyrazin-3-amine

187
N,N-dimethyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-

amine

188
N-tert-butyl-2-(5-((2-(tert-butyldiphenylsilyl)thiazol-5-yl)ethynyl)thiophen-2-

yl)imidazo[1,2-a]pyridin-3-amine

189
3-((5-(3-(tert-butylamino)imidazo[1,2-a]pyridin-2-yl)thiophen-2-yl)ethynyl)-

benzonitrile

190
N-tert-butyl-2-(5-(phenylethynyl)thiazol-2-yl)imidazo[1,2-a]pyrazin-3-amine

191
N-tert-butyl-2-(5-(thiazol-5-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine

192
N-tert-butyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine

hydrochloride

193
6-chloro-N-cyclohexyl-2-(3-((6-methylpyridin-2-yl)ethynyl)phenyl)-

imidazo[1,2-a]pyridin-3-amine

194
5,7-dimethyl-N-phenethyl-2-(5-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]-

pyrimidin-3-amine

195
N-(3-methoxyphenethyl)-5,7-dimethyl-2-(5-(phenylethynyl)thiophen-2-

yl)imidazo[1,2-a]pyrimidin-3-amine

196
N-(3-methoxyphenethyl)-5,7-dimethyl-2-(4-(phenylethynyl)thiophen-2-

yl)imidazo[1,2-a]pyrimidin-3-amine

197
N-(3-methoxyphenethyl)-5,7-dimethyl-2-(5-(phenylethynyl)furan-2-

yl)imidazo[1,2-a]pyrimidin-3-amine

198
N-(4-chlorobenzyl)-8-methyl-2-(5-(phenylethynyl)thiophen-2-yl)imidazo-

[1,2-a]pyridin-3-amine

199
N-(3-methoxyphenethyl)-5-methyl-2-(4-(phenylethynyl)thiopen-2-yl)imidazo-

[1,2-a]pyridin-3-amine

200
N-(2-methylhexan-2-yl)-2-(4-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-

amine

201
N-phenethyl-2-(4-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine

202
N-(3-methoxyphenethyl)-2-(4-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-

3-amine

203
2-(4-(phenylethynyl)thiophen-2-yl)-N-(2-(thiophen-2-yl)ethyl)imidazo[1,2-a]pyrazin-

3-amine

204
N-(4-chlorobenzyl)-2-(5-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-

amine

205
N-(2-methylpentan-2-yl)-2-(5-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-

3-amine

206
N-(cyclohexylmethyl)-2-(4-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-

amine

207
N-(2-methoxybenzyl)-2-(5-(phenylethynyl)furan-2-yl)imidazo[1,2-a]pyrazin-3-

amine

208
N-(cyclohexylmethyl)-2-(4-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-

amine

209
N-(2-methylpentan-2-yl)-2-(4-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-

amine

210
8-bromo-6-methyl-2-(3-((6-methylpyridin-2-yl)ethynyl)phenyl)-N-(2,4,4-

trimethylpentan-2-yl)imidazo[1,2-a]pyridin-3-amine

211
8-bromo-N-cyclopentyl-6-methyl-2-(3-(pyridin-2-ylethynyl)phenyl)imidazo-

[1,2-a]pyridin-3-amine

212
N-cyclopentyl-2-(4-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine

213
N-(1-phenylethyl)-2-(4-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-

amine

214
N-(2-methylpentan-2-yl)-2-(4-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-

3-amine

215
8-bromo-N-cyclohexyl-6-methyl-2-(5-(pyridin-2-ylethynyl)furan-2-yl)imidazo-

[1,2-a]pyridin-3-amine

216
N-cyclopentyl-2-(5-(phenylethynyl)furan-2-yl)imidazo[1,2-a]pyrazin-3-amine

217
N-(3-methoxyphenethyl)-7-methyl-2-(4-(phenylethynyl)thiophen-2-

yl)imidazo[1,2-a]pyrimidin-3-amine

218
8-(benzyloxy)-2-(5-(phenylethynyl)thiophen-2-yl)-N-(2,4,4-trimethylpentan-2-

yl)imidazo[1,2-a]pyridin-3-amine

219
8-(benzyloxy)-N-cyclopentyl-2-(4-(phenylethynyl)thiophen-2-yl)imidazo-

[1,2-a]pyridin-3-amine

220
8-(benzyloxy)-N-(2-methylpentan-2-yl)-2-(4-(phenylethynyl)thiophen-2-yl)-

imidazo[1,2-a]pyridin-3-amine

221
6-chloro-N-(4-fluorobenzyl)-2-(5-(phenylethynyl)furan-2-yl)imidazo[1,2-a]pyridin-3-

amine

222
6-bromo-N-butyl-5-methyl-2-(4-(phenylethynyl)thiophen-2-yl)imidazo-

[1,2-a]pyridin-3-amine

223
N-(furan-2-yl)-8-methyl-2-(5-(phenylethynyl)furan-2-yl)imidazo[1,2-a]pyridin-3-

amine

224
N-(furan-2-yl)-2-(5-(phenylethynyl)furan-2-yl)imidazo[1,2-a]pyridin-3-amine

225
N-(furan-2-yl)-2-(5-(phenylethynyl)furan-2-yl)-7-propylimidazo[1,2-a]pyridin-3-

amine

226
5,7-dimethyl-2-(4-(phenylethynyl)thiophen-2-yl)-N-(3-

(trifluoromethyl)phenyl)imidazo[1,2-a]pyrimidin-3-amine

227
6-bromo-N-(4-chlorophenethyl)-8-methyl-2-(4-(phenylethynyl)thiophen-2-

yl)imidazo[1,2-a]pyridin-3-amine

228
N-(4-chlorophenethyl)-7-phenyl-2-(4-(phenylethynyl)thiophen-2-yl)imidazo-

[1,2-a]pyridin-3-amine

229
N-phenethyl-7-phenyl-2-(4-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-

amine

230
N-(4-chlorobenzyl)-5,7-dimethyl-2-(4-(phenylethynyl)thiophen-2-yl)imidazo-

[1,2-a]pyridin-3-amine

231
6-bromo-N-(4-chlorobenzyl)-5-methyl-2-(4-(phenylethynyl)thiophen-2-

yl)imidazo[1,2-a]pyridin-3-amine

232
8-bromo-N-(4-chlorobenzyl)-6-methyl-2-(4-(phenylethynyl)thiophen-2-yl)imidazo-

[1,2-a]pyridin-3-amine

233
N-(3-methoxyphenethyl)-2-(4-(phenylethynyl)thiophen-2-yl)-5-

propylimidazo[1,2-a]pyridin-3-amine

234
6-bromo-8-methyl-2-(4-(phenylethynyl)thiophen-2-yl)-N-(2-(thiophen-2-

yl)ethyl)imidazo[1,2-a]pyridin-3-amine

235
7-phenyl-2-(4-(phenylethynyl)thiophen-2-yl)-N-(2-(thiophen-2-yl)ethyl)imidazo-

[1,2-a]pyridin-3-amine

236
6,8-dibromo-N-(2-methylpentan-2-yl)-2-(5-(phenylethynyl)thiophen-2-yl)imidazo-

[1,2-a]pyridin-3-amine

237
6-bromo-N-(2,6-dimethylphenyl)-8-methyl-2-(4-(phenylethynyl)thiophen-2-yl)-

imidazo[1,2-a]pyridin-3-amine

238
N-cyclohexyl-2-(3-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyrazin-3-amine

239
2-(3-(pyridin-2-ylethynyl)phenyl)-N-(2,4,4-trimethylpentan-2-yl)imidazo-

[1,2-a]pyrazin-3-amine

240
N-cyclopentyl-2-(4-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyrazin-3-amine

241
8-chloro-2-(4-(pyridin-2-ylethynyl)phenyl)-6-(trifluoromethyl)-N-(2,4,4-

trimethylpentan-2-yl)imidazo[1,2-a]pyridin-3-amine

242
N-(4-fluorophenyl)-2-(4-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyrazin-3-amine

243
N-cyclopentyl-2-(2-methyl-6-(phenylethynyl)pyridin-3-yl)imidazo[1,2-a]pyrazin-3-

amine

244
N-cyclohexyl-2-(2-methyl-6-(phenylethynyl)pyridin-3-yl)imidazo[1,2-a]pyrazin-3-

amine

245
N-cyclopentyl-2-(5-(pyridin-2-ylethynyl)furan-2-yl)imidazo[1,2-a]pyrazin-3-amine

246
8-bromo-N-cyclopentyl-6-methyl-2-(5-(pyridin-2-ylethynyl)furan-2-yl)imidazo-

[1,2-a]pyridin-3-amine

247
N-cyclohexyl-2-(5-(pyridin-2-ylethynyl)furan-2-yl)imidazo[1,2-a]pyrazin-3-amine

248
2-(5-(pyridin-2-ylethynyl)furan-2-yl)-N-(2,4,4-trimethylpentan-2-yl)imidazo-

[1,2-a]pyrazin-3-amine

249
N-cyclopentyl-2-(3-((6-methylpyridin-2-yl)ethynyl)phenyl)imidazo[1,2-a]pyrazin-3-

amine

250
8-bromo-N-cyclopentyl-6-methyl-2-(4-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]-

pyridin-3-amine

251
N-cyclohexyl-2-(3-((6-methylpyridin-2-yl)ethynyl)phenyl)imidazo[1,2-a]pyrazin-3-

amine

252
N-(4-fluorophenyl)-2-(3-((6-methylpyridin-2-yl)ethynyl)phenyl)imidazo[1,2-a]-

pyrazin-3-amine

253
2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)-N-(2,4,4-trimethylpentan-2-yl)imidazo-

[1,2-a]pyrimidin-3-amine

254
N-cyclohexyl-2-(3-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyrimidin-3-amine

255
2-(3-(pyridin-2-ylethynyl)phenyl)-N-(2,4,4-trimethylpentan-2-yl)imidazo-

[1,2-a]pyrimidin-3-amine

256
2-(6-(phenylethynyl)pyridin-3-yl)-N-(2,4,4-trimethylpentan-2-yl)imidazo-

[1,2-a]pyrimidin-3-amine

257
N-cyclopentyl-2-(5-(pyridin-2-ylethynyl)furan-2-yl)imidazo[1,2-a]pyrimidin-3-amine

258
N-tert-butyl-2-(5-(pyridin-2-ylethynyl)furan-2-yl)imidazo[1,2-a]pyrimidin-3-amine

259
N-cyclopentyl-2-(3-((6-methylpyridin-2-yl)ethynyl)phenyl)imidazo[1,2-a]pyrimidin-

3-amine

260
N-cyclopentyl-2-(3-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyridin-3-amine

261
N-tert-butyl-2-(3-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyridin-3-amine

262
2-(3-(pyridin-2-ylethynyl)phenyl)-N-(2,4,4-trimethylpentan-2-yl)imidazo[1,2-a]-

pyridin-3-amine

263
N-(4-fluorophenyl)-2-(3-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyridin-3-amine

264
N-tert-butyl-2-(4-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyridin-3-amine

265
N-cyclopentyl-2-(2-methyl-6-(phenylethynyl)pyridin-3-yl)imidazo[1,2-a]pyridin-3-

amine

266
N-(4-fluorophenyl)-2-(2-methyl-6-(phenylethynyl)pyridin-3-yl)imidazo[1,2-a]pyridin-

3-amine

267
N-cyclopentyl-6-methyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]-

pyridin-3-amine

268
N-tert-butyl-6-methyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-

3-amine

269
N-cyclohexyl-6-methyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]-

pyridin-3-amine

270
6-methyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)-N-(2,4,4-trimethylpentan-2-

yl)imidazo[1,2-a]pyridin-3-amine

271
6-methyl-2-(2-methyl-6-(phenylethynyl)pyridin-3-yl)-N-(2,4,4-trimethylpentan-2-

yl)imidazo[1,2-a]pyridin-3-amine

272
N-cyclopentyl-6-methyl-2-(5-(pyridin-2-ylethynyl)furan-2-yl)imidazo[1,2-a]pyridin-3-

amine

273
N-cyclohexyl-6-methyl-2-(3-((6-methylpyridin-2-yl)ethynyl)phenyl)imidazo[1,2-a]-

pyridin-3-amine

274
N-cyclohexyl-7-methyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]-

pyridin-3-amine

275
7-methyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)-N-(2,4,4-trimethylpentan-2-

yl)imidazo[1,2-a]pyridin-3-amine

276
N-tert-butyl-7-methyl-2-(3-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyridin-3-

amine

277
N-(4-fluorophenyl)-7-methyl-2-(3-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyridin-

3-amine

278
N-tert-butyl-7-methyl-2-(4-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyridin-3-

amine

279
N-(4-fluorophenyl)-7-methyl-2-(5-(pyridin-2-ylethynyl)furan-2-yl)imidazo[1,2-a]-

pyridin-3-amine

280
N-cyclohexyl-8-methyl-2-(6-(phenylethynyl)pyridin-3-yl)imidazo[1,2-a]pyridin-3-

amine

281
N-cyclopentyl-2-(6-(phenylethynyl)pyridin-3-yl)imidazo[1,2-a]pyridin-3-amine

282
N-tert-butyl-2-(6-(phenylethynyl)pyridin-3-yl)imidazo[1,2-a]pyridin-3-amine

283
N-cyclohexyl-2-(6-(phenylethynyl)pyridin-3-yl)imidazo[1,2-a]pyridin-3-amine

284
2-(6-(phenylethynyl)pyridin-3-yl)-N-(2,4,4-trimethylpentan-2-

yl)imidazo[1,2-a]pyridin-3-amine

285
N-tert-butyl-2-(5-(pyridin-2-ylethynyl)furan-2-yl)imidazo[1,2-a]pyridin-3-amine

286
N-cyclohexyl-2-(5-(pyridin-2-ylethynyl)furan-2-yl)imidazo[1,2-a]pyridin-3-amine

287
N-(4-fluorophenyl)-2-(5-(pyridin-2-ylethynyl)furan-2-yl)imidazo[1,2-a]pyridin-3-

amine

288
N-cyclohexyl-2-(3-((6-methylpyridin-2-yl)ethynyl)phenyl)imidazo[1,2-a]pyridin-3-

amine

289
2-(3-((6-methylpyridin-2-yl)ethynyl)phenyl)-N-(2,4,4-trimethylpentan-2-

yl)imidazo[1,2-a]pyridin-3-amine

290
N-tert-butyl-5-methyl-2-(3-((6-methylpyridin-2-yl)ethynyl)phenyl)imidazo-

[1,2-a]pyridin-3-amine

291
5-methyl-2-(3-((6-methylpyridin-2-yl)ethynyl)phenyl)-N-(2,4,4-trimethylpentan-2-

yl)imidazo[1,2-a]pyridin-3-amine

292
N-cyclohexyl-5,7-dimethyl-2-(3-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]-

pyrimidin-3-amine

293
N-cyclohexyl-5,7-dimethyl-2-(2-methyl-6-(phenylethynyl)pyridin-3-yl)imidazo-

[1,2-a]pyrimidin-3-amine

294
N-cyclopentyl-5,7-dimethyl-2-(5-(pyridin-2-ylethynyl)furan-2-yl)imidazo-

[1,2-a]pyrimidin-3-amine

295
N-tert-butyl-5,7-dimethyl-2-(5-(pyridin-2-ylethynyl)furan-2-yl)imidazo-

[1,2-a]pyrimidin-3-amine

296
N-(4-fluorophenyl)-8-methyl-2-(3-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyridin-

3-amine

297
N-cyclohexyl-8-methyl-2-(4-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyridin-3-

amine

298
N-cyclohexyl-7-ethyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazol[1,2-a]pyridin-

3-amine

299
7-ethyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)-N-(2,4,4-trimethylpentan-2-yl)-

imidazo[1,2-a]pyridin-3-amine

300
N-cyclohexyl-7-ethyl-2-(3-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyridin-3-

amine

301
N-cyclopentyl-7-ethyl-2-(4-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyridin-3-

amine

302
N-cyclopentyl-7-ethyl-2-(6-(phenylethynyl)pyridin-3-yl)imidazo[1,2-a]pyridin-3-

amine

303
N-tert-butyl-7-ethyl-2-(6-(phenylethynyl)pyridin-3-yl)imidazo[1,2-a]pyridin-3-amine

304
N-tert-butyl-7-ethyl-2-(5-(pyridin-2-ylethynyl)furan-2-yl)imidazo[1,2-a]pyridin-3-

amine

305
7-isopropyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)-N-(2,4,4-trimethylpentan-2-

yl)imidazo[1,2-a]pyridin-3-amine

306
N-tert-butyl-7-isopropyl-2-(3-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyridin-3-

amine

307
N-tert-butyl-7-isopropyl-2-(4-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyridin-3-

amine

308
N-cyclohexyl-7-isopropyl-2-(5-(pyridin-2-ylethynyl)furan-2-yl)imidazo[1,2-a]pyridin-

3-amine

309
N-tert-butyl-7-isopropyl-2-(3-((6-methylpyridin-2-yl)ethynyl)phenyl)imidazo[1,2-a]-

pyridin-3-amine

310
6-chloro-N-cyclopentyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]-

pyridin-3-amine

311
N-tert-butyl-6-chloro-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-

3-amine

312
6-chloro-N-cyclohexyl-2-(3-(pyridin-2-ylethynyl)pheny)imidazo[1,2-a]pyridin-3-

amine

313
6-chloro-2-(3-(pyridin-2-ylethynyl)phenyl)-N-(2,4,4-trimethypentan-2-yl)-

imidazo[1,2-a]pyridin-3-amine

314
N-tert-butyl-6-chloro-2-(4-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]-pyridin-3-

amine

315
6-chloro-N-cyclohexyl-2-(4-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyridin-3-

amine

316
N-tert-butyl-6-chloro-2-(5-(pyridin-2-ylethynyl)furan-2-yl)imidazo[1,2-a]pyridin-3-

amine

317
6-chloro-N-cyclohexyl-2-(5-(pyridin-2-ylethynyl)furan-2-yl)imidazo[1,2-a]pyridin-3-

amine

318
6-chloro-2-(5-(pyrodin-2-ylethynyl)furan-2-yl)-N-(2,4,4-trimethylpentan-2-

yl)imidazo[1,2-a]pyridin-3-amine

319
6-chloro-N-cyclopentyl-2-(3-((6-methylpyridin-2-yl)ethynyl)phenyl)imidazo-

[1,2-a]pyridin-3-amine

320
N-tert-butyl-6-chloro-2-(3-((6-methylpyridin-2-yl)ethynyl)phenyl)imidazo-

[1,2-a]pyridin-3-amine

321
N-tert-butyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine

bis-hydrochloride

322
N-methyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine

323
N-tert-butyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine

bis-hydrochloride

324
[2-(5-pyridin-2-ylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(1,1,3,3-

tetramethyl-butyl)-amine

325
tert-butyl-[2-(5-pyrimidin-2-ylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-

amine hydrochloride

326
{2-[5-(3-amino-pyridin-2-ylethynyl)-thiophen-2-yl]-imidazo[1,2-a]pyridin-3-yl}-tert-

butyl-amine

327
tert-butyl-[2-(5-pyridin-2-ylethynyl-thiazol-2-yl)-imidazo[1,2-a]pyridin-3-yl]-amine

328
tert-butyl-[2-(2-pyridin-2-ylethynyl-thiazol-5-yl)-imidazo[1,2-a]pyridin-3-yl]-amine

329
tert-butyl-{2-[5-(6-fluoro-pyridin-2-ylethynyl)-thiophen-2-yl]-imidazo[1,2-a]pyridin-3-

yl}-amine hydrochloride

330
tert-butyl-{2-[5-(3-chloro-5-fluoro-phenylethynyl)-thiophen-2-yl]-

imidazo[1,2-a]pyridin-3-yl}-amine hydrochloride

331
tert-butyl-[2-(5-pyridin-2-ylethynyl-thiophen-2-yl)-imidazo[1,2-b]pyridazin-3-yl]-

amine hydrochloride

332
tert-butyl-[2-(5-thiazol-2-ylethynyl-thiophen-2-yl)-imidazo[1,2-b]pyridazin-3-yl]-amine

hydrochloride

333
tert-butyl-{2-[5-(3-trifluoromethoxy-phenylethynyl)-thiophen-2-yl]-

imidazo[1,2-a]pyrazin-3-yl}-amine

334
tert-butyl-{2-[5-(3-[1,3]dioxolan-2-yl-phenylethynyl)-thiophen-2-yl]-

imidazo[1,2-a]pyridin-3-yl}-amine

335
tert-butyl-{2-[5-(3,5-dimethyl-phenylethynyl)-thiophen-2-yl]-imidazo[1,2-a]pyridin-3-

yl}-amine hydrochloride

336
tert-butyl-{2-[5-(3-fluoro-pyridin-2-ylethynyl)-thiophen-2-yl]-imidazo[1,2-a]pyridin-3-

yl}-amine hydrochloride

337
tert-butyl-{2-[5-(3-methyl-3H-imidazol-4-ylethynyl)-thiophen-2-yl]-

imidazo[1,2-a]pyridin-3-yl}-amine hydrochloride

338
tert-butyl-{2-[5-(5-chloro-thiophen-2-ylethynyl)-thiophen-2-yl]-

imidazo[1,2-a]pyridin-3-yl}-amine hydrochloride

339
tert-butyl-{2-[5-(5-methyl-pyridin-2-ylethynyl)-thiophen-2-yl]-imidazo[1,2-a]pyridin-3-

yl}-amine hydrochloride

340
1-{3-[5-(3-tert-butylamino-imidazo[1,2-a]pyridin-2-yl)-thiophen-2-ylethynyl]-phenyl}-

ethanone hydrochloride

341
{3-[5-(3-tert-butylamino-imidazo[1,2-a]pyridin-2-yl)-thiophen-2-ylethynyl]-phenyl}-

methanol hydrochloride

342
N-tert-butyl-2-(5-((3-methoxypyridin-2-yl)ethynyl)thiophen-2-

yl)imidazo[1,2-a]pyridin-3-amine

343
N-tert-butyl-2-(5-(thiophen-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine

hydrochloride

344
5-((5-(3-(tert-butylamino)imidazo[1,2-a]pyridin-2-yl)thiophen-2-yl)ethynyl)-2-

fluorobenzonitrile hydrochloride

345
N-tert-butyl-2-(5-((3,4-difluorophenyl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-

amine

346
N-tert-butyl-2-(5-((3-(methoxymethyl)phenyl)ethynyl)thiophen-2-yl)imidazo-

[1,2-a]pyridin-3-amine

347
2-(5-((3-aminophenyl)ethynyl)thiophen-2-yl)-N-tert-butylimidazo[1,2-a]pyridin-3-

amine hydrochloride

348
N-tert-butyl-2-(5-((4-fluoro-3-methylphenyl)ethynyl)thiophen-2-yl)imidazo-

[1,2-a]pyridin-3-amine hydrochloride

349
N-tert-butyl-2-(5-((3,5-difluorophenyl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-

amine

350
N-tert-butyl-2-(5-(thiophen-3-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine

hydrochloride

351
N-tert-butyl-2-(5-((3-methylpyridin-2-yl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-

3-amine hydrochloride

352
3-((5-(3-(tert-butylamino)imidazo[1,2-a]pyridin-2-yl)thiophen-2-yl)ethynyl)-

benzenesulfonamide hydrochloride

353
3-((5-(3-(tert-butylamino)imidazo[1,2-a]pyridin-2-yl)thiophen-2-yl)ethynyl)benzoic

acid

354
3-((5-(3-(tert-butylamino)imidazo[1,2-a]pyridin-2-yl)thiophen-2-yl)ethynyl)-

benzamide hydrochloride

355
N-(3-((5-(3-(tert-butylamino)imidazo[1,2-a]pyridin-2-yl)thiophen-2-yl)ethynyl)-

phenyl)acetamide

356
N-tert-butyl-N-methyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-

3-amine

357
N,N-dimethyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine

358
N-tert-butyl-N-methyl-2-(5-(pyridin-2-ylethynyl)thiazol-2-yl)imidazo[1,2-a]pyridin-3-

amine

359
(6-((5-(3-(tert-butylamino)imidazo[1,2-a]pyridin-2-yl)thiophen-2-yl)ethynyl)pyridin-2-

yl)methanol

360
N-(3-((5-(3-(tert-butylamino)imidazo[1,2-a]pyridin-2-yl)thiophen-2-yl)ethynyl)-

phenyl)methanesulfonamide

361
N-tert-butyl-8-methyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-

3-amine hydrochloride

362
2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine

363
N-tert-butyl-2-(5-((3-chlorophenyl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-

amine

364
N-tert-butyl-2-(5-((2,3-difluorophenyl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-

amine

365
N-tert-butyl-7-chloro-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-

amine

Pharmacological Data:

1. The affinity of the substituted imidazo-3-yl-amine compounds of the general formula I according to the invention for the mGluR5 receptor was determined as described above.

The substituted imidazo-3-yl-amine compounds according to the invention exhibit an excellent affinity for the mGluR5 receptor.

Table 1 below shows the pharmacological data for the substituted imidazo-3-yl-amine compounds according to the Examples 1 to 332:

TABLE 1

mGluR5 receptor

inhibition of ³[H]-MPEP binding

Compound
[10 μM] in %

according to
at a concentration of the example

Example
compounds of 10 μM
IC₅₀

1
52

2
95

3
95

4
91

5
100

6
92

7
89

8
100

9
98

10
95

11
82

12
96

13
96

14
100

15
98

16
93

17
96

18

0.0640

19
78

20
79

21
91

22
84

23
86

24
94

25
81

26
97

27
82

28
98

29
87

30
73

31

0.5300

32
98

33
98

34
98

35
95

36
100

37
85

38
87

39
72

40
87

41
73

42
93

43
83

44
75

45
93

46
76

47
79

48
82

49
85

50
90

51
89

52
75

53
80

54
69

55
77

56
100

57
94

59

2.0700

60

1.2000

61

0.0425

62
26

63
65

64

0.0330

65

3.8400

66

3.1750

67

3.8400

68

2.3200

69

2.9300

70

1.0600

71

1.2700

72

5.3400

73

2.2100

74

1.1000

75

1.2900

76

0.0037

77

0.0057

79
35

82

0.2000

83
35

84

1.3200

85

2.0100

86

0.3200

87
35

88

1.4000

89

0.0450

91

0.0054

92
82

93

0.2500

94

0.0033

95

1.7400

96
79

97

0.5900

98

0.2500

99

0.5400

100

0.3400

101

2.4700

102

8.8500

103
66

104

0.0920

105

0.1500

106

0.2100

107

0.0520

108

1.2400

109

0.3000

110

0.0490

111

1.3700

112

7.5200

113

0.0750

114

2.1100

115

7.7400

116

0.0760

117

0.8800

118

6.3800

119

0.0360

120

3.6300

121

2.5400

122

0.1300

123

0.0140

124

0.1700

125

6.5200

126

3.2500

127

0.0084

128

15.5500

129

0.0120

130

0.0370

131

0.1400

132

0.0160

133

0.0150

134

0.5700

135

1.2000

136

13.7700

137

0.8600

138

15.1100

139

0.0710

140

0.0260

141

0.0028

143

0.0032

144

3.6800

146

0.0350

148

0.3300

150

0.1100

152

0.0230

153

2.9900

154

0.5900

156

0.0270

157

1.5500

158

0.0330

159

0.0100

160

0.0940

161

7.7400

162

4.2400

164

0.0540

165

0.0180

166

11.3300

167

0.0120

168

0.6400

169

0.0110

171

0.3600

172

0.0360

173

0.8000

174

0.8400

175

0.0510

176

0.0190

177

0.0160

178

0.0240

179

0.0260

180

0.5800

181

0.0180

182

8.8500

183

0.2300

184

0.2700

185

0.1900

192

0.0053

193
79

194
30

195
53

196
68

197
31

198
67

199
57

200
62

201
55

202
70

203
60

204
30

205
92

206
63

207
35

208
57

209
55

210
68

211
82

212
90

213
84

214
77

215
51

216
49

217
62

218
38

219
33

220
31

221
40

222
33

223
80

224
69

225
43

226
41

227
61

228
43

229
30

230
60

231
62

232
75

233
75

234
64

235
32

236
66

237
36

238
92

239
60

240
95

241
65

242
91

243
80

244
54

245
92

246
74

247
83

248
68

249
80

250
69

251
80

252
86

253
73

254
77

255
81

256
43

257
77

258
86

259
82

260
64

261
79

262
72

263
85

264
83

265
68

266
63

267
85

268
75

269
94

270
93

271
31

272
72

273
84

274
85

275
85

276
93

277
95

278
93

279
67

280
31

281
83

282
72

283
82

284
68

285
88

286
72

287
30

288
89

289
51

290
88

291
92

292
88

293
70

294
79

295
84

296
85

297
80

298
95

299
86

300
50

301
78

302
55

303
67

304
94

305
75

306
76

307
88

308
70

309
82

310
86

311
86

312
64

313
33

314
79

315
75

316
55

317
58

318
43

319
81

320
77

321

0.0093

322

0.1200

323

0.1100

324

0.0590

325

0.0130

326

0.0390

332

0.0140

333

0.4200

334

10.0400

335

336

0.0061

337

6.2600

338
52

339

0.3200

340

0.6200

341

0.2400

342

1.3600

343

0.0930

344

0.1700

345

346

0.6700

347

0.9200

348
44

349
39

350

0.5700

351

0.2300

2. The investigated compound according to the invention of Example 192 exhibited a pronounced, long-lasting antiallodynic action. The results are summarised in Table 2 below.

TABLE 2

Testing of inhibition against neuropathic pain in rats, [% MPE,

maximum possible effect] inhibition at the individual measuring points and over

the entire measurement time (AUC, area under the curve)

% MPE at time after

administration of the

compounds

AUC

Dose (mg/kg) p.o.
15 min
30 min
45 min
60 min
(0-60 min)
t-test

0
Mean
0.4
3.3
2.4
3.4
n.a.

Standard error of
1.5
1.0
0.7
0.8
n.a.

the mean

0.215
Mean
27.1
19.9
9.3
5.4
15.0
**

Standard error of
5.4
4.6
3.1
2.2
3.5

the mean

0.464
Mean
30.2
27.7
20.3
12.4
22.3
***

Standard error of
4.8
4.2
4.2
4.5
3.0

the mean

1
Mean
48.7
50.9
39.4
31.2
42.9
***

Standard error of
5.9
3.6
5.8
5.7
4.2

the mean

2.15
Mean
42.9
54.7
34.3
13.7
38.2
***

Standard error of
7.8
7.0
6.3
4.7
3.9

the mean

4.64
Mean
46.2
72.1
39.9
23.9
47.4
***

Standard error of
6.5
5.8
7.5
8.0
5.3

the mean

n.a. not applicable

3. The compound according to the invention of Example 192 was tested 60 min after p.o. administration and produced a dose-dependent anxiolytic effect characterised by a significant increase of the time in the open arms. The lowest active dose was 2.15 mg/kg, and an ED50 value of 2.75 (95% confidence interval 0.65-5.58) mg/kg was determined.

4. The substituted imidazo-3-yl-amine compounds according to the invention likewise exhibit an excellent action in the formaldehyde test in mice or in rats as shown in Table 3 below.

TABLE 3

ED₅₀value [mg/kg] or % inhibition

Rat
Mouse

Example
i.v.
p.o.
i.p.
p.o.
i.p.

91
—
7.3
4.7
2.3
1.2

110
—
61% at 21.5
—
—
—

mg/kg

116
—
—
—
—
15.2

127
—
5.9
2.2
—
7.7

192
0.8
7.6
41% at 4.64
—
—

mg/kg

The foregoing description and examples have been set forth merely to illustrate the invention and are not intended to be limiting. Since modifications of the described embodiments incorporating the spirit and substance of the invention may occur to persons skilled in the art, the invention should be construed broadly to include all variations within the scope of the appended claims and equivalents thereof.

Claims

1. A bicyclic imidazo-3-yl-amine compound corresponding to formula I,
2. The compound of claim 1, wherein said compound exists in an enantiomeric or diastereoisomeric form and is present in the form of a pure enantiomer or pure diastereoisomer.
3. The compound of claim 1, wherein said compound exists in the form of a mixture of stereoisomers and is present in the form of a mixture of stereoisomers.
4. The compound of claim 3, wherein said compound is present in the form of a racemic mixture.
5. A compound according to claim 1, wherein A1 represents a nitrogen atom or a C—R1a group,A2 represents a nitrogen atom or a C—R1b group,A3 represents a nitrogen atom or a C—R1c group,A4 represents a nitrogen atom or a C—R1d group,R1a, R1b, R1c, R1d, mutually independently, in each case represent hydrogen; a halogen; —NO2; —CN; —NH2; —NHR4; —NR5R6; —NH—C(═O)—R7; —C(═O)—R8, —C(═O)—NH2; —C(═O)—NHR9; —C(═O)—NR10R11; —C(═O)—OR12; —(CH2)m—C(═O)—OR13 with m=1, 2, 3, 4 or 5; —O—C(═O)—R14; —(CH2)N—O—C(═O)—R15 with N=1, 2, 3, 4 or 5; —OR16; —(CH2)o—O—R17 with o=1, 2, 3; 4 or 5; —SR18; —(CH2)p—S(═O)t—R19 with p=1, 2, 3, 4 or 5 and t=0, 1 or 2; —NH—S(═O)2—R26R27; —S(═O)2—NR28R29, —SF5; a linear or branched, saturated or unsaturated, unsubstituted or at least monosubstituted aliphatic C1-10 group; a saturated or unsaturated, unsubstituted or at least monosubstituted cycloaliphatic C3-8 group optionally comprising at least one heteroatom as a ring member, which cycloaliphatic C3-8 group may be attached via a linear or branched C1-5 alkylene group; or represent an unsubstituted or at least monosubstituted 5- to 14-membered aryl or heteroaryl group which may be attached via a linear or branched C1-5 alkylene group,or R1a and R1b form an unsubstituted or at least monosubstituted anellated phenyl group with the C—C bridge joining them together,or R1b and R1c form an unsubstituted or at least monosubstituted anellated phenyl group with the C—C bridge joining them together,or R1c and R1d form an unsubstituted or at least monosubstituted anellated phenyl group with the C—C bridge joining them together,R2 and R3, mutually independently, in each case represent hydrogen; —C(═O)—R20; —(CH2)q—C(═O)—R21 with q=1, 2, 3, 4 or 5; —C(═O)—O—R22; —(CH2)r—C(═O)—O—R23 with r=1, 2, 3, 4 or 5; —C(═O)—NHR24; —(CH2)s—C(═O)—NHR25 with s=1, 2, 3, 4 or 5; a linear or branched, saturated or unsaturated, unsubstituted or at least monosubstituted aliphatic C1-16 group; a saturated or unsaturated, unsubstituted or at least monosubstituted cycloaliphatic C4-8 group, optionally comprising at least one heteroatom as a ring member, which cycloaliphatic C4-8 group may be attached via a linear or branched C1-5 alkylene group; or represent an unsubstituted or at least monosubstituted 5- to 14-membered aryl or heteroaryl group, which may be attached via a linear or branched C1-5 alkylene group,or R2 and R3, together with the nitrogen atom joining them together as a ring member, form a saturated or unsaturated heterocycloaliphatic C4-10 group optionally comprising at least one further heteroatom as a ring member, which heterocycloaliphatic C4-10 group is optionally fused with an unsubstituted or at least monosubstituted mono- or polycyclic ring system, wherein the rings of the ring system are in each case 5-, 6- or 7-membered;R4, R5, R6, R7, R9, R10, R11, R14 and R15, in each case mutually independently, represent a linear or branched, saturated or unsaturated aliphatic C1-4 group or represent an unsubstituted or at least monosubstituted 5- to 14-membered aryl or heteroaryl group, which may be attached via a linear or branched C1-5 alkylene group,R8, R12, R13, R16, R17, R18, R19, R20, R21, R22, R23, R24, R25, R26, R27, R28 and R29, in each case mutually independently, represent a hydrogen group; a linear or branched, saturated or unsaturated aliphatic C1-4 group or an unsubstituted or at least monosubstituted 5- to 14-membered aryl or heteroaryl group, which may be attached via a linear or branched C1-5 alkylene group,M1 represents a 5- or 6-membered aryl or heteroaryl group, which may be substituted with at least one further substituent and is optionally fused with an unsubstituted or at least monosubstituted mono- or bicyclic ring system, wherein the rings of the ring system are in each case 5-, 6- or 7-membered, andM2 represents a 5- or 6-membered aryl or heteroaryl group, which may be unsubstituted or at least monosubstituted and may be fused with an unsubstituted or at least monosubstituted mono- or bicyclic ring system, wherein the rings of the ring system are in each case 5-, 6- or 7-membered;
6. A compound according to claim 1, wherein A1 represents a C—R1a group,A2 represents a C—R1b group,A3 represents a C—R1c group andA4 represents a C—R1d group,
7. A compound according to claim 6, wherein A1 represents a C—R1a group,A2 represents a C—R1b group,A3 represents a C—R1c group andA4 represents a C—R1d group,
8. A compound according to claim 1, wherein R1a, R1b, R1c, R1d, mutually independently, in each case represent —H; —F; —Cl, —Br; —I; —NO2; —CN; —CF3; —SF5; —NH2; —S(═O)—NH2, —NHR4; —NR5R6; —C(═O)—OR12; —(CH2)m—C(═O)—OR13 with m=1, 2 or 3; —O—C(═O)—R14; —OR16; —(CH2)o—O—R17 with o=1, 2 or 3; a linear or branched C1-10 alkyl group; or represent an unsubstituted or at least monosubstituted 5- or 6-membered aryl or heteroaryl group, which may be attached via a linear or branched C1-4 alkylene group.
9. A compound according to claim 1, wherein R1a, R1b, R1c, R1d, mutually independently, in each case represent —H; —F; —Cl, —Br; —I; —NO2; —CN; —CF3; —SF5; —NH2; —S(═O)—NH2, —NHR4; —NR5R6; —C(═O)—OR12; —(CH2)m—C(═O)—OR13 with m=1, 2 or 3; —O—C(═O)—R14; —OR16; —(CH2)o—R17 with o=1, 2 or 3; a linear or branched alkyl group selected from the group consisting of methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl and tert-butyl, or represent an aryl or heteroaryl group selected from the group consisting of phenyl, furanyl, thiophenyl and pyridinyl, which is in each case unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, —CN, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, —OH, —O—CH3, —O—C2H5 and is optionally attached via a —(CH2)—, —(CH2)2— or —(CH2)3 group.
10. A compound according to claim 1, wherein R1a, R1b, R1c, R1d, mutually independently, in each case represent —H; —F; —Cl, —Br; —CF3; —CN; —SF5; —S(═O)—NH2, —C(═O)—OR12; —(CH2)m—C(═O)—OR13 with m=1 or 2; —O—C(═O)—R14; —OR16; —(CH2)o—O—R17 with o=1 or 2; a linear or branched alkyl group selected from the group consisting of methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl and tert-butyl, or represent a phenyl group, which is unsubstituted or substituted with 1, 2 or 3 substituents mutually independently selected from the group consisting of F, Cl, Br, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, —O—CH3, —O—C2H5 and is optionally attached via a —(CH2)—, —(CH2)2— or —(CH2)3 group.
11. A compound according to claim 1, wherein R1a, R1b, R1c, R1d, mutually independently, in each case represent —H; —F; —Cl, —Br; —CF3; —CN; —SF5; —S(═O)—NH2, —C(═O)—OR12; —(CH2)m—C(═O)—OR13 with m=1; —O—C(═O)—R14; —OR16; —(CH2)0—O—R17 with o=1; a linear or branched alkyl group selected from the group consisting of methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl and tert-butyl; or represent an unsubstituted phenyl group, which is optionally attached via a —(CH2)—, —(CH2)2— or —(CH2)3 group.
12. A compound according to claim 1, wherein R1a and R1b or R1b and R1c or R1c and R1d, together with the C—C bridge joining them together, form an anellated phenyl group which may be substituted with 1, 2, 3 or 4 substituents mutually independently selected from the group consisting of F, Cl, Br, —CN, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, —OH, —O—CH3, —O—C2H5.
13. A compound according to claim 1, wherein R2 and R3, mutually independently, in each case represent a hydrogen; —C(═O)—R20; —(CH2)q—C(═O)—R21 with q=1, 2, 3, 4 or 5; —(CH2)r—C(═O)—O—R23 with r=1, 2, 3, 4 or 5; —C(═O)—NHR24; a linear or branched C1-16 alkyl group; an unsubstituted or at least monosubstituted C4-8 cycloalkyl group, which may be attached via a linear or branched C1-3 alkylene group; or represent an unsubstituted or at least monosubstituted, 5- or 6-membered aryl or heteroaryl group, which may be attached via a linear or branched C1-3 alkylene.
14. A compound according to claim 1, wherein R2 and R3, mutually independently, in each case represent a hydrogen; —C(═O)—R20; —(CH2)q—C(═O)—R21 with q=1, 2 or 3; —(CH2)r—C(═O)—O—R23 with r=1, 2 or 3; a linear or branched C1-10 alkyl group; a C4-8 cycloalkyl group, which is in each case unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, —CN, —CF3, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, —OH, —O—CH3 and —O—C2H5 and is optionally attached via a linear or branched C1-3 alkylene group; or represent an aryl or heteroaryl group selected from the group consisting of phenyl, thiophenyl, furanyl and pyridinyl, which is in each case unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, —CN, —CF3, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, —OH, —O—CH3 and —O—C2H5 and is optionally attached via a linear or branched C1-3 alkylene group.
15. A compound according to claim 1, wherein R2 and R3, mutually independently, in each case represent a hydrogen; —C(═O)—R20; —(CH2)q—C(═O)—R21 with q=1 or 2; —(CH2)r—C(═O)—O—R23 with r=1 or 2; an alkyl group selected from the group consisting of methyl; ethyl; propyl; iso-propyl; n-butyl; tert-butyl; sec-butyl; iso-butyl; n-pentyl; n-hexyl; n-heptyl; n-octyl; (1,1,3,3)-tetramethyl-butyl; (1,1)-dimethyl-pentyl and (1,1)-dimethyl-butyl; an unsubstituted cyclopentyl or cyclohexyl group, which may in each case be attached via a —(CH2)—, —(CH2)2— or —(CH2)3 group; or represent a phenyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 2-furanyl, 3-furanyl, 2-thiophenyl or 3-thiophenyl group, which is in each case unsubstituted or optionally substituted with 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, —CN, —CF3, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, —O—CH3 and —O—C2H5 and is optionally attached via a —(CH2)—, —(CH2)2—, —C(H)(CH3)— or —(CH2)3 group.
16. A compound according to claim 1, wherein R2 and R3, together with the nitrogen atom joining them together as a ring member, form a group selected from the group consisting of imidazolidinyl, piperidinyl, piperazinyl, morpholinyl, pyrrolidinyl, thiomorpholinyl, azepanyl, diazepanyl and azocanyl, which may in each case be unsubstituted or optionally substituted with 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —CN, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, —OH, oxo, thioxo, —O—CH3, —O—C2H5, —O—C3H7, —NH2, —N(CH3)2, —N(C2H5)2, —NH—CH3, —NH—C2H5, —O—CF3, —S—CF3, —S(═O)—CH3, —S(═O)—C2H5, —S(═O)2—CH3, —S(═O)2—C2H5, —C(═O)—OH, —C(═O)—H, —C(═O)—CH3, —C(═O)—C2H5, —C(═O)—N(CH3)2, —C(═O)—NH—CH3, —C(═O)—NH2, —C(═O)—O—CH3, —C(═O)—O—C2H5 and —C(═O)—O—C(CH3)3.
17. A compound according to claim 1, wherein R2 and R3, together with the nitrogen atom joining them together as a ring member, form a group selected from the group consisting of imidazolidinyl, piperidinyl, piperazinyl, morpholinyl, pyrrolidinyl, thiomorpholinyl, azepanyl, diazepanyl and azocanyl.
18. A compound according to claim 1, wherein R4, R5, R6, R7, R9, R10, R11, R14 and R15, in each case mutually independently represent a linear or branched C1-4 alkyl group or an unsubstituted or at least monosubstituted 5- to 14-membered aryl or heteroaryl group, which may be attached via a linear or branched C1-5 alkylene group.
19. A compound according to claim 1, wherein R4, R5, R6, R7, R9, R10, R11, R14 and R15, in each case mutually independently, represent an alkyl group selected from the group consisting of methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl and tert-butyl, or represent an unsubstituted or at least monosubstituted 5- or 6-membered aryl or heteroaryl group, which may be attached via a linear or branched C1-3 alkylene group.
20. A compound according to claim 1, wherein R4, R5, R6, R7, R9, R10, R11, R14 and R15, in each case mutually independently, represent an alkyl group selected from the group consisting of methyl, ethyl, n-propyl and iso-propyl, or represent a phenyl group, which is in each case unsubstituted or substituted with 1, 2 or 3 substituents mutually independently selected from the group consisting of F, Cl, Br, —CN, —CF3, —SF5, methyl, ethyl, n-propyl, iso-propyl, tert-butyl, —O—CH3 and —O—C2H5 and is optionally attached via a —(CH2), —(CH2)2 or —(CH2)3 group.
21. A compound according to claim 1, wherein R8, R12, R13, R16, R17, R18, R19, R20 R21, R22 R23, R24, R25, R26, R27, R28 and R29, in each case mutually independently represent a hydrogen; a linear or branched C1-8 alkyl group, or represent an unsubstituted or at least monosubstituted 5- to 14-membered aryl or heteroaryl group, which may be attached via a linear or branched C1-5 alkylene group.
22. A compound according to claim 1, wherein R8, R12, R13, R16, R17, R18, R19, R20, R21, R22, R23, R24, R25, R26, R27, R28 and R29, in each case mutually independently, represent a hydrogen; a linear or branched, saturated or unsaturated aliphatic C1-4 group or an unsubstituted or at least monosubstituted 5- to 6-membered aryl or heteroaryl group, which may be attached via a linear or branched C1-3 alkylene group.
23. A compound according to claim 1, wherein R8, R12, R13, R16, R17, R18, R19, R20, R21, R22, R23, R24, R25, R26, R27, R28 and R29, in each case mutually independently, represent a hydrogen; an alkyl group selected from the group consisting of methyl, ethyl, n-propyl and iso-propyl and tert-butyl, or represent a phenyl group, which is in each case unsubstituted or substituted with 1, 2 or 3 substituents mutually independently selected from the group consisting of F, Cl, Br, —CN, —CF3, —SF5, methyl, ethyl, n-propyl, iso-propyl, tert-butyl, —O—CH3 and —O—C2H5 and is optionally attached via a —(CH2), —(CH2)2 or —(CH2)3 group.
24. A compound according to claim 1, wherein M1 represents a 5- or 6-membered aryl or heteroaryl group, which may optionally be substituted with at least one further substituent, wherein the heteroaryl group optionally comprises 1, 2, 3, 4 or 5 heteroatom(s) as ring member(s), which are mutually independently selected from the group consisting of nitrogen, oxygen and sulfur.
25. A compound according to claim 1, wherein M1 represents an aryl or heteroaryl group selected from the group consisting of phenyl, furanyl, thiophenyl, pyrazolyl, pyrazinyl, pyridazinyl, pyrimidinyl, pyridinyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, thiadiazolyl, imidazolyl, oxadiazolyl, triazolyl, diazinyl, triazinyl, tetrazinyl and tetrazolyl, which may optionally be substituted with at least one further substituent.
26. A compound according to claim 1, wherein M1 is selected from the group consisting of groups 1 to 38,
27. A compound according to claim 1, wherein M1 is selected from the group consisting of groups 1 to 9, 11, 21, 22 and 36 to 38,
28. A compound according to claim 1, wherein M1 is selected from the group consisting of groups 1 to 9, 11, 21, 22 and 36 to 38,
29. A compound according to claim 1, wherein M2 represents an unsubstituted or at least monosubstituted, 5- or 6-membered aryl or heteroaryl group, wherein the heteroaryl group comprises 1, 2, 3, 4 or 5 heteroatom(s) as ring member(s), which are mutually independently selected from the group consisting of nitrogen, oxygen and sulfur, and wherein the aryl or heteroaryl group may be fused with an unsubstituted or at least monosubstituted mono- or bicyclic ring system, wherein the rings of the ring system are in each case 5- or 6-membered and may in each case comprise 1, 2, 3 or 4 heteroatom(s) as ring member(s), which are mutually independently selected from the group consisting of nitrogen, oxygen and sulphur.
30. A compound according to claim 1, wherein M2 represents a group selected from the group consisting of phenyl, furanyl, thiophenyl, pyrazolyl, pyrazinyl, pyridazinyl, pyrimidinyl, pyridinyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, thiadiazolyl, oxadiazolyl, triazolyl, diazinyl, triazinyl, tetrazinyl, tetrazolyl, pentazolyl, imidazolyl, quinolinyl, isoquinolinyl, naphthyl, indolyl, isoindolyl, benzofuranyl, isobenzofuranyl, benzothiophenyl and isobenzothiophenyl, wherein the group may in each case be unsubstituted or at least monosubstituted.
31. A compound according to claim 1, wherein M2 represents a group selected from the group consisting of phenyl, furanyl, thiophenyl, pyrazolyl, pyrazinyl, pyridazinyl, pyrimidinyl, pyridinyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, thiadiazolyl, oxadiazolyl, triazolyl, diazinyl, triazinyl, tetrazinyl, tetrazolyl, pentazolyl, imidazolyl, quinolinyl, isoquinolinyl, naphthyl, indolyl, isoindolyl, benzofuranyl, isobenzofuranyl, benzothiophenyl and isobenzothiophenyl, wherein the particular group may be unsubstituted or optionally substituted with 1, 2, 3, 4 or 5 substituents, which are in each case mutually independently selected from the group consisting of F, Cl, Br, —CN, —CF3, —SF5, —S—CH3, —S—C2H5, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, ethenyl, propenyl, —OH, —O—CH3, —O—C2H5, —O—C3H7, —NH2, —N(CH3)2, —NH—CH3, —CH2—NH2, —N(C2H5)2, —NO2, —O—CF3, —C(═O)—H, —S—CF3, —SH, —C(═O)—O—CH3, —C(═O)—O—C2H5, phenyl, pyrrolyl, (1,3)-dioxolanyl, —Si(phenyl)2[C(CH3)3], —C(═O)—CH3, —C(═O)—C2H5, —NH—S(═O)2—CH3, —NH—S(═O)2—C2H5, —S(═O)2—NH2, —S(═O)2—NH—CH3, —CH2—OH, —C(═O)—OH, —CH2—O—CH3, —C(═O)—NH2, —C(═O)—NH—CH3, —NH—C(═O)—CH3; —NH—C(═NH)—NH2, —NH—S(═O)2—OH and —S(═O)2—N(CH3)2.
32. A compound according to claim 1, wherein M2 represents a group selected from the group consisting of groups 1 to 36,
33. A compound according to claim 1, wherein M2 is unsubstituted or substituted with 1, 2 or 3 substituents, which are mutually independently selected from the group consisting of F, Cl, Br, —CN, —CF3, —SF5, —S—CH3, —S—C2H5, methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl, ethenyl, propenyl, —O—CH3, —O—C2H5, —NH2, —N(CH3)2, —NH—CH3, —CH2—NH2, —O—CF3, —C(═O)—H, —C(═O)—O—CH3, —C(═O)—O—C2H5, phenyl, pyrrolyl, (1,3)-dioxolanyl, —Si(phenyl)2[C(CH3)3], —NO2, NH—S(═O)2—CH3, —NH—S(═O)2—C2H5, —S(═O)2-NH2, —S(═O)2—NH—CH3, —CH2—OH, —C(═O)—CH3, —C(═O)—OH, —CH2—O—CH3, —C(═O)—NH2, —C(═O)—NH—CH3, —NH—C(═O)—CH3, —S(═O)2—N(CH3)2, —NH—S(═O)2—OH and —NH—C(═NH)—NH2.
34. A compound according to claim 1, wherein A1 represents a C—R1a group,A2 represents a C—R1b group,A3 represents a C—R1c group andA4 represents a C—R1d group;
35. A compound according to claim 1, wherein A1 represents a C—R1a group,A2 represents a C—R1b group,A3 represents a C—R1c group andA4 represents a C—R1d group,
36. A compound according to claim 35, said compound corresponding to formula Id
37. A compound according to claim 35, said compound corresponding to formula Ie
38. A compound according to claim 35, said compound corresponding to formula If
39. A compound according to claim 35, said compound corresponding to formula Ig
40. A compound according to claim 35, said compound corresponding to formula Ih
41. A compound according to claim 35, said compound corresponding to formula Ik
42. A compound according to claim 35, said compound corresponding to formula Im
43. A compound according to claim 35, said compound corresponding to formula In
44. A compound according to claim 1, wherein said compound is selected from the group consisting of: [1] cyclopentyl-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine,[2] cyclohexylmethyl-[5-methyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-amine,[3] cyclohexylmethyl-[6-methyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-amine,[4] cyclohexylmethyl-[7-methyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-amine,[5] cyclohexylmethyl-[8-methyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-amine,[6] cyclohexylmethyl-[5,7-dimethyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-amine,[7] [8-benzyloxy-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-cyclohexylmethyl-amine,[8] cyclohexylmethyl-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine,[9] cyclohexylmethyl-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrimidin-3-yl]-amine,[10] (4-methoxy-benzyl)-[5-methyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-amine,[11] (4-methoxy-benzyl)-[6-methyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-amine,[12] (4-methoxy-benzyl)-[7-methyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-amine,[13] (4-methoxy-benzyl)-[8-methyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-amine,[14] [5,7-dimethyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(4-methoxy-benzyl)-amine,[15] [8-benzyloxy-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(4-methoxy-benzyl)-amine,[16] (4-methoxy-benzyl)-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-amine,[17] (4-methoxy-benzyl)-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine,[18] tert-butyl-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine,[19] tert-butyl-[6-methyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-amine,[20] [8-benzyloxy-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(3-methoxy-phenyl)-amine,[21] (3-methoxy-benzyl)-[5-methyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-amine,[22] (3-methoxy-benzyl)-[8-methyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-amine,[23] [5,7-dimethyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(3-methoxy-benzyl)-amine,[24] [8-benzyloxy-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(3-methoxy-benzyl)-amine,[25] (3-methoxy-benzyl)-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-amine,[26] (3-methoxy-benzyl)-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine,[27] [6-methyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(1-phenyl-ethyl)-amine,[28] [7-methyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(1-phenyl-ethyl)-amine,[29] [5,7-dimethyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(1-phenyl-ethyl)-amine,[30] [8-benzyloxy-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(1-phenyl-ethyl)-amine,[31] (1-phenyl-ethyl)-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine,[32] (2-chloro-benzyl)-[5,7-dimethyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-amine,[33] (3-chloro-4-fluoro-phenyl)-[7-phenyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-amine,[34] (4-methoxy-benzyl)-[7-methyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrimidin-3-yl]- amine,[35] [8-methyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(1-phenyl-ethyl)-amine,[36] [7-methyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrimidin-3-yl]-(1-phenyl-ethyl)-amine,[37] (2-methoxy-benzyl)-[7-methyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-amine,[38] (2-methoxy-benzyl)-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]- amine,[39] (2-chloro-benzyl)-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-amine,[40] (2-methoxy-benzyl)-[7-methyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrimidin-3-yl]-amine,[41] (3-methoxy-phenyl)-[6-methyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-amine,[42] [5,7-dimethyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(3-methoxy-phenyl)-amine,[43] (3-methoxy-phenyl)-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine,[44] [7-ethyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(2-methoxy-benzyl)-amine,[45] (2-chloro-benzyl)-[7-ethyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-amine,[46] [7-tert-butyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(3-chloro-4-fluoro-phenyl)-amine,[47] (3-methoxy-benzyl)-[7-methyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrimidin-3-yl]-amine,[48] [7-ethyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(2-fluoro-phenyl)-amine,[49] [7-tert-butyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(2-fluoro-phenyl)-amine,[50] (2,4-difluoro-phenyl)-[2-(5-phenylethynyl-thiophen-2-yl)-7-(3-phenyl-propyl)-imidazo[1,2-a]pyridin-3-yl]-amine,[51] (4-fluoro-benzyl)-[7-methyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-amine,[52] [5,7-dimethyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(4-fluoro-benzyl)-amine,[53] [7-ethyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(3-trifluoromethyl-benzyl)-amine,[54] [7-isopropyl-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(3-trifluoromethyl-benzyl)-amine,[55] tert-butyl-[2-(4-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine,[56] [2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-(1,1,3,3-tetramethyl-butyl)-amine,[57] butyl-[2-(4-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine,[59] [2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(1,1,3,3-tetramethyl-butyl)-amine,[60] [2-(5-pyridinyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-(1,1,3,3-tetramethyl-butyl)-amine,[61] [2-(5-pyridin-4-ylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-(1,1,3,3-tetramethyl-butyl)-amine,[62] [6-chloro-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(1,1,3,3-tetramethyl-butyl)-amine,[63] [6,8-dichloro-2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(1,1,3,3-tetramethyl-butyl)-amine,[64] [2-(5-pyridin-2-ylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-(1,1,3,3-tetramethyl-butyl)-amine,[65] dimethyl-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine,[66] methyl-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine,[67] N-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-acetamide,[68] ethyl-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine,[69] propyl-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine,[70] butyl-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine,[71] (2-methylpropyl)-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine,[72] pentyl-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine,[73] {(methoxycarbonylmethyl)-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amino}-acetic acid methyl ester,[74] benzyl-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine,[75] [2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-ylamino]-acetic acid methyl ester,[76] tert-butyl-[2-(5-pyridin-4-ylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine,[77] tert-butyl-[2-(5-pyridin-2-ylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine,[78] N-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-benzamide,[79] [2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-bis-pyridin-3-ylmethyl-amine,[80] 2,2-dimethyl-N-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-propionamide,[81] 3-methoxy-N-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-benzamide,[82] tert-butyl-[2-(5-pyridin-3-ylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine[83] 2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-ylamine[84] methyl-2-(5-(phenylethynyl)thiophen-2-yl)-3-(2,4,4-trimethylpentan-2-ylamino)imidazo[1,2-a]pyrazine-8-carboxylate[85] 2-(5-(phenylethynyl)thiophen-2-yl)-N-(2,4,4-trimethylpentan-2-yl)imidazo[1,2-a]pyrimidin-3-amine[86] 2-(5-((6-methylpyridin-2-yl)ethynyl)thiophen-2-yl)-N-(2,4,4-trimethylpentan-2-yl)imidazo[1,2-a]pyrazin-3-amine[87] N--cyclohexyl-2-(5-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine[88] 2-(5-(phenylethynyl)thiophen-2-yl)-3-(piperidin-1-yl)imidazo[1,2-a]pyrazine[89] N-tert-butyl-N-methyl-2-(5-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine[90] methyl-2-(5-(phenylethynyl)thiophen-2-yl)-3-(2,4,4-trimethylpentan-2-ylamino)imidazo[1,2-a]pyridine-6-carboxylate[91] N-tert-butyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride[92] 8-bromo-N-cyclopentyl-6-methyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine[93] N,N-diethyl-2-(5-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine[94] N-tert-butyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine[95] N-tert-butyl-2-(5-(phenylethynyl)furan-2-yl)imidazo[1,2-a]pyrazin-3-amine[96] 8-bromo-N-tert-butyl-6-methyl-2-(3-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyridin-3-amine[97] N-tert-butyl-8-methyl-2-(5-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine[98] N-methyl-2-(5-(phenylethynyl)thiophen-2-yl)-N-(2,4,4-trimethylpentan-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride[99] 2-(5-(phenylethynyl)thiophen-2-yl)-3-(pyrrolidin-1-yl)imidazo[1,2-a]pyrazine hydrochloride[100] N-tert-butyl-2-(5-((4-fluorophenyl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride[101] N-tert-butyl-7-methyl-2-(5-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine[102] N-tert-butyl-5-methyl-2-(5-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine[103] 8-chloro-2-(3-(pyridin-2-ylethynyl)phenyl)-6-(trifluoromethyl)-N-(2,4,4-trimethylpentan-2-yl)imidazo[1,2-a]pyridin-3-amine[104] N-tert-butyl-2-(5-((3-fluorophenyl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride[105] N-tert-butyl-2-(5-((2-fluorophenyl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride[106] methyl-3-(tert-butylamino)-2-(5-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazine-8-carboxylate[107] N-tert-butyl-2-(5-(pyrazin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine[108] 2-(5-((4-aminophenyl)ethynyl)thiophen-2-yl)-N-tert-butylimidazo[1,2-a]pyrazin-3-amine[109] N-isopropyl-2-(5-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine[110] N-tert-butyl-2-(5-(thiophen-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride[111] N-tert-butyl-2-(3-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyrazin-3-amine[112] N-tert-butyl-2-(5-((2-methoxyphenyl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride[113] N-tert-butyl-2-(5-((3-methoxyphenyl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride[114] N-tert-butyl-2-(5-((4-methoxyphenyl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride[115] N-tert-butyl-2-(5-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]quinolin-1-amine[116] N-tert-butyl-2-(4-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyrazin-3-amine[117] N-tert-butyl-2-(3-((6-methylpyridin-2-yl)ethynyl)phenyl)imidazo[1,2-a]pyrazin-3-amine[118] N-tert-butyl-2-(2-methyl-6-(phenylethynyl)pyridin-3-yl)imidazo[1,2-a]pyrazin-3-amine[119] N-tert-butyl-2-(5-(pyridin-2-ylethynyl)furan-2-yl)imidazo[1,2-a]pyrazin-3-amine[120] 3-(tert-butylamino)-2-(5-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazine-8-carboxylic acid[121] 4-((5-(3-(tert-butylamino)imidazo[1,2-a]pyrazin-2-yl)thiophen-2-yl)ethynyl)phenol hydrochloride[122] 3-((5-(3-(tert-butylamino)imidazo[1,2-a]pyrazin-2-yl)thiophen-2-yl)ethynyl)phenol[123] 2-(5-((3-aminophenyl)ethynyl)thiophen-2-yl)-N-tert-butylimidazo[1,2-a]pyrazin-3-amine hydrochloride[124] 2-(5-((2-aminophenyl)ethynyl)thiophen-2-yl)-N-tert-butylimidazo[1,2-a]pyrazin-3-amine hydrochloride[125] N-tert-butyl-2-(5-(phenylethynyl)thiophen-2-yl)imidazo[2,1-a]isoquinolin-3-amine[126] N-tert-butyl-2-(6-(phenylethynyl)pyridin-3-yl)imidazo[1,2-a]pyrazin-3-amine[127] N-tert-butyl-2-(5-(pyridin-4-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride[128] 2-(5-((6-aminopyridin-3-yl)ethynyl)thiophen-2-yl)-N-tert-butylimidazo[1,2-a]pyrazin-3-amine hydrochloride[129] N-tert-butyl-2-(5-(pyrimidin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride[130] N-tert-butyl-2-(5-((4-methylpyridin-2-yl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride[131] N-tert-butyl-2-(5-((5-methylpyridin-2-yl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride[132] N-tert-butyl-2-(5-(pyridin-4-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine hydrochloride[133] N-tert-butyl-2-(5-(thiazol-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine[134] 2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride[135] N-tert-butyl-2-(5-((5-methylthiophen-2-yl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride[136] 2-(5-((6-aminopyridin-2-yl)ethynyl)thiophen-2-yl)-N-tert-butylimidazo[1,2-a]pyrazin-3-amine hydrochloride[137] N-tert-butyl-2-(5-((3-methylthiophen-2-yl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine[138] N-tert-butyl-2-(4-(phenylethynyl)thiazol-2-yl)imidazo[1,2-a]pyrazin-3-amine[139] N-tert-butyl-2-(5-(m-tolylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine[140] 3-((5-(3-(tert-butylamino)imidazo[1,2-a]pyrazin-2-yl)thiophen-2-yl)ethynyl)benzonitrile hydrochloride[141] N-tert-butyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrimidin-3-amine[142] N-tert-butyl-2-(6-(phenylethynyl)pyridin-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride[143] N-tert-butyl-N-methyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine[144] 4-((5-(3-(tert-butylamino)imidazo[1,2-a]pyrazin-2-yl)thiophen-2-yl)ethynyl)benzonitrile hydrochloride[145] 2-(5-((1H-indol-6-yl)ethynyl)thiophen-2-yl)-N-tert-butylimidazo[1,2-a]pyrazin-3-amine hydrochloride[146] N-tert-butyl-2-(2-(phenylethynyl)thiazol-5-yl)imidazo[1,2-a]pyrazin-3-amine[147] N-tert-butyl-2-(5-(quinolin-6-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride[148] 2-(5-((3-(1H-pyrrol-1-yl)phenyl)ethynyl)thiophen-2-yl)-N-tert-butylimidazo[1,2-a]pyrazin-3-amine hydrochloride[149] 2-(5-((1H-indol-4-yl)ethynyl)thiophen-2-yl)-N-tert-butylimidazo[1,2-a]pyrazin-3-amine hydrochloride[150] N-tert-butyl-2-(5-((3-nitrophenyl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride[151] N-tert-butyl-2-(5-((4-nitrophenyl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride[152] N-tert-butyl-2-(5-(thiazol-4-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride[153] 2-((5-(3-(tert-butylamino)imidazo[1,2-a]pyrazin-2-yl)thiophen-2-yl)ethynyl)phenol[154] 2-(5-((3-(aminomethyl)phenyl)ethynyl)thiophen-2-yl)-N-tert-butylimidazo[1,2-a]pyrazin-3-amine[155] 2-(5-(biphenyl-3-ylethynyl)thiophen-2-yl)-N-tert-butylimidazo[1,2-a]pyrazin-3-amine hydrochloride[156] N-tert-butyl-2-(5-(thiophen-3-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride[157] N-tert-butyl-2-(5-((3-(dimethylamino)phenyl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride[158] N-tert-butyl-2-(5-((6-methylpyridin-2-yl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride[159] N-tert-butyl-2-(5-((3-fluoropyridin-2-yl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride[160] N-tert-butyl-2-(5-((3-(methylamino)phenyl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride[161] N-tert-butyl-2-(5-(p-tolylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine[162] N-tert-butyl-2-(5-(o-tolylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride[163] N-tert-butyl-2-(4-methyl-5-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride[164] N-tert-butyl-2-(4-methyl-5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride[165] N-tert-butyl-2-(5-((6-fluoropyridin-2-yl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine[166] N-tert-butyl-2-(5-((2-nitrophenyl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine[167] N-tert-butyl-8-chloro-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine[168] N-tert-butyl-2-(5-((6-methoxypyridin-2-yl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine[169] N-tert-butyl-2-(5-((5-fluoropyridin-2-yl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride[170] 2-(4-(3-(tert-butylamino)imidazo[1,2-a]pyrazin-2-yl)-2-(phenylethynyl)phenyl)acetonitrile[171] N-tert-butyl-2-(5-((5-methoxypyridin-3-yl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride[172] 5-((5-(3-(tert-butylamino)imidazo[1,2-a]pyrazin-2-yl)thiophen-2-yl)ethynyl)nicotinonitrile hydrochloride[173] N-tert-butyl-2-(5-((3-(methylthio)phenyl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine[174] methyl-3-((5-(3-(tert-butylamino)imidazo[1,2-a]pyrazin-2-yl)thiophen-2-yl)ethynyl)benzoate[175] N-tert-butyl-2-(5-((3,5-difluoropyridin-2-yl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine[176] N-tert-butyl-2-(5-(phenylethynyl)thiazol-2-yl)imidazo[1,2-a]pyrazin-3-amine[177] N-tert-butyl-2-(2-(pyridin-4-ylethynyl)thiazol-5-yl)imidazo[1,2-a]pyrazin-3-amine[178] 3-((5-(3-(tert-butylamino)imidazo[1,2-a]pyrazin-2-yl)thiophen-2-yl)ethynyl)benzaldehyde[179] 3-((5-(3-(tert-butylamino)imidazo[1,2-a]pyrazin-2-yl)thiophen-2-yl)ethynyl)-4-fluorobenzonitrile[180] N-tert-butyl-2-(5-((3-(trifluoromethyl)phenyl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride[181] N-tert-butyl-2-(2-(pyridin-2-ylethynyl)thiazol-5-yl)imidazo[1,2-a]pyrazin-3-amine[182] N-tert-butyl-2-(3-methyl-5-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride[183] N-tert-butyl-2-(3-methyl-5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride[184] N-tert-butyl-2-(5-((3-vinylphenyl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine[185] 2-(5-((1H-imidazol-4-yl)ethynyl)thiophen-2-yl)-N-tert-butylimidazo[1,2-a]pyrazin-3-amine hydrochloride[186] N-tert-butyl-2-(5-((3-methylpyridin-2-yl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine[187] N,N-dimethyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine[188] N-tert-butyl-2-(5-((2-(tert-butyldiphenylsilyl)thiazol-5-yl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine[189] 3-((5-(3-(tert-butylamino)imidazo[1,2-a]pyridin-2-yl)thiophen-2-yl)ethynyl)benzonitrile[190] N-tert-butyl-2-(5-(phenylethynyl)thiazol-2-yl)imidazo[1,2-a]pyridin-3-amine[191] N-tert-butyl-2-(5-(thiazol-5-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine[192] N-tert-butyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine hydrochloride[193] 6-chloro-N-cyclohexyl-2-(3-((6-methylpyridin-2-yl)ethynyl)phenyl)imidazo[1,2-a]pyridin-3-amine[194] 5,7-dimethyl-N-phenethyl-2-(5-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrimidin-3-amine[195] N-(3-methoxyphenethyl)-5,7-dimethyl-2-(5-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrimidin-3-amine[196] N-(3-methoxyphenethyl)-5,7-dimethyl-2-(4-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrimidin-3-amine[197] N-(3-methoxyphenethyl)-5,7-dimethyl-2-(5-(phenylethynyl)furan-2-yl)imidazo[1,2-a]pyrimidin-3-amine[198] N-(4-chlorobenzyl)-8-methyl-2-(5-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine[199] N-(3-methoxyphenethyl)-5-methyl-2-(4-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine[200] N-(2-methylhexan-2-yl)-2-(4-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine[201] N-phenethyl-2-(4-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine[202] N-(3-methoxyphenethyl)-2-(4-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine[203] 2-(4-(phenylethynyl)thiophen-2-yl)-N-(2-(thiophen-2-yl)ethyl)imidazo[1,2-a]pyrazin-3-amine[204] N-(4-chlorobenzyl)-2-(5-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine[205] N-(2-methylpentan-2-yl)-2-(5-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine[206] N-(cyclohexylmethyl)-2-(4-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine[207] N-(2-methoxybenzyl)-2-(5-(phenylethynyl)furan-2-yl)imidazo[1,2-a]pyrazin-3-amine[208] N-(cyclohexylmethyl)-2-(4-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine[209] N-(2-methylpentan-2-yl)-2-(4-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine[210] 8-bromo-6-methyl-2-(3-((6-methylpyridin-2-yl)ethynyl)phenyl)-N-(2,4,4-trimethylpentan-2-yl)imidazo[1,2-a]pyridin-3-amine[211] 8-bromo-N-cyclopentyl-6-methyl-2-(3-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyridin-3-amine[212] N-cyclopentyl-2-(4-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine[213] N-(1-phenylethyl)-2-(4-(henylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine[214] N-(2-methylpentan-2-yl)-2-(4-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine[215] 8-bromo-N-cyclohexyl-6-methyl-2-(5-(pyridin-2-ylethynyl)furan-2-yl)imidazo[1,2-a]pyridin-3-amine[216] N-cyclopentyl-2-(5-(phenylethynyl)furan-2-yl)imidazo[1,2-a]pyrazin-3-amine[217] N-(3-methoxyphenethyl)-7-methyl-2-(4-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrimidin-3-amine[218] 8-(benzyloxy)-2-(5-(phenylethynyl)thiophen-2-yl)-N-(2,4,4-trimethylpentan-2-yl)imidazo[1,2-a]pyridin-3-amine[219] 8-(benzyloxy)-N-cyclopentyl-2-(4-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine[220] 8-(benzyloxy)-N-(2-methylpentan-2-yl)-2-(4-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine[221] 6-chloro-N-(4-fluorobenzyl)-2-(5-(phenylethynyl)furan-2-yl)imidazo[1,2-a]pyridin-3-amine[222] 6-bromo-N-butyl-5-methyl-2-(4-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine[223] N-(furan-2-yl)-8-methyl-2-(5-(phenylethynyl)furan-2-yl)imidazo[1,2-a]pyridin-3-amine[224] N-(furan-2-yl)-2-(5-(phenylethynyl)furan-2-yl)imidazo[1,2-a]pyridin-3-amine[225] N-(furan-2-yl)-2-(5-(phenylethynyl)furan-2-yl)-7-propylimidazo[1,2-a]pyridin-3-amine[226] 5,7-dimethyl-2-(4-(phenylethynyl)thiophen-2-yl)-N-(3-(trifluoromethyl)phenyl)imidazo[1,2-a]pyrimidin-3-amine[227] 6-bromo-N-(4-chlorophenethyl)-8-methyl-2-(4-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine[228] N-(4-chlorophenethyl)-7-phenyl-2-(4-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine[229] N-phenethyl-7-phenyl-2-(4-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine[230] N-(4-chlorobenzyl)-5,7-dimethyl-2-(4-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine[231] 6-bromo-N-(4-chlorobenzyl)-5-methyl-2-(4-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine[232] 8-bromo-N-(4-chlorobenzyl)-6-methyl-2-(4-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine[233] N-(3-methoxyphenethyl)-2-(4-(phenylethynyl)thiophen-2-yl)-5-propylimidazo[1,2-a]pyridin-3-amine[234] 6-bromo-8-methyl-2-(4-(phenylethynyl)thiophen-2-yl)-N-(2-(thiophen-2-yl)ethyl)imidazo[1,2-a]pyridin-3-amine[235] 7-phenyl-2-(4-(phenylethynyl)thiophen-2-yl)-N-(2-(thiophen-2-yl)ethyl)imidazo[1,2-a]pyridin-3-amine[236] 6,8-dibromo-N-(2-methylpentan-2-yl)-2-(5-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine[237] 6-bromo-N-(2,6-dimethylphenyl)-8-methyl-2-(4-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine[238] N-cyclohexyl-2-(3-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyrazin-3-amine[239] 2-(3-(pyridin-2-ylethynyl)phenyl)-N-(2,4,4-trimethylpentan-2-yl)imidazo[1,2-a]pyrazin-3-amine[240] N-cyclopentyl-2-(4-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyrazin-3-amine[241] 8-chloro-2-(4-(pyridin-2-ylethynyl)phenyl)-6-(trifluoromethyl)-N-(2,4,4-trimethylpentan-2-yl)imidazo[1,2-a]pyridin-3-amine[242] N-(4-fluorophenyl)-2-(4-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyrazin-3-amine[243] N-cyclopentyl-2-(2-methyl-6-(phenylethynyl)pyridin-3-yl)imidazo[1,2-a]pyrazin-3-amine[244] N-cyclohexyl-2-(2-methyl-6-(phenylethynyl)pyridin-3-yl)imidazo[1,2-a]pyrazin-3-amine[245] N-cyclopentyl-2-(5-(pyridin-2-ylethynyl)furan-2-yl)imidazo[1,2-a]pyrazin-3-amine[246] 8-bromo-N-cyclopentyl-6-methyl-2-(5-(pyridin-2-ylethynyl)furan-2-yl)imidazo[1,2-a]pyridin-3-amine[247] N-cyclohexyl-2-(5-(pyridin-2-ylethynyl)furan-2-yl)imidazo[1,2-a]pyrazin-3-amine[248] 2-(5-(pyridin-2-ylethynyl)furan-2-yl)-N-(2,4,4-trimethylpentan-2-yl)imidazo[1,2-a]pyrazin-3-amine[249] N-cyclopentyl-2-(3-((6-methylpyridin-2-yl)ethynyl)phenyl)imidazo[1,2-a]pyrazin-3-amine[250] 8-bromo-N-cyclopentyl-6-methyl-2-(4-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyridin-3-amine[251] N-cyclohexyl-2-(3-((6-methylpyridin-2-yl)ethynyl)phenyl)imidazo[1,2-a]pyrazin-3-amine[252] N-(4-fluorophenyl)-2-(3-((6-methylpyridin-2-yl)ethynyl)phenyl)imidazo[1,2-a]pyrazin-3-amine[253] 2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)-N-(2,4,4-trimethylpentan-2-yl)imidazo[1,2-a]pyrimidin-3-amine[254] N-cyclohexyl-2-(3-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyrimidin-3-amine[255] 2-(3-(pyridin-2-ylethynyl)phenyl)-N-(2,4,4-trimethylpentan-2-yl)imidazo[1,2-a]pyrimidin-3-amine[256] 2-(6-(phenylethynyl)pyridin-3-yl)-N-(2,4,4-trimethylpentan-2-yl)imidazo[1,2-a]pyrimidin-3-amine[257] N-cyclopentyl-2-(5-(pyridin-2-ylethynyl)furan-2-yl)imidazo[1,2-a]pyrimidin-3-amine[258] N-tert-butyl-2-(5-(pyridin-2-ylethynyl)furan-2-yl)imidazo[1,2-a]pyrimidin-3-amine[259] N-cyclopentyl-2-(3-((6-methylpyridin-2-yl)ethynyl)phenyl)imidazo[1,2-a]pyrimidin-3-amine[260] N-cyclopentyl-2-(3-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyridin-3-amine[261] N-tert-butyl-2-(3-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyridin-3-amine[262] 2-(3-(pyridin-2-ylethynyl)phenyl)-N-(2,4,4-trimethylpentan-2-yl)imidazo[1,2-a]pyridin-3-amine[263] N-(4-fluorophenyl)-2-(3-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyridin-3-amine[264] N-tert-butyl-2-(4-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyridin-3-amine[265] N-cyclopentyl-2-(2-methyl-6-(phenylethynyl)pyridin-3-yl)imidazo[1,2-a]pyridin-3-amine[266] N-(4-fluorophenyl)-2-(2-methyl-6-(phenylethynyl)pyridin-3-yl)imidazo[1,2-a]pyridin-3-amine[267] N-cyclopentyl-6-methyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine[268] N-tert-butyl-6-methyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine[269] N-cyclohexyl-6-methyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine[270] 6-methyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)-N-(2,4,4-trimethylpentan-2-yl)imidazo[1,2-a]pyridin-3-amine[271] 6-methyl-2-(2-methyl-6-(phenylethynyl)pyridin-3-yl)-N-(2,4,4-trimethylpentan-2-yl)imidazo[1,2-a]pyridin-3-amine[272] N-cyclopentyl-6-methyl-2-(5-(pyridin-2-ylethynyl)furan-2-yl)imidazo[1,2-a]pyridin-3-amine[273] N-cyclohexyl-6-methyl-2-(3-((6-methylpyridin-2-yl)ethynyl)phenyl)imidazo[1,2-a]pyridin-3-amine[274] N-cyclohexyl-7-methyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine[275] 7-methyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)-N-(2,4,4-trimethylpentan-2-yl)imidazo[1,2-a]pyridin-3-amine[276] N-tert-butyl-7-methyl-2-(3-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyridin-3-amine[277] N-(4-fluorophenyl)-7-methyl-2-(3-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyridin-3-amine[278] N-tert-butyl-7-methyl-2-(4-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyridin-3-amine[279] N-(4-fluorophenyl)-7-methyl-2-(5-(pyridin-2-ylethynyl)furan-2-yl)imidazo[1,2-a]pyridin-3-amine[280] N-cyclohexyl-8-methyl-2-(6-(phenylethynyl)pyridin-3-yl)imidazo[1,2-a]pyridin-3-amine[281] N-cyclopentyl-2-(6-(phenylethynyl)pyridin-3-yl)imidazo[1,2-a]pyridin-3-amine[282] N-tert-butyl-2-(6-(phenylethynyl)pyridin-3-yl)imidazo[1,2-a]pyridin-3-amine[283] N-cyclohexyl-2-(6-(phenylethynyl)pyridin-3-yl)imidazo[1,2-a]pyridin-3-amine[284] 2-(6-(phenylethynyl)pyridin-3-yl)-N-(2,4,4-trimethylpentan-2-yl)imidazo[1,2-a]pyridin-3-amine[285] N-tert-butyl-2-(5-(pyridin-2-ylethynyl)furan-2-yl)imidazo[1,2-a]pyridin-3-amine[286] N-cyclohexyl-2-(5-(pyridin-2-ylethynyl)furan-2-yl)imidazo[1,2-a]pyridin-3-amine[287] N-(4-fluorophenyl)-2-(5-(pyridin-2-ylethynyl)furan-2-yl)imidazo[1,2-a]pyridin-3-amine[288] N-cyclohexyl-2-(3-((6-methylpyridin-2-yl)ethynyl)phenyl)imidazo[1,2-a]pyridin-3-amine[289] 2-(3-((6-methylpyridin-2-yl)ethynyl)phenyl)-N-(2,4,4-trimethylpentan-2-yl)imidazo[1,2-a]pyridin-3-amine[290] N-tert-butyl-5-methyl-2-(3-((6-methylpyridin-2-yl)ethynyl)phenyl)imidazo[1,2-a]pyridin-3-amine[291] 5-methyl-2-(3-((6-methylpyridin-2-yl)ethynyl)phenyl)-N-(2,4,4-trimethylpentan-2-yl)imidazo[1,2-a]pyridin-3-amine[292] N-cyclohexyl-5,7-dimethyl-2-(3-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyrimidin-3-amine[293] N-cyclohexyl-5,7-dimethyl-2-(2-methyl-6-(phenylethynyl)pyridin-3-yl)imidazo[1,2-a]pyrimidin-3-amine[294] N-cyclopentyl-5,7-dimethyl-2-(5-(pyridin-2-ylethynyl)furan-2-yl)imidazo[1,2-a]pyrimidin-3-amine[295] N-tert-butyl-5,7-dimethyl-2-(5-(pyridin-2-ylethynyl)furan-2-yl)imidazo[1,2-a]pyrimidin-3-amine[296] N-(4-fluorophenyl)-8-methyl-2-(3-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyridin-3-amine[297] N-cyclohexyl-8-methyl-2-(4-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyridin-3-amine[298] N-cyclohexyl-7-ethyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine[299] 7-ethyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)-N-(2,4,4-trimethylpentan-2-yl)imidazo[1,2-a]pyridin-3-amine[300] N-cyclohexyl-7-ethyl-2-(3-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyridin-3-amine[301] N-cyclopentyl-7-ethyl-2-(4-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyridin-3-amine[302] N-cyclopentyl-7-ethyl-2-(6-(phenylethynyl)pyridin-3-yl)imidazo[1,2-a]pyridin-3-amine[303] N-tert-butyl-7-ethyl-2-(6-(phenylethynyl)pyridin-3-yl)imidazo[1,2-a]pyridin-3-amine[304] N-tert-butyl-7-ethyl-2-(5-(pyridin-2-ylethynyl)furan-2-yl)imidazo[1,2-a]pyridin-3-amine[305] 7-isopropyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)-N-(2,4,4-trimethylpentan-2-yl)imidazo[1,2-a]pyridin-3-amine[306] N-tert-butyl-7-isopropyl-2-(3-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyridin-3-amine[307] N-tert-butyl-7-isopropyl-2-(4-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyridin-3-amine[308] N-cyclohexyl-7-isopropyl-2-(5-(pyridin-2-ylethynyl)furan-2-yl)imidazo[1,2-a]pyridin-3-amine[309] N-tert-butyl-7-isopropyl-2-(3-((6-methylpyridin-2-yl)ethynyl)phenyl)imidazo[1,2-a]pyridin-3-amine[310] 6-chloro-N-cyclopentyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine[311] N-tert-butyl-6-chloro-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine[312] 6-chloro-N-cyclohexyl-2-(3-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyridin-3-amine[313] 6-chloro-2-(3-(pyridin-2-ylethynyl)phenyl)-N-(2,4,4-trimethylpentan-2-yl)imidazo[1,2-a]pyridin-3-amine[314] N-tert-butyl-6-chloro-2-(4-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyridin-3-amine[315] 6-chloro-N-cyclohexyl-2-(4-(pyridin-2-ylethynyl)phenyl)imidazo[1,2-a]pyridin-3-amine[316] N-tert-butyl-6-chloro-2-(5-(pyridin-2-ylethynyl)furan-2-yl)imidazo[1,2-a]pyridin-3-amine[317] 6-chloro-N-cyclohexyl-2-(5-(pyridin-2-ylethynyl)furan-2-yl)imidazo[1,2-a]pyridin-3-amine[318] 6-chloro-2-(5-(pyridin-2-ylethynyl)furan-2-yl)-N-(2,4,4-trimethylpentan-2-yl)imidazo[1,2-a]pyridin-3-amine[319] 6-chloro-N-cyclopentyl-2-(3-((6-methylpyridin-2-yl)ethynyl)phenyl)imidazo[1,2-a]pyridin-3-amine[320] N-tert-butyl-6-chloro-2-(3-((6-methylpyridin-2-yl)ethynyl)phenyl)imidazo[1,2-a]pyridin-3-amine[321] N-tert-butyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine bis-hydrochloride[322] N-methyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine[323] N-tert-butyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine bis-hydrochloride[324] [2-(5-pyridin-2-ylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(1,1,3,3-tetramethyl-butyl)-amine[325] tert-butyl-[2-(5-pyrimidin-2-ylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-amine hydrochloride[326] {2-[5-(3-amino-pyridin-2-ylethynyl)-thiophen-2-yl]-imidazo[1,2-a]pyridin-3-yl}-tert-butyl-amine[327] tert-butyl-[2-(5-pyridin-2-ylethynyl-thiazol-2-yl)-imidazo[1,2-a]pyridin-3-yl]-amine[328] tert-butyl-[2-(2-pyridin-2-ylethynyl-thiazol-5-yl)-imidazo[1,2-a]pyridin-3-yl]-amine[329] tert-butyl-{2-[5-(6-fluoro-pyridin-2-ylethynyl)-thiophen-2-yl]-imidazo[1,2-a]pyridin-3-yl}-amine hydrochloride[330] tert-butyl-{2-[5-(3-chloro-5-fluoro-phenylethynyl)-thiophen-2-yl]-imidazo[1,2-a]pyridin-3-yl}-amine hydrochloride[331] tert-butyl-[2-(5-pyridin-2-ylethynyl-thiophen-2-yl)-imidazo[1,2-b]pyridazin-3-yl]-amine hydrochloride[332] tert-butyl-[2-(5-thiazol-2-ylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-amine hydrochloride[333] tert-butyl-{2-[5-(3-trifluoromethoxy-phenylethynyl)-thiophen-2-yl]-imidazo[1,2-a]pyrazin-3-yl}-amine[334] tert-butyl-{2-[5-(3-[1,3]dioxolan-2-yl-phenylethynyl)-thiophen-2-yl]-imidazo[1,2-a]pyridin-3-yl}-amine[335] tert-butyl-{2-[5-(3,5-dimethyl-phenylethynyl)-thiophen-2-yl]-imidazo[1,2-a]pyridin-3-yl}-amine hydrochloride[336] tert-butyl-{2-[5-(3-fluoro-pyridin-2-ylethynyl)-thiophen-2-yl]-imidazo[1,2-a]pyridin-3-yl}-amine hydrochloride[337] tert-butyl-{2-[5-(3-methyl-3H-imidazol-4-ylethynyl)-thiophen-2-yl]-imidazo[1,2-a]pyridin-3-yl}-amine hydrochloride and[338] tert-butyl-{2-[5-(5-chloro-thiophen-2-ylethynyl)-thiophen-2-yl]-imidazo[1,2-a]pyridin-3-yl}-amine hydrochloride[339] tert-butyl-{2-[5-(5-methyl-pyridin-2-ylethynyl)-thiophen-2-yl]-imidazo[1,2-a]pyridin-3-yl}-amine hydrochloride[340] 1-{3-[5-(3-tert-butylamino-imidazo[1,2-a]pyridin-2-yl)-thiophen-2-ylethynyl]-phenyl}-ethanone hydrochloride[341] {3-[5-(3-tert-butylamino-imidazo[1,2-a]pyridin-2-yl)-thiophen-2-ylethynyl]-phenyl}-methanol hydrochloride[342] N-tert-butyl-2-(5-((3-methoxypyridin-2-yl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine[343] N-tert-butyl-2-(5-(thiophen-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine hydrochloride[344] 5-((5-(3-(tert-butylamino)imidazo[1,2-a]pyridin-2-yl)thiophen-2-yl)ethynyl)-2-fluorobenzonitrile hydrochloride[345] N-tert-butyl-2-(5-((3,4-difluorophenyl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine[346] N-tert-butyl-2-(5-((3-(methoxymethyl)phenyl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine[347] 2-(5-((3-aminophenyl)ethynyl)thiophen-2-yl)-N-tert-butylimidazo[1,2-a]pyridin-3-amine hydrochloride[348] N-tert-butyl-2-(5-((4-fluoro-3-methylphenyl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine hydrochloride[349] N-tert-butyl-2-(5-((3,5-difluorophenyl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine[350] N-tert-butyl-2-(5-(thiophen-3-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine hydrochloride[351] N-tert-butyl-2-(5-((3-methylpyridin-2-yl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine hydrochloride[352] 3-((5-(3-(tert-butylamino)imidazo[1,2-a]pyridin-2-yl)thiophen-2-yl)ethynyl)benzenesulfonamide hydrochloride[353] 3-((5-(3-(tert-butylamino)imidazo[1,2-a]pyridin-2-yl)hiophen-2-yl)ethynyl)benzoic acid[354] 3-((5-(3-(tert-butylamino)imidazo[1,2-a]pyridin-2-yl)thiophen-2-yl)ethynyl)benzamide hydrochloride[355] N-(3-((5-(3-(tert-butylamino)imidazo[1,2-a]pyridin-2-yl)thiophen-2-yl)ethynyl)phenyl)acetamide[356] N-tert-butyl-N-methyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine[357] N,N-dimethyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine[358] N-tert-butyl-N-methyl-2-(5-(pyridin-2-ylethynyl)thiazol-2-yl)imidazo[1,2-a]pyridin-3-amine[359] (6-((5-(3-(tert-butylamino)imidazo[1,2-a]pyridin-2-yl)thiophen-2-yl)ethynyl)pyridin-2-yl)methanol[360] N-(3-((5-(3-(tert-butylamino)imidazo[1,2-a]pyridin-2-yl)thiophen-2-yl)ethynyl)phenyl)methanesulfonamide[361] N-tert-butyl-8-methyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine hydrochloride[362] 2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine[363] N-tert-butyl-2-(5-((3-chlorophenyl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine[364] N-tert-butyl-2-(5-((2,3-difluorophenyl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine
45. A process for preparing a bicyclic imidazo-3-yl-amine compound corresponding to formula I of claim 1, comprising the steps reacting at least one compound of the formula II,
46. The process of claim 45, further comprising at least one of the steps of purifying or isolating at least one of the compounds according to formulas I, V, VII, XII, or XIII or converting one of these compounds into a salt which may then be purified or isolated.
47. The process of claim 45, wherein X represents a halogen or a sulfonic acid ester.
48. The process of claim 45, wherein X represents chlorine, bromine or trifluoromethanesulfonate.
49. A process for producing a bicyclic imidazo-3-yl-amine compound corresponding to formula I of claim 1, comprising the steps of reacting a compound of formula V,
50. The process of claim 49, further comprising at least one of the steps of purifying or isolating at least one of the compounds according to formulas I, IX or X or converting one of these compounds into a salt which may then be purified or isolated.
51. The process of claim 49, wherein X represents a halogen or a sulfonic acid ester.
52. The process of claim 49, wherein X represents chlorine, bromine or trifluoromethanesulfonate.
53. A pharmaceutical composition containing at last one compound according to claim 1 and one or more physiologically acceptable auxiliary substances.
54. A method of inhibiting the mGluR5 receptor in a subject, said method comprising the step of administering to said subject an effective mGluR5 receptor inhibiting amount of a compound according to claim 1.
55. A method of treating pain comprising the step of administering to a patient a pharmaceutically effective amount of a compound according to claim 1.
56. The method of claim 55, wherein said pain selected from the group consisting of acute pain, chronic pain, neuropathic pain and visceral pain.
57. A method of producing a pharmaceutical formulation comprising the step of combining a compound according to claim 1 with one or more physiologically acceptable auxiliary substances.

Priority Claims (1)

Number	Date	Country	Kind
10 2004 044 884	Sep 2004	DE	national

US Referenced Citations (1)

Number	Name	Date	Kind
20030225070	Mutel et al.	Dec 2003	A1

Foreign Referenced Citations (7)

Number	Date	Country
199 48 438	Jun 2001	DE
WO 0127110	Apr 2001	WO
WO 0127119	Apr 2001	WO
WO 0230428	Apr 2002	WO
WO 0246166	Jun 2002	WO
WO 02080911	Oct 2002	WO
WO 03051315	Jun 2003	WO

Related Publications (1)

	Number	Date	Country
	20070155965 A1	Jul 2007	US

Continuations (1)

	Number	Date	Country
Parent	PCT/EP2005/054436	Sep 2005	US
Child	11685953		US

Substituted bicyclic imidazo-3-ylamine compounds

Information

Patent Number

Date Filed

Date Issued

Inventors

Original Assignees

Examiners

Agents

CPC

US Classifications

Field of Search

US

International Classifications

Abstract

Description

Claims

Priority Claims (1)

US Referenced Citations (1)

Foreign Referenced Citations (7)

Related Publications (1)

Continuations (1)