JP2002255964A - Imidazopyridine derivative - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a new imidazopyridine derivative having high antitumor activity. SOLUTION: This new imidazopyridine derivative is expressed by the formula (R<1> is a substituted phenyl group, substituted heterocyclic ring or the like; R<2> is H, an aliphatic acyl or the like; R<3> , R<4> , R<5> , R<6> , R<7> and R<8> are each H, an alkyl, a halogen atom or the like; and X<1> is O, S or the like).

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a novel imidazopyridine derivative having an excellent tumor growth inhibitory activity.

[0002]

BACKGROUND ART Compounds having a chemical structure related to the compound of the present invention include:

[0003]

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However, it has not been known that the compound has a tumor growth inhibitory activity.

[0005]

SUMMARY OF THE INVENTION The present inventors have conducted intensive studies over many years on the synthesis of derivatives having excellent tumor growth inhibitory activity and their pharmacological activities. The present inventors have found that they have growth inhibitory activity and completed the present invention.

[0006]

The novel imidazopyridine derivative of the present invention has the general formula

[0007]

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[Wherein, R ¹ and R ² are the same or different and are each a group represented by the formula R ⁹ -X ^2- wherein R ⁹ is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, An alkyl group having 1 to 6 carbon atoms, which is substituted with 1 to 3 carbon atoms by a substituent selected from the group, a cycloalkyl group having 3 to 8 members, and a 3 alkyl group, which is 1 to 3 substituted with a substituent selected from the following β group. To an 8-membered cycloalkyl group, an aryl group having 6 to 14 carbon atoms,
6 carbon atoms substituted with 1 to 5 substituents selected from the group
To 14 aryl groups, heterocyclic groups, heterocyclic groups substituted by 1 to 5 substituents selected from the following β group, and carbon atoms of 7
To 15 aralkyl groups, an aralkyl group having 7 to 15 carbon atoms substituted by 1 to 5 with a substituent selected from the following β group, an arylalkenyl group having 8 to 16 carbon atoms,
X represents an arylalkenyl group having 8 to 16 carbon atoms or a carbamoyl group substituted by 1 to 5 with a substituent selected from the following β group, and X ² represents a single bond, a carbonyl group (−
C (= O)-), oxycarbonyl group (-OC (= O)
-), aminocarbonyl group (-NHC (= O) - shows a) -) or a sulfonyl group (-SO _2. ), R ³ , R
⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ may be the same or different and are each a halogen atom, a cyano group, a nitro group, a group of the formula R ¹⁰ -X ³ (where R ¹⁰ is a hydrogen atom, To 6 alkyl groups, an alkyl group having 1 to 6 carbon atoms substituted by 1 to 3 with a substituent selected from the following α group, a 3 to 8 membered cycloalkyl group, a substitution selected from the following β group 1 to 3
A substituted 3- to 8-membered cycloalkyl group, an aryl group having 6 to 14 carbon atoms, an aryl group having 6 to 14 carbon atoms substituted by 1 to 5 with a substituent selected from the following β group, heterocycle Group, heterocyclic group substituted with 1 to 5 substituents selected from the following β group, aralkyl group having 7 to 15 carbon atoms, carbon number substituted with 1 to 5 the substituent selected from the following β group 7 to 15 aralkyl groups, 8 to 16 carbon atoms of an arylalkenyl group, or 8 to 16 carbon atoms substituted by 1 to 5 substituents selected from the following β group:
X ³ represents a single bond, an oxygen atom (—O—), a sulfur atom (—S—), a carbonyl group (—C (＝ O) —), an oxycarbonyl group (—OC ( =
O)-), a carbonyloxy group (-C (= O) O-),
It represents an aminocarbonyl group (—NHC (＝ O) —) or a sulfonyl group (—SO ₂ —). ) Or the formula R ¹¹ R ¹² N
-Groups wherein R ¹¹ and R ¹² are the same or different and are of the formula R
¹³ -X ⁴ groups (wherein, R ¹³ is a hydrogen atom, a carbon number of 1 to 6
Alkyl groups, an alkyl group having 1 to 6 carbon atoms substituted by 1 to 3 with a substituent selected from the following α group, a 3- to 8-membered cycloalkyl group, a substituent selected from the following β group 1 to 3 substituted 3 to 8 membered cycloalkyl group, 6 to 14 carbon atom aryl group, 6 to 14 carbon atoms substituted by 1 to 5 substituents selected from the following β group
Aryl groups, heterocyclic groups, heterocyclic groups substituted with 1 to 5 substituents selected from the following β group, 7 to 15 carbon atoms
Aralkyl groups, and 1 substituent group selected from the following β group
5 to 5 substituted aralkyl groups having 7 to 15 carbon atoms,
X represents an arylalkenyl group having 8 to 16 carbon atoms, or an arylalkenyl group having 8 to 16 carbon atoms substituted with 1 to 5 substituents selected from the following β group;
⁴ is a single bond, a carbonyl group (-C (= O)-), an oxycarbonyl group (-OC (= O)-), an aminocarbonyl group (-NHC (= O)-) or a sulfonyl group (-SO
_2- ) is shown. ). Or R ³ , R ⁴ , R ⁷ and R ⁸ have the same meaning, and a benzene ring which may have a substituent together with R ⁵ and R ⁶ and the carbon to which each is bonded. Or R ³ , R ⁴ , R ⁵ and R ⁸ have the same meaning, and together with R ⁶ and R ⁷ and the carbon to which each is bonded, a benzene ring which may have a substituent is R ³ , R ⁴ , R ⁵ and R ⁶ have the same meaning, and R ⁷ and R ⁸ may have a substituent together with the carbon to which they are bonded. Is shown.

X ¹ is an oxygen atom, a sulfur atom, or a compound of the formula N
H group is shown. Provided that R ¹ , R ² , R ³ , R ⁵ , R ⁶ , R ⁷ and R ⁸ are hydrogen atoms, R ⁴ is a methyl group and X ¹ is a sulfur atom. Or a pharmacologically acceptable salt thereof.

Group α: a halogen atom, a cyano group, a nitro group, an oxodioxorenylmethyl group, a group of the formula R ¹⁴ -X ⁵ (where R ¹⁴ is a hydrogen atom, an amino group, a carbon number of 1 to 2)
0 alkyl groups, 1 substituent group selected from the following γ group
3 to 3 substituted alkyl groups having 1 to 20 carbon atoms, 3
To an 8-membered cycloalkyl group, a 3- to 8-membered cycloalkyl group substituted by 1 to 3 with a substituent selected from the following group δ, an aryl group having 6 to 14 carbon atoms, selected from the following group δ 6 to 1 carbon atoms substituted by 1 to 5 substituents
4 aryl groups, heterocyclic groups, heterocyclic groups substituted by 1 to 3 substituents selected from the following group δ, 7 to 1 carbon atoms
5 aralkyl groups, an aralkyl group having 7 to 15 carbon atoms substituted by 1 to 5 with a substituent selected from the following δ group, an arylalkenyl group having 8 to 16 carbon atoms, or selected from the following δ group Represents an arylalkenyl group having 8 to 16 carbon atoms, which is substituted with 1 to 5 substituents,
X ⁵ is a single bond, an oxygen atom (—O—), a sulfur atom (—S
-), Carbonyl group (-C (= O)-), oxycarbonyl group (-OC (= O)-), carbonyloxy group (-
C (= O) O-), aminocarbonyl group (-NHC (=
O) -) or a sulfonyl group (-SO ₂ - shows a). ),
And a group represented by the formula R ¹⁶ R ¹⁷ N— (wherein R ¹⁶ and R ¹⁷ are the same or different, and a group represented by the formula R ¹⁸ —X ⁶ (wherein R ¹⁸ is a hydrogen atom, having 1 to 20 carbon atoms) An alkyl group having 1 to 20 carbon atoms substituted by 1 to 3 substituents selected from the following γ group:
Alkyl group, 3- to 8-membered cycloalkyl group, 3- to 8-membered cycloalkyl group substituted by 1 to 3 with a substituent selected from the following group δ, aryl group having 6 to 14 carbon atoms, an aryl group having 6 to 14 carbon atoms and a heterocyclic group substituted with 1 to 5 substituents selected from the group δ, a heterocyclic group substituted with 1 to 5 carbon atoms with a substituent selected from the following group δ, carbon 7 to 15 aralkyl groups, 7 to 1 carbon atoms substituted by 1 to 5 substituents selected from the following δ group:
5 aralkyl groups, arylalkenyl groups having 8 to 16 carbon atoms, or 1
X ⁵ represents an arylalkenyl group having 8 to 16 carbon atoms, wherein X ⁶ represents a single bond, a carbonyl group (—C
(= O)-), oxycarbonyl group (-OC (= O)
-), aminocarbonyl group (-NHC (= O) - shows a) -) or a sulfonyl group (-SO _2. Or R ¹⁶ and R ¹⁷ together with the nitrogen atom to which they are attached,
1 to 5 of a heterocyclic group or a substituent selected from the following δ group:
Indicate a substituted heterocyclic group. However, the formula R ¹⁴ -X ⁵ does not represent an alkyl group having 1 to 6 carbon atoms. ).

Group β: a halogen atom, a cyano group, a nitro group, a group of the formula R ¹⁸ -X ⁷ (where R ¹⁸ is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, selected from the following group γ: An alkyl group having 1 to 6 carbon atoms, which is substituted by 1 to 3 substituents, a 3 to 8 membered cycloalkyl group, a 3 to 8 membered cycloalkyl, which is substituted by 1 to 3 substituent (s) selected from the following group δ: Alkyl group, aryl group having 6 to 14 carbon atoms, the following δ
6 carbon atoms substituted with 1 to 5 substituents selected from the group
To 14 aryl groups, heterocyclic groups, heterocyclic groups substituted with 1 to 5 substituents selected from the following group δ, and carbon atoms of 7
To 15 aralkyl groups, an aralkyl group having 7 to 15 carbon atoms substituted by 1 to 5 with a substituent selected from the following δ group, an arylalkenyl group having 8 to 16 carbon atoms,
Or an arylalkenyl group having 8 to 16 carbon atoms, which is substituted by 1 to 5 with a substituent selected from the following δ group, wherein X ⁷ is a single bond, an oxygen atom (-O-), a sulfur atom (- S-), carbonyl group (-C (= O)-), oxycarbonyl group (-OC (= O)-), carbonyloxy group (-C (= O) O-), aminocarbonyl group (-NH
C (= O) -) or a sulfonyl group (-SO ₂ - shows a). ) And a formula R ¹⁹ R ²⁰ N-group (wherein R ¹⁹ and R ²⁰
Are the same or different and have the formula R ²¹ -X ^8
21 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkyl group having 1 to 6 carbon atoms substituted by 1 to 3 with a substituent selected from the following γ group, and a 3- to 8-membered cycloalkyl group A 3- to 8-membered cycloalkyl group substituted by 1 to 3 with a substituent selected from the following δ group, an aryl group having 6 to 14 carbon atoms, and a 1 to 5 substituted by a substituent selected from the following δ group: Aryl group having 6 to 14 carbon atoms, heterocyclic group, heterocyclic group substituted by 1 to 5 with a substituent selected from the following δ group, aralkyl group having 7 to 15 carbon atoms, from the following δ group An aralkyl group having 7 to 15 carbon atoms substituted with 1 to 5 substituents, an arylalkenyl group having 8 to 16 carbon atoms, or 1 to 5 substituted with a substituent selected from the following δ group: Represents an arylalkenyl group having 8 to 16 carbon atoms. X ⁸ represents a single bond, a carbonyl group (-C (= O) -) , oxycarbonyl group (-OC (=
O)-), aminocarbonyl group (-NHC (= O)-)
Or a sulfonyl group - shows the (-SO _2). ). ). Group γ: an alkyl group having 1 to 6 carbon atoms, an alkyl group having 1 to 6 carbon atoms substituted with a hydroxyl group, an alkoxy group having 1 to 6 carbon atoms, a carboxyl group, an amino group, and 1 carbon atom
Or 6-substituted mono- or dialkylamino group with alkyl group, a heterocyclic group, 1 to 5-substituted heterocyclic group with a substituent selected from the following δ group, CH ₃ O (CH ₂ CH
₂ O) _n groups (where n is an integer of 1 to 6);
Halogen atom. Group δ: alkyl group having 1 to 6 carbon atoms, 1 to 6 carbon atoms
Alkoxy groups, halogen atoms, amino groups, and 1
Or an amino group substituted with two alkyl groups having 1 to 6 carbon atoms or an alkylcarbonyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms substituted with an alkyl carbonyl group having 1 to 6 carbon atoms. Alkyl groups.

Examples of the “alkyl group having 1 to 20 carbon atoms” or the “alkyl group having 1 to 6 carbon atoms” such as R ⁹ include methyl, ethyl, n-propyl, isopropyl, n-butyl, Isobutyl, s-butyl, tert-butyl, n-pentyl, isopentyl, 2-methylbutyl, neopentyl, 1-ethylpropyl, n-hexyl, isohexyl, 4-methylpentyl, 3-methylpentyl, 2-methylpentyl, 1- Methylpentyl,
3,3-dimethylbutyl, 2,2-dimethylbutyl,
1,1-dimethylbutyl, 1,2-dimethylbutyl,
1,3-dimethylbutyl, 2,3-dimethylbutyl, 2
-Ethyl butyl, heptyl, octyl, nonyl, decanyl, undecanyl, dodecanyl, tridecanyl, tetradecanyl, pentadecanyl, hexadecanyl, heptadecanyl, octadecanyl, nonadecanyl, eicosanyl and the like. , Having 1 to 4 carbon atoms, more preferably a methyl or ethyl group, and most preferably a methyl group.

Examples of the "3- to 8-membered cycloalkyl group" such as R ⁹ include a cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl group, and preferably a cyclopropyl or cyclobutyl group. is there.

Examples of the "aryl group having 6 to 14 carbon atoms" such as R ⁹ include phenyl, indenyl, naphthyl, phenanthrenyl, anthracenyl and the like, and a phenyl group is preferable.

The "heterocyclic group" such as R ⁹ is a sulfur atom,
5 to 7 containing 1 to 3 oxygen atoms and / or nitrogen atoms
Membered heterocyclic group, for example, furyl, thienyl, pyrrolyl, azepinyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl,
Aromatic heterocyclic groups such as 1,2,3-oxadiazolyl, triazolyl, tetrazolyl, thiadiazolyl, pyranyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl and morpholinyl, thiomorpholinyl, pyrrolidinyl, pyrrolinyl, imidazolidinyl, imidazolinyl,
Partially or completely reduced groups corresponding to these groups such as pyrazolidinyl, pyrazolinyl, piperidyl and piperazinyl can be mentioned, and the above “5 to 7”
The `` membered heterocyclic group '' may be condensed with another cyclic group, for example, isobenzofuranyl, chromenyl, xanthenyl, phenoxathiinyl, indolizinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolizinyl, isoquinolyl Quinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, carbazolyl, carbolinyl, acridinyl, isoindolinyl, and among the above "heterocyclic groups", preferably a pyridyl group (particularly, pyridine-3- Il group).

The "aralkyl group having 7 to 15 carbon atoms" such as R ⁹ includes, for example, benzyl, α-naphthylmethyl, β-naphthylmethyl, indenylmethyl, phenanthrenylmethyl, anthracenylmethyl , Diphenylmethyl, triphenylmethyl, 1-phenethyl, 2-
Phenethyl, 1-naphthylethyl, 2-naphthylethyl, 1-phenylpropyl, 2-phenylpropyl, 3
-Phenylpropyl, 1-naphthylpropyl, 2-naphthylpropyl, 3-naphthylpropyl, 1-phenylbutyl, 2-phenylbutyl, 3-phenylbutyl, 4-
Phenylbutyl, 1-naphthylbutyl, 2-naphthylbutyl, 3-naphthylbutyl, 4-naphthylbutyl, 1-
Phenylpentyl, 2-phenylpentyl, 3-phenylpentyl, 4-phenylpentyl, 5-phenylpentyl, 1-naphthylpentyl, 2-naphthylpentyl,
3-naphthylpentyl, 4-naphthylpentyl, 5-naphthylpentyl, 1-phenylhexyl, 2-phenylhexyl, 3-phenylhexyl, 4-phenylhexyl, 5-phenylhexyl, 6-phenylhexyl,
-Naphthylhexyl, 2-naphthylhexyl, 3-naphthylhexyl, 4-naphthylhexyl, 5-naphthylhexyl, 6-naphthylhexyl and the like, preferably benzyl or phenethyl, more preferably benzyl Group.

Examples of the “arylalkenyl group having 8 to 16 carbon atoms” such as R ⁹ include styryl, 2-
Examples thereof include a naphthylvinyl group, and a styryl group is preferable.

Examples of the “halogen atom” such as R ³ include:
Examples thereof include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, preferably a fluorine or chlorine atom, and more preferably a fluorine atom.

Examples of the "oxodioxorenylmethyl group" in the above α group include, for example, (5-phenyl-2-oxo-
1,3-dioxolen-4-yl) methyl, [5- (4
-Methylphenyl) -2-oxo-1,3-dioxolen-4-yl] methyl, [5- (4-methoxyphenyl) -2-oxo-1,3-dioxolen-4-yl]
Methyl, [5- (4-fluorophenyl) -2-oxo-1,3-dioxolen-4-yl] methyl, [5-
(4-Chlorophenyl) -2-oxo-1,3-dioxolen-4-yl] methyl, (2-oxo-1,3-dioxolen-4-yl) methyl, (5-methyl-2-oxo-1, 3-dioxolen-4-yl) methyl, (5
-Ethyl-2-oxo-1,3-dioxolen-4-yl) methyl, (5-propyl-2-oxo-1,3-dioxolen-4-yl) methyl, (5-isopropyl-
2-oxo-1,3-dioxolen-4-yl) methyl, a (5-butyl-2-oxo-1,3-dioxolen-4-yl) methyl group, and the like.
Methyl-2-oxo-1,3-dioxolen-4-yl) methyl group.

R ⁵ and R ⁶ together with the carbon to which each is attached represent a benzene ring which may have a substituent, or R ⁶ and R ⁷ together with the carbon to which each is attached A substituent in the case of showing a benzene ring which may have a substituent, or showing a benzene ring which may have a substituent together with carbon atoms to which R ⁷ and R ⁸ are bonded; Represents a halogen atom, a cyano group, a nitro group,
A group of the formula R ¹⁰ -X ³ (wherein R ¹⁰ is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, and 1 to 6 carbon atoms substituted by 1 to 3 substituents selected from the following α group) An alkyl group of 3
To an 8-membered cycloalkyl group, a 3- to 8-membered cycloalkyl group substituted by 1 to 3 with a substituent selected from the following β group, an aryl group having 6 to 14 carbon atoms, selected from the following β group 6 to 1 carbon atoms substituted by 1 to 5 substituents
4 aryl groups, heterocyclic groups, heterocyclic groups substituted with 1 to 5 substituents selected from the following β group, C 7 to C 1
5 aralkyl groups, an aralkyl group having 7 to 15 carbon atoms substituted by 1 to 5 with a substituent selected from the following β group, an arylalkenyl group having 8 to 16 carbon atoms, or selected from the following β group Represents an arylalkenyl group having 8 to 16 carbon atoms, which is substituted with 1 to 5 substituents,
X ³ represents a single bond, an oxygen atom (—O—), a sulfur atom (—S
-), Carbonyl group (-C (= O)-), oxycarbonyl group (-OC (= O)-), carbonyloxy group (-
C (= O) O-), aminocarbonyl group (-NHC (=
O) -) or a sulfonyl group (-SO ₂ - shows a). ),
Or, wherein R ^{1 1} R ¹² N-group (wherein, R ¹¹ and R ¹² are the same or different, wherein R ¹³ -X ⁴ group (wherein, R ¹³ is 1 to 6 hydrogen atoms, carbon atoms Alkyl groups, an alkyl group having 1 to 6 carbon atoms substituted by 1 to 3 substituents selected from the following α group, a 3 to 8 membered cycloalkyl group, a substituent selected from the following β group: 1 to 3 substituted 3 to 8 membered cycloalkyl group, 6 to 14 carbon atom aryl group, 6 to 14 carbon atom aryl group substituted by 1 to 5 substituents selected from the following β group , A heterocyclic group, the following β
A heterocyclic group substituted by 1 to 5 carbon atoms with a substituent selected from the group; an aralkyl group having 7 to 15 carbon atoms;
5 aralkyl groups, arylalkenyl groups having 8 to 16 carbon atoms, or 1
X ⁴ represents an arylalkenyl group having 8 to 16 carbon atoms, wherein X ⁴ represents a single bond, a carbonyl group (—C
(= O)-), oxycarbonyl group (-OC (= O)
-), aminocarbonyl group (-NHC (= O) - shows a) -) or a sulfonyl group (-SO _2. ). ), And is preferably a hydrogen atom.

Examples of the monoalkylamino group substituted with an alkyl group having 1 to 6 carbon atoms, such as group δ, include, for example, methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, isobutylamino S-butylamino, tert-butylamino, n-pentylamino, isopentylamino, 2-methylbutylamino, neopentylamino, 1-ethylpropylamino, n-hexylamino, isohexylamino, 4-methylpentylamino , 3-methylpentylamino, 2-
Methylpentylamino, 1-methylpentylamino,
3,3-dimethylbutylamino, 2,2-dimethylbutylamino, 1,1-dimethylbutylamino, 1,2-dimethylbutylamino, 1,3-dimethylbutylamino,
Examples thereof include 2,3-dimethylbutylamino and 2-ethylbutylamino, and preferably a methylamino group.

Examples of the dialkylamino group substituted with an alkyl group having 1 to 6 carbon atoms such as group δ include dimethylamino, ethylmethylamino, diethylamino, dipropylamino, diisopropylamino, dibutylamino, diisobutylamino, Di (s-butyl) amino, di (tert-butyl) amino, dipentylamino, diisopentylamino, di (2-methylbutyl) amino, dineopentylamino, di (1-ethylpropyl) amino, dihexylamino, Isohexylamino, di (4-methylpentyl) amino, di (3-methylpentyl) amino, di (2-methylpentyl) amino, di (1-methylpentyl) amino, di (3,3-dimethylbutyl) amino , Di (2,2-dimethylbutyl) amino, di (1,1
-Dimethylbutyl) amino, di (1,2-dimethylbutyl) amino, di (1,3-dimethylbutyl) amino, di (2,3-dimethylbutyl) amino, di (2-ethylbutyl) amino and the like. Preferably, it is a dimethylamino group.

Among the compounds of the present invention, (1) R ¹ is preferably an unsubstituted phenyl group, an unsubstituted pyridyl group, an alkyl group having 1 to 6 carbon atoms, To 6 alkyl-oxy groups, alkyl groups having 1 to 6 carbon atoms substituted by 1 to 3 halogen atoms, alkyl-carbonyl groups having 1 to 6 carbon atoms, hydroxyl groups, halogen atoms, nitro groups, cyano groups An aminocarbonyl group, an aminocarbonyl group substituted with 1 to 2 alkyl groups having 1 to 6 carbon atoms, an alkyl group having 1 to 6 carbon atoms,
A carbonyl group, a phenyl group or a pyridyl group, which is monosubstituted by an alkyl group having 1 to 6 carbon atoms and substituted by 1 to 3 carbon atoms, and is substituted by 1 to 3 carbon atoms. ) R ¹ is an alkyl group having 1 to 6 carbon atoms, an alkyl-oxy group having 1 to 6 carbon atoms, or 1 to 6 carbon atoms substituted with 1 to 3 halogen atoms.
One alkyl group, an alkyl-carbonyl group having 1 to 6 carbon atoms, a halogen atom or an aminocarbonyl group mono-substituted with an alkyl group having 1 to 6 carbon atoms,
A compound which is a phenyl group or a pyridyl group, (3) a phenyl group or a pyridyl group in which R ¹ is mono-substituted by a methyl group, a methoxy group, a trifluoromethyl group, a methylcarbonyl group, a halogen atom or a methylaminocarbonyl group; compounds, (4-1) R ² is a hydrogen atom, the 1 to 6 carbon atoms alkyl - carbonyl group, a halogen atoms and / or 1 to 3-substituted having 1 to 6 alkyl carbons with an amino group - group An aryl-carbonyl group having 6 to 14 carbon atoms, an aryl-carbonyl group having 6 to 14 carbon atoms substituted with an alkyloxy group having 1 to 6 carbon atoms, an alkyloxycarbonyl group having 1 to 6 carbon atoms ,
An aminocarbonyl group disubstituted with an alkyl group having 1 to 6 carbon atoms, an alkyl-carbonyl group having 1 to 6 carbon atoms substituted with an alkyloxy group having 1 to 6 carbon atoms,
C1-C20 alkyl-carbonylamino-C1-C6 alkyl-carbonyl group, C1-C6 alkyl-carbonyloxy-C1-C6
A compound having 1 to 6 alkyl-carbonyl groups or 1 to 6 alkyl-carbonyl groups substituted with 1 to 6 alkyl groups having 1 to 6 carbon atoms,
(4-2) R ² is an alkyl-carbonyl group having 1 to 6 carbon atoms, an alkyl-carbonyl group having 1 to 6 carbon atoms, which is substituted with 1 to 3 halogen atoms or / and amino groups,
An aryl-carbonyl group having 6 to 14 carbon atoms, an aryl-carbonyl group having 6 to 14 carbon atoms substituted with an alkyloxy group having 1 to 6 carbon atoms, an alkyloxycarbonyl group having 1 to 6 carbon atoms, An aminocarbonyl group disubstituted by an alkyl group having 1 to 6 carbon atoms, 1 carbon atom
C1 to C6 alkyl-carbonyl group substituted with C1 to C6 alkyloxy group, C1 to C20 alkyl-carbonylamino-C1 to C6 alkyl-carbonyl group, C1 1 to 6 alkyl-carbonyloxy-alkyl having 1 to 6 carbon atoms, or 1- or 2-substituted amino-alkyl having 1 to 6 carbon atoms. A compound which is a carbonyl group, (5-1) wherein R ² is a hydrogen atom, a methylcarbonyl group, an ethylcarbonyl group, an isopropylcarbonyl group, a trifluoromethylcarbonyl group, a phenylcarbonyl group, a 4-methoxyphenylcarbonyl group, a methoxycarbonyl group , T-butoxycarbonyl group, dimethylaminocarbonyl group, aminomethylcarbonyl group, Le propyl oxycarbonyl group,
A compound that is a methoxymethylcarbonyl group, an acetylaminomethylcarbonyl group, an acetoxymethylenecarbonyl group, a methylaminomethylenecarbonyl group, or a dimethylaminomethylenecarbonyl group, wherein (5-2) R ² is a methylcarbonyl group, an ethylcarbonyl group, Carbonyl group, trifluoromethylcarbonyl group, phenylcarbonyl group, 4-methoxyphenylcarbonyl group, methoxycarbonyl group, t-butoxycarbonyl group, dimethylaminocarbonyl group, aminomethylcarbonyl group, 2-methylpropyloxycarbonyl group, methoxy A methylcarbonyl group, an acetylaminomethylcarbonyl group, an acetoxymethylenecarbonyl group, a methylaminomethylenecarbonyl group, or a dimethylaminomethylenecarbonyl group Compound, (6-1) R ² is a hydrogen atom, a methyl group, an ethyl group, an isopropyl group, a methoxycarbonyl group, dimethylaminocarbonyl group, aminomethyl group, 2-
A compound which is a methylpropyloxycarbonyl group, a methoxymethylcarbonyl group, an acetylaminomethylcarbonyl group, an acetoxymethylenecarbonyl group, a methylaminomethylenecarbonyl group, or a dimethylaminomethylenecarbonyl group, wherein (6-2) R ² is a methylcarbonyl group , Ethylcarbonyl group, isopropylcarbonyl group,
Methoxycarbonyl group, dimethylaminocarbonyl group,
A compound which is an aminomethylcarbonyl group, a 2-methylpropyloxycarbonyl group, a methoxymethylcarbonyl group, an acetylaminomethylcarbonyl group, an acetoxymethylenecarbonyl group, a methylaminomethylenecarbonyl group, or a dimethylaminomethylenecarbonyl group;
-3) R ² is a hydrogen atom, a methylcarbonyl group, an aminomethylcarbonyl group, a 2-methylpropyloxycarbonyl group, a methoxymethylcarbonyl group, an acetylaminomethylcarbonyl group, an acetoxymethylenecarbonyl group,
A compound which is a methylaminomethylenecarbonyl group or a dimethylaminomethylenecarbonyl group (6-4) R ² is a methylcarbonyl group, an aminomethylcarbonyl group, a 2-methylpropyloxycarbonyl group,
A compound which is a methoxymethylcarbonyl group, an acetylaminomethylcarbonyl group, an acetoxymethylenecarbonyl group, a methylaminomethylenecarbonyl group or a dimethylaminomethylenecarbonyl group (7) wherein R ³ is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms Or a compound having an aryl group having 6 to 14 carbon atoms,
(8) R ³ is a hydrogen atom or a C 1 to 4 alkyl group having a carbon compound, (9) R ³ is a hydrogen atom or a methyl group, (10) R ⁴ is C 1 to 6 carbon atoms Alkyl group, 3- to 8-membered cycloalkyl group, alkyl group having 1 to 6 carbon atoms substituted by 1 to 3 halogen atoms, 1 to 6 carbon atoms substituted by alkoxy group having 1 to 6 carbon atoms A compound which is an alkyl group, an aminocarbonyl group, an aminocarbonyl group mono-substituted by an alkyl group having 1 to 6 carbon atoms, an aminocarbonyl group or a carboxyl group disubstituted by an alkyl group having 1 to 6 carbon atoms, (1
1) R ⁴ is methyl, ethyl, propyl, 1-methylethyl, 1-methyl-cyclopropyl, cyclobutyl, trifluoromethyl, methoxymethyl, methoxycarbonyl, aminocarbonyl, methylamino A compound which is a carbonyl group, a dimethylaminocarbonyl group or a carboxyl group, (12) an alkyl group having 1 to 4 carbon atoms for R ⁴ , an alkyl group having 1 to 4 carbon atoms substituted by 1 to 3 halogen atoms or an amino group A compound wherein R ⁴ is a methyl group, a 1-methylethyl group, a trifluoromethyl group or an aminocarbonyl group, (13-2) a compound wherein R ⁴ is a methyl group or a trifluoromethyl group Wherein (14-1) R ⁵ is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, and an alkyloxy group having 1 to 6 carbon atoms Si group, hydroxyl group, amino group, or
A compound which is an alkyl-carbonylamino group having 1 to 6 carbon atoms and substituted by 1 to 3 halogen atoms, (14-
2) R ⁵ is an alkyl group having 1 to 6 carbon atoms, an alkyloxy group having 1 to 6 carbon atoms, a hydroxyl group, an amino group, or
A compound which is an alkyl-carbonylamino group having 1 to 6 carbon atoms and which is substituted by 1 to 3 halogen atoms, (15-
1) R ⁵ is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms,
An alkyloxy group having 1 to 4 carbon atoms, a hydroxyl group, an amino group, or 1 carbon atom substituted by 1 to 3 halogen atoms;
To 4 alkyl - compound carbonyl amino group, (15-2) R ⁵ is a carbon number 1 to 4 alkyl groups having 1 to 4 carbon alkyl group carbon, a hydroxyl group, an amino group, or a halogen (16-1) a compound in which R ⁵ is a hydrogen atom, a methyl group, a methoxy group, a hydroxyl group, an amino group or a trifluoromethyl carbonyl; A compound which is an amino group, (16-2) a compound wherein R ⁵ is a methyl group, a methoxy group, a hydroxyl group, an amino group or a trifluoromethylcarbonylamino group, (17-1) R
^A compound wherein ⁵ is a hydrogen atom, a methyl group, a methoxy group, a hydroxyl group or an amino group; (17-2) a compound wherein R ⁵ is a methyl group, a methoxy group, a hydroxyl group or an amino group;
1) a compound wherein R ⁶ is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or a halogen atom, (18-2) a compound wherein R ⁶ is an alkyl group having 1 to 6 carbon atoms or a halogen atom, -1) a compound wherein R ⁶ is a hydrogen atom, a methyl group or a bromine atom, (19-2) a compound wherein R ⁶ is a methyl group or a bromine atom, and (20-1) a compound wherein R ⁶ is a hydrogen atom or a methyl group. A compound, (20-2) a compound wherein R ⁶ is a methyl group, (21) a compound wherein R ⁶ is a hydrogen atom, (2
2-1) a compound wherein R ⁷ is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a halogen atom, an alkyl group having 1 to 6 carbon atoms substituted with 1 to 3 halogen atoms or an amino group, (22) -2) a compound in which R ⁷ is an alkyl group having 1 to 6 carbon atoms, a halogen atom, an alkyl group having 1 to 6 carbon atoms and an amino group substituted by 1 to 3 halogen atoms, or (23-1) R ^A compound in which ⁷ is a hydrogen atom, a methyl group, a chlorine atom, a bromine atom, a trifluoromethyl group or an amino group, (23-2) R ⁷ is a methyl group, a chlorine atom, a bromine atom, a trifluoromethyl group or an amino group A compound, (24-1) a compound wherein R ⁷ is a hydrogen atom, a methyl group or a chlorine atom, (24-2) a compound wherein R ⁷ is a methyl group or a chlorine atom, (25-1) R ⁸ is a hydrogen atom Or alkyl having 1 to 6 carbon atoms Compound is, (25-
2) R ⁸ is an alkyl group having 1 to 6 carbon atoms compound (26-1) compounds wherein R ⁸ is hydrogen atom or a methyl group, (26-2) The compound wherein R ⁸ is methyl group, ( 2
7) compounds in which R ⁸ is a hydrogen atom, (28) compounds in which X ¹ is an oxygen atom or a sulfur atom, and (29) compounds in which X ¹ is a sulfur atom.

Further, R ¹ is selected from the above (1) to (3), R ² is selected from the above (4) to (6), R ³ is selected from the above (7) to (9), R ⁴ is selected from the above (10) to (13), and R ⁵ is selected from the above (14) to (1)
7), R ⁶ is selected from the above (18) to (21), R ⁷ is selected from the above (22) to (24),
R ⁸ is selected from the above (25) to (27), X ¹ is selected from the above (28) to (29), and arbitrarily selected and combined, for example, (1),
(4), (7), (10), (14), (18), (2)
2), a combination of (25) and (28), (2),
(5), (8), (11), (15), (19), (2)
3) and combinations of (26) and (28), (3),
(6), (9), (13), (17), (21), (2)
4), (27) and a combination of (29) are suitable.

The partial structural formula of the compound of the present invention has the general formula

[0026]

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A preferred compound when represented by the formula (3)
0) compounds in which R ²² is a hydrogen atom, (31) compounds in which R ²³ is a hydrogen atom, (32) compounds in which R ²⁴ is a hydrogen atom, and (33) compounds in which R ²⁵ is a hydrogen atom. The partial structural formula of the compound of the present invention has the general formula

[0028]

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A preferred compound when represented by the formula (3)
4) Compound R ²⁶ is a hydrogen atom, (35) a compound R ²⁷ is a hydrogen atom, (36) a compound R ²⁸ is a hydrogen atom, (37) a compound R ²⁹ is a hydrogen atom, the present invention The partial structural formula of the compound is represented by the general formula

[0030]

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A preferred compound when represented by the formula (3)
8) compounds in which R ³⁰ is a hydrogen atom, (39) compounds in which R ³¹ is a hydrogen atom, (40) compounds in which R ³² is a hydrogen atom, and (41) compounds in which R ³³ is a hydrogen atom. .

"Pharmacologically acceptable salt" means the compound (1) of the present invention, which can be converted into a salt, and the salt is preferable. Alkali metal salts such as potassium salts, lithium salts,
Metal salts such as alkaline earth metal salts such as calcium salts and magnesium salts, aluminum salts, iron salts, zinc salts, copper salts, nickel salts, and cobalt salts; inorganic salts such as ammonium salts, t-octylamine salts; Dibenzylamine salt, morpholine salt, glucosamine salt, phenylglycine alkyl ester salt, ethylenediamine salt, N-methylglucamine salt, guanidine salt, diethylamine salt, triethylamine salt, dicyclohexylamine salt, N, N′-dibenzylethylenediamine salt, Amine salts such as chloroprocaine salts, procaine salts, diethanolamine salts, N-benzyl-phenethylamine salts, piperazine salts, organic salts such as tetramethylammonium salts, tris (hydroxymethyl) aminomethane salts; hydrofluoric acid salts, hydrochloric acid Salt, hydrobromide, iodide water Inorganic acid salts such as hydrohalates, nitrates, perchlorates, sulfates, phosphates and the like; lower alkanes such as methanesulfonate, trifluoromethanesulfonate and ethanesulfonate Sulfates, benzenesulfonates, arylsulfonates such as p-toluenesulfonate, acetic acid, malic acid, fumarate, succinate, citrate, tartrate, oxalate, maleate Organic acid salts such as acid salts; and amino acid salts such as glycine salts, lysine salts, arginine salts, ornithine salts, glutamates and aspartates.

When the compound (1) of the present invention is left in the air, it may absorb water and may absorb adsorbed water or form hydrates. Included in the invention.

Further, the compound (1) of the present invention may absorb some other solvent and form a solvate, and such salts are also included in the present invention.

In the compound (1) of the present invention, R ¹ ,
Examples of combinations of R ^2, R ³ and X ^1, Table 1, R ^4, R ^5,
Table 2 shows examples of combinations of R ⁶ , R ⁷ and R ⁸ .

In Tables 1 and 2, Me is a methyl group, Et is an ethyl group, Pr is a propyl group, Bu is a butyl group, tBu is a t-butyl group, cPr is a cyclopropyl group, and cBu is cBu. Represents a cyclobutyl group, cHx represents a cyclohexyl group, Naph represents a naphthyl group, Ph represents a phenyl group, Pyr represents a pyridyl group, Fur represents a furyl group, Thi represents a thienyl group, and Mor represents a morpholino group.

In Table 1, (a) represents 3,4,5-tri
(CH_ThreeO) PhCH_TwoOCH_TwoC (= O) group, (b) is (CH_Three) C (= O) OCH (CH_Three)
C (= O) group, (c) is Thi-2- (CH_Two)_TwoNHCH_TwoC (= O) group, (d)
Is (CH_Three) C (= O) N (CH_Three) CH_TwoC (= O) group, (e) is CH_ThreeO (CH_Two)_TwoOC
(= O) NHCH_TwoC (= O) group, (f) is C_{1 Five}H₃₁C (= O) N (CH_Three) CH_TwoC (=
O) group, (g) is 2-Fur-C (= O) N (CH_Three) CH_TwoC (= O) group, (h)
Is 4-CH_Three-PhSO_TwoN (CH_Three) CH_TwoC (= O) group, (i) is 2-Thi-SO_TwoN
(CH_Three) CH_TwoC (= O) group, (j) is 3,4,5-tri-Me-PhC (= O) NHCH_Two
C (= O) group, (k) is (CH_Three)_TwoCHCH_TwoC (= O) NHCH_TwoC (= O) group,
(L) is MeO (CH_Two)_TwoOCH_TwoC (= O) NHCH_TwoC (= O) group, (m) is
HOC (= O) (CH_Two)_TwoC (= O) NHCH _TwoC (= O) group, (n) is MeO [(CH_Two)_Two
O]_FourCH_TwoC (= O) NHCH_TwoIt represents a C (= O) group.

[0038]

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[0039]

[Table 1] ――――――――――――――――――――――――――――――――――― No. R ¹ R ² R ³ X ¹ ― ―――――――――――――――――――――――――――――――――― 1 Ph HHS 2 2-Me-Ph HHS 3 4-Me-Ph HHS 4 4-Et-Ph HHS 5 4-Pr-Ph HHS 6 4- (CH ₃ ) ₂ CH-Ph HHS 7 4- (CH ₃ ) ₂ C (OH) -Ph HHS 8 4-tBu-Ph HHS 9 3-HO-Ph HHS 10 4-HO-Ph HHS 11 2-F-Ph HHS 12 4-F-Ph HHS 13 2-Cl-Ph HHS 14 4-Cl-Ph HHS 15 3-F ₃ C-Ph HHS 16 4-F ₃ C-Ph HHS 17 2-MeO-Ph HHS 18 4-MeO-Ph HHS 19 4-EtO-Ph HHS 20 4-BuO-Ph HHS 21 4-PhO-Ph HHS 22 4- (CH ₃ ) ₂ CHO-Ph HHS 23 4- (cHx) -Ph HHS 24 4-NC-Ph HHS 25 4-HOOC-Ph HHS 26 4-O ₂ N-Ph HHS 27 4-CH ₃ C (= O) -Ph HHS 28 4-NH ₂ C (= O) -Ph HHS 29 4-MeNHC (= O) -Ph HHS 30 4-EtNHC (= O) -Ph HHS 31 4- (CH ₃ ) ₂ NC (= O)- Ph HHS 32 4- (CH ₃ ) (CH ₃ O) NC (= O) HHS 33 4-EtOC (= O) -Ph HHS 34 4-MeOC (= O) -Ph HHS 35 4-CH ₃ C (= O) NH-Ph HHS 36 2,4-di-Me-Ph HHS 37 2,6-di-Me-Ph HHS 38 3,4-di-Me-Ph HHS 39 3,5-di-Me-Ph HHS 40 2,6-di-Et-Ph HHS 41 2,4-di-MeO-Ph HHS 42 2,5-di-MeO-Ph HHS 43 3,4-di-MeO-Ph HHS 44 3,5-di-MeO-Ph HHS 45 3,4-di- Cl-Ph HHS 46 3,5-di-F ₃ C-Ph HHS 47 2-MeO-5-Me-Ph HHS 48 3-Cl-4-F-Ph HHS 49 3-F-4-Me-Ph HHS 50 2,3,4-tri-F-Ph HHS 51 Naph-1- HHS 52 Pyr-2- HHS 53 Pyr-3- HHS 54 4-Me-Pyr-2- HHS 55 5-Me-Pyr-2- HHS 56 6-MeO-Pyr-2- HHS 57 6-MeO-Pyr-3- HHS 58 5-Cl-Pyr-2- HHS 59 6-Cl-Pyr-3- HHS 60 Me HHS 61 Et HHS 62 4- MeO-PhCH ₂ HHS 63 CH ₃ CH ₂ C (= O) HHS 64 C ₈ H ₁₇ C (= O) HHS 65 Naph-2-C (= O) HHS 66 Fur-1-C (= O) HHS 67 PhCH ₂ CH ₂ C (= O) HHS 68 2-Me-PhC (= O) HHS 69 4-Me-PhC (= O) HHS 70 4-MeO-PhC (= O) HHS 71 4-O ₂ N- PhC (= O) HHS 72 3-F ₃ C-PhC (= O) HHS 73 Ph (CH = CH) C (= O) HHS 74 4-MeO-PhC (= O) HHS 75 3,4-di- MeO-PhC (= O) HHS 76 4-Me-Ph H Me S 77 4-MeO-Ph H Me S 78 4-CH ₃ C (= O) -Ph H Me S 79 4-EtOC (= O)- Ph H Me S 80 4-NC-Ph H Me S 81 4-F ₃ C-Ph H Me S 82 6-MeO-Pyr-3- H Me S 83 4-Me-Ph H Pr S 84 4-MeO- Ph H Pr S 85 4-CH ₃ C (= O) -Ph H Pr S 86 4-EtOC (= O) -Ph H Pr S 87 4-NC-Ph H Pr S88 4-F ₃ C-Ph H Pr S 89 6-MeO-Pyr-3- H Pr S 90 4-Me-Ph H (CH ₃ ) ₂ CH S 91 4-MeO-Ph H (CH ₃ ) ₂ CH S 92 4-CH ₃ C (= O) -Ph H (CH ₃ ) ₂ CH S 93 4-EtOC (= O)- Ph H (CH ₃ ) ₂ CH S 94 4-NC-Ph H (CH ₃ ) ₂ CH S 95 4-F ₃ C-Ph H (CH ₃ ) ₂ CH S 96 6-MeO-Pyr-3- H ( CH ₃ ) ₂ CH S 97 4-Me-Ph H Ph S 98 4-MeO-Ph H Ph S 99 4-CH ₃ C (= O) -Ph H Ph S 100 4-EtOC (= O) -Ph H Ph S 101 4-NC-Ph H Ph S 102 4-F ₃ C-Ph H Ph S 103 6-MeO-Pyr-3- H Ph S 104 Ph Me HS 105 4-MeO-Ph Me HS 106 4-HO -Ph Me HS 107 4-CH ₃ C (= O) -Ph Me HS 108 6-MeO-Pyr-3- Me HS 109 Ph Et HS 110 4-MeO-Ph Et HS 111 4-HO-Ph Et HS 112 4-CH ₃ C (= O) -Ph Et HS 113 6-MeO-Pyr-3- Et HS 114 Ph PhCH ₂ HS 115 4-MeO-Ph PhCH ₂ HS 116 4-HO-Ph PhCH ₂ HS 117 4- CH ₃ C (= O) -Ph PhCH ₂ HS 118 6-MeO-Pyr-3- PhCH ₂ HS 119 Ph Ph (CH ₂ ) ₂ HS 120 4-MeO-Ph Ph (CH ₂ ) ₂ HS 121 4-HO -Ph Ph (CH ₂ ) ₂ HS 122 4-CH ₃ C (= O) -Ph Ph (CH ₂ ) ₂ HS 123 6-MeO-Pyr-3- Ph (CH ₂ ) ₂ HS 124 Ph CH ₃ C ( = O) HS 125 4-MeO-Ph CH ₃ C (= O) HS 126 4-HO-Ph CH ₃ C (= O) HS 127 4-CH ₃ C (= O) -Ph CH ₃ C (= O ) HS 128 6-MeO-Pyr-3- CH ₃ C (= O) HS 129 Ph CF ₃ C (= O) HS 130 4-MeO-Ph CF ₃ C (= O) HS 131 4-HO-Ph CF ₃ C (= O) HS 132 6-MeO-Pyr-3- CF ₃ C (= O) HS 133 Ph tBuOC (= O) HS 134 4-MeO-Ph tBuOC (= O) HS 135 4-HO-Ph tBuOC (= O) HS 136 4-CH ₃ C (= O) -Ph tBuOC (= O) HS 137 6-MeO-Pyr-3- tBuOC (= O) HS 138 Ph PhC (= O) HS 139 4-MeO-Ph PhC (= O) HS 140 4-HO-Ph PhC (= O) HS 141 4-CH ₃ C (= O) -Ph PhC (= O) HS 142 6-MeO-Pyr-3- PhC (= O) HS 143 6-MeO-Pyr-3- (CH ₃ ) ₂ CHC (= O) HS 144 6-MeO-Pyr-3- CH ₃ CH ₂ C (= O) HS 145 6-MeO-Pyr-3- CH ₃ OC (= O) HS 146 6-MeO-Pyr-3- (CH ₃ ) ₂ NC (= O) HS 147 4-Me-Ph CH ₃ C (= O) HS 148 4-MeO-Ph 4-MeO-PhC (= O) HS 149 4-CF ₃ -Ph CH ₃ C (= O) HS 150 Ph HHO 151 2-Me-Ph HHO 152 4- Me-Ph HHO 153 4-Et-Ph HHO 154 4-Pr-Ph HHO 155 4- (CH ₃ ) ₂ CH-Ph HHO 156 4- (CH ₃ ) ₂ C (OH) -Ph HHO 157 4-tBu- Ph HHO 158 3-HO-Ph HHO 159 4-HO-Ph HHO 160 2-F-Ph HHO 161 4-F-Ph HHO 162 2-Cl-Ph HHO 163 4-Cl-Ph HHO 164 3-F ₃ C -Ph HHO 165 4-F ₃ C-Ph HHO 166 2-MeO-Ph HHO 167 4-MeO-Ph HHO 168 4-EtO-Ph HHO 169 4-BuO-Ph HHO 170 4-PhO-Ph HHO 171 4- (CH ₃ ) ₂ CHO-Ph HHO 172 4- (cHx) -Ph HHO 173 4-NC-Ph HHO 174 4-HOOC-Ph HHO 175 4 -O ₂ N-Ph HHO 176 4-CH ₃ C (= O) -Ph HHO 177 4-NH ₂ C (= O) -Ph HHO 178 4-MeNHC (= O) -Ph HHO 179 4-EtNHC (= O) -Ph HHO 180 4- (CH ₃ ) ₂ NC (= O) -Ph HHO 181 4- (CH ₃ ) (CH ₃ O) NC (= O) HHO 182 4-EtOC (= O) -Ph HHO 183 4-MeOC (= O) -Ph HHO 184 4-CH ₃ C (= O) NH-Ph HHO 185 2,4-di-Me-Ph HHO 186 2,6-di-Me-Ph HHO 187 3, 4-di-Me-Ph HHO 188 3,5-di-Me-Ph HHO 189 2,6-di-Et-Ph HHO 190 2,4-di-MeO-Ph HHO 191 2,5-di-MeO- Ph HHO 192 3,4-di-MeO-Ph HHO 193 3,5-di-MeO-Ph HHO 194 3,4-di-Cl-Ph HHO 195 3,5-di-F ₃ C-Ph HHO 196 2 -MeO-5-Me-Ph HHO 197 3-Cl-4-F-Ph HHO 198 3-F-4-Me-Ph HHO 199 2,3,4-tri-F-Ph HHO 200 Naph-1- HHO 201 Pyr-2-HHO 202 Pyr-3- HHO 203 4-Me-Pyr-2-HHO 204 5-Me-Pyr-2-HHO 205 6-MeO-Pyr-2-HHO 206 6-MeO-Pyr-3 -HHO 207 5-Cl-Pyr-2-HHO 208 6-Cl-Pyr-3- HHO 209 Me HHO 210 Et HHO 211 4-MeO-PhCH ₂ HHO 212 CH ₃ CH ₂ C (= O) HHO 213 C ₈ H ₁₇ C (= O) HHO 214 Naph-2-C (= O) HHO 215 Fur-1-C (= O) HHO 216 PhCH ₂ CH ₂ C (= O) HHO 217 2-Me-PhC (= O ) HHO 218 4-Me-PhC (= O) HHO 219 4-MeO-PhC (= O) HHO 220 4-O ₂ N-PhC (= O) HHO 221 3-F ₃ C-PhC (= O) HHO 222 Ph (CH = CH) C (= O) HHO 223 4-MeO-PhC (= O) HHO 224 3,4-di-MeO-PhC (= O) HHO 225 4-Me-Ph H Me O 226 4 -MeO-Ph H Me O 227 4-CH ₃ C (= O) -Ph H Me O 228 4-EtOC (= O) -Ph H Me O 229 4-NC-Ph H Me O 230 4-F ₃ C -Ph H Me O 231 6-MeO-Pyr-3- H Me O 232 4-Me-Ph H Pr O 233 4-MeO-Ph H Pr O 234 4-CH ₃ C (= O) -Ph H Pr O 235 4-EtOC (= O) -Ph H Pr O 236 4-NC-Ph H Pr O 237 4-F ₃ C-Ph H Pr O 238 6-MeO-Pyr-3- H Pr O 239 4-Me- Ph H (CH ₃ ) ₂ CH O 240 4-MeO-Ph H (CH ₃ ) ₂ CH O 241 4-CH ₃ C (= O) -Ph H (CH ₃ ) ₂ CH O 242 4-EtOC (= O ) -Ph H (CH ₃ ) ₂ CH O 243 4-NC-Ph H (CH ₃ ) ₂ CH O 244 4-F ₃ C-Ph H (CH ₃ ) ₂ CH O 245 6-MeO-Pyr-3- H (CH ₃ ) ₂ CH O 246 4-Me-Ph H Ph O 247 4-MeO-Ph H Ph O 248 4-CH ₃ C (= O) -Ph H Ph O 249 4-EtOC (= O)- Ph H Ph O 250 4-NC-Ph H Ph O 251 4-F ₃ C-Ph H Ph O 252 6-MeO-Pyr-3- H Ph O 253 Ph Me HO 254 4-MeO-Ph Me HO 255 4 -HO-Ph Me HO 256 4-CH ₃ C (= O) -Ph Me HO 257 6-MeO-Pyr-3- Me HO 258 Ph Et HO 259 4-MeO-Ph Et HO 260 4-HO-Ph Et HO 261 4-CH ₃ C (= O) -Ph Et HO 262 6-MeO-Pyr-3- Et HO 263 Ph PhCH ₂ HO 264 4-MeO-Ph PhCH ₂ HO 265 4-HO-Ph PhCH ₂ HO 266 4-CH ₃ C (= O) -Ph PhCH ₂ HO 267 6-MeO-Pyr-3- PhCH ₂ HO 268 Ph Ph (CH ₂ ) ₂ HO 269 4-MeO -Ph Ph (CH ₂ ) ₂ HO 270 4-HO-Ph Ph (CH ₂ ) ₂ HO 271 4-CH ₃ C (= O) -Ph Ph (CH ₂ ) ₂ HO 272 6-MeO-Pyr-3- Ph (CH ₂ ) ₂ HO 273 Ph CH ₃ C (= O) HO 274 4-MeO-Ph CH ₃ C (= O) HO 275 4-HO-Ph CH ₃ C (= O) HO 276 4-CH ₃ C (= O) -Ph CH ₃ C (= O) HO 277 6-MeO-Pyr-3- CH ₃ C (= O) HO 278 Ph CF ₃ C (= O) HO 279 4-MeO-Ph CF ₃ C (= O) HO 280 4-HO-Ph CF ₃ C (= O) HO 281 6-MeO-Pyr-3- CF ₃ C (= O) HO 282 Ph tBuOC (= O) HO 283 4-MeO- Ph tBuOC (= O) HO 284 4-HO-Ph tBuOC (= O) HO 285 4-CH ₃ C (= O) -Ph tBuOC (= O) HO 286 6-MeO-Pyr-3- tBuOC (= O ) HO 287 Ph PhC (= O) HO 288 4-MeO-Ph PhC (= O) HO 289 4-HO-Ph PhC (= O) HO 290 4-CH ₃ C (= O) -Ph PhC (= O ) HO 291 6-MeO-Pyr-3- PhC (= O) HO 292 6-MeO-Pyr-3- (CH ₃ ) ₂ CHC (= O) HO 293 6-MeO-Pyr-3- CH ₃ CH ₂ C (= O) HO 294 6-MeO-Pyr-3- CH ₃ OC (= O) HO 295 6-MeO-Pyr-3- (CH ₃ ) ₂ NC (= O) HO 296 4-Me-Ph CH ₃ C (= O) HO 297 4-MeO-Ph 4-MeO-PhC (= O) HO 298 4-CF ₃ -Ph CH ₃ C (= O) HO 299 Ph HH NH 300 2-Me-Ph HH NH 301 4-Me-Ph HH NH 302 4-Et-Ph HH NH 303 4-Pr-Ph HH NH 304 4- (CH ₃ ) ₂ CH-Ph HH NH 305 4- (CH ₃ ) ₂ C (OH) -Ph HH NH 306 4- tBu-Ph HH NH 307 3-HO-Ph HH NH 308 4-HO-Ph HH NH 309 2-F-Ph HH NH 310 4-F-Ph HH NH 311 2-Cl-Ph HH NH 312 4-Cl- Ph HH NH 313 3-F ₃ C-Ph HH NH 314 4-F ₃ C-Ph HH NH 315 2-MeO-Ph HH NH 316 4-MeO-Ph HH NH 317 4-EtO-Ph HH NH 318 4- BuO-Ph HH NH 319 4-PhO-Ph HH NH 320 4- (CH ₃ ) ₂ CHO-Ph HH NH 321 4- (cHx) -Ph HH NH 322 4-NC-Ph HH NH 323 4-HOOC-Ph HH NH 324 4-O ₂ N-Ph HH NH 325 4-CH ₃ C (= O) -Ph HH NH 326 4-NH ₂ C (= O) -Ph HH NH 327 4-MeNHC (= O) -Ph HH NH 328 4-EtNHC (= O) -Ph HH NH 329 4- (CH ₃ ) ₂ NC (= O) -Ph HH NH 330 4- (CH ₃ ) (CH ₃ O) NC (= O) HH NH 331 4-EtOC (= O) -Ph HH NH 332 4-MeOC (= O) -Ph HH NH 333 4-CH ₃ C (= O) NH-Ph HH NH 334 2,4-di-Me-Ph HH NH 335 2,6-di-Me-Ph HH NH 336 3,4-di-Me-Ph HH NH 337 3,3-di-Me-Ph HH NH 338 2,6-di-Et-Ph HH NH 339 2,4-di-MeO-Ph HH NH 340 2,5-di-MeO-Ph HH NH 341 3,4-di-MeO-Ph HH NH 342 3,5-di-MeO-Ph HH NH 343 3, 4-di-Cl-Ph HH NH 344 3,5-di-F ₃ C-Ph HH NH 345 2-MeO-5-Me-Ph HH NH 346 3-Cl-4-F-Ph HH NH 347 3-F-4-Me-Ph HH NH 348 2,3,4-tri-F-Ph HH NH 349 Naph-1- HH NH 350 Pyr-2- HH NH 351 Pyr-3- HH NH 352 4-Me-Pyr-2-HH NH 353 5-Me-Pyr-2-HH NH 354 6-MeO-Pyr-2-HH NH 355 6-MeO-Pyr-3 -HH NH 356 5-Cl-Pyr-2- HH NH 357 6-Cl-Pyr-3- HH NH 358 Me HH NH 359 Et HH NH 360 4-MeO-PhCH ₂ HH NH 361 CH ₃ CH ₂ C (= O) HH NH 362 C ₈ H ₁₇ C (= O) HH NH 363 Naph-2-C (= O) HH NH 364 Fur-1-C (= O) HH NH 365 PhCH ₂ CH ₂ C (= O) HH NH 366 2-Me-PhC (= O) HH NH 367 4-Me-PhC (= O) HH NH 368 4-MeO-PhC (= O) HH NH 369 4-O ₂ N-PhC (= O) HH NH 370 3-F ₃ C-PhC (= O) HH NH 371 Ph (CH = CH) C (= O) HH NH 372 4-MeO-PhC (= O) HH NH 373 3,4-di-MeO -PhC (= O) HH NH 374 4-Me-Ph H Me NH 375 4-MeO-Ph H Me NH 376 4-CH ₃ C (= O) -Ph H Me NH 377 4-EtOC (= O)- Ph H Me NH 378 4-NC-Ph H Me NH 379 4-F ₃ C-Ph H Me NH 380 6-MeO-Pyr-3- H Me NH 381 4-Me-Ph H Pr NH 382 4-MeO- Ph H Pr NH 383 4-CH ₃ C (= O) -Ph H Pr NH 384 4-EtOC (= O) -Ph H Pr NH 385 4-NC-Ph H Pr NH 386 4-F ₃ C-Ph H Pr NH 387 6-MeO-Pyr-3- H Pr NH 388 4-Me-Ph H (CH ₃ ) ₂ CH NH 389 4-MeO-Ph H ( CH ₃ ) ₂ CH NH 390 4-CH ₃ C (= O) -Ph H (CH ₃ ) ₂ CH NH 391 4-EtOC (= O) -Ph H (CH ₃ ) ₂ CH NH 392 4-NC-Ph H (CH ₃ ) ₂ CH NH 393 4-F ₃ C-Ph H (CH ₃ ) ₂ CH NH 394 6-MeO-Pyr-3- H (CH ₃ ) ₂ CH NH 395 4-Me-Ph H Ph NH 396 4-MeO-Ph H Ph NH 397 4-CH ₃ C (= O) -Ph H Ph NH 398 4-EtOC (= O) -Ph H Ph NH 399 4-NC-Ph H Ph NH 400 4-F ₃ C-Ph H Ph NH 401 6-MeO-Pyr-3- H Ph NH 402 Ph Me H NH 403 4-MeO-Ph Me H NH 404 4-HO-Ph Me H NH 405 4-CH ₃ C (= O) -Ph Me H NH 406 6-MeO-Pyr-3- Me H NH 407 Ph Et H NH 408 4-MeO-Ph Et H NH 409 4-HO-Ph Et H NH 410 4-CH ₃ C (= O) -Ph Et H NH 411 6-MeO-Pyr-3- Et H NH 412 Ph PhCH ₂ H NH 413 4-MeO-Ph PhCH ₂ H NH 414 4-HO-Ph PhCH ₂ H NH 415 4-CH ₃ C (= O) -Ph PhCH ₂ H NH 416 6-MeO-Pyr-3- PhCH ₂ H NH 417 Ph Ph (CH ₂ ) ₂ H NH 418 4-MeO-Ph Ph (CH ₂ ) ₂ H NH 419 4 -HO-Ph Ph (CH ₂ ) ₂ H NH 420 4-CH ₃ C (= O) -Ph Ph (CH ₂ ) ₂ H NH 421 6-MeO-Pyr-3- Ph (CH ₂ ) ₂ H NH 422 Ph CH ₃ C (= O) H NH 423 4-MeO-Ph CH ₃ C (= O) H NH 424 4-HO-Ph CH ₃ C (= O) H NH 425 4-CH ₃ C (= O) -Ph CH ₃ C (= O) H NH 426 6-MeO-Pyr-3- CH ₃ C (= O) H NH 427 Ph CF ₃ C (= O) H NH 428 4-MeO-Ph CF ₃ C (= O) H NH 429 4-HO-Ph CF ₃ C (= O) H NH 430 6-MeO-Pyr-3- CF ₃ C (= O) H NH 431 Ph tBuOC (= O) H NH 432 4-MeO-Ph tBuOC (= O) H NH 433 4-HO-Ph tBuOC (= O) H NH 434 4-CH ₃ C (= O) -Ph tBuOC (= O) H NH 435 6-MeO-Pyr-3- tBuOC (= O) H NH 436 Ph PhC (= O) H NH 437 4-MeO-Ph PhC (= O) H NH 438 4-HO-Ph PhC (= O) H NH 439 4-CH ₃ C (= O) -Ph PhC (= O) H NH 440 6-MeO-Pyr-3- PhC (= O) H NH 441 6-MeO-Pyr-3- (CH ₃ ) ₂ CHC (= O) H NH 442 6-MeO-Pyr-3- CH ₃ CH ₂ C (= O) H NH 443 6-MeO-Pyr-3- CH ₃ OC (= O) H NH 444 6-MeO-Pyr-3- (CH ₃ ) ₂ NC (= O) H NH 445 4-Me-Ph CH ₃ C (= O) H NH 446 4-MeO-Ph 4-MeO-PhC (= O) H NH 447 4-CF ₃ -Ph CH ₃ C (= O) H NH 448 6-MeO-Pyr-3- PhCH ₂ OCH ₂ C (= O) HS 449 6-MeO -Pyr-3- (CH ₃ ) ₂ CHCH ₂ OCH ₂ C (= O) HS 450 6-MeO-Pyr-3- (CH ₃ ) ₂ CHOCH ₂ C (= O) HS 451 6-MeO-Pyr-3 -(a) HS 452 6-MeO-Pyr-3- PhOCH ₂ C (= O) HS 453 6-MeO-Pyr-3- Thi-2-O-CH ₂ C (= O) HS 454 6-MeO- Pyr-3- (b) HS 455 6-MeO-Pyr-3- (c) HS 456 6-MeO-Pyr-3- Mor (CH ₂ ) ₂ NHCH ₂ C (= O) HS 457 6-MeO-Pyr -3- (d) HS 458 6-MeO-Pyr-3- (CH O) (CH ₃ ) NCH ₂ C (= O) HS 459 6-MeO-Pyr-3- CH ₃ NHCH ₂ C (= O) HS 460 6-MeO-Pyr-3- PhCH ₂ NHCH ₂ C (= O ) HS 461 6-MeO-Pyr-3- PhCH ₂ N (CH ₃ ) CH ₂ C (= O) HS 462 6-MeO-Pyr-3- (e) HS 463 6-MeO-Pyr-3- (f ) HS 464 6-MeO-Pyr-3- PhC (= O) N (CH ₃ ) CH ₂ C (= O) HS 465 6-MeO-Pyr-3- (g) HS 466 6-MeO-Pyr-3 -C ₃ H ₇ SO ₂ N (CH ₃ ) CH ₂ C (= O) HS 467 6-MeO-Pyr-3- (h) HS 468 6-MeO-Pyr-3- (i) HS 469 6-MeO -Pyr-3-C ₁₅ H ₃₁ OCH ₂ C (= O) HS 470 6-MeO-Pyr-3-Pyr-3-CH ₂ OCH ₂ C (= O) HS 471 6-MeO-Pyr-3- ( CH ₃ ) ₂ NC ₂ H ₄ OCH ₂ C (= O) HS 472 6-MeO-Pyr-3- HOC (= O) C ₂ H ₄ OCH ₂ C (= O) HS 473 6-MeO-Pyr-3 -CH ₃ OCH (CH ₃ ) C (= O) HS 474 6-MeO-Pyr-3- CH ₃ OC (CH ₃ ) ₂ C (= O) HS 475 6-MeO-Pyr-3-NH ₂ C ( = O) OCH ₂ C (= O) HS 476 6-MeO-Pyr-3-NH ₂ C (= O) C (= O) HS 477 6-MeO-Pyr-3-Tiaz-2-CH ₂ OCH ₂ C (= O) HS 478 6-MeO-Pyr-3- (j) HS 479 6-MeO-Pyr-3- (k) HS 480 6-MeO-Pyr-3- (l) HS 481 6-MeO- Pyr-3- (m) HS 482 6-MeO-Pyr-3- (n) HS 483 6-MeO-Pyr-3- (CHO) (CH ₃ ) NCH ₂ C (= O) HS 484 6-MeO- _{Pyr-3- C 15 H 31 C} (= O) NHCH 2 C (= O) HS 485 6-MeO-Pyr-3- HO (CH 2) 2 NHCH ₂ C (= O) HS 486 4-MeO-Ph-3- PhCH ₂ OCH ₂ C (= O) HS 487 4-MeO-Ph-3- (CH ₃ ) ₂ CHCH ₂ OCH ₂ C (= O) HS 488 4-MeO-Ph-3- (CH ₃ ) ₂ CHOCH ₂ C (= O) HS 489 4-MeO-Ph-3- (a) HS 490 4-MeO-Ph-3- PhOCH ₂ C (= O ) HS 491 4-MeO-Ph-3- Thi-2-O-CH ₂ C (= O) HS 492 4-MeO-Ph-3- (b) HS 493 4-MeO-Ph-3- (c) HS 494 4-MeO-Ph-3- Mor (CH ₂ ) ₂ NHCH ₂ C (= O) HS 495 4-MeO-Ph-3- (d) HS 496 4-MeO-Ph-3- (CHO) ( CH ₃ ) NCH ₂ C (= O) HS 497 4-MeO-Ph-3- CH ₃ NHCH ₂ C (= O) HS 498 4-MeO-Ph-3- PhCH ₂ NHCH ₂ C (= O) HS 499 4-MeO-Ph-3- PhCH ₂ N (CH ₃ ) CH ₂ C (= O) HS 500 4-MeO-Ph-3- (e) HS 501 4-MeO-Ph-3- (f) HS 502 4-MeO-Ph-3- PhC (= O) N (CH ₃ ) CH ₂ C (= O) HS 503 4-MeO-Ph-3- (g) HS 504 4-MeO-Ph-3- C ₃ H ₇ SO ₂ N (CH ₃ ) CH ₂ C (= O) HS 505 4-MeO-Ph-3- (h) HS 506 4-MeO-Ph-3- (i) HS 507 4-MeO-Ph- 3-C ₁₅ H ₃₁ OCH ₂ C (= O) HS 508 4-MeO-Ph-3-Pyr-3-CH ₂ OCH ₂ C (= O) HS 509 4-MeO-Ph-3- (CH ₃ ) ₂ NC ₂ H ₄ OCH ₂ C (= O) HS 510 4-MeO-Ph-3- HOC (= O) C ₂ H ₄ OCH ₂ C (= O) HS 511 4-MeO-Ph-3- CH ₃ OCH (CH ₃ ) C (= O) HS 512 4-MeO-Ph-3- CH ₃ OC (CH ₃ ) ₂ C (= O) HS 513 4-MeO-Ph-3- NH ₂ C (= O) OCH ₂ C (= O) HS 514 4-MeO-Ph-3- NH ₂ C (= O) C (= O) HS 515 4-MeO-Ph-3- Tiaz-2- CH ₂ OCH ₂ C (= O) HS 516 4-MeO-Ph-3- (j) HS 517 4-MeO-Ph-3- (k) HS 518 4-MeO-Ph-3- (l) HS 519 4-MeO-Ph-3- (m) HS 520 4-MeO-Ph-3- (n) HS 521 4-MeO-Ph-3- (CHO) (CH ₃ ) NCH ₂ C (= O) HS 522 4-MeO-Ph-3-C ₁₅ H ₃₁ C (= O) NHCH ₂ C (= O) HS 523 4-MeO-Ph-3- HO (CH ₂ ) ₂ NHCH ₂ C (= O) HS 524 6 -Me-Pyr-3- PhCH ₂ OCH ₂ C (= O) HS 525 6-Me-Pyr-3- (CH ₃ ) ₂ CHCH ₂ OCH ₂ C (= O) HS 526 6-Me-Pyr-3- (CH ₃ ) ₂ CHOCH ₂ C (= O) HS 527 6-Me-Pyr-3- (a) HS 528 6-Me-Pyr-3- PhOCH ₂ C (= O) HS 529 6-Me-Pyr- 3- Thi-2-O-CH ₂ C (= O) HS 530 6-Me-Pyr-3- (b) HS 531 6-Me-Pyr-3- (c) HS 532 6-Me-Pyr-3 -Mor (CH ₂ ) ₂ NHCH ₂ C (= O) HS 533 6-Me-Pyr-3- (d) HS 534 6-Me-Pyr-3- (CHO) (CH ₃ ) NCH ₂ C (= O ) HS 535 6-Me-Pyr-3- CH ₃ NHCH ₂ C (= O) HS 536 6-Me-Pyr-3- PhCH ₂ NHCH ₂ C (= O) HS 537 6-Me-Pyr-3- PhCH ₂ N (CH ₃ ) CH ₂ C (= O) HS 538 6-Me-Pyr-3- (e) HS 539 6-Me-Pyr-3- (f) HS 540 6-Me-Pyr-3- PhC (= O) N (CH ₃ ) CH ₂ C (= O) HS 541 6-Me-Pyr-3- (g) HS 542 6-Me-Pyr-3- C ₃ H ₇ SO ₂ N (C H ₃ ) CH ₂ C (= O) HS 543 6-Me-Pyr-3- (h) HS 544 6-Me-Pyr-3- (i) HS 545 6-Me-Pyr-3- C ₁₅ H ₃₁ OCH ₂ C (= O) HS 546 6-Me-Pyr-3- Pyr-3-CH ₂ OCH ₂ C (= O) HS 547 6-Me-Pyr-3- (CH ₃ ) ₂ NC ₂ H ₄ OCH ₂ C (= O) HS 548 6-Me-Pyr-3- HOC (= O) C ₂ H ₄ OCH ₂ C (= O) HS 549 6-Me-Pyr-3- CH ₃ OCH (CH ₃ ) C (= O) HS 550 6-Me-Pyr-3- CH ₃ OC (CH ₃ ) ₂ C (= O) HS 551 6-Me-Pyr-3-NH ₂ C (= O) OCH ₂ C (= O ) HS 552 6-Me-Pyr-3- NH ₂ C (= O) C (= O) HS 553 6-Me-Pyr-3- Tiaz-2-CH ₂ OCH ₂ C (= O) HS 554 6- Me-Pyr-3- (j) HS 555 6-Me-Pyr-3- (k) HS 556 6-Me-Pyr-3- (l) HS 557 6-Me-Pyr-3- (m) HS 558 6-Me-Pyr-3- (n) HS 559 6-Me-Pyr-3- (CHO) (CH ₃ ) NCH ₂ C (= O) HS 560 6-Me-Pyr-3- C ₁₅ H ₃₁ C (= O) NHCH ₂ C (= O) HS 561 6-Me-Pyr-3-HO (CH ₂ ) ₂ NHCH ₂ C (= O) HS 562 4-Me-Ph-3- PhCH ₂ OCH ₂ C ( = O) HS (568) 563 4-Me-Ph-3- (CH ₃ ) ₂ CHCH ₂ OCH ₂ C (= O) HS (567) 564 4-Me-Ph-3- (CH ₃ ) ₂ CHOCH ₂ C (= O) HS (566) 565 4-Me-Ph-3- (a) HS 566 4-Me-Ph-3- PhOCH ₂ C (= O) HS (569) 567 4-Me-Ph-3 -Thi-2-O-CH ₂ C (= O) HS (571) 568 4-Me-Ph-3- (b) HS 569 4-Me-Ph-3- (c) HS 570 4-Me-Ph -3- Mor (C H ₂ ) ₂ NHCH ₂ C (= O) HS (577) 571 4-Me-Ph-3- (d) HS 572 4-Me-Ph-3- (CHO) (CH ₃ ) NCH ₂ C (= O ) HS (586) 573 4-Me-Ph-3- CH ₃ NHCH ₂ C (= O) HS (579) 574 4-Me-Ph-3- PhCH ₂ NHCH ₂ C (= O) HS (573) 575 4-Me-Ph-3- PhCH ₂ N (CH ₃ ) CH ₂ C (= O) HS (574) 576 4-Me-Ph-3- (e) HS 577 4-Me-Ph-3- (f ) HS 578 4-Me-Ph-3- PhC (= O) N (CH ₃ ) CH ₂ C (= O) HS (583) 579 4-Me-Ph-3- (g) HS 580 4-Me- Ph-3- C ₃ H ₇ SO ₂ N (CH ₃ ) CH ₂ C (= O) HS (582) 581 4-Me-Ph-3- (h) HS 582 4-Me-Ph-3- (i ) HS 583 4-Me-Ph-3-C ₁₅ H ₃₁ OCH ₂ C (= O) HS 584 4-Me-Ph-3-Pyr-3-CH ₂ OCH ₂ C (= O) HS 585 4-Me -Ph-3- (CH ₃ ) ₂ NC ₂ H ₄ OCH ₂ C (= O) HS 586 4-Me-Ph-3- HOC (= O) C ₂ H ₄ OCH ₂ C (= O) HS 587 4 -Me-Ph-3- CH ₃ OCH (CH ₃ ) C (= O) HS 588 4-Me-Ph-3- CH ₃ OC (CH ₃ ) ₂ C (= O) HS 589 4-Me-Ph- 3-NH ₂ C (= O) OCH ₂ C (= O) HS 590 4-Me-Ph-3- NH ₂ C (= O) C (= O) HS 591 4-Me-Ph-3- Tiaz- 2-CH ₂ OCH ₂ C (= O) HS 592 4-Me-Ph-3- (j) HS 593 4-Me-Ph-3- (k) HS 594 4-Me-Ph-3- (l) HS 595 4-Me-Ph-3- (m) HS 596 4-Me-Ph-3- (n) HS 597 4-Me-Ph-3- (CHO) (CH ₃ ) NCH ₂ C (= O) HS 598 4-Me-Ph-3- C ₁₅ H ₃₁ C (= O) NH CH ₂ C (= O) HS 599 4-Me-Ph-3- HO (CH ₂ ) ₂ NHCH ₂ C (= O) HS ------------------- ----------------------------------------- In Table 1 above, the preferred one is 1, 2, 3, 4,
5, 6, 7, 8, 9, 10, 14, 16, 17, 18,
19, 22, 24, 26, 27, 28, 29, 31, 3
3, 34, 35, 36, 38, 39, 41, 43, 4,
4, 45, 46, 49, 50, 56, 57, 59, 7
0, 71, 76, 77, 78, 81, 82, 105, 1
25, 127, 128, 130, 131, 137, 13
9,143,144,145,146,147,14
8, 448, 449, 450, 451, 452, 45
3, 454, 455, 456, 457, 458, 45
9, 460, 461, 462, 463, 464, 46
5, 466, 467, 468, 469, 470, 47
1,472,473,474,475,476,47
7, 478, 479, 480, 481, 482, 48
3, 484 and 485, and more preferred are
3, 16, 18, 27, 29, 56, 57, 59, 12
8, 143, 144, 145, 146, 147, 44
8, 449, 450, 451, 452, 453, 45
4, 455, 456, 457, 458, 459, 46
0, 461, 462, 463, 464, 465, 46
6, 467, 468, 469, 470, 471, 47
2,473,474,475,476,477,47
8, 479, 480, 481, 482, 483, 484
And 485.

[0040]

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[0041]

[Table 2] ---------------------------------------------- ^{--------------- No. R 4 R 5 R 6} R 7 R 8 ----------------------- -------------------------------------- 1a HHHHH 2a Me HHHH 3a Me HH Me H 4a Me HH Br H 5a Me HH Cl H 6a Me HHF ₃ CH 7a Me HH NH ₂ C (= O) H 8a Me HHO ₂ NH 9a Me HH Ph H 10a Me H Me HH 11a Me H Me H Me 12a Me Me HHH 13a Me MeO HHH 14a Me HO HHH 15a Me HO Br HH 16a Me H ₂ NHHH 17a Me H ₂ N Br HH 18a Me PhCH ₂ C (= O) HHH 19a Me CF ₃ C (= O) NH HHH 20a Et HHHH 21a 1 -Me-1-Et HHHH 22a 1-Me-1-Et HH Me H 23a Pr HHHH 24a cBu HHHH 25a 1-Me-cPr HHHH 26a Ph HHHH 27a MeNHC (= O) HHHH 28a Me ₂ NC (= O) HHHH 29a NH ₂ C (= O) HHHH 30a F ₃ CHHHH 31a F ₃ CHH Me H 32a F ₃ CHH Cl H 33a HOOC HHHH 34a MeOCH ₂ HHHH 35a MeOC (= O) HHHH 36a MeOC (= O) HH Me H 37a Me HHH ₂ NH 38a (CH ₃ ) ₂ CH HH Me H 39a NH ₂ C (= O) HH Me H -------------------------- ---------------------------------- In Table 2 above, preferred ones are 1a, 2a, 3a,
4a, 5a, 6a, 10a, 11a, 12a, 13a,
14a, 15a, 16a, 17a, 19a, 20a, 2
1a, 22a, 23a, 24a, 25a, 27a, 28
a, 29a, 30a, 31a, 32a, 33a, 34
a, 35a, 37a, 38a and 39a, more preferably 2a, 3a, 5a, 10a, 12a, 1a
3a, 14a, 16a, 21a, 22a, 30a, 31
a and 32a.

[0042]

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[0043]

[Table 3] ---------------------------------------------- ------------------- No. R ⁴ R ⁵ R ⁸ R ²² R ²³ R ²⁴ R ²⁵ --------------- -------------------------------------------------- 1b HHHHHHH 2b Me HHHHHH 3b Me HH Me HHH 4b Me HH Br HHH 5b Me HH Cl HHH 6b Me HHF ₃ CHHH 7b Me HH NH ₂ C (= O) HHH 8b Me HHO ₂ NHHH 9b Me HH Ph HHH 10b Me H Me HHHH 11b Me H Me H Me HH 12b Me Me HHHHH 13b Me MeO HHHHH 14b Me HO HHHHH 15b Me HO Br HHHH 16b Me H ₂ NHHHHH 17b Me H ₂ N Br HHHH 18b Me PhCH ₂ C (= O) HHHHH 19b Me CF ₃ C (= O) NH HHHHH 20b Et HHHHHH 21b 1-Me-1-Et HHHHHH 22b 1-Me-1-Et HH Me HHH 23b Pr HHHHHH 24b cBu HHHHHH 25b 1-Me-cPr HHHHHH 26b Ph HHHHHH (H27H MeC = O) HHHHHH 28b Me ₂ NC (= O) HHHHHH 29b NH ₂ C (= O) HHHHHH 30b F ₃ CHHHHHHH 31b F ₃ CHH Me HHH 32b F ₃ CHH Cl HHH 33b HOOC HHHHHH 34b MeOCH ₂ HHHHHHH = 35O ) HHHHHH 36b MeOC (= O) HH Me HHH 37b Me HHH ₂ NHHH 38b (CH ₃ ) ₂ CH HH Me HHH 39b NH ₂ C (= O) HH Me HHH ------------- -------------------------------------------------- -- the above In 3, preferred are, 1b, 2b, 3b,
4b, 5b, 6b, 10b, 11b, 12b, 13b,
14b, 15b, 16b, 17b, 19b, 20b, 2
1b, 22b, 23b, 24b, 25b, 27b, 28
b, 29b, 30b, 31b, 32b, 33b, 34
b, 35b, 37b, 38b and 39b, and more preferred are 2b, 3b, 5b, 10b, 12b, 1
3b, 14b, 16b, 21b, 22b, 30b, 31
b and 32b.

[0044]

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[0045]

[Table 4] ---------------------------------------------- ^{------------------- No. R 4 R 7 R 8} R 26 R 27 R 28 R 29 --------------- -------------------------------------------------- 1c HHHHHHH 2c Me HHHHHH 3c Me HH Me HHH 4c Me HH Br HHH 5c Me HH Cl HHH 6c Me HHF ₃ CHHH 7c Me HH NH ₂ C (= O) HHH 8c Me HHO ₂ NHHH 9c Me HH Ph HHH 10c Me H Me HHHH 11c Me H Me H Me HH 12c Me Me HHHHH 13c Me MeO HHHHH 14c Me HO HHHHH 15c Me HO Br HHHH 16c Me H 2 NHHHHH 17c Me H 2 N Br HHHH 18c Me PhCH 2 C (= O) HHHHH 19c Me CF ₃ C (= O) NH HHHHH 20c Et HHHHHH 21c 1-Me-1-Et HHHHHH 22c 1-Me-1-Et HH Me HHH 23c Pr HHHHHH 24c cBu HHHHHH 25c 1-Me-cPr HHHHHH 26c Ph HHHHHH (27C MeNHC = O) HHHHHH 28c Me ₂ NC (= O) HHHHHH 29c NH ₂ C (= O) HHHHHH 30c F3C HHHHHHH31c F ₃ CHH Me HHH 32c F ₃ CHH Cl HHH 33c HOOC HHHHHH 34c MeOCH ₂ HHHHHO 35C MeOC HHHHHH 36c MeOC (= O) HH Me HHH 37c Me HHH ₂ NHHH 38c (CH ₃ ) ₂ CH HH Me HHH 39c NH ₂ C (= O) HH Me HHH -------------- -------------------------------------------------- -The table above In 4, preferred are 1c, 2c, 3c,
4c, 5c, 6c, 10c, 11c, 12c, 13c,
14c, 15c, 16c, 17c, 19c, 20c, 2
1c, 22c, 23c, 24c, 25c, 27c, 28
c, 29c, 30c, 31c, 32c, 33c, 34
c, 35c, 37c, 38c and 39c, more preferably 2c, 3c, 5c, 10c, 12c, 1c.
3c, 14c, 16c, 21c, 22c, 30c, 31
c and 32c.

[0046]

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[0047]

[Table 5] ---------------------------------------------- ^{------------------- No. R 4 R 7 R 8} R 30 R 31 R 32 R 33 --------------- -------------------------------------------------- 1d HHHHHHH 2d Me HHHHHH 3d Me HH Me HHH 4d Me HH Br HHH 5d Me HH Cl HHH 6d Me HHF ₃ CHHH 7d Me HH NH ₂ C (= O) HHH 8d Me HHO ₂ NHHH 9d Me HH Ph HHH 10d Me H Me HHHH 11d Me H Me H Me HH 12d Me Me HHHHH 13d Me MeO HHHHH 14d Me HO HHHHH 15d Me HO Br HHHH 16d Me H ₂ NHHHHH 17d Me H ₂ N Br HHHH 18d Me PhCH ₂ C (= O) HHHHH 19d Me CF ₃ C (= O) NH HHHHH 20d Et HHHHHH 21d 1-Me-1-Et HHHHHH 22d 1-Me-1-Et HH Me HHH 23d Pr HHHHHH 24d cBu HHHHHH 25d 1-Me-cPr HHHHHH 26d Ph HHHHHH (HdH = O) HHHHHH 28d Me ₂ NC (= O) HHHHHH 29d NH ₂ C (= O) HHHHHH 30d F ₃ CHHHHHH31d F ₃ CHH Me HHH 32d F ₃ CHH Cl HHH 33d HOOC HHHHHH 34d MeOCH ₂ HHHHHHHOH = 35d MeOC ) HHHHHH 36d MeOC (= O) HH Me HHH 37d Me HHH ₂ NHHH 38d (CH ₃ ) ₂ CH HH Me HHH 39d NH ₂ C (= O) HH Me HHH ------------- -------------------------------------------------- -- the above In 5, preferred are, 1d, 2d, 3d,
4d, 5d, 6d, 10d, 11d, 12d, 13d,
14d, 15d, 16d, 17d, 19d, 20d, 2
1d, 22d, 23d, 24d, 25d, 27d, 28
d, 29d, 30d, 31d, 32d, 33d, 34
d, 35d, 37d, 38d and 39d, more preferred are 2d, 3d, 5d, 10d, 12d, 1d
3d, 14d, 16d, 21d, 22d, 30d, 31
d and 32d.

Specific examples of the compound (1) of the present invention include:
Select one arbitrarily from Table 1, Table 2, Table 3, Table 4, and Table
Combinations obtained by arbitrarily selecting one from 5
Specifically, for example, 1-1a, 1-2a, 1-7
a, 1-21a, 1-33a, 1-39a, 2-15
a, 3-1a, 3-2a, 3-3a, 3-4a, 3-5
a, 3-6a, 3-10a, 3-11a, 3-12a,
3-13a, 3-14a, 3-20a, 3-21a, 3
-25a, 3-30a, 3-30a, 3-31a, 3-
32a, 3-34a, 3-35a, 3-39a, 4-2
a, 4-6a, 4-11a, 4-15a, 4-23a,
4-27a, 5-2a, 5-5a, 5-7a, 5-10
a, 5-14a, 5-19a, 5-28a, 5-30
a, 6-2a, 6-3a, 6-4a, 6-5a, 6-6
a, 6-10a, 6-12a, 6-19a, 7-2a,
7-1a, 7-3a, 8-2a, 8-27a, 8-29
a, 9-2a, 9-4a, 9-6a, 9-8a, 9-1
0a, 10-2a, 10-3a, 10-4a, 10-5
a, 10-9a, 10-11a, 10-29a, 10-
35a, 14-2a, 15-2a, 16-1a, 16-
2a, 16-2a, 16-3a, 16-4a, 16-5
a, 16-6a, 16-10a, 16-11a, 16-
12a, 16-13a, 16-14a, 16-15a,
16-17a, 16-20a, 16-21a, 16-2
3a, 16-25a, 16-30a, 16-31a, 1
6-32a, 16-34a, 16-35a, 17-2
a, 17-3a, 17-5a, 18-1a, 18-2
a, 18-3a, 18-4a, 18-5a, 18-6
a, 18-10a, 18-12a, 18-13a, 18
-14a, 18-15a, 18-16a, 18-17
a, 18-19a, 18-20a, 18-21a, 18
-23a, 18-25a, 18-27a, 18-28
a, 18-29a, 18-30a, 18-31a, 18
-32a, 18-33a, 18-34a, 18-35
a, 19-2a, 20-2a, 20-4a, 20-5
a, 21-1a, 21-8a, 21-19a, 22-2
a, 23-2a, 24-2a, 24-2a, 24-3
a, 24-4a, 24-5a, 24-10a, 24-1
2a, 24-13a, 24-20a, 24-25a, 2
4-30a, 25-3a, 23-5a, 26-2a, 2
7-1a, 27-2a, 27-3a, 27-4a, 27
-5a, 27-6a, 27-10a, 27-11a, 2
7-12a, 27-13a, 27-14a, 27-15
a, 27-15a, 27-20a, 27-21a, 27
-25a, 27-30a, 27-31a, 27-32
a, 27-34a, 27-35a, 28-2a, 29-
2a, 30-2a, 31-2a, 32-3a, 33-1
a, 33-2a, 33-3a, 33-4a, 33-5
a, 33-6a, 33-10a, 33-12a, 33-
13a, 33-14a, 33-20a, 33-25a,
33-30a, 34-2a, 35-2a, 36-2a,
38-2a, 39-2a, 40-5a, 41-2a, 4
2-2a, 42-10a, 43-2a, 44-2a, 4
5-2a, 46-2a, 47-9a, 48-14a, 4
9-2a, 50-2a, 51-3a, 52-4a, 53
-6a, 54-7a, 55-8a, 56-2a, 57-
1a, 57-2a, 57-3a, 57-3a, 57-4
a, 57-5a, 57-5a, 57-6a, 57-10
a, 57-12a, 57-13a, 57-14a, 57
-15a, 57-20a, 57-21a, 57-24
a, 57-25a, 57-30a, 57-31a, 57
-32a, 57-34a, 57-35a, 57-38
a, 57-39a, 58-1a, 58-2a, 59-2
a, 60-2a, 61-2a, 62-2a, 63-2
a, 64-2a, 65-2a, 66-2a, 67-2
a, 68-2a, 69-2a, 70-2a, 71-2
a, 72-2a, 73-2a, 74-2a, 75-2
a, 76-2a, 77-2a, 78-2a, 79-2
a, 80-2a, 80-3a, 81-2a, 82-2
a, 101-2a, 101-3a, 101-4a, 10
2-2a, 102-3a, 103-2a, 104-2
a, 105-2a, 106-2a, 106-3a, 10
7-2a, 108-2a, 109-2a, 110-2
a, 111-2a, 112-3a, 113-4a, 11
4-2a, 115-2a, 116-2a, 117-2
a, 118-2a, 119-2a, 120-2a, 12
1-2a, 122-3a, 124-2a, 125-2
a, 125-3a, 125-5a, 125-13a, 1
26-13a, 127-5a, 128-2a, 128-
3a, 128-5a, 128-6a, 128-13a,
128-22a, 128-29a, 128-31a, 1
28-37a, 129-2a, 130-2a, 131-
2a, 132-2a, 133-3a, 134-10a,
135-2a, 136-2a, 137-3a, 138-
2a, 139-2a, 140-2a, 141-2a, 1
42-2a, 143-3a, 144-3a, 145-3
a, 146-3a, 147-13a, 148-2a, 1
49-13a, 1-1b, 1-2b, 1-7b, 1-2
1b, 1-33b, 1-39b, 2-15b, 3-1
b, 3-2b, 3-3b, 3-4b, 3-5b, 3-6
b, 3-10b, 3-11b, 3-12b, 3-13
b, 3-14b, 3-20b, 3-21b, 3-25
b, 3-30b, 3-30b, 3-31b, 3-32
b, 3-34b, 3-35b, 3-39b, 4-2b,
4-6b, 4-11b, 4-15b, 4-23b, 4-
27b, 5-2b, 5-5b, 5-7b, 5-10b,
5-14b, 5-19b, 5-28b, 5-30b, 6
-2b, 6-3b, 6-4b, 6-5b, 6-6b, 6
-10b, 6-12b, 6-19b, 7-2b, 7-1
b, 7-3b, 8-2b, 8-27b, 8-29b, 9
-2b, 9-4b, 9-6b, 9-8b, 9-10b,
10-2b, 10-3b, 10-4b, 10-5b, 1
0-9b, 10-11b, 10-29b, 10-35
b, 14-2b, 15-2b, 16-1b, 16-2
b, 16-2b, 16-3b, 16-4b, 16-5
b, 16-6b, 16-10b, 16-11b, 16-
12b, 16-13b, 16-14b, 16-15b,
16-17b, 16-20b, 16-21b, 16-2
3b, 16-25b, 16-30b, 16-31b, 1
6-32b, 16-34b, 16-35b, 17-2
b, 17-3b, 17-5b, 18-1b, 18-2
b, 18-3b, 18-4b, 18-5b, 18-6
b, 18-10b, 18-12b, 18-13b, 18
-14b, 18-15b, 18-16b, 18-17
b, 18-19b, 18-20b, 18-21b, 18
-23b, 18-25b, 18-27b, 18-28
b, 18-29b, 18-30b, 18-31b, 18
-32b, 18-33b, 18-34b, 18-35
b, 19-2b, 20-2b, 20-4b, 20-5
b, 21-1b, 21-8b, 21-19b, 22-2
b, 23-2b, 24-2b, 24-2b, 24-3
b, 24-4b, 24-5b, 24-10b, 24-1
2b, 24-13b, 24-20b, 24-25b, 2
4-30b, 25-3b, 23-5b, 26-2b, 2
7-1b, 27-2b, 27-3b, 27-4b, 27
-5b, 27-6b, 27-10b, 27-11b, 2
7-12b, 27-13b, 27-14b, 27-15
b, 27-15b, 27-20b, 27-21b, 27
-25b, 27-30b, 27-31b, 27-32
b, 27-34b, 27-35b, 28-2b, 29-
2b, 30-2b, 31-2b, 32-3b, 33-1
b, 33-2b, 33-3b, 33-4b, 33-5
b, 33-6b, 33-10b, 33-12b, 33-
13b, 33-14b, 33-20b, 33-25b,
33-30b, 34-2b, 35-2b, 36-2b,
38-2b, 39-2b, 40-5b, 41-2b, 4
2-2b, 42-10b, 43-2b, 44-2b, 4
5-2b, 46-2b, 47-9b, 48-14b, 4
9-2b, 50-2b, 51-3b, 52-4b, 53
-6b, 54-7b, 55-8b, 56-2b, 57-
1b, 57-2b, 57-3b, 57-3b, 57-4
b, 57-5b, 57-5b, 57-6b, 57-10
b, 57-12b, 57-13b, 57-14b, 57
-15b, 57-20b, 57-21b, 57-24
b, 57-25b, 57-30b, 57-31b, 57
-32b, 57-34b, 57-35b, 57-38
b, 57-39b, 58-1b, 58-2b, 59-2
b, 60-2b, 61-2b, 62-2b, 63-2
b, 64-2b, 65-2b, 66-2b, 67-2
b, 68-2b, 69-2b, 70-2b, 71-2
b, 72-2b, 73-2b, 74-2b, 75-2
b, 76-2b, 77-2b, 78-2b, 79-2
b, 80-2b, 80-3b, 81-2b, 82-2
b, 101-2b, 101-3b, 101-4b, 10
2-2b, 102-3b, 103-2b, 104-2
b, 105-2b, 106-2b, 106-3b, 10
7-2b, 108-2b, 109-2b, 110-2
b, 111-2b, 112-3b, 113-4b, 11
4-2b, 115-2b, 116-2b, 117-2
b, 118-2b, 119-2b, 120-2b, 12
1-2b, 122-3b, 124-2b, 125-2
b, 125-3b, 125-5b, 125-13b, 1
26-13b, 127-5b, 128-2b, 128-
3b, 128-5b, 128-6b, 128-13b,
128-22b, 128-29b, 128-31b, 1
28-37b, 129-2b, 130-2b, 131-
2b, 132-2b, 133-3b, 134-10b,
135-2b, 136-2b, 137-3b, 138-
2b, 139-2b, 140-2b, 141-2b, 1
42-2b, 143-3b, 144-3b, 145-3
b, 146-3b, 147-13b, 148-2b, 1
49-13b, 1-1c, 1-2c, 1-7c, 1-2
1c, 1-33c, 1-39c, 2-15c, 3-1
c, 3-2c, 3-3c, 3-4c, 3-5c, 3-6
c, 3-10c, 3-11c, 3-12c, 3-13
c, 3-14c, 3-20c, 3-21c, 3-25
c, 3-30c, 3-30c, 3-31c, 3-32
c, 3-34c, 3-35c, 3-39c, 4-2c,
4-6c, 4-11c, 4-15c, 4-23c, 4-
27c, 5-2c, 5-5c, 5-7c, 5-10c,
5-14c, 5-19c, 5-28c, 5-30c, 6
-2c, 6-3c, 6-4c, 6-5c, 6-6c, 6
-10c, 6-12c, 6-19c, 7-2c, 7-1
c, 7-3c, 8-2c, 8-27c, 8-29c, 9
-2c, 9-4c, 9-6c, 9-8c, 9-10c,
10-2c, 10-3c, 10-4c, 10-5c, 1
0-9c, 10-11c, 10-29c, 10-35
c, 14-2c, 15-2c, 16-1c, 16-2
c, 16-2c, 16-3c, 16-4c, 16-5
c, 16-6c, 16-10c, 16-11c, 16-
12c, 16-13c, 16-14c, 16-15c,
16-17c, 16-20c, 16-21c, 16-2
3c, 16-25c, 16-30c, 16-31c, 1
6-32c, 16-34c, 16-35c, 17-2
c, 17-3c, 17-5c, 18-1c, 18-2
c, 18-3c, 18-4c, 18-5c, 18-6
c, 18-10c, 18-12c, 18-13c, 18
-14c, 18-15c, 18-16c, 18-17
c, 18-19c, 18-20c, 18-21c, 18
-23c, 18-25c, 18-27c, 18-28
c, 18-29c, 18-30c, 18-31c, 18
-32c, 18-33c, 18-34c, 18-35
c, 19-2c, 20-2c, 20-4c, 20-5
c, 21-1c, 21-8c, 21-19c, 22-2
c, 23-2c, 24-2c, 24-2c, 24-3
c, 24-4c, 24-5c, 24-10c, 24-1
2c, 24-13c, 24-20c, 24-25c, 2
4-30c, 25-3c, 23-5c, 26-2c, 2
7-1c, 27-2c, 27-3c, 27-4c, 27
-5c, 27-6c, 27-10c, 27-11c, 2
7-12c, 27-13c, 27-14c, 27-15
c, 27-15c, 27-20c, 27-21c, 27
-25c, 27-30c, 27-31c, 27-32
c, 27-34c, 27-35c, 28-2c, 29-
2c, 30-2c, 31-2c, 32-3c, 33-1
c, 33-2c, 33-3c, 33-4c, 33-5
c, 33-6c, 33-10c, 33-12c, 33-
13c, 33-14c, 33-20c, 33-25c,
33-30c, 34-2c, 35-2c, 36-2c,
38-2c, 39-2c, 40-5c, 41-2c, 4
2-2c, 42-10c, 43-2c, 44-2c, 4
5-2c, 46-2c, 47-9c, 48-14c, 4
9-2c, 50-2c, 51-3c, 52-4c, 53
-6c, 54-7c, 55-8c, 56-2c, 57-
1c, 57-2c, 57-3c, 57-3c, 57-4
c, 57-5c, 57-5c, 57-6c, 57-10
c, 57-12c, 57-13c, 57-14c, 57
-15c, 57-20c, 57-21c, 57-24
c, 57-25c, 57-30c, 57-31c, 57
-32c, 57-34c, 57-35c, 57-38
c, 57-39c, 58-1c, 58-2c, 59-2
c, 60-2c, 61-2c, 62-2c, 63-2
c, 64-2c, 65-2c, 66-2c, 67-2
c, 68-2c, 69-2c, 70-2c, 71-2
c, 72-2c, 73-2c, 74-2c, 75-2
c, 76-2c, 77-2c, 78-2c, 79-2
c, 80-2c, 80-3c, 81-2c, 82-2
c, 101-2c, 101-3c, 101-4c, 10
2-2c, 102-3c, 103-2c, 104-2
c, 105-2c, 106-2c, 106-3c, 10
7-2c, 108-2c, 109-2c, 110-2
c, 111-2c, 112-3c, 113-4c, 11
4-2c, 115-2c, 116-2c, 117-2
c, 118-2c, 119-2c, 120-2c, 12
1-2c, 122-3c, 124-2c, 125-2
c, 125-3c, 125-5c, 125-13c, 1
26-13c, 127-5c, 128-2c, 128-
3c, 128-5c, 128-6c, 128-13c,
128-22c, 128-29c, 128-31c, 1
28-37c, 129-2c, 130-2c, 131-
2c, 132-2c, 133-3c, 134-10c,
135-2c, 136-2c, 137-3c, 138-
2c, 139-2c, 140-2c, 141-2c, 1
42-2c, 143-3c, 144-3c, 145-3
c, 146-3c, 147-13c, 148-2c, 1
49-13c, 1-1d, 1-2d, 1-7d, 1-2
1d, 1-33d, 1-39d, 2-15d, 3-1
d, 3-2d, 3-3d, 3-4d, 3-5d, 3-6
d, 3-10d, 3-11d, 3-12d, 3-13
d, 3-14d, 3-20d, 3-21d, 3-25
d, 3-30d, 3-30d, 3-31d, 3-32
d, 3-34d, 3-35d, 3-39d, 4-2d,
4-6d, 4-11d, 4-15d, 4-23d, 4-
27d, 5-2d, 5-5d, 5-7d, 5-10d,
5-14d, 5-19d, 5-28d, 5-30d, 6
-2d, 6-3d, 6-4d, 6-5d, 6-6d, 6
-10d, 6-12d, 6-19d, 7-2d, 7-1
d, 7-3d, 8-2d, 8-27d, 8-29d, 9
-2d, 9-4d, 9-6d, 9-8d, 9-10d,
10-2d, 10-3d, 10-4d, 10-5d, 1
0-9d, 10-11d, 10-29d, 10-35
d, 14-2d, 15-2d, 16-1d, 16-2
d, 16-2d, 16-3d, 16-4d, 16-5
d, 16-6d, 16-10d, 16-11d, 16-
12d, 16-13d, 16-14d, 16-15d,
16-17d, 16-20d, 16-21d, 16-2
3d, 16-25d, 16-30d, 16-31d, 1
6-32d, 16-34d, 16-35d, 17-2
d, 17-3d, 17-5d, 18-1d, 18-2
d, 18-3d, 18-4d, 18-5d, 18-6
d, 18-10d, 18-12d, 18-13d, 18
-14d, 18-15d, 18-16d, 18-17
d, 18-19d, 18-20d, 18-21d, 18
-23d, 18-25d, 18-27d, 18-28
d, 18-29d, 18-30d, 18-31d, 18
-32d, 18-33d, 18-34d, 18-35
d, 19-2d, 20-2d, 20-4d, 20-5
d, 21-1d, 21-8d, 21-19d, 22-2
d, 23-2d, 24-2d, 24-2d, 24-3
d, 24-4d, 24-5d, 24-10d, 24-1
2d, 24-13d, 24-20d, 24-25d, 2
4-30d, 25-3d, 23-5d, 26-2d, 2
7-1d, 27-2d, 27-3d, 27-4d, 27
-5d, 27-6d, 27-10d, 27-11d, 2
7-12d, 27-13d, 27-14d, 27-15
d, 27-15d, 27-20d, 27-21d, 27
-25d, 27-30d, 27-31d, 27-32
d, 27-34d, 27-35d, 28-2d, 29-
2d, 30-2d, 31-2d, 32-3d, 33-1
d, 33-2d, 33-3d, 33-4d, 33-5
d, 33-6d, 33-10d, 33-12d, 33-
13d, 33-14d, 33-20d, 33-25d,
33-30d, 34-2d, 35-2d, 36-2d,
38-2d, 39-2d, 40-5d, 41-2d, 4
2-2d, 42-10d, 43-2d, 44-2d, 4
5-2d, 46-2d, 47-9d, 48-14d, 4
9-2d, 50-2d, 51-3d, 52-4d, 53
-6d, 54-7d, 55-8d, 56-2d, 57-
1d, 57-2d, 57-3d, 57-3d, 57-4
d, 57-5d, 57-5d, 57-6d, 57-10
d, 57-12d, 57-13d, 57-14d, 57
-15d, 57-20d, 57-21d, 57-24
d, 57-25d, 57-30d, 57-31d, 57
-32d, 57-34d, 57-35d, 57-38
d, 57-39d, 58-1d, 58-2d, 59-2
d, 60-2d, 61-2d, 62-2d, 63-2
d, 64-2d, 65-2d, 66-2d, 67-2
d, 68-2d, 69-2d, 70-2d, 71-2
d, 72-2d, 73-2d, 74-2d, 75-2
d, 76-2d, 77-2d, 78-2d, 79-2
d, 80-2d, 80-3d, 81-2d, 82-2
d, 101-2d, 101-3d, 101-4d, 10
2-2d, 102-3d, 103-2d, 104-2
d, 105-2d, 106-2d, 106-3d, 10
7-2d, 108-2d, 109-2d, 110-2
d, 111-2d, 112-3d, 113-4d, 11
4-2d, 115-2d, 116-2d, 117-2
d, 118-2d, 119-2d, 120-2d, 12
1-2d, 122-3d, 124-2d, 125-2
d, 125-3d, 125-5d, 125-13d, 1
26-13d, 127-5d, 128-2d, 128-
3d, 128-5d, 128-6d, 128-13d,
128-22d, 128-29d, 128-31d, 1
28-37d, 129-2d, 130-2d, 131-
2d, 132-2d, 133-3d, 134-10d,
135-2d, 136-2d, 137-3d, 138-
2d, 139-2d, 140-2d, 141-2d, 1
42-2d, 143-3d, 144-3d, 145-3
d, 146-3d, 147-13d, 148-2d, 1
49-13d, 448-3a, 449-3a, 450-
3a, 451-3a, 452-3a, 453-3a, 4
54-3a, 455-3a, 456-3a, 457-3
a, 458-3a, 459-3a, 460-3a, 46
1-3a, 462-3a, 463-3a, 464-3
a, 465-3a, 466-3a, 467-3a, 46
8-3a, 469-3a, 470-3a, 471-3
a, 472-3a, 473-3a, 474-3a, 47
5-3a, 476-3a, 477-3a, 478-3
a, 479-3a, 480-3a, 481-3a, 48
2-3a, 483-3a, 484-3a, 485-3
a, 486-3a, 487-3a, 488-3a, 48
9-3a, 490-3a, 491-3a, 492-3
a, 493-3a, 494-3a, 495-3a, 49
6-3a, 497-3a, 498-3a, 499-3
a, 500-3a, 501-3a, 502-3a, 50
3-3a, 504-3a, 505-3a, 506-3
a, 507-3a, 508-3a, 509-3a, 51
0-3a, 511-3a, 512-3a, 513-3
a, 514-3a, 515-3a, 516-3a, 51
7-3a, 518-3a, 519-3a, 520-3
a, 521-3a, 522-3a, 523-3a, 52
4-3a, 525-3a, 526-3a, 527-3
a, 528-3a, 529-3a, 530-3a, 53
1-3a, 532-3a, 533-3a, 534-3
a, 535-3a, 536-3a, 537-3a, 53
8-3a, 539-3a, 540-3a, 541-3
a, 542-3a, 543-3a, 544-3a, 54
5-3a, 546-3a, 547-3a, 548-3
a, 549-3a, 550-3a, 551-3a, 55
2-3a, 553-3a, 554-3a, 555-3
a, 556-3a, 557-3a, 558-3a, 55
9-3a, 560-3a, 561-3a, 562-3
a, 563-3a, 564-3a, 565-3a, 56
6-3a, 567-3a, 568-3a, 569-3
a, 570-3a, 571-3a, 572-3a, 57
3-3a, 574-3a, 575-3a, 576-3
a, 577-3a, 578-3a, 579-3a, 58
0-3a, 581-3a, 582-3a, 583-3
a, 584-3a, 585-3a, 586-3a, 58
7-3a, 588-3a, 589-3a, 590-3
a, 591-3a, 592-3a, 593-3a, 59
4-3a, 595-3a, 596-3a, 597-3
a, 598-3a, 599-3a, 448-5a, 44
9-5a, 450-5a, 451-5a, 452-5
a, 453-5a, 454-5a, 455-5a, 45
6-5a, 457-5a, 458-5a, 459-5
a, 460-5a, 461-5a, 462-5a, 46
3-5a, 464-5a, 465-5a, 466-5
a, 467-5a, 468-5a, 469-5a, 47
0-5a, 471-5a, 472-5a, 473-5
a, 474-5a, 475-5a, 476-5a, 47
7-5a, 478-5a, 479-5a, 480-5
a, 481-5a, 482-5a, 483-5a, 48
4-5a, 485-5a, 486-5a, 487-5
a, 488-5a, 489-5a, 490-5a, 49
1-5a, 492-5a, 493-5a, 494-5
a, 495-5a, 496-5a, 497-5a, 49
8-5a, 499-5a, 500-5a, 501-5
a, 502-5a, 503-5a, 504-5a, 50
5-5a, 506-5a, 507-5a, 508-5
a, 509-5a, 510-5a, 511-5a, 51
2-5a, 513-5a, 514-5a, 515-5
a, 516-5a, 517-5a, 518-5a, 51
9-5a, 520-5a, 521-5a, 522-5
a, 523-5a, 524-5a, 525-5a, 52
6-5a, 527-5a, 528-5a, 529-5
a, 530-5a, 531-5a, 532-5a, 53
3-5a, 534-5a, 535-5a, 536-5
a, 537-5a, 538-5a, 539-5a, 54
0-5a, 541-5a, 542-5a, 543-5
a, 544-5a, 545-5a, 546-5a, 54
7-5a, 548-5a, 549-5a, 550-5
a, 551-5a, 552-5a, 553-5a, 55
4-5a, 555-5a, 556-5a, 557-5
a, 558-5a, 559-5a, 560-5a, 56
1-5a, 562-5a, 563-5a, 564-5
a, 565-5a, 566-5a, 567-5a, 56
8-5a, 569-5a, 570-5a, 571-5
a, 572-5a, 573-5a, 574-5a, 57
5-5a, 576-5a, 577-5a, 578-5
a, 579-5a, 580-5a, 581-5a, 58
2-5a, 583-5a, 584-5a, 585-5
a, 586-5a, 587-5a, 588-5a, 58
9-5a, 590-5a, 591-5a, 592-5
a, 593-5a, 594-5a, 595-5a, 59
6-5a, 597-5a, 598-5a, 599-5
a, 448-31a, 449-31a, 450-31
a, 451-31a, 452-31a, 453-31
a, 454-31a, 455-31a, 456-31
a, 457-31a, 458-31a, 459-31
a, 460-31a, 461-31a, 462-31
a, 463-31a, 464-31a, 465-31
a, 466-31a, 467-31a, 468-31
a, 469-31a, 470-31a, 471-31
a, 472-31a, 473-31a, 474-31
a, 475-31a, 476-31a, 477-31
a, 478-31a, 479-31a, 480-31
a, 481-31a, 482-31a, 483-31
a, 484-31a, 485-31a, 486-31
a, 487-31a, 488-31a, 489-31
a, 490-31a, 491-31a, 492-31
a, 493-31a, 494-31a, 495-31
a, 496-31a, 497-31a, 498-31
a, 499-31a, 500-31a, 501-31
a, 502-31a, 503-31a, 504-31
a, 505-31a, 506-31a, 507-31
a, 508-31a, 509-31a, 510-31
a, 511-31a, 512-31a, 513-31
a, 514-31a, 515-31a, 516-31
a, 517-31a, 518-31a, 519-31
a, 520-31a, 521-31a, 522-31
a, 523-31a, 524-31a, 525-31
a, 526-31a, 527-31a, 528-31
a, 529-31a, 530-31a, 531-31
a, 532-31a, 533-31a, 534-31
a, 535-31a, 536-31a, 537-31
a, 538-31a, 539-31a, 540-31
a, 541-31a, 542-31a, 543-31
a, 544-31a, 545-31a, 546-31
a, 547-31a, 548-31a, 549-31
a, 550-31a, 551-31a, 552-31
a, 553-31a, 554-31a, 555-31
a, 556-31a, 557-31a, 558-31
a, 559-31a, 560-31a, 561-31
a, 562-31a, 563-31a, 564-31
a, 565-31a, 566-31a, 567-31
a, 568-31a, 569-31a, 570-31
a, 571-31a, 572-31a, 573-31
a, 574-31a, 575-31a, 576-31
a, 577-31a, 578-31a, 579-31
a, 580-31a, 581-31a, 582-31
a, 583-31a, 584-31a, 585-31
a, 586-31a, 587-31a, 588-31
a, 589-31a, 590-31a, 591-31
a, 592-31a, 593-31a, 594-31
a, 595-31a, 596-31a, 597-31
a, 598-31a or 599-31a.

Particularly preferably, [4- (2-methyl-imidazo [1,
2-α] pyridin-3-yl) -thiazol-2-yl]-(4-trif
Fluoromethyl-phenyl) -amine, [4- (2-methyl-imida
Zo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -p-to
Ryl-amine, (4-methoxy-phenyl)-[4- (2-methyl-i
Midazo [1,2-α] pyridin-3-yl) -thiazol-2-yl]-
Amine, [4- (2-methyl-imidazo [1,2-α] pyridine-3-i
) -Thiazol-2-yl] -phenyl-amine, (2-methoxy)
C-phenyl)-[4- (2-methyl-imidazo [1,2-α] pyridine
-3-yl) -thiazol-2-yl] -amine, (3,4-dimethoxy)
C-phenyl)-[4- (2-methyl-imidazo [1,2-α] pyridine
-3-yl) -thiazol-2-yl] -amine, (3,5-dimethoxy)
C-phenyl)-[4- (2-methyl-imidazo [1,2-α] pyridine
-3-yl) -thiazol-2-yl] -amine, [4- (2-methyl-
Imidazo [1,2-α] pyridin-3-yl) -thiazol-2-i
]-(4-propyl-phenyl) -amine, N- [4- [4- (2-methyl
Ru-imidazo [1,2-α] pyridin-3-yl) -thiazole-2-
Ylamino] -phenyl] -acetamide, (4-isopropyl
Ru-phenyl)-[4- (2-methyl-imidazo [1,2-α] pyridine
-3-yl) -thiazol-2-yl] -amine, (4-ethyl-fe
Nyl)-[4- (2-methyl-imidazo [1,2-α] pyridine-3-i
Ru) -thiazol-2-yl] -amine, (4-isopropoxy-
Phenyl)-[4- (2-methyl-imidazo [1,2-α] pyridine-3-
Yl) -thiazol-2-yl] -amine, 4- [4- (2-methyl-i
Midazo [1,2-α] pyridin-3-yl) -thiazol-2-yla
Mino] -benzoic acid ethyl ester, (3,5-dimethyl-phenyl
Nyl)-[4- (2-methyl-imidazo [1,2-α] pyridine-3-i
) -Thiazol-2-yl] -amine, (4-ethoxy-phenyl)
-)-[4- (2-Methyl-imidazo [1,2-α] pyridin-3-yl)-
Thiazol-2-yl] -amine, 3- [4- (2-methyl-imida)
Zo [1,2-α] pyridin-3-yl) -thiazol-2-ylami
[No] -phenol, (2,4-dimethyl-phenyl)-[4- (2-meth
Tyl-imidazo [1,2-α] pyridin-3-yl) -thiazole-2
-Yl] -amine, (3,5-bis-trifluoromethyl-phenyl
-)-[4- (2-Methyl-imidazo [1,2-α] pyridin-3-yl)-
Thiazol-2-yl] -amine, [4- (2-methyl-imidazo)
[1,2-α] pyridin-3-yl) -thiazol-2-yl]-(2,3,4
-Trifluoro-phenyl) -amine, 4- [4- (2-methyl-i
Midazo [1,2-α] pyridin-3-yl) -thiazol-2-yla
Mino] -phenol, (4-tert-butyl-phenyl)-[4- (2-
Methyl-imidazo [1,2-α] pyridin-3-yl) -thiazole
2-yl] -amine, 4- [4- (2-methyl-imidazo [1,2-α] pi
Lysin-3-yl) -thiazol-2-ylamino] -benzoic acid
Tyl ester, (3,4-dimethyl-phenyl)-[4- (2-methyl
Ru-imidazo [1,2-α] pyridin-3-yl) -thiazole-2-
Yl] -amine, (4-chloro-phenyl)-[4- (2-methyl-i
Midazo [1,2-α] pyridin-3-yl) -thiazol-2-yl]-
Amine, (3-fluoro-4-methyl-phenyl)-[4- (2-methyl
Ru-imidazo [1,2-α] pyridin-3-yl) -thiazole-2-
Yl] -amine, 1- [4- [4- (2-methyl-imidazo [1,2-α] pi
Lysin-3-yl) -thiazol-2-ylamino] -phenyl]-
Ethanone, (6-methoxy-pyridin-3-yl)-[4- (2-methyl
Ru-imidazo [1,2-α] pyridin-3-yl) -thiazole-2-
Yl] -amine, (6-chloro-pyridin-3-yl)-[4- (2-meth
Tyl-imidazo [1,2-α] pyridin-3-yl) -thiazole-2
-Yl] -amine, 1- [4- [4- (2,5,7-trimethyl-imidazo
[1,2-α] pyridin-3-yl) -thiazol-2-ylamino]-
Phenyl] -ethanone, p-tolyl- [4- (2,5,7-trimethyl-
Imidazo [1,2-α] pyridin-3-yl) -thiazol-2-i
] -Amine, (4-trifluoromethyl-phenyl)-[4- (2,
5,7-trimethyl-imidazo [1,2-α] pyridin-3-yl) -thio
Azol-2-yl] -amine, [4- (2,8-dimethyl-imidazo)
[1,2-α] pyridin-3-yl) -thiazol-2-yl]-(4-meth
Toxi-phenyl) -amine, 1- [4- [4- (2,8-dimethyl-i
Midazo [1,2-α] pyridin-3-yl) -thiazol-2-yla
[Mino] -phenyl] -ethanone, [4- (2,8-dimethyl-imida)
Zo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -p-to
Ryl-amine, 4- [4- (2,8-dimethyl-imidazo [1,2-α] pi
Lysin-3-yl) -thiazol-2-ylamino] -benzoic acid
Tyl ester, [4- (2,8-dimethyl-imidazo [1,2-α] pi
Lysin-3-yl) -thiazol-2-yl]-(6-methoxy-pyri
Zin-3-yl) -amine, [4- (2,8-dimethyl-imidazo [1,2
-α] pyridin-3-yl) -thiazol-2-yl]-(4-trif
Fluoromethyl-phenyl) -amine, [4- (2,6-dimethyl-i
Midazo [1,2-α] pyridin-3-yl) -thiazol-2-yl]-
(4-methoxy-phenyl) -amine, 1- [4- [4- (2,6-dimethyl)
Ru-imidazo [1,2-α] pyridin-3-yl) -thiazole-2-
Ylamino] -phenyl] -ethanone, [4- (2,6-dimethyl-
Imidazo [1,2-α] pyridin-3-yl) -thiazol-2-i
Ru] -p-tolyl-amine, 4- [4- (2,6-dimethyl-imidazo
[1,2-α] pyridin-3-yl) -thiazol-2-ylamino]-
Ethyl benzoate, [4- (2,6-dimethyl-imidazo
[1,2-α] pyridin-3-yl) -thiazol-2-yl]-(6-meth
Toxyl-pyridin-3-yl) -amine, [4- (2,6-dimethyl-
Imidazo [1,2-α] pyridin-3-yl) -thiazol-2-i
L]-(4-trifluoromethyl-phenyl) -amine, [4- (2,
7-dimethyl-imidazo [1,2-α] pyridin-3-yl) -thiazo
-2-yl]-(4-methoxy-phenyl) -amine, 1- [4- [4
-(2,7-Dimethyl-imidazo [1,2-α] pyridin-3-yl) -thio
Azol-2-ylamino] -phenyl] -ethanone, [4- (2,7
-Dimethyl-imidazo [1,2-α] pyridin-3-yl) -thiazo
2-yl] -p-tolyl-amine, 4- [4- (2,7-dimethyl-
Imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl
Amino] -benzoic acid ethyl ester, [4- (2,7-dimethyl-
Imidazo [1,2-α] pyridin-3-yl) -thiazol-2-i
L]-(6-Methoxy-pyridin-3-yl) -amine, [4- (2,7-
Dimethyl-imidazo [1,2-α] pyridin-3-yl) -thiazole
Ru-2-yl]-(4-trifluoromethyl-phenyl) -ami
, (4-methoxy-phenyl)-[5-methyl-4- (2-methyl-y
Midazo [1,2-α] pyridin-3-yl) -thiazol-2-yl]-
Amine, 1- [4- [5-methyl-4- (2-methyl-imidazo [1,2-
α] pyridin-3-yl) -thiazol-2-ylamino] -fe
Nyl] -ethanone, [5-methyl-4- (2-methyl-imidazo [1,2
-α] pyridin-3-yl) -thiazol-2-yl] -p-tolyl-
Amine, (6-methoxy-pyridin-3-yl)-[5-methyl-4-
(2-methyl-imidazo [1,2-α] pyridin-3-yl) -thiazo
2-yl] -amine, [5-methyl-4- (2-methyl-imida)
Zo [1,2-α] pyridin-3-yl) -thiazol-2-yl]-(4-
(Trifluoromethyl-phenyl) -amine, (4-methoxy-
Phenyl)-[4- (2-methyl-6-trifluoromethyl-imida
Zo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -ami
, 1- [4- [4- (2-methyl-6-trifluoromethyl-imida
Zo [1,2-α] pyridin-3-yl) -thiazol-2-ylami
[No] -phenyl] -ethanone, [4- (2-methyl-6-trifluoro)
L-methyl-imidazo [1,2-α] pyridin-3-yl) -thiazole
Ru-2-yl] -p-tolyl-amine, 4- [4- (2-methyl-6-tri
Fluoromethyl-imidazo [1,2-α] pyridin-3-yl) -thio
Azol-2-ylamino] -benzoic acid ethyl ester, (6
-Methoxy-pyridin-3-yl)-[4- (2-methyl-6-trifur
Oromethyl-imidazo [1,2-α] pyridin-3-yl) -thiazo
2-yl] -amine, [4- (2-methyl-6-trifluoromethyl)
Tyl-imidazo [1,2-α] pyridin-3-yl) -thiazole-2
-Yl]-(4-trifluoromethyl-phenyl) -amine, [4-
(6-Chloro-2-methyl-imidazo [1,2-α] pyridine-3-i
Ru) -thiazol-2-yl]-(4-methoxy-phenyl) -ami
1- [4- [4- (6-chloro-2-methyl-imidazo [1,2-α] pi
Lysin-3-yl) -thiazol-2-ylamino] -phenyl]-
Etanone, 4- [4- (6-chloro-2-methyl-imidazo [1,2-α]
Pyridin-3-yl) -thiazol-2-ylamino] -benzoic acid
Ethyl ester, [4- (6-chloro-2-methyl-imidazo [1,
2-α] pyridin-3-yl) -thiazol-2-yl]-(6-methoxy
C-pyridin-3-yl) -amine, [4- (6-chloro-2-methyl-
Imidazo [1,2-α] pyridin-3-yl) -thiazol-2-i
]-(4-trifluoromethyl-phenyl) -amine, [4- (6-
Chloro-2-methyl-imidazo [1,2-α] pyridin-3-yl)-
Thiazol-2-yl] -p-tolyl-amine, [4- (6-bromo-2
-Methyl-imidazo [1,2-α] pyridin-3-yl) -thiazole
Ru-2-yl]-(4-methoxy-phenyl) -amine, 1- [4- [4-
(6-Bromo-2-methyl-imidazo [1,2-α] pyridine-3-i
Ru) -thiazol-2-ylamino] -phenyl] -ethanone,
[4- (6-Bromo-2-methyl-imidazo [1,2-α] pyridine-3-
Yl) -thiazol-2-yl] -p-tolyl-amine, 4- [4- (6-
Bromo-2-methyl-imidazo [1,2-α] pyridin-3-yl)-
Thiazol-2-ylamino] -benzoic acid ethyl ester,
[4- (6-Bromo-2-methyl-imidazo [1,2-α] pyridine-3-
Yl) -thiazol-2-yl]-(6-methoxy-pyridin-3-i
) -Amine, [4- (6-bromo-2-methyl-imidazo [1,2-α]
Pyridin-3-yl) -thiazol-2-yl]-(4-trifluoro)
L-methyl-phenyl) -amine, 4- [4- (2-methyl-imida)
Zo [1,2-α] pyridin-3-yl) -thiazol-2-ylami
No] -benzonitrile, 4- [4- (2,6-dimethyl-imidazo [1,
2-α] pyridin-3-yl) -thiazol-2-ylamino] -be
Zononitrile, 4- [4- (2,7-dimethyl-imidazo [1,2-α]
Pyridin-3-yl) -thiazol-2-ylamino] -benzoni
Tolyl, 4- [4- (2,8-dimethyl-imidazo [1,2-α] pyridi
3-Nyl) -thiazol-2-ylamino] -benzonitrile
4- [4- (6-chloro-2-methyl-imidazo [1,2-α] pyridi
3-Nyl) -thiazol-2-ylamino] -benzonitrile
4- [4- (6-bromo-2-methyl-imidazo [1,2-α] pyridi
3-Nyl) -thiazol-2-ylamino] -benzonitrile
, N- (4-methoxy-phenyl) -N- [4- (2-methyl-imida
Zo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -ace
Toamide, 2,2,2-trifluoro-N- (4-methoxy-phenyl
) -N- [4- (2-methyl-imidazo [1,2-α] pyridine-3-i
Ru) -thiazol-2-yl] -acetamide, N- (4-methoxy
-Phenyl) -N- [4- (2-methyl-imidazo [1,2-α] pyridine
-3-yl) -thiazol-2-yl] -benzamide, 2,2,2-to
Trifluoro-N- (4-hydroxy-phenyl) -N- [4- (2-methyl
Ru-imidazo [1,2-α] pyridin-3-yl) -thiazole-2-
Yl] -acetamide, 4-methoxy-N- (4-methoxy-
Nyl) -N- [4- (2-methyl-imidazo [1,2-α] pyridine-3-i
) -Thiazol-2-yl] -benzamide, (4-methoxy-
Phenyl) -methyl- [4- (2-methyl-imidazo [1,2-α] pyri
Zin-3-yl) -thiazol-2-yl] -amine, 4-methoxy
-N- [4- (2-Methyl-imidazo [1,2-α] pyridin-3-yl)-
Thiazol-2-yl] -benzamide, N- [4- (2-methyl-i
Midazo [1,2-α] pyridin-3-yl) -thiazol-2-yl]-
4-nitro-benzamide, 2- [4- [4- (2-methyl-imidazo
[1,2-α] pyridin-3-yl) -thiazol-2-ylamino]-
Phenyl] -propan-2-ol, N-ethyl-4- [4- (2-methyl
Ru-imidazo [1,2-α] pyridin-3-yl) -thiazole-2-
Ylamino] -benzamide, 4- [4- (2-methyl-imidazo
[1,2-α] pyridin-3-yl) -thiazol-2-ylamino]-
Benzamide, N-methyl-4- [4- (2-methyl-imidazo [1,2
-α] Pyridin-3-yl) -thiazol-2-ylamino] -ben
Zuamide, N, N-dimethyl-4- [4- (2-methyl-imidazo [1,2
-α] Pyridin-3-yl) -thiazol-2-ylamino] -ben
Zuamide, N-methoxy-N-methyl-4- [4- (2-methyl-imi
Dazo [1,2-α] pyridin-3-yl) -thiazol-2-ylami
[No] -benzamide, (4-methoxy-phenyl)-[4- (2-methyl
Ru-imidazo [1,2-α] pyridin-3-yl) -thiazole-2-
Yl] -amine hydrobromide, 1- [4- [4- (2-methyl-imi
Dazo [1,2-α] pyridin-3-yl) -thiazol-2-ylami
[No] -phenyl] -ethanone hydrobromide, [4- (2-methyl
-Imidazo [1,2-α] pyridin-3-yl) -thiazol-2-i
] -P-tolyl-amine hydrobromide, 4- [4- (2-methyl-
Imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl
Amino] -ethyl benzoate hydrobromide, (6-
Methoxy-pyridin-3-yl)-[4- (2-methyl-imidazo [1,
2-α] pyridin-3-yl) -thiazol-2-yl] -amine
Hydrobromide, [4- (2-methyl-imidazo [1,2-α] pyridi
3-yl) -thiazol-2-yl]-(4-trifluoromethyl
-Phenyl-amine hydrobromide, 4- [4- (2-methyl-
Imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl
Amino] -benzonitrile hydrobromide, 1- [4- [4- (8-
Hydroxy-2-methyl-imidazo [1,2-α] pyridine-3-i
Ru) -thiazol-2-ylamino] -phenyl] -ethanone
Hydrobromide, 1- [4- [4- (7-bromo-8-hydroxy-2-me
Tyl-imidazo [1,2-α] pyridin-3-yl) -thiazole-2
-Ylamino] -phenyl] -ethanone hydrobromide, 1-
[4- [4- (2-methoxymethyl-imidazo [1,2-α] pyridine-3
-Yl) -thiazol-2-ylamino] -phenyl] -ethanone
Hydrobromide, [4- (2-methoxymethyl-imidazo [1,2-
α] pyridin-3-yl) -thiazol-2-yl] -p-tolyl-a
Min hydrobromide, [4- (2-methoxymethyl-imidazo
[1,2-α] pyridin-3-yl) -thiazol-2-yl]-(6-meth
Toxi-pyridin-3-yl) -amine hydrobromide, [4
-(2-methoxymethyl-imidazo [1,2-α] pyridine-3-
Yl) -thiazol-2-yl]-(4-trifluoromethyl-phenyl
Enyl) -amine hydrobromide, [4- (2-ethyl-imida
Zo [1,2-α] pyridin-3-yl) -thiazol-2-yl]-(4-
(Methoxy-phenyl) -amine hydrobromide, 1- [4- [4-
(2-ethyl-imidazo [1,2-α] pyridin-3-yl) -thiazo
2-ylamino] -phenyl] -ethanone, [4- (2-ethyl
Ru-imidazo [1,2-α] pyridin-3-yl) -thiazole-2-
Yl] -p-tolyl-amine hydrobromide, 4- [4- (2-ethyl
Ru-imidazo [1,2-α] pyridin-3-yl) -thiazole-2-
Ilamino] -ethyl benzoate hydrobromic acid
Salt, [4- (2-ethyl-imidazo [1,2-α] pyridin-3-yl)-
Thiazol-2-yl]-(6-methoxy-pyridin-3-yl) -a
Min hydrobromide, [4- (2-ethyl-imidazo [1,2-α]
Pyridin-3-yl) -thiazol-2-yl]-(4-trifluoro)
Romethyl-phenyl) -amine hydrobromide, 4- [4- (2-
Ethyl-imidazo [1,2-α] pyridin-3-yl) -thiazole
2-ylamino] -benzonitrile hydrobromide, 3- [2-
(4-methoxy-phenylamino) -thiazol-4-yl] -a
Midazo [1,2-α] pyridine-2-carboxylic acid methyl ester
Hydrobromide, 3- [2- (4-acetyl-phenylamino)-
Thiazol-4-yl] -imidazo [1,2-α] pyridine-2-cal
Bonic acid methyl ester hydrobromide, 3- (2-p-tolyl
Amino-thiazol-4-yl) -imidazo [1,2-α] pyridine
2-Carboxylic acid methyl ester hydrobromide, 3- [2-
(6-Methoxy-pyridin-3-ylamino) -thiazol-4-i
Methyl] -imidazo [1,2-α] pyridine-2-carboxylate
Ster hydrobromide, 3- [2- (4-trifluoromethyl-
Phenylamino) -thiazol-4-yl] -imidazo [1,2-
α] pyridine-2-carboxylic acid methyl ester hydrogen bromide
Acid salt, (2,4-dimethoxy-phenyl)-[4- (2-methyl-imi
Dazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -a
Min, [4- (2-methyl-imidazo [1,2-α] pyridine-3-i
Ru) -thiazol-2-yl]-(4-nitro-phenyl) -ami
, (3,4-dichloro-phenyl)-[4- (2-methyl-imidazo
[1,2-α] pyridin-3-yl) -thiazol-2-yl] -ami
, (4-methoxy-phenyl)-[4- (2-trifluoromethyl
-Imidazo [1,2-α] pyridin-3-yl) -thiazol-2-i
L-amine, 1- [4- [4- (2-trifluoromethyl-imidazo)
[1,2-α] pyridin-3-yl) -thiazol-2-ylamino]-
Phenyl] -ethanone, p-tolyl- [4- (2-trifluoromethyl
Tyl-imidazo [1,2-α] pyridin-3-yl) -thiazole-2
-Yl] -amine, 4- [4- (2-trifluoromethyl-imidazo
[1,2-α] pyridin-3-yl) -thiazol-2-ylamino]-
Ethyl benzoate, (6-methoxy-pyridine-3-i
)-[4- (2-trifluoromethyl-imidazo [1,2-α] pyri
Zin-3-yl) -thiazol-2-yl] -amine, [4- (2-tri
Fluoromethyl-imidazo [1,2-α] pyridin-3-yl) -thio
Azol-2-yl]-(4-trifluoromethyl-phenyl)-
Amine, 4- [4- (2-trifluoromethyl-imidazo [1,2-
α] pyridin-3-yl) -thiazol-2-ylamino] -ben
Zonitrile, 7-bromo-3- [2- (4-methoxy-phenylamido)
No) -thiazol-4-yl] -2-methyl-imidazo [1,2-α] pi
Lysine-8-ylamine, 7-bromo-2-methyl-3- [2- (4-t
(Trifluoromethyl-phenylamino) -thiazol-4-i
Ru] -imidazo [1,2-α] pyridin-8-ylamine, (4-imidazo
Dazo [1,2-α] pyridin-3-yl-thiazol-2-yl)-(4-
Methoxy-phenyl) -amine, 1- [4- (4-imidazo [1,2-
α] pyridin-3-yl-thiazol-2-ylamino) -phenyl
Ru] -Ethanone, 4-imidazo [1,2-α] pyridin-3-yl-thio
Azol-2-yl) -p-tolyl-amine, 4- (4-imidazo [1,
2-α] pyridin-3-yl-thiazol-2-ylamino) -benzo
Ethyl fragrance, (4-imidazo [1,2-α] pyridine-3
-Yl-thiazol-2-yl)-(6-methoxy-pyridin-3-i
) -Amine, (4-imidazo [1,2-α] pyridin-3-yl-thio
Azol-2-yl)-(4-trifluoromethyl-phenyl)-
Amines, [4- (8-methoxy-2-methyl-imidazo [1,2-α] pi
Lysin-3-yl) -thiazol-2-yl]-(4-methoxy-fe
Nil) -amine, 1- [4- [4- (8-methoxy-2-methyl-imida)
Zo [1,2-α] pyridin-3-yl) -thiazol-2-ylami
[No] -phenyl] -ethanone, [4- (8-methoxy-2-methyl-i
Midazo [1,2-α] pyridin-3-yl) -thiazol-2-yl]-
p-tolyl-amine, 4- [4- (8-methoxy-2-methyl-imida
Zo [1,2-α] pyridin-3-yl) -thiazol-2-ylami
[No] -benzoic acid ethyl ester, [4- (8-methoxy-2-methyi)
Ru-imidazo [1,2-α] pyridin-3-yl) -thiazole-2-
Yl]-(6-methoxy-pyridin-3-yl) -amine, [4- (8-
Methoxy-2-methyl-imidazo [1,2-α] pyridin-3-yl)
-Thiazol-2-yl]-(4-trifluoromethyl-phenyl
) -Amine, 4- [4- (8-methoxy-2-methyl-imidazo [1,
2-α] pyridin-3-yl) -thiazol-2-ylamino] -be
Zononitrile, 1- [4- [4- (8-hydroxy-2-methyl-imi
Dazo [1,2-α] pyridin-3-yl) -thiazol-2-ylami
[No] -phenyl] -ethanone, 3- [2- (4-methoxy-phenyl)
Amino) -thiazol-4-yl] -2-methyl-imidazo [1,2-
α] pyridin-8-ol, 2-methyl-3- (2-p-tolylamino
-Thiazol-4-yl) -imidazo [1,2-α] pyridine-8-o
, 4- [4- (8-hydroxy-2-methyl-imidazo [1,2-α]
Pyridin-3-yl) -thiazol-2-ylamino] -benzoic acid
Ethyl ester, 3- [2- (6-methoxy-pyridin-3-yl)
Amino) -thiazol-4-yl] -2-methyl-imidazo [1,2-
α] pyridin-8-ol, 2-methyl-3- [2- (4-trifluoro
Romethyl-phenylamino) -thiazol-4-yl] -imida
Zo [1,2-α] pyridin-8-ol, 1- [4- [4- (7-bromo-8-
Hydroxy-2-methyl-imidazo [1,2-α] pyridine-3-i
Ru) -thiazol-2-ylamino] -phenyl] -ethanone,
2,2,2-trifluoro-N- [3- [2- (4-methoxy-phenyla
Mino) -thiazol-4-yl] -2-methyl-imidazo [1,2-α]
Pyridin-8-yl] -acetamide, 3- [2- (4-methoxy-phenyl)
Enylamino) -thiazol-4-yl] -2-methyl-imidazo
[1,2-α] pyridin-8-ylamine, 3- [2- (4-methoxy-phenyl)
Enylamino) -thiazol-4-yl] -imidazo [1,2-α]
Pyridine-2-carboxylic acid, 3- [2- (4-methoxy-phenyla
Mino) -thiazol-4-yl] -imidazo [1,2-α] pyridine-
2-carboxylic amide, 3- [2- (4-methoxy-phenylamido)
No) -thiazol-4-yl] -imidazo [1,2-α] pyridine-2-
Carboxylic acid methylamide, 3- [2- (4-methoxy-phenyl)
Amino) -thiazol-4-yl] -imidazo [1,2-α] pyridi
2-Carboxylic acid dimethylamide, N- (4-acetyl-fe
Nyl) -N- [4- (2,6-dimethyl-imidazo [1,2-α] pyridine-
3-yl) -thiazol-2-yl] -acetamide, N- (4-acetamide
Tyl-phenyl) -N- [4- (6-chloro-2-methyl-imidazo [1,
2-α] pyridin-3-yl) -thiazol-2-yl] -acetoa
Mido, [4- (2-methoxymethyl-imidazo [1,2-α] pyridi
3-Nyl) -thiazol-2-yl]-(4-methoxy-phenyl)
) -Amine hydrobromide, [4- (isopropylimidazo
[1,2-α] pyridin-3-yl) -thiazol-2-yl]-(6-meth
Toxyl-pyridin-3-yl) -amine, p-tolyl- [4- (2-to
Trifluoromethyl-imidazo [1,2-α] pyridin-3-yl)-
Thiazol-2-yl] -amine dihydrochloride, [4- (6-chloro-2-
Trifluoromethyl-imidazo [1,2-α] pyridine-3-i
Ru) -thiazol-2-yl]-(6-methoxy-pyridin-3-i
) -Amine, (6-methoxy-pyridin-3-yl)-[4- (6-
Tyl-2-trifluoromethyl-imidazo [1,2-α] pyridine
-3-yl) -thiazol-2-yl] -amine, N- (6-methoxy-
Pyridin-3-yl) -N- [4- (6-methyl-2-trifluoromethyl
Ru-imidazo [1,2-α] pyridin-3-yl) -thiazole-2-
Yl] -acetamide, [4- (2,6-dimethyl-imidazo [1,2-
α] pyridin-3-yl) -thiazol-2-yl]-(6-methoxy
-Pyridin-3-yl) -amine dihydrochloride, [4- (2,6-dimethyl
-Imidazo [1,2-α] pyridin-3-yl) -thiazol-2-i
Ru]-(4-Trifluoromethyl-phenyl) -amine hydrochloric acid
Salt, [4- (6-chloro-2-methyl-imidazo [1,2-α] pyridine
-3-yl) -thiazol-2-yl] -p-tolyl-amine dihydrochloride
Salt, [4- (6-chloro-2-methyl-imidazo [1,2-α] pyridine
-3-yl) -thiazol-2-yl]-(6-methoxy-pyridine-3
-Yl) -amine dihydrochloride, N- [4- (2,6-dimethyl-imidazo
[1,2-α] pyridin-3-yl) -thiazol-2-yl] -N- (6-
Methoxy-pyridin-3-yl) -acetamide, N- [4- (6-
Loro-2-methyl-imidazo [1,2-α] pyridin-3-yl) -thio
Azol-2-yl] -N- (6-methoxy-pyridin-3-yl) -a
Cetamide, N- [4- (2-isopropyl-6-methyl-imidazo
[1,2-α] pyridin-3-yl) -thiazol-2-yl] -N- (6-
Methoxy-pyridin-3-yl) -acetamide, N- (6-meth
Xy-pyridin-3-yl) -N- [4- (2-methyl-imidazo [1,2-
α] pyridin-3-yl) -thiazol-2-yl] -acetamido
, N- [4- (2,6-dimethyl-imidazo [1,2-α] pyridine-3-
Yl) -thiazol-2-yl] -N- (6-methoxy-pyridine-3-
Yl) -isobutylamide, N- [4- (2,6-dimethyl-imida
Zo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -N- (6
-Methoxy-pyridin-3-yl) -propioamide, [4- (2,6
-Dimethyl-imidazo [1,2-α] pyridin-3-yl) -thiazo
2-yl]-(6-methoxy-pyridin-3-yl) -carbami
Acid methyl ester, 1- [4- (2,6-dimethyl-imidazo
[1,2-α] pyridin-3-yl) -thiazol-2-yl] -1- (6-
(Methoxy-pyridin-3-yl) -3,3-dimethyl-urea, 3-
[2- [acetyl- (6-methoxy-pyridin-3-yl) -amino]-
Thiazol-4-yl] -6-methyl-imidazo [1,2-α] pyridi
2-Carboxyamide, [4- (2,6-dimethyl-imidazo
[1,2-α] pyridin-3-yl) -thiazol-2-yl]-(6-meth
Toxi-pyridin-3-yl) -amine hydrobromide and N- [4
-(8-Methoxy-2-methyl-imidazo [1,2-α] pyridine-3-
Yl) -thiazol-2-yl] -Np-tolyl-acetamide
And the most preferred compound is [4- (2-methyl-imidazo [1,
2-α] pyridin-3-yl) -thiazol-2-yl]-(4-trif
(Fluoromethyl-phenyl) -amine (16-2a), (4-me
Toxi-phenyl)-[4- (2-methyl-imidazo [1,2-α] pyri
Zin-3-yl) -thiazol-2-yl] -amine (18-2
a), (6-Methoxy-pyridin-3-yl)-[4- (2-methyl-i
Midazo [1,2-α] pyridin-3-yl) -thiazol-2-yl]-
Amine (56-2a), (6-methoxy-pyridin-3-yl)
-[4- (2-Methyl-imidazo [1,2-α] pyridin-3-yl) -thio
Azol-2-yl] -amine (59-2a), [4- (2,8-di
Methyl-imidazo [1,2-α] pyridin-3-yl) -thiazole
-2-yl]-(6-methoxy-pyridin-3-yl) -amine (57
-2a), [4- (2,6-dimethyl-imidazo [1,2-α] pyridi
3-Nyl) -thiazol-2-yl]-(4-methoxy-phenyl)
1) -amine (18-3a), 1- [4- [4- (2,6-dimethyl-i
Midazo [1,2-α] pyridin-3-yl) -thiazol-2-yla
Mino] -phenyl] -ethanone (27-3a), [4- (2,6-di
Methyl-imidazo [1,2-α] pyridin-3-yl) -thiazole
-2-yl] -p-tolyl-amine (3-3a), [4- (2,6-dimethyl)
Tyl-imidazo [1,2-α] pyridin-3-yl) -thiazole-2
-Yl]-(6-methoxy-pyridin-3-yl) -amine (57-
3a), [4- (2,6-dimethyl-imidazo [1,2-α] pyridine-
3-yl) -thiazol-2-yl]-(4-trifluoromethyl-
Phenyl) -amine (16-3a), [4- (2,7-dimethyl-
Imidazo [1,2-α] pyridin-3-yl) -thiazol-2-i
Ru]-(6-Methoxy-pyridin-3-yl) -amine (57-1)
0a), (4-methoxy-phenyl)-[5-methyl-4- (2-methyl
Ru-imidazo [1,2-α] pyridin-3-yl) -thiazole-2-
Yl] -amine (77-2a), [5-methyl-4- (2-methyl-
Imidazo [1,2-α] pyridin-3-yl) -thiazol-2-i
Ru]-(4-trifluoromethyl-phenyl) -amine (81-
2a), [4- (6-chloro-2-methyl-imidazo [1,2-α] pyri
Zin-3-yl) -thiazol-2-yl]-(4-methoxy-phenyl)
) -Amine (18-5a), 1- [4- [4- (6-chloro-2-methyl)
Ru-imidazo [1,2-α] pyridin-3-yl) -thiazole-2-
Ylamino] -phenyl] -ethanone (27-5a), [4-
(6-Chloro-2-methyl-imidazo [1,2-α] pyridine-3-i
Ru) -thiazol-2-yl]-(6-methoxy-pyridin-3-i
) -Amine (57-5a), [4- (6-chloro-2-methyl-i)
Midazo [1,2-α] pyridin-3-yl) -thiazol-2-yl]-
p-tolyl-amine (3-5a), N-methyl-4- [4- (2-methyl
Ru-imidazo [1,2-α] pyridin-3-yl) -thiazole-2-
Ilamino] -benzamide (29-2a), (4-methoxy
C-phenyl)-[4- (2-trifluoromethyl-imidazo [1,2
-α] pyridin-3-yl) -thiazol-2-yl] -amine (1
8-30a), (4-methoxy-phenyl)-[4- (2-trifur
Oromethyl-imidazo [1,2-α] pyridin-3-yl) -thiazo
2-yl] -amine (3-30a), (6-methoxy-pi
Lysin-3-yl)-[4- (2-trifluoromethyl-imidazo
[1,2-α] pyridin-3-yl) -thiazol-2-yl] -amine
(57-30a), [4- (8-methoxy-2-methyl-imidazo)
[1,2-α] pyridin-3-yl) -thiazol-2-yl]-(6-meth
Toxy-pyridin-3-yl) -amine (57-13a), 3-
[2- (6-Methoxy-pyridin-3-ylamino) -thiazole-4
-Yl] -2-methyl-imidazo [1,2-α] pyridin-8-ol
(57-14a), 2,2,2-trifluoro-N- [3- [2- (4-me
Toxi-phenylamino) -thiazol-4-yl] -2-methyl
-Imidazo [1,2-α] pyridin-8-yl] -acetamide (1
8-16a), [4- (Isopropylimidazo [1,2-α] pyri]
Zin-3-yl) -thiazol-2-yl]-(6-methoxy-pyridi
N-3-yl) -amine (57-21a), p-tolyl- [4- (2-
Trifluoromethyl-imidazo [1,2-α] pyridine-3-i
Ru) -thiazol-2-yl] -amine dihydrochloride (3-30
a), [4- (6-chloro-2-trifluoromethyl-imidazo
[1,2-α] pyridin-3-yl) -thiazol-2-yl]-(6-meth
Toxi-pyridin-3-yl) -amine (57-32a), (6
-Methoxy-pyridin-3-yl)-[4- (6-methyl-2-trifur
Oromethyl-imidazo [1,2-α] pyridin-3-yl) -thiazo
2-yl] -amine (57-31a), N- (6-methoxy)
-Pyridin-3-yl) -N- [4- (6-methyl-2-trifluoromethyl
Tyl-imidazo [1,2-α] pyridin-3-yl) -thiazole-2
-Yl] -acetamide (128-31a), [4- (2,6-di
Methyl-imidazo [1,2-α] pyridin-3-yl) -thiazole
-2-yl]-(6-methoxy-pyridin-3-yl) -amine dihydrochloride
Salt (57-3a), [4- (2,6-dimethyl-imidazo [1,2-
α] pyridin-3-yl) -thiazol-2-yl]-(4-trifur
Oromethyl-phenyl) -amine hydrochloride (16-3
a), [4- (6-chloro-2-methyl-imidazo [1,2-α] pyridi
3-yl) -thiazol-2-yl] -p-tolyl-amine disalt
Acid salt (3-5a), [4- (6-chloro-2-methyl-imidazo)
[1,2-α] pyridin-3-yl) -thiazol-2-yl]-(6-meth
Toxi-pyridin-3-yl) -amine dihydrochloride (57-5
a), N- [4- (2,6-dimethyl-imidazo [1,2-α] pyridine-
3-yl) -thiazol-2-yl] -N- (6-methoxy-pyridine-
3-yl) -acetamide (128-3a), N- [4- (6-chloro
Ro-2-methyl-imidazo [1,2-α] pyridin-3-yl) -thia
Zol-2-yl] -N- (6-methoxy-pyridin-3-yl) -ace
Toamide (128-5a), N- [4- (2-isopropyl-6-
Methyl-imidazo [1,2-α] pyridin-3-yl) -thiazole
-2-yl] -N- (6-methoxy-pyridin-3-yl) -acetamido
(128-22a), N- (6-methoxy-pyridine-3-i
) -N- [4- (2-methyl-imidazo [1,2-α] pyridine-3-i
Ru) -thiazol-2-yl] -acetamide (128-2
a), N- [4- (2,6-dimethyl-imidazo [1,2-α] pyridine-
3-yl) -thiazol-2-yl] -N- (6-methoxy-pyridine-
3-yl) -isobutylamide (143-3a), N- [4- (2,
6-dimethyl-imidazo [1,2-α] pyridin-3-yl) -thiazo
2-yl] -N- (6-methoxy-pyridin-3-yl) -propyl
Oamide (144-3a), [4- (2,6-dimethyl-imida)
Zo [1,2-α] pyridin-3-yl) -thiazol-2-yl]-(6-
Methoxy-pyridin-3-yl) -carbamic acid methyl ester
Ter (145-3a), 1- [4- (2,6-dimethyl-imidazo)
[1,2-α] pyridin-3-yl) -thiazol-2-yl] -1- (6-
Methoxy-pyridin-3-yl) -3,3-dimethyl-urea (1
46-3a), 3- [2- [acetyl- (6-methoxy-pyridine-
3-yl) -amino] -thiazol-4-yl] -6-methyl-imida
Zo [1,2-α] pyridine-2-carboxylic acid amide (128-2
9a), [4- (2,6-dimethyl-imidazo [1,2-α] pyridine-
3-yl) -thiazol-2-yl]-(6-methoxy-pyridin-3-
Yl) -amine hydrobromide (57-3a) and N- [4- (8-
Methoxy-2-methyl-imidazo [1,2-α] pyridin-3-yl)
-Thiazol-2-yl] -Np-tolyl-acetamide (14
7-13a).

[0050]

BEST MODE FOR CARRYING OUT THE INVENTION The compound (1) of the present invention can be produced by the following methods A to C. (Method A)

[0051]

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(Method B)

[0053]

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(Method C)

[0055]

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[0056] In the process ^{sheet, R 1 a, R 2 a} , R 3 a,
^{R 4 a, R 5 a,} R 6 a, R 7 a and R ⁸ a are each, R ^1,
The same groups as R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ are shown. When it has a suitable functional group, the functional group is a protected group, X ¹ has the same meaning as described above, and L represents a hydroxyl group or a leaving group. (Method A) (First Step) This step is a step of reacting compound (2) with compound (3) in an inert solvent to produce compound (1a) of the present invention.

Examples of the solvent to be used include aromatic hydrocarbons such as benzene, toluene and xylene; esters such as ethyl formate, ethyl acetate, propyl acetate, butyl acetate and diethyl carbonate; Etano
Alcohols such as n-propanol, isopropanol, n-butanol, isobutanol, t-butanol, isoamyl alcohol, diethylene glycol, glycerin, octanol, cyclohexanol and methyl cellosolve Ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone and cyclohexanone; nitro compounds such as nitroethane and nitrobenzene; nitriles such as acetonitrile and isobutyronitrile; formamide, N, N-dimethylformamide; N, N-dimethylacetamide, N-
Amides such as methyl-2-pyrrolidone, N-methylpyrrolidinone, and hexamethyl phosphorotriamide; sulfoxides such as dimethyl sulfoxide and sulfolane can be mentioned, and preferred are alcohols.

The reaction temperature varies depending on the starting compound and solvent used, but is usually from 0 ° C. to 100 ° C., preferably from 20 ° C. to 80 ° C.

The reaction time varies depending on the starting compound, solvent and reaction temperature used, but is usually 30 minutes to 36 hours, preferably 1 hour to 18 hours.

After completion of the reaction, the target compound (1)
For example, the reaction mixture is concentrated, and an immiscible organic solvent such as water and ethyl acetate is added. Alternatively, it can be obtained by adsorbing a by-product hydrohalic acid to an aminated resin and concentrating the residue under reduced pressure.

The obtained compound can be further purified, if necessary, by a conventional method, for example, recrystallization, silica gel column chromatography and the like. (Second Step) This step is, there is carried out optionally, deprotecting the protecting group on R ¹ a to R ⁸ a, is a step for preparing a compound of the present invention (1b).

As long as the method does not involve any side reaction, a conventional method may be used. For example, Protective Groups in
Organic Synthesis third edition (1999, Wiley-In
terscience). (Method B) (Third step) This step is a step of reacting compound (2) with compound (4) in an inert solvent to produce compound (1c) of the present invention.

This step is performed in the same manner as in the first step except that compound (3) is used instead of compound (4). (Fourth step) This step is, there is carried out optionally, deprotecting the protecting group on R ¹ a to R ⁸ a, is a step for preparing a compound of the present invention (1d).

This step is performed in the same manner as in the second step. (Method C) (Fifth Step) This step is a step of reacting the compound (1a) produced in the first step with the compound (5) to produce the compound (1c) of the present invention.

The method of this step differs depending on the type of compound (5). <1> When the compound (5) is an alkyl halide In this step, the compound (1a) produced in the first step is reacted with the compound (5) in an inert solvent in the presence of a base, and the present invention This is the step of producing the compound (1c).

Examples of the solvent used include nitro compounds such as nitroethane and nitrobenzene; nitriles such as acetonitrile and isobutyronitrile;
Formamide, N, N-dimethylformamide, N, N
Amides such as dimethylacetamide, N-methyl-2-pyrrolidone, N-methylpyrrolidinone, hexamethylphosphorotriamide; sulfoxides such as dimethylsulfoxide and sulfolane; N-methylmorpholine, triethylamine, tripropylamine, tripropylamine Butylamine, diisopropylethylamine, dicyclohexylamine, N-methylpiperidine, pyridine, 4-pyrrolidinopyridine, picoline, 4- (N, N-dimethylamino) pyridine, 2,6-di (t-butyl) -4-methylpyridine , Quinoline, N, N-dimethylaniline,
Organic bases such as N, N-diethylaniline can be mentioned, and are preferably organic bases.

The base used includes, for example, alkali metal hydrides such as lithium hydride, sodium hydride and potassium hydride; sodium methoxide, sodium ethoxide, potassium methoxide, potassium ethoxide, potassium t Alkali metal alkoxides such as butoxide and lithium methoxide; N-methylmorpholine, triethylamine, tripropylamine, tributylamine, diisopropylethylamine, dicyclohexylamine, N-methylpiperidine, pyridine,
-Pyrrolidinopyridine, picoline, 4- (N, N-dimethylamino) pyridine, 2,6-di (t-butyl) -4
-Methylpyridine, quinoline, N, N-dimethylaniline, N, N-diethylaniline, 1,5-diazabicyclo [4.3.0] non-5-ene (DBN), 1,4-
Diazabicyclo [2.2.2] octane (DABC
O) and organic bases such as 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU), and are preferably organic bases. However, when the organic base is used as a solvent, it is not necessary to additionally use a base.

The reaction temperature varies depending on the starting compounds and the solvent used, but is usually from 0 ° C. to 100 ° C., preferably from 20 ° C. to 80 ° C.

The reaction time varies depending on the starting compound, solvent and reaction temperature used, but is usually 30 minutes to 24 hours, preferably 1 hour to 8 hours.

After completion of the reaction, the target compound of this reaction is obtained, for example, by concentrating the reaction mixture, adding an immiscible organic solvent such as water and ethyl acetate, washing with water, separating the organic layer containing the target compound, and adding anhydrous It is obtained by drying over magnesium sulfate or the like and then distilling off the solvent.

The obtained compound can be further purified, if necessary, by a conventional method, for example, recrystallization, silica gel column chromatography and the like.

The obtained compound (1c) can be converted to compound (1d) by performing the reaction in the second step. <2> When compound (5) is carboxylic acid, acyl halide, acid anhydride, etc. In these cases, the reaction can be carried out according to the method of the following sixth step.

The compound (2) as a raw material for producing the compound (1) of the present invention is known or can be produced by the following D to F methods. (Method D)

[0074]

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(Method E)

[0076]

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(Method F)

[0078]

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In the above process chart, R^Threea, R^Foura, R^Fivea,
R⁶a, R⁷a, R⁸a, X¹And Hal are as defined above.
And R^Foura is the above R^TenHas the same meaning as^Fourb is the above R^Ten
-X ^ThreeAnd L is a hydroxyl group or a leaving group.
And M represents a metal atom or a metal halide;
The term “metal atom” refers to the ionization in a reaction system,
Means an atom that generates
Is, for example, lithium atom, sodium atom, potassium
Alkali such as atom, rubidium atom, cesium atom
Metal atoms include “metal halide”
Is ionized in the reaction system to generate anions.
A group such as bromomag
Nesium, chloromagnesium, magnesium iodide group
Magnesium halide groups such as
Preferably a lithium atom or a bromomagnesium group
It is. (Method D) (Sixth step) In this step, compound (6) and compound (7)
Is a step of producing a compound (8).

When L is a hydroxyl group, the compound (6) and the compound (7) are reacted with each other in an inert solvent in the presence of a base and a condensing agent to produce a compound (8). In the case of leaving group, the compound (6) and the compound (7) are reacted in an inert solvent in the presence of a base to produce a compound (8). <1> When L is a hydroxyl group: Examples of the solvent used include ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, dimethoxyethane, and diethylene glycol dimethyl ether; acetone, methyl ethyl ketone, and methyl isobutyl. Ketones such as ketone, isophorone and cyclohexanone; nitro compounds such as nitroethane and nitrobenzene; nitriles such as acetonitrile and isobutyronitrile; formamide, N, N-dimethylformamide, N, N-dimethylacetamide, N -Methyl-2-
Amides such as pyrrolidone, N-methylpyrrolidinone, hexamethyl phosphorotriamide; sulfoxides such as dimethyl sulfoxide, sulfolane; N-methylmorpholine, triethylamine, tripropylamine;
Tributylamine, diisopropylethylamine, dicyclohexylamine, N-methylpiperidine, pyridine, 4-pyrrolidinopyridine, picoline, 4- (N, N
Organic bases such as -dimethylamino) pyridine, 2,6-di (t-butyl) -4-methylpyridine, quinoline, N, N-dimethylaniline and N, N-diethylaniline.

The base to be used is not particularly limited as long as it is used as a base in a usual reaction. Preferably, N-methylmorpholine, triethylamine, tributylamine, diisopropylethylamine, dicyclohexylamine, N-methylpiperidine,
Pyridine, 4-pyrrolidinopyridine, picoline, 4-
(N, N-dimethylamino) pyridine, 2,6-di (te
rt-butyl) -4-methylpyridine, quinoline, N, N
Organic bases such as -dimethylaniline and N, N-diethylaniline.

Examples of the condensing agent used include (1)
Combinations of the above bases with phosphates such as diethylphosphoryl cyanide, diphenylphosphoryl azide, diethyl cyanophosphate; (ii) 1,3-dicyclohexylcarbodiimide, 1,3-diisopropylcarbodiimide,
Carbodiimides such as 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide; combinations of the carbodiimides with the following bases; the carbodiimides and N-hydroxysuccinimide, 1-hydroxybenzotriazole, N-hydroxy-5-norbornene −2,3-
A combination of N-hydroxys such as dicarboximide; (iii) 2,2′-dipyridyl disulfide;
(Iv) a combination of a disulfide such as 2,2'-dibenzothiazolyl disulfide and a phosphine such as triphenylphosphine or tributylphosphine;
N, N'-disuccinimidyl carbonate, di-2-
Carbonates such as pyridyl carbonate, S, S'-bis (1-phenyl-1H-tetrazol-5-yl) dithiocarbonate; (v) N, N'-bis (2
Phosphinic chlorides such as -oxo-3-oxazolidinyl) phosphinic chloride; (vi)
N, N'-disuccinimidyl oxalate, N, N '
-Diphthalimide oxalate, N, N'-bis (5-
Norbornene-2,3-dicarboxyimidyl) oxalate, 1,1′-bis (benzotriazolyl) oxalate, 1,1′-bis (6-chlorobenzotriazolyl) oxalate, 1,1′-bis Oxalates such as (6-trifluoromethylbenzotriazolyl) oxalate; (vii) phosphines and azodicarboxylic acid esters such as diethyl azodicarboxylate and 1,1 ′-(azodicarbonyl) dipiperidine or azolates (Viii) N-lower alkyl-5-arylisoxazolium such as N-ethyl-5-phenylisoxazolium-3'-sulfonate -3'-sulfonates; (ix) diheteroaryl diselenides such as di-2-pyridyl diselenide (X) arylsulfonyltriazolides such as p-nitrobenzenesulfonyltriazolide; (xi) 2-halo-1-lower alkylpyridinium halides such as 2-chloro-1-methylpyridinium iodide; ) 1,1'-
Imidazoles such as oxalyldiimidazole, N, N'-carbonyldiimidazole; (xiii) 3-lower alkyl-2-halogen-benzothia such as 3-ethyl-2-chloro-benzothiazolium fluoroborate (Xiv) 3-lower alkyl-benzothiazole-2-serones such as 3-methyl-benzothiazole-2-cellone; (xv) O-
(7-azabenzotriazol-1-yl) -N, N,
Phosphates such as N ', N'-tetramethylonium hexafluorophosphate (HATU), phenyldichlorophosphate, polyphosphate ester; (xvi) halogenosulfonyl isocyanates such as chlorosulfonyl isocyanate; (xvii) trimethylsilyl chloride, triethyl Halogenosilanes such as silyl chloride; (xviii) a combination of a lower alkane sulfonyl halide such as methanesulfonyl chloride and the above base; (xix) such as N, N, N ', N'-tetramethylchloroformamidium chloride N, N,
N ', N'-tetra-lower alkylhalogenoformamidium chlorides can be mentioned, and preferred are carbodiimides and a combination of phosphines and azodicarboxylic acid esters or azodicarboxamides.

The reaction temperature varies depending on the starting compound and the reaction reagent, but is carried out at -20 ° C to 80 ° C, preferably 0 ° C to room temperature.

The reaction time varies depending on the reaction temperature, the starting compound, the reaction reagent and the type of the solvent used, but is usually from 10 minutes to 3 days, preferably from 30 minutes to 1 day.
Days.

After completion of the reaction, the target compound of this reaction is obtained, for example, by concentrating the reaction mixture, adding an immiscible organic solvent such as water and ethyl acetate, washing with water, separating the organic layer containing the target compound, and adding anhydrous It is obtained by drying over magnesium sulfate or the like and then distilling off the solvent.

The obtained compound can be further purified, if necessary, by a conventional method, for example, recrystallization, silica gel column chromatography and the like. <2> When L is a leaving group: Examples of the solvent used include aliphatic hydrocarbons such as hexane and heptane;
Aromatic hydrocarbons such as benzene, toluene, xylene; methylene chloride, chloroform, carbon tetrachloride, dichloroethane, chlorobenzene, halogenated hydrocarbons such as dichlorobenzene; ethyl formate, ethyl acetate;
Esters such as propyl acetate, butyl acetate, diethyl carbonate; diethyl ether, diisopropyl ether,
Tetrahydrofuran, dioxane, dimethoxyethane,
Ethers such as diethylene glycol dimethyl ether; nitriles such as acetonitrile and isobutyronitrile; formamide, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-
Amides such as pyrrolidone, N-methylpyrrolidinone, hexamethyl phosphorotriamide; N-methylmorpholine, triethylamine, tripropylamine, tributylamine, diisopropylethylamine, dicyclohexylamine, N-methylpiperidine, pyridine, 4-
Pyrrolidinopyridine, picoline, 4- (N, N-dimethylamino) pyridine, 2,6-di (t-butyl) -4-
Organic bases such as methylpyridine, quinoline, N, N-dimethylaniline and N, N-diethylaniline can be mentioned, and ethers are preferred.

As the base used, for example, alkali metal carbonates such as sodium carbonate, potassium carbonate and lithium carbonate; alkali metal hydrogen carbonates such as sodium hydrogen carbonate, potassium hydrogen carbonate and lithium hydrogen carbonate; sodium methoxy , Sodium ethoxide, potassium methoxide, potassium ethoxide, potassium t-
Alkali metal alkoxides such as butoxide and lithium methoxide; N-methylmorpholine, triethylamine, tributylamine, diisopropylethylamine, dicyclohexylamine, N-methylpiperidine,
Pyridine, 4-pyrrolidinopyridine, picoline, 4-
(N, N-dimethylamino) pyridine, 2,6-di (te
rt-butyl) -4-methylpyridine, quinoline, N, N
Organic bases such as -dimethylaniline and N, N-diethylaniline can be mentioned, and preferred are organic bases. However, when the organic base is used as a solvent, it is not necessary to additionally use a base.

The reaction temperature varies depending on the starting compound and the reaction reagent, but is carried out at -20 ° C to 100 ° C, preferably 0 ° C to 50 ° C.

The reaction time varies depending on the reaction temperature, the starting compound, the reaction reagent or the type of the solvent used, but is usually from 10 minutes to 3 days, preferably from 30 minutes to 1 day.
2 hours.

After completion of the reaction, the target compound of this reaction is obtained, for example, by concentrating the reaction mixture, adding an immiscible organic solvent such as water and ethyl acetate, washing with water, separating the organic layer containing the target compound, and adding anhydrous It is obtained by drying over magnesium sulfate or the like and then distilling off the solvent.

The obtained compound can be further purified, if necessary, by a conventional method, for example, recrystallization, silica gel column chromatography and the like. (Seventh Step) This step is a step of reacting compound (8) with compound (9) in an inert solvent to produce compound (2).

Solvents used include, for example, aliphatic hydrocarbons such as hexane, heptane, ligroin and petroleum ether; aromatic hydrocarbons such as benzene, toluene and xylene; methylene chloride, chloroform,
Halogenated hydrocarbons such as carbon tetrachloride, dichloroethane, chlorobenzene, dichlorobenzene; ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, dimethoxyethane, diethylene glycol dimethyl ether; methano-
, Ethanol, n-propanol, isopropanol
, N-butanol, isobutanol, t-butanol
Alcohols such as toluene, isoamyl alcohol, diethylene glycol, glycerin, octanol, cyclohexanol and methyl cellosolve; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone and cyclohexanone; nitros such as nitroethane and nitrobenzene Compounds; acetonitrile,
Nitriles such as isobutyronitrile can be mentioned, and are preferably alcohols.

The reaction temperature varies depending on the starting compound, but is carried out at 0 ° C. to 150 ° C., preferably 20 ° C. to 100 ° C.

The reaction time varies depending on the reaction temperature, the starting compound, the reaction reagent or the type of the solvent used, but is usually 10 minutes to 3 days, preferably 30 minutes to 2 days.
4 hours.

After completion of the reaction, the target compound of this reaction is obtained, for example, by concentrating the reaction mixture, adding an immiscible organic solvent such as water and ethyl acetate, washing with water, separating the organic layer containing the target compound, and adding anhydrous It is obtained by drying over magnesium sulfate or the like and then distilling off the solvent.

The obtained compound can be further purified, if necessary, by a conventional method, for example, recrystallization, silica gel column chromatography and the like. (Eighth Step) This step is a step of reacting compound (10) with a halogenating reagent in an inert solvent in the presence of an acid or base to produce compound (2). <1> When the reaction is performed in the presence of an acid: Examples of the solvent used include water; aliphatic hydrocarbons such as hexane, heptane, ligroin, and petroleum ether; aromatic hydrocarbons such as benzene, toluene, and xylene. Hydrogens: methylene chloride, chloroform, carbon tetrachloride, dichloroethane,
Halogenated hydrocarbons such as chlorobenzene and dichlorobenzene; ethyl formate, ethyl acetate, propyl acetate;
Esters such as butyl acetate and diethyl carbonate; ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, dimethoxyethane and diethylene glycol dimethyl ether; such as acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone and cyclohexanone Examples of suitable ketones include water.

Examples of the acid used include inorganic acids such as hydrochloric acid, hydrobromic acid, sulfuric acid, perchloric acid and phosphoric acid, or acetic acid, formic acid, oxalic acid, methanesulfonic acid, p-toluenesulfonic acid, camphorsulfonic acid. Examples thereof include acids, organic acids such as trifluoroacetic acid, and trifluoromethanesulfonic acid, and are preferably inorganic acids.

Examples of the halogenating reagent to be used include halogen molecules such as chlorine, bromine and iodine; thionyl halides such as thionyl chloride, thionyl bromide and thionyl iodide; sulfuryl chloride, sulfuryl bromide and sulfuryl iodide. Sulfuryl halides such as N-bromosuccinylimide, N-
N-halogenated imides such as chlorosuccinylimide can be mentioned, and are preferably halogen molecules.

The reaction temperature varies depending on the starting compound, solvent and acid catalyst used, but is usually from 0 ° C to 100 ° C, preferably from 50 ° C to 80 ° C.

The reaction time varies depending on the used starting compound, solvent, acid catalyst and reaction temperature, but is usually 5 minutes to 8 hours, preferably 10 minutes to 3 hours.

After completion of the reaction, the target compound of this reaction is obtained, for example, by concentrating the reaction mixture, adding an immiscible organic solvent such as water and ethyl acetate, washing with water, separating the organic layer containing the target compound, and adding anhydrous It is obtained by drying over magnesium sulfate or the like and then distilling off the solvent.

The obtained compound can be further purified, if necessary, by a conventional method, for example, recrystallization, silica gel column chromatography and the like. <2> When the reaction is performed in the presence of a base: When the reaction is performed in the presence of a base, the reaction is performed in (a) an enolization step and (b) a halogenation step. (A) Enolization step Examples of the solvent used include, for example, aliphatic hydrocarbons such as hexane, heptane, ligroin and petroleum ether; aromatic hydrocarbons such as benzene, toluene and xylene; diethyl ether; Diisopropyl ether,
Tetrahydrofuran, dioxane, dimethoxyethane,
Ethers such as diethylene glycol dimethyl ether can be mentioned, and ethers are preferred.

Examples of the base used include alkali metal hydrides such as lithium hydride, sodium hydride and potassium hydride; and sodium hydroxide, potassium hydroxide, barium hydroxide and lithium hydroxide. Alkali metal hydroxides; alkali metal alkoxides such as sodium methoxide, sodium ethoxide, potassium methoxide, potassium ethoxide, potassium t-butoxide, lithium methoxide; butyllithium, lithium diisopropylamide, lithium bis (trimethylsilyl) ) Organometallic bases, such as amides, are preferred.

The reaction temperature varies depending on the starting compound, solvent and base catalyst used, but is usually from -100 ° C to 0 ° C.
° C, preferably -80 ° C to -20 ° C.

The reaction time varies depending on the starting compound, solvent, base catalyst and reaction temperature used, but is usually 1 minute to 3 hours, preferably 10 minutes to 1 hour.

After completion of the reaction, the enol compound is used as it is for halogenation in a solution or, if desired, silylated with a silylating reagent such as trimethylsilyl chloride.
After neutralization with a base such as saturated ammonium chloride, add an immiscible organic solvent such as water and ethyl acetate, wash with water, separate the organic layer containing the target compound, dry over anhydrous magnesium sulfate, etc. Obtained by leaving. (B) Halogenation As the solvent to be used, when the enol compound is used as a solution, the solvent used at the time of enolization is used as it is, and when it is silylated, for example, hexane, heptane, ligroin, Aliphatic hydrocarbons such as petroleum ether; aromatic hydrocarbons such as benzene, toluene and xylene; diethyl ether, diisopropyl ether,
Tetrahydrofuran, dioxane, dimethoxyethane,
Ethers such as diethylene glycol dimethyl ether can be mentioned, and ethers are preferred.

As the halogenating reagent, for example, chlorine,
Halogen molecules such as bromine and iodine; thionyl halides such as thionyl chloride, thionyl bromide and thionyl iodide; sulfuryl halides such as sulfuryl chloride, sulfuryl bromide and sulfuryl iodide; N-bromosuccinylimide, N-chloro Examples include N-halogenated imides such as succinylimide, and preferred are halogen molecules.

The reaction temperature depends on the starting compound, solvent and base catalyst used, but is usually from -20 ° C to 50 ° C.
° C, preferably -10 ° C to 20 ° C.

The reaction time varies depending on the starting compound, solvent, base catalyst and reaction temperature used, but is usually 30 minutes to 36 hours, preferably 1 hour to 18 hours.

After completion of the reaction, the target compound of this reaction is obtained, for example, by concentrating the reaction mixture, adding an immiscible organic solvent such as water and ethyl acetate, washing with water, separating the organic layer containing the target compound, and adding anhydrous It is obtained by drying over magnesium sulfate or the like and then distilling off the solvent.

The obtained compound can be further purified, if necessary, by a conventional method, for example, recrystallization, silica gel column chromatography and the like. (Method E) (Ninth Step) This step is a step of reacting compound (6) with compound (11) in an inert solvent to produce compound (10a).

The compound (10a) is the same as the compound (1)
0) a compound R ⁴ a is a hydrogen atom.

Examples of the solvent used include aliphatic hydrocarbons such as hexane, heptane, ligroin and petroleum ether; aromatic hydrocarbons such as benzene, toluene and xylene; methylene chloride, chloroform,
Halogenated hydrocarbons such as carbon tetrachloride, dichloroethane, chlorobenzene, dichlorobenzene; ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, dimethoxyethane, diethylene glycol dimethyl ether; methano-
, Ethanol, n-propanol, isopropanol
, N-butanol, isobutanol, t-butanol
Alcohols such as toluene, isoamyl alcohol, diethylene glycol, glycerin, octanol, cyclohexanol and methyl cellosolve; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone and cyclohexanone; nitros such as nitroethane and nitrobenzene Compounds; acetonitrile,
Nitriles such as isobutyronitrile can be mentioned, and are preferably alcohols.

The reaction temperature varies depending on the starting compound and the base, but is usually from 0 ° C. to 150 ° C., preferably from 50 ° C.
C. to 100.degree.

The reaction time varies depending on the reaction temperature, the starting compound, the reaction reagent and the type of the solvent used, but is usually 1 hour to 3 days, preferably 5 hours to 24 hours.

After completion of the reaction, the target compound of this reaction is obtained, for example, by concentrating the reaction mixture, adding an immiscible organic solvent such as water and ethyl acetate, washing with water, separating the organic layer containing the target compound, and adding anhydrous It is obtained by drying over magnesium sulfate or the like and then distilling off the solvent.

The obtained compound can be further purified, if necessary, by a conventional method, for example, recrystallization, silica gel column chromatography and the like.

The compound (2) can be produced by performing the method in the above-mentioned eighth step using the compound (10a) obtained in this step.

The hydrogen atom on the imidazole ring in the compound (10a) can be halogenated or nitrated, and the obtained nitro compound can be reduced to produce an amino compound. Can be alkylated, acylated, etc. to produce the compound (10). (Method F) (Tenth Step) This step is a step of reacting compound (6) with compound (12) in an inert solvent in the presence of a base to produce compound (13).

This step can be performed according to the ninth step.

When R ⁴ b is an alkoxy group, R ⁴ b may be converted to a hydroxyl group in this step. (Eleventh Step) In this step, compound (1) is prepared in an inert solvent.
This is a step of producing compound (14) by reacting 3) with N, O-dimethylhydroxylamine.

This step comprises the steps of (a) hydrolysis and (b) amidation. (A) Hydrolysis The solvent used is, for example, water; esters such as ethyl formate, ethyl acetate, propyl acetate, butyl acetate, and diethyl carbonate; diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, and dimethoxy. Ethers such as ethane and diethylene glycol dimethyl ether; methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, t-butanol, isoamyl alcohol Alcohols such as diethylene glycol, glycerin, octanol, cyclohexanol and methyl cellosolve; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone and cyclohexanone; nitriles such as acetonitrile and isobutyronitrile , Formamide, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-
Amides such as pyrrolidone, N-methylpyrrolidinone, and hexamethyl phosphorotriamide; and sulfoxides such as dimethyl sulfoxide and sulfolane are preferable, and alcohols are preferable. As the base used, for example, sodium carbonate, potassium carbonate,
Alkali metal carbonates such as lithium carbonate; alkali metal bicarbonates such as sodium bicarbonate, potassium bicarbonate and lithium bicarbonate; alkali metals such as sodium hydroxide, potassium hydroxide, barium hydroxide and lithium hydroxide Hydroxides; alkali metal alkoxides such as sodium methoxide, sodium ethoxide, potassium methoxide, potassium ethoxide, potassium t-butoxide, and lithium methoxide; preferably alkali metal oxides It is.

The reaction temperature varies depending on the starting compound and solvent used, but is usually from 0 ° C. to 100 ° C., preferably from 20 ° C. to 80 ° C.

The reaction time varies depending on the starting compound used, the solvent and the reaction temperature, but is usually 30 minutes to 24 hours, preferably 1 hour to 8 hours.

After completion of the reaction, the hydrolyzed target compound is obtained as a salt with a base by, for example, concentrating the reaction mixture and recrystallizing the residue, or concentrating the reaction solution after neutralizing it. By recrystallizing the residue, the target compound,
Alternatively, it is obtained as a salt with an acid. However, it can be obtained as a salt with an acid only when the target compound has a basic group.

The obtained compound can be further purified, if necessary, by a conventional method, for example, recrystallization, silica gel column chromatography and the like. (B) Amidation As the solvent used, for example, diethyl ether,
Ethers such as diisopropyl ether, tetrahydrofuran, dioxane, dimethoxyethane, diethylene glycol dimethyl ether; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone and cyclohexanone; nitro compounds such as nitroethane and nitrobenzene; acetonitrile , Nitrites such as isobutyronitrile; formamide,
Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, N-methylpyrrolidinone, hexamethylphosphorotriamide; sulfoxides such as dimethyl sulfoxide, sulfolane; Methyl morpholine, triethylamine, tripropylamine, tributylamine, diisopropylethylamine, dicyclohexylamine, N-
Methylpiperidine, pyridine, 4-pyrrolidinopyridine, picoline, 4- (N, N-dimethylamino) pyridine, 2,6-di (t-butyl) -4-methylpyridine,
Organic bases such as quinoline, N, N-dimethylaniline and N, N-diethylaniline can be mentioned.

The base to be used is not particularly limited as long as it is used as a base in a usual reaction. Preferably, N-methylmorpholine, triethylamine, tributylamine, diisopropylethylamine, dicyclohexylamine, N-methylpiperidine,
Pyridine, 4-pyrrolidinopyridine, picoline, 4-
(N, N-dimethylamino) pyridine, 2,6-di (te
rt-butyl) -4-methylpyridine, quinoline, N, N
Organic bases such as -dimethylaniline and N, N-diethylaniline can be used. Examples of the condensing agent used include (1) phosphoric esters such as diethylphosphoryl cyanide, diphenylphosphoryl azide and diethyl cyanophosphate (Ii) 1,3-dicyclohexylcarbodiimide,
1,3-diisopropylcarbodiimide, 1-ethyl-
Carbodiimides such as 3- (3-dimethylaminopropyl) carbodiimide; combinations of the carbodiimides with the following bases; the carbodiimides and N-hydroxysuccinimide, 1-hydroxybenzotriazole, N-
Combinations of N-hydroxys such as hydroxy-5-norbornene-2,3-dicarboximide; (iii)
A combination of disulfides such as 2,2'-dipyridyl disulfide and 2,2'-dibenzothiazolyl disulfide and phosphines such as triphenylphosphine and tributylphosphine; (iv) N, N'-disc Carbonates such as cinimidyl carbonate, di-2-pyridyl carbonate, S, S'-bis (1-phenyl-1H-tetrazol-5-yl) dithiocarbonate; (v) N, N'-bis ( 2-oxo-3
-Oxazolidinyl) phosphinic chlorides such as phosphinic chloride; (vi) N, N'-disuccinimidyl oxalate, N, N'-diphthalimido oxalate, N, N'-bis (5 -Norbornene-
2,3-dicarboxyimidyl) oxalate, 1,
1′-bis (benzotriazolyl) oxalate, 1,
Oxalates such as 1'-bis (6-chlorobenzotriazolyl) oxalate and 1,1'-bis (6-trifluoromethylbenzotriazolyl) oxalate;
(Vii) a combination of the phosphine and an azodicarboxylic acid ester such as diethyl azodicarboxylate and 1,1 ′-(azodicarbonyl) dipiperidine or an azodicarboxamide; a combination of the phosphine and the base; (viii) ) N-Lower alkyl-, such as N-ethyl-5-phenylisoxazolium-3'-sulfonate
5-arylisoxazolium-3′-sulfonates; (ix) diheteroaryldiselenides such as di-2-pyridyldiselenide; (x) aryl such as p-nitrobenzenesulfonyltriazolide (Xi) 2-halo-1-lower alkylpyridinium halides such as 2-chloro-1-methylpyridinium iodide; (xii) 1,1′-oxalyldiimidazole, N, N ′ -Imidazoles such as carbonyldiimidazole; (xiii) 3-ethyl-2-
3-lower alkyl-2-halogen-benzothiazolium fluoroborates, such as chloro-benzothiazolium fluoroborate; (xiv) 3-lower alkyl-benzo, such as 3-methyl-benzothiazol-2-serone (Xv) O- (7-azabenzotriazol-1-yl) -N, N, N ', N'
Phosphates such as tetramethylonium hexafluorophosphate (HATU), phenyldichlorophosphate, polyphosphate esters; (xvi)
(Xvii) halogenosilanes such as trimethylsilyl chloride and triethylsilyl chloride; (xviii) a combination of a lower alkanesulfonyl halide such as methanesulfonyl chloride and the above base;
(Xix) N, N, N ', N'-tetra-lower alkylhalogenoformamidium chlorides such as N, N, N', N'-tetramethylchloroformamidium chloride can be mentioned, but it is preferable. Are carbodiimides and combinations of phosphines with azodicarboxylic acid esters or azodicarboxamides.

The reaction temperature varies depending on the starting compounds and the reaction reagents, but it is usually from -20 ° C to 80 ° C, preferably from 0 ° C to room temperature.

The reaction time varies depending on the reaction temperature, the starting compound, the reaction reagent and the type of the solvent used, but is usually from 10 minutes to 3 days, preferably from 30 minutes to 1 day.
Days.

After completion of the reaction, the target compound of this reaction is obtained, for example, by concentrating the reaction mixture, adding an immiscible organic solvent such as water and ethyl acetate, washing with water, separating the organic layer containing the target compound, and adding anhydrous It is obtained by drying over magnesium sulfate or the like and then distilling off the solvent.

The obtained compound can be further purified, if necessary, by a conventional method, for example, recrystallization, silica gel column chromatography and the like. (Twelfth Step) In this step, compound (1) is prepared in an inert solvent.
This is a step of reacting 4) with compound (15) to produce compound (10b).

The compound (10b) is the same as the compound (1)
R ⁴ a 0) is a compound which is R ⁴ b.

Examples of the solvent used include aliphatic hydrocarbons such as hexane, heptane, ligroin and petroleum ether; aromatic hydrocarbons such as benzene, toluene and xylene; diethyl ether and diisopropyl ether. Ethers such as ter, tetrahydrofuran, dioxane, dimethoxyethane and diethylene glycol dimethyl ether can be mentioned, and ethers are preferred.

The reaction temperature varies depending on the starting compounds and the reaction reagents, but it is usually from -100 ° C to 20 ° C, preferably from -80 ° C to 0 ° C.

The reaction time varies depending on the reaction temperature, the starting compound, the reaction reagent and the type of the solvent used, but is usually 10 minutes to 3 days, preferably 30 minutes to 8 days.
Time.

After completion of the reaction, the target compound of this reaction is obtained, for example, by concentrating the reaction mixture, adding an immiscible organic solvent such as water and ethyl acetate, washing with water, separating the organic layer containing the target compound, and adding anhydrous It is obtained by drying over magnesium sulfate or the like and then distilling off the solvent.

The obtained compound can be further purified, if necessary, by a conventional method, for example, recrystallization, silica gel column chromatography and the like. Compound (1) obtained in this step
Compound (2) can be produced by carrying out the method of the above-mentioned eighth step using Ob).

The compounds (3) and (4) as starting materials for producing the compound (1) of the present invention are known or can be produced by the following G to J methods. (G method)

[0139]

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(Method H)

[0141]

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(Method I)

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(J method)

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<Method G> (Thirteenth step) In this step, compound (1) was prepared in an inert solvent.
In this step, compound (17) is reacted with compound (6) to produce compound (18).

Examples of the solvent used include halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, dichloroethane, chlorobenzene, and dichlorobenzene; ethyl formate, ethyl acetate, propyl acetate, butyl acetate, and diethyl carbonate. Esters such as diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, dimethoxyethane, diethylene glycol dimethyl ether; methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, t-butanol
Alcohols such as toluene, isoamyl alcohol, diethylene glycol, glycerin, octanol, cyclohexanol and methyl cellosolve; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone and cyclohexanone; acetonitrile and isobutyronitrile Such nitriles; formamide,
Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, N-methylpyrrolidinone, and hexamethylphosphorotriamide can be mentioned, and ketones are preferred. .

The reaction temperature varies depending on the starting compound, but is carried out at 0 ° C to 100 ° C, preferably 20 ° C to 80 ° C.

The reaction time varies depending on the reaction temperature, the starting compound, the reaction reagent or the type of the solvent used, but is usually 1 hour to 5 days, preferably 8 hours to 3 days.

After completion of the reaction, the target compound of this reaction is obtained, for example, by concentrating the reaction mixture, adding an immiscible organic solvent such as water and ethyl acetate, washing with water, separating the organic layer containing the target compound, and adding anhydrous It is obtained by drying over magnesium sulfate or the like and then distilling off the solvent.

The obtained compound can be further purified, if necessary, by a conventional method, for example, recrystallization, silica gel column chromatography and the like. (Step 14) In this step, compound (1) is prepared in an inert solvent.
This is a step of producing compound (3) by hydrolyzing 8).

Examples of the solvent used include water; esters such as ethyl formate, ethyl acetate, propyl acetate, butyl acetate and diethyl carbonate; diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, dimethoxyethane, and the like. Ethers such as diethylene glycol dimethyl ether; methanol, ethanol
Alcohols such as toluene, n-propanol, isopropanol, n-butanol, isobutanol, t-butanol, isoamyl alcohol, diethylene glycol, glycerin, octanol, cyclohexanol and methyl cellosolve Ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone and cyclohexanone; nitriles such as acetonitrile, isobutyronitrile; formamide, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl Amides such as -2-pyrrolidone, N-methylpyrrolidinone, and hexamethylphosphorotriamide; and sulfoxides such as dimethyl sulfoxide and sulfolane, and alcohols are preferable. Examples of the base used include alkali metal carbonates such as sodium carbonate, potassium carbonate and lithium carbonate; alkali metal bicarbonates such as sodium hydrogen carbonate, potassium hydrogen carbonate and lithium hydrogen carbonate; sodium hydroxide, water Alkali metal hydroxides such as potassium oxide, barium hydroxide and lithium hydroxide; alkali metal alkoxides such as sodium methoxide, sodium ethoxide, potassium methoxide, potassium ethoxide, potassium t-butoxide and lithium methoxide And preferred are alkali metal oxides.

The reaction temperature varies depending on the starting compound and solvent used, but is usually from 0 ° C. to 100 ° C., preferably from 20 ° C. to 80 ° C.

The reaction time varies depending on the starting compound used, the solvent and the reaction temperature, but is usually 30 minutes to 24 hours, preferably 1 hour to 8 hours.

After completion of the reaction, the target compound of this reaction is obtained, for example, by concentrating the reaction mixture, adding an immiscible organic solvent such as water and ethyl acetate, washing with water, separating the organic layer containing the target compound, and adding anhydrous It is obtained by drying over magnesium sulfate or the like and then distilling off the solvent.

The obtained compound can be further purified, if necessary, by a conventional method, for example, recrystallization, silica gel column chromatography and the like. (Method H) (Step 15) In this step, compound (1) is prepared in an inert solvent.
In this step, compound (19) is reacted with 6) to produce compound (20).

This step is performed in the same manner as in the thirteenth step. (Sixteenth Step) The present step is carried out by reacting the compound (2) in an inert solvent.
In this step, compound (4) is produced by hydrolyzing compound (0).

This step is performed in the same manner as the fourteenth step. (Method I) (Seventeenth step) The present step was carried out by reacting the compound (2)
In this step, compound (17) is reacted with 1) to produce compound (3).

Examples of the solvent used include water; esters such as ethyl formate, ethyl acetate, propyl acetate, butyl acetate and diethyl carbonate; diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, dimethoxyethane, and the like. Ethers such as diethylene glycol dimethyl ether; methanol, ethanol
Alcohols such as toluene, n-propanol, isopropanol, n-butanol, isobutanol, t-butanol, isoamyl alcohol, diethylene glycol, glycerin, octanol, cyclohexanol and methyl cellosolve Ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone and cyclohexanone; formamide, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, N-methylpyrrolidinone, hexamethyl Examples include amides such as phosphorotriamide; sulfoxides such as dimethyl sulfoxide and sulfolane, and are preferably alcohols or water.

The reaction temperature varies depending on the starting compounds and the reaction reagents, but it is from 50 ° C. to 150 ° C., preferably from 80 ° C. to 100 ° C.

The reaction time varies depending on the reaction temperature, the starting compound, the reaction reagent and the kind of the solvent used, but is usually 5 hours to 3 days, preferably 10 hours to 20 days.
Time.

After completion of the reaction, the desired compound (4)
Can be obtained, for example, by concentrating the reaction mixture, finely pulverizing the obtained crystals, and washing with, for example, an organic solvent such as ether or hexane. (Method J) (Eighteenth step) The present step is to carry out the compound (2
This is a step of reacting 1) with compound (19) to produce compound (3).

This step is performed in the same manner as the seventeenth step.

Examples of the dosage form of the compound (1) of the present invention include oral administration such as tablets, capsules, granules, powders or syrups, and parenteral administration such as injections or suppositories. These preparations include excipients (eg, sugar derivatives such as lactose, sucrose, glucose, mannitol, sorbitol; starch derivatives such as corn starch, potato starch, α-starch, dextrin; cellulose derivatives such as crystalline cellulose). Gum arabic; dextran; organic excipients such as pullulan: and silicate derivatives such as light anhydrous silicic acid, synthetic aluminum silicate, calcium silicate, magnesium metasilicate aluminate; phosphates such as calcium hydrogen phosphate; Carbonates such as calcium carbonate; sulfates such as calcium sulfate Mechanical excipients), lubricants (eg, stearic acid, metal salts of stearic acid such as calcium stearate, magnesium stearate; talc; colloidal silica; waxes such as veegum, gay wax). Boric acid; adipic acid; sulfates such as sodium sulfate; glycol; fumaric acid; sodium benzoate; DL leucine; fatty acid sodium salts; lauryl sulfates such as sodium lauryl sulfate and magnesium lauryl sulfate; And binders (eg, hydroxypropylcellulose, hydroxypropylmethylcellulose, polyvinylpyrrolidone, macrogol, and compounds similar to the above-mentioned excipients). And disintegrants (eg, For example, cellulose derivatives such as low-substituted hydroxypropylcellulose, carboxymethylcellulose, carboxymethylcellulose calcium, internally crosslinked sodium carboxymethylcellulose; carboxymethyl starch;
Examples include chemically modified starch and cellulose such as sodium carboxymethyl starch and cross-linked polyvinyl pyrrolidone. ), Stabilizers (paraoxybenzoic acid esters such as methylparaben and propylparaben; alcohols such as chlorobutanol, benzyl alcohol and phenylethyl alcohol; benzalkonium chloride; phenols such as phenol and cresol; thimerosal; Acetic acid; and sorbic acid), flavoring agents (for example, commonly used sweeteners, sour agents, flavors, and the like), and additives such as diluents. It is manufactured by a well-known method.

The dosage varies depending on the condition, age, method of administration, etc. For example, in the case of oral administration,
As a lower limit, 0.01 mg / kg body weight (preferably,
0.1 mg / kg body weight), 100 mg / k as upper limit
g body weight (preferably 10 mg / kg body weight), in the case of intravenous administration, 0.001 m
g / kg body weight (preferably 0.01 mg / kg body weight), up to 10 mg / kg body weight (preferably
1 mg / kg body weight) is desirably administered once or several times a day depending on the symptoms.

Hereinafter, the present invention will be described in detail with reference to Examples.

[0167]

EXAMPLES The apparatus for measuring various analytical data and the measurement conditions for liquid chromatography are described below. (Measurement conditions for liquid chromatography and mass spectrometry)
As a measuring device for liquid chromatography-mass spectrometry, HP-1100 LC / MSD manufactured by Hewlett-Packard Company was used. The measurement conditions of the normal layer system (N) are described. The column is Wakosil 5CN, 4.0 mm x 150 m, manufactured by Wako Pure Chemical Industries, Ltd.
m was used. The analysis conditions were a column temperature of 25 ° C., and hexane and isopropanol (containing 0.5% acetic acid) were used as a moving layer. The flow rate was 1.5 ml / min, and isopropanol (containing 5% acetic acid) was a linear gradient from 5% to 90% for 10 minutes. Atmospheric pressure chemical ionization (APCI) was used in the mass spectrometer. The measurement conditions of the reverse layer system (R) are described. The column is CD-C18 manufactured by Intact.
It was used. The analysis conditions were a column temperature of 40 ° C., and acetonitrile and water (containing 0.01% trifluoroacetic acid) as a moving layer. The flow rate was 1.5 ml / min and acetonitrile was a linear gradient from 8% to 99% for 10 minutes. Atmospheric pressure chemical ionization (APCI) was used in the mass spectrometer. In the text, normal system is (N)
The reverse layer system was described as (R). FAB mass spectrum and EI mass spectrum are JE as other mass spectra.
It was measured with an OL JMS-D 300 measuring device. (A device for measuring a nuclear magnetic resonance spectrum (hereinafter, 1H-NMR)) 1H-NMR data is JEOLJNM-GX270
FT-NMR or Varian Mercury 4
00 Measured with a measuring device. The chemical shift value is described in δ ppm using tetramethylsilane as a reference substance. The fission pattern is indicated by s for singlet, d for doublet, t for triplet, q for quadruple, and sep for heptaline. Example 1 [4- (2-Methyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl]-(4-trifluoromethyl-phenyl) -amine 2-bromo- 900 mg (3.56 mmol) of 1- (2-methyl-imidazo [1,2-α] pyridin-3-yl) -ethanone (Reference Example 56) and (4-trifluoromethyl-phenyl) -thiourea (Reference Example) 2) 822 mg (3.56 mmol) of ethanol was dissolved in 50 ml of ethanol, and the mixture was refluxed for 16 hours. Ethyl acetate was added to the reaction solution, and the mixture was washed with a saturated aqueous solution of sodium hydrogen carbonate and saturated saline. After the organic layer was dried over anhydrous sodium sulfate, the solvent was concentrated under reduced pressure, and the obtained crystals were finely pulverized and washed with hexane-ethyl acetate to give the title compound 1.
29 g (97%) were obtained.

Mp 278-282 ° C .; 1H-NMR (DMSO-d6) δ: 10.86 (s, 1H), 8.87 (d, 1H, J
= 7.0Hz), 7.85 (d, 2H, J = 8.6Hz), 7.68 (d, 2H, J = 8.6
Hz), 7.55 (d, 1H, J = 9.2Hz), 7.31-7.26 (m, 1H), 7.22
(s, 1H), 7.02-6.97 (m, 1H), 2.54 (s, 3H); MS (APCI, m / z): 375 (M + H) +; HPLC (N): Rt = 4.5 min. Example 2) [4- (2-Methyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -p-tolyl-amine p-tolyl-thiourea (purchased from Tokyo Chemical Industry) And the reaction was carried out in the same manner as in Example 1 to obtain the title compound.

Mp 229-231 ° C .; 1H-NMR (DMSO-d6) δ: 10.30 (s, 1H), 8.95 (d, 1H, J
= 7.0Hz), 7.57-7.52 (m, 3H), 7.32-7.28 (m, 1H), 7.1
4 (d, 2H, J = 8.3Hz), 7.07 (s, 1H), 7.00-6.97 (m, 1
H), 2.53 (s, 3H), 2.26 (s, 3H); MS (APCI, m / z): 321 (M + H) +; HPLC (N): Rt = 5.2 min. (Example 3) (Example 3) 4-methoxy-phenyl)-[4- (2-methyl-imidazo [1,2-
Using [α] pyridin-3-yl) -thiazol-2-yl] -amine (4-methoxy-phenyl) -thiourea (Reference Example 3), the reaction was carried out in the same manner as in Example 1 to obtain the title compound. .

Mp 214-217 ° C .; 1H-NMR (DMSO-d6) δ: 8.95 (d, 1H, J = 6.8 Hz), 7.58-
7.52 (m, 3H), 7.30-7.24 (m, 1H), 7.02-6.84 (m, 5
H), 3.73 (s, 3H), 2.53 (s, 3H); MS (EI, m / z): 336 (M) +. (Example 4) [4- (2-methyl-imidazo [1,2 The reaction was carried out in the same manner as in Example 1 using -α] pyridin-3-yl) -thiazol-2-yl] -phenyl-amine phenylthiourea to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.41 (s, 1H), 8.
94 (d, 1H, J = 6.7Hz), 7.65 (d, 2H, J = 7.4Hz), 7.55
(d, 1H, J = 8.8Hz), 7.34 (t, 2H, J = 7.6Hz), 7.29 (t,
1H, J = 7.3Hz), 7.10 (s, 1H), 6.98 (t, 2H, J = 7.3Hz),
2.54 (s, 3H); MS (APCI, m / z): 307 (M + H) +; HPLC (N): Rt = 5.5 min. (Example 5) [4- (2-methyl-imidazo [1 , 2-α] pyridin-3-yl) -thiazol-2-yl] -o-tolyl-amine Using m-tolyl-thiourea, the reaction was carried out in the same manner as in Example 1 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 9.49 (s, 1H), 8.9
6 (d, 1H, J = 7.4Hz), 7.92-7.88 (m, 1H), 7.53 (d, 1
H, J = 8.9Hz), 7.28-7.20 (m, 3H), 7.05-7.01 (m, 2H),
6.95-6.91 (m, 1H), 2.52 (s, 3H), 2.31 (s, 3H); MS (APCI, m / z): 321 (M + H) +; HPLC (N): Rt = 4.8 min. Example 6 Ethyl- [4- (2-methyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -amine Same as Example 1 using ethylthiourea. The reaction was performed to obtain the title compound.

MS (APCI, m / z): 259 (M + H) +; HPLC (N): Rt = 5.0 min. (Example 7) (2-chloro-phenyl)-[4- (2-methyl -Imidazo [1,2-α]
The reaction was carried out in the same manner as in Example 1 using (pyridin-3-yl) -thiazol-2-yl] -amine (2-chloro-phenyl) -thiourea to obtain the title compound.

1H-NMR (CDCl3) δ: 8.92 (dd, 1H, J = 1.4
Hz, 6.0Hz), 8.21 (dd, 1H, J = 1.4Hz, 8.1Hz), 7.67
(s, 1H), 7.57 (dd, 1H, J = 1.3Hz, 8.3Hz), 7.44 (dd,
1H, J = 1.3Hz, 8.0Hz), 7.34-7.27 (m, 1H), 7.22-7.18
(m, 1H), 7.01 (dt, 1H, J = 1.4Hz, 8.0Hz), 6.83-6.80
(m, 1H), 6.76 (s, 1H), 2.65 (s, 3H); MS (APCI, m / z): 341 (M + H) +, 343 (M + H) +; HPLC (N): Rt = 4.8 min. (Example 8) Methyl- [4- (2-methyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -amine Performed using methylthiourea. The reaction was carried out in the same manner as in Example 1 to obtain the title compound.

MS (APCI, m / z): 245 (M + H) +; HPLC (N): Rt = 5.7 min. (Example 9) (2-methoxy-phenyl)-[4- (2-methyl -Imidazo [1,2-
The reaction was carried out in the same manner as in Example 1 using α] pyridin-3-yl) -thiazol-2-yl] -amine (2-methoxy-phenyl) -thiourea to obtain the title compound.

1H-NMR (DMSO-d6) δ: 9.71 (s, 1H), 8.9
4 (d, 1H, J = 6.5Hz), 8.28-8.25 (m, 1H), 7.54 (d, 1
H, J = 8.9Hz), 7.27 (t, 1H, J = 8.6Hz), 7.07-6.92 (m,
5H), 3.88 (s, 3H), 2.53 (s, 3H); MS (APCI, m / z): 337 (M + H) +; HPLC (N): Rt = 5.8 min. (Example 10) 3,4-dimethoxy-phenyl)-[4- (2-methyl-imidazo [1,
Using 2-α] pyridin-3-yl) -thiazol-2-yl] -amine (3,4-dimethoxy-phenyl) -thiourea, the reaction was carried out in the same manner as in Example 1 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.22 (s, 1H), 9.
01 (d, 1H, J = 6.9Hz), 7.55-7.51 (m, 2H), 7.29-7.26
(m, 1H), 7.02-6.89 (m, 4H), 3.73 (s, 3H), 3.72 (s,
3H), 2.53 (s, 3H); MS (APCI, m / z): 367 (M + H) +; HPLC (N): Rt = 6.7 min. (Example 11) (3,5-dimethoxy-phenyl) )-[4- (2-Methyl-imidazo [1,
2-α] pyridin-3-yl) -thiazol-2-yl] -amine (3,5-dimethoxy-phenyl) -thiourea (Reference Example 47)
And the reaction was carried out in the same manner as in Example 1 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.40 (s, 1H), 8.
98 (d, 1H, J = 6.8Hz), 7.54 (d, 1H, J = 8.9Hz), 7.26
(t, 1H, J = 6.8Hz), 7.09 (s, 1H), 6.95-6.89 (m, 3H),
6.14 (t, 1H, J = 2.2Hz), 3.71 (s, 6H), 2.53 (s, 3H); MS (APCI, m / z): 367 (M + H) +; HPLC (N): Rt = 5.4 min. (Example 12) [4- (2-Methyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl]-(4-propyl-phenyl) -amine (4- Example 1 using propyl-phenyl) -thiourea
The reaction was carried out in the same manner as in to give the title compound.

1H-NMR (DMSO-d6) δ: 10.30 (s, 1H), 8.
95 (d, 1H, J = 7.0Hz), 7.54 (d, 3H, J = 8.4Hz), 7.26
(dt, 1H, J = 1.4Hz, 6.8Hz), 2.53 (s, 3H), 2.53-2.48
(m, 2H), 1.64-1.50 (m.2H), 0.89 (t, 3H, J = 7.3Hz); MS (APCI, m / z): 349 (M + H) +; HPLC (N): Rt = 4.4 min. (Example 13) N- [4- [4- (2-methyl-imidazo [1,2-α] pyridin-3-yl)
-Thiazol-2-ylamino] -phenyl] -acetamide Using N- (4-thioureido-phenyl) -acetamide, the reaction was carried out in the same manner as in Example 1 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.31 (s, 1H), 9.
85 (s, 1H), 8.93 (d, 1H, J = 7.0Hz), 7.56-7.50 (m, 5
H), 7.27 (t, 1H, J = 6.2Hz), 7.05 (s, 1H), 6.95 (t,
1H, J = 6.2Hz), 2.53 (s, 3H), 2.02 (s, 3H); MS (APCI, m / z): 364 (M + H) +; HPLC (N): Rt = 6.5 min. Example 14) (4-Isopropyl-phenyl)-[4- (2-methyl-imidazo [1,
Using 2-α] pyridin-3-yl) -thiazol-2-yl] -amine (4-isopropyl-phenyl) -thiourea, the reaction was carried out in the same manner as in Example 1 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.31 (s, 1H), 8.
95 (d, 1H, J = 7.0Hz), 7.54 (d, 1H, J = 8.6Hz), 7.53
(d, 2H, J = 8.9Hz), 7.30-7.19 (m, 3H), 7.05 (s, 1H),
6.97 (dt, 1H, J = 1.1Hz, 6.8Hz), 2.89-2.82 (m, 2H),
2.52 (s, 3H), 1.19 (d, 6H, J = 6.8 Hz); MS (APCI, m / z): 349 (M + H) +; HPLC (N): Rt = 4.5 min. (Example 15 ) (4-Ethyl-phenyl)-[4- (2-methyl-imidazo [1,2-α]
The reaction was carried out in the same manner as in Example 1 using (pyridin-3-yl) -thiazol-2-yl] -amine (4-ethyl-phenyl) -thiourea to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.31 (s, 1H), 8.
95 (d, 1H, J = 7.0Hz), 7.54 (d, 3H, J = 8.6Hz), 7.27
(d, 1H, J = 6.8Hz), 7.18 (d, 2H, J = 8.4Hz), 7.05 (s,
1H), 6.97 (t, 1H, J = 6.8Hz), 2.60-2.50 (m, 5H), 1.17
(t, 3H, J = 7.8Hz); MS (APCI, m / z): 335 (M + H) +; HPLC (N): Rt = 4.6 min. (Example 16) (4-isopropoxy-phenyl )-[4- (2-Methyl-imidazo
Using [1,2-α] pyridin-3-yl) -thiazol-2-yl] -amine (4-isopropoxy-phenyl) -thiourea, the reaction was carried out in the same manner as in Example 1 to obtain the title compound. Was.

1H-NMR (DMSO-d6) δ: 10.17 (s, 1H), 8.
94 (d, 1H, J = 7.0Hz), 7.55-7.51 (m, 3H), 7.26 (t, 1
H, J = 8.4Hz), 7.00-6.90 (m, 4H), 4.55-4.51 (m, 1H),
2.53 (s, 3H), 1.25 (dd, 6H, J = 1.1Hz, 5.9Hz); MS (APCI, m / z): 365 (M + H) +; HPLC (N): Rt = 4.7 min. Example 17) 4- [4- (2-Methyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-ylamino] -benzoic acid ethyl ester 4-thioureido-ethyl benzoate (Reference Example) Using 49), a reaction was carried out in the same manner as in Example 1 to obtain the title compound.

Mp 205-208 (dec.); 1H-NMR (DMSO-d6) δ: 10.86 (s, 1H), 8.09 (d, 1H, J
= 6.8Hz), 7.94 (d, 2H, J = 8.9Hz), 7.76 (d, 2H, J = 8.9Hz)
Hz), 7.55 (d, 1H, J = 9.2Hz), 7.32-7.26 (m, 1H), 7.23
(s, 1H), 7.03-6.98 (m, 1H), 4.27 (q, 2H, J = 7.0Hz),
2.54 (s, 3H), 1.31 (t, 3H, J = 7.0 Hz); MS (APCI, m / z): 379 (M + H) +; HPLC (N): Rt = 4.8 min. (Example 18) ) [4- (2-Methyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl]-(3-trifluoromethyl-phenyl) -amine (3-trifluoromethyl-phenyl Using) -thiourea, the reaction was carried out in the same manner as in Example 1 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.82 (s, 1H), 8.
96 (d, 1H, J = 6.8Hz), 8.44 (s, 1H), 7.67-7.54 (m, 3
H), 7.32-7.26 (m, 2H), 7.19 (s, 1H), 6.91 (t, 1H,
J = 8.1 Hz), 2.55 (s, 3H); MS (APCI, m / z): 375 (M + H) +; HPLC (N): Rt = 4.6 min. (Example 19) (2,5- Dimethoxy-phenyl)-[4- (2-methyl-imidazo [1,
Using 2-α] pyridin-3-yl) -thiazol-2-yl] -amine (2,5-dimethoxy-phenyl) -thiourea, the reaction was carried out in the same manner as in Example 1 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 9.80 (s, 1H), 8.9
8 (d, 1H, J = 7.6Hz), 8.11 (d, 1H, J = 3.2Hz), 7.53 (d,
1H, J = 8.4Hz), 7.26 (t, 1H, J = 8.4Hz), 7.08 (s, 1
H), 6.94 (t, 2H, J = 8.4Hz), 6.54-6.50 (m, 1H), 3.83
(s, 3H), 3.66 (s, 3H), 2.53 (s, 3H); MS (APCI, m / z): 367 (M + H) +; HPLC (N): Rt = 5.5 min. (Example 20) (3,5-dimethyl-phenyl)-[4- (2-methyl-imidazo [1,2-
Using [α] pyridin-3-yl) -thiazol-2-yl] -amine (3,5-dimethyl-phenyl) -thiourea, the reaction was carried out in the same manner as in Example 1 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.27 (s, 1H), 9.
08 (d, 1H, J = 7.3Hz), 7.54 (d, 1H, J = 8.9Hz), 7.31-
7.25 (m, 3H), 7.06 (s, 1H), 6.99-6.94 (m, 1H), 6.6
4 (s, 1H), 2.55 (s, 3H), 2.26 (s, 3H); MS (APCI, m / z): 335 (M + H) +; HPLC (N): Rt = 4.9 min. Example 21) [4- (2-Methyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl]-(4-phenoxy-phenyl) -amine (4-phenoxy-phenyl)- The reaction was carried out in the same manner as in Example 1 using thiourea to obtain the title compound.

1H-NMR (CDCl3) δ: 8.93 (d, 1H, J = 6.8H
z), 7.55 (d, 1H, J = 8.9Hz), 7.33 (d, 2H, J = 8.9Hz),
7.20-7.14 (m, 2H), 6.92 (d 2H, J = 8.9Hz), 6.79 (t,
1H, J = 6.8Hz), 6.60 (s, 1H), 4.05 (q, 2H, J = 7.0Hz)
2.62 (s, 3H), 1.43 (t, 3H, J = 7.0 Hz); MS (APCI, m / z): 399 (M + H) +; HPLC (N): Rt = 4.8 min. (Example 22 ) (4-ethoxy-phenyl)-[4- (2-methyl-imidazo [1,2-
Example 1 using α] pyridin-3-yl) -thiazol-2-yl] -amine (4-ethoxy-phenyl) -thiourea
The reaction was carried out in the same manner as in to give the title compound.

MS (APCI, m / z): 351 (M + H) +; HPLC (N): Rt = 5.1 min. (Example 23) 3- [4- (2-methyl-imidazo [1,2 The reaction was carried out in the same manner as in Example 1 using -α] pyridin-3-yl) -thiazol-2-ylamino] -phenol (3-hydroxy-phenyl) -thiourea to obtain the title compound.

1H-NMR (CDCl3) δ: 8.81 (dd, 1H, J = 1.4
Hz, 5.6Hz), 7.49 (d, 1H, J = 9.2Hz), 7.20-7.13 (m, 2
H), 6.98-6.90 (m, 2H), 6.81-6.76 (m, 1H), 6.62 (s,
1H), 6.55-6.51 (m, 1H), 3.37-3.36 (m, 1H), 2.55
(s, 3H); MS (APCI, m / z): 323 (M + H) +; HPLC (N): Rt = 6.2 min. (Example 24) (2-methoxy-5-methyl-phenyl)- Example using [4- (2-methyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -amine (2-methoxy-5-methyl-phenyl) -thiourea The reaction was carried out in the same manner as in Example 1 to obtain the title compound.

1H-NMR (CDCl3) δ: 9.05 (d, 1H, J = 7.0H
z), 7.99 (s, 1H), 7.78 (s, 1H), 7.57 (d, 1H, J = 8.9H
z), 7.23-7.16 (m, 1H), 6.84-6.78 (m, 3H), 6.69 (s,
1H), 3.92 (s, 3H), 2.65 (s, 3H), 2.35 (s, 3H); MS (APCI, m / z): 351 (M + H) +; HPLC (N): Rt = 4.5 min Example 25 (2,4-Dimethyl-phenyl)-[4- (2-methyl-imidazo [1,2-
Using [α] pyridin-3-yl) -thiazol-2-yl] -amine (2,4-dimethyl-phenyl) -thiourea, the reaction was carried out in the same manner as in Example 1 to obtain the title compound.

1H-NMR (CDCl3) δ: 8.95 (d, 1H, J = 7.0H
z), 7.58-7.51 (m, 2H), 7.22-7.16 (m, 1H), 7.10 (s,
1H), 7.09 (d, 1H, J = 7.3Hz), 6.91 (s, 1H), 6.81 (t,
1H, J = 5.9Hz), 6.61 (s, 1H), 2.62 (s, 3H), 2.35
(s, 3H), 2.33 (s, 3H); MS (APCI, m / z): 335 (M + H) +; HPLC (N): Rt = 4.2 min. (Example 26) (4-cyclohexyl- Phenyl)-[4- (2-methyl-imidazo
Using [1,2-α] pyridin-3-yl) -thiazol-2-yl] -amine (4-cyclohexyl-phenyl) -thiourea, the reaction was carried out in the same manner as in Example 1 to obtain the title compound. .

1H-NMR (CDCl3) δ: 8.94 (d, 1H, J = 7.3H
z), 7.55 (d, 1H, J = 9.2Hz), 7.35-7.15 (m, 6H), 6.80
(t, 1H, J = 6.8Hz), 6.64 (s, 1H), 2.63 (s, 3H), 2.59
-2.45 (m, 1H), 1.91-1.71 (m, 6H), 1.47-1.22 (m, 4
H); MS (APCI, m / z): 389 (M + H) +; HPLC (N): Rt = 4.6 min. (Example 27) (3,5-bis-trifluoromethyl-phenyl)-[ 4- (2-methyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-
The reaction was carried out in the same manner as in Example 1 using yl] -amine (3,5-bis-trifluoromethyl-phenyl) -thiourea to obtain the title compound.

1H-NMR (CDCl3) δ: 9.01 (dd 1H, J = 1.4H
z, 5.9Hz), 8.22 (s, 2H), 7.56 (d, 1H, J = 8.9Hz), 7.48
(s, 1H), 7.30-7.22 (m, 1H), 6.86 (dt, 1H, J = 1.1Hz,
6.8Hz), 6.77 (s, 1H), 3.41 (brs, 1H), 2.64 (s, 3H); MS (APCI, m / z): 443 (M + H) +; HPLC (N): Rt = 4.0 min. (Example 28) [4- (2-Methyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl]-(2,3,4-trifluoro-phenyl)- Using the amine (2,3,4-trifluoro-phenyl) -thiourea,
The reaction was carried out in the same manner as in Example 1 to obtain the title compound.

1H-NMR (CDCl3) δ: 8.84 (d, 1H, J = 6.8H
z), 7.98-7.90 (m 1H), 7.58 (d, 1H, J = 9.2Hz), 7.24-
7.18 (m, 2H), 7.05-6.95 (m, 1H), 6.84-6.79 (m, 1H),
6.76 (s, 1H), 2.63 (s, 3H); MS (APCI, m / z): 361 (M + H) +; HPLC (N): Rt = 4.6 min. (Example 29) 4- [4 Using-(2-methyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-ylamino] -phenol (4-hydroxy-phenyl) -thiourea, the reaction was carried out as in Example 1. This gave the title compound.

1H-NMR (CDCl3 + CD3OD) δ: 8.81 (d 1H, J
= 6.5Hz), 7.51 (d, 1H, J = 7.6Hz), 7.34-7.24 (m, 4H),
7.11-7.04 (m, 1H), 6.87-6.84 (m, 3H), 6.59 (s, 1
H), 3.26 (s, 3H); MS (APCI, m / z): 323 (M + H) +; HPLC (N): Rt = 6.2 min. (Example 30) (2-fluoro-phenyl)- [4- (2-methyl-imidazo [1,2-
Example 1 using [α] pyridin-3-yl) -thiazol-2-yl] -amine (2-fluoro-phenyl) -thiourea
The reaction was carried out in the same manner as in to give the title compound.

1H-NMR (CDCl3) δ: 8.93 (dd 1H, J = 0.8H
z, 6.8Hz), 8.14 (dt 1H, J = 1.4Hz, 8.4Hz), 7.57 (d, 1
(H, J = 8.9Hz), 7.43 (brs, 1H), 7.24-7.12 (m, 4H), 7.
06-6.98 (m, 1H), 6.81 (dt, 1H, J = 1.4Hz, 8.4Hz), 6.
74 (s, 1H), 2.64 (s, 3H); MS (APCI, m / z): 325 (M + H) +; HPLC (N): Rt = 4.7 min. (Example 31) (2,6 -Diethyl-phenyl)-[4- (2-methyl-imidazo [1,2-
Using [α] pyridin-3-yl) -thiazol-2-yl] -amine (2,6-diethyl-phenyl) -thiourea, the reaction was carried out in the same manner as in Example 1 to obtain the title compound.

1H-NMR (CDCl3) δ: 8.99 (d 1H, J = 7.0H
z), 7.57 (d, 1H, J = 9.2Hz), 7.34-7.16 (m, 4H), 6.82
(t, 1H, J = 7.0Hz), 6.64 (brs, 1H), 6.51 (s, 1H),
2.73 (q, 4H, J = 7.6Hz), 2.62 (s, 3H), 1.24 (t, 6H, J =
7.6 Hz); MS (APCI, m / z): 363 (M + H) +; HPLC (N): Rt = 3.7 min. (Example 32) (2,6-dimethyl-phenyl)-[4- ( 2-methyl-imidazo [1,2-
Using [α] pyridin-3-yl) -thiazol-2-yl] -amine (2,6-dimethyl-phenyl) -thiourea, the reaction was carried out in the same manner as in Example 1 to obtain the title compound.

1H-NMR (CDCl3) δ: 8.97 (d 1H, J = 7.0H
z), 7.54 (d, 1H, J = 8.9Hz), 7.24-7.14 (m, 4H), 6.80
(dt, 1H, J = 1.1Hz, 6.5Hz), 6.71 (brs, 1H), 6.52 (s,
1H), 2.61 (s, 3H), 2.36 (s, 6H); MS (APCI, m / z): 335 (M + H) +; HPLC (N): Rt = 4.0 min. (Example 33) (Example 33) 4-tert-butyl-phenyl)-[4- (2-methyl-imidazo [1,2
Using -α] pyridin-3-yl) -thiazol-2-yl] -amine (4-tert-butyl-phenyl) -thiourea, the reaction was carried out in the same manner as in Example 1 to obtain the title compound.

1H-NMR (CDCl3) δ: 8.94 (d 1H, J = 7.0H
z), 7.55 (d, 1H, J = 9.2Hz), 7.42-7.32 (m, 5H), 7.18
(dt, 1H, J = 1.1Hz, 6.8Hz), 6.80 (dt, 1H, J = 1.4Hz,
7.0Hz), 6.55 (s, 1H), 2.63 (s, 3H), 1.34 (s, 9H); MS (APCI, m / z) 363 (M + H) +; HPLC (N): Rt = 4.6 min Example 34 4- [4- (2-Methyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-ylamino] -benzoic acid methyl ester 4-thioureido-methyl benzoate Example 1 used
The reaction was carried out in the same manner as in to give the title compound.

1H-NMR (CDCl3) δ: 8.94 (d 1H, J = 7.0H
z), 8.05 (d 2H, J = 8.6Hz), 7.98 (brs, 1H), 7.65 (d,
5H, J = 8.9Hz), 7.55 (d 2H, J = 8.6Hz), 7.29-7.26 (m,
1H), 6.87 (t, 1H, J = 6.5Hz), 6.79 (s, 1H), 3.91 (s,
3H), 2.65 (s, 3H); MS (APCI, m / z): 365 (M + H) +; HPLC (N): Rt = 2.5 min. (Example 35) (3-chloro-4-fluoro -Phenyl)-[4- (2-methyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -amine (3-chloro-4-fluoro-phenyl) -thiourea Then, the reaction was carried out in the same manner as in Example 1 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.65 (s, 1H), 8.
92 (d, 1H, J = 7.0Hz), 8.17 (d, 1H, J = 6.5Hz), 7.57
(d, 1H, J = 8.6Hz), 7.42-7.39 (m, 2H), 7.30 (t, 1H,
J = 6.8Hz), 7.17 (s, 1H), 6.97 (t, 1H, J = 7.0Hz), 2.5
4 (s, 3H); MS (APCI, m / z): 359 (M + H) +, 361 (M + H) +; HPLC (N): Rt = 5.5 min. (Example 36) 4-dimethyl-phenyl)-[4- (2-methyl-imidazo [1,2-
Using [α] pyridin-3-yl) -thiazol-2-yl] -amine (3,4-dimethyl-phenyl) -thiourea, the reaction was carried out in the same manner as in Example 1 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.24 (s, 1H), 9.
03 (d, 1H, J = 7.0Hz), 7.56 (d, 1H, J = 8.1Hz), 7.54
(s, 1H), 7.31-7.25 (m, 2H), 7.08 (d, 1H, J = 8.6Hz),
7.04 (s, 1H), 6.97 (t, 1H, J = 7.6Hz), 2.54 (s, 3H),
2.22 (s, 3H), 2.18 (s, 3H); MS (APCI, m / z): 335 (M + H) +; HPLC (N): Rt = 5.6 min. (Example 37) (4-chloro -Phenyl)-[4- (2-methyl-imidazo [1,2-α]
The reaction was carried out in the same manner as in Example 1 using (pyridin-3-yl) -thiazol-2-yl] -amine (4-chloro-phenyl) -thiourea to obtain the title compound.

Mp 192-195 ° C. (dec.); 1H-NMR (DMSO-d6) δ: 10.57 (s, 1H), 8.87 (d, 1H, J
= 7.0Hz), 7.68 (d, 2H, J = 8.9Hz), 7.55 (d, 1H, J = 8.9
Hz), 7.38 (d, 2H, J = 8.9Hz), 7.31-7.25 (m, 1H), 7.14
(s, 1H), 7.00-6.96 (m, 1H), 2.53 (s, 3H); MS (APCI, m / z): 341 (M + H) +, 343 (M + H) +; HPLC (N ): Rt = 5.5 min. (Example 38) (3-Fluoro-4-methyl-phenyl)-[4- (2-methyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2 -Yl] -amine (3-fluoro-4-methyl-phenyl) -thiourea (Reference Example 4
Using 5), the reaction was carried out in the same manner as in Example 1 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.56 (s, 1H), 8.
90 (d, 1H, J = 7.8Hz), 7.66 (d, 1H, J = 13.8Hz), 7.55
(d, 1H, J = 7.8Hz), 7.32-7.21 (m, 3H), 7.13 (s, 1H),
6.96 (t, 1H, J = 6.5Hz), 2.53 (s, 3H), 2.17 (s, 3H); MS (APCI, m / z): 339 (M + H) +; HPLC (N): Rt = 5.5 min. (Example 39) 1- [4- [4- (2-methyl-imidazo [1,2-α] pyridin-3-yl)
-Thiazol-2-ylamino] -phenyl] -ethanone (4-acetyl-phenyl) -thiourea (Reference Example 47)
And the reaction was carried out in the same manner as in Example 1 to obtain the title compound.

Mp 143 ° C. (dec.); 1H-NMR (DMSO-d6) δ: 10.90 (s, 1H), 8.89 (d, 1H, J
= 7.0Hz), 7.97 (d, 2H, J = 8.6Hz), 7.77 (d, 2H, J = 8.6
Hz), 7.57 (d, 1H, J = 8.4Hz), 7.33-7.28 (m, 1H), 7.24
(s, 1H), 7.02-6.98 (m, 1H), 2.55 (s, 3H), 2.50 (s,
3H); MS (APCI, m / z): 349 (M + H) +; HPLC (N): Rt = 6.3 min. (Example 40) (4-Fluoro-phenyl)-[4- (2-methyl -Imidazo [1,2-
Example 1 using [α] pyridin-3-yl) -thiazol-2-yl] -amine (4-fluoro-phenyl) -thiourea
The reaction was carried out in the same manner as in to give the title compound.

1H-NMR (DMSO-d6) δ: 10.44 (s, 1H), 8.
89 (d, 1H, J = 7.0Hz), 7.69-7.64 (m, 2H), 7.54 (d, 1
H, J = 8.1Hz), 7.28 (t, 1H, J = 6.8Hz), 7.19 (t, 2H, J
= 8.4Hz), 7.09 (s, 1H), 6.97 (t, 1H, J = 6.8Hz), 2.53
(s, 3H); MS (APCI, m / z): 325 (M + H) +; HPLC (N): Rt = 5.7 min. (Example 41) [4- (2-methyl-imidazo [1, Example using 2-α] pyridin-3-yl) -thiazol-2-yl]-(4-methyl-pyridin-2-yl) -amine (4-methyl-pyridin-2-yl) -thiourea The reaction was carried out in the same manner as in Example 1 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 11.42 (s, 1H), 9.
13 (d, 1H, J = 6.8Hz), 8.21 (d, 1H, J = 4.9Hz), 7.54
(d, 1H, J = 8.9Hz), 7.27 (t, 1H, J = 7.8Hz), 7.17 (s,
1H), 6.96 (t, 1H, J = 6.8Hz), 6.92 (s, 1H), 6.81 (d,
1H, J = 5.4Hz), 2.54 (s, 3H), 2.31 (s, 3H); MS (APCI, m / z): 322 (M + H) +; HPLC (N): Rt = 5.9 min. Example 42) [4- (2-Methyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl]-(5-methyl-pyridin-2-yl) -amine (5- Methyl-pyridin-2-yl) -thiourea (Reference Example 4)
Using 4), a reaction was carried out in the same manner as in Example 1 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 11.39 (s, 1H), 9.
13 (d, 1H, J = 6.8Hz), 8.18 (s, 1H), 7.60-7.52 (m, 2
H), 7.27 (t, 1H, J = 7.6Hz), 7.15 (s, 1H), 7.04 (d,
1H, J = 8.6Hz), 6.94 (t, 1H, J = 6.8Hz), 2.54 (s, 3H),
2.25 (s, 3H); MS (APCI, m / z): 322 (M + H) +, HPLC (N); Rt = 5.8 min. (Example 43) (5-chloro-pyridin-2-yl) -[4- (2-methyl-imidazo
Using [1,2-α] pyridin-3-yl) -thiazol-2-yl] -amine (5-chloro-pyridin-2-yl) -thiourea, the reaction was carried out in the same manner as in Example 1, The compound was obtained.

1H-NMR (DMSO-d6) δ: 11.69 (s, 1H), 9.
11 (d, 1H, J = 7.0Hz), 8.39 (d, 1H, J = 2.4Hz), 7.85
(dd, 1H, J = 2.7Hz, 8.9Hz), 7.54 (d, 1H, J = 8.9Hz),
7.29 (d, 1H, J = 7.8Hz), 7.24 (s, 1H), 7.15 (d, 1H,
J = 8.6Hz), 6.95 (t, 1H, J = 6.8Hz), 2.54 (s, 3H); MS (APCI, m / z): 342 (M + H) +, 344 (M + H) +; HPLC (N): Rt = 5.2 min. (Example 44) (6-Methoxy-pyridin-3-yl)-[4- (2-methyl-imidazo)
[1,2-α] pyridin-3-yl) -thiazol-2-yl] -amine (6-methoxy-pyridin-3-yl) -thiourea (Reference Example 4)
Using 3), a reaction was carried out in the same manner as in Example 1 to obtain the title compound.

Mp 185-187 ° C .; 1H-NMR (DMSO-d6) δ: 10.34 (s, 1H), 8.87 (d, 1H, J
= 7.0Hz), 8.46 (d, 1H, J = 3.0Hz), 7.99 (dd, 1H, J = 3.
0Hz, 8.9Hz), 7.54 (d, 1H, J = 8.6Hz), 7.30-7.24 (m,
1H), 7.07 (s, 1H), 6.98-6.93 (m, 1H), 6.84 (d, 1H,
J = 8.9Hz), 3.82 (s, 3H), 2.51 (s, 3H); MS (APCI, m / z): 338 (M + H) +; HPLC (N); Rt = 5.3 min. 45) [4- (2-Methyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -pyridin-2-yl-amine (pyridin-2-yl) -thiourea Then, the reaction was carried out in the same manner as in Example 1 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 11.51 (s, 1H), 9.
14 (d, 1H, J = 7.0Hz), 8.35 (d, 1H, J = 4.3Hz), 7.74
(t, 1H, J = 6.8Hz), 7.53 (d, 1H, J = 9.2Hz), 7.28 (d,
1H, J = 9.2Hz), 7.19 (s, 1H), 7.12 (d, 1H, J = 8.1Hz),
6.99-6.93 (m, 2H), 2.54 (s, 3H); MS (APCI, m / z): 308 (M + H) +; HPLC (N): Rt = 5.9 min. (Example 46) [4 Example using-(2-methyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -pyridin-3-yl-amine (pyridin-3-yl) -thiourea 1
The reaction was carried out in the same manner as in to give the title compound.

1H-NMR (DMSO-d6) δ: 10.65 (s, 1H), 8.
86 (d, 1H, J = 7.0Hz), 8.81 (d, 1H, J = 2.4Hz), 8.18
(d, 1H, J = 4.6Hz), 8.15 (d, 1H, J = 2.4Hz), 7.55 (d,
1H, J = 8.9Hz), 7.36 (dd, 1H, J = 4.9Hz, 8.4Hz), 7.29
(t, 1H, J = 6.8Hz), 7.18 (s, 1H), 6.97 (t, 1H, J = 7.0H
z), 2.53 (s, 3H); MS (APCI, m / z): 308 (M + H) +; HPLC (N): Rt = 5.3 min. (Example 47) (6-chloro-pyridine-3 -Yl)-[4- (2-methyl-imidazo
[1,2-α] pyridin-3-yl) -thiazol-2-yl] -amine (6-chloro-pyridin-3-yl) -thiourea (Reference Example 46)
And the reaction was carried out in the same manner as in Example 1 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.81 (s, 1H), 8.
81 (d, 1H, J = 7.0Hz), 8.70 (d, 1H, J = 2.7Hz), 8.17
(dd, 1H, J = 3.0Hz, 8.9Hz), 7.56 (d, 1H, J = 8.9Hz),
7.49 (d, 1H, J = 8.6Hz), 7.29 (t, 1H, J = 6.8Hz), 7.22
(s, 1H), 6.98 (t, 1H, J = 7.0Hz), 2.52 (s, 3H); MS (APCI, m / z): 342 (M + H) +, 344 (M + H) +; HPLC (N): Rt = 5.1 min. (Example 48) 1- [4- [4- (2,5,7-trimethyl-imidazo [1,2-α] pyridine)
-3-yl) -thiazol-2-ylamino] -phenyl] -ethanone Using the compound of Reference Example 7 and (4-acetyl-phenyl) -thiourea (Reference Example 47), a reaction was carried out in the same manner as in Example 1. The title compound was obtained.

1H-NMR (CDCl3) δ: 7.96-7.93 (m, 1H),
7.95 (d, 2H, J = 8.9Hz), 7.45 (d, 2H, J = 8.9Hz), 7.21
(brs, 1H), 6.80 (s 1H), 6.35 (brs, 1H), 2.57 (s, 3
H), 2.37 (s, 3H), 2.36 (s, 3H), 2.35 (s, 3H); MS (APCI, m / z): 377 (M + H) +; HPLC (N): Rt = 9.3 min Example 49 p-Tolyl- [4- (2,5,7-trimethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -amine Compound of Reference Example 7 And using p-tolyl-thiourea (purchased from Tokyo Kasei) in the same manner as in Example 1,
The title compound was obtained.

1H-NMR (CDCl3) δ: 7.20-7.09 (m, 6H),
6.62 (s 1H), 6.30 (brs, 1H), 2.37 (s, 3H), 2.35 (s,
3H), 2.33 (s, 3H); MS (APCI, m / z): 349 (M + H) +; HPLC (N): Rt = 9.1 min. (Example 50) (4-trifluoromethyl-phenyl )-[4- (2,5,7-Trimethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-
Yl] -amine Using the compound of Reference Example 7 and (4-trifluoromethyl-phenyl) -thiourea (Reference Example 2), the reaction was carried out in the same manner as in Example 1 to obtain the title compound.

1H-NMR (CDCl3 + DMSO-d6) δ: 7.72 (brs,
1H), 7.50 (d, 2H, J = 8.4Hz), 7.33 (d, 2H, J = 8.4H
z), 7.19 (s, 1H), 6.71 (s 1H), 6.34 (s, 1H), 2.42
(s, 3H), 2.38 (s, 3H), 2.36 (s, 3H); MS (APCI, m / z): 403 (M + H) +; HPLC (N): Rt = 10.0 min. 51) [4- (2,8-Dimethyl-imidazo [1,2-α] pyridin-3-yl)-
Thiazol-2-yl]-(4-methoxy-phenyl) -amine Using the compound of Reference Example 1 and (4-methoxy-phenyl) -thiourea (Reference Example 3), a reaction was carried out in the same manner as in Example 1. The title compound was obtained.

1H-NMR (CDCl3 + DMSO-d6) δ: 9.11 (s, 1
H), 8.84 (d, 1H, J = 7.0Hz), 7.53 (d, 2H, J = 8.9Hz),
6.99 (d, 1H, J = 6.8Hz), 6.89 (d, 2H, J = 8.9Hz), 6.75
(t, 1H, J = 6.8Hz), 6.59 (s, 1H), 3.81 (s, 3H), 2.65
(s, 3H), 2.62 (s, 3H); MS (APCI, m / z) 351 (M + H) +; HPLC (N): Rt = 6.1 min. (Example 52) 1- [4- [ 4- (2,8-dimethyl-imidazo [1,2-α] pyridine-3-
Yl) -thiazol-2-ylamino] -phenyl] -ethanone The compound of Reference Example 1 and (4-acetyl-phenyl) -thiourea (Reference Example 47) were reacted in the same manner as in Example 1 to give the title compound I got

1H-NMR (CDCl3 + DMSO-d6) δ: 10.01 (s,
1H), 8.80 (d, 1H, J = 7.3Hz), 7.94 (d, 2H, J = 8.9Hz),
7.74 (d, 2H, J = 8.9Hz), 7.37-7.34 (m, 1H), 7.04-7.02
(m, 1H), 6.77-6.73 (m, 1H) 2.66 (s, 3H), 2.64 (s,
3H), 2.57 (s, 3H); MS (APCI, m / z): 363 (M + H) +; HPLC (N): Rt = 5.9 min. (Example 53) [4- (2,8- Dimethyl-imidazo [1,2-α] pyridin-3-yl)-
Thiazol-2-yl] -p-tolyl-amine Using the compound of Reference Example 1 and p-tolyl-thiourea (purchased from Tokyo Chemical Industry), a reaction was carried out in the same manner as in Example 1,
The title compound was obtained.

1H-NMR (DMSO-d6) δ: 10.28 (s, 1H), 8.
79 (d, 1H, J = 6.5Hz), 7.52 (d, 2H, J = 8.4Hz), 7.14
(d, 2H, J = 8.4Hz), 7.09 (d, 1H, J = 5.7Hz), 7.03 (s,
1H), 6.86 (t, 1H, J = 7.3Hz), 2.53 (s, 3H), 2.50 (s,
3H), 2.26 (s, 3H); MS (APCI, m / z): 335 (M + H) +; HPLC (N): Rt = 5.4 min. (Example 54) 4- [4- (2, 8-Dimethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-ylamino] -benzoic acid ethyl ester The compound of Reference Example 1 and 4-thioureido-ethyl benzoate (Reference Example 49) were used. Then, the reaction was carried out in the same manner as in Example 1 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.85 (s, 1H), 8.
74 (d, 1H, J = 6.5Hz), 7.94 (d, 2H, J = 8.6Hz), 7.76
(d, 2H, J = 8.6Hz), 7.21 (s, 1H), 7.10 (d, 1H, J = 6.8
Hz), 6.91 (t, 1H, J = 6.8Hz), 4.27 (q, 2H, J = 7.0Hz),
2.55 (s, 3H), 2.50 (s, 3H), 1.31 (t, 3H, J = 7.0Hz); MS (APCI, m / z): 393 (M + H) +; HPLC (N): Rt = 4.8 min. (Example 55) [4- (2,8-dimethyl-imidazo [1,2-α] pyridin-3-yl)-
Thiazol-2-yl]-(6-methoxy-pyridin-3-yl) -amine The compound of Reference Example 1 and (6-methoxy-pyridin-3-
Example 1 using yl) -thiourea (Reference Example 43)
The reaction was carried out in the same manner as in to give the title compound.

1H-NMR (DMSO-d6) δ: 10.30 (s, 1H), 8.
72 (d, 1H, J = 7.3Hz), 8.46 (d, 1H, J = 2.4Hz), 7.98
(dd, 1H, J = 2.4Hz, 8.6Hz), 7.08 (d, 1H, J = 5.7Hz),
7.05 (s, 1H), 6.86 (t, 1H, J = 7.3Hz), 6.86 (s, 1H),
3.82 (s, 3H), 2.52 (s, 3H), 2.09 (s, 3H); MS (APCI, m / z): 352 (M + H) +; HPLC (N): Rt = 5.3 min. Example 56) [4- (2,8-dimethyl-imidazo [1,2-α] pyridin-3-yl)-
Thiazol-2-yl]-(4-trifluoromethyl-phenyl)
-Amine The reaction was carried out in the same manner as in Example 1 using the compound of Reference Example 1 and (4-trifluoromethyl-phenyl) -thiourea (Reference Example 2) to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.84 (s, 1H), 8.
71 (d, 1H, J = 7.0Hz), 7.84 (d, 2H, J = 8.4Hz), 7.69
(d, 2H, J = 8.4Hz), 7.21 (s, 1H), 7.10 (d, 1H, J = 7.3
Hz), 6.90 (t, 1H, J = 7.3Hz), 2.54 (s, 3H), 2.50 (s,
3H); MS (APCI, m / z): 389 (M + H) +; HPLC (N): Rt = 4.8 min. (Example 57) [4- (2,6-dimethyl-imidazo [1,2 -α] pyridin-3-yl)-
Thiazol-2-yl]-(4-methoxy-phenyl) -amine Using the compound of Reference Example 5 and (4-methoxy-phenyl) -thiourea (Reference Example 3), a reaction was carried out in the same manner as in Example 1, The title compound was obtained.

1H-NMR (DMSO-d6) δ: 10.17 (s, 1H), 8.
86 (s, 1H), 7.57 (d, 2H, J = 8.6Hz), 7.45 (d, 1H, J =
9.5Hz), 7.13 (d, 1H, J = 10.5Hz), 6.98 (s, 1H), 6.94
(d, 2H, J = 8.6Hz), 3.73 (s, 3H), 2.50 (s, 3H), 2.31
(s, 3H); MS (APCI, m / z): 351 (M + H) +; HPLC (N): Rt = 7.3 min. (Example 58) 1- [4- [4- (2,6 -Dimethyl-imidazo [1,2-α] pyridine-3-
Yl) -thiazol-2-ylamino] -phenyl] -ethanone The compound of Reference Example 5 and (4-acetyl-phenyl) -thiourea (Reference Example 47) were reacted in the same manner as in Example 1 to give the title compound I got

Mp 164-169 ° C .; 1H-NMR (DMSO-d6) δ: 10.88 (s, 1H), 8.79 (s, 1H),
7.96 (d, 2H, J = 8.6Hz), 7.78 (d, 2H, J = 8.6Hz), 7.46
(d, 1H, J = 9.2Hz), 7.21 (s, 1H), 7.15 (d, 1H, J = 9.2Hz)
Hz), 2.52 (s, 3H), 2.50 (s, 3H), 2.33 (s, 3H); MS (APCI, m / z): 363 (M + H) +; HPLC (N): Rt = 6.5 min Example 59 [4- (2,6-Dimethyl-imidazo [1,2-α] pyridin-3-yl)-
Thiazol-2-yl] -p-tolyl-amine Using the compound of Reference Example 5 and p-tolyl-thiourea (purchased from Tokyo Kasei), a reaction was carried out in the same manner as in Example 1,
The title compound was obtained.

1H-NMR (DMSO-d6) δ: 10.29 (s, 1H), 8.
88 (s, 1H), 7.55 (d, 2H, J = 8.1Hz), 7.45 (d, 1H, J =
8.9Hz), 7.15 (d, 3H, J = 8.1Hz), 7.03 (s, 1H), 2.50
(s, 3H), 2.32 (s, 3H), 2.27 (s, 3H); MS (APCI, m / z): 335 (M + H) +; HPLC (N): Rt = 6.1 min. 60) 4- [4- (2,6-Dimethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-ylamino] -benzoic acid ethyl ester The compound of Reference Example 5 and 4-thioureido- Using ethyl benzoate (Reference Example 49), the reaction was carried out in the same manner as in Example 1 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.86 (s, 1H), 8.
79 (s, 1H), 7.94 (d, 2H, J = 8.6Hz), 7.78 (d, 2H, J =
8.6Hz), 7.47 (d, 1H, J = 8.9Hz), 7.21 (s, 1H), 7.16
(d, 1H, J = 8.6Hz), 4.28 (q, 2H, J = 7.0Hz), 2.52 (s, 3
H), 2.32 (s, 3H), 1.31 (t, 3H, J = 7.0Hz); MS (APCI, m / z): 393 (M + H) +; HPLC (N): Rt = 5.7 min. Example 61) [4- (2,6-dimethyl-imidazo [1,2-α] pyridin-3-yl)-
Thiazol-2-yl]-(6-methoxy-pyridin-3-yl) -amine The compound of Reference Example 5 and (6-methoxy-pyridin-3-
Example 1 using yl) -thiourea (Reference Example 43)
The reaction was carried out in the same manner as in to give the title compound.

1H-NMR (DMSO-d6) δ: 10.30 (s, 1H), 8.
81 (s, 1H), 8.47 (d, 1H, J = 2.7Hz), 8.02 (dd, 1H, J
= 2.7Hz, 8.9Hz), 7.45 (d, 1H, J = 9.2Hz), 7.13 (d, 1
H, J = 9.2Hz), 7.04 (s, 1H), 6.85 (d, 1H, J = 8.9Hz),
3.83 (s, 3H), 2.50 (s, 3H), 2.30 (s, 3H); MS (APCI, m / z): 352 (M + H) +; HPLC (N): Rt = 6.2 min. Example 62) [4- (2,6-dimethyl-imidazo [1,2-α] pyridin-3-yl)-
Thiazol-2-yl]-(4-trifluoromethyl-phenyl)
-Amine The reaction was carried out in the same manner as in Example 1 using the compound of Reference Example 5 and (4-trifluoromethyl-phenyl) -thiourea (Reference Example 2) to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.85 (s, 1H), 8.
76 (s, 1H), 7.86 (d, 2H, J = 8.4Hz), 7.69 (d, 2H, J =
8.4Hz), 7.48 (d, 1H, J = 9.2Hz), 7.21 (s, 1H), 7.16
(d, 1H, J = 9.7Hz), 2.52 (s, 3H), 2.32 (s, 3H); MS (APCI, m / z): 389 (M + H) +; HPLC (N): Rt = 5.3 min. (Example 63) [4- (2,7-dimethyl-imidazo [1,2-α] pyridin-3-yl)-
Thiazol-2-yl]-(4-methoxy-phenyl) -amine Using the compound of Reference Example 6 and (4-methoxy-phenyl) -thiourea (Reference Example 3), a reaction was carried out in the same manner as in Example 1. The title compound was obtained.

1H-NMR (DMSO-d6) δ: 10.16 (s, 1H), 8.
85 (d, 1H, J = 7.3Hz), 7.54 (d, 2H, J = 8.4Hz), 7.31
(s, 1H), 6.95 (s, 1H), 6.93 (d, 2H, J = 8.4Hz), 6.82
(d, 1H, J = 6.8Hz), 3.24 (s, 3H), 2.50 (s, 3H), 2,37
(s, 3H); MS (APCI, m / z): 351 (M + H) +; HPLC (N): Rt = 9.1 min. (Example 64) 1- [4- [4- (2,7 -Dimethyl-imidazo [1,2-α] pyridine-3-
Yl) -thiazol-2-ylamino] -phenyl] -ethanone The compound of Reference Example 6 and (4-acetyl-phenyl) -thiourea (Reference Example 47) were reacted in the same manner as in Example 1 to give the title compound I got

1H-NMR (DMSO-d6) δ: 10.86 (s, 1H), 8.
80 (d, 1H, J = 7.6Hz), 7.97 (d, 2H, J = 6.2Hz), 7.76
(d, 2H, J = 6.2Hz), 7.34 (s, 1H), 7.17 (d, 1H, J = 2.4
Hz), 6.87 (d, 1H, J = 7.0Hz), 2.56 (s, 3H), 2.51 (s,
3H), 2.34 (s, 3H); MS (APCI, m / z): 363 (M + H) +; HPLC (N): Rt = 7.2 min. (Example 65) [4- (2,7- Dimethyl-imidazo [1,2-α] pyridin-3-yl)-
Thiazol-2-yl] -p-tolyl-amine Using the compound of Reference Example 6 and p-tolyl-thiourea (purchased from Tokyo Kasei), a reaction was carried out in the same manner as in Example 1,
The title compound was obtained.

1H-NMR (DMSO-d6) δ: 10.27 (s, 1H), 8.
85 (d, 1H, J = 7.0Hz), 7.52 (d, 2H, J = 8.6Hz), 7.31
(s, 1H), 7.15 (d, 2H, J = 8.6Hz), 6.99 (s, 1H), 6.82
(d, 1H, J = 7.0Hz), 2.50 (s, 3H), 2.38 (s, 3H), 2.26
(s, 3H); MS (APCI, m / z): 335 (M + H) +; HPLC (N): Rt = 6.6 min. (Example 66) 4- [4- (2,7-dimethyl- Example 1 Ethyl imidazo [1,2-α] pyridin-3-yl) -thiazol-2-ylamino] -benzoate Employing the compound of Reference Example 6 and ethyl 4-thioureido-benzoate (Reference Example 49), The reaction was carried out in the same manner as in Example 1 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.84 (s, 1H), 8.
79 (d, 1H, J = 7.0Hz), 7.94 (d, 2H, J = 8.9Hz), 7.76
(d, 2H, J = 8.9Hz), 7.33 (s, 1H), 7.16 (s, 1H), 6.86
(d, 1H, J = 7.3Hz), 4.28 (q, 2H, J = 7.3Hz), 2.50 (s,
3H), 2.38 (s, 3H), 1.31 (t, 3H, J = 7.3Hz); MS (APCI, m / z): 393 (M + H) +; HPLC (N): Rt = 6.5 min. Example 67) [4- (2,7-Dimethyl-imidazo [1,2-α] pyridin-3-yl)-
Thiazol-2-yl]-(6-methoxy-pyridin-3-yl) -amine The compound of Reference Example 6 and (6-methoxy-pyridin-3-
Example 1 using yl) -thiourea (Reference Example 43)
The reaction was carried out in the same manner as in to give the title compound.

1H-NMR (DMSO-d6) δ: 10.29 (s, 1H), 8.
76 (d, 1H, J = 7.3Hz), 8.46 (d, 1H, J = 3.0Hz), 7.98
(dd, 1H, J = 3.0Hz, 8.9Hz), 7.31 (s, 1H), 7.01 (s, 1
H), 6.85 (d, 1H, J = 8.9Hz), 6.80 (s, 1H), 3.42 (s,
3H), 2.49 (s, 3H), 2.37 (s, 3H); MS (APCI, m / z): 352 (M + H) +; HPLC (N): Rt = 6.1 min. (Example 68) 4- (2,7-dimethyl-imidazo [1,2-α] pyridin-3-yl)-
Thiazol-2-yl]-(4-trifluoromethyl-phenyl)
-Amine The reaction was carried out in the same manner as in Example 1 using the compound of Reference Example 6 and (4-trifluoromethyl-phenyl) -thiourea (Reference Example 2) to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.82 (s, 1H), 8.
77 (d, 1H, J = 7.3Hz), 7.84 (d, 2H, J = 8.9Hz), 7.69
(d, 2H, J = 8.9Hz), 7.32 (s, 1H), 7.16 (s, 1H), 6.85
(d, 1H, J = 6.8Hz), 2.50 (s, 3H), 2.38 (s, 3H); MS (APCI, m / z): 389 (M + H) +; HPLC (N): Rt = 5.6 min. (Example 69) (4-Methoxy-phenyl)-[5-methyl-4- (2-methyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -amine Using the compound of Reference Example 9 and (4-methoxy-phenyl) -thiourea (Reference Example 3), the reaction was carried out in the same manner as in Example 1 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 9.99 (s, 1H), 8.2
0 (d, 1H, J = 6.8Hz), 7.54-7.53 (m, 1H), 7.49 (d, 2
H, J = 8.9Hz), 7.25 (t, 1H, J = 8.1Hz), 6.91-6.84 (m,
1H), 6.85 (d, 2H, J = 8.9Hz), 3.68 (s, 3H), 2.30 (s,
3H), 2.18 (s, 3H); MS (APCI, m / z): 351 (M + H) +; HPLC (N); Rt = 6.5 min. (Example 70) 1- [4- [5- Methyl-4- (2-methyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-ylamino] -phenyl] -ethanone The compound of Reference Example 9 and (4-acetyl-phenyl) -thiourea The reaction was carried out in the same manner as in Example 1 using (Reference Example 47) to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.69 (s, 1H), 8.
20 (d, 1H, J = 6.8Hz), 7.89 (d, 2H, J = 8.4Hz), 7.68
(d, 2H, J = 8.4Hz), 7.54 (d, 2H, J = 8.9Hz), 7.28 (t,
1H, J = 8.4Hz), 6.93-6.91 (m, 1H), 2.49 (s, 3H), 2.3
2 (s, 3H), 2.24 (s, 3H); MS (APCI, m / z): 363 (M + H) +; HPLC (N): Rt = 7.2 min. (Example 71) [5-methyl -4- (2-Methyl-imidazo [1,2-α] pyridine-3-
Yl) -thiazol-2-yl] -p-tolyl-amine Using the compound of Reference Example 9 and p-tolyl-thiourea (purchased from Tokyo Kasei), a reaction was carried out in the same manner as in Example 1,
The title compound was obtained.

1H-NMR (DMSO-d6) δ: 10.10 (s, 1H), 8.
20 (d, 1H, J = 7.0Hz), 7.54 (d, 1H, J = 8.9Hz), 7.46
(d, 2H, J = 8.6Hz), 7.27 (t, 1H, J = 6.8Hz), 7.06 (d,
2H, J = 8.6Hz), 6.90 (t, 1H, J = 6.8Hz), 2.32 (s, 3H),
2.22 (s, 3H), 2.20 (s, 3H); MS (APCI, m / z): 335 (M + H) +; HPLC (N): Rt = 5.7 min. (Example 72) 4- [5 -Methyl-4- (2-methyl-imidazo [1,2-α] pyridine-3
-Yl) -thiazol-2-ylamino] -benzoic acid ethyl ester Using the compound of Reference Example 9 and 4-thioureido-ethyl benzoate (Reference Example 49), the reaction was carried out in the same manner as in Example 1, and the title compound was obtained. Obtained.

1H-NMR (DMSO-d6) δ: 10.67 (s, 1H), 8.
20 (d, 1H, J = 6.5Hz), 7.86 (d, 2H, J = 7.0Hz), 7.68
(d, 2H, J = 7.0Hz), 7.54 (d, 1H, J = 8.6Hz), 7.27 (t,
1H, J = 7.6Hz), 6.91 (t, 1H, J = 6.5Hz), 4.24 (q, 2H,
J = 7.3Hz), 2.31 (s, 3H), 2.24 (s, 3H), 1.28 (t, 3H,
J (7.3 Hz); MS (APCI, m / z): 393 (M + H) +; HPLC (N): Rt = 5.8 min. (Example 73) (6-methoxy-pyridin-3-yl)- [5-methyl-4- (2-methyl
-Imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -amine The compound of Reference Example 9 and (6-methoxy-pyridin-3-
Example 1 using yl) -thiourea (Reference Example 43)
The reaction was carried out in the same manner as in to give the title compound.

1H-NMR (DMSO-d6) δ: 10.14 (s, 1H), 8.
42 (s, 1H), 8.21 (d, 2H, J = 6.8Hz), 7.92 (dd, 1H, J
= 2.2Hz, 8.4Hz), 7.54 (d, 1H, J = 8.6Hz), 7.27 (t, 1
H, J = 8.1Hz), 6.91 (t, 1H, J = 6.8Hz), 6.77 (d, 1H, J
= 8.4Hz), 3.78 (s, 3H), 2.31 (s, 3H), 2.20 (s, 3H); MS (APCI, m / z): 352 (M + H) +; HPLC (N): Rt = 5.5 min. (Example 74) [5-methyl-4- (2-methyl-imidazo [1,2-α] pyridine-3-
Yl) -thiazol-2-yl]-(4-trifluoromethyl-phenyl) -amine Example 1 was prepared using the compound of Reference Example 9 and (4-trifluoromethyl-phenyl) -thiourea (Reference Example 2). The reaction was carried out in the same manner as in to give the title compound.

1H-NMR (DMSO-d6) δ: 10.65 (s, 1H), 8.
18 (d, 1H, J = 6.8Hz), 7.76 (d, 2H, J = 8.9Hz), 7.60
(d, 2H, J = 8.9Hz), 7.53 (d, 1H, J = 9.2Hz), 7.27 (t,
1H, J = 5.4Hz), 6.90 (t, 1H, J = 6.8Hz), 2.31 (s, 3H),
2.23 (s, 3H); MS (APCI, m / z): 389 (M + H) +; HPLC (N): Rt = 5.3 min. (Example 75) (4-methoxy-phenyl)-[4- (2-methyl-6-trifluoromethyl-imidazo [1,2-α] pyridin-3-yl) -thiazole
-2-yl] -amine The reaction was carried out in the same manner as in Example 1 using the compound of Reference Example 11 and (4-methoxy-phenyl) -thiourea (Reference Example 3) to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.27 (s, 1H), 9.
69 (s, 1H), 7.75 (d, 1H, J = 8.9Hz), 7.56 (d, 2H, J =
8.9Hz), 7.54-7.50 (m, 1H), 7.12 (s, 1H), 6.90 (d,
2H, J = 8.9Hz), 3.73 (s, 3H), 2.59 (s, 3H); MS (APCI, m / z): 405 (M + H) +; HPLC (N): Rt = 3.8 min. Example 76) 1- [4- [4- (2-methyl-6-trifluoromethyl-imidazo [1,
2-α] pyridin-3-yl) -thiazol-2-ylamino] -phenyl] -ethanone Same as Example 1 using the compound of Reference Example 11 and (4-acetyl-phenyl) -thiourea (Reference Example 47). To give the title compound.

1H-NMR (DMSO-d6) δ: 10.95 (s, 1H), 9.
64 (s, 1H), 7.93 (d, 2H, J = 8.1Hz), 7.95-7.90 (m, 1
H,), 7.77 (d, 2H, J = 8.1Hz), 7.55 (d, 1H, J = 9.5Hz),
7.34 (s, 1H), 2.61 (s, 3H), 2.50 (s, 3H); MS (APCI, m / z): 417 (M + H) +; HPLC (N): Rt = 4.2 min. Example 77) [4- (2-methyl-6-trifluoromethyl-imidazo [1,2-α]
Using the compound of Reference Example 11 and p-tolyl-thiourea (purchased from Tokyo Kasei), the reaction was carried out in the same manner as in Example 1, The title compound was obtained.

1H-NMR (DMSO-d6) δ: 10.10 (s, 1H), 8.
21 (d, 1H, J = 7.0Hz), 7.53 (d, 1H, J = 8.9Hz), 7.46
(d, 2H, J = 8.6Hz), 7.27 (t, 1H, J = 6.8Hz), 7.06 (d,
2H, J = 8.6Hz), 6.90 (t, 1H, J = 6.8Hz), 2.32 (s, 3H),
2.20 (s, 3H); MS (APCI, m / z): 389 (M + H) +; HPLC (N); Rt = 3.5 min. (Example 78) 4- [4- (2-methyl-6 -Trifluoromethyl-imidazo [1,2-
α] pyridin-3-yl) -thiazol-2-ylamino] -benzoic acid ethyl ester Using the compound of Reference Example 11 and 4-thioureido-ethyl benzoate (Reference Example 49), a reaction was carried out in the same manner as in Example 1. This gave the title compound.

1H-NMR (DMSO-d6) δ: 10.94 (s, 1H), 9.
65 (s, 1H), 7.93 (d, 2H, J = 8.4Hz), 7.77 (d, 2H, J =
8.4Hz), 7.67 (d, 1H, J = 7.8Hz), 7.54 (d, 1H, J = 9.7H
z), 7.33 (s, 1H), 4.29 (q, 2H, J = 7.0Hz), 2.61 (s, 3
H), 1.31 (t, 3H, J = 7.0 Hz); MS (APCI, m / z): 447 (M + H) +; HPLC (N): Rt = 3.9 min. (Example 79) Methoxy-pyridin-3-yl)-[4- (2-methyl-6-trifluoromethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -amine Reference Example 11 Compound and (6-methoxy-pyridine-3)
Using -yl) -thiourea (Reference Example 43), the reaction was carried out in the same manner as in Example 1 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.37 (s, 1H), 9.
57 (s, 1H), 8.04 (dd, 1H, J = 3.0Hz, 8.4Hz), 7.75
(d, 1H, J = 9.2Hz), 7.50 (d, 1H, J = 10.3Hz), 7.18 (s,
1H), 6.79 (d, 1H, J = 8.9Hz), 3.83 (s, 3H), 2.58 (s,
3H); MS (APCI, m / z): 406 (M + H) +; HPLC (N): Rt = 3.3 min. (Example 80) [4- (2-methyl-6-trifluoromethyl-imidazo [1,2-α]
Pyridin-3-yl) -thiazol-2-yl]-(4-trifluoromethyl-phenyl) -amine Using the compound of Reference Example 11 and (4-trifluoromethyl-phenyl) -thiourea (Reference Example 2). Example 1
The reaction was carried out in the same manner as in to give the title compound.

1H-NMR (DMSO-d6) δ: 10.92 (s, 1H), 9.
62 (s, 1H), 7.85 (d, 2H, J = 8.4Hz), 7.79-7.52 (m, 4
H), 7.33 (s, 1H), 2.60 (s, 3H); MS (APCI, m / z): 443 (M + H) +; HPLC (N): Rt = 3.6 min. (Example 81) 4- (6-chloro-2-methyl-imidazo [1,2-α] pyridine-3-
Yl) -thiazol-2-yl]-(4-methoxy-phenyl) -amine Using the compound of Reference Example 12 and (4-methoxy-phenyl) -thiourea (Reference Example 3), reacted in the same manner as in Example 1. To give the title compound.

Mp 218-222 ° C. (dec.); 1H-NMR (DMSO-d6) δ: 10.22 (s, 1H), 9.29 (d, 1H, J
= 1.9Hz), 7.59 (d, 1H, J = 9.7Hz), 7.54 (d, 2H, J = 8.6
Hz), 7.32 (dd, 1H, J = 1,9Hz, 9.5Hz), 7.06 (s, 1H),
6.94 (d, 2H, J = 8.6Hz), 3.74 (s, 3H), 2.55 (s, 3H); MS (APCI, m / z): 371 (M + H) +, 373 (M + H) + HPLC (N); Rt = 4.1 min. (Example 82) 1- [4- [4- (6-Chloro-2-methyl-imidazo [1,2-α] pyridin-3-yl) -thiazole- 2-ylamino] -phenyl] -ethanone Using the compound of Reference Example 12 and (4-acetyl-phenyl) -thiourea (Reference Example 47), the reaction was carried out in the same manner as in Example 1 to obtain the title compound.

Mp 251-256 ° C .; 1H-NMR (DMSO-d6) δ: 10.92 (s, 1H), 9.20 (d, 1H, J
= 2.2Hz), 7.97 (d, 2H, J = 8.9Hz), 7.76 (d, 2H, J = 8.9
Hz), 7.63 (d, 1H, J = 9.5Hz), 7.35 (dd, 1H, J = 2.2Hz,
9.7Hz), 7.29 (s, 1H), 2.56 (s, 3H), 2.50 (s, 3H); MS (APCI, m / z): 383 (M + H) +, 385 (M + H) +; HPLC (N): Rt = 4.4 min. (Example 83) 4- [4- (6-Chloro-2-methyl-imidazo [1,2-α] pyridine-3)
-Yl) -thiazol-2-ylamino] -benzoic acid ethyl ester Using the compound of Reference Example 12 and 4-thioureido-ethyl benzoate (Reference Example 49), the reaction was carried out in the same manner as in Example 1, and the title compound was obtained. Obtained.

1H-NMR (DMSO-d6) δ: 10.91 (s, 1H), 9.
20 (d, 1H, J = 2.2Hz), 7.94 (d, 2H, J = 8.6Hz), 7.77
(d, 2H, J = 8.6Hz), 7.62 (d, 1H, J = 9.5Hz), 7.35 (dd,
1H, J = 2.2Hz, 9.5Hz), 7.29 (s, 1H), 4.28 (q, 1H, J =
7.0Hz), 2.56 (s, 3H), 1.31 (t, 3H, J = 7.0Hz); MS (APCI, m / z): 413 (M + H) +, 415 (M + H) +; HPLC ( N): Rt = 4.2 min. (Example 84) [4- (6-Chloro-2-methyl-imidazo [1,2-α] pyridine-3-)
Yl) -thiazol-2-yl]-(6-methoxy-pyridin-3-yl) -amine The compound of Reference Example 12 and (6-methoxy-pyridin-3)
Using -yl) -thiourea (Reference Example 43), the reaction was carried out in the same manner as in Example 1 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.34 (s, 1H), 9.
18 (d, 1H, J = 2.2Hz), 8.41 (d, 1H, J = 2.7Hz), 8.01
(dd, 1H, J = 2.7Hz, 8.6Hz), 7.60 (d, 1H, J = 9.5Hz),
7.32 (dd, 1H, J = 2.2Hz, 9.5Hz), 7.12 (s, 1H), 6.85
(d, 1H, J = 8.9Hz), 3.83 (s, 3H), 2.54 (s, 3H); MS (APCI, m / z): 372 (M + H) +, 374 (M + H) +; HPLC (N): Rt = 3.6 min. (Example 85) [4- (6-Chloro-2-methyl-imidazo [1,2-α] pyridine-3-
Yl) -thiazol-2-yl]-(4-trifluoromethyl-phenyl) -amine Example 1 was prepared using the compound of Reference Example 12 and (4-trifluoromethyl-phenyl) -thiourea (Reference Example 2).
The reaction was carried out in the same manner as in to give the title compound.

1H-NMR (DMSO-d6) δ: 10.89 (s, 1H), 9.
17 (d, 1H, J = 2.2Hz), 7.84 (d, 2H, J = 8.6Hz), 7.68
(d, 2H, J = 8.6Hz), 7.62 (d, 1H, J = 9.7Hz), 7.34 (dd,
1H, J = 2.2Hz, 9.7Hz), 7.29 (s, 1H), 2.56 (s, 3H); MS (APCI, m / z): 409 (M + H) +, 411 (M + H) +; HPLC (N): Rt = 3.8 min. (Example 86) [4- (6-Chloro-2-methyl-imidazo [1,2-α] pyridine-3-
Yl) -thiazol-2-yl] -p-tolyl-amine Using the compound of Reference Example 12 and p-tolyl-thiourea (purchased from Tokyo Chemical Industry), a reaction was carried out in the same manner as in Example 1 to obtain the title compound. Was.

1H-NMR (DMSO-d6) δ: 10.35 (s, 1H), 9.
30 (d, 1H, J = 2.2Hz), 7.60 (d, 2H, J = 9.5Hz), 7.52
(d, 2H, J = 8.6Hz), 7.32 (dd, 1H, J = 2.2Hz, 9.5Hz),
7.16 (d, 2H, J = 8.6Hz), 7.10 (s, 1H), 2.55 (s, 3H),
2.27 (s, 3H); MS (APCI, m / z): 355 (M + H) +, 357 (M + H) +; HPLC (N): Rt = 3.6 min. (Example 87) Methoxy-phenyl)-[4- (2-methyl-imidazo [1,2-
α] pyridin-3-yl) -5-phenyl-thiazol-2-yl]-
Amine The reaction was carried out in the same manner as in Example 1 using the compound of Reference Example 13 and (4-methoxy-phenyl) -thiourea (Reference Example 3) to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.27 (s, 1H), 8.
26 (d, 1H, J = 6.8Hz), 7.55-7.52 (m, 4H), 7.29-7.13
(m, 6H), 7.13-7.00 (m, 2H), 6.90-6.79 (m, 3H), 3.7
1 (s, 3H), 2.50 (s, 3H); MS (APCI, m / z): 413 (M + H) +; HPLC (N): Rt = 5.8 min. (Example 88) 1- [4 -[4- (2-Methyl-imidazo [1,2-α] pyridin-3-yl)
-5-phenyl-thiazol-2-ylamino] -phenyl] -ethanone Using the compound of Reference Example 13 and (4-acetyl-phenyl) -thiourea (Reference Example 47), a reaction was carried out in the same manner as in Example 1, The title compound was obtained.

MS (APCI, m / z): 425 (M + H) +, HPLC (N): Rt = 5.9 min. (Example 89) [4- (2-Methyl-imidazo [1,2-α] ] Pyridin-3-yl) -5-phenyl-thiazol-2-yl] -p-tolyl-amine Same as Example 1 using the compound of Reference Example 13 and p-tolyl-thiourea (purchased from Tokyo Chemical Industry). To give the title compound.

MS (APCI, m / z): 397 (M + H) +; HPLC (N): Rt = 5.0 min. (Example 90) 4- [4- (2-methyl-imidazo [1,2 -α] pyridin-3-yl) -5-
Phenyl-thiazol-2-ylamino] -ethyl benzoate
Ester Using the compound of Reference Example 13 and ethyl 4-thioureido-benzoate (Reference Example 49), the reaction was carried out in the same manner as in Example 1 to obtain the title compound.

MS (APCI, m / z): 455 (M + H) +; HPLC (N): Rt = 5.4 min. (Example 91) (6-methoxy-pyridin-3-yl)-[4- (2-methyl-imidazo
[1,2-α] pyridin-3-yl) -5-phenyl-thiazole-2-
Yl] -amine The compound of Reference Example 13 and (6-methoxy-pyridine-3)
Using -yl) -thiourea (Reference Example 43), the reaction was carried out in the same manner as in Example 1 to obtain the title compound.

MS (APCI, m / z): 414 (M + H) +, HPLC (N): Rt = 5.1 min. (Example 92) [4- (2-methyl-imidazo [1,2-α] ] Pyridin-3-yl) -5-phenyl-thiazol-2-yl]-(4-trifluoromethyl-phenyl) -amine Compound of Reference Example 13 and (4-trifluoromethyl-phenyl) -thiourea (Reference Example Example 1 using 2)
The reaction was carried out in the same manner as in to give the title compound.

MS (APCI, m / z): 451 (M + H) +, HPLC (N): Rt = 4.8 min. (Example 93) [4- (6-Bromo-2-methyl-imidazo [1 , 2-α] pyridine-3-
Yl) -thiazol-2-yl]-(4-methoxy-phenyl) -amine Using the compound of Reference Example 10 and (4-methoxy-phenyl) -thiourea (Reference Example 3), reacted in the same manner as in Example 1. To give the title compound.

1H-NMR (DMSO-d6) δ: 10.24 (s, 1H), 9.
42 (s, 1H), 7.55 (d, 2H, J = 8.1Hz), 7.38 (d, 1H, J =
9.5Hz), 7.22 (d, 1H, J = 7.8Hz), 7.05 (s, 1H), 6.96
(d, 1H, J = 8.1Hz), 3.74 (s, 3H), 2.54 (s, 3H); MS (APCI, m / z): 415 (M + H) +, 417 (M + H) +; HPLC (N): Rt = 4.1 min. (Example 94) 1- [4- [4- (6-Bromo-2-methyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2 -Ylamino] -phenyl] -ethanone The compound of Reference Example 10 and (4-acetyl-phenyl) -thiourea (Reference Example 47) were reacted in the same manner as in Example 1 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.93 (s, 1H), 9.
33 (s, 1H), 7.98 (d, 2H, J = 8.6Hz), 7.76 (d, 2H, J =
8.6Hz), 7.57 (d, 1H, J = 9.5Hz), 7.43 (d, 1H, J = 9.5H
z), 7.28 (s, 1H), 2.56 (s, 3H), 2.53 (s, 3H); MS (APCI, m / z) 427 (M + H) +, 429 (M + H) +; HPLC ( N); Rt = 4.5 min. (Example 95) [4- (6-Bromo-2-methyl-imidazo [1,2-α] pyridine-3-
Yl) -thiazol-2-yl] -p-tolyl-amine Using the compound of Reference Example 10 and p-tolyl-thiourea (purchased from Tokyo Chemical Industry), the reaction was carried out in the same manner as in Example 1 to obtain the title compound. Was.

1H-NMR (DMSO-d6) δ: 10.35 (s, 1H), 9.
42 (s, 1H), 7.57-7.52 (m, 2H), 7.40 (d, 1H, J = 9.5H
z), 7.26-7.10 (m, 4H), 2.55 (s, 3H), 2.27 (s, 3H); MS (APCI, m / z): 399 (M + H) +, 401 (M + H) + HPLC (N): Rt = 3.7 min. (Example 96) 4- [4- (6-bromo-2-methyl-imidazo [1,2-α] pyridine-3)
-Yl) -thiazol-2-ylamino] -ethyl benzoate Ester was reacted in the same manner as in Example 1 using the compound of Reference Example 10 and 4-thioureido-ethyl benzoate (Reference Example 49) to obtain the title compound. Was.

1H-NMR (DMSO-d6) δ: 10.92 (s, 1H), 9.
31 (s, 1H), 7.96 (d, 2H, J = 8.9Hz), 7.77 (d, 2H, J =
8.9Hz), 7.67 (d, 1H, J = 8.4Hz), 7.42 (dd, 1H, J = 1.6
Hz, 9.2Hz), 7.28 (s, 1H), 4.29 (q, 2H, J = 7.3Hz), 2.
56 (s, 3H), 1.31 (t, 3H, J = 7.3Hz); MS (APCI, m / z): 457 (M + H) +, 459 (M + H) +; HPLC (N): Rt = 4.1 min. (Example 97) [4- (6-Bromo-2-methyl-imidazo [1,2-α] pyridine-3-
Yl) -thiazol-2-yl]-(6-methoxy-pyridin-3-yl) -amine The compound of Reference Example 10 and (6-methoxy-pyridin-3)
Using -yl) -thiourea (Reference Example 43), the reaction was carried out in the same manner as in Example 1 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.36 (s, 1H), 9.
28 (s, 1H), 8.39 (s, 1H), 8.06-8.03 (m, 1H), 7.54
(d, 1H, J = 9.5Hz), 7.39 (d, 1H, J = 9.5Hz), 7.12 (s,
1H), 6.86 (d, 1H, J = 9.2Hz), 3.83 (s, 3H), 2.54 (s, 3
H); MS (APCI, m / z): 416 (M + H) +, 418 (M + H) +; HPLC (N): Rt = 3.6 min. (Example 98) [4- (6-bromo 2-Methyl-imidazo [1,2-α] pyridine-3-
Yl) -thiazol-2-yl]-(4-trifluoromethyl-phenyl) -amine Example 1 was prepared using the compound of Reference Example 10 and (4-trifluoromethyl-phenyl) -thiourea (Reference Example 2).
The reaction was carried out in the same manner as in to give the title compound.

1H-NMR (DMSO-d6) δ: 10.91 (s, 1H), 9.
29 (s, 1H), 7.85 (d, 2H, J = 8.6Hz), 7.70 (d, 2H, J =
8.6Hz), 7.57 (d, 1H, J = 9.5Hz), 7.42 (d, 1H, J = 9.5H
z), 7.28 (s, 1H), 2.56 (s, 3H); MS (APCI, m / z): 453 (M + H) +, 455 (M + H) +; HPLC (N): Rt = 3.8 min. (Example 99) (4-methoxy-phenyl)-[4- (2-methyl-imidazo [1,2-
α] pyridin-3-yl) -5-propyl-thiazol-2-yl]-
Amine The reaction was carried out in the same manner as in Example 1 using the compound of Reference Example 14 and (4-methoxy-phenyl) -thiourea (Reference Example 3) to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.00 (s, 1H), 8.
13 (d, 1H, J = 6.8Hz), 7.54-7.47 (m, 1H), 7.49 (d, 2
H, J = 9.2Hz), 7.28-7.22 (m, 1H), 6.91-6.84 (m, 3H),
3.69 (s, 3H), 2.30 (s, 3H), 1.55-1.47 (m, 1H), 0.
79 (t, 3H, J = 7.3 Hz); MS (APCI, m / z): 379 (M + H) +; HPLC (N): Rt = 5.4 min. (Example 100) 1- [4- [ 4- (2-methyl-imidazo [1,2-α] pyridin-3-yl)
-5-propyl-thiazol-2-ylamino] -phenyl] -ethanone Using the compound of Reference Example 14 and (4-acetyl-phenyl) -thiourea (Reference Example 47), a reaction was carried out in the same manner as in Example 1. The title compound was obtained.

MS (APCI, m / z): 391 (M + H) +; HPLC (N): Rt = 5.4 min. (Example 101) [4- (2-methyl-imidazo [1,2-α] ] Pyridin-3-yl) -5-propyl-thiazol-2-yl] -p-tolyl-amine Same as Example 1 using the compound of Reference Example 14 and p-tolyl-thiourea (purchased from Tokyo Chemical Industry). To give the title compound.

MS (APCI, m / z): 363 (M + H) +; HPLC (N): Rt = 4.8 min. (Example 102) 4- [4- (2-methyl-imidazo [1,2 -α] pyridin-3-yl) -5-
Propyl-thiazol-2-ylamino] -ethyl benzoate
Ester The reaction was carried out in the same manner as in Example 1 using the compound of Reference Example 14 and ethyl 4-thioureido-benzoate (Reference Example 49) to obtain the title compound.

MS (APCI, m / z): 421 (M + H) +; HPLC (N): Rt = 5.5 min. (Example 103) (6-methoxy-pyridin-3-yl)-[4- (2-methyl-imidazo
[1,2-α] pyridin-3-yl) -5-propyl-thiazole-2-
Yl] -amine The compound of Reference Example 14 and (6-methoxy-pyridine-3)
Using -yl) -thiourea (Reference Example 43), the reaction was carried out in the same manner as in Example 1 to obtain the title compound.

MS (APCI, m / z): 380 (M + H) +; HPLC (N): Rt = 5.0 min. (Example 104) [4- (2-methyl-imidazo [1,2-α] ] Pyridin-3-yl) -5-propyl-thiazol-2-yl]-(4-trifluoromethyl-phenyl) -amine The compound of Reference Example 14 and (4-trifluoromethyl-phenyl) -thiourea (Reference Example Example 1 using 2)
The reaction was carried out in the same manner as in to give the title compound.

MS (APCI, m / z): 417 (M + H) +; HPLC (N): Rt = 4.8 min. (Example 105) [5-isopropyl-4- (2-methyl-imidazo [1 , 2-α] pyridin-3-yl) -thiazol-2-yl]-(4-methoxy-phenyl) -amine Using the compound of Reference Example 15 and (4-methoxy-phenyl) -thiourea (Reference Example 3) Then, the reaction was carried out in the same manner as in Example 1 to obtain the title compound.

1H-NMR (CDCl3) δ: 7.99 (d, 1H, J = 7.0H
z), 7.50 (d, 2H, J = 9.2Hz), 7.15-7.05 (m, 3H), 6.80
(d, 2H, J = 8.9Hz), 6.68 (t, 1H, J = 6.8Hz), 3.81 (s,
3H), 2.94-2.89 (m, 1H), 2.43 (s, 3H), 1.81 (s, 3H),
1.16 (s, 3H); MS (APCI, m / z): 379 (M + H) +; HPLC (N): Rt = 5.1 min. (Example 106) 1- [4- [5-isopropyl-4] -(2-Methyl-imidazo [1,2-α]
Pyridin-3-yl) -thiazol-2-ylamino] -phenyl] -ethanone Using the compound of Reference Example 15 and (4-acetyl-phenyl) -thiourea (Reference Example 47), a reaction was carried out in the same manner as in Example 1. This gave the title compound.

MS (APCI, m / z): 391 (M + H) +; HPLC (N): Rt = 5.8 min. (Example 107) [5-isopropyl-4- (2-methyl-imidazo [1 , 2-α] pyridin-3-yl) -thiazol-2-yl] -p-tolyl-amine Same as Example 1 using the compound of Reference Example 15 and p-tolyl-thiourea (purchased from Tokyo Chemical Industry). Reacts to
The title compound was obtained.

MS (APCI, m / z): 363 (M + H) +; HPLC (N): Rt = 4.3 min. (Example 108) 4- [5-isopropyl-4- (2-methyl-imidazo) [1,2-α] pyridin-3-yl) -thiazol-2-ylamino] -benzoic acid ethyl ester Example 1 was prepared using the compound of Reference Example 15 and ethyl 4-thioureido-benzoate (Reference Example 49). The reaction was carried out in the same manner as in to give the title compound.

MS (APCI, m / z): 421 (M + H) +; HPLC (N): Rt = 5.2 min. (Example 109) [5-isopropyl-4- (2-methyl-imidazo [1 , 2-α] Pyridin-3-yl) -thiazol-2-yl]-(6-methoxy-pyridine
-3-yl) -amine The compound of Reference Example 15 and (6-methoxy-pyridin-3-
Example 1 using yl) -thiourea (Reference Example 43)
The reaction was carried out in the same manner as in to give the title compound.

MS (APCI, m / z): 380 (M + H) +; HPLC (N): Rt = 4.8 min. (Example 110) [5-isopropyl-4- (2-methyl-imidazo [1 , 2-α] pyridin-3-yl) -thiazol-2-yl]-(4-trifluoromethyl-phenyl) -amine The compound of Reference Example 15 and (4-trifluoromethyl-phenyl) -thiourea (Reference Example Using 2), a reaction was carried out in the same manner as in Example 1 to obtain the title compound.

MS (APCI, m / z): 417 (M + H) +; HPLC (N): Rt = 4.7 min. (Example 111) 4- [4- (2-methyl-imidazo [1,2 Using -α] pyridin-3-yl) -thiazol-2-ylamino] -benzonitrile (4-cyano-phenyl) -thiourea (Reference Example 48), the reaction was carried out in the same manner as in Example 1 to obtain the title compound. Obtained.

1H-NMR (DMSO-d6) δ: 10.98 (s, 1H), 8.
84 (d, 1H, J = 5.9Hz), 7.80-7.79 (m, 4H), 7.56 (d, 1
H, J = 8.9Hz), 7.32-7.27 (m, 2H), 7.02-6.99 (m, 1H),
2.51 (s, 3H); MS (APCI, m / z): 332 (M + H) +; HPLC (N): Rt = 6.1 min. (Example 112) 4- [4- (2,6-dimethyl -Imidazo [1,2-α] pyridin-3-yl) -thiazol-2-ylamino] -benzonitrile Performed using the compound of Reference Example 5 and (4-cyano-phenyl) -thiourea (Reference Example 48). The reaction was carried out in the same manner as in Example 1 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.10 (s, 1H), 8.
73 (s, 1H), 7.86-7.77 (m, 4H), 7.48 (d, 1H, J = 9.2H
z), 7.24 (s, 1H), 7.17 (d, 1H, J = 9.2Hz), 2.50 (s,
3H), 2.32 (s, 3H); MS (APCI, m / z): 346 (M + H) +; HPLC (N): Rt = 6.7 min. (Example 113) 4- [4- (2, 7-Dimethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-ylamino] -benzonitrile Using the compound of Reference Example 6 and (4-cyano-phenyl) -thiourea (Reference Example 48) Then, the reaction was carried out in the same manner as in Example 1 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.96 (s, 1H), 8.
74 (d, 1H, J = 7.6Hz), 7.80-7.77 (m, 4H), 7.33 (s, 1
H), 7.20 (s, 1H), 6.86-6.84 (m, 1H), 2.50 (s, 3H),
2.38 (s, 3H); MS (APCI, m / z): 346 (M + H) +; HPLC (N): Rt = 7.7 min. (Example 114) 4- [4- (2,8-dimethyl) -Imidazo [1,2-α] pyridin-3-yl) -thiazol-2-ylamino] -benzonitrile Performed using the compound of Reference Example 1 and (4-cyano-phenyl) -thiourea (Reference Example 48). The reaction was carried out in the same manner as in Example 1 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.96 (s, 1H), 8.
68 (d, 1H, J = 6.8Hz), 7.83-7.76 (m, 4H), 7.25 (s, 1
H), 7.11 (d, 1H, J = 6.8Hz), 6.89 (t, 1H, J = 7.0Hz),
2.58 (s, 3H), 2.51 (s, 3H); MS (APCI, m / z): 346 (M + H) +; HPLC (N): Rt = 6.0 min. (Example 115) 4- [4 -(6-Chloro-2-methyl-imidazo [1,2-α] pyridine-3
-Yl) -thiazol-2-ylamino] -benzonitrile Using the compound of Reference Example 12 and (4-cyano-phenyl) -thiourea (Reference Example 48), the reaction was carried out in the same manner as in Example 1, and the title compound was obtained. Obtained.

1H-NMR (DMSO-d6) δ: 11.02 (s, 1H), 9.
13 (s, 1H), 7.87-7.59 (m, 6H), 7.38-7.33 (m, 1H),
2.55 (s, 3H); MS (APCI, m / z): 366 (M + H) +, 368 (M + H) +; HPLC (N): Rt = 4.8 min. (Example 116) 4- [ 4- (2-methyl-6-trifluoromethyl-imidazo [1,2-
α] pyridin-3-yl) -thiazol-2-ylamino] -benzonitrile Using the compound of Reference Example 11 and (4-cyano-phenyl) -thiourea (Reference Example 48), a reaction was carried out in the same manner as in Example 1. This gave the title compound.

1H-NMR (DMSO-d6) δ: 11.06 (s, 1H), 9.
56 (s, 1H), 7.84-7.71 (m, 5H), 7.56 (d, 1H, J = 9.5H
z), 7.38 (s, 1H), 2.60 (s, 3H); MS (APCI, m / z): 400 (M + H) +; HPLC (N): Rt = 4.6 min. (Example 117) 4 -[4- (6-Bromo-2-methyl-imidazo [1,2-α] pyridine-3
-Yl) -thiazol-2-ylamino] -benzonitrile Using the compound of Reference Example 10 and (4-cyano-phenyl) -thiourea (Reference Example 48), the reaction was carried out in the same manner as in Example 1 to obtain the title compound. Obtained.

1H-NMR (DMSO-d6) δ: 11.03 (s, 1H), 9.
26 (s, 1H), 7.87-7.55 (m, 5H), 7.41-7.40 (m, 1H),
7.31 (s, 1H), 2.55 (s, 3H); MS (APCI, m / z): 410 (M + H) +, 412 (M + H) +; HPLC (N): Rt = 4.8 min. Example 118) 4- [5-methyl-4- (2-methyl-imidazo [1,2-α] pyridine-3
-Yl) -thiazol-2-ylamino] -benzonitrile Using the compound of Reference Example 9 and (4-cyano-phenyl) -thiourea (Reference Example 48), the reaction was carried out in the same manner as in Example 1 to obtain the title compound. Obtained.

1H-NMR (DMSO-d6) δ: 10.80 (s, 1H), 8.
18 (d, 1H, J = 5.9Hz), 7.77-7.64 (m, 4H), 7.55 (d, 1
H, J = 8.1Hz), 7.31-7.25 (m, 1H), 6.91 (t, 1H, J = 6.8
Hz), 2.32 (s, 3H), 2.25 (s, 3H); MS (APCI, m / z): 346 (M + H) +; HPLC (N): Rt = 6.1 min. (Example 119) ( 4-methoxy-phenyl)-[4- (2-methyl-6-phenyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -amine The compound of Reference Example 18 and (4 Using -methoxy-phenyl) -thiourea (Reference Example 3), the reaction was carried out in the same manner as in Example 1 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.20 (s, 1H), 9.
38 (s, 1H), 7.69-7.56 (m, 6H), 7.45-7.40 (m, 3H),
7.05 (s, 1H), 6.80 (d, 2H, J = 9.2Hz), 3.69 (s, 3H),
2.56 (s, 3H); MS (APCI, m / z): 346 (M + H) +, MS (APCI, m / z) 413 (M +
H) +; HPLC (N): Rt = 4.6 min. (Example 120) 1- [4- [4- (2-methyl-6-phenyl-imidazo [1,2-α] pyridin-3-yl) -Thiazol-2-ylamino] -phenyl] -ethanone Using the compound of Reference Example 18 and (4-acetyl-phenyl) -thiourea (Reference Example 47), the reaction was carried out in the same manner as in Example 1 to obtain the title compound. Was.

MS (APCI, m / z): 425 (M + H) +; HPLC (N): Rt = 5.0 min. (Example 121) [4- (2-methyl-6-phenyl-imidazo [1 , 2-α] pyridine-3
-Yl) -thiazol-2-yl] -p-tolyl-amine Using the compound of Reference Example 18 and p-tolyl-thiourea (purchased from Tokyo Chemical Industry), a reaction was carried out in the same manner as in Example 1, and the title compound was obtained. Obtained.

MS (APCI, m / z): 397 (M + H) +; HPLC (N): Rt = 4.9 min. (Example 122) 4- [4- (2-methyl-6-phenyl-imidazo) [1,2-α] pyridine
-3-yl) -thiazol-2-ylamino] -ethyl benzoate
Ester The reaction was carried out in the same manner as in Example 1 using the compound of Reference Example 18 and ethyl 4-thioureido-benzoate (Reference Example 49) to obtain the title compound.

MS (APCI, m / z): 455 (M + H) +; HPLC (N): Rt = 4.5 min. (Example 123) (6-methoxy-pyridin-3-yl)-[4- (2-methyl-6-phenyl-imidazo [1,2-α] pyridin-3-yl) -thiazole-2-
Yl] -amine The compound of Reference Example 18 and (6-methoxy-pyridine-3)
Using -yl) -thiourea (Reference Example 43), the reaction was carried out in the same manner as in Example 1 to obtain the title compound.

MS (APCI, m / z): 414 (M + H) +; HPLC (N): Rt = 4.3 min. (Example 124) [4- (2-methyl-6-phenyl-imidazo [1 , 2-α] pyridine-3
-Yl) -thiazol-2-yl]-(4-trifluoromethyl-phenyl) -amine Example using the compound of Reference Example 18 and (4-trifluoromethyl-phenyl) -thiourea (Reference Example 2). 1
The reaction was carried out in the same manner as in to give the title compound.

MS (APCI, m / z): 451 (M + H) +; HPLC (N): Rt = 4.3 min. (Example 125) 4- [4- (2-methyl-6-phenyl-imidazo) [1,2-α] pyridine
-3-yl) -thiazol-2-ylamino] -benzonitrile Using the compound of Reference Example 18 and (4-cyano-phenyl) -thiourea (Reference Example 48), the reaction was carried out in the same manner as in Example 1, and the reaction was carried out. The compound was obtained.

MS (APCI, m / z): 408 (M + H) +; HPLC (N): Rt = 6.3 min. (Example 126) N- (4-methoxy-phenyl) -N- [4- (2-methyl-imidazo [1,
2-α] pyridin-3-yl) -thiazol-2-yl] -acetamido (4-methoxy-phenyl)-[4- (2-methyl-imidazo [1,2-
α] pyridin-3-yl) -thiazol-2-yl] -amine (Example 3) 1.03 g (3.06 mmol) of pyridine 1
5 ml and 5 ml of acetic anhydride dissolved in 15 ml of dichloromethane
was added and the mixture was stirred at room temperature for 2 days. Ethyl acetate was added to the reaction solution, and the mixture was washed with a saturated aqueous solution of sodium hydrogen carbonate and a saturated saline solution. After the organic layer was dried over anhydrous sodium sulfate, the solvent was concentrated under reduced pressure.
Washed with ethyl ether. The obtained crystals were again finely pulverized and washed with hexane-ethyl ether to obtain 995 mg (86%) of the title compound.

Mp 167-170 ° C .; 1H-NMR (CDCl3) δ: 8.57-8.54 (m, 1H), 7.51-7.48
(m, 1H), 7.34-7.27 (m, 2H), 7.12-7.04 (m, 4H), 6.53
-6.47 (m, 1H), 3.91 (s, 3H), 2.59 (s, 3H), 2.16 (s,
3H); MS (APCI, m / z): 379 (M + H) +; HPLC (N): Rt = 6.0 min. (Example 127) 2,2,2-trifluoro-N- (4-methoxy -Phenyl) -N- [4- (2
-Methyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -acetamide The reaction was carried out in the same manner as in Example 126 using trifluoroacetic anhydride to obtain the title compound.

1H-NMR (CDCl3) δ: 8.08 (s, 1H), 7.95
(d, 1H, J = 6.6Hz), 7.62 (d, 1H, J = 8.8Hz), 7.33-7.26
(m, 3H), 6.97 (d, 2H, J = 9.2Hz), 6.87 (t, 1H, J = 6.3
Hz), 3.86 (s, 3H), 2.51 (s, 3H); MS (APCI, m / z): 433 (M + H) +; HPLC (N): Rt = 4.9 min. (Example 128) N -(4-Methoxy-phenyl) -N- [4- (2-methyl-imidazo [1,
2-α] pyridin-3-yl) -thiazol-2-yl] -benzamide Under a nitrogen stream (4-methoxy-phenyl)-[4- (2-methyl-imidazo [1,2-α] pyridin-3- 30 mg (89.0 μmol) of yl) -thiazol-2-yl] -amine (Example 3) was dissolved in 0.3 ml of pyridine and 1 ml of dichloromethane, 21 μl of benzoyl chloride was added, and the mixture was stirred at room temperature for 16 hours. Ethyl acetate was added to the reaction solution, and the mixture was washed with a saturated aqueous solution of sodium hydrogen carbonate and saturated saline. After the organic layer was dried over anhydrous sodium sulfate, the solvent was concentrated under reduced pressure. The obtained crude crystals were pulverized finely and washed with ethyl acetate to obtain 5 mg (13%) of the title compound.

1H-NMR (CDCl3) δ: 8.60 (s, 1H), 7.53
(d, 1H, J = 9.2Hz), 7.43 (dd, 2H, J = 2.9Hz, 6.8Hz), 7.
37-7.21 (m, 5H), 7.14-7.10 (m, 2H), 6.90 (d, 2H, J
= 9.1Hz), 6.53 (t, 1H, J = 6.7Hz), 3.82 (s, 3H), 2.62
(s, 3H); MS (APCI, m / z) 441 (M + H) +; HPLC (N); Rt = 5.7 min. (Example 129) 2,2,2-trifluoro-N- (4 -Hydroxy-phenyl) -N- [4-
(2-Methyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -acetamide 2,2,2-trifluoro-N- (4-methoxy-phenyl) -N- [ 4- (2
-Methyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -acetamide (Example 127) 25 mg
(57.8 micromoles) in 0.5 ml of dichloromethane
And cooled to -78 ° C. Boron tribromide 0.46
3 ml (0.463 mmol, 1.0 M dichloromethane solution) was added, the cooling bath was removed, and the mixture was stirred for 2 hours while naturally warming to room temperature. The mixture was cooled again to -78 ° C, and methanol was added to the reaction solution. Thereafter, a saturated aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by preparative thin-layer chromatography (dichloromethane / methanol = 10: 1) to obtain 22 mg (91%) of the title compound.

1H-NMR (CDCl3 + DMSO-d6) δ: 10.54 (s,
1H), 9.04 (s, 1H), 8.02 (d, 1H, J = 7.0Hz), 7.60 (d,
1H, J = 8.6Hz), 7.50-7.28 (m, 3H), 6.90-6.85 (m, 1H),
6.88 (d, 2H, J = 8.5 Hz), 2.51 (s, 3H); MS (APCI, m / z): 419 (M + H) +; HPLC (N): Rt = 5.2 min. (Example 130 ) N- [4- (2-Methyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -N-phenyl-benzamide Using the compound of Example 4, Example 128 The reaction was carried out in the same manner as in to give the title compound.

MS (APCI, m / z): 411 (M + H) +; HPLC (N): Rt = 5.2 min. (Example 131) 4-methoxy-N- (4-methoxy-phenyl) -N -[4- (2-methyl-
Imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -benzamide Using the compound of Example 4 and 4-methoxybenzoyl chloride, the reaction was carried out in the same manner as in Example 128 to give the title compound. Obtained.

1H-NMR (CDCl3) δ: 8.63 (d, 1H, J = 7.2H
z), 7.50 (d, 1H, J = 8.7Hz), 7.43 (d, 2H, J = 8.7Hz),
7.31-7.20 (m, 2H), 7.13-7.07 (m, 2H), 6.94 (d, 2H,
J = 9.0Hz), 6.75 (d, 2H, J = 8.7Hz), 6.53 (t, 1H, J = 7.
1Hz), 3.84 (s, 3H), 3.79 (s, 3H), 2.62 (s, 3H); MS (APCI, m / z) 471 (M + H) +; HPLC (N): Rt = 7.0 min. Example 132 (4-Methoxy-phenyl) -methyl- [4- (2-methyl-imidazo
[1,2-α] pyridin-3-yl) -thiazol-2-yl] -amine Under a nitrogen stream, sodium hydride, oily (containing 62%)
7.8mg and N, N-dimethylformamide 0.5ml
Was added and suspended. (4-methoxy-phenyl)-[4- (2-methyl-imidazo [1,2-α] pyridin-3-yl) -thiazole-2
A solution of 30 mg (89.0 micromol) of 1-yl] -amine (Example 3) in 1 ml of N, N-dimethylformamide was added dropwise at room temperature over 3 minutes. After stirring for 30 minutes, 22 μl (0.357 mmol) of methyl iodide was added dropwise, and the mixture was stirred for 1 hour. Saturated ammonium chloride was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by preparative thin-layer chromatography (ethyl acetate) to obtain 21 mg (66%) of the title compound.

1H-NMR (CDCl3) δ: 9.04 (d, 1H, J = 7.4H
z), 7.54 (d, 1H, J = 9.0Hz), 7.36 (d, 2H, J = 9.2Hz),
7.17 (t, 1H, J = 8.1Hz), 7.01-6.97 (m, 2H), 6.79 (t,
1H, J = 6.2Hz), 6.49 (s, 1H), 3.86 (s, 3H), 3.57 (s, 3
H), 2.61 (s, 3H); MS (APCI, m / z); 351 (M + H) +; HPLC (N): Rt = 4.3 min. (Example 133) Ethyl- (4-methoxy-phenyl) )-[4- (2-Methyl-imidazo
[1,2-α] pyridin-3-yl) -thiazol-2-yl] -amine Using ethyl iodide, the reaction was carried out in the same manner as in Example 132 to obtain the title compound.

MS (APCI, m / z): 365 (M + H) +; HPLC (N): Rt = 4.3 min. (Example 134) Benzyl- (4-methoxy-phenyl)-[4- (2 The reaction was carried out in the same manner as in Example 132 using -methyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -amine benzyl bromide to obtain the title compound.

MS (APCI, m / z): 427 (M + H) +; HPLC (N): Rt = 4.5 min. (Example 135) (4-methoxy-phenyl)-[4- (2-methyl -Imidazo [1,2-
α] pyridin-3-yl) -thiazol-2-yl] -phenethyl-
The reaction was carried out in the same manner as in Example 132 using amine (2-bromoethyl) benzene to obtain the title compound.

MS (APCI, m / z): 441 (M + H) +; HPLC (N): Rt = 4.4 min. (Example 136) 4-Methyl-N- [4- (2-methyl-imidazo) [1,2-α] pyridine-3
-Yl) -thiazol-2-yl] -benzamide 15 mg (65 micromol) of 4- (2-methyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-ylamine
18 mg of 1-hydroxybenzotriazole (0.130
Mmol) and 18 mg (0.130) of 4-methylbenzoic acid
Mmol) was dissolved in 1 ml of N, N-dimethylformamide and cooled with ice. 31 mg (0.163 mmol) of 1-ethyl-3- (dimethylaminopropyl) carbodiimide hydrochloride was added, and the mixture was stirred for 3 days while naturally warming to room temperature in an ice bath. Thereafter, a catalytic amount of 4-pyrrolidinopyridine was added, and the mixture was stirred at 65 ° C for 8 hours. Ethyl acetate was added to the reaction solution, and the mixture was washed with a saturated aqueous solution of sodium hydrogen carbonate and saturated saline. After the organic layer was dried over anhydrous sodium sulfate, the solvent was concentrated under reduced pressure, and the residue was purified by preparative thin-layer chromatography (dichloromethane / methanol = 10: 1) to obtain 6 mg (25%) of the title compound.

1H-NMR (CDCl3) δ: 8.55 (d, 1H, J = 6.7H
z), 7.88 (d, 2H, J = 8.1Hz), 7.60 (d, 1H, J = 8.8Hz),
7.28 (d, 2H, J = 7.4Hz), 7.22-7.17 (m, 1H), 7.06 (s,
1H), 6.77 (t, 1H, J = 7.5Hz), 5.20-4.50 (m, 1H), 2.5
6 (s, 3H), 2.43 (s, 3H); MS (APCI, m / z): 349 (M + H) +; HPLC (N): Rt = 5.0 min. (Example 137) 2-methyl- N- [4- (2-methyl-imidazo [1,2-α] pyridine-3
-Yl) -thiazol-2-yl] -benzamide Using 2-methylbenzoic acid, the reaction was carried out in the same manner as in Example 136 to obtain the title compound.

MS (APCI, m / z): 349 (M + H) +; HPLC (N): Rt = 4.9 min. (Example 138) 3,4-dimethoxy-N- [4- (2-methyl) Using -imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -benzamide 3,4-dimethoxybenzoic acid, the reaction was carried out in the same manner as in Example 136 to obtain the title compound. .

MS (APCI, m / z): 395 (M + H) +; HPLC (N): Rt = 6.9 min. (Example 139) 4-methoxy-N- [4- (2-methyl-imidazo) [1,2-α] pyridine
3- (3-yl) -thiazol-2-yl] -benzamide 4- (2-methyl-imidazo [1,2-α] pyridine-3-
15 mg (65.0 μmol) of yl) -thiazol-2-ylamine was dissolved in 1 ml of N, N-dimethylacetamide, and a catalytic amount of 4-pyrrolidinopyridine was added. 33 mg (0.195 mmol) of 4-methoxybenzoyl chloride was added, and the mixture was stirred at room temperature for 1 hour. Thereafter, the reaction solution was stirred at 65 ° C. for 3 hours. Ethyl acetate was added to the reaction solution,
The extract was washed with a saturated aqueous solution of sodium hydrogen carbonate and a saturated saline solution. After the organic layer was dried over anhydrous sodium sulfate, the solvent was concentrated under reduced pressure. The obtained residue was purified by preparative thin-layer chromatography (dichloromethane / methanol = 10: 1),
12 mg (51%) of the title compound were obtained.

1H-NMR (CDCl3) δ: 9.86 (s, 1H), 8.78
(d, 1H, J = 6.9Hz), 7.91 (d, 2H, J = 8.8Hz), 7.55 (d,
1H, J = 8.9Hz), 7.19 (t, 1H, J = 8.3Hz), 7.06 (s, 1H),
6.99 (t, 2H, J = 8.8Hz), 6.78 (t, 1H, J = 6.3Hz), 3.90
(s, 3H), 2.62 (s, 3H); MS (APCI, m / z): 365 (M + H) +; HPLC (N): Rt = 5.5 min. (Example 140) N- [4- (2-Methyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -3-phenyl-propionamide Using 3-phenyl-propionyl chloride, react in the same manner as in Example 139. To give the title compound.

MS (APCI, m / z): 363 (M + H) +; HPLC (N): Rt = 4.7 min. (Example 141) 2- (3-methoxy-phenyl) -N- [4- (2-methyl-imidazo [1,
Using 2-α] pyridin-3-yl) -thiazol-2-yl] -acetamido (3-methoxy-phenyl) -acetyl chloride,
The reaction was carried out in the same manner as in Example 139 to obtain the title compound.

MS (APCI, m / z): 379 (M + H) +; HPLC (N): Rt = 5.4 min. (Example 142) N- [4- (2-methyl-imidazo [1,2 Example 13 using -α] pyridin-3-yl) -thiazol-2-yl] -4-nitro-benzamide 4-nitrobenzoyl chloride.
The reaction was carried out in the same manner as in Example 9, to obtain the title compound.

MS (APCI, m / z): 380 (M + H) +; HPLC (N): Rt = 5.9 min. (Example 143) N- [4- (2-methyl-imidazo [1,2] The reaction was carried out in the same manner as in Example 139 using -α] pyridin-3-yl) -thiazol-2-yl] -3-phenyl-acrylamide 3-phenyl-acryloyl chloride to obtain the title compound.

MS (APCI, m / z): 361 (M + H) +; HPLC (N): Rt = 5.5 min. (Example 144) N- [4- (2-methyl-imidazo [1,2 The reaction was carried out in the same manner as in Example 139 using -α] pyridin-3-yl) -thiazol-2-yl] -propionamide propionyl chloride to obtain the title compound.

MS (APCI, m / z): 287 (M + H) +; HPLC (N): Rt = 4.7 min. (Example 145) Nonanoic acid [4- (2-methyl-imidazo [1,2] -α] pyridine-3-
Using yl) -thiazol-2-yl] -amide nonanoyl chloride, the reaction was carried out in the same manner as in Example 139 to obtain the title compound.

MS (APCI, m / z): 371 (M + H) +; HPLC (N): Rt = 4.3 min. (Example 146) Naphthalene-2-carboxylic acid [4- (2-methyl-imidazo) [1,2-
The reaction was carried out in the same manner as in Example 139 using α] pyridin-3-yl) -thiazol-2-yl] -amide naphthalene-2-carbonyl chloride to obtain the title compound.

MS (APCI, m / z): 385 (M + H) +; HPLC (N): Rt = 5.6 min. (Example 147) Furan-2-carboxylic acid [4- (2-methyl-imidazo) Example 13 using [1,2-α] pyridin-3-yl) -thiazol-2-yl] -amidofuran-2-carbonyl chloride
The reaction was carried out in the same manner as in Example 9, to obtain the title compound.

MS (APCI, m / z): 325 (M + H) +; HPLC (N): Rt = 5.6 min. (Example 148) 4-Butoxy-N- [4- (2-methyl-imidazo) [1,2-α] pyridine
Example 1 using -3-yl) -thiazol-2-yl] -benzamide 4-butoxy-benzoyl chloride
The reaction was carried out in the same manner as in Example 39 to obtain the title compound.

MS (APCI, m / z): 407 (M + H) +; HPLC (N): Rt = 5.3 min. (Example 149) N- [4- (2-methyl-imidazo [1,2 The same reaction as in Example 139 was carried out using -α] pyridin-3-yl) -thiazol-2-yl] -3-trifluoromethyl-benzamide 3-trifluoromethyl-benzoyl chloride to obtain the title compound. .

MS (APCI, m / z): 403 (M + H) +; HPLC (N): Rt = 4.9 min. (Example 150) 2- [4- [4- (2-methyl-imidazo [ 1,2-α] pyridin-3-yl)
-Thiazol-2-ylamino] -phenyl] -propan-2-ol 4- [4- (2-methyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-ylamino under a nitrogen stream ] -Benzoic acid ethyl ester (Example 17) 29 mg (77 micromol)
Was dissolved in anhydrous tetrahydrofuran 0.5). 0.42 ml of methylmagnesium bromide (0.383 mmol,
0.92 M tetrahydrofuran solution) at room temperature.
Stirred for hours. The reaction solution was cooled on ice, saturated ammonium chloride was added dropwise, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by preparative thin-layer chromatography (dichloromethane / methanol = 10: 1) to give the title compound (8 mg, 27%).

1H-NMR (CDCl3) δ: 8.91 (d, 1H, J = 7.0H
z), 7.66-7.48 (m, 4H), 7.37 (d, 2H, J = 8.6Hz), 7.18
(t, 1H, J = 8.9Hz), 6.80 (t, 2H, J = 6.8Hz), 6.67 (s, 1
H), 2.62 (s, 3H), 1.61 (s, 6H); MS (APCI, m / z): 365 (M + H) +; HPLC (N): Rt = 5.4 min. (Example 151) 4 -[4- (2-Methyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-ylamino] -benzoic acid 4- [4- (2-methyl-imidazo [1,2-α ] Pyridin-3-yl) -thiazol-2-ylamino] -benzoic acid ethyl ester (Example 17) (849 mg, 2.24 mmol) was dissolved in ethanol (16 ml), and sodium hydroxide (269 mg, 6.26 mg) was added.
(72 mmol) dissolved in 3 ml of water,
Stirred at 1 ° C for 1 hour. Water was added to the reaction solution, and the pH was adjusted to 7 with a 5% aqueous solution of potassium hydrogen sulfate and aqueous ammonia. The suspension was filtered and the crystals were dissolved in methanol. The solution was filtered, and the filtrate was concentrated under reduced pressure to give the title compound (577 mg).
(74%).

1H-NMR (DMSO-d6) δ: 10.82 (brs, 1H),
8.90 (d, 1H, J = 7.0Hz), 7.92 (d, 2H, J = 8.9Hz), 7.74
(d, 2H, J = 8.9Hz), 7.55 (d, 1H, J = 8.9Hz), 7.29 (t,
1H, J = 7.8Hz), 7.21 (s, 1H,), 7.00 (t, 1H, J = 6.8H
z), 2.54 (s, 3H); MS (APCI, m / z): 351 (M + H) +; HPLC (N): Rt = 5.5 min. (Example 152) N-ethyl-4- [4 -(2-Methyl-imidazo [1,2-α] pyridine-3
-Yl) -thiazol-2-ylamino] -benzamide Using the compound of Reference Example 41, the reaction was carried out in the same manner as in Example 1 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.69 (s, 1H), 8.
92 (d, 1H, J = 6.8Hz), 8.31 (brs, 1H), 7.84 (d, 2H, J
= 8.6Hz), 7.70 (d, 2H, J = 8.6Hz), 7.56 (d, 1H, J = 8.9
Hz), 7.29 (t, 1H, J = 8.9Hz), 7.18 (s, 1H,), 6.99
(t, 1H, J = 7.0Hz), 3.27 (q, 2H, J = 7.0Hz), 2.55 (s, 3
H), 1.11 (t, 3H, J = 7.0 Hz); MS (APCI, m / z): 378 (M + H) +; HPLC (N): Rt = 6.2 min. (Example 153) 4- [ Using 4- (2-methyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-ylamino] -benzamide 4-thioureidobenzamide (Reference Example 59)
The reaction was carried out in the same manner as in Example 1 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.72 (s, 1H), 8.
94 (d, 1H, J = 6.5Hz), 7.89-7.60 (m, 5H), 7.37-7.06
(m, 3H), 2.66 (s, 3H); MS (APCI, m / z): 350 (M + H) +; HPLC (N): Rt = 7.0 min. (Example 154) N-methyl-4 -[4- (2-Methyl-imidazo [1,2-α] pyridine-3
-Yl) -thiazol-2-ylamino] -benzamide Using N-methyl-4-thioureido-benzamide (Reference Example 58), the reaction was carried out in the same manner as in Example 1 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.72 (s, 1H), 8.
95 (d, 1H, J = 7.0Hz), 8.29 (d, 1H, J = 4.9Hz), 7.82
(d, 2H, J = 8.6Hz), 7.70 (d, 2H, J = 8.6Hz), 7.62 (d,
1H, J = 8.9Hz), 7.39 (t, 1H, J = 8.1Hz) 7.23 (s, 1H),
7.07 (t, 1H, J = 6.5Hz), 2.76 (d, 3H, J = 4.6Hz), 2.60
(s, 3H); MS (APCI, m / z): 364 (M + H) +; HPLC (N): Rt = 6.6 min. (Example 155) N, N-dimethyl-4- [4- ( 2-Methyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-ylamino] -benzamide The compound of Reference Example 40 was used and reacted in the same manner as in Example 1 to obtain the title compound. Was.

1H-NMR (DMSO-d6) δ: 10.65 (s, 1H), 8.
91 (d, 1H, J = 7.0Hz), 7.69 (d, 2H, J = 8.9Hz), 7.56
(d, 1H, J = 8.9Hz), 7.42 (d, 2H, J = 8.9Hz), 7.31 (t 1
H, J = 8.1Hz), 7.18 (s, 1H), 7.00 (t, 1H, J = 6.5Hz),
2.96 (s, 6H), 2.54 (s, 3H); MS (APCI, m / z): 378 (M + H) +; HPLC (N): Rt = 6.2 min. (Example 156) N-methoxy- N-methyl-4- [4- (2-methyl-imidazo [1,2-
α] pyridin-3-yl) -thiazol-2-ylamino] -benzamide Using the compound of Reference Example 42, a reaction was conducted in the same manner as in Example 1 to obtain the title compound.

MS (APCI, m / z): 394 (M + H) +; HPLC (N): Rt = 6.1 min. (Example 157) (4-methoxy-phenyl)-[4- (2-methyl -Imidazo [1,2-
α] pyridin-3-yl) -thiazol-2-yl] -amine hydrobromide 2-bromo-1- (2-methyl-imidazo [1,2-α] pyridin-3-yl) -ethanone ( Reference Example 56 12.5 mg (49.5 μmol) and (4-methoxy-phenyl) -thiourea (Reference Example 3) 9.0 mg (49.5 μmol) were dissolved in 1 ml of ethanol, and heated under reflux for 15 hours. did. Ethyl ether was added to the reaction solution, the suspension was filtered, and the crystals were washed with ethyl ether to give 19.4 mg (94%) of the title compound.
I got

1H-NMR (DMSO-d6) δ: 10.35 (s, 1H), 9.
16 (d, 1H, J = 7.1Hz), 7.98-7.93 (m, 2H), 7.55 (d, 2
H, J = 9.0Hz), 7.55-7.51 (m, 1H), 7.36 (s, 1H), 6.94
(d, 2H, J = 9.0 Hz), 3.73 (s, 3H), 2.64 (s, 3H). (Example 158) 1- [4- [4- (2-methyl-imidazo [1,2-α] ] Pyridin-3-yl)
-Thiazol-2-ylamino] -phenyl] -ethanone hydrobromide (4-acetyl-phenyl) -thiourea (Reference Example 47)
And the reaction was carried out in the same manner as in Example 157 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 11.02 (s, 1H), 9.
12 (d, 1H, J = 7.3Hz), 7.98-7.95 (m, 4H), 7.75 (d, 2
(H, J = 8.9Hz), 7.58-7.55 (m, 2H), 2.66 (s, 3H), 2.49
(Example 159) [4- (2-Methyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -p-tolyl-amine hydrobromic acid Using the salt p-tolyl-thiourea (purchased from Tokyo Chemical Industry), the reaction was carried out in the same manner as in Example 157 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.45 (s, 1H), 9.
15 (d, 1H, J = 6.8Hz), 7.96-7.93 (m, 2H), 7.52-7.50
(m, 1H), 7.51 (d, 2H, J = 8.1Hz), 7.41 (s, 1H), 7.14
(d, 2H, J = 8.1 Hz), 2.64 (s, 3H), 2.26 (s, 3H). (Example 160) 4- [4- (2-methyl-imidazo [1,2-α] pyridine- 3-yl) -thiazol-2-ylamino] -ethyl benzoate Ester hydrobromide 4-thioureido-ethyl benzoate (Reference Example 49) was used to carry out a reaction in the same manner as in Example 157 to give the title compound. Obtained.

1H-NMR (DMSO-d6) δ: 10.10 (s, 1H), 9.
11 (d, 1H, J = 7.0Hz), 7.96-7.93 (m, 4H), 7.75 (d, 2
H, J = 8.9Hz), 7.55-7.54 (m, 2H), 4.28 (q, 2H, J = 7.3
(Hz), 2.65 (s, 3H), 1.31 (t, 3H, J = 7.3 Hz). (Example 161) (6-Methoxy-pyridin-3-yl)-[4- (2-methyl-imidazo
[1,2-α] pyridin-3-yl) -thiazol-2-yl] -amine hydrobromide (6-methoxy-pyridin-3-yl) -thiourea (Reference Example 43) was used. The reaction was carried out in the same manner as in Example 157 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.47 (s, 1H), 9.
09 (d, 1H, J = 6.8Hz), 8.48 (d, 1H, J = 3.0Hz), 7.98-7.9
2 (m, 3H), 7.53-7.49 (m, 1H), 7.42 (s, 1H), 6.84
(d, 1H, J = 8.9Hz), 3.82 (s, 3H), 2.63 (s, 3H). (Example 162) [4- (2-methyl-imidazo [1,2-α] pyridine-3- Yl) -thiazol-2-yl]-(4-trifluoromethyl-phenyl) -amine hydrobromide (4-trifluoromethyl-phenyl) -thiourea (Reference Example 2) Perform the same reaction,
The title compound was obtained.

1H-NMR (DMSO-d6) δ: 10.10 (s, 1H), 9.
10 (d, 1H, J = 7.0Hz), 7.96-7.93 (m, 2H), 7.84 (d, 2
H, J = 8.9Hz), 7.69 (d, 2H, J = 8.9Hz), 7.56-7.51 (m,
2H), 2.65 (s, 3H). Example 163 4- [4- (2-methyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-ylamino] -benzonitrile Odor The reaction was carried out in the same manner as in Example 157 using hydride (4-cyano-phenyl) -thiourea (Reference Example 48) to obtain the title compound.

1H-NMR (DMSO-d6) δ: 11.11 (s, 1H), 9.
06 (d, 1H, J = 7.0Hz), 7.96-7.93 (m, 2H), 7.90-7.80
(m, 4H), 7.60 (s, 1H), 7.55-7.52 (m, 1H), 2.64 (s,
3H). (Example 164) 1- [4- [4- (8-Hydroxy-2-methyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-ylamino] -phenyl]-
Ethanone hydrobromide Example 15 was prepared using the compound of Reference Example 33 (1) and (4-acetyl-phenyl) -thiourea (Reference Example 47).
The reaction was carried out in the same manner as in Example 7 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 11.00 (s, 1H), 8.
62 (d, 1H, J = 6.8Hz), 7.95 (d, 2H, J = 8.9Hz), 7.75
(d, 2H, J = 8.9Hz), 7.56 (s, 1H), 7.40-7.35 (m, 1H),
7.21 (d, 1H, J = 7.6 Hz), 2.63 (s, 3H), 2.52 (s, 3H). (Example 165) 1- [4- [4- (7-bromo-8-hydroxy-2-) Methyl-imidazo
[1,2-α] pyridin-3-yl) -thiazol-2-ylamino]-
Phenyl] -ethanone hydrobromide Example 15 was prepared using the compound of Reference Example 33 (2) and (4-acetyl-phenyl) -thiourea (Reference Example 47).
The reaction was carried out in the same manner as in Example 7 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.97 (s, 1H), 8.
54 (d, 1H, J = 7.6Hz), 7.97 (d, 2H, J = 8.6Hz), 7.74
(d, 2H, J = 8.6Hz), 7.54-7.49 (m, 2H), 2.61 (s, 3H),
2.50 (s, 3H). (Example 166) 1- [4- [4- (2-methoxymethyl-imidazo [1,2-α] pyridine)
-3-yl) -thiazol-2-ylamino] -phenyl] -ethanone hydrobromide Using the compound of Reference Example 34 and (4-acetyl-phenyl) -thiourea (Reference Example 47), The reaction was performed in the same manner to obtain the title compound.

1H-NMR (DMSO-d6) δ: 11.02 (s, 1H), 9.
14 (d, 1H, J = 6.8Hz), 7.98-7.92 (m, 4H), 7.75 (d, 2
H, J = 8.9Hz), 7.55-7.52 (m, 2H), 4.81 (s, 2H), 3.42
(s, 3H), 2.51 (s, 3H). (Example 167) [4- (2-Methoxymethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -p -Tolyl-amine hydrobromide Using the compound of Reference Example 34 and p-tolyl-thiourea (purchased from Tokyo Chemical Industry), a reaction was carried out in the same manner as in Example 157 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.45 (s, 1H), 9.
17 (d, 1H, J = 7.0Hz), 7.94-7.93 (m, 2H), 7.54-7.49
(m, 1H), 7.52 (d, 2H, J = 8.4Hz), 7.36 (s, 1H), 7.15
(d, 2H, J = 8.4Hz), 4.81 (s, 2H), 3.42 (s, 3H), 2.26
(s, 3H): (Example 168) [4- (2-Methoxymethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl]-(6-methoxy-pyridine-3) -Yl) -amine hydrobromide Compound of Reference Example 34 and (6-methoxy-pyridine-3)
The reaction was carried out in the same manner as in Example 157 using -yl) -thiourea (Reference Example 43) to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.48 (s, 1H), 9.
12 (d, 1H, J = 7.0Hz), 8.48 (d, 1H, J = 2.4Hz), 7.99-
7.94 (m, 3H), 7.55-7.50 (m, 1H), 7.39 (s, 1H), 6.84
(d, 1H, J = 8.9Hz), 4.80 (s, 2H), 3.82 (s, 3H), 3.41
(s, 3H). (Example 169) [4- (2-Methoxymethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl]-(4-trifluoromethyl-phenyl Example 1 using the compound of Reference Example 34 and (4-trifluoromethyl-phenyl) -thiourea (Reference Example 2).
The reaction was carried out in the same manner as in 57 to give the title compound.

1H-NMR (DMSO-d6) δ: 10.97 (s, 1H), 9.
11 (d, 1H, J = 6.5Hz), 7.92-7.83 (m, 4H), 7.70 (d, 2
H, J = 8.6Hz), 7.52-7.50 (m, 2H), 4.80 (s, 2H), 3.42
(s, 3H). Example 170 [4- (2-Ethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl]-(4-methoxy-phenyl) -amine Hydrobromide Using the compound of Reference Example 37 and (4-methoxy-phenyl) -thiourea (Reference Example 3), the reaction was carried out in the same manner as in Example 157 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.34 (s, 1H), 9.
08 (d, 1H, J = 6.8Hz), 7.98-7.96 (m, 2H), 7.56-7.51
(m, 1H), 7.54 (d, 2H, J = 9.2Hz), 7.36 (s, 1H), 6.93
(d, 2H, J = 9.2Hz), 3.73 (s, 3H), 3.02 (q, 2H, J = 7.6H
z), 1.36 (t, 3H, J = 7.6 Hz). (Example 171) 1- [4- [4- (2-ethyl-imidazo [1,2-α] pyridin-3-yl)
-Thiazol-2-ylamino] -phenyl] -ethanone Using the compound of Reference Example 37 and (4-acetyl-phenyl) -thiourea (Reference Example 47), the reaction was carried out in the same manner as in Example 157 to obtain the title compound. Was.

1H-NMR (DMSO-d6) δ: 11.03 (s, 1H), 9.
05 (d, 1H, J = 7.0Hz), 8.01-7.93 (m, 4H), 7.75 (d, 2
H, J = 8.1Hz), 7.58-7.55 (m, 2H), 3.05 (q, 2H, J = 7.6
(Hz), 2.50 (s, 3H), 1.37 (t, 3H, J = 7.6 Hz). (Example 172) [4- (2-ethyl-imidazo [1,2-α] pyridin-3-yl)- Thiazol-2-yl] -p-tolyl-amine hydrobromide Using the compound of Reference Example 37 and p-tolyl-thiourea (purchased from Tokyo Chemical Industry), a reaction was conducted in the same manner as in Example 157, and the title compound was obtained. I got

1H-NMR (DMSO-d6) δ: 10.44 (s, 1H), 9.
08 (d, 1H, J = 7.0Hz), 7.98-7.92 (m, 2H), 7.56-7.50
(m, 3H), 7.40 (s, 1H), 7.14 (d, 2H, J = 8.4Hz), 3.03
(q, 2H, J = 7.6Hz), 2.26 (s, 3H), 1.36 (t, 3H, J = 7.6Hz)
(Example 173) 4- [4- (2-ethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-ylamino] -benzoic acid ethyl ester hydrobromide Reference Using the compound of Example 37 and 4-thioureido-ethyl benzoate (Reference Example 49), the reaction was carried out in the same manner as in Example 157 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 11.02 (s, 1H), 9.
05 (d, 1H, J = 6.8Hz), 8.02-7.91 (m, 4H), 7.77 (d, 2
H, J = 8.6Hz), 7.57-7.54 (m, 2H), 4.27 (q, 2H, J = 7.0
Hz), 3.04 (q, 2H, J = 7.6Hz), 1.37 (t, 3H, J = 7.6Hz),
1.31 (t, 3H, J = 7.0 Hz). (Example 174) [4- (2-Ethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl]-(6- Methoxy-pyridin-3-yl) -amine hydrobromide Compound of Reference Example 37 and (6-methoxy-pyridin-3)
The reaction was carried out in the same manner as in Example 157 using -yl) -thiourea (Reference Example 43) to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.48 (s, 1H), 9.
03 (d, 1H, J = 6.8Hz), 8.48 (d, 1H, J = 2.4Hz), 8.00-
7.93 (m, 3H), 7.56-7.42 (m, 1H), 7.39 (s, 1H), 6.8
3 (d, 1H, J = 8.6Hz), 3.81 (s, 3H), 3.01 (q, 2H, J = 7.
Example 175) [4- (2-Ethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl]-(6 Hz), 1.35 (t, 3H, J = 7.6 Hz). (4-trifluoromethyl-phenyl) -amine hydrobromide Example 1 was prepared using the compound of Reference Example 37 and (4-trifluoromethyl-phenyl) -thiourea (Reference Example 2).
The reaction was carried out in the same manner as in 57 to give the title compound.

1H-NMR (DMSO-d6) δ: 11.01 (s, 1H), 9.
04 (d, 1H, J = 7.0Hz), 8.00-7.94 (m, 2H), 7.84 (d, 2
H, J = 8.4Hz), 7.68 (d, 2H, J = 8.4Hz), 7.59-7.53 (m,
2H), 3.03 (q, 2H, J = 7.6 Hz), 1.37 (t, 3H, J = 7.6 Hz); MS (APCI, m / z): 470 (M + H) +. (Example 176) 4 -[4- (2-Ethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-ylamino] -benzonitrile hydrobromide Compound of Reference Example 37 and (4-cyano-phenyl Using) -thiourea (Reference Example 48), the reaction was carried out in the same manner as in Example 157 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 11.13 (s, 1H), 9.
00 (d, 1H, J = 7.0Hz), 8.01-7.93 (m, 2H), 7.88-7.67
(m, 4H), 7.60 (s, 1H), 7.56-7.51 (m, 1H), 3.02 (q,
2H, J = 7.6Hz), 1.36 (t, 3H, J = 7.6Hz); MS (APCI, m / z): 427 (M + H) +. (Example 177) 3- [2- (4- Methoxy-phenylamino) -thiazol-4-yl] -imidazo [1,2-α] pyridine-2-carboxylic acid methyl ester hydrobromide Compound of Reference Example 39 and (4-methoxy-phenyl) -thiourea ( Using Reference Example 3), the reaction was carried out in the same manner as in Example 157 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.24 (s, 1H), 8.
87 (d, 1H, J = 7.3Hz), 7.78 (d, 1H, J = 8.9Hz), 7.65-
7.59 (m, 1H), 7.54-7.51 (m, 3H), 7.25-7.20 (m, 1
H), 6.93-6.90 (m, 2H), 3.86 (s, 3H), 3.72 (s, 3H). (Example 178) 3- [2- (4-acetyl-phenylamino) -thiazol-4-yl ] -Imidazo [1,2-α] pyridine-2-carboxylic acid methyl ester hydrobromide Example 157 was prepared using the compound of Reference Example 39 and (4-acetyl-phenyl) -thiourea (Reference Example 47). The reaction was carried out in the same manner as in to give the title compound.

1H-NMR (DMSO-d6) δ: 10.94 (s, 1H), 8.
83 (d, 1H, J = 7.0Hz), 7.94 (d, 2H, J = 8.9Hz), 7.82-
7.62 (m, 5H), 7.28-7.23 (m, 1H), 3.86 (s, 3H), 2.5
0 (s, 3H). (Example 179) 3- (2-p-tolylamino-thiazol-4-yl) -imidazo [1,
2-α] pyridine-2-carboxylic acid methyl ester hydrobromide Using the compound of Reference Example 39 and p-tolyl-thiourea (purchased from Tokyo Chemical Industry), a reaction was conducted in the same manner as in Example 157, and the title compound was obtained. I got

1H-NMR (DMSO-d6) δ: 10.36 (s, 1H), 8.
87 (d, 1H, J = 7.0Hz), 7.78 (d, 1H, J = 9.2Hz), 7.67-
7.61 (m, 1H), 7.55-7.48 (m, 3H), 7.26-7.21 (m, 1
H), 7.12 (d, 2H, J = 7.8Hz), 3.86 (s, 3H), 2.25 (s, 3
H). (Example 180) 3- [2- (4-ethoxycarbonyl-phenylamino) -thiazol-4-yl] -imidazo [1,2-α] pyridine-2-carboxylic acid methyl ester hydrobromic acid Salt Using the compound of Reference Example 39 and ethyl 4-thioureido-benzoate (Reference Example 49), the reaction was carried out in the same manner as in Example 157 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.91 (s, 1H), 8.
82 (d, 1H, J = 7.0Hz), 7.91 (d, 2H, J = 8.6Hz), 7.81-
7.61 (m, 5H), 7.27-7.22 (m, 1H), 4.27 (q, 2H, J = 7.
0 Hz), 3.86 (s, 3H), 1.30 (t, 3H, J = 7.0 Hz). (Example 181) 3- [2- (6-Methoxy-pyridin-3-ylamino) -thiazole
-4-yl] -imidazo [1,2-α] pyridine-2-carboxylic acid methyl ester hydrobromide Compound of Reference Example 39 and (6-methoxy-pyridine-3)
The reaction was carried out in the same manner as in Example 157 using -yl) -thiourea (Reference Example 43) to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.37 (s, 1H), 8.
81 (d, 1H, J = 7.3Hz), 8.45 (d, 1H, J = 3.0Hz), 7.95
(dd, 1H, J = 3.0Hz, 8.9Hz), 7.77 (d, 1H, J = 9.2Hz),
7.64-7.59 (m, 1H), 7.54 (s, 1H), 7.24-7.19 (m, 1H),
6.82 (d, 1H, J = 8.6 Hz), 3.85 (s, 3H), 3.81 (s, 3H). (Example 182) 3- [2- (4-trifluoromethyl-phenylamino) -thiazole-4 -Yl] -imidazo [1,2-α] pyridine-2-carboxylic acid methyl ester hydrobromide Using the compound of Reference Example 39 and (4-trifluoromethyl-phenyl) -thiourea (Reference Example 2). Example 1
The reaction was carried out in the same manner as in 57 to give the title compound.

1H-NMR (DMSO-d6) δ: 10.91 (s, 1H), 8.
81 (d, 1H, J = 7.0Hz), 7.83-7.79 (m, 3H), 7.69-7.63
(m, 4H), 7.29-7.24 (m, 1H), 3.86 (s, 3H). (Example 183) 3- [2- (4-cyano-phenylamino) -thiazol-4-yl]-
Imidazo [1,2-α] pyridine-2-carboxylic acid methyl ester hydrobromide Same as Example 157 using the compound of Reference Example 39 and (4-cyano-phenyl) -thiourea (Reference Example 48). To give the title compound.

1H-NMR (DMSO-d6) δ: 11.01 (s, 1H), 8.
74 (d, 1H, J = 7.0Hz), 7.81-7.73 (m, 5H), 7.69 (s, 1
H), 7.64-7.57 (m, 1H), 7.22-7.18 (m, 1H), 3.84 (s,
3H). (Example 184) [4- (2-Methyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -naphthalen-1-yl-amine naphthalen-1-yl The reaction was carried out in the same manner as in Example 1 using -thiourea to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.29 (s, 1H), 8.
94 (d, 1H, J = 6.6Hz), 8.30 (d, 1H, J = 7.1Hz), 8.13
(t 1H, J = 7.2Hz), 7.97 (d, 1H, J = 9.4Hz), 7.71 (d, 1
H, J = 8.1Hz), 7.63-7.51 (m 4H), 7.25 (t, 1H, J = 6.5H
z), 7.08 (s, 1H), 6.88 (t, 1H, J = 6.6Hz), 2.53 (s, 3
H); MS (APCI, m / z): 357 (M + H) +; HPLC (N): Rt = 4.7 min. (Example 185) (2,4-dimethoxy-phenyl)-[4- (2 -Methyl-imidazo [1,
Using 2-α] pyridin-3-yl) -thiazol-2-yl] -amine (2,4-dimethoxy-phenyl) -thiourea, the reaction was carried out in the same manner as in Example 1 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 9.44 (s, 1H), 8.9
7 (d, 1H, J = 6.2Hz), 7.91 (t, 1H, J = 7.1Hz), 7.52 (d,
1H, J = 8.9Hz), 7.26 (t, 1H, J = 6.6Hz), 6.96-6.93 (m
2H), 6.66 (d, 1H, J = 2.7Hz), 6.53 (dd, 1H, J = 2.7H
z, 8.9Hz), 3.85 (s, 3H), 3.76 (s, 3H), 2.50 (s, 3
H); MS (APCI, m / z) 367 (M + H) +; HPLC (N): Rt = 4.9 min. (Example 186) [4- (2-methyl-imidazo [1,2-α] Reaction was carried out in the same manner as in Example 1 using (pyridin-3-yl) -thiazol-2-yl]-(4-nitro-phenyl) -amine (4-nitro-phenyl) -thiourea to obtain the title compound. Was.

1H-NMR (DMSO-d6) δ: 11.26 (s, 1H), 8.
83 (d, 1H, J = 6.7Hz), 8.25 (d, 2H, J = 9.3Hz), 7.86
(d, 2H, J = 9.3Hz), 7.57 (d, 1H, J = 9.3Hz), 7.33 (s,
1H), 7.32-7.28 (m, 1H), 7.01 (t, 1H, J = 6.6Hz), 2.54
(s, 3H); MS (APCI, m / z): 352 (M + H) +; HPLC (N): Rt = 6.2 min. (Example 187) (3,4-dichloro-phenyl)-[4 -(2-Methyl-imidazo [1,2-
Using [α] pyridin-3-yl) -thiazol-2-yl] -amine (3,4-dichloro-phenyl) -thiourea, the reaction was carried out in the same manner as in Example 1 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.77 (s, 1H), 8.
92 (d, 1H, J = 7.1Hz), 8.25 (d, 1H, J = 2.7Hz), 7.57
(d, 2H, J = 8.8Hz), 7.43 (dd, 1H, J = 2.6Hz, 8.8Hz),
7.31 (t, 1H, J = 7.2Hz), 7.22 (s, 1H), 6.99 (t, 1H,
J = 6.7Hz), 2.55 (s, 3H); MS (APCI, m / z): 375 (M + H) +, 377 (M + H) +; HPLC (N): Rt = 5.0 min. Example 188) (4-Methoxy-phenyl)-[4- (2-trifluoromethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl]-
Amine 2-bromo-1- (2-trifluoromethyl-imidazo [1,2-α]
15.2 mg of (pyridin-3-yl) -ethanone (Reference Example 20)
(49.5 μmol) and 9.0 mg (49.5 μmol) of (4-methoxy-phenyl) -thiourea (Reference Example 3) were dissolved in 1 ml of ethanol and heated under reflux for 15 hours. Tetrahydrofuran and methanol are added to the reaction solution to dissolve the suspension, and tris- (2-aminoethyl)-
Amine polystyrene HL resin 50mg (122
Micromol, 2.43 mmol / g) and stirred at room temperature for 3 minutes. The reaction solution was filtered, and the filtrate was concentrated under reduced pressure. The obtained crystals were pulverized finely and washed with hexane-ethyl ether to obtain 14 mg (73%) of the title compound.

Mp 176-177 ° C .; 1H-NMR (DMSO-d6) δ: 10.25 (s, 1H), 8.66 (d, 1H, J
= 5.9Hz), 7.78 (d, 1H, J = 9.2Hz), 7.56-7.48 (m, 3H),
7.20 (s, 1H), 7.18-7.13 (m, 1H), 6.94-6.88 (m, 1
H), 3.72 (s, 3H); MS (APCI, m / z): 391 (M + H) +; HPLC (N): Rt = 4.1 min. (Example 189) 1- [4- [4- (2-trifluoromethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-ylamino] -phenyl] -ethanone The compound of Reference Example 20 and (4-acetyl-phenyl) -thiourea (reference Using Example 47), a reaction was carried out in the same manner as in Example 188 to obtain the title compound.

Mp 179-181 ° C .; 1H-NMR (DMSO-d6) δ: 10.93 (s, 1H), 8.65 (d, 1H, J
= 7.0Hz), 7.94 (d, 2H, J = 8.9Hz), 7.80 (d, 1H, J = 8.9
Hz), 7.75 (d, 2H, J = 8.9Hz), 7.57-7.50 (m, 1H), 7.43
(s, 1H), 7.21-7.15 (m, 1H), 2.51 (s, 3H); MS (APCI, m / z): 403 (M + H) +; HPLC (N): Rt = 4.6 min. Example 190) p-Tolyl- [4- (2-trifluoromethyl-imidazo [1,2-α]
Pyridin-3-yl) -thiazol-2-yl] -amine Using the compound of Reference Example 20 and p-tolyl-thiourea (purchased from Tokyo Chemical Industry), a reaction was carried out in the same manner as in Example 188 to obtain the title compound. Was.

1H-NMR (DMSO-d6) δ: 10.34 (s, 1H), 8.
66 (d, 1H, J = 7.3Hz), 7.79 (d, 1H, J = 8.9Hz), 7.53
(d, 1H, J = 6.8Hz), 7.50 (d, 2H, J = 8.9Hz), 7.25 (s,
1H), 7.18-7.10 (m, 3H), 2.24 (s, 3H); MS (APCI, m / z): 375 (M + H) +; HPLC (N): Rt = 3.7 min. (Example 191) ) 4- [4- (2-Trifluoromethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-ylamino] -benzoic acid ethyl ester The compound of Reference Example 20 and 4-thioureido-benzoic acid The reaction was carried out in the same manner as in Example 188 using ethyl acetate (Reference Example 49) to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.93 (s, 1H), 8.
65 (d, 1H, J = 6.2Hz), 7.92-7.88 (m, 2H), 7.82-7.73
(m, 3H), 7.56-7.53 (m, 1H), 7.42 (d, 1H, J = 2.4Hz),
7.18-7.16 (m, 1H), 4.26 (m, 2H), 1.30 (m, 3H); MS (APCI, m / z): 433 (M + H) +; HPLC (N): Rt = 4.1 min. Example 192 (6-Methoxy-pyridin-3-yl)-[4- (2-trifluoromethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2
-Yl] -amine The compound of Reference Example 20 and (6-methoxy-pyridine-3)
The reaction was carried out in the same manner as in Example 188 using -yl) -thiourea (Reference Example 43) to obtain the title compound.

Mp 188-191 ° C .; 1H-NMR (DMSO-d6) δ: 10.39 (s, 1H), 8.63 (d, 1H, J
= 6.8Hz), 8.44 (d, 1H, J = 2.7Hz), 7.97 (dd, 1H, J = 2.
7Hz, 8.9Hz), 7.78 (d, 1H, J = 9.2Hz), 7.54-7.49 (m,
1H), 7.27 (s, 1H), 7.18-7.13 (m, 1H), 6.81 (d, 1H,
J = 8.9 Hz), 3.80 (s, 3H); MS (APCI, m / z): 392 (M + H) +; HPLC (N): Rt = 3.7 min. (Example 193) [4- (2 -Trifluoromethyl-imidazo [1,2-α] pyridine-
3-yl) -thiazol-2-yl]-(4-trifluoromethyl-
Example 1 using the compound of Reference Example 20 and (4-trifluoromethyl-phenyl) -thiourea (Reference Example 2).
The reaction was carried out in the same manner as in 88 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.91 (s, 1H), 8.
62 (d, 1H, J = 7.0Hz), 7.85-7.23 (m, 3H), 7.67 (d, 2
(H, J = 8.6Hz), 7.61-7.51 (m, 1H), 7.42 (s, 1H), 7.17
(t, 1H, J = 6.8 Hz); MS (APCI, m / z): 429 (M + H) +; HPLC (N): Rt = 3.9 min. (Example 194) 4- [4- (2 -Trifluoromethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-ylamino] -benzonitrile The compound of Reference Example 20 and (4-cyano-phenyl) -thiourea (Reference Example 48) The reaction was carried out in the same manner as in Example 188 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 11.03 (s, 1H), 8.
60 (d, 1H, J = 7.3Hz), 7.82-7.72 (m, 5H), 7.57-7.51
(m, 1H), 7.47 (s, 1H), 7.17 (t, 1H, J = 6.8Hz); MS
(APCI, m / z): 386 (M + H) +; HPLC (N): Rt = 5.1 min. (Example 195) (4-methoxy-phenyl)-[4- (2-phenyl-imidazo [1 , 2-
α] pyridin-3-yl) -thiazol-2-yl] -amine Using the compound of Reference Example 21 and (4-methoxy-phenyl) -thiourea (Reference Example 3), a reaction was carried out in the same manner as in Example 188. The title compound was obtained.

1H-NMR (DMSO-d6) δ: 10.21 (s, 1H), 8.
44 (d, 1H, J = 8.4Hz), 7.76 (d, 2H, J = 8.1Hz), 7.67
(d, 1H, J = 8.6Hz), 7.50 (d, 2H, J = 8.1Hz), 7.39-7.32
(m, 4H), 7.02-6.98 (m, 1H), 7.00 (s, 1H), 6.84 (d,
2H, J = 9.2Hz), 3.70 (s, 3H); MS (APCI, m / z): 399 (M + H) +; HPLC (N): Rt = 4.2 min. (Example 196) 1- [ 4- [4- (2-phenyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-ylamino] -phenyl] -ethanone The compound of Reference Example 21 and (4-acetyl-phenyl)- The reaction was carried out in the same manner as in Example 188 using thiourea (Reference Example 47) to obtain the title compound.

MS (APCI, m / z): 411 (M + H) +; HPLC (N): Rt = 4.7 min. (Example 197) [4- (2-phenyl-imidazo [1,2-α] ] Pyridin-3-yl) -thiazol-2-yl] -p-tolyl-amine Using the compound of Reference Example 21 and p-tolyl-thiourea (purchased from Tokyo Chemical Industry), a reaction was carried out in the same manner as in Example 188. The title compound was obtained.

MS (APCI, m / z): 383 (M + H) +; HPLC (N): Rt = 3.7 min. (Example 198) 4- [4- (2-phenyl-imidazo [1,2] -α] pyridin-3-yl)-
Thiazol-2-ylamino] -benzoic acid ethyl ester Using the compound of Reference Example 21 and 4-thioureido-ethyl benzoate (Reference Example 49), the reaction was carried out in the same manner as in Example 188 to obtain the title compound.

MS (APCI, m / z): 441 (M + H) +; HPLC (N): Rt = 4.2 min. (Example 199) (6-methoxy-pyridin-3-yl)-[4- (2-phenyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -amine The compound of Reference Example 21 and (6-methoxy-pyridin-3)
The reaction was carried out in the same manner as in Example 188 using -yl) -thiourea (Reference Example 43) to obtain the title compound.

MS (APCI, m / z): 400 (M + H) +; HPLC (N): Rt = 3.8 min. (Example 200) [4- (2-phenyl-imidazo [1,2-α] ] Pyridin-3-yl) -thiazol-2-yl]-(4-trifluoromethyl-phenyl)-
Amine Example 1 was prepared using the compound of Reference Example 21 and (4-trifluoromethyl-phenyl) -thiourea (Reference Example 2).
The reaction was carried out in the same manner as in 88 to obtain the title compound.

MS (APCI, m / z): 437 (M + H) +; HPLC (N): Rt = 3.9 min. (Example 201) 4- [4- (2-phenyl-imidazo [1,2 -α] pyridin-3-yl)-
Thiazol-2-ylamino] -benzonitrile Using the compound of Reference Example 21 and (4-cyano-phenyl) -thiourea (Reference Example 48), the reaction was carried out in the same manner as in Example 188 to obtain the title compound.

MS (APCI, m / z): 394 (M + H) +; HPLC (N): Rt = 5.1 min. (Example 202) 7-bromo-3- [2- (4-methoxy-phenyl) Amino) -thiazol-4-yl] -2-methyl-imidazo [1,2-α] pyridin-8-ylamine 1- (8-amino-7-bromo-2-methyl-imidazo [1,2-α] Pyridin-3-yl) -2-bromo-ethanone (Reference Example 24) 1
8 mg (51.9 μmol) and 9.5 mg (51.9) of (4-methoxy-phenyl) -thiourea (Reference Example 3)
(Micromol) was dissolved in 1 ml of ethanol and heated under reflux for 20 hours. Ethyl ether was added to the reaction solution, the suspension was filtered, the crystals were washed with ethyl ether, and then dissolved in a mixture of 1 ml of tetrahydrofuran and 1 ml of methanol, and 50 mg of tris- (2-aminoethyl) -amine polystyrene HL resin ( 122 micromolar,
(2.43 mmol / g) and stirred at room temperature for 3 minutes. The reaction solution was filtered, and the filtrate was concentrated under reduced pressure. The obtained crystals were finely ground and washed with hexane-ethyl ether to give the title compound (12.4 mg, 56%).

1H-NMR (DMSO-d6) δ: 10.16 (s, 1H), 8.
20 (d, 1H, J = 7.6Hz), 7.53 (d, 2H, J = 9.2Hz), 6.97
(d, 2H, J = 9.2Hz), 6.91 (d, 2H, J = 1.9Hz), 5.72 (s,
2H), 3.73 (s, 3H), 2.51 (s, 3H); MS (APCI, m / z): 430 (M + H) +, 432 (M + H) +, HPLC (N): Rt = 4.3 min. (Example 203) 7-bromo-2-methyl-3- [2- (4-trifluoromethyl-phenylamino) -thiazol-4-yl] -imidazo [1,2-α] pyridine-8- Reaction was carried out in the same manner as in Example 202 using ylamine (4-trifluoromethyl-phenyl) -thiourea (Reference Example 2).
The title compound was obtained.

1H-NMR (DMSO-d6) δ: 10.82 (s, 1H), 8.
12 (d, 1H, J = 7.6Hz), 7.83 (d, 2H, J = 8.9Hz), 7.68
(d, 2H, J = 8.9Hz), 7.20 (s, 1H), 6.97 (d, 1H, J = 8.6
Hz), 5.74 (s, 2H), 2.50 (s, 3H); MS (APCI, m / z): 468 (M + H) +, 470 (M + H) +; HPLC (N): Rt = 4.0 min. (Example 204) (4-imidazo [1,2-α] pyridin-3-yl-thiazol-2-yl)-(4-methoxy-phenyl) -amine The compound of Reference Example 25 and (4-methoxy Using -phenyl) -thiourea (Reference Example 3), the reaction was carried out in the same manner as in Example 202 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.20 (s, 1H), 9.
19 (d, 1H, J = 7.0Hz), 8.07 (s, 1H), 7.70 (d, 1H, J =
8.9Hz), 7.55 (d, 2H, J = 8.9Hz), 7.40 (t, 1H, J = 7.3H
z), 7.25 (s, 1H), 7.10 (t, 1H, J = 7.0Hz), 6.96 (d, 2
H, J = 8.9 Hz), 3.74 (s, 3H); MS (APCI, m / z): 323 (M + H) +; HPLC (N): Rt = 5.3 min. (Example 205) 1- [ 4- (4-imidazo [1,2-α] pyridin-3-yl-thiazole
(-2-ylamino) -phenyl] -ethanone Using the compound of Reference Example 25 and (4-acetyl-phenyl) -thiourea (Reference Example 47), the reaction was carried out in the same manner as in Example 202 to obtain the title compound.

MS (APCI, m / z): 335 (M + H) +; HPLC (N): Rt = 5.6 min. (Example 206) 4-imidazo [1,2-α] pyridin-3-yl -Thiazol-2-yl) -p-tolyl-amine Using the compound of Reference Example 25 and p-tolyl-thiourea (purchased from Tokyo Chemical Industry), a reaction was carried out in the same manner as in Example 202 to obtain the title compound.

MS (APCI, m / z): 307 (M + H) +; HPLC (N): Rt = 4.8 min. (Example 207) 4- (4-imidazo [1,2-α] pyridine- 3-yl-thiazole-2-
(Ilamino) -benzoic acid ethyl ester Using the compound of Reference Example 25 and 4-thioureido-ethyl benzoate (Reference Example 49), the reaction was carried out in the same manner as in Example 202 to obtain the title compound.

MS (APCI, m / z): 365 (M + H) +; HPLC (N): Rt = 5.0 min. (Example 208) (4-imidazo [1,2-α] pyridine-3- Yl-thiazol-2-yl)-(6-methoxy-pyridin-3-yl) -amine The compound of Reference Example 25 and (6-methoxy-pyridin-3)
The reaction was carried out in the same manner as in Example 202 using -yl) -thiourea (Reference Example 43) to obtain the title compound.

MS (APCI, m / z): 324 (M + H) +; HPLC (N): Rt = 4.7 min. (Example 209) (4-imidazo [1,2-α] pyridine-3- Il-thiazol-2-yl)-(4-trifluoromethyl-phenyl) -amine Example 2 was prepared using the compound of Reference Example 25 and (4-trifluoromethyl-phenyl) -thiourea (Reference Example 2).
Reaction was carried out in the same manner as in Example 02 to obtain the title compound.

MS (APCI, m / z): 361 (M + H) +; HPLC (N): Rt = 4.6 min. (Example 210) 4- (4-imidazo [1,2-α] pyridine- 3-yl-thiazole-2-
(Illamino) -benzonitrile Using the compound of Reference Example 25 and (4-cyano-phenyl) -thiourea (Reference Example 48), the reaction was carried out in the same manner as in Example 202 to obtain the title compound.

MS (APCI, m / z): 318 (M + H) +: HPLC (N): Rt = 5.8 min. (Example 211) [4- (8-benzyloxy-2-methyl-imidazo [ 1,2-α] pyridin-3-yl) -thiazol-2-yl]-(4-methoxy-phenyl) -amine The compound of Reference Example 28 and (4-methoxy-phenyl) -thiourea (Reference Example 3) The reaction was carried out in the same manner as in Example 202 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.16 (s, 1H), 8.
56 (d, 1H, J = 6.5Hz), 7.55-7.51 (m, 4H), 7.46-7.37
(m, 3H), 7.00 (s, 1H), 6.92 (d, 2H, J = 8.9Hz), 6,87
-6.78 (m, 2H), 5.31 (s, 2H), 3.73 (s, 3H) 2.50 (s,
3H); MS (APCI, m / z): 443 (M + H) +; HPLC (N): Rt = 8.0 min. (Example 212) 1- [4- [4- (8-benzyloxy-2) -Methyl-imidazo [1,2-
α] pyridin-3-yl) -thiazol-2-ylamino] -phenyl] -ethanone In the same manner as in Example 202, using the compound of Reference Example 28 and (4-acetyl-phenyl) -thiourea (Reference Example 47). The reaction was performed to obtain the title compound.

MS (APCI, m / z): 455 (M + H) +; HPLC (N): Rt = 7.2 min. (Example 213) [4- (8-benzyloxy-2-methyl-imidazo [ 1,2-α] pyridin-3-yl) -thiazol-2-yl] -p-tolyl-amine Using the compound of Reference Example 28 and p-tolyl-thiourea (purchased from Tokyo Kasei), The reaction was performed in the same manner to obtain the title compound.

MS (APCI, m / z): 427 (M + H) +; HPLC (N): Rt = 7.6 min. (Example 214) 4- [4- (8-benzyloxy-2-methyl-) Ethyl imidazo [1,2-α] pyridin-3-yl) -thiazol-2-ylamino] -benzoate Ethyl 4-thioureido-ethyl benzoate (Example 202 was prepared using Reference Example 49). The reaction was carried out in the same manner as in to give the title compound.

MS (APCI, m / z): 485 (M + H) +; HPLC (N): Rt = 6.8 min. (Example 215) [4- (8-benzyloxy-2-methyl-imidazo [ 1,2-α] pyridin-3-yl) -thiazol-2-yl]-(6-methoxy-pyridin-3-yl) -amine The compound of Reference Example 28 and (6-methoxy-pyridin-3)
The reaction was carried out in the same manner as in Example 202 using -yl) -thiourea (Reference Example 43) to obtain the title compound.

MS (APCI, m / z): 444 (M + H) +; HPLC (N): Rt = 6.4 min. (Example 216) [4- (8-benzyloxy-2-methyl-imidazo [ 1,2-α] pyridin-3-yl) -thiazol-2-yl]-(4-trifluoromethyl-phenyl) -amine The compound of Reference Example 28 and (4-trifluoromethyl-phenyl) -thiourea (reference Example 2)
Reaction was carried out in the same manner as in Example 02 to obtain the title compound.

MS (APCI, m / z): 481 (M + H) +; HPLC (N): Rt = 5.5 min. (Example 217) 4- [4- (8-benzyloxy-2-methyl-) Example using imidazo [1,2-α] pyridin-3-yl) -thiazol-2-ylamino] -benzonitrile The compound of Reference Example 28 and (4-cyano-phenyl) -thiourea (Reference Example 48) The reaction was carried out in the same manner as in 202 to obtain the title compound.

MS (APCI, m / z): 438 (M + H) +; HPLC (N): Rt = 7.5 min. (Example 218) [4- (8-methoxy-2-methyl-imidazo [1 , 2-α] pyridine-3
-Yl) -thiazol-2-yl]-(4-methoxy-phenyl) -amine Using the compound of Reference Example 31 and (4-methoxy-phenyl) -thiourea (Reference Example 3), reacted in the same manner as in Example 202. To give the title compound.

1H-NMR (DMSO-d6) δ: 10.16 (s, 1H), 8.
54 (d, 1H, J = 7.0Hz), 7.54 (d, 2H, J = 8.9Hz), 6.99
(s, 1H), 6.93 (d, 2H, J = 8.9Hz), 6.86 (t, 1H, J = 7.0
Hz), 6.70 (d, 1H, J = 7.6Hz), 3.94 (s, 3H), 3.73 (s,
3H) 2.51 (s, 3H); MS (APCI, m / z): 367 (M + H) +; HPLC (N): Rt = 9.4 min. (Example 219) 1- [4- [4- ( 8-methoxy-2-methyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-ylamino] -phenyl] -ethanone The compound of Reference Example 31 and (4-acetyl-phenyl) -thiourea ( Using Reference Example 47), a reaction was carried out in the same manner as in Example 202 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.87 (brs, 1H),
8.49 (d, 1H, J = 6.8Hz), 7.96 (d, 2H, J = 8.6Hz), 7.76
(d, 2H, J = 8.6Hz), 7.22 (s, 1H), 6.90 (t, 1H, J = 7.3H
z), 6.73 (d, 1H, J = 7.6Hz), 3.95 (s, 3H), 2.52 (s, 3
H) 2.50 (s, 3H); MS (APCI, m / z): 379 (M + H) +; HPLC (N): Rt = 7.4 min. (Example 220) [4- (8-methoxy-2) -Methyl-imidazo [1,2-α] pyridine-3
-Yl) -thiazol-2-yl] -p-tolyl-amine Using the compound of Reference Example 31 and p-tolyl-thiourea (purchased from Tokyo Chemical Industry), a reaction was conducted in the same manner as in Example 202, and the title compound was converted Obtained.

1H-NMR (DMSO-d6) δ: 10.28 (s, 1H), 8.
54 (d, 1H, J = 7.0Hz), 7.51 (d, 2H, J = 8.4Hz), 7.14
(d, 2H, J = 8.4Hz), 7.04 (s, 1H), 6.86 (t, 1H, J = 7.3
Hz), 6.70 (d, 1H, J = 7.3Hz), 3.94 (s, 3H), 2.51 (s,
3H), 2.26 (s, 3H); MS (APCI, m / z): 351 (M + H) +; HPLC (N): Rt = 7.5 min. (Example 221) 4- [4- (8- Methoxy-2-methyl-imidazo [1,2-α] pyridine
-3-yl) -thiazol-2-ylamino] -ethyl benzoate
Ester The reaction was carried out in the same manner as in Example 202 using the compound of Reference Example 31 and ethyl 4-thioureido-benzoate (Reference Example 49) to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.86 (brs, 1H),
8.49 (d, 1H, J = 6.8Hz), 7.93 (d, 2H, J = 8.9Hz), 7.76
(d, 2H, J = 8.9Hz), 7.21 (s, 1H), 6.90 (t, 1H, J = 7.0H
z), 6.72 (d, 1H, J = 7.3Hz), 4.28 (q, 2H, J = 7.3Hz),
3.95 (s, 3H), 2.51 (s, 3H) 1.31 (t, 3H, J = 7.0Hz); MS (APCI, m / z): 409 (M + H) +; HPLC (N): Rt = 7.3 min. (Example 222) [4- (8-Methoxy-2-methyl-imidazo [1,2-α] pyridine-3
-Yl) -thiazol-2-yl]-(6-methoxy-pyridine-3-
Yl) -amine The compound of Reference Example 31 and (6-methoxy-pyridine-3-
Example 2 using yl) -thiourea (Reference Example 43)
Reaction was carried out in the same manner as in Example 02 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.31 (brs, 1H),
8.48-8.46 (m, 2H), 7.98 (dd, 1H, J = 3.0Hz, 8.9Hz),
7.06 (s, 1H), 6.86 (t, 1H, J = 5.9Hz), 6.84 (d, 1H, J
= 8.6Hz), 6.70 (d, 1H, J = 7.8Hz), 3.94 (s, 3H), 3.82
(s, 3H), 2.51 (s, 3H); MS (APCI, m / z): 368 (M + H) +; HPLC (N): Rt = 6.6 min. (Example 223) [4- (8 -Methoxy-2-methyl-imidazo [1,2-α] pyridine-3
-Yl) -thiazol-2-yl]-(4-trifluoromethyl-phenyl) -amine Example using the compound of Reference Example 31 and (4-trifluoromethyl-phenyl) -thiourea (Reference Example 2). 2
Reaction was carried out in the same manner as in Example 02 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 8.47 (d, 1H, J = 7.
0Hz), 7.84 (d, 2H, J = 8.9Hz), 7.68 (d, 2H, J = 8.9H
z), 7.21 (s, 1H), 6.89 (t, 1H, J = 7.3Hz), 6.72 (d,
1H, J = 7.6Hz), 3.98 (s, 3H), 2.51 (s, 3H); MS (APCI, m / z): 405 (M + H) +; HPLC (N): Rt = 6.5 min. Example 224) 4- [4- (8-methoxy-2-methyl-imidazo [1,2-α] pyridine
-3-yl) -thiazol-2-ylamino] -benzonitrile Using the compound of Reference Example 31 and (4-cyano-phenyl) -thiourea (Reference Example 48), the reaction was carried out in the same manner as in Example 202, and the reaction was carried out. The compound was obtained.

1H-NMR (DMSO-d6) δ: 10.97 (brs, 1H),
8.43 (d, 1H, J = 6.8Hz), 7.88-7.71 (m, 4H), 7.25 (s,
1H), 6.88 (t, 1H, J = 7.3Hz), 6.72 (d, 1H, J = 7.6Hz),
3.95 (s, 3H), 2.50 (s, 3H); MS (APCI, m / z): 362 (M + H) +; HPLC (N): Rt = 8.7 min. (Example 225) 1- [4 -[4- (8-Hydroxy-2-methyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-ylamino] -phenyl]-
Ethanone Example 20 was prepared using the compound of Reference Example 33 (1) and (4-acetyl-phenyl) -thiourea (Reference Example 47).
The reaction was carried out in the same manner as in Example 2 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.87 (brs, 1H),
8.39 (d, 1H, J = 6.8Hz), 7.95 (d, 2H, J = 8.6Hz), 7.76
(d, 2H, J = 8.6Hz), 7.21 (s, 1H), 6.83-6.78 (m, 1H),
6.54 (d, 1H, J = 7.6Hz), 2.54 (s, 3H), 2.50 (s, 3H); MS (FAB, m / z): 365 (M + H) +. (Example 226) 3- [2- (4-Methoxy-phenylamino) -thiazol-4-yl] -2-methyl-imidazo [1,2-α] pyridin-8-ol The compound of Reference Example 33 (1) and (4-methoxy- Example 202 using phenyl) -thiourea (Reference Example 3)
The reaction was carried out in the same manner as in to give the title compound.

1H-NMR (DMSO-d6) δ: 10.16 (s, 1H), 8.
45 (d, 1H, J = 6.8Hz), 7.54 (d, 2H, J = 8.9Hz), 6.99
(s, 1H), 6.93 (d, 2H, J = 8.9Hz), 6.77 (t, 1H, J = 7.3
Hz), 6.54 (d, 1H, J = 7.6Hz), 3.73 (s, 3H), 3.46 (br
(s, 1H), 2.52 (s, 3H); MS (FAB, m / z): 352 (M) +. (Example 227) 2-methyl-3- (2-p-tolylamino-thiazol-4-yl) ) -Imidazo [1,2-α] pyridin-8-ol Using the compound of Reference Example 33 (1) and p-tolyl-thiourea (purchased from Tokyo Chemical Industry), a reaction was conducted in the same manner as in Example 202, and The compound was obtained.

1H-NMR (DMSO-d6) δ: 10.27 (s, 1H), 8.
45 (d, 1H, J = 6.8Hz), 7.52 (d, 2H, J = 8.4Hz), 7.40
(d, 2H, J = 8.4Hz), 7.04 (s, 1H), 6.78 (t, 1H, J = 7.3
Hz), 6.55 (d, 1H, J = 7.3Hz), 3.35 (brs, 3H), 2.52
(s, 3H), 2.25 (s, 3H); MS (FAB, m / z): 336 (M) +. (Example 228) 4- [4- (8-Hydroxy-2-methyl-imidazo [1 , 2-α] pyridin-3-yl) -thiazol-2-ylamino] -benzoic acid ethyl ester Example was prepared using the compound of Reference Example 33 (1) and 4-thioureido-ethyl benzoate (Reference Example 49). The reaction was carried out in the same manner as in 202 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.87 (s, 1H), 8.
43 (d, 1H, J = 6.8Hz), 7.93 (d, 2H, J = 8.6Hz), 7.77
(d, 2H, J = 8.6Hz), 7.27 (s, 1H), 6.91 (t, 1H, J = 7.0
Hz), 6.67 (d, 1H, J = 7.6Hz), 4.27 (q, 2H, J = 7.0Hz),
3.17 (brs, 3H), 2.56 (s, 3H), 1.31 (t, 3H, J = 7.0H
MS) (FAB, m / z): 394 (M) +. (Example 229) 3- [2- (6-Methoxy-pyridin-3-ylamino) -thiazole
-4-yl] -2-methyl-imidazo [1,2-α] pyridin-8-ol The compound of Reference Example 33 (1) and (6-methoxy-pyridin-3-yl) -thiourea (Reference Example 43) And the reaction was carried out in the same manner as in Example 202 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.37 (s, 1H), 8.
48-8.46 (m, 2H), 7.96 (dd, 1H, J = 3.0Hz, 8.9Hz), 7.
21 (s, 1H), 7.00 (d, 1H, J = 6.8Hz), 6.84 (d, 2H, J =
(8.9 Hz), 3.82 (s, 3H), 3.32 (s, 3H) 2.52 (s, 3H); MS (FAB, m / z): 353 (M) +. (Example 230) 2-methyl-3- [2- (4-trifluoromethyl-phenylamino) -thiazol-4-yl] -imidazo [1,2-α] pyridine-8-
All The reaction was carried out in the same manner as in Example 202 using the compound of Reference Example 33 (1) and (4-trifluoromethyl-phenyl) -thiourea (Reference Example 2) to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.82 (s, 1H), 8.
37 (d, 1H, J = 6.8Hz), 7.84 (d, 2H, J = 8.6Hz), 7.68
(d, 2H, J = 8.6Hz), 7.20 (s, 1H), 6.80 (t, 1H, J = 7.3
Hz), 6.55 (d, 1H, J = 7.0Hz), 3.33 (brs, 1H), 2.54
(s, 3H); MS (EI, m / z): 390 (M) +. (Example 231) 1- [4- [4- (7-bromo-8-hydroxy-2-methyl-imidazo)
[1,2-α] pyridin-3-yl) -thiazol-2-ylamino]-
Phenyl] -ethanone The compound of Reference Example 33 (2) and (4-acetyl-phenyl)
Using -thiourea (Reference Example 47), the reaction was carried out in the same manner as in Example 202 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.97 (s, 1H), 8.
54 (d, 1H, J = 7.6Hz), 7.97 (d, 2H, J = 8.6Hz), 7.75
(d, 2H, J = 8.6Hz), 7.52 (d, 1H, J = 7.0Hz), 7.49 (s,
1H), 3.80 (brs, 1H), 2.61 (s, 3H), 2.50 (s, 3H); MS
(FAB, m / z) 443 (M + H) + (Example 232) 2,2,2-trifluoro-N- [3- [2- (4-methoxy-phenylamino) -thiazol-4-yl ] -2-Methyl-imidazo [1,2-α]
Pyridin-8-yl] -acetamide N- (3-acetyl-2-methyl-imidazo [1,2-α] pyridine-8-
Yl) -2,2,2-trifluoro-acetamide (Reference Example 23)
29 mg (100 μmol), (4-methoxy-phenyl) -thiourea (Reference Example 3) 18 mg (100 μmol) and iodine 25 mg (100 μmol)
Dissolved in 2 ml of N, N-dimethylformamide, 100 ℃
For 14 hours. Ethyl acetate was added to the reaction solution, and the mixture was washed with a saturated aqueous solution of sodium hydrogen carbonate and then with a saturated saline solution. After the organic layer was dried over anhydrous sodium sulfate, the solvent was concentrated under reduced pressure. The obtained residue was purified by preparative thin-layer chromatography (hexane / ethyl acetate = 1: 1) to give the title compound (3 mg, 7%).

1H-NMR (CDCl3) δ: 8.68 (d, 1H, J = 6.2
Hz), 8.08 (d, 1H, J = 7.6Hz), 7.53 (brs, 1H), 7.26-7.
24 (m, 3H), 6.90 (d, 1H, J = 8.9Hz), 6.80 (t, 1H, J =
7.3Hz), 6.61 (s, 1H), 3.82 (s, 3H), 2.10 (s, 3H); MS (APCI, m / z) 448 (M + H) +; HPLC (N); Rt = 4.0 min Example 233 3- [2- (4-Methoxy-phenylamino) -thiazol-4-yl] -2-methyl-imidazo [1,2-α] pyridin-8-ylamine 2,2,2- Trifluoro-N- [3- [2- (4-methoxy-phenylamino) -thiazol-4-yl] -2-methyl-imidazo [1,2-α]
Pyridin-8-yl] -acetamide (Example 232) 22
mg (49 micromol) in 1 ml of tetrahydrofuran
And 1 ml of a methanol solution, 50 μl of a 1N aqueous solution of sodium hydroxide was added, and the mixture was stirred at room temperature for 14 hours. Again, 50 μl of a 1N aqueous sodium hydroxide solution was added, and the mixture was stirred at 65 ° C. for 3 hours. After allowing the reaction solution to cool, ethyl acetate was added, and the mixture was washed with water and then with a saturated saline solution. After the organic layer was dried over anhydrous sodium sulfate, the solvent was concentrated under reduced pressure. The obtained residue was purified by preparative thin-layer chromatography (ethyl acetate) to obtain the title compound (12 mg, 67%).

1H-NMR (CDCl3) δ: 8.22 (d, 1H, J = 6.8
Hz), 8.04 (brs, 1H), 7.20 (d, 2H, J = 8.9Hz), 6.85
(d, 2H, J = 8.9Hz), 6.58 (d, 1H, J = 6.5Hz), 6.57 (t,
1H, J = 6.5Hz), 6.32 (d, 1H, J = 6.8Hz), 4.45 (s, 2H),
3.81 (s, 3H), 2.58 (s, 3H); MS (APCI, m / z) 352 (M + H) +; HPLC (N); Rt = 8.6 min. (Example 234) 3- [2- (4-Methoxy-phenylamino) -thiazol-4-yl] -imidazo [1,2-α] pyridine-2-carboxylic acid 3- [2- (4-methoxy-phenylamino) -thiazol-4-yl] -Imidazo [1,2-α] pyridine-2-carboxylic acid methyl ester hydrobromide (138 mg, 0.299 mmol) was dissolved in methanol (5 ml), 1N aqueous sodium hydroxide solution (0.6 ml) was added, and the mixture was added at room temperature. Stir for 1 hour at 60 ° C. for 1 hour. After allowing the reaction solution to cool, a hydrogen chloride-methanol solution was added to adjust the pH to 1. The reaction solution was concentrated under reduced pressure, and the obtained residue was treated with 1 ml of methanol and 1 ml of tetrahydrofuran.
Then, 100 mg (243 micromol, 2.43 mmol / g) of tris- (2-aminoethyl) -amine polystyrene HL resin was added, and the mixture was stirred at room temperature for 3 minutes. The reaction solution was filtered, and the filtrate was concentrated under reduced pressure. The obtained crystals were finely ground and washed with hexane-ethyl ether to obtain 121 mg of the title compound.

1H-NMR (DMSO-d6) δ: 10.26 (s, 1H),
8.84 (d, 1H, J = 7.0Hz), 7.72 (d, 1H, J = 8.9Hz), 7.54
-7.47 (m, 5H), 7.14 (t, 1H, J = 7.0Hz), 6.90 (d, 2H,
J = 8.9 Hz), 3.72 (s, 3H); MS (FAB, m / z) 367 (M + H) +. (Example 235) 3- [2- (4-methoxy-phenylamino) -thiazole- 4-yl] -imidazo [1,2-α] pyridine-2-carboxylic acid amide 3- [2- (4-methoxy-phenylamino) -thiazol-4-yl] -imidazo [1,2-α] pyridine 2-Carboxylic acid (Example 234) (25 mg, 68.2 μmol) was dissolved in anhydrous tetrahydrofuran (1 ml), and N, N-carbonyldiimidazole (0.136 mmol) and N, N-
0.5 ml of dimethylformamide was added and stirred for 20 minutes. 0.1 ml of 28% -ammonia water was added and stirred for 3 hours. Ethyl acetate was added to the reaction solution, and the mixture was washed with a saturated aqueous solution of sodium hydrogen carbonate and then with a saturated saline solution. After the organic layer was dried over anhydrous sodium sulfate, the solvent was concentrated under reduced pressure.
The obtained crystals were finely ground and washed with hexane-ethyl ether to obtain 11 mg (44%) of the title compound.

1H-NMR (DMSO-d6) δ: 10.15 (s, 1H),
9.04 (d, 1H, J = 7.3Hz), 7.79 (brs, 1H), 7.66 (d, 2H,
J = 8.6Hz), 7.52 (d, 2H, J = 8.6Hz), 7.44-7.39 (m, 2
H), 7.06 (t, 1H, J = 6.5Hz), 6.93 (d, 2H, J = 8.9Hz),
3.73 (s, 3H); MS (APCI, m / z): 366 (M + H) +; HPLC (N): Rt = 6.2 min. (Example 236) 3- [2- (4-methoxy-phenyl) Amino) -thiazol-4-yl] -imidazo [1,2-α] pyridine-2-carboxylic acid methylamide Using 40% aqueous solution of methylamine, the reaction was carried out in the same manner as in Example 235 to obtain the title compound. .

1H-NMR (CDCl3) δ: 9.11 (d, 1H, J = 6.6H
z), 7.85 (s, 1H), 7.62-7.54 (m, 2H), 7.34 (d, 2H, J
= 8.9Hz), 7.35-7.26 (m, 2H), 6.93 (d, 2H, J = 8.9Hz),
6.85 (t, 1H, J = 6.1Hz), 3.83 (s, 3H), 3.02 (d, 3H,
J (5.1 Hz); MS (APCI, m / z) 380 (M + H) +; HPLC (N): Rt = 5.6 min. (Example 237) 3- [2- (4-methoxy-phenylamino) Example 235 was performed using a 50% aqueous solution of -thiazol-4-yl] -imidazo [1,2-α] pyridine-2-carboxylic acid dimethylamide.
The reaction was carried out in the same manner as in to give the title compound.

1H-NMR (CDCl3) δ: 9.07 (d, 2H, J = 7.3H
z), 7.91 (s, 1H), 7.60 (d, 1H, J = 9.2Hz), 7.51 (br
s, 1H), 7.33-7.22 (m, 3H), 6.92-6.83 (m, 3H), 3.81
(s, 3H), 3.15 (s, 3H), 3.02 (s, 3H); MS (APCI, m / z): 394 (M + H) +; HPLC (N): Rt = 5.3 min. 238) N- (4-Acetyl-phenyl) -N- [4- (2,6-dimethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -acetamide 1- [ 4- [4- (2,6-dimethyl-imidazo [1,2-α] pyridine-3-
The same reaction as in Example 126 was carried out using yl) -thiazol-2-ylamino] -phenyl] -ethanone (Example 58) to give the title compound.

1H-NMR (CDCl3) δ: 8.27 (s, 1H), 8.20
(d, 2H, J = 8.9Hz), 7.56 (d, 2H, J = 8.9Hz), 7.36 (d,
1H, J = 9.2Hz), 7.04 (s, 1H), 6.90 (dd, 1H, J = 1.6Hz,
9.2Hz), 2.68 (s, 3H), 2.58 (s, 3H), 2.15 (s, 3H),
2.01 (s, 3H); MS (APCI, m / z): 405 (M + H) +; HPLC (N): Rt = 7.3 min. (Example 239) N- (4-acetyl-phenyl) -N -[4- (6-Chloro-2-methyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl]-
Acetamide 1- [4- [4- (6-chloro-2-methyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-ylamino] -phenyl] -ethanone (Example 82) The reaction was carried out in the same manner as in Example 126 to obtain the title compound.

1H-NMR (CDCl3) δ: 8.60 (d, 1H, J = 1.6H
z), 8.24 (d, 2H, J = 8.4Hz), 7.54 (d, 2H, J = 8.4Hz),
7.39 (d, 1H, J = 9.5Hz), 7.08 (s, 1H), 7.00 (dd, 1H,
J = 1.9Hz, 9.5Hz), 2.69 (s, 3H), 2.61 (s, 3H), 2.17
(s, 3H); MS (APCI, m / z): 425 (M + H) +, 427 (M + H) +; HPLC (N): Rt = 5.1 min. (Example 240) [4- ( 2-methoxymethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl]-(4-methoxy-phenyl) -amine hydrobromide The compound of Reference Example 34 and (4- The reaction was carried out in the same manner as in Example 157 using methoxy-phenyl) -thiourea (Reference Example 3) to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.34 (s, 1H), 9.
17 (d, 1H, J = 6.8Hz), 7.94-7.92 (m, 2H), 7.54 (d, 2
H, J = 9.2Hz), 7.56-7.53 (m, 1H), 7.32 (s, 1H), 6.94
(d, 2H, J = 9.2Hz), 4.81 (s, 2H), 3.73 (s, 3H), 3.42
(s, 3H). (Example 241) (4-Methoxy-phenyl)-[4- [2- (1-methyl-cyclopropyl) -imidazo [1,2-α] pyridin-3-yl] -thiazole 2-Yyl] -amine Using the compound of Reference Example 51 and (4-methoxy-phenyl) -thiourea (Reference Example 3), the reaction was carried out in the same manner as in Example 188 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.16 (s, 1H), 8.
80 (d, 1H, J = 7.0Hz), 7.56-7.51 (m, 3H), 7.25 (d, 2
H, J = 7.6Hz), 7.08 (s, 1H), 6.95-6.90 (m, 1H), 6.92
(d, 2H, J = 8.9Hz), 3.71 (s, 3H), 1.38 (s, 3H), 0.96
(s, 2H), 0.74 (s, 2H). (Example 242) 1- (4- [4- [2- (1-methyl-cyclopropyl) -imidazo [1,2-
α] pyridin-3-yl] -thiazol-2-ylamino] -phenyl) -ethanone Using the compound of Reference Example 51 and (4-acetyl-phenyl) -thiourea (Reference Example 47), as in Example 188. The reaction was performed to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.85 (s, 1H), 8.
73 (d, 1H, J = 5.9Hz), 7.94 (d, 2H, J = 6.5Hz), 7.75
(d, 2H, J = 6.5Hz), 7.54 (d, 1H, J = 8.9Hz), 7.28-7.25
(m, 1H), 7.28 (s, 1H), 6.96 (s, 1H), 2.50 (s, 3H),
1.39 (s, 3H), 0.97 (s, 2H), 0.74 (s, 2H). (Example 243) [4- [2- (1-methyl-cyclopropyl) -imidazo [1,2-α] pyridine -3-yl] -thiazol-2-yl] -p-tolyl-amine Using the compound of Reference Example 51 and p-tolyl-thiourea (purchased from Tokyo Chemical Industry), a reaction was carried out in the same manner as in Example 188, and the reaction was carried out. The compound was obtained.

1H-NMR (DMSO-d6) δ: 10.27 (s, 1H), 8.
80 (d, 1H, J = 7.3Hz), 7.55-7.51 (m, 1H), 7.53 (d, 2
H, J = 8.4Hz), 7.26 (t, 1H, J = 6.5Hz), 7.15-7.12 (m,
1H), 7.13 (d, 2H, J = 8.4Hz), 6.93 (t, 1H, J = 6.8Hz),
2.25 (s, 3H), 1.38 (s, 3H), 0.98-0.95 (m, 2H), 0.7
6-0.72 (m, 2H). (Example 244) 4- [4- [2- (1-methyl-cyclopropyl) -imidazo [1,2-α]
Pyridin-3-yl] -thiazol-2-ylamino] -ethyl benzoate Using the compound of Reference Example 51 and 4-thioureido-ethyl benzoate (Reference Example 49), the reaction was carried out in the same manner as in Example 188 to give the title. The compound was obtained.

1H-NMR (DMSO-d6) δ: 10.84 (s, 1H), 8.
73 (d, 1H, J = 6.2Hz), 7.93 (d, 2H, J = 8.6Hz), 7.76
(d, 2H, J = 8.6Hz), 7.54 (d, 1H, J = 9.2Hz), 7.28-7.26
(m, 1H), 7.28 (s, 1H), 6.97-6.95 (m, 1H), 4.27 (q,
2H, J = 7.3Hz), 1.39 (s, 3H), 1.30 (t, 3H, J = 7.3Hz),
0.97 (s, 2H), 0.75 (s, 2H). (Example 245) (6-Methoxy-pyridin-3-yl)-[4- [2- (1-methyl-cyclopropyl) -imidazo [1, 2-α] pyridin-3-yl] -thiazol-2-yl] -amine The compound of Reference Example 51 and (6-methoxy-pyridin-3)
Example 1 using -yl) -thiourea (Reference Example 43)
The reaction was carried out in the same manner as in 88 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.27 (s, 1H), 8.
72 (d, 1H, J = 5.9Hz), 8.40 (d, 1H, J = 2.4Hz), 8.02-
7.98 (m, 1H), 7.53 (d, 1H, J = 8.9Hz), 7.26 (t, 1H,
J = 6.8Hz), 7.13 (s, 1H), 6.92 (t, 1H, J = 6.8Hz), 6.8
3 (d, 1H, J = 8.9Hz), 3.81 (s, 3H), 1.37 (s, 3H), 0.
96 (s, 2H), 0.75 (s, 2H). (Example 246) [4- [2- (1-Methyl-cyclopropyl) -imidazo [1,2-α] pyridin-3-yl] -thiazole 2-yl]-(4-trifluoromethyl-phenyl) -amine Example 1 was prepared using the compound of Reference Example 51 and (4-trifluoromethyl-phenyl) -thiourea (Reference Example 2).
The reaction was carried out in the same manner as in 88 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.83 (s, 1H), 8.
69 (d, 1H, J = 7.0Hz), 7.84 (d, 2H, J = 8.4Hz), 7.68
(d, 2H, J = 8.4Hz), 7.54 (t, 1H, J = 8.9Hz), 7.30-7.25
(m, 1H), 7.28 (s, 1H), 6.96 (t, 1H, J = 7.0Hz), 1.38
(s, 3H), 0.97 (s, 2H), 0.76-0.73 (m, 2H). (Example 247) 4- [4- [2- (1-methyl-cyclopropyl) -imidazo [1,2- α]
Pyridin-3-yl] -thiazol-2-ylamino] -benzonitrile Using the compound of Reference Example 51 and (4-cyano-phenyl) -thiourea (Reference Example 48), a reaction was carried out in the same manner as in Example 188. The title compound was obtained.

1H-NMR (DMSO-d6) δ: 10.95 (s, 1H), 8.
65 (d, 1H, J = 6.8Hz), 7.83-7.75 (m, 4H), 7.55 (d, 1
H, J = 8.9Hz), 7.32 (s, 1H), 7.28 (t, 1H, J = 8.9Hz),
6.95 (t, 1H, J = 7.8Hz), 1.38 (s, 3H), 0.99-0.95 (m, 2
H), 0.76-0.72 (m, 2H). (Example 248) [4- (Isopropylimidazo [1,2-α] pyridin-3-yl)-
Thiazol-2-yl]-(4-methoxy-phenyl) -amine Using the compound of Reference Example 53 and (4-methoxy-phenyl) -thiourea (Reference Example 3), a reaction was carried out in the same manner as in Example 188. The title compound was obtained.

1H-NMR (DMSO-d6) δ: 10.17 (s, 1H), 8.
73 (d, 1H, J = 7.0Hz), 7.60-7.54 (m, 3H), 7.27 (t, 1
H, J = 6.8Hz), 6.98-6.89 (m, 4H), 3.72 (s, 3H), 3.39
-3.29 (m, 1H), 1.32 (s, 3H), 1.30 (s, 3H). (Example 249) 1- [4- [4- (Isopropylimidazo [1,2-α] pyridin-3-yl) ) -Thiazol-2-ylamino] -phenyl] -ethanone Using the compound of Reference Example 53 and (4-acetyl-phenyl) -thiourea (Reference Example 47), a reaction was carried out in the same manner as in Example 188 to give the title compound. Obtained.

1H-NMR (DMSO-d6) δ: 10.86 (s, 1H), 8.
70 (d, 1H, J = 6.8Hz), 7.94 (d, 2H, J = 8.6Hz), 7.76
(d, 2H, J = 8.6Hz), 7.60 (d, 1H, J = 8.9Hz), 7.29 (t,
1H, J = 7.8Hz), 7.20 (s, 1H), 6.97 (t, 1H, J = 6.8Hz),
3.43-3.32 (m, 1H), 2.50 (s, 3H), 1.34 (s, 3H), 1.
32 (s, 3H). (Example 250) [4- (Isopropylimidazo [1,2-α] pyridin-3-yl)-
Thiazol-2-yl] -p-tolyl-amine Using the compound of Reference Example 53 and (p-tolyl-thiourea (purchased from Tokyo Kasei), the reaction was carried out in the same manner as in Example 188 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.34 (s, 1H), 8.
82 (d, 1H, J = 7.0Hz), 7.73-7.71 (m, 1H,), 7.53 (d,
2H, J = 6.8Hz), 7.17-7.03 (m, 5H), 3.47-3.35 (m, 1
H), 2.25 (s, 3H), 1.36 (s, 3H), 1.33 (s, 3H). (Example 251) [4- (Isopropylimidazo [1,2-α] pyridin-3-yl)-
Thiazol-2-yl]-(6-methoxy-pyridin-3-yl) -amine The compound of Reference Example 53 and (6-methoxy-pyridin-3)
The reaction was carried out in the same manner as in Example 188 using -yl) -thiourea (Reference Example 43) to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.30 (s, 1H), 8.
68 (d, 1H, J = 7.3Hz), 8.45 (d, 1H, J = 2.2Hz), 7.99
(dd, 1H, J = 2.2Hz, 10.5Hz), 7.60 (d, 1H, J = 9.5Hz),
7.31-7.29 (m, 1H), 7.05 (s, 1H), 6.97-6.95 (m, 1
H), 6.83 (d, 1H, J = 9.2Hz), 3.81 (s, 3H), 3.42-3.26
(m, 1H), 1.32 (s, 3H), 1.29 (s, 3H). (Example 252) [4- (Isopropylimidazo [1,2-α] pyridin-3-yl)-
Thiazol-2-yl]-(4-trifluoromethyl-phenyl)
-Amine Example 188 using the compound of Reference Example 53 and (4-trifluoromethyl-phenyl) -thiourea (Reference Example 2)
The reaction was carried out in the same manner as in to give the title compound.

1H-NMR (CDCl3) δ: 9.13 (brs, 1H), 8.6
3 (d, 1H, J = 6.8Hz), 7.65 (d, 1H, J = 8.9Hz), 7.58-7.3
6 (m, 4H), 7.20 (t, 1H, J = 7.8Hz), 6.80 (t, 1H, J =
7.0Hz), 6.73 (d, 1H, J = 3.8Hz), 3.47-3.37 (m, 1H),
Example 253 [4- (2-cyclobutyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl]-(1.45 (s, 3H), 1.43 (s, 3H). 6-Methoxy-pyridin-3-yl) -amine 1- (2-cyclobutyl-imidazo [1,1] obtained by using cyclobutanecarboxylic acid instead of 1-methyl-cyclopropanecarboxylic acid used in Reference Example 50. 2-α] pyridine-3-
2-bromo-1- (2-cyclobutyl-imidazo [1,2-α] obtained by brominating yl) -ethanone in the same manner as in Reference Example 28.
Using (pyridin-3-yl) -ethanone and (6-methoxy-pyridin-3-yl) -thiourea (Reference Example 43),
The reaction was carried out in the same manner as in Example 188 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.31 (s, 1H), 8.
76 (d, 1H, J = 6.2Hz), 8.46 (d, 1H, J = 2.4Hz), 7.99
(dd, 1H, J = 2.4Hz, 8.1Hz), 7.61 (d, 1H, J = 8.6Hz),
7.28 (t, 1H, J = 7.8Hz), 6.95 (s, 1H), 6.83 (d, 1H,
J = 8.6Hz), 3.90 (t, 1H, J = 8.1Hz), 3.82 (s, 3H), 2.5
0-2.41 (m, 2H), 2.30-2.22 (m, 2H), 2.05-1.86 (m, 2
H); MS (APCI, m / z) 409 (M + H) +, 378 (M + H) +; HPLC (N); Rt = 5.4 min. (Example 254) p-tolyl- [4- ( 2-trifluoromethyl-imidazo [1,2-α]
Pyridin-3-yl) -thiazol-2-yl] -amine dihydrochloride p-tolyl- [4- (2-trifluoromethyl-imidazo [1,2-α]
Using pyridine-3-yl) -thiazol-2-yl] -amine (Example 190), the reaction was carried out as in Example 269,
The title compound was obtained.

1H-NMR (DMSO-d6) δ: 10.46 (s, 1H), 8.
66 (d, 1H, J = 7.0Hz), 7.79 (d, 1H, J = 9.2Hz), 7.55-
7.49 (m, 3H), 7.25 (s, 1H), 7.18-7.10 (m, 3H), 6.3
1 (brs, 2H), 2.24 (s, 3H); MS (APCI, m / z) 375 (M + H) +; HPLC (N): Rt = 3.7 min. (Example 255) (4-methoxy- Benzyl)-[4- (2-trifluoromethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl]
-Amine Compound of Reference Example 20 and (4-methoxy-benzyl) -thiourea (Pharmaceutical Magazine, 72, 1952, 1009-10)
Using 12), a reaction was carried out in the same manner as in Example 181, to obtain the title compound.

1H-NMR (CDCl3) δ: 8.59 (dd, 1H, J = 1.1
Hz, 7.3Hz), 7.67 (dd, 1H, J = 1.1Hz, 8.9Hz), 7.31
(d, 2H, J = 8.1Hz), 7.32-7.29 (m, 1H), 6.93-6.81 (m,
4H), 5.91 (brs, 1H), 4.45 (s, 2H), 3.82 (s, 3H). (Example 256) [4- (6-Chloro-2-trifluoromethyl-imidazo [1,2-α ]
Pyridin-3-yl) -thiazol-2-yl]-(6-methoxy-pyridin-3-yl) -amine The compound of Reference Example 70 and (6-methoxy-pyridin-3)
Using -yl) -thiourea (Reference Example 43), the reaction was carried out in the same manner as in Example 1 to obtain the title compound.

Mp 200-204 ° C .; 1H-NMR (DMSO-d6) δ: 10.41 (brs, 1H), 8.90 (d, 1H,
J = 2.7Hz), 8.42 (d, 1H, J = 2.7Hz), 7.99 (dd, 1H, J =
2.7Hz, 8.9Hz), 7.85 (d, 1H, J = 9.7Hz), 7.58 (dd, 1H,
J = 2.2Hz, 9.7Hz), 7.31 (s, 1H), 6.82 (d, 1H, J = 8.9
Hz), 3.82 (s, 3H); MS (APCI, m / z) 426 (M + H) +; HPLC (R): Rt = 5.3 min. (Example 257) [4- (6-chloro-2) -Trifluoromethyl-imidazo [1,2-α]
Example 1 was prepared using the compound of Reference Example 70 and (4-methoxy-phenyl) -thiourea (Reference Example 3), using pyridin-3-yl) -thiazol-2-yl]-(4-methoxy-phenyl) -amine. The reaction was carried out in the same manner as in to give the title compound.

Mp 176-179 ° C .; 1H-NMR (DMSO-d6) δ 10.28 (s, 1H), 8.97 (dd, 1H, J
= 0.8Hz, 1.9Hz), 7.85 (dd, 1H, J = 0.8Hz, 9.7Hz), 7.58
(dd, 1H, J = 2.2Hz, 9.7Hz), 7.53 (d, 2H, J = 9.2Hz),
7.24 (s, 1H), 6.92 (d, 2H, J = 8.9Hz), 3.72 (s, 3H); MS (APCI, m / z) 425 (M + H) +, 427 (M + H) +, HPLC (R); Rt = 5.8 min. (Example 258) 1- [4- [4- (6-Chloro-2-trifluoromethyl-imidazo [1,
2-α] pyridin-3-yl) -thiazol-2-ylamino] -phenyl] -ethanone Using the compound of Reference Example 70 and (4-acetyl-phenyl) -thiourea (Reference Example 47), The reaction was performed in the same manner to obtain the title compound.

Mp 290-295 ° C .; 1H-NMR (DMSO-d6) δ: 11.07 (s, 1H), 8.92 (d, 1H, J
= 1.6Hz), 7.94 (d, 2H, J = 8.6Hz), 7.87 (d, 1H, J = 9.7
Hz), 7.76 (d, 2H, J = 8.9Hz), 7.61 (dd, 1H, J = 1.9Hz,
9.7Hz), 7.48 (s, 1H), 2.50 (s, 3H); MS (APCI, m / z) 437 (M + H) +, 439 (M + H) +; HPLC (R): Rt = 5.3 min. (Example 259) [4- (6-chloro-2-trifluoromethyl-imidazo [1,2-α]]
Using the compound of Reference Example 70 and p-tolyl-thiourea (purchased from Tokyo Kasei), the reaction was carried out in the same manner as in Example 1, using the compound of Reference Example 70 and The title compound was obtained.

Mp 212-217 ° C; 1H-NMR (DMSO-d6) δ 10.40 (s, 1H), 8.98 (dd, 1H, J
= 1.1Hz, 2.2Hz), 7.85 (dd, 1H, J = 1.1Hz, 10.0Hz), 7.5
9 (dd, 1H, J = 2.2Hz, 9.5Hz), 7.51 (d, 2H, J = 8.4Hz),
7.29 (s, 1H), 7.13 (d, 1H, J = 8.6Hz), 2.26 (s, 3H); MS (APCI, m / z): 409 (M + H) +, 411 (M + H) + HPLC (R): Rt = 6.5 min. (Example 260) [4- (6-Chloro-2-trifluoromethyl-imidazo [1,2-α]]
Pyridin-3-yl) -thiazol-2-yl]-(4-trifluoromethyl-phenyl) -amine The compound of Reference Example 70 and (4-trifluoromethyl-phenyl) -thiourea (Reference Example 2) were used. Example 1
The reaction was carried out in the same manner as in to give the title compound.

Mp 227-230 ° C .; 1H-NMR (DMSO-d6) δ: 10.93 (s, 1H), 8.89 (dd, 1H,
J = 0.8Hz, 2.2Hz), 7.87 (dd, 1H, J = 0.8Hz, 9.7Hz), 7.
83 (d, 2H, J = 8.1Hz), 7.66 (d, 2H, J = 8.9Hz), 7.60
(dd, 1H, J = 2.2Hz, 9.7Hz), 7.47 (s, 1H); MS (APCI, m / z) 463 (M + H) +, 465 (M + H) +; HPLC (R): Rt = 6.7 min. (Example 261) (4-methoxy-phenyl)-[4- (6-methyl-2-trifluoromethyl-imidazo [1,2-α] pyridin-3-yl) -thiazole
2-yl] -amine Using the compound of Reference Example 73 and (4-methoxy-phenyl) -thiourea (Reference Example 3), the reaction was carried out in the same manner as in Example 1 to obtain the title compound.

Mp 163-166 ° C .; 1H-NMR (DMSO-d6) δ: 10.25 (s, 1H), 8.51 (d, 1H, J
= 1.1Hz), 7.69 (d, 1H, J = 9.2Hz), 7.54 (d, 2H, J = 8.9
Hz), 7.38 (dd, 1H, J = 1.6Hz, 9.2Hz), 7.19 (s, 1H),
6.91 (d, 2H, J = 8.9Hz), 3.72 (s, 3H), 2.33 (s, 3H); MS (APCI, m / z): 405 (M + H) +; HPLC (R): Rt = 5.3 min. (Example 262) 1- [4- [4- (6-methyl-2-trifluoromethyl-imidazo [1,
2-α] pyridin-3-yl) -thiazol-2-ylamino] -phenyl] -ethanone Using the compound of Reference Example 73 and (4-acetyl-phenyl) -thiourea (Reference Example 47), The reaction was performed in the same manner to obtain the title compound.

Mp 224-227 ° C .; 1H-NMR (DMSO-d6) δ: 10.93 (s, 1H), 8.49 (s, 1H),
7.93 (d, 2H, J = 8.6Hz), 7.75 (d, 2H, J = 8.9Hz), 7.72
(d, 1H, J = 9.7Hz), 7.42 (s, 1H), 7.40 (dd, 1H, J = 1.
6Hz, 9.5Hz), 2.50 (s, 3H), 2.34 (s, 3H); MS (APCI, m / z) 417 (M + H) +; HPLC (R): Rt = 4.8 min. (Example 263) ) [4- (6-methyl-2-trifluoromethyl-imidazo [1,2-α]
Using the compound of Reference Example 73 and p-tolyl-thiourea (purchased from Tokyo Kasei), a reaction was carried out in the same manner as in Example 1, The title compound was obtained.

Mp 212-215 ° C; 1H-NMR (DMSO-d6) δ: 10.36 (s, 1H), 8.53 (s, 1H),
7.69 (d, 2H, J = 9.2Hz), 7.52 (d, 2H, J = 8.4Hz), 7.39
(dd, 1H, J = 1.6Hz, 9.2Hz), 7.23 (s, 1H), 7.13 (d,
1H, J = 8.4Hz), 2.33 (s, 3H), 2.25 (s, 3H); MS (APCI, m / z): 389 (M + H) +; HPLC (R): Rt = 5.9 min. Example 264) [4- (6-Methyl-2-trifluoromethyl-imidazo [1,2-α]
Pyridin-3-yl) -thiazol-2-yl]-(4-trifluoromethyl-phenyl) -amine Using the compound of Reference Example 73 and (4-trifluoromethyl-phenyl) -thiourea (Reference Example 2). Example 1
The reaction was carried out in the same manner as in to give the title compound.

Mp 212-215 ° C .; 1H-NMR (DMSO-d6) δ: 10.90 (brs, 1H), 8.45 (s, 1
H), 7.84 (d, 2H, J = 8.9Hz), 7.70 (d, 1H, J = 9.5Hz),
7.66 (d, 2H, J = 8.9Hz), 7.41 (s, 1H), 7.39 (d, 1H,
(J = 8.6 Hz), 2.33 (s, 3H); MS (APCI, m / z): 443 (M + H) +; HPLC (R): Rt = 6.1 min. (Example 265) (6-methoxy- Pyridin-3-yl)-[4- (6-methyl-2-trifluoromethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -amine The compound of Reference Example 73 and (6-methoxy-pyridine-3
Using -yl) -thiourea (Reference Example 43), the reaction was carried out in the same manner as in Example 1 to obtain the title compound.

Mp 225-227 ° C .; 1H-NMR (DMSO-d6) δ: 10.38 (s, 1H), 8.48 (s, 1H),
8.45 (d, 1H, J = 2.7Hz), 7.99 (dd, 1H, J = 2.7Hz, 8.9H
z), 7.69 (d, 1H, J = 9.2Hz), 7.38 (dd, 1H, J = 1.6Hz,
9.5Hz), 7.25 (s, 1H), 6.82 (d, 1H, J = 8.9Hz), 3.81
(s, 3H), 2.33 (s, 3H); MS (APCI, m / z): 406 (M + H) +; HPLC (R): Rt = 4.9 min. (Example 266) N- (6- Methoxy-pyridin-3-yl) -N- [4- (6-methyl-2-trifluoromethyl-imidazo [1,2-α] pyridin-3-yl)-
Thiazol-2-yl] -acetamide Using the compound of Example 265, the reaction was carried out in the same manner as in Example 280 to obtain the title compound.

Mp 209-211 ° C .; 1H-NMR (DMSO-d6) δ: 8.44 (d, 1H, J = 2.7 Hz), 8.24
(brs, 1H), 8.03 (dd, 1H, J = 2.7Hz, 8.9Hz), 7.62 (s,
1H), 7.60 (d, 1H, J = 9.2Hz), 7.30 (dd, 1H, J = 1.9Hz,
9.2Hz), 7.00 (d, 1H, J = 8.9Hz), 3.89 (s, 3H), 2.20
(s, 3H), 2.09 (s, 3H); MS (APCI, m / z): 448 (M + H) +; HPLC (R): Rt = 5.0 min. (Example 267) [4- (2 , 6-Dimethyl-imidazo [1,2-α] pyridin-3-yl)-
Thiazol-2-yl]-(4-methoxy-phenyl) -amine
Dihydrochloride [4- (2,6-dimethyl-imidazo [1,2-α] pyridin-3-yl)-
Using thiazol-2-yl]-(4-methoxy-phenyl) -amine (Example 57), the reaction was carried out in the same manner as in Example 269 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.51 (s, 1H), 9.
10 (s, 1H), 7.92 (d, 1H, J = 9.2Hz), 7.85 (d, 1H, J =
9.2Hz), 7.56 (d, 2H, J = 8.4Hz), 7.38 (s, 1H), 6.94
(d, 2H, J = 8.9Hz), 3.74 (s, 3H), 2.65 (s, 3H), 2.45
(s, 3H); MS (APCI, m / z): 351 (M + H) +; HPLC (R): Rt = 9.5 min. (Example 268) [4- (2,6-dimethyl-imidazo [ 1,2-α] pyridin-3-yl)-
Thiazol-2-yl] -p-tolyl-amine [4- (2,6-dimethyl-imidazo [1,2-α] pyridin-3-yl)-
Using thiazol-2-yl] -p-tolyl-amine (Example 59), the reaction was carried out in the same manner as in Example 269 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.62 (s, 1H), 9.
09 (s, 1H), 7.91 (d, 1H, J = 8.9Hz), 7.83 (d, 1H, J =
9.2Hz), 7.52 (d, 2H, J = 8.4Hz), 7.41 (s, 1H), 7.13
(d, 2H, J = 8.1Hz), 2.63 (s, 3H), 2.43 (s, 3H), 2.25
(s, 3H); MS (APCI, m / z) 335 (M + H) +; HPLC (R): Rt = 8.0 min. (Example 269) [4- (2,6-dimethyl-imidazo [1 , 2-α] pyridin-3-yl)-
Thiazol-2-yl]-(6-methoxy-pyridin-3-yl) -amine dihydrochloride [4- (2,6-dimethyl-imidazo [1,2-α] pyridin-3-yl)-
Thiazol-2-yl]-(6-methoxy-pyridin-3-yl) -amine (Example 61) was dissolved in a hydrogen chloride-methanol solution, and the mixture was concentrated under reduced pressure. Washing with ethyl gave the title compound.

1H-NMR (DMSO-d6) δ: 10.80 (s, 1H), 9.
04 (s, 1H), 8.52 (d, 1H, J = 2.7Hz), 8.03 (dd, 1H, J
= 2.7Hz, 8.9Hz), 7.91 (d, 1H, J = 8.9Hz), 7.84 (d, 1
H, J = 9.2Hz), 7.44 (s, 1H), 6.87 (d, 1H, J = 8.9Hz),
3.83 (s, 3H), 2.64 (s, 3H), 2.44 (s, 3H); MS (APCI, m / z): 352 (M + H) +; HPLC (R): Rt = 6.5 min. Example 270) [4- (2,6-dimethyl-imidazo [1,2-α] pyridin-3-yl)-
Thiazol-2-yl]-(4-trifluoromethyl-phenyl)
-Amine hydrochloride [4- (2,6-dimethyl-imidazo [1,2-α] pyridin-3-yl)-
Thiazol-2-yl]-(4-trifluoromethyl-phenyl)
The reaction was carried out in the same manner as in Example 269 using -amine (Example 62) to obtain the title compound.

1H-NMR (DMSO-d6) δ: 11.19 (s, 1H), 8.
99 (s, 1H), 7.94-7.85 (m, 4H), 7.69 (d, 2H, J = 8.4H
z), 7.59 (s, 1H), 2.65 (s, 3H), 2.45 (s, 3H); MS (APCI, m / z): 389 (M + H) +; HPLC (N): Rt = 6.0 min Example 271 [4- (6-Chloro-2-methyl-imidazo [1,2-α] pyridine-3-
Yl) -thiazol-2-yl] -p-tolyl-amine dihydrochloride [4- (6-chloro-2-methyl-imidazo [1,2-α] pyridine-3-
Yl) -thiazol-2-yl] -p-tolyl-amine (Example 8
Using 6), a reaction was carried out in the same manner as in Example 269 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.62 (s, 1H), 9.
55 (t, 1H, J = 1.4Hz), 8.03 (d, 2H, J = 1.6Hz), 7.52
(d, 2H, J = 8.6Hz), 7.45 (s, 1H), 7.17 (d, 2H, J = 8.4
Hz), 4.74 (brs, 2H), 2.68 (s, 3H), 2.28 (s, 3H); MS (APCI, m / z): 355 (M + H) +, 357 (M + H) +; HPLC (R): Rt = 3.8 min. (Example 272) [4- (6-Chloro-2-methyl-imidazo [1,2-α] pyridine-3-)
Yl) -thiazol-2-yl]-(6-methoxy-pyridin-3-yl) -amine dihydrochloride [4- (6-chloro-2-methyl-imidazo [1,2-α] pyridine-3-
Using yl) -thiazol-2-yl]-(6-methoxy-pyridin-3-yl) -amine (Example 84), the reaction was carried out in the same manner as in Example 269 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.67 (s, 1H), 9.
42 (d, 1H, J = 1.4Hz), 8.46 (d, 1H, J = 1.9Hz), 8.02-
7.99 (m, 3H), 7.46 (d, 1H, J = 1.6Hz), 6.85 (d, 1H,
J = 8.9Hz), 5.08 (brs, 2H), 3.83 (s, 3H), 2.67 (s, 3
H); MS (APCI, m / z): 372 (M + H) +, 374 (M + H) +; HPLC (R): Rt = 3.7 min. (Example 273) (4-methoxy-phenyl) -[4- (2-Methyl-imidazo [1,2-
α] pyridin-3-yl) -thiazol-2-yl] -amine 2
Hydrochloride (4-methoxy-phenyl)-[4- (2-methyl-imidazo [1,2-
Using α] pyridin-3-yl) -thiazol-2-yl] -amine (Example 3), the reaction was carried out in the same manner as in Example 269,
The title compound was obtained.

1H-NMR (DMSO-d6) δ: 10.54 (s, 1H), 9.
19 (d, 1H, J = 7.0Hz), 7.98 (d, 2H, J = 5.7Hz), 7.59-
7.55 (m, 3H), 7.39 (s, 1H), 6.93 (d, 2H, J = 8.9Hz),
4.25 (brs, 2H), 3.73 (s, 3H), 2.66 (s, 3H); MS (APCI, m / z) 337 (M + H) +; HPLC (R): Rt = 6.4 min. 274) [4- (6-Chloro-2-methyl-imidazo [1,2-α] pyridine-3-
Yl) -thiazol-2-yl]-(4-trifluoromethyl-phenyl) -amine hydrochloride [4- (6-chloro-2-methyl-imidazo [1,2-α] pyridine-3-
Example 269 using yl) -thiazol-2-yl]-(4-trifluoromethyl-phenyl) -amine (Example 85).
The reaction was carried out in the same manner as in to give the title compound.

1H-NMR (DMSO-d6) δ: 11.12 (s, 1H), 9.
35 (dd, 1H, J = 1.1Hz, 1.9Hz), 7.95 (d, 1H, J = 9.5H
z), 7.92 (d, 1H, J = 9.7Hz), 7.85 (d, 2H, J = 8.6Hz),
7.68 (d, 2H, J = 8.6Hz), 7.54 (s, 1H), 3.71 (brs, 1
H), 2.65 (s, 3H); MS (APCI, m / z): 409 (M + H) +, 411 (M + H) +; HPLC (R): Rt = 5.9 min. (Example 275) (N- [4- (6-chloro-2-methyl-imidazo [1,2-α] pyridine-
3-yl) -thiazol-2-yl] -N- (4-methoxy-phenyl)
-Acetamide Using the compound of Example 78, reaction was carried out as in Example 126 to obtain the title compound.

1H-NMR (CDCl3) δ: 8.76 (dd, 1H, J = 0.8
Hz, 2.2Hz), 7.40 (d, 1H, J = 9.5Hz), 7.31 (d, 2H, J =
8.6Hz), 7.12 (d, 2H, J = 8.6Hz), 7.06 (s, 1H), 7.03
(dd, 1H, J = 2.2Hz, 9.5Hz), 3.90 (s, 3H), 2.62 (s, 3
H), 2.17 (s, 3H). (Example 276) (4-Methoxy-benzyl)-[4- (2-methyl-imidazo [1,2-
α] pyridin-3-yl) -thiazol-2-yl] -amine 2-bromo-1- (2-methyl-imidazo [1,2-α] pyridin-3-yl) -ethanone (Reference Example 56) 25 0.3 mg (0.10 mmol) and (4-methoxy-benzyl) -thiourea (Pharmaceutical Magazine, 72, 1952, 1009-1012).
7 mg (0.10 mmol) was dissolved in 1.5 ml of ethanol and heated under reflux for 16 hours. 100 mg (67 micromol, 0.67 mmol / g) of aminomethylated polystyrene resin was added to the reaction solution, and the mixture was stirred at room temperature for 3 minutes. The reaction solution was filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was eluted with water (0.1% trifluoroacetic acid) -methanol using Wakogel C-18 to give 21 m of the title compound.
g (60%).

1H-NMR (CDCl3) δ: 8.93 (d, 1H, J = 7.0H
z), 8.17 (d, 1H, J = 9.2Hz), 7.62 (t, 1H, J = 7.8Hz),
7.33 (d, 2H, J = 8.6Hz), 7.12 (t, 1H, J = 7.0Hz), 6.91
(d, 2H, J = 8.6Hz), 6.67 (s, 1H), 6.14 (brs, 1H), 4.4
9 (s, 2H), 3.82 (s, 3H), 2.68 (s, 3H). (Example 277) [4- (6-Chloro-2-methyl-imidazo [1,2-α] pyridine-3-
Yl) -thiazol-2-yl]-(4-methoxy-benzyl) -amine The compound of Reference Example 12 and (4-methoxy-benzyl) -thiourea (Pharmaceutical Magazine, 72, 1952, 1009-101)
The reaction was carried out in the same manner as in Example 181 using 2) to obtain the title compound.

1H-NMR (CDCl3) δ: 9.12 (d, 1H, J = 1.4H
z), 7.79 (d, 1H, J = 9.5Hz), 7.34 (d, 2H, J = 8.6Hz),
7.31-7.24 (m, 1H), 6.92 (d, 2H, J = 8.6Hz), 6.61 (s,
1H), 5.79 (brs, 1H), 4.49 (d, 2H, J = 4.3Hz), 3.82
(s, 3H), 2.63 (s, 3H). (Example 278) [4- (2,6-dimethyl-imidazo [1,2-α] pyridin-3-yl)
-Thiazol-2-yl]-(4-methoxy-benzyl) -amine The compound of Reference Example 5 and (4-methoxy-benzyl) -thiourea (Pharmaceutical Magazine, 72, 1952, 1009-101)
The reaction was carried out in the same manner as in Example 181 using 2) to obtain the title compound.

1H-NMR (CDCl3) δ: 8.74 (s, 1H), 8.10
(d, 1H, J = 9.2Hz), 7.47 (dd, 1H, J = 1.9Hz, 9.5Hz), 7.
33 (d, 2H, J = 8.6Hz), 6.92 (d, 2H, J = 8.6Hz), 6.68
(s, 1H), 6.00 (brs, 1H), 4.50 (s, 2H), 3.82 (s, 3
H), 2.67 (s, 3H), 2.38 (s, 3H). (Example 279) N- [4- (2,6-dimethyl-imidazo [1,2-α] pyridin-3-yl) -thiazole -2-yl] -N- (4-methoxy-phenyl) -acetamido [4- (2,6-dimethyl-imidazo [1,2-α] pyridin-3-yl)-
Thiazol-2-yl]-(4-methoxy-phenyl) -amine (Example 57) (500 mg, 1.43 mmol) was dissolved in pyridine (10 ml), and acetic anhydride (5 ml) was added.
For 5 hours. The solvent was concentrated under reduced pressure, and the obtained residue was dissolved in ethyl acetate and washed with a saturated aqueous solution of sodium bicarbonate and subsequently with a saturated saline solution. After the organic layer was dried over anhydrous sodium sulfate, the solvent was concentrated under reduced pressure, and the obtained crystals were finely pulverized and washed with hexane-ethyl acetate to obtain 430 mg (77%) of the title compound.

Mp 201-204 ° C .; 1H-NMR (DMSO-d6) δ: 8.42 (s, 1H), 7.53 (d, 2H, J =
8.9Hz), 7.37 (s, 1H), 7.36 (d, 1H, J = 8.9Hz), 7.15
(d, 1H, J = 9.2Hz), 7.03 (d, 1H, J = 9.2Hz), 3.84 (s,
3H), 2.47 (s, 3H), 2.07 (s, 3H); MS (APCI, m / z): 393 (M + H) +; HPLC (R): Rt = 3.2 min. (Example 280) N -[4- (2,6-dimethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -N- (6-methoxy-pyridin-3-yl) -acetamide [4 -(2,6-Dimethyl-imidazo [1,2-α] pyridin-3-yl)-
Thiazol-2-yl]-(6-methoxy-pyridin-3-yl) -amine hydrobromide (Example 307) 2.00 g (4.6)
3 mmol) was dissolved in 40 ml of pyridine and 5 ml of triethylamine, and 10 ml of acetic anhydride was added.
For 4 hours. 1 ml of acetic anhydride was further added,
Stirred at C for 2 hours. The residue obtained by concentrating the solvent under reduced pressure was dissolved in ethyl acetate, and washed with a saturated aqueous solution of sodium bicarbonate and subsequently with a saturated saline solution. The organic layer was dried over anhydrous sodium sulfate, the solvent was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate). The resulting crystals were finely ground, washed with hexane-ethyl acetate, and dried. 1.79 g (98%) of the compound were obtained.

Mp 200-203 ° C .; 1H-NMR (DMSO-d6) δ: 8.45 (d, 1H, J = 2.7 Hz), 8.39
(d, 1H, J = 0.8Hz), 8.03 (dd, 1H, J = 2.7Hz, 8.9Hz),
7.42 (s, 1H), 7.37 (d, 1H, J = 9.2Hz), 7.07 (d, 1H,
J = 8.6Hz), 7.04 (d, 1H, J = 7.6Hz), 3.94 (s, 3H), 2.4
6 (s, 3H), 2.10 (s, 6H); MS (APCI, m / z): 394 (M + H) +; HPLC (R): Rt = 3.0 min. (Example 281) N- [4 -(6-Chloro-2-methyl-imidazo [1,2-α] pyridine-3
-Yl) -thiazol-2-yl] -N- (6-methoxy-pyridine-3
-Yl) -acetamide [4- (6-chloro-2-methyl-imidazo [1,2-α] pyridine-3-
(Ill) -thiazol-2-yl]-(6-methoxy-pyridin-3-yl) -amine (Example 84) (500 mg, 1.34 mmol) was dissolved in pyridine (10 ml), and acetic anhydride (5 ml) was added. Stir for 5 hours. The solvent was concentrated under reduced pressure, and the obtained residue was dissolved in ethyl acetate and washed with a saturated aqueous solution of sodium bicarbonate and subsequently with a saturated saline solution. After the organic layer was dried over anhydrous sodium sulfate, the solvent was concentrated under reduced pressure, and the obtained crystals were finely pulverized and washed with hexane-ethyl acetate to obtain 495 mg (89%) of the title compound.

Mp 217-221 ° C .; 1H-NMR (DMSO-d6) δ: 8.72 (d, 1H, J = 2.2 Hz), 8.42
(d, 1H, J = 2.7Hz), 8.02 (dd, 1H, J = 2.7Hz, 8.9Hz),
7.52 (d, 1H, J = 9.5Hz), 7.51 (s, 1H), 7.23 (dd, 1H,
J = 2.2Hz, 9.5Hz), 7.07 (d, 1H, J = 8.6Hz), 3.94 (s,
3H), 2.50 (s, 3H), 2.11 (s, 3H); MS (APCI, m / z): 414 (M + H) +, 416 (M + H) +; HPLC (R): Rt = 3.4 min. (Example 282) 3- [2- (6-Methoxy-pyridin-3-ylamino) -thiazole
-4-yl] -2-methyl-imidazo [1,2-α] pyridine-6-carboxylic acid amide The compound of Reference Example 75 and (6-methoxy-pyridine-3)
Using -yl) -thiourea (Reference Example 43), the reaction was carried out in the same manner as in Example 1 to obtain the title compound.

Mp 232-236 ° C. (dec.); 1H-NMR (DMSO-d6) δ 10.36 (s, 1H), 9.49 (s, 1H),
8.59-8.57 (m, 1H), 8.32 (d, 1H, J = 2.7Hz), 8.20 (d
d, 1H, J = 2.7Hz, 8.9Hz), 7.70 (dd, 1H, J = 1.6Hz, 9.5
Hz), 7.56 (d, 1H, J = 9.5Hz), 7.41-7.36 (m, 1H), 7.1
4 (s, 1H), 6.84 (d, 1H, J = 8.9Hz), 3.81 (s, 3H), 2.5
3 (s, 3H); MS (APCI, m / z) 381 (M + H) +, HPLC (R); R
t = 2.6 min. (Example 283) 3- [2- [acetyl- (6-methoxy-pyridin-3-yl) -amino] -thiazol-4-yl] -2-methyl-imidazo [1,2- α] pyridine-6-carboxylic acid amide Using the compound of Example 282, a reaction was carried out in the same manner as in Example 280 to obtain the title compound.

Mp 142-145 ° C .; 1H-NMR (DMSO-d6) δ: 9.00 (s, 1H), 8.34 (d, 1H, J =
2.7Hz), 8.04 (dd, 1H, J = 2.7Hz, 8.6Hz), 7.96 (brs,
1H), 7.61 (dd, 1H, J = 1.6Hz, 9.5Hz), 7.58 (s, 1H),
7.49 (d, 2H, J = 9.2Hz), 6.97 (d, 1H, J = 8.6Hz), 3.88
(s, 3H), 2.43 (s, 3H), 2.10 (s, 3H); MS (APCI, m / z): 383 (M + H) +; HPLC (R): Rt = 4.1 min. (Example 284) N- (6-Methoxy-pyridin-3-yl) -N- [4- (2-methyl-6-nitro-imidazo [1,2-α] pyridin-3-yl) -thiazol-2
-Yl] -acetamide Using the compound of Example 285, the reaction was carried out in the same manner as in Example 280 to obtain the title compound.

Mp 248-251 ° C., 1H-NMR (DMSO-d6) δ: 9.64 (d, 1H, J = 2.2 Hz), 8.40
(d, 1H, J = 2.4Hz), 8.00 (dd, 1H, J = 2.7Hz, 8.6Hz),
7.88 (dd, 1H, J = 2.2Hz, 9.5Hz), 7.66 (s, 1H), 7.64
(d, 1H, J = 8.1Hz), 6.99 (d, 1H, J = 8.6Hz), 3.92 (s,
3H), 2.57 (s, 3H), 2.09 (s, 3H); MS (APCI, m / z): 425 (M + H) +; HPLC (R): Rt = 4.2 min. (Example 285) 6-methoxy-pyridin-3-yl)-[4- (2-methyl-6-nitro
-Imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -amine The compound of Reference Example 77 and (6-methoxy-pyridin-3-
Example 1 using yl) -thiourea (Reference Example 43)
The reaction was carried out in the same manner as in to give the title compound.

Mp 234-237 ° C .; 1H-NMR (DMSO-d6) δ: 10.42 (s, 1H), 10.22 (d, 1H,
J = 2.2Hz), 8.33 (d, 1H, J = 2.7Hz), 8.18 (dd, 1H, J = 2.
7Hz, 8.9Hz), 7.96 (dd, 1H, J = 2.2Hz, 9.7Hz), 7.69
(d, 1H, J = 9.7Hz), 7.21 (s, 1H), 6.84 (d, 1H, J = 8.9
Hz), 3.83 (s, 3H), 2.60 (s, 3H); MS (APCI, m / z): 383 (M + H) +; HPLC (R): Rt = 4.2 min. (Example 286) 4- (2,6-dimethyl-imidazo [1,2-α] pyridin-3-yl)-
Thiazol-2-yl]-(6-methoxy-pyridin-3-yl) -carboxylic acid tert-butyl ester [4- (2,6-dimethyl-imidazo [1,2-α] pyridin-3-yl)-
Thiazol-2-yl]-(6-methoxy-pyridin-3-yl) -amine hydrobromide (Example 307) 400 mg (0.9
3 mmol) was suspended in 10 ml of tetrahydrofuran and 0.4 ml of triethylamine.
808 mg (3.7 mmol) of dicarbonate were added,
Stirred at 60 ° C. for 3 hours. After adding 5 ml of pyridine and further stirring for 15 hours, di-tert-butyl dicarbonate 8 was added.
08 mg (3.7 mmol) was added, and the mixture was stirred at 60 ° C. for 3 days. The residue obtained by concentrating the solvent under reduced pressure was dissolved in ethyl acetate, and washed with a saturated aqueous solution of sodium bicarbonate and subsequently with a saturated saline solution. After the organic layer was dried over anhydrous sodium sulfate, the solvent was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate) to give the title compound 2
92 mg (70%) were obtained.

Mp 182-184 ° C. (dec.); 1H-NMR (DMSO-d6) δ: 8.40 (s, 1H), 8.32 (d, 1H, J =
2.7Hz), 7.92 (dd, 1H, J = 2.7Hz, 8.9Hz), 7.41 (s, 1
H), 7.37 (d, 1H, J = 9.2Hz), 7.04 (d, 1H, J = 10.5Hz),
6.98 (d, 1H, J = 8.6Hz), 3.91 (s, 3H), 2.45 (s, 3
H), 2.10 (s, 3H), 1.44 (s, 9H); MS (APCI, m / z): 452 (M + H) +; HPLC (R): Rt = 3.8 min. (Example 287) N -[4- (8-Methoxy-2-methyl-imidazo [1,2-α] pyridine
-3-yl) -thiazol-2-yl] -N- (6-methoxy-pyridine
-3-yl) -acetamide Using the compound of Example 222, the reaction was carried out in the same manner as in Example 280 to obtain the title compound.

Mp 213-214 ° C .; 1H-NMR (DMSO-d6) δ: 8.40 (s, 1H), 8.09 (d, 1H, J =
5.7Hz), 8.00 (d, 1H, J = 8.6Hz), 7.47 (s, 1H), 7.05
(d, 1H, J = 8.6Hz), 6.64-6.56 (m, 2H), 3.93 (s, 3H),
3.89 (s, 3H), 2.41 (s, 3H), 2.10 (s, 3H); MS (APCI, m / z): 410 (M + H) +; HPLC (R): Rt = 3.1 min. Example 288) 7-bromo-3- [2- (4-methoxy-phenylamino) -thiazol-4-yl] -2-methyl-imidazo [1,2-α] pyridin-8-ol Reference Example 33 (2 Example 202 using the compound of formula (I) and (4-methoxy-phenyl) -thiourea (Reference Example 3).
The reaction was carried out in the same manner as in to give the title compound.

1H-NMR (DMSO-d6) δ: 10.18 (s, 1H), 8.
38 (d, 1H, J = 7.0Hz), 7.53 (d, 2H, J = 8.6Hz), 7.05
(d, 1H, J = 5.4Hz), 7.04 (s, 1H), 6.93 (d, 2H, J = 8.9
Hz), 3.73 (s, 3H), 2.55 (s, 3H); MS (FAB, m / z): 431 (M + H) +, 433 (M + H) +. (Example 289) 7-bromo 2-methyl-3- (2-p-tolylamino-thiazole-4
-Yl) -2-methyl-imidazo [1,2-α] pyridin-8-ol Same as Example 202 using the compound of Reference Example 33 (2) and p-tolyl-thiourea (purchased from Tokyo Chemical Industry). To give the title compound.

1H-NMR (DMSO-d6) δ: 10.30 (s, 1H), 8.
37 (d, 1H, J = 7.3Hz), 7.51 (d, 2H, J = 8.4Hz), 7.14
(d, 2H, J = 8.6Hz), 7.09 (s, 1H), 7.05 (d, 1H, J = 7.0
Hz), 2.55 (s, 3H), 2.26 (s, 3H); MS (FAB, m / z): 414 (M) +, 416 (M) +. (Example 290) 7-bromo-3- [ 2- (6-methoxy-pyridin-3-ylamino)-
Thiazol-4-yl] -2-methyl-imidazo [1,2-α] pyridin-8-ol The compound of Reference Example 33 (2) and (6-methoxy-pyridin-3-yl) -thiourea (Reference Example 43) )
The reaction was carried out in the same manner as in Example 202 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.32 (s, 1H), 8.
44 (d, 1H, J = 2.7Hz), 8.28 (d, 1H, J = 7.3Hz), 7.98
(dd, 1H, J = 3.0Hz, 8.9Hz), 7.11 (s, 1H), 7.03 (d, 1
H, J = 7.3Hz), 6.85 (d, 1H, J = 8.9Hz), 3.82 (s, 3H),
2.54 (s, 3H); MS (FAB, m / z): 431 (M) +. (Example 291) 7-bromo-2-methyl-3- [2- (4-trifluoro-phenylamino)- Thiazol-4-yl] -imidazo [1,2-α] pyridine-
8-ol Using the compound of Reference Example 33 (2) and (4-trifluoromethyl-phenyl) -thiourea (Reference Example 2), the reaction was carried out in the same manner as in Example 202 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.85 (s, 1H), 8.
30 (d, 1H, J = 7.3Hz), 7.83 (d, 2H, J = 8.6Hz), 7.70
(d, 2H, J = 8.9Hz), 7.26 (s, 1H), 7.09 (d, 1H, J = 7.3
Hz), 2.56 (s, 3H); MS (FAB, m / z) 468 (M) +. (Example 292) (4-methoxy-phenyl)-[4- (2-propyl-imidazo [1,2 -
α] pyridin-3-yl) -thiazol-2-yl] -amine Using the compound of Reference Example 55 and (4-methoxy-phenyl) -thiourea (Reference Example 3), a reaction was carried out in the same manner as in Example 188. The title compound was obtained.

1H-NMR (CDCl3) δ: 8.71 (d, 1H, J = 7.0H
z), 8.03 (brs, 1H), 7.59 (d, 1H, J = 9.2Hz), 7.25-7.1
3 (m, 3H), 6.90-6.85 (m, 2H), 6.76 (dt, 1H, J = 1.4H
z, 6.8Hz), 6.58 (s, 1H), 3.81 (s, 3H), 3.47-3.37
(m, 1H), 3.81 (s, 3H), 2.90 (t, 2H, J = 7.6Hz), 1.93
-1.79 (m, 2H), 1.02 (t, 3H, J = 7.3 Hz). (Example 293) [4- (2-propyl-imidazo [1,2-α] pyridin-3-yl) -thiazole- 2-yl]-(4-trifluoromethyl-phenyl)-
Amine Example 1 was prepared using the compound of Reference Example 55 and (4-trifluoromethyl-phenyl) -thiourea (Reference Example 2).
The reaction was carried out in the same manner as in 88 to obtain the title compound.

1H-NMR (CDCl3) δ: 8.76 (d, 1H, J = 6.8H
z), 8.26 (brs, 1H), 7.65-7.36 (m, 5H), 7.26-7.19
(m, 1H), 6.83 (t, 1H, J = 6.8Hz), 6.77 (s, 1H), 2.93
(t, 2H, J = 8.1Hz), 1.93-1.84 (m, 2H), 1.03 (t, 3H,
(Example 294) N- [4- (2-isopropyl-6-methyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -N- ( 6-Methoxy-pyridin-3-yl) -acetamide Using the compound of Example 304, the reaction was carried out in the same manner as in Example 280 to obtain the title compound.

Mp 147-148 ° C .; 1H-NMR (DMSO-d6) δ: 8.43 (s, 1H), 8.29 (s, 1H),
8.01 (d, 1H, J = 8.6Hz), 7.43 (s, 1H), 7.42 (d, 1
H, J = 7.3Hz), 7.06 (d, 1H, J = 9.2Hz), 7.04 (d, 1H,
J = 8.9Hz), 3.92 (s, 3H), 3.33 (sep, 1H, J = 6.5Hz),
2.15 (s, 3H), 2.10 (s, 3H), 1.21 (d, 6H, J = 6.75H
MS) (APCI, m / z): 422; HPLC (R): Rt = 3.4 min. (Example 295) 3- [2- (6-Methoxy-pyridin-3-ylamino) -thiazole
-4-yl] -6-methyl-imidazo [1,2-α] pyridine-2-carboxylic acid methyl ester hydrobromide Compound of Reference Example 80 and (6-methoxy-pyridine-3)
Using -yl) -thiourea (Reference Example 43), the reaction was carried out in the same manner as in Example 307 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.37 (s, 1H), 8.
73 (s, 1H), 8.46 (s, 1H), 7.98 (d, 1H, J = 8.9Hz),
7.71 (d, 1H, J = 9.7Hz), 7.60-7.50 (m, 2H), 6.84
(d, 1H, J = 8.9Hz), 3.86 (s, 3H), 3.81 (s, 3H), 2.3
5 (s, 3H); MS (APCI, m / z): 396 (M + H) +; HPLC (R): Rt = 3.7 min. (Example 296) N- (6-methoxy-pyridine-3- Yl) -N- [4- (2-methyl-6-trifluoromethyl-imidazo [1,2-α] pyridin-3-yl)-
Thiazol-2-yl] -acetamide Using the compound of Example 79, the reaction was carried out in the same manner as in Example 280 to obtain the title compound.

Mp 197-199 ° C .; 1H-NMR (DMSO-d6) δ: 9.02 (s, 1H), 8.40 (s, 1H),
7.98 (d, 1H, J = 8.9Hz), 7.68 (d, 1H, J = 9.5Hz), 7.5
9 (s, 1H), 7.41 (d, 1H, J = 9.5Hz), 6.98 (d, 1H, J = 8.
6Hz), 3.92 (s, 3H), 2.55 (s, 3H), 2.08 (s, 3H); MS (APCI, m / z): 448 (M + H) +; HPLC (R): Rt = 4.0 min Example 297 N- (6-Methoxy-pyridin-3-yl) -N- [4- (2-methyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl ] -Acetamide Using the compound of Example 61, a reaction was carried out in the same manner as in Example 280 to obtain the title compound.

Mp 168-170 ° C .; 1H-NMR (DMSO-d6) δ: 8.48 (d, 1H, J = 7.0 Hz), 8.41
(d, 1H, J = 2.7Hz), 8.01 (dd, 1H, J = 2.7Hz, 8.9Hz),
7.48 (s, 1H), 7.47 (d, 1H, J = 8.9Hz), 7.20 (dt, 1H,
J = 1.4Hz, 6.8Hz), 7.06 (d, 1H, J = 8.6Hz), 6.68 (dt,
1H, J = 1.1Hz, 6.8Hz), 3.94 (s, 3H), 2.44 (s, 3H),
2.11 (s, 3H); MS (APCI, m / z): 380 (M + H) +; HPLC (R): Rt = 2.8 min. (Example 298) N- [4- (6-amino-2) -Methyl-imidazo [1,2-α] pyridine-3
-Yl) -thiazol-2-yl] -N- (6-methoxy-pyridine-3
-Yl) -acetamido N- (6-methoxy-pyridin-3-yl) -N- [4- (2-methyl-6-nitro-imidazo [1,2-α] pyridin-3-yl) -thiazole- Two
-Yl] -acetamide (Example 284) 830 mg
(1.96 mmol) was dissolved in 40 ml of methanol, and 1.92 g of zinc powder was added. Acetic acid 1.6
Then, the mixture was heated and refluxed for 2 hours.
The reaction was cooled to room temperature and the reaction was filtered using celite. The filtrate was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography (dichloromethane / methanol = 1).
After purification in 0: 1), the obtained crystals were finely ground, washed with hexane-ethyl acetate, and 340 mg of the title compound
(44%).

1H-NMR (DMSO-d6) δ: 8.40 (d, 1H, J = 3.
0Hz), 8.01 (dd, 1H, J = 3.0Hz, 9.2Hz), 7.83 (s, 1H),
7.36 (s, 1H), 7.24 (d, 1H, J = 9.5Hz), 7.06 (d, 1H,
J = 8.6Hz), 6.79 (dd, 1H, J = 1.9Hz, 9.2Hz), 4,61 (br
s, 2H), 3.91 (s, 3H), 2.30 (s, 3H), 2.10 (s, 3H); MS (APCI, m / z): 395 (M + H) +; HPLC (R): Rt = 2.8 min. (Example 299) N- [4- (2,6-dimethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -N- (6-methoxy-pyridine -3-yl) -isobutylamide Using the compound of Example 307 and substituting isobutylic anhydride for acetic anhydride of Example 280, the reaction was carried out in the same manner as in Example 280 to obtain the title compound.

Mp 196-198 ° C .; 1H-NMR (DMSO-d6) δ: 8.51 (d, 1H, J = 2.4 Hz), 8.37
(brs, 1H), 8.10 (dd, 1H, J = 2,7Hz, 8.6Hz), 7.44 (s,
1H), 7.37 (d, 1H, J = 9.2Hz), 7.09-7.03 (m, 2H), 3.93
(s, 3H), 2.46 (s, 3H), 2.33 (brq, 2H, J = 7.2Hz),
2.10 (s, 3H), 1.06 (t, 3H, J = 7.2 Hz); MS (APCI, m / z): 422 (M + H) +; HPLC (R): Rt = 3.6 min. (Example 300 ) N- [4- (2,6-dimethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -N- (6-methoxy-pyridin-3-yl) -propioamide The title compound was obtained by using the compound of Example 307 and performing a reaction in the same manner as in Example 280 using propionic anhydride instead of acetic anhydride in Example 280.

Mp 208 ° C. (decomp); 1H-NMR (DMSO-d6) δ: 8.44 (d, 1H, J = 2.4 Hz), 8.39
(brs, 1H), 8.02 (dd, 1H, J = 2,7Hz, 8.9Hz), 7.42 (s,
1H), 7.37 (d, 1H, J = 8.9Hz), 7.08-7.02 (m, 2H), 3.94
(s, 3H), 2.63 (sep, 1H, J = 6.5Hz), 2.46 (s, 3H),
2.11 (s, 3H), 1.09 (d, 6H, J = 6.5 Hz); MS (APCI, m / z) 408 (M + H) +; HPLC (R): Rt = 3.4 min. (Example 301) [4- (2,6-dimethyl-imidazo [1,2-α] pyridin-3-yl)-
Thiazol-2-yl]-(6-methoxy-pyridin-3-yl) -carbamic acid methyl ester [4- (2,6-dimethyl-imidazo [1,2-α] pyridin-3-yl)-
Thiazol-2-yl]-(6-methoxy-pyridin-3-yl) -amine hydrobromide (Example 307) 600 mg (1.3
9 mmol) was suspended in 20 ml of acetone, 390 mg (6.94 mmol) of potassium hydroxide dissolved in 0.18 ml of water was added, and the mixture was heated to 60 ° C. 0.54 ml (6.94 mmol) of methyl chloroformate was added,
Stirred at 60 ° C. for 1 hour. The reaction solution was filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was dissolved in ethyl acetate, and washed with water and then with a saturated saline solution. After the organic layer was dried over anhydrous sodium sulfate, the solvent was concentrated under reduced pressure. The obtained crystals were pulverized finely and washed with hexane-ethyl acetate to obtain 450 mg (79%) of the title compound.

Mp 164-166 ° C .; 1H-NMR (DMSO-d6) δ: 8.39-8.37 (m, 2H), 7.95 (dd,
1H, J = 2.4Hz, 8.6Hz), 7.43 (s, 1H), 7.37 (d, 1H, J =
8.9Hz), 7.06-6.98 (m, 2H), 3.91 (s, 3H), 3.80 (s,
3H), 2.46 (s, 3H), 2.10 (s, 3H); MS (APCI, m / z): 410 (M + H) +; HPLC (R): Rt = 3.2 min. (Example 302) 1 -[4- (2,6-Dimethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -1- (6-methoxy-pyridin-3-yl) -3,3 -Dimethyl-urea [4- (2,6-dimethyl-imidazo [1,2-α] pyridin-3-yl)-
Thiazol-2-yl]-(6-methoxy-pyridin-3-yl) -amine hydrobromide (Example 307) 600 mg (1.3
9 mmol) was suspended in 20 ml of acetone, 390 mg (6.94 mmol) of potassium hydroxide dissolved in 0.18 ml of water was added, and the mixture was heated to 60 ° C. 0.64 ml (6.94 mmol) of dimethylcarbamoyl chloride
Was added and stirred at 60 ° C. for 1 hour. The reaction solution was filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was dissolved in ethyl acetate, and washed with water and then with a saturated saline solution. After the organic layer was dried over anhydrous sodium sulfate, the solvent was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate) to obtain 493 mg (84%) of the title compound.

Mp 140-142 ° C .; 1H-NMR (DMSO-d6) δ: 8.56 (s, 1H), 8.34 (d, 1H, J =
2.7Hz), 7.97 (dd, 1H, J = 2.7Hz, 8.9Hz), 7.40 (d, 1
H, J = 9.2Hz), 7.34 (s, 1H), 7.09 (dd, 1H, J = 1.9Hz,
9.2Hz), 6.98 (d, 1H, J = 8.9Hz), 3.91 (s, 3H), 2.80
(s, 6H), 2.47 (s, 3H), 2.21 (s, 3H); MS (APCI, m / z) 423 (M + H) +; HPLC (R): Rt = 3.1 min. (Example 303 ) N- [4- (8-Methoxy-2-methyl-imidazo [1,2-α] pyridine
-3-yl) -thiazol-2-yl] -N- (4-trifluoromethyl-phenyl) -acetamide The compound of Example 223 was used and reacted in the same manner as in Example 280 to obtain the title compound. .

1H-NMR (DMSO-d6) δ: 8.03-7.99 (m, 3
H), 7.89 (d, 2H, J = 8.6Hz), 7.47 (s, 1H), 6.63 (d,
1H, J = 7.3Hz), 6.46 (t, 1H, J = 7.3Hz), 3.87 (s, 3H),
2.41 (s, 3H), 2.09 (s, 3H); MS (APCI, m / z) 447 (M + H) +; HPLC (R): Rt = 3.6 min (Example 304) [4- (2- Isopropyl-6-methyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl]-(6-methoxy-pyridine
-3-yl) -amine The compound of Reference Example 83 and (6-methoxy-pyridine-3)
Using -yl) -thiourea (Reference Example 43), the reaction was carried out in the same manner as in Example 1 to obtain the title compound.

Mp 258-260 ° C .; 1H-NMR (DMSO-d6) δ: 10.35-10.25 (brs, 1H), 8.58
(s, 1H), 8.46 (s, 1H), 8.03 (d, 1H, J = 8.9Hz), 7.4
9 (d, 1H, J = 9.2Hz), 7.13 (d, 1H, J = 9.2Hz), 7.02
(s, 1H), 6.83 (d, 1H, J = 8.9Hz), 3.82 (s, 3H), 3.3
5 (sep, 1H, J = 6.8Hz), 2.29 (s, 3H), 1.29 (d, 6H, J
= 6.8 Hz); MS (APCI, m / z): 380; HPLC (R): Rt = 3.3 min. (Example 305) 3- [2- (6-Methoxy-pyridin-3-ylamino) -thiazole
-4-yl] -6-methyl-imidazo [1,2-α] pyridine-2-carboxylic acid amide Using the compound of Example 295, hydrolysis was carried out in the same manner as in Example 151. The reaction was carried out in the same manner as in 235 to obtain the title compound.

Mp 256-258 ° C .; 1H-NMR (DMSO-d6) δ: 10.27 (s, 1H), 8.92 (s, 1H),
8.46 (s, 1H), 7.99 (d, 1H, J = 8.9Hz), 7.85-7.70
(m, 2H), 7.58 (d, 1H, J = 9.2Hz), 7.45-7.35 (brs, 1
H), 7.29 (d, 1H, J = 9.5Hz), 6.84 (d, 1H, J = 8.6Hz),
3.82 (s, 3H), 2.31 (s, 3H); MS (APCI, m / z): 381 (M + H) +; HPLC (R): Rt = 3.3 min. (Example 306) 3- [2 -[Acetyl- (6-methoxy-pyridin-3-yl) -amino] -thiazol-4-yl] -6-methyl-imidazo [1,2-α] pyridine-2-carboxylic acid amide Compound of Example 305 And the reaction was carried out in the same manner as in Example 280 to obtain the title compound.

Mp 291-294 ° C .; 1H-NMR (DMSO-d6) δ: 8.52 (s, 1H), 8.47 (s, 1H),
8.46 (s, 1H), 8.04 (d, 1H, J = 8.9Hz), 7.85-7.70
(brs, 1H), 7.73 (d, 1H, J = 8.6Hz), 7.45-7.35 (brs, 1H
H), 7.19 (d, 1H, J = 9.2Hz), 7.06 (d, 1H, J = 8.9H
z), 3.93 (s, 3H), 2.12 (s, 3H), 2.09 (s, 3H); MS (APCI, m / z): 423 (M + H) +; HPLC (R): Rt = 3.6 min Example 307 [4- (2,6-Dimethyl-imidazo [1,2-α] pyridin-3-yl)-
Thiazol-2-yl]-(6-methoxy-pyridin-3-yl) -amine hydrobromide 2-bromo-1- (2,6-dimethyl-imidazo [1,2-α] pyridine-
3.14 g (11.8 mmol) of (3-yl) -ethanone (Reference Example 5) and 2.15 g (3.14 mmol) of (6-methoxy-pyridin-3-yl) -thiourea (Reference Example 43)
Was dissolved in 400 ml of ethanol and stirred at 70 ° C. for 14 hours. The solvent was concentrated under reduced pressure to about 50 ml, and about 50 ml of ethyl acetate and about 150 ml of hexane were added to precipitate crystals. This was filtered to obtain 4.83 g (yield 98%) of the title compound.

1H-NMR (DMSO-d6) δ: 10.47 (s, 1H), 9.
03 (s, 1H), 8.47 (d, 1H, J = 2.4Hz), 7.99 (dd, 1H, J
= 2.7Hz, 8.9Hz), 7.90 (d, 1H, J = 9.2Hz), 7.82 (dd, 1
H, J = 1.4Hz, 9.2Hz), 7.43 (s, 1H), 6.85 (d, 1H, J = 8.
6Hz), 3.83 (s, 3H), 2.62 (s, 3H), 2.44 (s, 3H); MS (APCI, m / z): 352 (M + H) +; HPLC (R): Rt = 3.1 min Example 308 N- [4- (8-methoxy-2-methyl-imidazo [1,2-α] pyridine)
-3-yl) -thiazol-2-yl] -Np-tolyl-acetamide Using the compound of Example 220, the reaction was carried out in the same manner as in Example 280 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 8.09 (d, 1H, J = 5.
7Hz), 7.60-7.30 (m, 5H), 6.70-6.40 (m, 2H), 3.88
(s, 3H), 2.42 (s, 3H), 2.41 (s, 3H), 2.06 (s, 3H); MS (APCI, m / z): 393 (M + H) +; HPLC (R): Rt = 3.5 min. (Example 309) N- [4- (8-methoxy-2-methyl-imidazo [1,2-α] pyridine)
-3-yl) -thiazol-2-yl] -N- (4-methoxy-phenyl) -acetamide Using the compound of Example 218, the reaction was carried out in the same manner as in Example 280 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 8.13 (d, 1H, J = 6.
5Hz), 7.49 (d, 2H, J = 6.5Hz), 7.43 (s, 1H), 7.13
(d, 1H, J = 8.9Hz), 6.65-6.50 (m, 2H), 3.88 (s, 3H),
3.84 (s, 3H), 2.42 (s, 3H), 2.07 (s, 3H); MS (APCI, m / z): 409 (M + H) +; HPLC (R): Rt = 3.3 min. Example 310) [4- (2-Methyl-imidazo [1,2-β] isoquinolin-3-yl)-
Thiazol-2-yl]-(4-trifluoromethyl-phenyl)
-Amine The reaction was carried out in the same manner as in Example 1 using the compound of Reference Example 16 and (4-trifluoromethyl-phenyl) -thiourea (Reference Example 2) to obtain the title compound.

1H-NMR (CDCl3) δ: 9.77 (s, 1H), 8.10
(s, 1H), 7.75-7.65 (m, 4H), 7.30-7.26 (m, 4H), 6.8
7-6.82 (m, 2H), 2.78 (s, 3H); MS (APCI, m / z): 425 (M + H) +; HPLC (N): Rt = 6.4 min. (Example 311) 4- [4- (2-Methyl-imidazo [1,2-β] isoquinolin-3-yl) -thiazol-2-ylamino] -benzoic acid ethyl ester The compound of Reference Example 16 and 4-thioureido-ethyl benzoate (Reference Example) Using 49), a reaction was carried out in the same manner as in Example 1 to obtain the title compound.

1H-NMR (CDCl3) δ: 9.79 (s, 1H), 8.08
(d, 2H, J = 8.9Hz), 8.06 (s, 1H), 7.74 (t, 2H, J = 8.9H
z), 7.58 (d, 2H, J = 8.9Hz), 7.32-7.26 (m, 3H), 6.82
(s, 1H), 4,38 (q, 2H, J = 7.0Hz), 2.77 (s, 3H), 1.41
(t, 3H, J = 7.0Hz); MS (APCI, m / z): 429 (M + H) +; HPLC (N): Rt = 7.4 min. (Example 312) (4-methoxy-phenyl) -[4- (2-Methyl-imidazo [1,2-
α] Quinolin-1-yl) -thiazol-2-yl] -amine 2-bromo-1- (2-methyl-imidazo [1,2-α] quinolin-1-
17 mg (56.5 μmol) of (yl) -ethanone (Reference Example 17) and 10.3 mg (56.5 μmol) of (4-methoxy-phenyl) -thiourea (Reference Example 3) were dissolved in 1 ml of ethanol. Heated to reflux for an hour. Ethyl ether was added to the reaction solution, the suspension was filtered, and the crystals were washed with ethyl ether.
l and methanol (1 ml), aminomethylated polystyrene resin (100 mg, 67 micromol, 0.67 mmol / g) was added, and the mixture was stirred at room temperature for 3 minutes. The reaction solution was filtered, and the filtrate was concentrated under reduced pressure. The obtained crystals were finely pulverized and washed with hexane-ethyl ether to obtain 12.5 mg of the title compound.

1H-NMR (DMSO-d6) δ: 10.20 (s, 1H), 7.
96 (d, 1H, J = 7.3Hz), 7.72 (d, 1H, J = 9.2Hz), 7.65
(d, 1H, J = 8.4Hz), 7.54 (d, 1H, J = 9.2Hz), 7.50-7.41
(m, 4H), 7.16 (d, 1H, J = 2.7Hz), 6.80 (dd, 2H, J = 2.
7Hz, 9.2Hz), 3.65 (s, 3H), 2.31 (s, 3H); MS (APCI, m / z): 387 (M + H) +; HPLC (N): Rt = 4.3 min. 313) (4-Methoxy-phenyl)-[4- (2-methyl-imidazo [2,1-
α] isoquinolin-3-yl) -thiazol-2-yl] -amine 2-bromo-1- (2-methyl-imidazo [2,1-α] isoquinoline-
A reaction was carried out in the same manner as in Example 1 using (3-yl) -ethanone (Reference Example 17) and (4-methoxy-phenyl) -thiourea (Reference Example 3) to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.21 (s, 1H), 8.7
8 (d, 1H, J = 7.6Hz), 8.47 (d, 1H, J = 7.3Hz), 7.90-7.8
6 (m, 1H), 7.67-7.62 (m, 2H), 7.57 (d, 2H, J = 8.6H
z), 7.31 (d, 1H, J = 7.3Hz), 7.06 (s, 1H), 6.94 (d, 1
H, J = 9.2Hz), 3.74 (s, 3H), 2.57 (s, 3H); MS (APCI, m / z): 387 (M + H) +; HPLC (N): Rt = 5.1 min. Example 314) 1- [4- [4- (2-methyl-imidazo [2,1-α] isoquinoline-3-
Yl) -thiazol-2-ylamino] -phenyl] -ethanone 2-bromo-1- (2-methyl-imidazo [2,1-α] isoquinoline-
Example 1 was prepared using (3-yl) -ethanone (Reference Example 17) and (4-acetyl-phenyl) -thiourea (Reference Example 47).
The reaction was carried out in the same manner as in to give the title compound.

1H-NMR (DMSO-d6) δ: 10.90 (s, 1H), 8.7
3 (d, 1H, J = 7.3Hz), 8.52-8.49 (m, 1H), 7.98 (d, 2
H, J = 8.9Hz), 7.90-7.87 (m, 1H), 7.78 (d, 2H, J = 8.4
Hz), 7.67-7.65 (m, 2H), 7.35 (d, 1H, J = 7.8Hz), 7.29
(s, 1H), 2.59 (s, 3H), 2.49 (s, 3H); MS (APCI, m / z): 399 (M + H) +; HPLC (N): Rt = 4.8 min. 315) [4- (2-Methyl-imidazo [2,1-α] isoquinolin-3-yl)-
Thiazol-2-yl] -p-tolyl-amine 2-bromo-1- (2-methyl-imidazo [2,1-α] isoquinoline-
The reaction was carried out in the same manner as in Example 1 using 3-yl) -ethanone (Reference Example 17) and p-tolyl-thiourea (purchased from Tokyo Chemical Industry) to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.32 (s, 1H), 8.
78 (d, 1H, J = 7.3Hz), 8.50-8.47 (m, 1H), 7.90-7.87
(m, 1H), 7.70-7.61 (m, 2H), 7.54 (d, 2H, J = 8.6Hz),
7.31 (d, 1H, J = 7.8Hz), 7.15 (d, 2H, J = 8.6Hz), 7.1
0 (s, 1H), 2.57 (s, 3H), 2.26 (s, 3H); MS (APCI, m / z): 371 (M + H) +; HPLC (N): Rt = 5.7 min. Example 316) 4- [4- (2-Methyl-imidazo [2,1-α] isoquinolin-3-yl) -thiazol-2-ylamino] -benzoic acid ethyl ester 2-bromo-1- (2-methyl- Imidazo [2,1-α] isoquinoline-
Using 3-yl) -ethanone (Reference Example 17) and 4-thioureido-ethyl benzoate (Reference Example 49), the reaction was carried out in the same manner as in Example 1 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.90 (s, 1H), 8.7
3 (d, 1H, J = 7.6Hz), 8.51-8.48 (m, 1H), 7.96-7.88
(m, 3H), 7.79 (d, 2H, J = 8.6Hz), 7.71-7.64 (m, 2H),
7.35 (d, 1H, J = 7.6Hz), 7.28 (s, 1H), 4.28 (q, 2H,
J = 7.0Hz), 2.59 (s, 3H), 1.31 (t, 3H, J = 7.0Hz); MS (APCI, m / z): 429 (M + H) +; HPLC (N): Rt = 5.6 min. (Example 317) (6-Methoxy-pyridin-3-yl)-[4- (2-methyl-imidazo)
[2,1-α] isoquinolin-3-yl) -thiazol-2-yl] -amine 2-bromo-1- (2-methyl-imidazo [2,1-α] isoquinoline-
The reaction was carried out in the same manner as in Example 1 using (3-yl) -ethanone (Reference Example 17) and (6-methoxy-pyridin-3-yl) -thiourea (Reference Example 43) to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.35 (s, 1H), 8.7
0 (d, 1H, J = 7.0Hz), 8.50-8.46 (m, 2H), 8.02-7.98
(m, 1H), 7.90-7.88 (m, 2H), 7.66-7.63 (m, 1H), 7.3
0 (d, 1H, J = 6.8Hz), 7.12 (s, 1H), 6.85 (d, 1H, J = 9.
2Hz), 3.82 (s, 3H), 2.56 (s, 3H); MS (APCI, m / z): 388 (M + H) +; HPLC (N): Rt = 4.7 min. (Example 318) 4- (2-methyl-imidazo [2,1-α] isoquinolin-3-yl)-
Thiazol-2-yl]-(4-trifluoromethyl-phenyl)
-Amine 2-bromo-1- (2-methyl-imidazo [2,1-α] isoquinoline-
Using (3-yl) -ethanone (Reference Example 17) and (4-trifluoromethyl-phenyl) -thiourea (Reference Example 2),
The reaction was carried out in the same manner as in Example 1 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.89 (s, 1H), 8.7
0 (d, 1H, J = 7.6Hz), 8.51-8.47 (m, 1H), 7.91-7.85
(m, 3H), 7.71-7.64 (m, 4H), 7.34 (d, 1H, J = 7.6Hz),
7.27 (s, 1H), 2.58 (s, 3H); MS (APCI, m / z): 425 (M + H) +; HPLC (N): Rt = 6.0 min. (Example 319) 4- [4 -(2-Methyl-imidazo [2,1-α] isoquinolin-3-yl) -thiazol-2-ylamino] -benzonitrile 2-bromo-1- (2-methyl-imidazo [2,1-α] isoquinoline -
A reaction was carried out in the same manner as in Example 1 using (3-yl) -ethanone (Reference Example 17) and (4-cyano-phenyl) -thiourea (Reference Example 48) to obtain the title compound.

1H-NMR (DMSO-d6) δ: 11.00 (s, 1H), 8.
66 (d, 1H, J = 7.6Hz), 8.49 (d, 1H, J = 8.6Hz), 7.91-
7.77 (m, 5H), 7.71-7.65 (m, 2H), 7.33 (d, 1H, J = 8.
6Hz), 7.32 (s, 1H), 2.56 (s, 3H); MS (APCI, m / z): 382 (M + H) +; HPLC (N): Rt = 5.0 min. (Example 320) 1 -[4- [4- (2-Methyl-imidazo [1,2-α] quinolin-1-yl)
-Thiazol-2-ylamino] -phenyl] -ethanone Using the compound of Reference Example 57 and (4-acetyl-phenyl) -thiourea (Reference Example 47), the reaction was carried out in the same manner as in Example 312 to obtain the title compound. Was.

1H-NMR (DMSO-d6) δ: 10.88 (s, 1H), 7.
99-7.96 (m, 1H), 7.81 (d, 2H, J = 8.9Hz), 7.74 (d, 1
H, J = 9.5Hz), 7.64 (d, 2H, J = 8.9Hz), 7.60-7.54 (m,
1H), 7.50-7.43 (m, 3H), 7.38 (s, 1H), 2.43 (s, 3H),
2.32 (s, 3H). (Example 321) [4- (2-Methyl-imidazo [1,2-α] quinolin-1-yl) -thiazol-2-yl] -p-tolyl-amine Reference Example 57 Using the compound of formula (1) and p-tolyl-thiourea (purchased from Tokyo Chemical Industry), the reaction was carried out in the same manner as in Example 312 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.32 (s, 1H), 8.
00 (d, 1H, J = 7.0Hz), 7.80 (d, 1H, J = 9.5Hz), 7.66
(d, 1H, J = 8.4Hz), 7.59 (d, 1H, J = 9.5Hz), 7.55-7.47
(m, 2H), 7.42 (d, 2H, J = 8.1Hz), 7.23 (s, 1H), 7.00
(d, 2H, J = 8.1 Hz), 2.33 (s, 3H), 2.18 (s, 3H). (Example 322) 4- [4- (2-methyl-imidazo [1,2-α] quinoline- 1-yl) -thiazol-2-ylamino] -benzoic acid ethyl ester Using the compound of Reference Example 57 and 4-thioureido-ethyl benzoate (Reference Example 49), a reaction was carried out in the same manner as in Example 312 to give the title compound I got

1H-NMR (DMSO-d6) δ: 10.87 (s, 1H), 8.0
0 (d, 1H, J = 9.5Hz), 7.80-7.45 (m, 3H), 7.66-7.56 (m,
4H), 7.51-7.45 (m, 2H), 7.39 (s, 1H), 4.22 (q, 2
(H, J = 7.0 Hz), 2.33 (s, 3H), 1.26 (t, 3H, J = 7.0 Hz). (Example 323) (6-Methoxy-pyridin-3-yl)-[4- (2- Methyl-imidazo
[1,2-α] quinolin-1-yl) -thiazol-2-yl] -amine The compound of Reference Example 57 and (6-methoxy-pyridin-3-
Using yl) -thiourea (Reference Example 43) (Reference Example 49), the reaction was carried out in the same manner as in Example 312 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.37 (s, 1H), 8.3
6 (d, 1H, J = 3.0Hz), 8.02 (d, 1H, J = 7.3Hz), 7.89-7.8
3 (m, 2H), 7.69-7.50 (m, 4H), 7.27 (s, 1H), 6.70
(d, 1H, J = 8.9 Hz), 3.73 (s, 3H), 2.34 (s, 3H). (Example 324) [4- (2-Methyl-imidazo [1,2-α] quinoline-1- Yl) -thiazol-2-yl]-(4-trifluoromethyl-phenyl) -amine Example 31 was prepared using the compound of Reference Example 57 and (4-trifluoromethyl-phenyl) -thiourea (Reference Example 2).
The reaction was carried out in the same manner as in Example 2 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.85 (s, 1H), 7.
97 (d, 1H, J = 7.0Hz), 7.75-7.72 (m, 3H), 7.61-7.53
(m, 4H), 7.50-7.41 (m, 2H), 7.37 (s, 1H), 2.32 (s,
3H). Example 325 4- [4- (2-Methyl-imidazo [1,2-α] quinolin-1-yl) -thiazol-2-ylamino] -benzonitrile The compound of Reference Example 57 and (4 Using -cyano-phenyl) -thiourea (Reference Example 48), the reaction was carried out in the same manner as in Example 1 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.97 (s, 1H), 8.
00-7.97 (m, 1H), 7.75-7.54 (m, 7H), 7.46-7.41 (m,
(3H), 2.31 (s, 3H). (Example 326) (4-Methoxy-phenyl)-[4- (2-methyl-imidazo [1,2-
β] isoquinolin-3-yl) -thiazol-2-yl] -amine hydrobromide Using the compound of Reference Example 16 and (4-methoxy-phenyl) -thiourea (Reference Example 3), The reaction was performed in the same manner to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.36 (s, 1H), 1
0.14 (s, 1H), 8.53 (s, 1H), 8.19 (d, 2H, J = 8.6Hz),
7.75-7.72 (m, 1H), 7.65-7.58 (m, 3H), 7.44 (s, 1
H), 6.94 (d, 2H, J = 8.9Hz), 3.73 (s, 3H), 2.75 (s,
3H). (Example 327) 1- [4- [4- (2-methyl-imidazo [1,2-β] isoquinoline-3-
Yl) -thiazol-2-ylamino] -phenyl] -ethanone hydrobromide Using the compound of Reference Example 16 and (4-acetyl-phenyl) -thiourea (Reference Example 47), reacted in the same manner as in Example 157. To give the title compound.

1H-NMR (DMSO-d6) δ: 11.05 (s, 1H), 1
0.10 (s, 1H), 8.56 (s, 1H), 8.24-8.18 (m, 2H), 7.9
5 (d, 2H, J = 8.7Hz), 7.83-7.75 (m, 3H), 7.67 (s, 1
H), 7.65-7.60 (m, 1H), 3.60 (s, 3H), 2.50 (s, 3H). (Example 328) [4- (2-Methyl-imidazo [1,2-β] isoquinoline-3) -Il)-
Thiazol-2-yl] -p-tolyl-amine hydrobromide Using the compound of Reference Example 16 and p-tolyl-thiourea (purchased from Tokyo Chemical Industry), a reaction was conducted in the same manner as in Example 157, and the title compound was obtained. I got

1H-NMR (DMSO-d6) δ: 10.50 (s, 1H), 1
0.16 (s, 1H), 8.56 (s, 1H), 8.20 (d, 2H, J = 8.1Hz),
7.81-7.75 (m, 1H), 7.68-7.62 (m, 1H), 7.58 (d, 2H,
J = 8.2Hz), 7.50 (s, 1H), 7.15 (d, 2H, J = 8.2Hz), 2.
Example 329 4- [4- (2-Methyl-imidazo [1,2-β] isoquinolin-3-yl) -thiazol-2-ylamino] 76 (s, 3H), 2.27 (s, 3H). -Ethyl benzoate Ester hydrobromide Using the compound of Reference Example 16 and 4-thioureido-ethyl benzoate (Reference Example 49), the reaction was carried out in the same manner as in Example 157 to obtain the title compound.

MS (APCI, m / z): 429 (M-Br) +; HPLC (N): Rt = 5.6 min. (Example 330) (6-methoxy-pyridin-3-yl)-[4- (2-methyl-imidazo
[1,2-β] isoquinolin-3-yl) -thiazol-2-yl] -amine hydrobromide Compound of Reference Example 16 and (6-methoxy-pyridin-3-
Example 1 using yl) -thiourea (Reference Example 43)
The reaction was carried out in the same manner as in 57 to give the title compound.

1H-NMR (DMSO-d6) δ: 10.49 (s, 1H), 1
0.12 (s, 1H), 8.55-8.53 (m, 2H), 8.23-8.16 (m, 2H),
8.05-8.00 (m, 1H), 7.80-7.74 (m, 1H), 7.66-7.63
(m, 1H), 7.49 (s, 1H), 6.85 (d, 1H, J = 8.9Hz), 3.82
(s, 3H), 2.74 (s, 3H). (Example 331) [4- (2-Methyl-imidazo [1,2-β] isoquinolin-3-yl)-
Thiazol-2-yl]-(4-trifluoromethyl-phenyl)
-Amine hydrobromide Example 15 was prepared using the compound of Reference Example 16 and (4-trifluoromethyl-phenyl) -thiourea (Reference Example 2).
The reaction was carried out in the same manner as in Example 7 to obtain the title compound.

1H-NMR (DMSO-d6) δ; 11.04 (s, 1H), 1
0.07 (s, 1H), 8.57 (s, 1H), 8.25-8.19 (m, 2H), 7.9
0 (d, 2H, J = 8.7Hz), 7.81-7.75 (m, 1H), 7.68 (d, 2
(H, J = 8.7 Hz), 7.70-7.61 (m, 2H), 2.76 (s, 3H). (Example 332) 4- [4- (2-methyl-imidazo [1,2-β] isoquinoline-3) -Yl) -thiazol-2-ylamino] -benzonitrile hydrobromide Using the compound of Reference Example 16 and (4-cyano-phenyl) -thiourea (Reference Example 48), a reaction was carried out in the same manner as in Example 157. This gave the title compound.

1H-NMR (DMSO-d6) δ: 11.17 (s, 1H), 1
0.08 (s, 1H), 8.58 (s, 1H), 8.26-8.20 (m, 2H), 7.8
8-7.77 (m, 5H), 7.70-7.63 (m, 2H), 2.76 (s, 3H). (Example 333) (4-Methoxy-phenyl)-[4- (2-methyl-imidazo [2, 1-
α] isoquinolin-3-yl) -thiazol-2-yl] -amine hydrobromide 2-bromo-1- (2-methyl-imidazo [2,1-α] isoquinoline-
Example 15 was performed using (3-yl) -ethanone (Reference Example 17) and (4-methoxy-phenyl) -thiourea (Reference Example 3).
The reaction was carried out in the same manner as in Example 7 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.33 (s, 1H), 8.
91 (d, 1H, J = 7.8Hz), 8.62-8.57 (m, 1H), 8.15-8.10
(m, 1H), 7.92-7.89 (m, 2H), 7.79-7.72 (m, 1H), 7.5
6 (d, 2H, J = 8.9Hz), 7.33 (s, 1H), 6.94 (d, 2H, J =
(8.9 Hz), 3.73 (s, 3H), 2.67 (s, 3H). (Example 334) 1- [4- [4- (2-methyl-imidazo [2,1-α] isoquinoline-3-)
Yl) -thiazol-2-ylamino] -phenyl] -ethanone hydrobromide 2-bromo-1- (2-methyl-imidazo [2,1-α] isoquinoline-
Example 1 was prepared using (3-yl) -ethanone (Reference Example 17) and (4-acetyl-phenyl) -thiourea (Reference Example 47).
The reaction was carried out in the same manner as in 57 to give the title compound.

1H-NMR (DMSO-d6) δ: 11.00 (s, 1H), 8.
86 (d, 1H, J = 7.8Hz), 8.62-8.58 (m, 1H), 8.13-8.10
(m, 1H), 7.98 (d, 2H, J = 8.6Hz), 7.96-7.85 (m, 2H),
7.80-7.77 (m, 1H), 7.79 (d, 2H, J = 8.6Hz), 7.53
(s, 1H), 2.69 (s, 3H), 2.49 (s, 3H). (Example 335) [4- (2-Methyl-imidazo [2,1-α] isoquinolin-3-yl)-
Thiazol-2-yl] -p-tolyl-amine hydrobromide 2-bromo-1- (2-methyl-imidazo [2,1-α] isoquinoline-
The reaction was carried out in the same manner as in Example 157 using 3-yl) -ethanone (Reference Example 17) and p-tolyl-thiourea (purchased from Tokyo Chemical Industry) to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.45 (s, 1H), 8.
92 (d, 1H, J = 7.3Hz), 8.61-8.59 (m, 1H), 8.15-8.10
(m, 1H), 7.93-7.91 (m, 2H), 7.80-7.78 (m, 1H), 7.5
4 (d, 2H, J = 8.4Hz), 7.39 (s, 1H), 7.15 (d, 2H, J =
8.4 Hz), 2.69 (s, 3H), 2.27 (s, 3H). (Example 336) 4- [4- (2-methyl-imidazo [2,1-α] isoquinolin-3-yl) -thiazole- 2-ylamino] -benzoic acid ethyl ester hydrobromide 2-bromo-1- (2-methyl-imidazo [2,1-α] isoquinoline-
The reaction was carried out in the same manner as in Example 157 using 3-yl) -ethanone (Reference Example 17) and ethyl 4-thioureido-benzoate (Reference Example 49) to obtain the title compound.

1H-NMR (DMSO-d6) δ: 11.00 (s, 1H), 8.
87 (d, 1H, J = 7.3Hz), 8.63-8.60 (m, 1H), 8.15-8.10
(m, 1H), 7.97-7.90 (m, 5H), 7.79 (d, 2H, J = 8.9Hz),
7.55 (s, 1H), 4.25 (q, 2H, J = 7.0Hz), 2.70 (s, 3
H), 1.31 (t, 3H, J = 7.0 Hz). (Example 337) (6-Methoxy-pyridin-3-yl)-[4- (2-methyl-imidazo
[2,1-α] isoquinolin-3-yl) -thiazol-2-yl] -amine hydrobromide 2-bromo-1- (2-methyl-imidazo [2,1-α] isoquinoline-
The same reaction as in Example 157 was carried out using (3-yl) -ethanone (Reference Example 17) and (6-methoxy-pyridin-3-yl) -thiourea (Reference Example 43) to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.47 (s, 1H), 8.
85 (d, 1H, J = 7.6Hz), 8.60-8.57 (m, 1H), 8.16-8.13
(m, 1H), 7.99-7.90 (m, 3H), 7.80-7.75 (m, 1H), 7.4
1 (s, 1H), 6.85 (d, 2H, J = 8.1Hz), 3.82 (s, 3H), 2.
Example 338. [4- (2-Methyl-imidazo [2,1-α] isoquinolin-3-yl)-
Thiazol-2-yl]-(4-trifluoromethyl-phenyl)
-Amine hydrobromide 2-bromo-1- (2-methyl-imidazo [2,1-α] isoquinoline-
Using (3-yl) -ethanone (Reference Example 17) and (4-trifluoromethyl-phenyl) -thiourea (Reference Example 2),
The reaction was carried out in the same manner as in Example 157 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.10 (s, 1H), 8.
85 (d, 1H, J = 7.6Hz), 8.61-8.59 (m, 1H), 8.14-8.10
(m, 1H), 7.92-7.86 (m, 4H), 7.80-7.75 (m, 1H), 7.7
0 (d, 2H, J = 8.9 Hz), 7.55 (s, 1H), 2.69 (s, 3H). (Example 339) 4- [4- (2-methyl-imidazo [2,1-α] isoquinoline -3-yl) -thiazol-2-ylamino] -benzonitrile hydrobromide 2-bromo-1- (2-methyl-imidazo [2,1-α] isoquinoline-
Example 15 was performed using (3-yl) -ethanone (Reference Example 17) and (4-cyano-phenyl) -thiourea (Reference Example 48).
The reaction was carried out in the same manner as in Example 7 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 11.10 (s, 1H), 8.
80 (d, 1H, J = 7.6Hz), 8.61-8.59 (m, 1H), 8.12-8.10
(m, 1H), 7.92-7.90 (m, 1H), 7.85-7.70 (m, 6H), 7.5
8 (s, 1H), 2.68 (s, 3H). (Example 340) (4-Methoxy-phenyl)-[4- (2-methyl-imidazo [1,2-
α] quinolin-1-yl) -thiazol-2-yl] -amine hydrobromide Example 157 was prepared using the compound of Reference Example 57 and (4-methoxy-phenyl) -thiourea (Reference Example 3). The reaction was performed in the same manner to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.34 (s, 1H), 8.
32 (d, 1H, J = 9.2Hz), 8.22 (d, 1H, J = 6.8Hz), 7.87
(d, 1H, J = 9.2Hz), 7.79-7.68 (m, 3H), 7.46 (d, 2H,
J = 8.9Hz), 7.37 (s, 1H), 6.80 (d, 2H, J = 8.9Hz), 3.6
6 (s, 3H), 2.43 (s, 3H). Example 341 1- [4- [4- (2-methyl-imidazo [1,2-α] quinolin-1-yl)
-Thiazol-2-ylamino] -phenyl] -ethanone hydrobromide Using the compound of Reference Example 57 and (4-acetyl-phenyl) -thiourea (Reference Example 47), a reaction was carried out in the same manner as in Example 157. The title compound was obtained.

1H-NMR (DMSO-d6) δ: 11.01 (s, 1H), 8.
30 (d, 1H, J = 9.2Hz), 8.22 (d, 1H, J = 6.2Hz), 7.87
(d, 1H, J = 9.4Hz), 7.82 (d, 2H, J = 8.9Hz), 7.75-7.64
(m, 5H), 7.57 (s, 1H), 2.54 (s, 3H), 2.44 (s, 3H). (Example 342) [4- (2-Methyl-imidazo [1,2-α] quinoline- 1-yl) -thiazol-2-yl] -p-tolyl-amine hydrobromide Using the compound of Reference Example 57 and p-tolyl-thiourea (purchased from Tokyo Kasei), reacting in the same manner as in Example 157 To give the title compound.

1H-NMR (DMSO-d6) δ: 10.44 (s, 1H), 8.
32 (d, 1H, J = 9.2Hz), 8.22 (d, 1H, J = 7.0Hz), 7.87
(d, 1H, J = 9.2Hz), 7.81-7.65 (m, 3H), 7.43 (d, 2H,
J = 8.6Hz), 7.42 (s, 1H), 7.00 (d, 2H, J = 8.6Hz), 2.4
Example 343 4- [4- (2-Methyl-imidazo [1,2-α] quinolin-1-yl) -thiazol-2-ylamino] 4 (s, 3H), 2.18 (s, 3H). -Ethyl benzoate Ester hydrobromide The compound of Reference Example 57 and 4-thioureido-ethyl benzoate (Reference Example 49) were reacted in the same manner as in Example 157 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.99 (s, 1H), 8.
30-8.27 (m, 1H), 8.22 (d, 1H, J = 6.2Hz), 7.88-7.64
(m, 8H), 7.56 (s, 1H), 4.22 (q, 2H, J = 7.0Hz), 2.44
(s, 3H), 1.26 (t, 3H, J = 7.0 Hz). (Example 344) (6-Methoxy-pyridin-3-yl)-[4- (2-methyl-imidazo
[1,2-α] quinolin-1-yl) -thiazol-2-yl] -amine hydrobromide The compound of Reference Example 57 and (6-methoxy-pyridin-3-
Example 1 using yl) -thiourea (Reference Example 43)
The reaction was carried out in the same manner as in 57 to give the title compound.

1H-NMR (DMSO-d6) δ: 10.49 (s, 1H), 8.3
9 (d, 1H, J = 2.7Hz), 8.31 (d, 1H, J = 8.9Hz), 8.22 (d,
1H, J = 7.6Hz), 7.89-7.84 (m, 2H), 7.77 (d, 2H, J =
2.7Hz), 7.73-7.70 (m, 1H), 7.44 (s, 1H), 6.71 (d,
1H, J = 8.6 Hz), 3.73 (s, 3H), 2.43 (s, 3H). (Example 345) [4- (2-methyl-imidazo [1,2-α] quinolin-1-yl)- Thiazol-2-yl]-(4-trifluoromethyl-phenyl) -amine hydrobromide Using compound of Reference Example 57 and (4-trifluoromethyl-phenyl) -thiourea (Reference Example 2), Example 15
The reaction was carried out in the same manner as in Example 7 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.99 (s, 1H), 8.
28 (d, 1H, J = 8.9Hz), 8.21 (d, 1H, J = 7.3Hz), 7.86
(d, 1H, J = 5.7Hz), 7.76-7.70 (m, 5H), 7.57-7.54 (m,
3H), 2.43 (s, 3H). Example 346 [4- (2-Methyl-imidazo [1,2-α] quinolin-1-yl) -thiazol-2-ylamino] -benzonitrile hydrogen bromide Acid salt Using the compound of Reference Example 57 and (4-cyano-phenyl) -thiourea (Reference Example 48), the reaction was carried out in the same manner as in Example 157 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 11.12 (s, 1H), 8.
28 (d, 1H, J = 9.2Hz), 8.23-8.20 (m, 1H), 7.85 (d, 1
H, J = 9.4 Hz), 7.44-7.59 (m, 8H), 2.43 (s, 3H). (Example 347) (4-Methoxy-phenyl)-[4- (2-methyl-imidazo [1,2 -
α] quinolin-1-yl) -thiazol-2-yl] -amine 2
Hydrochloride (4-methoxy-phenyl)-[4- (2-methyl-imidazo [1,2-
α] quinolin-1-yl) -thiazol-2-yl] -amine (Example 121) (22 mg, 56.5 μmol) was dissolved in a hydrogen chloride-methanol solution, and the solvent was concentrated under reduced pressure.
12.5 mg of the title compound were obtained.

1H-NMR (DMSO-d6) δ: 10.42 (s, 1H), 8.
41 (d, 1H, J = 9.4Hz), 8.26 (d, 1H, J = 7.0Hz), 7.92
(d, 1H, J = 9.4Hz), 7.81-7.80 (m, 1H), 7.76-7.73 (m,
2H), 7.46 (d, 2H, J = 8.9Hz), 7.40 (s, 1H), 6.80 (d,
2H, J = 8.90Hz), 3.66 (s, 3H), 2.46 (s, 3H). (Example 348) [4- (2,6-dimethyl-imidazo [1,2-α] pyridin-3-yl) )
-Thiazol-2-yl]-(6-methoxy-pyridin-3-yl)-
Ethyl carbamic acid ester [4- (2,6-dimethyl-imidazo [1,2-α] pyridin-3-yl)-
Thiazol-2-yl]-(6-methoxy-pyridin-3-yl) -amine hydrobromide (Example 307) was reacted with ethyl chloroformate in the same manner as in Example 301 to give the title compound. Obtained.

Mp 191-192 ° C. (decomp); 1H-NMR (CDCl3) δ 8.43 (br s, 1H), 8.20 (d, 1H, J =
2.7Hz), 7.59 (dd, 1H, J = 2.7Hz, 8.6Hz), 7.38 (d, 1H,
J = 7.4Hz), 7.01 (s, 1H), 6.95 (dd, 1H, J = 1.6Hz, 9.
2Hz), 6.90 (d, 1H, J = 8.6Hz), 4.35 (q, 1H, J = 7.0H
z), 4.01 (s, 3H), 2.59 (s, 3H), 2.13 (s, 3H), 1.29
(t, 1H, J = 7.0 Hz); MS (APCI, m / z): 424 (M + 1) +; HPLC (R): Rt. = 3.5 min. (Example 349) [4- (2, 6-dimethyl-imidazo [1,2-α] pyridin-3-yl)
-Thiazol-2-yl]-(6-methoxy-pyridin-3-yl)-
Carbamic acid benzyl ester [4- (2,6-dimethyl-imidazo [1,2-α] pyridin-3-yl)-
Thiazol-2-yl]-(6-methoxy-pyridin-3-yl) -amine hydrobromide (Example 307) was reacted with benzyl chloroformate in the same manner as in Example 301 to give the title compound. Obtained.

Mp 161-162 ° C .; 1H-NMR (CDCl3) δ 8.41 (brs, 1H), 8.21 (dd, 1H, J =
(0.5Hz, 2.7Hz), 7.58 (dd, 1H, J = 2.7Hz, 8.6Hz), 7.39
-7.26 (m, 6H), 7.00 (s, 1H), 6.94 (dd, 1H, J = 1.6H
z, 8.9Hz), 6.89 (dd, 1H, J = 0.5Hz, 8.6Hz), 5.32 (s,
2H), 4.00 (s, 3H), 2.58 (s, 3H), 2.13 (s, 3H); MS (APCI, m / z): 486 (M + 1) +; HPLC (R): Rt. = 3.7 min. (Example 350) [4- (2,6-dimethyl-imidazo [1,2-α] pyridin-3-yl)
-Thiazol-2-yl] -pyridin-3-yl-amine Using the compound of Reference Example 5 and pyridin-3-yl-thiourea, the reaction was carried out in the same manner as in Example 1 to obtain the title compound. 1H-NMR (DMSO d-6) δ: 10.84 (s, 1H), 8.98 (s, 1H),
8.89 (d, 1H, J = 2.2Hz), 8.24 (dd, 1H, J = 1.6Hz, 4.9H
z), 8.16 (ddd, 1H, J = 1.6Hz, 2.7Hz, 8.4Hz), 7.88
(d, 1H, J = 9.2Hz), 7.80 (dd, 1H, J = 1.6Hz, 9.2Hz),
7.52 (s, 1H), 7.43 (dd, 1H, J = 5.0Hz, 8.4Hz), 2.62
(s, 3H), 2.43 (s, 3H); MS (APCI, m / z): 322 (M + 1) +; HPLC (R): Rt. = 2.2 min. (Example 351) N- [4 -(2,6-Dimethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -N-pyridin-3-yl-acetamide Example 280 using the compound of Example 350 The reaction was carried out in the same manner as in to give the title compound.

1H-NMR (CDCl3) δ: 8.83 (dd, 1H, J = 1.4
Hz, 1.6Hz), 8.75 (d, 1H, J = 1.9Hz), 8.33 (s, 1H),
7.79 (ddd, 1H, J = 1.6Hz, 2.4Hz, 8.1Hz), 7.64 (d, 1
H, J = 9.2Hz), 7.58 (ddd, 1H, J = 0.8Hz, 4.9Hz, 8.1H
z), 7.12 (s, 1H), 7.11 (dd, 1H, J = 1.6Hz, 8.9Hz),
2.62 (s, 3H), 2.17 (s, 6H); MS (APCI, m / z): 364 (M + 1) +; HPLC (R): Rt. = 2.7 min. (Example 352) 5- [ 4- (2,6-dimethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-ylamino] -pyridin-2-ol 2-bromo-1- (2,6-dimethyl-imidazo [1,2-α] pyridine-
Using 100 mg (0.37 mmol) of 3-yl) -ethanone (Reference Example 5) and 70.0 mg (0.41 mmol) of (6-hydroxy-pyridin-3-yl) -thiourea (Reference Example 84), The reaction was carried out in the same manner as in Example 1 to give the title compound 50.
0 mg (40%) was obtained. 1H-NMR (DMSO-d6) δ: 10.01 (s, 1H), 8.81 (s, 1H),
7.93 (d, 1H, J = 2.4Hz), 7.66 (d, 1H, J = 9.5Hz), 7.55
(dd, 1H, J = 3.0Hz, 9.7Hz), 7.48 (d, 1H, J = 9.5Hz),
7.19 (s, 1H), 6.42 (d, 1H, J = 9.5Hz), 2.54 (s, 3H),
2.34 (s, 3H); MS (APCI, m / z): 338 (M + H) +; HPLC (R): Rt = 2.3 min. (Example 353) N- [4- (2,6-dimethyl) -Imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -2,2,2-trifluoro-N- (6-methoxy-pyridin-3-yl) -acetamide [4- (2,6-dimethyl-imidazo [1,2-α] pyridin-3-yl)-
Thiazol-2-yl]-(6-methoxy-pyridin-3-yl) -amine hydrobromide (Example 307) was reacted with trifluoroacetic anhydride in the same manner as in Example 280 to give the title compound. Obtained.

1H-NMR (DMSO-d6) δ: 11.40 (s, 1H), 8.
43 (d, 1H, J = 2.7Hz), 8.04-8.00 (m, 2H), 7.56 (d, 1
H, J = 8.9Hz), 7.30 (d, 1H, J = 8.6Hz), 6.92 (d, 1H, J
= 8.6Hz), 3.85 (s, 3H), 2.36 (s, 3H), 2.30 (s, 3H); MS (APCI, m / z): 448 (M + 1) +; HPLC (R): Rt. = 3.5 min. (Example 354) N- [4- (6-chloro-2-trifluoromethylimidazo [1,2-
α] pyridin-3-yl) -thiazol-2-yl] -N- (4-methoxy-phenyl) -acetamide Using the compound of Example 257, the reaction was carried out in the same manner as in Example 280 to obtain the title compound. mp 204-207 ° C; 1H-NMR (DMSO-d6) δ: 8.66 (dd, 1H, J = 0.8Hz, 1.9H
z), 7.76 (dd, 2H, J = 0.8Hz, 9.5Hz), 7.64 (d, 1H, J =
1.1Hz), 7.56-7.46 (m, 3H), 7.12 (d, 2H, J = 8.9Hz),
3.82 (s, 3H), 2.07 (s, 3H); MS (APCI, m / z): 467 (M + 1) +, 469 (M + 1) +; HPLC (R): Rt. = 6.0 min. (Example 355) N- [4- (6-chloro-2-trifluoromethylimidazo [1,2-
α] pyridin-3-yl) -thiazol-2-yl] -N- (6-methoxy-pyridin-3-yl) -acetamide The title compound was reacted using the compound of Example 256 and in the same manner as in Example 280. I got

Mp 204-206 ° C; 1H-NMR (DMSO-d6) δ: 8.64 (dd, 1H, J = 0.8Hz, 2.2H
z), 8.42 (d, 1H, J = 2.4Hz), 8.04 (dd, 1H, J = 2.7Hz, 8.9
Hz), 7.78 (d, 1H, J = 9.7Hz), 7.68 (d, 1H, J = 0.8Hz),
7.49 (dd, 1H, J = 2.2Hz, 9.7Hz), 7.03 (d, 1H, J = 8.9H
z), 3.91 (s, 3H), 2.10 (s, 3H); MS (APCI, m / z): 468 (M + 1) +, 470 (M + 1) +; HPLC (R): Rt. = 5.5 min. (Example 356) N- (6-methoxy-pyridin-3-yl) -N- [4- (2-trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazole- 2-yl] -acetamide Using the compound of Example 192, the reaction was carried out in the same manner as in Example 280 to obtain the title compound.

Mp 190-193 ° C .; 1H-NMR (DMSO-d6) δ: 8.40 (d, 1H, J = 1.9 Hz), 8.36
(d, 1H, J = 7.0Hz), 8.00 (dd, 1H, J = 2.7Hz, 8.9Hz), 7.7
3 (d, 1H, J = 9.2Hz), 7.67 (s, 1H), 7.48 (dt, 1H, J =
1.1Hz, 6.8Hz), 7.01 (d, 1H, J = 12.7Hz), 3.89 (s, 3
H), 2.09 (s, 3H); MS (APCI, m / z): 434 (M + 1) +; HPLC (R): Rt. = 4.7 min. (Example 357) N [4- (2, 7-Dimethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -N- (6-methoxy-pyridin-3-yl) -acetamide Performed using the compound of Example 67. The reaction was carried out in the same manner as in Example 280 to obtain the title compound.

Mp 160-162 ° C; 1H-NMR (DMSO-d6) δ: 8.40 (dd, 1H, J = 2.4Hz), 8.37
(d, 1H, J = 7.6Hz), 8.01 (dd, 1H, J = 2.7Hz, 8.9Hz), 7.
42 (s, 1H), 7.24 (s, 1H), 7.06 (d, 1H, J = 8.9Hz),
6.53 (dd, 1H, J = 1.9Hz, 7.3Hz), 3.94 (s, 3H), 2.40
(s, 3H), 2.32 (s, 3H), 2.10 (s, 3H); MS (APCI, m / z): 394 (M + 1) +; HPLC (R): Rt. = 3.1 min. Example 358) N- [4- (2,8-dimethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -N- (6-methoxy-pyridin-3-
Yl) -acetamide Using the compound of Example 55, the reaction was carried out in the same manner as in Example 280 to obtain the title compound.

Mp 163-166 ° C .; 1H-NMR (DMSO-d6) δ: 8.40 (dd, 1H, J = 2.2 Hz), 8.34
(d, 1H, J = 7.0Hz), 8.01 (dd, 1H, J = 3.0Hz, 8.9Hz), 7.
46 (s, 1H), 7.05 (d, 1H, J = 8.9Hz), 7.01 (d, 1H, J =
6.8Hz), 3.93 (s, 3H), 2.50 (s, 3H), 2.44 (s, 3H),
2.10 (s, 3H); MS (APCI, m / z): 394 (M + 1) +; HPLC (R): Rt. = 3.1 min. (Example 359) N- (6-methoxy-pyridine-3) -Yl) -N- [4- (2-methylimidazo [2,1-α] isoquinolin-3-yl) -thiazol-2-yl] -acetamide 2-bromo-1- (2-methyl-imidazo [1 , 2-α] isoquinoline-
Compound (6-methoxy) obtained by reacting in the same manner as in Example 1 using (3-yl) -ethanone (Reference Example 16) and (6-methoxy-pyridin-3-yl) -thiourea (Reference Example 43). Pyridin-3-yl)-[4- (2-methyl-imidazo [2,1-α]
Isoquinolin-3-yl) -thiazol-2-yl] -amine was reacted in the same manner as in Example 280 to obtain the title compound.

Mp 272-275 ° C .; ¹ H-NMR (DMSO-d ₆ ) δ: 8.45-8.40 (m, 2H), 8.31 (d, 1
H, J = 7.3Hz), 8.04 (dd, 1H, J = 3.0Hz, J = 8.8Hz), 7.66-
7.57 (m, 2H), 7.54 (s, 1H), 7.10-7.00 (m, 2H), 3.9
5 (s, 3H), 3.31 (s, 3H), 2.11 (s, 3H); MS (APCI, m / z): 430 (M + 1) +; HPLC (R): Rt. = 3.4 min. Example 360) 3- [2- (6-Methoxy-pyridin-3-ylamino) -thiazole
-4-yl] -6-methylimidazo [1,2-α] pyridine-2-carboxylic acid methylamide A compound obtained by hydrolyzing the compound of Example 295 in the same manner as in Example 151 and a 50% aqueous solution of methylamine were used. In the same manner as in Example 235, the title compound was obtained.

Mp 278-280 ° C .; ¹ H-NMR (DMSO-d ₆ ) δ: 10.27 (s, 1H), 8.93 (s, 1H),
8.47 (s, 1H), 8.45-8.40 (br, 1H), 7.99 (d, 1H, J =
8.9Hz), 7.82 (s, 1H), 7.57 (d, 1H, J = 9.7Hz), 7.29
(d, 1H, J = 9.2Hz), 6.84 (d, 1H, J = 8.6Hz), 3.82 (s,
3H), 2.79 (d, 3H, J = 4.9 Hz), 2.31 (s, 3H); MS (APCI, m / z): 395 (M + 1) +; HPLC (R): Rt. = 3.5 min. Example 361 3- [2- [Acetyl- (6-methoxy-pyridin-3-yl) -amino] -thiazol-4-yl] -6-methylimidazo [1,2-α] pyridine-2- Carboxylic acid methylamide Using the compound of Example 360, the reaction was carried out in the same manner as in Example 280 to obtain the title compound.

Mp 220-222 ° C .; ¹ H-NMR (DMSO-d ₆ ) δ: 8.52 (s, 1H), 8.47 (s, 1H),
8.45-8.41 (br, 1H), 8.41 (s, 1H), 8.04 (d, 1H, J =
8.9Hz), 7.50 (d, 1H, J = 9.5Hz), 7.20 (d, 1H, J = 9.5H)
z), 7.06 (d, 1H, J = 8.9Hz), 3.93 (s, 3H), 2.79 (d,
3H, J = 4.6Hz), 2.12 (s, 3H), 2.09 (s, 3H); MS (APCI, m / z): 437 (M + 1) +; HPLC (R): Rt. = 3.9 min. Example 362 [4- (2,6-Dimethyl-imidazo [1,2-α] pyridin-3-yl)
-Thiazol-2-yl]-(6-methylpyridin-3-yl) -amine 2-bromo-1- (2,6-dimethyl-imidazo [1,2-α] pyridine-
Using the compound of Reference Example 85 and 3-yl) -ethanone (Reference Example 5), the reaction was carried out in the same manner as in Example 1 to obtain the title compound.

1H-NMR (DMSOd-6) δ: 10.82 (s, 1H), 8.
96 (s, 1H), 8.81 (d, 1H, J = 2.4Hz), 8.09 (dd, 1H, J = 2.4Hz, 8.4Hz), 7.85 (d, 1H, J = 9.2H)
z), 7.75 (d, 1H, J = 9.5Hz), 7.48 (s, 1H), 7.35 (d,
1H, J = 8.4Hz), 2.62 (s, 3H), 2.47 (s, 3H), 2.43 (s,
3H); MS (APCI, m / z): 336 (M + 1) +; HPLC (R): Rt. = 2.1 min. (Example 363) N- [4- (2-ethyl-imidazo [1, 2-α] pyridin-3-yl)-
Thiazol-2-yl] -N- (6-methoxy-pyridin-3-yl)-
Acetamide Using the compound of Example 174, the reaction was carried out in the same manner as in Example 280 to obtain the title compound.

Mp 151-153 ° C .; 1H-NMR (DMSO-d6) δ: 8.46 (dd, 1H, J = 7.0 Hz), 8.40
(d, 1H, J = 3.0Hz), 8.01 (dd, 1H, J = 2.4Hz, 8.9Hz), 7.
50 (d, 1H, J = 9.7Hz), 7.48 (s, 1H), 7.21 (t, 1H, J =
8.1Hz), 7.04 (d, 1H, J = 8.4Hz), 6.73 (t, 1H, J = 8.1H
z), 3.93 (s, 3H), 2.77 (q, 2H, J = 7.3Hz), 2.10 (s,
3H), 1.16 (t, 3H, J = 7.3 Hz); MS (APCI, m / z): 394 (M + 1) +; HPLC (R): Rt. = Min. (Example 364) N- [ 4- (2,6-dimethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -N-p-tolyl-acetamide Using the compound of Example 59, The same reaction was carried out to obtain the title compound.

Mp 199-200 ° C .; ¹ H-NMR (DMSO-d ₆ ) δ: 8.38 (s, 1H), 7.50-7.34 (m, 6
H), 7.02 (d, 1H, J = 8.9Hz), 2.47 (s, 3H), 2.42 (s,
3H), 2.06 (s, 3H), 2.06 (s, 3H); MS (APCI, m / z): 377 (M + 1) +; HPLC (R): Rt. = 3.7 min. (Example 365) N- [4- (2,6-dimethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -N- (4-trifluoromethylphenyl) -acetamide Using the compound, a reaction was carried out in the same manner as in Example 280 to obtain the title compound. mp 225-228 ° C; ¹ H-NMR (DMSO-d ₆ ) δ: 8.28 (s, 1H), 8.04 (d, 2H, J =
8.6Hz), 7.92 (d, 2H, J = 8.4Hz), 7.44 (s, 1H), 7.36
(d, 1H, J = 8.9Hz), 7.02 (d, 1H, J = 8.9Hz), 2.45 (s,
3H), 2.07 (s, 3H), 2.03 (s, 3H); MS (APCI, m / z): 431 (M + 1) +; HPLC (R): Rt. = 3.8 min. (Example 366) N- (4-Methoxy-phenyl) -N- [4- (6-methyl-2-trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -acetamide Example 261 Using the compound of the above formula, the reaction was carried out in the same manner as in Example 280 to obtain the title compound.

Mp 204-206 ° C; ¹ H-NMR (DMSO-d ₆ ) δ: 8.27 (s, 1H), 7.63-7.53 (m, 4
H), 7.29 (d, 1H, J = 9.2Hz), 7.11 (d, 2H, J = 8.9Hz),
3.81 (s, 3H), 2.19 (s, 3H), 2.06 (s, 3H); MS (APCI,
m / z): 447 (M + 1) +; HPLC (R): Rt. = 5.4 min. (Example 367) N- (4-acetyl-phenyl) -N- [4- (6-methyl2- Trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -acetamide Using the compound of Example 262, the reaction was carried out in the same manner as in Example 280 to obtain the title compound.

Mp 244-247 ° C .; ¹ H-NMR (DMSO-d ₆ ) δ: 8.20-8.15 (m, 3H), 7.84 (d, 2
H, J = 8.6Hz), 7.63-7.58 (m, 2H), 7.28 (d, 1H, J = 9.5H
z), 2.63 (s, 3H), 2.16 (s, 3H), 2.07 (s, 3H); MS (APCI, m / z): 459 (M + 1) +; HPLC (R): Rt. = 4.9 min. (Example 368) N- [4- (6-methyl-2-trifluoromethylimidazo [1,2-
α] pyridin-3-yl) -thiazol-2-yl] -Np-tolyl
-Acetamide Using the compound of Example 263, the reaction was carried out in the same manner as in Example 280 to obtain the title compound. mp 229-232 ° C; ¹ H-NMR (DMSO-d ₆ ) δ: 8.25 (s, 1H), 7.63-7.59 (m, 2
H), 7.51 (d, 2H, J = 8.4Hz), 7.38 (d, 2H, J = 8.6Hz),
7.29 (d, 1H, J = 9.5Hz), 2.38 (s, 3H), 2.18 (s, 3H),
2.06 (s, 3H); MS (APCI, m / z): 431 (M + 1) +; HPLC (R): Rt. = 5.8 min. (Example 369) N- [4- (6-methyl2 -Trifluoromethylimidazo [1,2-
α] pyridin-3-yl) -thiazol-2-yl] -N- (4-trifluoromethylphenyl) -acetamide The compound of Example 264 was reacted in the same manner as in Example 280 to obtain the title compound. .

Mp 223-225 ° C .; ¹ H-NMR (DMSO-d ₆ ) δ: 8.18 (s, 1H), 8.01-7.92 (m, 4
H), 7.65-7.59 (m, 2H), 7.29 (d, 1H, J = 9.2Hz), 2.16
(s, 3H), 2.07 (s, 3H); MS (APCI, m / z): 485 (M + 1) +; HPLC (R): Rt. = 5.8 min. (Example 370) [4- ( 2,6-dimethyl-imidazo [1,2-α] pyridin-3-yl)
-Thiazol-2-yl]-(6-methoxy-pyridin-3-yl)-
Carboxamic acid isopropyl ester The title compound was obtained by carrying out a reaction in the same manner as in Example 301 using the compound of Example 307 and isopropyl chloroformate.

Mp 143-145 ° C .; 1H-NMR (CDCl3) δ 8.43 (br s, 1H), 8.19 (d, 1H, J =
2.4Hz), 7.57 (dd, 1H, J = 2.7Hz, 8.9Hz), 7.37 (d, 1H,
J = 8.9Hz), 7.00 (s, 1H), 6.94 (dd, 1H, J = 1.6Hz, 9.
2Hz), 6.89 (d, 1H, J = 8.6Hz), 5.15 (sep, 1H, J = 6.2H
z), 4.00 (s, 3H), 2.58 (s, 3H), 2.14 (s, 3H), 1.28
(d, 6H, J = 6.2 Hz); MS (APCI, m / z): 438 (M + 1) +; HPLC (R): Rt. = 3.6 min. (Example 371) N- [4- ( 2,6-dimethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -N- (6-methoxy-pyridin-3-yl) -2,2-dimethyl-propionamide Using the compound of Example 307 and trimethylacetic anhydride, the reaction was carried out in the same manner as in Example 280 to obtain the title compound. mp 180-182 ° C; 1H-NMR (CDCl3) δ 8.28 (br s, 1H), 8.25 (dd, 1H, J
= 0.5Hz, 2.7Hz), 7.64 (dd, 1H, J = 2.7Hz, 8.6Hz), 7.3
9 (d, 1H, J = 8.9Hz), 7.00 (s, 1H), 6.94 (dd, 1H, J =
1.6Hz, 9.2Hz), 6.93 (dd, 1H, J = 0.5Hz, 8.6Hz), 4.02
(s, 3H), 2.57 (s, 3H), 2.05 (s, 3H), 1.22 (s, 9
H); MS (APCI, m / z): 436 (M + 1) +; HPLC (R): Rt. = 3.8 min. (Example 372) propane-2-sulfonic acid [4- (2,6- Dimethyl-imidazo
[1,2-α] pyridin-3-yl) -thiazol-2-yl]-(6-methoxy-pyridin-3-yl) -amide Using the compound of Example 307 and isopropylsulfonyl chloride, The same reaction was performed to obtain the title compound.

Mp 157-158 ° C; 1H-NMR (CDCl3) δ 8.78 (br s, 1H), 8.35 (dd, 1H, J
= 0.5Hz, 2.7Hz), 7.73 (dd, 1H, J = 2.7Hz, 8.9Hz), 7.4
6 (d, 1H, J = 9.2Hz), 7.06 (dd, 1H, J = 1.6Hz, 9.2Hz),
6.90 (s, 1H), 6.89 (dd, 1H, J = 0.8Hz, 8.9Hz), 4.39
(sep, 1H, J = 7.0Hz), 4.00 (s, 3H), 2.60 (s, 3H),
2.33 (s, 3H), 1.53 (d, 6H, J = 7.0Hz); MS (APCI, m / z): 458 (M + 1) +; HPLC (R): Rt. = 3.5 min. (Example 373) [4- (2,6-Dimethyl-imidazo [1,2-α] pyridin-3-yl)
-Thiazol-2-yl]-(6-methoxy-pyridin-3-yl)-
Methylamine Example 3 using the compound of Example 307 and methyl iodide
The reaction was carried out in the same manner as in Example 01 to obtain the title compound. 1H-NMR (CDCl3) δ 8.77 (br s, 1H), 8.29 (d, 1H, J =
2.7Hz), 7.69 (dd, 1H, J = 2.7Hz, 8.6Hz), 7.44 (d, 1
H, J = 9.2Hz), 7.02 (dd, 1H, J = 1.9Hz, 9.2Hz), 6.85
(d, 1H, J = 8.6Hz), 6.54 (s, 1H), 3.98 (s, 3H), 3.57
(s, 3H), 2.59 (s, 3H), 2.32 (s, 3H); MS (APCI, m / z): 366 (M + 1) +; HPLC (R): Rt. = 3.4 min. Example 374) N- [4- (2,6-dimethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -N- (6-hydroxy-pyridin-3-
(Il) -acetamide Using 10 mg (0.03 mmol) of the compound of Example 352, the reaction was carried out in the same manner as in Example 126 to obtain 4.8 mg (43%) of the title compound.

1H-NMR (DMSO-d6) δ: 8.65 (s, 1H), 7.8
0 (d, 1H, J = 2.4Hz), 7.74 (dd, 1H, J = 3.0Hz, 9.7Hz),
7.35 (d, 1H, J = 9.2Hz), 7.32 (s, 1H), 7.13 (dd, 1H,
J = 1.6Hz, 9.5Hz), 6.73 (d, 1H, J = 9.5Hz), 2.52 (s,
3H), 2.26 (s, 3H), 2.24 (s, 3H); MS (APCI, m / z): 380 (M + H) +; HPLC (R): Rt = 2.4 min. (Example 375) N -[4- (2,6-Dimethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -N- (6-methylpyridin-3-yl)
-Acetamide Using the compound of Example 362, the reaction was carried out in the same manner as in Example 280 to obtain the title compound.

1H-NMR (DMSOd-6) δ: 8.69 (d, 1H, J = 2.
4Hz), 8.32 (s, 1H), 8.00 (dd, 1H, J = 2.4Hz, 8.4Hz),
7.53 (d, 1H, J = 8.4Hz), 7.42 (s, 1H), 7.36 (d, 1H,
J = 9.2Hz), 7.04 (d, 1H, J = 9.2Hz), 2.58 (s, 3H), 2.54
(s, 3H), 2.10 (s, 3H), 2.08 (s, 3H); MS (APCI, m / z): 336 (M-41) +; HPLC (R): Rt. = 2.2 min. Example 376) 4-[[[4- (2,6-dimethyl-imidazo [1,2-α] pyridine-3-
Yl) -thiazol-2-yl]-(6-methoxy-pyridin-3-yl) -amino] -methyl] -5-methyl [1,3] dioxol-2-
The same reaction as in Example 132 was carried out using on 4-bromomethyl-5-methyl- [1,3] dioxol-2-one and the compound of Example 61 to give the title compound. 1H-NMR (DMSO-d6) δ: 8.77 (s, 1H), 8.39 (d, 1H, J =
3.0Hz), 7.95 (dd, 1H, J = 3.0Hz, 8.9Hz), 7.43 (d, 1
H, J = 8.9Hz), 7.13 (dd, 1H, J = 1.6Hz, 9.2Hz), 7.00
(d, 1H, J = 8.9Hz), 6.96 (s, 1H), 5.00 (s, 2H), 3.92
(s, 3H), 2.47 (q, 2H, J = 7.3Hz), 2.32 (s, 3H), 1.92
(s, 3H); MS (APCI, m / z): 464 (M + 1) +; HPLC (R): Rt. = 3.6 min. (Example 377) 4-[[[4- (2,6 -Dimethyl-imidazo [1,2-α] pyridine-3-
Yl) -thiazol-2-yl]-(6-methoxy-pyridin-3-yl) -amino] -methyl] -5-methyl [1,3] dioxol-2-
On monohydrochloride The title compound was obtained by carrying out a reaction in the same manner as in Example 269 using the compound of Example 376.

Mp 230-237 ° C. (dec.); 1H-NMR (DMSO-d6) δ: 9.01 (s, 1H), 8.90 (d, 1H, J =
2.7Hz), 7.94 (dd, 1H, J = 2.4Hz, 8.6Hz), 7.88 (d, 1H,
J = 9.5Hz), 7.80 (d, 1H, J = 9.2Hz), 7.33 (s, 1H), 7.0
2 (d, 1H, J = 8.9Hz), 4.99 (s, 2H), 3.92 (s, 3H), 2.
60 (q, 2H, J = 7.3Hz), 2.46 (s, 3H), 1.91 (s, 3H); MS (APCI, m / z): 464 (M + 1) +; HPLC (R): Rt. (Example 378) 2-amino-N- [4- (2,6-dimethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -N- ( 6-methoxy-pyridin-3-yl) -acetamide trihydrochloride 1) [4- (2,6-dimethyl-imidazo [1,2-
α] pyridin-3-yl) -thiazol-2-yl]-(6-methoxy
-Pyridin-3-yl) -amine hydrobromide (Example 30)
7) To a solution of 500 mg (1.16 mmol) and 244 mg (1.39 mmol) of N- (tert-butoxycarbonyl) glycine in 10 ml of N, N-dimethylacetamide, 2 ml of triethylamine was added. O-azabenzotriazol-1-yl-N, N, N ', N-tetramethylonium hexafluorophosphate (hereinafter abbreviated as HATU) 6
60 mg (1.73 mmol) was added, and the mixture was stirred at room temperature for 15 hours. Ethyl acetate was added to the reaction solution, and the mixture was washed with a saturated aqueous solution of sodium hydrogen carbonate and saturated saline. After the organic layer was dried over anhydrous sodium sulfate, the solvent was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (dichloromethane: methanol = 10: 1), and [[[4- (2,6-dimethyl-
620 mg of imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl]-(6-methoxy-pyridin-3-yl) -carbamoyl] -methyl] -carbamic acid tert-butyl ester were obtained. .

2) Example 378 The compound (620 mg) obtained in 1) was dissolved in ethanol (10 ml), 4N dioxane-hydrochloric acid (6 ml) was added, and the mixture was stirred at room temperature for 4 hours. The reaction solution was concentrated under reduced pressure, ethyl acetate was added to the obtained residue, and the crystals were filtered to obtain 524 mg of the title compound (yield: 8
2%, two steps). mp 228-230 ° C; 1H-NMR (DMSO-d6) δ: 8.62 (s, 1H), 8.51 (d, 1H, J =
2.7Hz), 8.52-8.51 (m, 2H), 8.08 (dd, 1H, J = 2.7Hz,
8.6Hz), 7.94 (s, 1H), 7.84 (d, 1H, J = 9.5Hz), 7.75
(d, 1H, J = 8.9Hz), 7.10 (d, 1H, J = 8.9Hz), 3.93 (s,
3H), 3.85-3.71 (m, 2H), 2.58 (s, 3H), 2.28 (s, 3
H); MS (APCI, m / z): 409 (M + 1) +; HPLC (R): Rt. = 2.1 min. (Example 379) 2-amino-N- [4- (2,6- Dimethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -N- (6-methoxy-pyridin-3-yl) -propionamide trihydrochloride N- (tert-butoxycarbonyl ) Using -L-alanine and the compound of Example 307, the reaction was carried out in the same manner as in Example 378 to obtain the title compound.

Mp 223-226 ° C. (dec.); 1H-NMR (DMSO-d6) δ: 8.70 (brs, 3H), 8.60 (s, 1H),
8.30-8.10 (m, 1H), 7.97 (s, 1H), 7.85 (d, 1H, J =
8.9Hz), 7.77 (d, 1H, J = 8.6Hz), 7.12 (d, 1H, J = 9.2H
z), 4.10-3.95 (m, 1H), 3.95 (s, 3H), 2.59 (s, 3H),
2.30 (s, 3H), 1.35 (brs, 3H); MS (APCI, m / z): 423 (M + 1) +; HPLC (R): Rt. = 2.2 min. (Example 380) [3- (3- [2- [acetyl- (6-methoxy-pyridin-3-yl) -amino] -thiazol-4-yl] -2-methylimidazo [1,2-α]
Using pyridine-6-ylcarbamoyl) -propyl] -carbamic acid tert-butyl ester N- (tert-butoxycarbonylamino) butanoic acid and the compound of Example 298, the reaction was carried out in the same manner as in Example 382 to obtain the title compound. Was.

1H-NMR (CDCl ₃ ) δ: 9.55 (brs, 1H), 9.4
8 (brs, 1H), 8.19 (d, 1H, J = 2.7Hz), 7.82 (dd, 1H,
J = 3.0Hz, 8.6Hz), 7.67 (d, 1H, J = 9.2Hz), 7.31 (d, 1
H, J = 1.9Hz), 7.15 (s, 1H), 6.83 (d, 1H, J = 8.6Hz),
4.95 (brs, 1H), 3.95 (s, 3H), 3.32-3.28 (m, 2H),
3.21-3.17 (m, 2H), 2.16 (s, 3H), 2.10 (s, 3H), 1.9
2-1.88 (m, 2H), 1.48 (s, 9H) ,; MS (APCI, m / z): 580 (M + 1) +; HPLC (R): Rt. = 3.5 min. (Example 381) N- [4- (2,6-dimethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -2-methoxy-N- (6-methoxy-
Pyridin-3-yl) -acetamide [4- (2,6-dimethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl]-(6-methoxy-pyridine) under a nitrogen stream
315 mg (1.47 mmol) of N-3-N) -amine
-Dissolved in 10 ml of dimethylacetamide, added 478 mg (4.40 mmol) of methoxyacetyl chloride,
Stirred at 70 ° C. for 5 hours. Ethyl acetate was added to the reaction solution,
The extract was washed with a saturated aqueous solution of sodium hydrogen carbonate and a saturated saline solution. After the organic layer was dried over anhydrous sodium sulfate, the solvent was concentrated under reduced pressure, and the obtained crystals were finely pulverized.
Washing with ethyl acetate gave 478 mg (77%) of the title compound.

Mp 182-184 ° C .; 1H-NMR (CDCl3) δ 8.38 (br s, 1H), 8.26 (dd, 1H, J
= 0.5Hz, 2.7Hz), 7.65 (dd, 1H, J = 2.7Hz, 8.9Hz), 7.4
1 (d, 1H, J = 8.9Hz), 7.07 (s, 1H), 6.97 (d, 2H, J =
8.9Hz), 4.05 (s, 2H), 4.03 (s, 3H), 3.47 (s, 3H),
2.59 (s, 3H), 2.13 (s, 3H); MS (APCI, m / z): 424 (M + 1) +; HPLC (R): Rt. = 2.9 min. (Example 382) Acetic acid [[ 4- (2,6-dimethyl-imidazo [1,2-α] pyridine-3
-Yl) -thiazol-2-yl]-(6-methoxy-pyridine-3-
Yl) -carbamoyl] -methyl ester [4- (2,6-dimethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl]-(6-methoxy-pyridine) under a nitrogen stream -3-yl) -amine hydrobromide (Example 307)
00g (2.31 mmol) and 410 mg of acetoxyacetic acid
(3.47 mmol) in N, N-dimethylacetamide 2
To the solution dissolved in 0 ml, 4 ml of triethylamine was added. 1.32 g (3.47 mmol) of HATU was added and the mixture was stirred at room temperature for 15 hours. Ethyl acetate was added to the reaction solution, and the mixture was washed with a saturated aqueous solution of sodium hydrogen carbonate and saturated saline. After the organic layer was dried over anhydrous sodium sulfate, the solvent was concentrated under reduced pressure.
The residue was purified by silica gel column chromatography (dichloromethane: methanol = 10: 1), and the obtained crystals were finely ground and washed with hexane-ethyl acetate to obtain 1.12 g of the title compound.

Mp 110-112 ° C .; 1H-NMR (CDCl ₃ ) δ: 8.37 (s, 1H), 8.32 (d, 1H, J = 2.
7Hz), 7.70 (dd, 1H, J = 3.0Hz, 8.9Hz), 7.43 (d, 1H,
J = 8.6Hz), 7.08 (s, 1H), 7.00 (t, 1H, J = 1.6Hz), 6.9
6 (d, 1H, J = 3.2Hz), 4.62 (brs, 2H), 4.02 (s, 3H),
2.59 (s, 3H), 2.22 (s, 3H), 2.14 (s, 3H); MS (APCI, m / z): 452 (M + 1) +; HPLC (R): Rt. = 3.2 min. Example 383) (3- [3- [2- (6-Methoxy-pyridin-3-ylamino) -thiazol-4-yl] -2-methylimidazo [1,2-α] pyridin-6-
Ilcarbamoyl] -propyl) -carbamic acid tert-butyl ester Using the compound of Example 380, the reaction was carried out in the same manner as in Example 151 to obtain the title compound. 1H-NMR (CDCl ₃ + D ₂ O) δ: 9.90 (s, 1H), 8.25 (d, 1H,
J = 2.7Hz), 7.76 (d, 1H, J = 11.1Hz), 7.51 (d, 1H, J = 9.2Hz), 7.11 (d, 1H, J = 1
0.5Hz), 6.75 (d, 1H, J = 8.4Hz), 6.60 (s, 1H), 3.94
(s, 3H), 3.29-3.21 (m, 2H), 2.59 (s, 3H), 2.42-2.4
0 (m, 2H), 1.95-1.81 (m, 2H), 1.47 (s, 9H); MS (APCI, m / z): 538 (M + 1) +; HPLC (R): Rt. = 3.4 min Example 384 N- [4- (2,6-dimethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -N- (6-methoxy-pyridin-3 -Yl) -Succinamic acid allyl ester succinic acid monoallyl ester and Example 307
Using the compound of the above formula, the reaction was carried out in the same manner as in Example 382 to obtain the title compound.

1H-NMR (CDCl ₃ ) δ: 8.40 (s, 1H), 8.28
(d, 1H, J = 2.4Hz), 7.68 (dd, 1H, J = 2.7Hz, 8.6Hz), 7.
39 (d, 1H, J = 8.9Hz), 7.04 (s, 1H), 6.96 (d, 2H, J =
8.9Hz), 5.97-5.84 (m, 1H), 5.33 (d, 1H, J = 17.6Hz),
5.24 (d, 1H, J = 10.3Hz), 4.60 (d, 2H, J = 5.4Hz), 4.0
2 (s, 3H), 2.80-2.78 (m, 2H), 2.65-2.59 (m, 2H), 2.59 (s, 3H), 2.14 (s, 3H); MS (APCI, m / z): 492 ( M + 1) +; HPLC (R): Rt. = 3.6 min. (Example 385) [4- (6-Chloro-2-methylimidazo [1,2-α] pyridine-3-
Yl) -thiazol-2-yl]-(6-methoxy-pyridin-3-yl) -carbamic acid isobutyl ester The compound of Example 84 was reacted in the same manner as in Example 301 to obtain the title compound.

Mp 150-153 ° C; 1H-NMR (DMSO-d6) δ: 8.72 (dd, 1H, J = 1.1Hz, 2.4H
z), 8.34 (d, 1H, J = 2.7Hz), 7.96 (dt, 1H, J = 1.4Hz,
8.6Hz), 7.52 (d, 1H, J = 9.5Hz), 7.53 (s, 1H), 7.22
(dt, 1H, J = 1.1Hz, 8.6Hz), 7.01 (d, 1H, J = 8.9Hz),
4.03 (d, 2H, J = 6.2Hz), 3.91 (s, 3H), 2.51 (s, 3H),
1.88-1.81 (m, 1H), 0.79 (d, 6H, J = 6.8Hz); MS (APCI, m / z): 472 (M + 1) +, 474 (M + 1) +; HPLC (R) : Rt. = 4.4 min. (Example 386) [4- (2,8-dimethyl-imidazo [1,2-α] pyridin-3-yl)
-Thiazol-2-yl]-(6-methoxy-pyridin-3-yl)-
Carbamate isobutyl ester The compound of Example 55 was used and reacted in the same manner as in Example 301 to obtain the title compound. mp 163-164 ° C; 1H-NMR (DMSO-d6) δ: 8.36 (d, 1H, J = 7.0Hz), 8.33
(d, 1H, J = 2.4Hz), 7.94 (dd, 1H, J = 2.7Hz, 8.9Hz), 7.
45 (s, 1H), 7.02 (d, 1H, J = 8.6Hz), 6.98 (d, 1H, J =
8.6Hz), 6.62 (t, 1H, J = 6.8Hz), 4.02 (d, 2H, J = 6.5H
z), 3.90 (s, 3H), 2.50 (s, 3H), 2.44 (s, 3H), 1.90
-1.80 (m, 1H), 0.79 (d, 6H, J = 6.8Hz); MS (APCI, m / z): 452 (M + 1) +; HPLC (R): Rt. = 3.8 min. Example 387) [4- (6-Chloro-2-methylimidazo [1,2-α] pyridine-3-
Yl) -thiazol-2-yl]-(6-chloro-pyridin-3-yl) -amine monohydrobromide Compound of Reference Example 12 and (6-chloro-pyridin-3-yl) -thiourea (reference Using Example 46), a reaction was carried out in the same manner as in Example 157 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.92 (s, 1H), 9.
26 (s, 1H), 8.70 (d, 1H, J = 2.7Hz), 8.14 (dd, 1H, J =
3.0Hz, 8.9Hz), 7.93 (d, 1H, J = 8.9Hz), 7.86 (d, 1H,
J = 8.9Hz), 7.52 (s, 1H), 7.47 (d, 1H, J = 8.9Hz), 2.
63 (s, 3H); MS (APCI, m / z): 376 (M + 1) +, 378 (M + 1) +; HPLC (R): Rt. = 3.3 min. (Example 388) -Chloro-pyridin-3-yl)-[4- (2,8-dimethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -amine monohydrobromide Using the compound of Example 1 and (6-chloro-pyridin-3-yl) -thiourea (Reference Example 46), the reaction was carried out in the same manner as in Example 157 to obtain the title compound. 1H-NMR (DMSO-d6) δ: 10.94 (s, 1H), 8.91 (d, 1H, J
= 6.8Hz), 8.72 (d, 1H, J = 2.4Hz), 8.11 (dd, 1H, J = 3.0
Hz, 8.9Hz), 7.78 (d, 1H, J = 8.4Hz), 7.56 (s, 1H), 7.47 (d, 1H, J = 8.9Hz), 7.43 (d, 1H, J = 7.0Hz),
2.65 (s, 3H), 2.62 (s, 3H); MS (APCI, m / z): 356 (M + 1) +, 358 (M + 1) +; HPLC (R): Rt. = 3.0 min. Example 389 (6-Methoxy-pyridin-3-yl)-[4- (6-methyl-2-trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -Carbamic acid isobutyl ester The compound of Example 265 was reacted in the same manner as in Example 301 to obtain the title compound.

Mp 148-149 ° C .; ¹ H-NMR (DMSO-d ₆ ) δ: 8.40 (s, 1H), 8.28 (s, 1H),
7.99 (d, 1H, J = 8.6Hz), 7.64-7.60 (m, 2H), 7.31 (d,
1H, J = 9.2Hz), 6.96 (d, 1H, J = 8.6Hz), 4.03 (d, 2H,
J = 6.5Hz), 3.88 (s, 3H), 2.23 (s, 3H), 1.85 (sep,
1H, J = 6.2Hz), 0.79 (d, 6H, J = 6.8Hz); MS (APCI, m / z): 506 (M + 1) +; HPLC (R): Rt. = 6.8 min. Example 390) [4- (6-Chloro-2-methylimidazo [1,2-α] pyridine-3-
Yl) -thiazol-2-yl]-(6-chloro-pyridin-3-yl) -carbamic acid isobutyl ester Using the compound of Example 387, the reaction was carried out in the same manner as in Example 301 to obtain the title compound. mp 154-156 ° C; 1H-NMR (DMSO-d6) δ: 8.67 (d, 1H, J = 2.7Hz), 8.66
(d, 1H, J = 3.5Hz), 8.22 (dd, 1H, J = 2.7Hz, 8.4Hz), 7.
78 (d, 1H, J = 8.4Hz), 7.55 (s, 1H), 7.53 (d, 1H, J = 1
0.3Hz), 7.24 (dd, 1H, J = 1.9Hz, 9.5Hz), 4.03 (d, 2
(H, J = 6.2Hz), 2.51 (s, 3H), 1.88-1.83 (m, 1H), 0.78
(d, 1H, J = 6.5Hz); MS (APCI, m / z): 476 (M + 1) +, 478 (M + 1) +; HPLC (R): Rt. = 4.3 min. 391) (6-Chloro-pyridin-3-yl)-[4- (2,8-dimethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -carbamic acid isobutyl ester The title compound was obtained by carrying out a reaction in the same manner as in Example 301 using the compound of Example 388.

Mp 188-191 ° C .; 1H-NMR (DMSO-d6) δ: 8.66 (d, 1H, J = 2.7 Hz), 8.29
(d, 1H, J = 2.7Hz, 8.6Hz), 7.19
75 (d, 1H, J = 8.6Hz), 7.51 (s, 1H), 7.03 (d, 1H, J =
6.8Hz), 6.63 (t, 1H, J = 8.6Hz), 4.03 (d, 2H, J = 6.2H)
z), 2.45 (s, 3H), 2.43 (s, 3H), 1.88-1.83 (m, 1H),
0.78 (d, 1H, J = 6.5Hz); MS (APCI, m / z): 456 (M + 1) +, 458 (M + 1) +; HPLC (R): Rt. = 3.8 min. Example 392) N- [4- (6-chloro-2-methylimidazo [1,2-α] pyridine-3
-Yl) -thiazol-2-yl] -N- (6-chloro-pyridine-3-
Yl) -acetamide The compound of Example 387 was reacted in the same manner as in Example 280 to obtain the title compound. mp 259-262 ° C; 1H-NMR (DMSO-d6) δ: 8.73 (d, 1H, J = 1.9Hz), 8.64
(dd, 1H, J = 0.8Hz, 2.2Hz), 8.26 (dd, 1H, J = 2.4Hz,
8.4Hz), 7.84 (d, 1H, J = 8.6Hz), 7.54 (s, 1H), 7.53
(dd, 1H, J = 0.8Hz, 8.4Hz), 7.24 (dd, 1H, J = 1.9Hz,
9.5 Hz), 2.50 (s, 3H), 2.11 (s, 3H); MS (APCI, m / z): 418 (M + 1) +, 420 (M + 1) +; HPLC (R): Rt. = 3.4 min. (Example 393) N- (6-chloro-pyridin-3-yl) -N- [4- (2,8-dimethyl-imidazo [1,2-α] pyridin-3-yl)- Thiazol-2-yl]
-Acetamide The title compound was obtained by carrying out a reaction in the same manner as in Example 280 using the compound of Example 388.

Mp 187-190 ° C .; 1H-NMR (DMSO-d6) δ: 8.72 (d, 1H, J = 2.7 Hz), 8.27
(d, 1H, J = 7.6Hz), 8.23 (dd, 1H, J = 2.7Hz, 8.4Hz), 7.
82 (d, 1H, J = 8.6Hz), 7.49 (s, 1H), 7.03 (d, 1H, J =
6.8Hz), 6.62 (t, 1H, J = 7.0Hz), 2.45 (s, 3H), 2.43
(s, 3H), 2.11 (s, 3H); MS (APCI, m / z): 398 (M + 1) +, 400 (M + 1) +; HPLC (R): Rt. = 3.1 min. Example 394) (6-Chloro-pyridin-3-yl)-[4- (6-methyl-2-trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl]- Amine The reaction was carried out in the same manner as in Example 157 using the compound of Reference Example 73 and (6-chloro-pyridin-3-yl) -thiourea (Reference Example 46) to obtain the title compound. ¹ H-NMR (DMSO-d ₆ ) δ: 10.90 (s, 1H), 8.68 (s, 1H),
8.45 (s, 1H), 8.20 (d, 1H, J = 8.9Hz), 7.71 (d, 1H,
J = 9.2Hz), 7.48-7.38 (m, 3H), 2.34 (s, 3H); MS (APC
I, m / z): 410 (M + 1) +; HPLC (R): Rt. = 5.2 min. (Example 395) (6-chloro-pyridin-3-yl)-[4- (2,6 -Dimethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -amine monohydrobromide Compound of Reference Example 5 and (6-chloro-pyridin-3-yl)- The reaction was carried out in the same manner as in Example 157 using thiourea (Reference Example 46) to obtain the title compound.

1H-NMR (DMSO-d6) δ: 8.95 (br s, 1H),
8.73 (d, 1H, J = 2.7Hz), 8.15 (dd, 1H, J = 2.7Hz, 8.9H
z), 7.93-7.83 (m, 2H), 7.57 (s, 1H), 7.49 (d, 1H,
J = 8.6Hz), 2.63 (s, 3H), 2.52 (s, 3H), 2.44 (s, 3H); MS (APCI, m / z): 356 (M + 1) +, 358 (M + 1) +; HPLC (R): Rt. = 3.1 min. (Example 396) Acetic acid [[4- (2,8-dimethyl-imidazo [1,2-α] pyridine-3)
-Yl) -thiazol-2-yl]-(6-methoxy-pyridine-3-
Yl) -carbamoyl] -methyl ester The same procedure as in Example 382 was carried out using the compound of Example 55 to give the title compound. mp 172-175 ° C; 1H-NMR (DMSO-d6) δ: 8.46 (d, 1H, J = 2.7Hz), 8.33
(d, 1H, J = 6.8Hz), 8.05 (dd, 1H, J = 2.7Hz, 8.6Hz), 7.
53 (s, 1H), 7.08 (d, 1H, J = 6.8Hz), 7.02 (d, 1H, J =
7.0Hz), 6.61 (t, 1H, J = 7.0Hz), 4.66 (s, 2H), 3.94
(s, 3H), 2.44 (s, 6H), 2.13 (s, 3H); MS (APCI, m / z): 452 (M + 1) +; HPLC (R): Rt. = 3.1 min. Example 397) N- [4- (2,8-dimethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -2-methoxy-N- (6-methoxy-pyridin- 3-yl) -acetamide Example 3 using the compound of Example 55 and methoxyacetic acid
The title compound was obtained by reacting in the same manner as in 82.

Mp 197-200 ° C .; 1H-NMR (DMSO-d6) δ: 8.42 (d, 1H, J = 2.7 Hz), 8.33
(d, 1H, J = 7.3Hz), 8.03 (dd, 1H, J = 2.2Hz, 8.9Hz), 7.
50 (s, 1H), 7.05 (d, 1H, J = 8.6Hz), 7.01 (d, 1H, J =
8.1Hz), 6.60 (t, 1H, J = 6.8Hz), 4.06 (brs, 2H), 3.9
3 (s, 3H), 3.32 (s, 6H), 2.44 (s, 3H); MS (APCI, m / z): 424 (M + 1) +; HPLC (R): Rt. = 3.1 min. Example 398) N- [4- (6-Chloro-2-methylimidazo [1,2-α] pyridine-3
-Yl) -thiazol-2-yl] -2-methoxy-N- (6-methoxy
-Pyridin-3-yl) -acetamide dihydrochloride Example 3 using the compound of Example 84 and methoxyacetic acid
The title compound was obtained by reacting in the same manner as in 82. 1H-NMR (DMSO-d6) δ: 8.96 (s, 1H), 8.46 (d, 1H, J =
2.2Hz), 8.07 (dd, 1H, J = 2.4Hz, 8.6Hz), 7.95-7.86 (m,
3H), 7.07 (d, 1H, J = 8.9Hz), 4.08 (brs, 2H), 3.93
(s, 3H), 3.33 (s, 6H), 2.50 (s, 3H); MS (APCI, m / z): 444 (M + 1) +, 446 (M + 1) +; HPLC (R): Rt. = 3.2 min. (Example 399) [[4- (6-Chloro-2-methylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl]-(6-methoxyacetic acid) -Pyridine
-3-yl) -carbamoyl] -methyl ester The compound of Example 84 was reacted in the same manner as in Example 382 to obtain the title compound.

Mp 133-136 ° C .; 1H-NMR (DMSO-d6) δ: 8.80 (s, 1H), 8.48 (d, 1H, J =
2.7Hz), 8.08 (dd, 1H, J = 3.0Hz, 8.9Hz), 7.71 (s, 1
H), 7.68 (d, 1H, J = 8.9Hz), 7.48 (d, 1H, J = 9.7Hz),
7.10 (d, 1H, J = 8.9Hz), 4.66 (brs, 2H), 3.94 (s, 3
H), 2.56 (s, 6H), 2.14 (s, 3H); MS (APCI, m / z): 472 (M + 1) +, 474 (M + 1) +; HPLC (R): Rt. = 3.4 min. (Example 400) [[[4- (6-Chloro-2-methylimidazo [1,2-α] pyridine-3]
-Yl) -thiazol-2-yl]-(6-methoxy-pyridine-3-
Yl) -Carbamoyl] -methyl] -carbamic acid tert-butyl ester The compound of Example 84 was reacted in the same manner as in Example 378 1) to give the title compound. 1H-NMR (DMSO-d6) δ: 8.71 (d, 1H, J = 1.6Hz), 8.43
(d, 1H, J = 2.4Hz), 8.02 (dd, 1H, J = 3.0Hz, 8.9Hz),
7.54 (s, 1H), 7.52 (d, 1H, J = 9.7Hz), 7.25-7.21 (m, 2H), 7.09 (d, 1H, J = 8.9Hz), 3.94 (s, 3H), 3.74
(brs, 2H), 2.69 (s, 3H), 1.40 (s, 9H); MS (APCI, m / z): 529 (M + 1) +, 531 (M + 1) +; HPLC (R): Rt. = 3.8 min. (Example 401) 2-amino-N- [4- (2,8-dimethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -N -(6-Methoxy-pyridin-3-yl) -acetamide trihydrochloride The compound of Example 55 was reacted in the same manner as in Example 378 to obtain the title compound.

Mp 219-222 ° C. (dec.); 1H-NMR (DMSO-d6) δ: 8.59 (d, 1H, J = 6.8 Hz), 8.52
(brs, 2H), 8.47 (d, 1H, J = 2.2Hz), 8.06 (dd, 1H, J =
3.0Hz, 8.6Hz), 7.98 (s, 1H), 7.73 (d, 1H, J = 7.3H
z), 7.28 (t, 1H, J = 6.8Hz), 7.10 (d, 1H, J = 9.4Hz),
3.93 (s, 3H), 3.81 (s, 3H), 2.60 (s, 6H), 2.59 (s,
3H); MS (APCI, m / z): 409 (M + 1) +; HPLC (R): Rt. = 2.1 min. (Example 402) 2-amino-N- [4- (6-chloro- 2-methylimidazo [1,2-α]
Pyridin-3-yl) -thiazol-2-yl] -N- (6-methoxy
-Pyridin-3-yl) -acetamide trihydrochloride The compound of Example 400 was reacted in the same manner as in Example 378 2) to give the title compound. mp 226-230 ° C (dec.); 1H-NMR (DMSO-d6) δ: 8.94 (s, 1H), 8.54 (brs, 2H),
8.49 (d, 1H, J = 2.4Hz), 8.08 (dd, 1H, J = 2.7Hz, 8.9
Hz), 7.95 (s, 1H), 7.95-7.89 (m, 2H), 7.13 (d, 1H,
J = 8.9Hz), 3.95 (s, 3H), 3.83 (s, 3H), 2.64 (s, 6
H); MS (APCI, m / z): 429 (M + 1) +, 431 (M + 1) +; HPLC (R): Rt. = 2.3 min. (Example 403) N- (6-chloro) -Pyridin-3-yl) -N- [4- (6-methyl-2-trifluoromethylimidazo [1,2-α] pyridin-3-yl)-
Thiazol-2-yl] -acetamide Using the compound of Example 394, the reaction was carried out in the same manner as in Example 280 to obtain the title compound.

Mp 246-248 ° C .; ¹ H-NMR (DMSO-d ₆ ) δ: 8.78 (s, 1H), 8.26 (d, 1H, J =
8.4Hz), 8.20 (s, 1H), 7.79 (d, 1H, J = 8.6Hz), 7.67
(s, 1H), 7.63 (d, 1H, J = 8.9Hz), 7.32 (d, 1H, J = 9.2H
z), 2.24 (s, 3H), 2.11 (s, 3H); MS (APCI, m / z): 452 (M + 1) +, 454 (M + 1) +; HPLC (R): Rt. = 4.9 min. (Example 404) (6-Chloro-pyridin-3-yl)-[4- (6-methyl-2-trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazol-2 -Yl] -carbamic acid isobutyl ester The title compound was obtained by carrying out a reaction in the same manner as in Example 301 using the compound of Example 394. mp 160-163 ° C; ¹ H-NMR (DMSO-d ₆ ) δ: 8.73 (s, 1H), 8.72-8.20 (m, 2
H), 7.73 (d, 1H, J = 8.4Hz), 7.68 (s, 1H), 7.63 (d,
1H, J = 10.0Hz), 7.32 (d, 1H, J = 8.1Hz), 4.04 (d, 2H,
J = 6.5Hz), 2.24 (s, 3H), 1.85 (sep, 1H, J = 6.8Hz),
0.783 (d, 6H, J = 6.8Hz); MS (APCI, m / z): 510 (M + 1) +, 512 (M + 1) +; HPLC (R): Rt. = 6.3 min. Example 405) 2-amino-N- (6-methoxy-pyridin-3-yl) -N- [4- (6-
Methyl 2-trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -acetamide (6-methoxy-pyridin-3-yl)-[4- (6 -Methyl-2-trifluoromethyl-imidazo [1,2-α] pyridine
-3-yl) -thiazol-2-yl] -amine (Example 265)
To 900 mg (2.22 mmol) and 583 mg (3.33 mmol) of N- (tert-butoxycarbonyl) glycine dissolved in 25 ml of N, N-dimethylacetamide were added 3 ml of triethylamine. HATU 1.27
g (3.33 mmol) was added and the mixture was stirred at 50 ° C. for 14 hours. Ethyl acetate was added to the reaction solution, and a 5% citric acid aqueous solution was added.
The extract was washed with a saturated aqueous solution of sodium hydrogen carbonate and a saturated saline solution. After the organic layer was dried over anhydrous sodium sulfate, the solvent was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (dichloromethane: methanol = 30: 1).
([(6-methoxy-pyridin-3-yl)-[4- (6-methyl-2-trifluoro-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -carbamoyl ] -Methyl) -carbamic acid ter
1.20 g of t-butyl ester were obtained. 1.20 g of the obtained compound was dissolved in 10 ml of ethanol, 15 ml of 4N dioxane-hydrochloric acid was added, and the mixture was stirred at room temperature for 1 hour. The reaction solution was concentrated under reduced pressure, the residue was dissolved in ethyl acetate, and washed with a saturated aqueous solution of sodium hydrogen carbonate and a saturated saline solution. After the organic layer was dried over anhydrous sodium sulfate, the solvent was concentrated under reduced pressure.
The obtained crystals were finely pulverized and washed with hexane-ethyl acetate to obtain 870 mg (85%) of the title compound.

Mp 174-176 ° C .; ¹ H-NMR (DMSO-d ₆ ) δ: 8.49 (s, 1H), 8.24 (s, 1H),
8.06 (d, 1H, J = 8.6Hz), 7.74 (s, 1H), 7.64 (d, 1H, J
= 9.7Hz), 7.33 (d, 1H, J = 9.5Hz), 7.06 (d, 1H, J = 8.9H)
z), 3.92 (s, 3H), 3.75-3.65 (br, 2H), 2.22 (s, 3
H); MS (APCI, m / z): 463 (M + 1) +; HPLC (R): Rt. = 3.1 min. (Example 406) 2-methoxy-N- (6-methoxy-pyridine-3) -Yl) -N- [4-
(6-Methyl 2-trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -acetamide Using the compound of Example 265, the reaction was carried out in the same manner as in Example 381. The title compound was obtained. mp 185-187 ° C; ¹ H-NMR (DMSO-d ₆ ) δ: 8.48 (s, 1H), 8.24 (s, 1H),
8.06 (d, 1H, J = 8.6Hz), 7.67 (s, 1H), 7.62 (d, 1H, J
= 9.2Hz), 7.31 (d, 1H, J = 9.2Hz), 7.01 (d, 1H, J = 8.6H
z), 4.10-4.00 (br, 2H), 3.90 (s, 3H), 3.34 (s, 3
H), 2.21 (s, 3H); MS (APCI, m / z): 478 (M + 1) +; HPLC (R): Rt. = 4.7 min. (Example 407) Acetic acid [(6-methoxy- Pyridin-3-yl)-[4- (6-methyl2-
Trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -carbamoyl] -methyl ester The title compound was reacted using the compound of Example 265 in the same manner as in Example 382. I got mp 164-166 ° C; ¹ H-NMR (DMSO-d ₆ ) δ: 8.51 (s, 1H), 8.24 (s, 1H),
8.10 (d, 1H, J = 8.6Hz), 7.69 (s, 1H), 7.63 (d, 1H, J
= 10.0Hz), 7.31 (d, 1H, J = 9.5Hz), 7.04 (d, 1H, J = 8.
6Hz), 4.70-4.60 (br, 2H), 3.91 (s, 3H), 2.22 (s, 3
H), 2.13 (s, 3H); MS (APCI, m / z): 506 (M + 1) +; HPLC (R): Rt. = 4.8 min. (Example 408) (6-ethoxy-pyridine- 3-yl)-[4- (6-Methyl-2-trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -amine monohydrobromide Reference Example 73 Compound and (6-ethoxy-pyridin-3-yl)-
The reaction was carried out in the same manner as in Example 157 using thiourea (Reference Example 86) to obtain the title compound. ¹ H-NMR (DMSO-d ₆ ) δ: 10.46 (s, 1H), 8.48 (s, 1H),
8.47 (s, 1H), 8.02 (d, 1H, J = 8.9Hz), 7.70 (d, 1H, J = 9.2Hz), 7.39 (d, 1H,
J = 9.2Hz), 7.27 (s, 1H), 6.86 (d, 1H, J = 8.9Hz), 4.2
6 (q, 2H, J = 7.0Hz), 2.33 (s, 3H), 1.30 (t, 3H, J = 7.
0 Hz); MS (APCI, m / z): 420 (M + 1) +; HPLC (R): Rt. = 5.4 min. (Example 409) N- (6-ethoxy-pyridin-3-yl)- N- [4- (6-methyl2-
Trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -acetamide Using the compound of Example 408, the reaction was carried out in the same manner as in Example 280 to obtain the title compound. mp 158-160 ° C; ¹ H-NMR (DMSO-d ₆ ) δ: 8.42 (s, 1H), 8.26 (s, 1H),
8.03 (d, 1H, J = 8.6Hz), 7.65 to 7.60 (m, 2H), 7.31 (d,
1H, J = 9.2Hz), 6.98 (d, 1H, J = 8.9Hz), 4.34 (q, 2H,
J = 7.0Hz), 2.21 (s, 3H), 2.09 (s, 3H), 1.34 (t, 3H,
J (7.0 Hz); MS (APCI, m / z): 462 (M + 1) +; HPLC (R): Rt. = 5.6 min. (Example 410) (6-chloro-pyridin-3-yl) -[4- (2,6-Dimethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -carbamic acid isobutyl ester Using the compound of Example 395 as in Example 301 The same reaction was carried out to obtain the title compound.

Mp 186-187 ° C; 1H-NMR (CDCl3) δ 8.49 (dd, 1H, J = 0.5Hz, 2.7Hz),
8.31 (br s, 1H), 7.72 (dd, 1H, J = 2.7Hz, 8.4Hz), 7.
51 (dd, 1H, J = 0.5Hz, 8.4Hz), 7.39 (d, 1H, J = 8.9H
z), 7.03 (s, 1H), 6.97 (dd, 1H, J = 1.9Hz, 9.2Hz),
4.09 (d, 2H, J = 6.8Hz), 2.58 (s, 3H), 2.17 (s, 3H),
1.94 (sep, 1H, J = 6.8Hz), 0.86 (d, 6H, J = 6.8Hz); MS (APCI, m / z): 456 (M + 1) +, 458 (M + 1) +; HPLC (R): Rt. = 4.3 min. (Example 411) N- (6-chloro-pyridin-3-yl) -N- [4- (2,6-dimethyl-
Imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -acetamide Using the compound of Example 395, the reaction was carried out in the same manner as in Example 280 to obtain the title compound. mp 180-181 ° C; 1H-NMR (CDCl3) δ 8.54 (d, 1H, J = 2.7Hz), 8.27 (br
s, 1H), 7.76 (dd, 1H, J = 2.7Hz, 8.4Hz), 7.59 (d, 1H,
J = 8.4Hz), 7.39 (d, 1H, J = 9.5Hz), 7.05 (s, 1H), 6.9
7 (dd, 1H, J = 1.6Hz, 9.2Hz), 2.58 (s, 3H), 2.19 (s,
3H), 2.18 (s, 3H); MS (APCI, m / z): 398 (M + 1) +, 400 (M + 1) +; HPLC (R): Rt. = 3.1 min. (Example 412) ) 2-Amino-N- [4- (6-chloro-2-methylimidazo [1,2-α]
Pyridin-3-yl) -thiazol-2-yl] -N- (4-methoxy
-Phenyl) -acetamide dihydrochloride [4- (6-chloro-2-methyl-imidazo [1,2-α] pyridine-3-
The title compound was obtained in the same manner as in Example 378 using yl) -thiazol-2-yl]-(4-methoxy-phenyl) -amine (Example 81).

Mp 233-236 ° C .; 1H-NMR (DMSO-d6) δ: 8.91 (s, 1H), 8.51 (brs, 2H),
7.88 (s, 1H), 7.87 (d, 1H, J = 7.3Hz), 7.78 (d, 1H,
J = 9.5Hz), 7.60 (d, 2H, J = 8.9Hz), 3.85 (s, 3H), 3.
73 (brs, 2H), 2.63 (s, 3H); MS (APCI, m / z): 428 (M + 1) +, 430 (M + 1) +; HPLC (R): Rt. = 2.5 min. (Example 413) 2-amino-N- [4- (6-chloro-2-methylimidazo [1,2-α])
Pyridin-3-yl) -thiazol-2-yl] -Np-tolyl-
Acetamide dihydrochloride The reaction was carried out in the same manner as in Example 378 using Example 86 to obtain the title compound. mp 193-195 ° C; 1H-NMR (DMSO-d6) δ: 8.85 (s, 1H), 8.47 (brs, 2H),
7.86 (s, 1H), 7.83 (d, 1H, J = 10.3Hz), 7.73 (d, 1
H, J = 10.0Hz), 7.55 (d, 2H, J = 8.1Hz), 7.48 (d, 2H, J
= 8.1Hz), 3.71 (brs, 2H), 2.62 (s, 3H), 2.43 (s, 3
H); MS (APCI, m / z): 412 (M + 1) +, 414 (M + 1) +; HPLC (R): Rt. = 2.6 min. (Example 414) 2-amino-N- [4- (2,8-Dimethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -N- (4-methoxy-phenyl) -acetamide dihydrochloride Example 51 The reaction was carried out in the same manner as in Example 378 to obtain the title compound. mp 218-219 ° C; 1H-NMR (DMSO-d6) δ: 8.61 (d, 1H, J = 6.8Hz), 8.55
(brs, 2H), 7.94 (s, 1H), 7.68 (d, 1H, J = 6.8Hz), 7.
59 (d, 2H, J = 8.9Hz), 7.24-7.16 (m, 3H), 3.85 (s, 3
H), 3.72 (brs, 2H), 2.60 (s, 6H); MS (APCI, m / z): 408 (M + 1) +; HPLC (R): Rt. = 2.2 min. (Example 415) 2-Amino-N- [4- (2,8-dimethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -Np-tolyl-acetamide dihydrochloride Reaction was carried out in the same manner as in Example 378 using 53 to give the title compound. mp 206-209 ° C; 1H-NMR (DMSO-d6) δ: 8.58 (d, 1H, J = 6.8Hz), 8.53
(brs, 2H), 7.94 (s, 1H), 7.68 (d, 1H, J = 7.0Hz), 7.
54 (d, 2H, J = 8.4Hz), 7.45 (d, 2H, J = 8.4Hz), 7.20
(t, 1H, J = 7.0Hz), 3.71 (brs, 2H), 2.60 (s, 3H), 2.
42 (s, 3H); MS (APCI, m / z): 392 (M + 1) +; HPLC (R): Rt. = 2.3 min. (Example 416) Acetic acid 4-[[4- (6- Chloro-2-methylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl]-(6-methoxy-pyridin-3-yl) -carbamoyl] -butyl ester The compound of Example 84 and The same reaction as in Example 382 was carried out using 5-acetoxy-pentanoic acid (Reference Example 89) to obtain the title compound.

Mp 114-117 ° C; 1H-NMR (CDCl ₃ ) δ: 8.74 (s, 1H), 8.20 (d, 1H, J = 2.
4Hz), 7.62 (dd, 1H, J = 2.2Hz, 8.4Hz), 7.42 (d, 1H,
J = 9.7Hz), 7.09 (s, 1H), 7.05 (d, 1H, J = 8.9Hz), 4.0
6 (t, 2H, J = 7.0Hz), 4.04 (s, 3H), 2.62 (s, 3H), 2.
43-2.35 (m, 2H), 2.05 (s, 3H), 1.85-1.64 (m, 4H); MS (APCI, m / z): 514 (M + 1) +, 516 (M + 1) +; HPLC (R): Rt. = 3.8 min. (Example 417) 4-[(6-Methoxy-pyridin-3-yl) -acetic acid]-[4- (6-methyl2
-Trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -carbamoyl] -butyl ester The compound of Example 265 and 5-acetoxy-pentanoic
The same reaction as in Example 382 was carried out using Acid (Reference Example 89) to obtain the title compound. mp 114-117 ° C; 1H-NMR (CDCl ₃ ) δ: 8.28 (s, 1H), 8.22 (d, 1H, J = 2.
7Hz), 7.60 (dd, 1H, J = 2.4Hz, 8.4Hz), 7.53 (d, 1H,
J = 9.2Hz), 7.40 (s, 1H), 7.09 (d, 1H, J = 7.8Hz), 6.9
5 (d, 1H, J = 8.6Hz), 4.05 (t, 2H, J = 6.5Hz), 4.01
(s, 3H), 2.42-2.33 (m, 2H), 2.18 (s, 3H), 2.03 (s,
3H), 1.84-1.78 (m, 2H), 1.71-1.64 (m, 2H); MS (APCI, m / z): 548 (M + 1) +; HPLC (R): Rt. = 5.3 min. Example 418) 2-amino-N- [4- (2,6-dimethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -N- (6-methylpyridine- 3-yl) -acetamide trihydrochloride The same reaction as in Example 378 was carried out using the compound of Example 362 to obtain the title compound.

Mp 203-204 ° C .; 1H-NMR (DMSO-d6) δ 8.82 (d, 1H, J = 2.7 Hz), 8.56 (b
rs, 1H), 8.52 (br s, 2H), 8.16 (dd, 1H, J = 2.7Hz,
8.4Hz), 7.96 (s, 1H), 7.85 (d, 1H, J = 9.2Hz), 7.77
(d, 1H, J = 9.2Hz), 7.64 (d, 1H, J = 8.6Hz), 3.81 (br
s, 2H), 2.62 (s, 3H), 2.58 (s, 3H), 2.29 (s, 3H); MS (APCI, m / z): 393 (M + 1) +; HPLC (R): Rt. = 1.9 min. (Example 419) Acetic acid [[4- (2,6-dimethyl-imidazo [1,2-α] pyridine-3)
-Yl) -thiazol-2-yl]-(6-methylpyridin-3-yl) -carbamoyl] -methyl ester The same reaction as in Example 382 was carried out using the compound of Example 362 to obtain the title compound. . mp 181-182 ° C; 1H-NMR (CDCl3) δ 8.68 (d, 1H, J = 2.2Hz), 8.30 (br
s, 1H), 7.75 (dd, 1H, J = 2.7Hz, 8.4Hz), 7.45-7.38
(m, 2H), 7.08 (s, 1H), 6.96 (dd, 1H, J = 1.6Hz, 8.9H
z), 4.58 (s, 2H), 2.71 (s, 3H), 2.58 (s, 3H), 2.21
(s, 3H), 2.18 (s, 3H); MS (APCI, m / z): 436 (M + 1) +; HPLC (R): Rt. = 2.8 min. (Example 420) Acetic acid 4- [ [4- (2,6-dimethyl-imidazo [1,2-α] pyridine
-3-yl) -thiazol-2-yl]-(6-methoxy-pyridine-3
-Yl) -carbamoyl] -butyl ester Example 307 and 5-acetoxy-pentanoic
The same reaction as in Example 382 was carried out using acid to obtain the title compound.

Mp 146-149 ° C .; 1H-NMR (CDCl ₃ ) δ: 8.42 (s, 1H), 8.23 (d, 1H, J = 2.
7Hz), 7.61 (dd, 1H, J = 3.0Hz, 8.9Hz), 7.45 (d, 1H,
J = 9.2Hz), 7.08 (s, 1H), 7.03 (dd, 1H, J = 1.6Hz, 9.2
Hz), 6.97 (d, 1H, J = 8.9Hz), 4.05 (t, 2H, J = 6.5Hz),
4.03 (s, 3H), 2.60 (s, 3H), 2.42-2.35 (m, 2H), 2.
15 (s, 3H), 2.03 (s, 3H), 1.85-1.76 (m, 2H), 1.72-1.
64 (m, 2H); MS (APCI, m / z): 494 (M + 1) +; HPLC (R): Rt. = 3.6 min. (Example 421) Acetic acid 4-[[4- (2, 8-dimethyl-imidazo [1,2-α] pyridine
-3-yl) -thiazol-2-yl]-(6-methoxy-pyridine-3
-Yl) -Carbamoyl] -butyl ester The same reaction as in Example 382 was carried out using the compound of Example 55 and 5-acetoxy-pentanoic acid (Reference Example 89) to give the title compound. mp 140-143 ° C; 1H-NMR (CDCl ₃ ) δ: 8.35 (d, 1H, J = 7.0Hz), 8.18 (d,
1H, J = 2.4Hz), 7.59 (dd, 1H, J = 2.7Hz, 8.6Hz), 7.06
(s, 1H), 6.94 (d, 1H, J = 8.9Hz), 6.92 (d, 1H, J = 6.
8Hz), 6.48 (t, 1H, J = 6.5Hz), 4.05 (t, 2H, J = 6.5Hz),
4.03 (s, 3H), 2.60 (s, 3H), 2.58 (s, 3H), 2.40-2.
36 (m, 2H), 2.03 (s, 3H), 1.84-1.78 (m, 2H), 1.72-1.
64 (m, 2H); MS (APCI, m / z): 494 (M + 1) +; HPLC (R): Rt. = 3.5 min. (Example 422) Acetic acid 3-[(6-methoxy-pyridine) -3-yl)-[4- (6-methyl2
-Trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -carbamoyl] -propyl ester Using the compound of Example 265 and 4-acetoxy-butyric acid (Reference Example 91) The same reaction as in Example 382 was carried out to obtain the title compound. mp 172-174 ° C; ¹ H-NMR (DMSO-d ₆ ) δ: 8.45 (s, 1H), 8.24 (s, 1H),
8.04 (d, 1H, J = 8.9Hz), 7.70-7.60 (m, 2H), 7.31 (d,
1H, J = 9.2Hz), 7.03 (d, 1H, J = 8.9Hz), 4.01 (t, 2H,
J = 6.5Hz), 3.91 (s, 3H), 2.45-2.35 (br, 2H), 2.21
(s, 3H), 2.00-1.85 (m, 5H); MS (APCI, m / z): 534 (M + 1) +; HPLC (R): Rt. = 5.3 min. (Example 423) 2- Amino-N- [4- (6-methyl-2-trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -N-
p-Tolyl-acetamide dihydrochloride Using the compound of Example 263, the reaction was carried out in the same manner as in Example 378 to obtain the title compound.

¹ H-NMR (DMSO-d ₆ ) δ: 8.22 (s, 1H), 7.7
2 (s, 1H), 7.65-7.50 (m, 3H), 7.44 (d, 2H, J = 8.1H
z), 7.31 (d, 1H, J = 7.8Hz), 3.70-3.60 (br, 2H), 2.
40 (s, 3H), 2.19 (s, 3H); MS (APCI, m / z): 446 (M + 1) +; HPLC (R): Rt. = 3.2 min. (Example 424) 2-amino -N- (4-methoxy-phenyl) -N- [4- (6-methyl2
-Trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -acetamide dihydrochloride The title compound was reacted in the same manner as in Example 378 using the compound of Example 261. I got mp 208-211 ° C; ¹ H-NMR (DMSO-d ₆ ) δ: 8.25 (s, 1H), 7.72 (s, 1H),
7.70-7.55 (m, 3H), 7.31 (d, 1H, J = 9.5Hz), 7.16 (d,
2H, J = 8.6Hz), 3.83 (s, 3H), 3.75-3.65 (br, 2H), 2.
20 (s, 3H); MS (APCI, m / z): 462 (M + 1) +; HPLC (R): Rt. = 3.2 min. (Example 425) Acetic acid 3-[[4- (2, 6-dimethyl-imidazo [1,2-α] pyridine
-3-yl) -thiazol-2-yl]-(6-methoxy-pyridine-3
-Yl) -Carbamoyl] -propyl ester The same reaction as in Example 382 was carried out using the compound of Example 307 and 4-acetoxy-butylic acid (Reference Example 91) to give the title compound. mp 168-170 ° C; ¹ H-NMR (DMSO-d ₆ ) δ: 8.44 (s, 1H), 8.38 (s, 1H),
8.02 (d, 1H, J = 8.9Hz), 7.44 (s, 1H), 7.37 (d, 1H, J
= 8.9Hz), 7.10-7.00 (m, 2H), 4.01 (t, 2H, J = 6.5Hz),
3.94 (s, 3H), 2.46 (s, 3H), 2.50-2.30 (br, 2H),
2.10 (br, 3H), 2.00-1.80 (m, 5H); MS (APCI, m / z): 480 (M + 1) +; HPLC (R): Rt. = 3.4 min. (Example 426) Acetic acid 3-[[4- (2,8-dimethyl-imidazo [1,2-α] pyridine
-3-yl) -thiazol-2-yl]-(6-methoxy-pyridine-3
-Yl) -carbamoyl] -propyl ester The same reaction as in Example 382 was carried out using the compound of Example 55 and 4-acetoxy-butylic acid (Reference Example 91) to give the title compound.

Mp 157-159 ° C .; ¹ H-NMR (DMSO-d ₆ ) δ: 8.39 (s, 1H), 8.34 (d, 1H, J =
7.0Hz), 7.99 (d, 1H, J = 8.6Hz), 7.47 (s, 1H), 7.07
(d, 1H, J = 8.1Hz), 7.01 (d, 1H, J = 6.8Hz), 6.59 (dd,
1H, J = 6.8Hz, J = 6.8Hz), 4.02 (t, 2H, J = 3.5Hz), 3.9
8 (s, 3H), 2.50 (s, 3H), 2.45-2.35 (m, 5H), 2.00-1.
85 (m, 5H); MS (APCI, m / z): 480 (M + 1) +; HPLC (R): Rt. = 3.3 min. (Example 427) Acetic acid 3-[[4- (6- Chloro-2-methylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl]-(6-methoxy-pyridin-3-yl) -carbamoyl] -propyl ester Compound of Example 84 The same reaction as in Example 382 was carried out using 4-acetoxy-butylic acid (Reference Example 91) to obtain the title compound. mp 170-171 ° C; ¹ H-NMR (DMSO-d ₆ ) δ: 8.71 (s, 1H), 8.41 (s, 1H),
8.00 (d, 1H, J = 8.9Hz), 7.55-7.50 (m, 2H), 7.22 (d,
1H, J = 9.5Hz), 7.08 (d, 1H, J = 8.6Hz), 4.01 (t, 2H,
J = 6.5Hz), 3.94 (s, 3H), 2.50 (s, 3H), 2.49-2.30 (b
r, 2H), 2.00-1.80 (br, 5H); MS (APCI, m / z): 500 (M + 1) +, 502 (M + 1) +; HPLC (R): Rt. = 3.8 min. Example 428: 2-amino-N- [4- (2,6-dimethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -Np-tolyl-acetamide Dihydrochloride The compound of Example 59 was reacted in the same manner as in Example 378 to obtain the title compound. 1H-NMR (DMSO-d6) δ 8.60 (br s, 1H), 8.54 (br s, 2
H), 7.91 (s, 1H), 7.83 (d, 1H, J = 9.2Hz), 7.72 (d, 1
H, J = 9.2Hz), 7.62 (d, 2H, J = 8.9Hz), 7.21 (d, 2H, J
= 8.9Hz), 3.70 (br s, 2H), 2.60 (s, 3H), 2.43 (s, 3
H), 2.23 (s, 3H); MS (APCI, m / z): 392 (M + 1) +; HPLC (R): Rt. = 2.3 min. (Example 429) 2-amino-N- [ 4- (2,6-dimethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -N- (4-methoxy-phenyl) -acetamide dihydrochloride Compound of Example 57 The reaction was carried out in the same manner as in Example 378 to obtain the title compound.

Mp 193-195 ° C. (dec.); 1H-NMR (DMSO-d6) δ 8.63 (br s, 1H), 8.54 (br s, 2
H), 7.91 (s, 1H), 7.83 (d, 1H, J = 9.2Hz), 7.72 (d, 1
H, J = 9.2Hz), 7.62 (d, 2H, J = 8.9Hz), 7.21 (d, 2H, J
= 8.9Hz), 3.85 (s, 3H), 3.72 (br s, 2H), 2.60 (s, 3
H), 2.25 (s, 3H); MS (APCI, m / z): 408 (M + 1) +; HPLC (R): Rt. = 2.2 min. (Example 430) [4- (2,6 -Dimethyl-imidazo [1,2-α] pyridin-3-yl)
-Thiazol-2-yl]-(2-methoxy-phenyl) -amine 1
The reaction was carried out in the same manner as in Example 157 using (2-methoxy-phenyl) -thiourea and the compound of Reference Example 5 to give the title compound. 1H-NMR (DMSO-d6) δ: 9.94 (s, 1H), 9.12 (s, 1H),
8.26 (d, 1H, J = 7.6Hz), 7.90 (d, 1H, J = 9.5Hz), 7.84
(d, 1H, J = 9.2Hz), 7.42 (d, 1H, J = 1.6Hz), 7.11-6.9
2 (m, 3H), 3.89 (s, 3H), 2.64 (s, 3H), 2.44 (s, 3
H); MS (APCI, m / z): 351 (M + 1) +; HPLC (R): Rt. = 3.4 min. (Example 431) N- [4- (2,6-dimethyl-imidazo [ [1,2-α] pyridin-3-yl) -thiazol-2-yl] -N- (2-methoxy-phenyl) -acetamide The reaction was carried out in the same manner as in Example 280 using the compound of Example 430. The compound was obtained.

1H-NMR (CDCl ₃ ) δ: 8.41 (s, 1H), 7.52
(t, 1H, J = 7.6Hz), 7.40 (dd, 1H, J = 1.6Hz, 7.6Hz), 7.
36 (d, 1H, J = 9.2Hz), 7.18 (d, 1H, J = 7.6Hz), 7.13
(d, 1H, J = 8.1Hz), 7.01 (s, 1H), 6.91 (dd, 1H, J = 1.6
Hz, 8.9Hz), 3.82 (s, 3H), 2.59 (s, 3H), 2.11 (s, 3
H), 2.09 (s, 3H); MS (APCI, m / z): 393 (M + 1) +; HPLC (R): Rt. = 3.3 min. (Example 432) N- (6-methylpyridine) -3-yl) -N- [4- (6-Methyl-2-trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -acetamide Using the compound of Example 456 The reaction was carried out in the same manner as in Example 280 to obtain the title compound. mp 222-224 ° C; ¹ H-NMR (DMSO-d ₆ ) δ: 8.71 (s, 1H), 8.21 (s, 1H),
8.02 (d, 1H, J = 8.4Hz), 7.65 to 7.60 (m, 2H), 7.48 (d,
1H, J = 8.4Hz), 7.30 (d, 1H, J = 9.2Hz), 2.55 (s, 3H),
2.21 (s, 3H), 2.08 (s, 3H); MS (APCI, m / z): 432 (M + 1) +; HPLC (R): Rt. = 4.2 min. (Example 433) 2-methoxy -N- (6-methylpyridin-3-yl) -N- [4- (6-
Methyl 2-trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -acetamide The compound of Example 531 was used and reacted in the same manner as in Example 381 to give the title compound. Obtained. mp 174-176 ° C; ¹ H-NMR (DMSO-d ₆ ) δ: 8.73 (s, 1H), 8.19 (s, 1H),
8.05 (d, 1H, J = 8.4Hz), 7.67 (s, 1H), 7.62 (d, 1H, J
= 9.2Hz), 7.48 (d, 1H, J = 8.1Hz), 7.30 (d, 1H, J = 9.2H
z), 4.02 (s, 2H), 3.35 (s, 3H), 2.55 (s, 3H), 2.21
(s, 3H); MS (APCI, m / z): 462 (M + 1) +; HPLC (R): Rt. = 4.2 min. (Example 434) [(6-Methylpyridin-3-yl) acetic acid )-[4- (6-Methyl-2-trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -carbamoyl] -methyl ester Using the compound of Example 456. The reaction was carried out in the same manner as in Example 382 to obtain the title compound.

Mp 179-182 ° C .; ¹ H-NMR (DMSO-d ₆ ) δ: 8.77 (s, 1H), 8.20 (s, 1H),
8.08 (d, 1H, J = 8.4Hz), 7.70 (s, 1H), 7.62 (d, 1H, J
= 9.2Hz), 7.51 (d, 1H, J = 8.1Hz), 7.31 (d, 1H, J = 9.2H
z), 4.62 (s, 2H), 2.55 (s, 3H), 2.22 (s, 3H), 2.13
(s, 3H); MS (APCI, m / z): 490 (M + 1) +; HPLC (R): Rt. = 4.4 min. (Example 435) 2-amino-N- (6-methylpyridine) -3-yl) -N- [4- (6-methyl-2-trifluoromethylimidazo [1,2-α] pyridine-
3-yl) -thiazol-2-yl] -acetamide trihydrochloride The title compound was obtained by carrying out a reaction in the same manner as in Example 378 using the compound of Example 456. ¹ H-NMR (DMSO-d ₆ ) δ: 9.13 (s, 1H), 8.58 (d, 1H, J =
8.6Hz), 8.18 (s, 1H), 7.92 (d, 1H, J = 8.4Hz), 7.81
(s, 1H), 7.64 (d, 1H, J = 9.2Hz), 7.34 (d, 1H, J = 9.5H
z), 3.90-3.70 (br, 2H), 2.74 (s, 3H), 2.26 (s, 3
H); MS (APCI, m / z): 447 (M + 1) +; HPLC (R): Rt. = 2.9 min. (Example 436) 2-amino-N- (6-ethoxy-pyridine-3) -Yl) -N- [4- (6-
Methyl 2-trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -acetamide The compound of Example 408 was reacted in the same manner as in Example 405 to give the title compound. Obtained. mp 199-202 ° C; ¹ H-NMR (DMSO-d ₆ ) δ: 8.48 (s, 1H), 8.25 (s, 1H),
8.03 (d, 1H, J = 9.5Hz), 7.75 (s, 1H), 7.34 (d, 1H, J
= 9.5Hz), 7.04 (d, 1H, J = 8.6Hz), 4.36 (q, 2H, J = 7.0H
z), 3.85-3.70 (br, 2H), 2.22 (s, 3H), 1.34 (t, 3H,
MS (APCI, m / z): 477 (M + 1) +; HPLC (R): Rt. = 3.3 min. (Example 437) 2- (s) amino-propanoic acid 4- [[4- (6-Chloro-2-methylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl]-(6-methoxy-pyridin-3-yl) -carbamoyl] -butyl Ester 3 hydrochloride A reaction similar to that in Example 378 was carried out using 5- (2-tert-butoxycarbonyl- (s) amino-propionyloxy) -pentanoic acid (Reference Example 92) and the compound of Example 84, and described. The compound was obtained.

1H-NMR (DMSO-d6) δ: 8.96 (s, 1H), 8.4
6 (brs, 2H), 8.43 (d, 1H, J = 2.7Hz), 8.05 (dd, 1H,
J = 2.4Hz, 8.6Hz), 7.94-7.85 (m, 3H), 7.10 (d, 1H, J
= 8.9Hz), 4.21-3.97 (m, 2H), 3.93 (s, 3H), 3.81 (s,
1H), 2.63 (s, 3H), 2.50-2.31 (m, 2H), 1.70-1.56
(m, 4H), 1.39 (d, 3H, J = 7.3 Hz); MS (APCI, m / z): 543 (M + 1) +, 545 (M + 1) +; HPLC (R): Rt. (Example 438) 2-amino-N- (4-methoxy-phenyl) -N- [4- (6-methyl2
-Trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -acetamide The compound of Example 261 was reacted in the same manner as in Example 405 to obtain the title compound. . mp 160-162 ° C; ¹ H-NMR (DMSO-d ₆ ) δ: 8.27 (s, 1H), 7.65-7.55 (m, 2
H), 7.53 (d, 2H, J = 8.9Hz), 7.29 (d, 1H, J = 9.5Hz),
7.11 (d, 2H, J = 8.9Hz), 3.81 (s, 3H), 3.23 (s, 2H),
2.18 (s, 3H); MS (APCI, m / z): 462 (M + 1) +; HPLC (R): Rt. = 3.2 min. (Example 439) 2-amino-N- [4- ( 6-methyl-2-trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -N-
p-Tolyl-acetamide Using the compound of Example 263, the reaction was carried out in the same manner as in Example 405 to obtain the title compound. 1H-NMR (DMSO-d6) δ: 8.24 (s, 1H), 7.63-7.59 (m, 2
H), 7.49 (d, 2H, J = 8.1Hz), 7.38 (d, 2H, J = 8.1Hz),
7.29 (d, 1H, J = 9.5Hz), 3.34 (s, 2H), 3.21 (s, 1H),
2.38 (s, 3H), 2.18 (s, 3H); MS (APCI, m / z): 446 (M + 1) +; HPLC (R): Rt. = 4.3 min. (Example 440) 2-amino -Propanoic acid 4-[(6-methoxy-pyridin-3-yl)-[4- (6-methyl-2-trifluoromethylimidazo [1,2-
α] pyridin-3-yl) -thiazol-2-yl] -carbamoyl] -butyl ester 5- (2-tert-butoxycarbonyl- (s) amino-propionyloxy) -pentanoic acid (Reference Example 92) and Examples 265
The same reaction as in Example 405 was carried out using the compound of Example 405 to obtain the title compound.

1H-NMR (CDCl ₃ ) δ: 8.27 (s, 1H), 8.23
(d, 1H, J = 2.7Hz), 7.61 (dd, 1H, J = 2.7Hz, 8.6Hz),
7.53 (d, 1H, J = 8.9Hz), 7.40 (d, 1H, J = 0.8Hz), 7.09
(dd, 1H, J = 1.4Hz, 9.5Hz), 6.95 (dd, 1H, J = 0.8 Hz,
8.9Hz), 4.14-4.10 (m, 2H), 4.01 (s, 3H), 3.59 (d,
1H, J = 7.3Hz), 2.42-2.36 (m, 4H), 2.18 (s, 3H), 1.
84-1.74 (m, 2H), 1.72-1.66 (m, 2H), 1.36 (d, 3H, J
= 7.3 Hz); MS (APCI, m / z): 577 (M + 1) +; HPLC (R): Rt. = 3.6 min. (Example 441) 2-amino-propanoic acid 4-[[4- (2,6-dimethyl-imidazo
[1,2-α] pyridin-3-yl) -thiazol-2-yl]-(6-methoxy-pyridin-3-yl) -carbamoyl] -butyl ester trihydrochloride trihydrochloride 5- (2-tert The same reaction as in Example 378 was carried out using -butoxycarbonyl- (s) amino-propionyloxy) -pentanoic acid (Reference Example 92) and the compound of Example 61 to obtain the title compound. 1H-NMR (DMSO-d6) δ: 8.66 (s, 1H), 8.57 (brs, 2H),
8.48 (s, 1H), 8.06 (d, 1H, J = 8.6Hz), 7.86 (brs, 2H), 7.77 (brs, 1H), 7.08
(d, 1H, J = 8.6Hz), 4.20-4.00 (m, 3H), 3.93 (s, 2
H), 2.59 (s, 3H), 2.50-2.35 (m, 2H), 2.28 (s, 3H),
1.72-1.56 (m, 4H), 1.41 (d, 3H, J = 6.5Hz); MS (APCI, m / z): 523 (M + 1) +; HPLC (R): Rt. = 2.6 min. Example 442) 2-Amino-propanoic acid 4-[[4- (2,8-dimethyl-imidazo
[1,2-α] pyridin-3-yl) -thiazol-2-yl]-(6-methoxy-pyridin-3-yl) -carbamoyl] -butyl ester trihydrochloride 5- (2-tert-butoxycarbonyl The same reaction as in Example 378 was performed using-(s) amino-propionyloxy) -pentanoic acid (Reference Example 92) and the compound of Example 55 to obtain the title compound. 1H-NMR (DMSO-d6) δ: 8.66 (s, 1H), 8.60 (d, 1H, J =
6.5Hz), 8.55 (brs, 2H), 8.42 (s, 1H), 8.03 (d, 1H, J
= 8.6Hz), 7.89 (s, 1H), 7.72 (d, 1H, J = 6.8Hz), 7.26
(t, 1H, J = 6.5Hz), 7.03 (d, 1H, J = 8.4Hz), 4.20-4.0
0 (m, 3H), 3.92 (s, 3H), 2.59 (s, 3H), 2.51-2.35
(m, 2H), 1.99 (s, 3H), 1.70-1.58 (m, 4H), 1.40 (d,
3H, J = 7.0Hz); MS (APCI, m / z):.. 523 (M + 1) +; HPLC (R): Rt = 2.5 min ( Example 443) N 1 - ^(6- methoxy - pyridine -3-yl) -N ^1- [4- (6-methyl2
-Trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -ethane-1,2-diamine 1) (6-methoxy-pyridin-3-yl)-[4- (6-methyl-2-
500 mg (1.23) of trifluoromethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -amine
Mmol) and 2- (2-bromo-ethyl) -isoindole-
After dissolving 940 mg (3.70 mmol) of 1,3-dione in 40 ml of N, N-dimethylformamide, 500 mg of potassium carbonate was added and the mixture was stirred at 70 ° C. for 3 hours. 940 mg of 2- (2-bromo-ethyl) -isoindole-1,3-dione
(3.70 mmol) was added and the mixture was stirred at 70 ° C. for 4 hours. Ethyl acetate was added to the reaction solution, and the mixture was washed with a saturated aqueous solution of sodium hydrogen carbonate and saturated saline. The organic layer was dried over anhydrous sodium sulfate, the solvent was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (dichloromethane / methanol = 10: 1). Wash with 2- (2
-[(6-Methoxy-pyridin-3-yl)-[4- (6-methyl-2-trifluoromethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl]- Amino] -ethyl) -isoindole-1,
630 mg (1.09 mmol) of 3-dione were obtained.

2) Example 443 2- (2) obtained in 1)
-[(6-Methoxy-pyridin-3-yl)-[4- (6-methyl-2-trifluoromethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl]- Amino] -ethyl) -isoindole-1,
630 mg (1.09 mmol) of 3-dione was dissolved in 40 ml of ethanol, 2 ml of hydrazine was added, and the mixture was stirred at 60 ° C. for 6 hours. The residue obtained by concentrating the solvent under reduced pressure was dissolved in ethyl acetate and washed with saturated saline. After drying the organic layer over anhydrous sodium sulfate, the solvent was concentrated under reduced pressure to obtain the title compound (133 mg, 28%). ¹ H-NMR (DMSO-d ₆ ) δ: 8.55 (s, 1H), 8.43 (s, 1H),
7.98 (d, 1H, J = 8.9Hz), 7.68 (d, 1H, J = 9.2Hz), 7.37
(d, 1H, J = 9.2Hz), 7.07 (s, 1H), 6.98 (d, 1H, J = 8.9
Hz), 3.90 (s, 3H), 3.87 (t, 2H, J = 6.8Hz), 2.82 (t,
2H, J = 6.5Hz), 2.34 (s, 3H); MS (APCI, m / z): 449 (M + 1) +; HPLC (R): Rt. = 3.3 min. (Example 444) 4- Amino-N- [3- [2- (6-methoxy-pyridin-3-ylamino) -thiazol-4-yl] -2-methylimidazo [1,2-α] pyridin-6-yl] -butyrylamide 4HCl Salt (3- [3- [2- (6-methoxy-pyridin-3-ylamino) -thiazol-4-yl] -2-methylimidazo [1,2-α] pyridine-6-
52 mg (96.7 micromol) of tert-butyl carbamoyl] -propyl) -carbamate (Example 383) was dissolved in 1 ml of ethanol, 2 ml of 4N-hydrochloric acid-dioxane was added, the mixture was stirred at room temperature for 1 hour, and then tetrahydrofuran. 1 ml and 1 ml of ethanol were further added, followed by stirring at room temperature for 1 hour. The reaction solution was concentrated under reduced pressure, and the obtained crystals were washed with ethyl acetate-methanol to give the title compound (56m).
g was obtained.

1H-NMR (DMSO-d6) δ: 11.13 (s, 1H), 1
0.72 (s, 1H), 9.92 (s, 1H), 8.43 (d, 1H, J = 2.7Hz),
8.15 (dd, 1H, J = 2.7Hz, 8.9Hz), 7.99 (brs, 4H), 7.41
(s, 1H), 6.79 (d, 1H, J = 8.6Hz), 3.81 (s, 3H), 2.85
-2.75 (m, 2H), 2.60 (s, 3H), 2.56-2.51 (m, 2H), 1.89
-1.84 (m, 2H); MS (APCI, m / z): 438 (M + 1) +; HPLC (R): Rt. = 2.5 min. (Example 445) N- [4- (6-chloro) 2-methylimidazo [1,2-α] pyridine-
3-yl) -thiazol-2-yl] -N- (6-methylpyridine-3-
Yl) -acetamide The compound of Example 446 was reacted in the same manner as in Example 280 to obtain the title compound. mp 233-235 ° C; 1H-NMR (CDCl ₃ ) δ: 8.64 (dd, 1H, J = 0.8Hz, 2.2Hz),
8.56 (d, 1H, J = 2.7Hz), 7.68 (dd, 1H, J = 2.4Hz, 8.1H
z), 7.48-7.40 (m, 2H), 7.09 (s, 1H), 7.05 (dd, 1H,
J = 1.9Hz, 9.5Hz), 2.71 (s, 3H), 2.62 (s, 3H), 2.18
(s, 3H); MS (APCI, m / z): 398 (M + 1) +, 400 (M + 1) +; HPLC (R): Rt. = 3.0 min. (Example 446) [4- (6-Chloro-2-methylimidazo [1,2-α] pyridine-3-
Yl) -thiazol-2-yl]-(6-methylpyridin-3-yl)
-Amine monohydrobromide Compound of Reference Example 12 and (6-methyl-pyridin-3-yl)-
The reaction was carried out in the same manner as in Example 157 using thiourea (Reference Example 85) to obtain the title compound.

1H-NMR (DMSO-d6) δ: 11.16 (s, 1H), 9.
13 (d, 1H, J = 1.1Hz), 8.96 (d, 1H, J = 2.4Hz), 8.29 (d
d, 1H, J = 2.4Hz, 8.6Hz), 7.83 (d, 1H, J = 9.5Hz), 7.7
1-7.62 (m, 2H), 7.50 (s, 1H), 2.60 (s, 3H), 2.57
(s, 2H); MS (APCI, m / z): 356 (M + 1) +, 358 (M + 1) +; HPLC (R): Rt. = 2.3 min. (Example 447) N- [ 4- (2,6-dimethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -2-methoxy-N- (6-methylpyridin-3-yl) -acetamide The title compound was obtained by carrying out a reaction in the same manner as in Example 382 using the compound of Example 446 and methoxyacetic acid. mp 149-150 ° C; 1H-NMR (DMSO-d6) δ 8.72 (d, 1H, J = 2.2Hz), 8.30 (b
rs, 1H), 8.04 (dd, 1H, J = 2.7Hz, 8.4Hz), 7.53 (d,
1H, J = 8.1Hz), 7.47 (s, 1H), 7.38 (d, 1H, J = 8.1Hz),
7.04 (dd, 1H, J = 1.9Hz, 9.2Hz), 4.02 (s, 2H), 3.35
(s, 3H), 2.59 (s, 3H), 2.46 (s, 3H), 2.10 (s, 3
H); MS (APCI, m / z): 408 (M + 1) +; HPLC (R): Rt. = 3.5 min. (Example 448) [4- (2,8-dimethyl-imidazo [1, 2-α] pyridin-3-yl)
-Thiazol-2-yl]-(6-methylpyridin-3-yl) -amine monohydrobromide Compound of Reference Example 1 and (6-methyl-pyridin-3-yl) -thiourea (Reference Example 85) And the reaction was carried out in the same manner as in Example 157 to obtain the title compound.

1H-NMR (DMSO-d6) δ 11.41 (brs, 1H),
9.11 (br s, 1H), 8.96 (d, 1H, J = 6.8Hz), 8.30 (d, 1
H, J = 8.5Hz), 7.84 (d, 1H, J = 7.3Hz), 7.77 (d, 1H, J
= 8.5Hz), 7.68 (s, 1H), 7.47 (t, 1H, J = 7.0Hz), 2.67
(s, 3H), 2.64 (s, 3H), 2.62 (s, 3H); MS (APCI, m / z): 336 (M + 1) +; HPLC (R): Rt. = 2.1 min. Example 449) [[4- (6-Chloro-2-methylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl]-(6-methylpyridin-3-acetic acid)
Yl) -carbamoyl] -methyl ester The same procedure as in Example 382 was carried out using the compound of Example 446 to give the title compound. mp 182-197 ° C (dec.); 1H-NMR (CDCl ₃ ) δ: 8.64-8.61 (m, 2H), 7.77 (dd, 1H,
J = 3.0Hz, 8.4Hz), 7.49 (d, 1H, J = 7.8Hz), 7.43 (d, 2
H, J = 8.9Hz), 7.12 (s, 1H), 7.05 (dd, 1H, J = 1.9Hz,
9.5Hz), 4.59 (s, 2H), 2.72 (s, 3H), 2.62 (s, 3H),
2.22 (s, 3H); MS (APCI, m / z): 456 (M + 1) +, 458 (M + 1) +; HPLC (R): Rt. = 3.0 min. (Example 450) N- [4- (6-Chloro-2-methylimidazo [1,2-α] pyridine-
3-yl) -thiazol-2-yl] -2-methoxy-N- (6-methylpyridin-3-yl) -acetamide The reaction was carried out as in Example 382 using the compound of Example 446 and methoxyacetic acid. This gave the title compound.

Mp 179-181 ° C. (dec.); 1H-NMR (CDCl ₃ ) δ: 8.62 (d, 1H, J = 1.9 Hz), 8.57 (d,
1H, J = 2.7Hz), 7.70 (dd, 1H, J = 3.0Hz, 8.4Hz), 7.47
(d, 1H, J = 8.4Hz), 7.43 (d, 1H, J = 9.5Hz), 7.12 (s,
1H), 7.05 (dd, 1H, J = 2.2Hz, 9.5Hz), 4.03 (s, 2H),
3.46 (s, 3H), 2.72 (s, 3H), 2.62 (s, 3H); MS (APCI, m / z): 428 (M + 1) +, 430 (M + 1) +; HPLC (R) : 2.8 min. (Example 451) [[[4- (6-Chloro-2-methylimidazo [1,2-α] pyridine-3]
-Yl) -thiazol-2-yl]-(6-methylpyridin-3-yl) -carbamoyl] -methyl] -carbamic acid tert-butyl ester N- (tert-butoxycarbonylamino) butanoic acid and Example 446 The reaction was carried out in the same manner as in Example 382 using the compound to obtain the title compound. 1H-NMR (CDCl ₃ ) δ: 8.61 (d, 1H, J = 1.4Hz), 8.58 (d,
1H, J = 2.4Hz), 7.71 (dd, 1H, J = 2.4Hz, 8.4Hz), 7.46
(d, 1H, J = 8.4Hz), 7.41 (d, 1H, J = 9.5Hz), 7.11 (s,
1H), 7.06 (dd, 1H, J = 2.2Hz, 9.5Hz), 5.35 (brs, 1
H), 3.91 (d, 2H, J = 5.9Hz), 2.71 (s, 3H), 2.62 (s, 3
H); MS (APCI, m / z): 513 (M + 1) +, 515 (M + 1) +; HPLC (R): Rt. = 3.5 min. (Example 452) 2-amino-N- [4- (6-chloro-2-methylimidazo [1,2-α]
Pyridin-3-yl) -thiazol-2-yl] -N- (6-methylpyridin-3-yl) -acetamide trihydrochloride Reaction similar to that of Example 382 using the compound of Example 446 and methoxyacetic acid To give the title compound.

Mp 214-216 ° C. (dec.); 1H-NMR (DMSO-d6) δ: 8.84 (d, 2H, J = 2.2 Hz), 8.58
(brs, 2H), 8.23 (dd, 1H, J = 2.4Hz, 8.1Hz), 7.97 (s,
1H), 7.93 (d, 1H, J = 8.6Hz), 7.89 (dd, 1H, J = 1.6H
z, 9.5Hz), 7.72 (d, 1H, J = 8.4Hz), 3.80 (brs, 2H),
2.65 (s, 2H), 2.63 (s, 2H); MS (APCI, m / z): 413 (M + 1) +, 415 (M + 1) +; HPLC (R): Rt. = 2.0 min. Example 453 Amino-acetic acid 4-[(6-methoxy-pyridin-3-yl)-[4- (6-
Methyl 2-trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -carbamoyl] -butyl ester 5- (2-tert-butoxycarbonyl-acetoxy) -pentanoic acid (reference) Using the compound of Example 90) and Example 265, the reaction was carried out in the same manner as in Example 405 to obtain the title compound. 1H-NMR (CDCl ₃ ) δ: 8.28 (brs, 1H), 8.22 (d, 1H, J =
2.7Hz), 7.60 (dd, 1H, J = 2.7Hz, 8.9Hz), 7.54 (d, 1
H, J = 9.2Hz), 7.41 (s, 1H), 7.09 (dd, 1H, J = 1.9Hz,
9.5Hz), 6.95 (d, 1H, J = 8.9Hz), 4.13 (t, 2H, J = 6.2H
z), 4.01 (s, 3H), 3.42 (s, 2H), 2.38 (brs, 2H), 2.1
9 (s, 3H), 1.84-1.76 (m, 2H), 1.73-1.66 (m, 2H); MS (APCI, m / z): 563 (M + 1) +; HPLC (R): Rt. = 3.4 min. (Example 454) N ^1- (6-methoxy-pyridin-3-yl) -N ^1- [4- (6-methyl2
-Trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -propane-1,3-diamine 2- (3-bromo-propyl) -isoindole-1,3- The title compound was obtained by carrying out a reaction in the same manner as in Example 443 using dione and the compound of Example 265.

¹ H-NMR (DMSO-d ₆ ) δ: 8.56 (s, 1H), 8.3
7 (s, 1H), 7.93 (d, 1H, J = 8.9Hz), 7.68 (d, 1H, J = 9.
5Hz), 7.37 (d, 1H, J = 9.2Hz), 7.07 (s, 1H), 6.99
(d, 1H, J = 8.9Hz), 3.96 (t, 2H, J = 7.3Hz), 3.91 (s, 3
H), 2.64 (t, 2H, J = 6.5Hz), 2.34 (s, 3H), 1.77-1.65
(m, 2H); MS (APCI, m / z): 463 (M + 1) +; HPLC (R): Rt. = 3.3 min. (Example 455) N ^1- (6-methoxy-pyridine-3) -Yl) -N ^1- [4- (6-methyl2
-Trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -butane-1,4-diamine 2- (4-bromo-butyl) -isoindole-1,3- The title compound was obtained by carrying out a reaction in the same manner as in Example 443 using dione and the compound of Example 265. ¹ H-NMR (DMSO-d ₆ ) δ: 8.54 (s, 1H), 8.37 (s, 1H),
7.93 (d, 1H, J = 8.6Hz), 7.68 (d, 1H, J = 9.2Hz), 7.38
(d, 1H, J = 9.5Hz), 7.07 (s, 1H), 6.99 (d, 1H, J = 8.9
Hz), 3.95-3.85 (m, 5H), 2.34 (s, 3H), 1.80-1.60
(m, 2H), 1.50-1.35 (m, 2H); MS (APCI, m / z): 477 (M + 1) +; HPLC (R): Rt. = 3.4 min. (Example 456) (6 -Methylpyridin-3-yl)-[4- (6-methyl-2-trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -amine monohydrobromide Compound of Reference Example 73 and (6-methyl-pyridin-3-yl)-
The reaction was carried out in the same manner as in Example 157 using thiourea (Reference Example 85) to obtain the title compound.

¹ H-NMR (DMSO-d ₆ ) δ: 11.41 (s, 1H), 9.
20 (s, 1H), 8.44 (s, 1H), 8.32 (d, 1H, J = 8.9Hz), 7.
82 (d, 1H, J = 9.5Hz), 7.73 (d, 1H, J = 9.5Hz), 7.55
(s, 1H), 7.42 (d, 1H, J = 9.2Hz), 2.63 (s, 3H), 2.34
(s, 3H); MS (APCI, m / z): 390 (M + 1) +; HPLC (R): Rt. = 3.1 min. (Example 457) [4- (6-chloro-2-tri Fluoromethylimidazo [1,2-α]
Pyridin-3-yl) -thiazol-2-yl]-(6-ethoxy-pyridin-3-yl) -amine monohydrobromide Compound of Reference Example 70 and (6-ethoxy-pyridin-3-yl)
The reaction was carried out in the same manner as in Example 157 using -thiourea (Reference Example 86) to obtain the title compound. ¹ H-NMR (DMSO-d ₆ ) δ: 10.44 (s, 1H), 8.90 (s, 1H),
8.43 (s, 1H), 8.00 (d, 1H, J = 8.9Hz), 7.85 (d, 1H, J
= 9.7Hz), 7.58 (d, 1H, J = 9.7Hz), 7.32 (s, 1H), 6.82
(d, 1H, J = 8.9Hz), 4.26 (q, 2H, J = 7.0Hz), 1.30
(t, 3H, J = 7.0Hz); MS (APCI, m / z): 440 (M + 1) +, 442 (M + 1) +; HPLC (R): Rt. = 5.5 min. (Example 458) [4- (6-Chloro-2-trifluoromethylimidazo [1,2-α]
Pyridin-3-yl) -thiazol-2-yl]-(6-methylpyridin-3-yl) -amine monohydrobromide Compound of Reference Example 70 and (6-methyl-pyridin-3-yl)-
The reaction was carried out in the same manner as in Example 157 using thiourea (Reference Example 85) to obtain the title compound.

[0574] ¹ H-NMR (DMSO-d ₆ ) δ: 11.46 (s, 1H), 9.
16 (s, 1H), 8.81 (s, 1H), 8.37 (d, 1H, J = 8.6Hz), 7.
95-7.80 (m, 2H), 7.65-7.60 (m, 2H), 2.63 (s, 3H); MS (APCI, m / z): 410 (M + 1) +, 412 (M + 1) +; HPLC (R): Rt. = 3.3 min. (Example 459) 2-amino-N- [4- (6-chloro-2-trifluoromethylimid)
Dazo [1,2-α] pyridin-3-yl) -thiazol-2-yl]-
N- (6-Methoxy-pyridin-3-yl) -acetamide As in example 405 using the compound of example 256
The reaction was performed to obtain the title compound. mp 131-134 ° C; ¹ H-NMR (DMSO-d ₆ ) δ: 8.64 (s, 1H), 8.40 (s, 1H),
8.02 (d, 1H, J = 8.9Hz), 7.78 (d, 1H, J = 9.7Hz), 7.71
(s, 1H), 7.50 (d, 1H, J = 9.7Hz), 7.04 (d, 1H, J = 8.9H
z), 3.91 (s, 3H), 3.35-3.20 (br, 2H); MS (APCI, m / z): 483 (M + 1) +, 485 (M + 1) +; HPLC (R): Rt = 3.3 min. (Example 460) N- [4- (6-chloro-2-trifluoromethylimidazo [1,2-
α] pyridin-3-yl) -thiazol-2-yl] -2-methoxy-
N- (6-Methoxy-pyridin-3-yl) -acetamide Example using compound of Example 256 and methoxyacetic acid
The reaction was carried out in the same manner as in 382 to obtain the title compound. mp 168-170 ° C; ¹ H-NMR (DMSO-d ₆ ) δ: 8.62 (s, 1H), 8.45 (s, 1H),
8.06 (d, 1H, J = 8.9Hz), 7.78 (d, 1H, J = 9.7Hz), 7.73
(s, 1H), 7.51 (d, 1H, J = 9.5Hz), 7.03 (d, 1H, J = 8.9H
z), 4.15-4.00 (brs, 2H), 3.91 (s, 3H), 3.32 (s, 3
H); MS (APCI, m / z): 498 (M + 1) +, 500 (M + 1) +; HPLC (R): Rt. = 5.2 min. RQH-0955 (Example 461) Acetic acid [[ 4- (6-chloro-2-trifluoromethylimidazo
[1,2-α] pyridin-3-yl) -thiazol-2-yl]-(6-meth
Toxic-pyridin-3-yl) -carbamoyl] -methyles
As in Example 382 using the compound of Example 256
The reaction was performed to obtain the title compound.

Mp 157-159 ° C .; ¹ H-NMR (DMSO-d ₆ ) δ: 8.64 (s, 1H), 8.49 (s, 1H),
8.09 (d, 1H, J = 8.6Hz), 7.85-7.75 (m, 2H), 7.51 (d,
1H, J = 9.5Hz), 7.06 (d, 1H, J = 8.6Hz), 4.75-4.55 (br
s, 2H), 3.91 (s, 3H), 2.14 (s, 3H); MS (APCI, m / z): 526 (M + 1) +, 528 (M + 1) +; HPLC (R): Rt = 5.4 min. (Example 462) N- [4- (6-chloro-2-trifluoromethylimidazo [1,2-
α] pyridin-3-yl) -thiazol-2-yl] -N- (6-methylpyridin-3-yl) -acetamide The title compound was reacted using the compound of Example 458 in the same manner as in Example 280. I got mp 203-205 ° C; ¹ H-NMR (DMSO-d ₆ ) δ: 8.67 (s, 1H), 8.57 (s, 1H),
8.02 (d, 1H, J = 8.4Hz), 7.77 (d, 1H, J = 9.7Hz), 7.70
(s, 1H), 7.55-7.45 (m, 2H), 2.56 (s, 3H), 2.08 (s,
3H); MS (APCI, m / z): 452 (M + 1) +, 454 (M + 1) +; HPLC (R): Rt. = 4.6 min. (Example 463) 2-amino-N- [4- (6-Chloro-2-trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl]-
N- (6-Methylpyridin-3-yl) -acetamide Using the compound of Example 458, the reaction was carried out in the same manner as in Example 405 to obtain the title compound.

Mp 122-125 ° C .; ¹ H-NMR (DMSO-d ₆ ) δ: 8.90 (s, 1H), 8.64 (s, 1H),
8.04 (d, 1H, J = 8.4Hz), 7.86 (d, 1H, J = 9.7Hz), 7.59
(d, 1H, J = 9.7Hz), 7.38 (s, 1H), 7.20 (d, 1H, J = 8.6H
z), 3.85-3.70 (br, 2H), 2.41 (s, 3H); MS (APCI, m / z): 467 (M + 1) +, 469 (M + 1) +; HPLC (R): Rt = 3.0 min. (Example 464) N- [4- (6-chloro-2-trifluoromethylimidazo [1,2-
α] pyridin-3-yl) -thiazol-2-yl] -2-methoxy-
N- (6-Methylpyridin-3-yl) -acetamide The title compound was obtained by reacting in the same manner as in Example 382 using the compound of Example 458 and methoxyacetic acid. mp 181-183 ° C; ¹ H-NMR (DMSO-d ₆ ) δ: 8.70 (s, 1H), 8.56 (s, 1H),
8.04 (d, 1H, J = 8.1Hz), 7.80-7.70 (m, 2H), 7.55-7.45
(m, 2H), 4.02 (s, 2H), 3.33 (s, 3H), 2.55 (s, 3
H); MS (APCI, m / z): 482 (M + 1) +, 484 (M + 1) +; HPLC (R): Rt. = 4.5 min. (Example 465) Acetic acid [[4- ( 6-chloro-2-trifluoromethylimidazo
[1,2-α] pyridin-3-yl) -thiazol-2-yl]-(6-methylpyridin-3-yl) -carbamoyl] -methyl ester Example 382 was prepared using the compound of Example 458. The same reaction was carried out to obtain the title compound. mp 163-164 ° C; ¹ H-NMR (DMSO-d ₆ ) δ: 8.73 (s, 1H), 8.57 (s, 1H),
8.07 (d, 1H, J = 8.1Hz), 7.80-7.75 (m, 2H), 7.55-7.45
(m, 2H), 4.62 (s, 2H), 2.56 (s, 3H), 2.12 (s, 3
H); MS (APCI, m / z): 510 (M + 1) +, 512 (M + 1) +; HPLC (R): Rt. = 4.7 min. (Example 466) [4- (2, 6-dimethyl-imidazo [1,2-α] pyridin-3-yl)
-Thiazol-2-yl]-(6-trifluoromethylpyridine-
3-yl) -amine monohydrobromide Compound of Reference Example 5 and (6-trifluoromethyl-pyridine-3)
Example 1 using (-yl) -thiourea (Reference Example 93)
The reaction was carried out in the same manner as in 57 to give the title compound. 1H-NMR (DMSO-d6) δ 11.27 (br s, 1H), 8.94 (br s, 2
H), 8.38 (d, 1H, J = 6.2Hz), 7.93-7.82 (m, 3H), 7.64
(s, 1H), 2.63 (s, 3H), 2.44 (s, 3H); MS (APCI, m / z): 390 (M + 1) +; HPLC (R): Rt. = 3.3 min. Example 467) Acetic acid [[4- (2,8-dimethyl-imidazo [1,2-α] pyridine-3)
-Yl) -thiazol-2-yl]-(6-methylpyridin-3-yl) -carbamoyl] -methyl ester The compound of Example 448 was reacted in the same manner as in Example 382 to obtain the title compound. .

Mp 177-179 ° C .; 1H-NMR (CDCl3) δ 8.64 (d, 1H, J = 2.4 Hz), 8.25 (d,
1H, J = 7.3Hz), 7.72 (dd, 1H, J = 2.4Hz, 8.1Hz), 7.40
(d, 1H, J = 8.1Hz), 7.09 (s, 1H), 6.92 (d, 1H, J = 6.5H
z), 6.49 (t, 1H, J = 6.8Hz), 4.58 (s, 2H), 2.70 (s,
3H), 2.59 (s, 3H), 2.58 (s, 3H), 2.21 (s, 3H); MS (APCI, m / z): 436 (M + 1) +; HPLC (R): Rt. = 2.8 min. (Example 468) 2-amino-N- [4- (2,8-dimethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -N- (6- (Methylpyridin-3-yl) -acetamide trihydrochloride The compound of Example 448 was reacted in the same manner as in Example 378 to obtain the title compound. mp 205-206 ° C; 1H-NMR (DMSO-d6) δ 8.83 (d, 1H, J = 2.4Hz), 8.61 (b
rs, 2H), 8.55 (d, 1H, J = 7.0Hz), 8.18 (dd, 1H, J = 2.4
Hz, 8.4Hz), 8.00 (s, 1H), 7.73 (d, 1H, J = 7.3Hz),
7.65 (d, 1H, J = 8.4Hz), 7.29 (t, 1H, J = 7.3Hz), 3.73
(s, 2H), 2.63 (s, 3H), 2.60 (s, 3H), 2.58 (s, 3
H); MS (APCI, m / z): 393 (M + 1) +; HPLC (R): Rt. = 1.9 min. (Example 469) N- [4- (2,8-dimethyl-imidazo [ 1,2-α] pyridin-3-yl) -thiazol-2-yl] -N- (6-methylpyridin-3-yl) -acetamide Using the compound of Example 446 and reacting as in Example 280 To give the title compound. mp 197-198 ° C; 1H-NMR (CDCl3) δ 8.57 (d, 1H, J = 2.7Hz), 8.28 (d,
1H, J = 6.8Hz), 7.63 (dd, 1H, J = 2.7Hz, 8.1Hz), 7.38
(d, 1H, J = 8.1Hz), 7.06 (s, 1H), 6.90 (d, 1H, J = 6.8H
z), 6.47 (t, 1H, J = 6.8Hz), 2.70 (s, 3H), 2.59 (s,
3H), 2.57 (s, 3H), 2.16 (s, 3H); MS (APCI, m / z): 378 (M + 1) +; HPLC (R): Rt. = 2.6 min. (Example 470) Amino-acetic acid 4-[[4- (2,6-dimethyl-imidazo [1,2-α]
Pyridin-3-yl) -thiazol-2-yl]-(6-methoxy-pyridin-3-yl) -carbamoyl] -butyl ester trihydrochloride 5- (2-tert-butoxycarbonyl-acetoxy) -pentanoic acid ( The compound of Reference Example 90) and the compound of Example 307 were reacted in the same manner as in Example 378 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 8.66 (s, 1H), 8.4
8 (d, 1H, J = 2.4Hz), 8.44 (brs, 2H), 8.07 (dd, 1H,
J = 2.4Hz, 8.4Hz), 7.86 (s, 1H), 7.85 (d, 1H, J = 7.0H
z), 7.75 (d, 1H, J = 7.6Hz), 7.09 (d, 1H, J = 8.9Hz),
4.14 (brs, 2H), 3.93 (s, 3H), 3.83-3.78 (m, 2H),
2.60 (s, 2H), 2.49-2.35 (m, 4H), 2.28 (s, 3H), 1.7
0-1.60 (m, 2H); MS (APCI, m / z): 509 (M + 1) +; HPLC (R): Rt. = 2.5 min. (Example 471) N- [4- (2, 8-Dimethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -2-methoxy-N- (6-methylpyridin-3-yl) -acetamide The compound of Example 445 was prepared. The reaction was carried out in the same manner as in Example 381 to obtain the title compound. mp 199-200 ° C; 1H-NMR (CDCl3) δ 8.58 (d, 1H, J = 2.2Hz), 8.26 (d,
1H, J = 7.0Hz), 7.64 (dd, 1H, J = 2.4Hz, 8.1Hz), 7.39
(d, 1H, J = 8.1Hz), 7.08 (s, 1H), 6.91 (d, 1H, J = 6.8H
z), 6.47 (t, 1H, J = 6.8Hz), 4.01 (s, 2H), 3.45 (s,
3H), 2.70 (s, 3H), 2.58 (s, 3H), 2.57 (s, 3H); MS (APCI, m / z): 408 (M + 1) +; HPLC (R): Rt. = 2.5 min. (Example 472) 2-amino-N- [4- (2,6-dimethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -N- (6- (Trifluoromethylpyridin-3-yl) -acetamide trihydrochloride The title compound was obtained by carrying out a reaction in the same manner as in Example 378 using the compound of Example 466. mp 194-196 ° C; 1H-NMR (DMSO-d6) δ 9.19 (d, 1H, J = 2.4Hz), 8.58 (d
d, 1H, J = 2.2Hz, 8.6Hz), 8.51-8.46 (m, 3H), 8.30
(d, 1H, J = 8.6Hz), 7.95 (s, 1H), 7.80 (d, 1H, J = 9.5
Hz), 7.69 (d, 1H, J = 10.3Hz), 3.87 (br s, 2H), 2.55
(s, 3H), 2.24 (s, 3H); MS (APCI, m / z): 447 (M + 1) +; HPLC (R): Rt. = 2.2 min. (Example 473) N- [4 -(2,6-Dimethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -N- (4-methoxy-phenyl) -2-
(4-Methylpiperazin-1-yl) -acetamide Using the compound of Example 57 and N-methylpiperazine, the reaction was carried out in the same manner as in Example 515 to obtain the title compound.

1H-NMR (CDCl ₃ ) δ: 8.42 (s, 1H), 7.38-
7.32 (m, 3H), 7.09 (d, 2H, J = 8.9Hz), 7.02 (s, 1H),
6.93 (d, 1H, J = 9.2Hz), 3.90 (s, 3H), 3.17 (s, 2H),
2.59 (s, 3H), 2.59-2.50 (m, 8H), 2.30 (s, 3H), 2.0
9 (s, 3H); MS (APCI, m / z): 491 (M + 1) +; HPLC (R): Rt. = 2.3 min. (Example 474) N- [4- (2,6- Dimethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -N- (4-methoxy-phenyl) -2-
Pyrazol-1-yl-acetamide Example 51 using the compound of Example 57 and pyrazole
The reaction was carried out in the same manner as in Example 5 to obtain the title compound. 1H-NMR (CDCl ₃ ) δ: 8.42 (s, 1H), 7.59 (d, 1H, J = 1.
1Hz), 7.51 (d, 1H, J = 2.4Hz), 7.44 (d, 2H, J = 8.6H
z), 7.40 (d, 1H, J = 9.5Hz), 7.14 (d, 2H, J = 8.9Hz),
7.06 (s, 1H), 6.95 (d, 1H, J = 7.6Hz), 6.38-6.37 (m,
1H), 4.98 (s, 2H), 3.91 (s, 2H), 2.59 (s, 3H), 2.
10 (s, 3H); MS (APCI, m / z): 459 (M + 1) +; HPLC (R): Rt. = 3.3 min. (Example 475) 2-amino-N- [4- ( 6-chloro-2-trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl]-
N- (6-ethoxy-pyridin-3-yl) -acetamide Using the compound of Example 457, the reaction was carried out in the same manner as in Example 405 to obtain the title compound. mp 205-207 ° C; ¹ H-NMR (DMSO-d ₆ ) δ: 8.63 (s, 1H), 8.45 (s, 1H),
8.04 (d, 1H, J = 8.9Hz), 7.85-7.75 (m, 2H), 7.53 (d,
1H, J = 9.7Hz), 7.05 (d, 1H, J = 8.9Hz), 4.37 (q, 2H,
J = 7.0Hz), 3.90-3.70 (br, 2H), 1.35 (t, 3H, J = 7.0H
MS) (APCI, m / z): 497 (M + 1) +, 499 (M + 1) +; HPLC (R): Rt. = 3.4 min. (Example 476) 2-amino-N- [4- (6-Chloro-2-trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl]-
N- (4-Methoxy-phenyl) -acetamide dihydrochloride Using the compound of Example 257, the reaction was carried out in the same manner as in Example 378 to obtain the title compound. mp 209-211 ° C; ¹ H-NMR (DMSO-d ₆ ) δ: 8.63 (s, 1H), 7.85-7.75 (m, 2
H), 7.60 (d, 2H, J = 8.9Hz), 7.51 (d, 1H, J = 9.7Hz),
7.17 (d, 2H, J = 8.9Hz), 3.83 (s, 3H), 3.75-3.65 (b
r, 2H); MS (APCI, m / z): 482 (M + 1) +, 484 (M + 1) +; HPLC (R): Rt. = 3.3 min. (Example 477) N- (4 -Methoxy-phenyl) -2- (4-methylpiperazine-1-
Yl) -N- [4- (6-methyl-2-trifluoromethylimidazo
[1,2-α] pyridin-3-yl) -thiazol-2-yl] -acetamide Using the compound of Example 257 and N-methylpiperazine, the reaction was carried out in the same manner as in Example 515 to obtain the title compound. . mp 168-170 ° C; 1H-NMR (CDCl ₃ ) δ: 8.33 (s, 1H), 7.51 (d, 1H, J = 9.
4Hz), 7.40 (s, 1H), 7.33 (d, 2H, J = 8.9Hz), 7.10-7.
05 (m, 3H), 3.88 (s, 3H), 3.16 (s, 2H), 2.62-2.46
(m, 8H), 2.30 (s, 3H), 2.14 (s, 3H); MS (APCI, m / z): 545 (M + 1) +; HPLC (R): Rt. = 3.4 min. Example 478) 2-Diethylamino-N- (4-methoxy-phenyl) -N- [4- (6
-Methyl 2-trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -acetamide The reaction is carried out as in Example 515 using the compound of Example 257 and diethylamine. The title compound was obtained.

Mp 174-175 ° C .; 1H-NMR (CDCl ₃ ) δ: 8.34 (s, 1H), 7.51 (d, 1H, J = 9.
2Hz), 7.39 (s, 1H), 7.32 (d, 2H, J = 8.9Hz), 7.09-7.
04 (m, 3H), 3.88 (s, 3H), 3.29 (s, 2H), 2.66 (q, 4
H, J = 7.3Hz), 2.14 (s, 3H), 0.98 (t, 6H, J = 7.3Hz); MS (APCI, m / z): 518 (M + 1) +; HPLC (R): Rt = 3.5 min. (Example 479) N- (4-methoxy-phenyl) -N- [4- (6-methyl-2-trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazole 2-yl] -2-pyrrolidin-1-yl-acetamide Example 5 using the compound of Example 257 and pyrrolidine
The reaction was carried out in the same manner as in Example 15 to obtain the title compound. mp 178-180 ° C; 1H-NMR (CDCl ₃ ) δ: 8.33 (s, 1H), 7.51 (d, 1H, J = 9.
5Hz), 7.39 (s, 1H), 7.33 (d, 2H, J = 8.6Hz), 7.09-7.
05 (m, 3H), 3.88 (s, 3H), 3.32 (s, 2H), 2.65-2.60
(m, 4H), 2.14 (s, 3H), 1.83-1.79 (m, 4H); MS (APCI, m / z): 516 (M + 1) +; HPLC (R): Rt. = 3.4 min. Example 480: N- (4-methoxy-phenyl) -N- [4- (6-methyl-2-trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -2-morpholin-4-yl-acetamide Example 5 using the compound of Example 257 and morpholine
The reaction was carried out in the same manner as in Example 15 to obtain the title compound. mp 195-198 ° C; 1H-NMR (CDCl ₃ ) δ: 8.32 (s, 1H), 7.51 (d, 1H, J = 8.
6Hz), 7.40 (s, 1H), 7.33 (d, 2H, J = 8.6Hz), 7.10-7.
06 (m, 3H), 3.88 (s, 3H), 3.77-3.74 (m, 4H), 3.16
(s, 2H), 2.56-2.52 (m, 4H), 2.14 (s, 3H); MS (APCI, m / z): 532 (M + 1) +; HPLC (R): Rt. = 3.4 min. Example 481 N- (4-methoxy-phenyl) -N- [4- (6-methyl-2-trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] 2-Pyrazol-1-yl-acetamide Example 5 using the compound of Example 257 and pyrazole
The reaction was carried out in the same manner as in Example 15 to obtain the title compound.

Mp 188-191 ° C .; 1H-NMR (CDCl ₃ ) δ: 8.31 (s, 1H), 7.59 (d, 1H, J = 1.
9Hz), 7.54-7.50 (m, 2H), 7.45-7.42 (m, 3H), 7.14-
7.06 (m, 3H), 6.38-6.36 (m, 3H), 4.96 (s, 2H), 3.8
9 (s, 2H), 2.15 (s, 3H); MS (APCI, m / z): 513 (M + 1) +; HPLC (R): Rt. = 5.0 min. (Example 482) 2-imidazole -1-yl-N- (4-methoxy-phenyl) -N
-[4- (6-Methyl 2-trifluoromethylimidazo [1,2-α]
Pyridin-3-yl) -thiazol-2-yl] -acetamide Using the compound of Example 257 and imidazole, the reaction was carried out in the same manner as in Example 515 to obtain the title compound. 1H-NMR (CDCl ₃ ) δ: 8.28 (s, 1H), 7.51 (d, 1H, J = 8.
9Hz), 7.46-7.37 (m, 4H), 7.17-7.06 (m, 4H), 6.96
(s, 1H), 4.74 (s, 2H), 3.90 (s, 2H), 2.15 (s, 3H); MS (APCI, m / z): 513 (M + 1) +; HPLC (R): Rt . = 3.4 min. (Example 483) (4-isopropylphenyl)-[4- (6-methyl-2-trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -Amine monohydrobromide Using the compound of Reference Example 73 and (4-isopropyl-phenyl) -thiourea, the reaction was carried out in the same manner as in Example 157.
The title compound was obtained. 1H-NMR (DMSO-d6) δ: 10.34 (s, 1H), 8.53 (s, 1H),
7.70 (d, 1H, J = 9.2Hz), 7.51 (d, 2H, J = 8.6Hz), 7.39
(dd, 1H, J = 1.6Hz, 9.2Hz), 7.22 (d, 2H, J = 9.2Hz),
7.17 (s, 1H), 2.84 (sep, 1H, J = 7.0Hz), 2.33 (s, 3
H), 1.18 (d, 6H, J = 7.0 Hz); MS (APCI, m / z): 417 (M + 1) +; HPLC (R): Rt. = 6.8 min. (Example 484) (4 -Isopropoxy-phenyl)-[4- (6-methyl-2-trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -amine monohydrobromide Reference example 73 compounds and (4-isopropoxy-phenyl)-
The reaction was carried out in the same manner as in Example 157 using thiourea to obtain the title compound. 1H-NMR (DMSO-d6) δ: 10.27 (s, 1H), 8.52 (s, 1H),
7.69 (d, 1H, J = 8.4Hz), 7.52 (d, 2H, J = 8.9Hz), 7.39
(dd, 1H, J = 1.6Hz, 9.5Hz), 7.19 (s, 1H), 6.88 (d, 1
H, J = 8.9Hz), 4.52 (sep, 1H, J = 5.9Hz), 2.33 (s, 3
H), 1.23 (d, 6H, J = 5.9 Hz); MS (APCI, m / z): 433 (M + 1) +; HPLC (R): Rt. = 6.1 min. (Example 485) (4 -Ethyl-phenyl)-[4- (6-methyl-2-trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-
[Ill] -amine monohydrobromide Using the compound of Reference Example 73 and (4-ethyl-phenyl) -thiourea, the reaction was carried out in the same manner as in Example 157 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.39 (s, 1H), 8.
53 (s, 1H), 7.70 (d, 1H, J = 9.2Hz), 7.53 (d, 2H, J =
8.6Hz), 7.39 (dd, 1H, J = 1.4Hz, 9.2Hz), 7.24 (s, 1
H), 7.15 (d, 1H, J = 8.4Hz), 2.54 (q, 2H, J = 7.6Hz),
2.33 (s, 3H), 1.15 (t, 3H, J = 8.4Hz); MS (APCI, m / z): 403 (M + 1) +; HPLC (R): Rt. = 6.4 min. 486) [4- (6-Methyl 2-trifluoromethylimidazo [1,2-α]
Pyridin-3-yl) -thiazol-2-yl]-(4-trifluoromethoxy-phenyl) -amine monohydrobromide Using the compound of Reference Example 73 and (4-trifluoromethoxy-phenyl) -thiourea Then, the reaction was carried out in the same manner as in Example 157 to obtain the title compound. 1H-NMR (DMSO-d6) δ: 10.71 (s, 1H), 8.47 (s, 1H),
7.77-7.69 (m, 3H), 7.39 (dd, 1H, J = 1.4Hz, 9.2Hz),
7.34 (s, 1H), 7.32 (d, 2H, J = 8.4 Hz), 2.32 (s, 3H); MS (APCI, m / z): 459 (M + 1) +; HPLC (R): Rt. (Example 487) (4-ethoxy-phenyl)-[4- (6-methyl-2-trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazol-2
[-Yl] -amine monohydrobromide The compound of Reference Example 73 and (4-ethoxy-phenyl) -thiourea were reacted in the same manner as in Example 157 to obtain the title compound. ¹ H-NMR (DMSO-d ₆ ) δ: 10.29 (s, 1H), 8.52 (s, 1H),
7.69 (d, 1H, J = 9.5Hz), 7.53 (d, 2H, J = 8.9Hz), 7.39
(d, 1H, J = 9.5Hz), 7.19 (s, 1H), 6.90 (d, 2H, J = 8.9
Hz), 3.40 (q, 2H, J = 7.0Hz), 2.33 (s, 3H), 1.30 (t,
3H, J = 6.8Hz); MS (APCI, m / z): 419 (M + 1) +; HPLC (R): Rt. = 5.8 min. (Example 488) (3,4-dimethoxy-phenyl) -[4- (6-Methyl-2-trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -amine monohydrobromide The compound of Reference Example 73 and (3 Using (, 4-dimethoxy-phenyl) -thiourea, the reaction was carried out in the same manner as in Example 157,
The title compound was obtained. ¹ H-NMR (DMSO-d ₆ ) δ: 10.29 (s, 1H), 8.54 (s, 1H),
7.69 (d, 1H, J = 9.5Hz), 7.45-7.35 (m, 2H), 7.20 (s,
1H), 7.04 (d, 1H, J = 8.9Hz), 6.91 (d, 1H, J = 8.9Hz),
3.71 (s, 3H), 3.69 (s, 3H), 2.31 (s, 3H); MS (APCI, m / z): 435 (M + 1) +; HPLC (R): Rt. = 4.9 min. ( Example 489) (3,4-Dimethyl-phenyl)-[4- (6-methyl-2-trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazole
[2-yl] -amine monohydrobromide The compound of Reference Example 73 and (3,4-dimethyl-phenyl) -thiourea were reacted in the same manner as in Example 157 to obtain the title compound.

[0583] ^{1 H-NMR (DMSO-d} 6) δ: 10.32 (s, 1H), 8.
58 (s, 1H), 7.70 (d, 1H, J = 8.9Hz), 7.49 (s, 1H),
7.40 (d, 1H, J = 9.2Hz), 7.31 (d, 1H, J = 8.1Hz), 7.23
(s, 1H), 7.07 (d, 1H, J = 8.4Hz), 2.34 (s, 3H), 2.19
(s, 3H), 2.16 (s, 3H); MS (APCI, m / z): 403 (M + 1) +; HPLC (R): Rt. = 6.4 min. (Example 490) [4- ( 6-methyl-2-trifluoromethylimidazo [1,2-α]
Pyridin-3-yl) -thiazol-2-yl]-(4-trifluoromethylphenyl) -amine monohydrobromide Compound of Reference Example 73 and (4-trifluoromethyl-phenyl) -thiourea (Reference Example Example 1 using 2)
The reaction was carried out in the same manner as in 57 to give the title compound. ¹ H-NMR (DMSO-d ₆ ) δ: 10.97 (s, 1H), 8.47 (s, 1H),
7.86 (d, 2H, J = 8.9Hz), 7.80-7.65 (m, 3H), 7.40 (d,
2H, J = 8.4 Hz), 2.33 (s, 3H); MS (APCI, m / z): 443 (M + 1) +; HPLC (R): Rt. = 6.2 min. (Example 491) -Fluoro-4-methylphenyl)-[4- (6-methyl-2-trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -amine monohydrobromide Using the compound of Reference Example 73 and (3-fluoro-4-methyl-phenyl) -thiourea (Reference Example 45), the reaction was carried out in the same manner as in Example 157 to obtain the title compound.

¹ H-NMR (DMSO-d ₆ ) δ: 10.63 (s, 1H), 8.
55 (s, 1H), 7.80-7.65 (m, 2H), 7.40 (d, 1H, J = 9.5H
z), 7.32 (s, 1H), 7.25-7.15 (m, 2H), 2.33 (s, 3H),
2.15 (s, 3H); MS (APCI, m / z): 407 (M + 1) +; HPLC (R): Rt. = 6.2 min. (Example 492) (4-Chloro-phenyl)-[4 -(6-Methyl-2-trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-
[Ill] -amine monohydrobromide Using the compound of Reference Example 73 and (4-chloro-phenyl) -thiourea, the reaction was carried out in the same manner as in Example 157 to obtain the title compound. ¹ H-NMR (DMSO-d ₆ ) δ: 10.65 (s, 1H), 8.47 (s, 1H),
7.75-7.65 (m, 3H), 7.45-7.30 (m, 4H), 2.33 (s, 3
H); MS (APCI, m / z): 409 (M + 1) +, 411 (M + 1) +; HPLC (R): Rt. = 6.2 min. (Example 493) 1- [4- [ 4- (6-methyl-2-trifluoromethylimidazo [1,
2-α] pyridin-3-yl) -thiazol-2-ylamino] -phenyl] -ethanone monohydrobromide Using the compound of Reference Example 73 and (4-acetyl-phenyl) -thiourea (Reference Example 47) Then, the reaction was carried out in the same manner as in Example 157 to obtain the title compound. ¹ H-NMR (DMSO-d ₆ ) δ: 10.96 (s, 1H), 8.48 (s, 1H),
7.94 (d, 2H, J = 8.6Hz), 7.80-7.65 (m, 3H), 7.41 (d, 2H, J = 9.5Hz), 2.34 (s,
3H); MS (APCI, m / z): 417 (M + 1) +; HPLC (R): Rt. = 4.9 min. (Example 494) (2,3-dihydro-benzo [1,4] dioxin -6-yl)-[4- (6
-Methyl 2-trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -amine monohydrobromide Compound of Reference Example 73 and (2,3-dihydro-benzo) The reaction was carried out in the same manner as in Example 157 using [1,4] dioxin-6-yl) -thiourea (Reference Example 87) to obtain the title compound.

¹ H-NMR (DMSO-d ₆ ) δ: 10.30 (s, 1H), 8.
55 (s, 1H), 7.70 (d, 1H, J = 9.2Hz), 7.39 (d, 1H, J =
9.2Hz), 7.34 (s, 1H), 7.21 (s, 1H), 6.95 (d, 1H, J
= 8.9Hz), 6.81 (d, 1H, J = 8.9Hz), 5.45-5.15 (br, 4
H), 2.33 (s, 3H); MS (APCI, m / z): 433 (M + 1) +; HPLC (R): Rt. = 5.2 min. (Example 495) [4- (6-methyl) 2-trifluoromethylimidazo [1,2-α]
Pyridin-3-yl) -thiazol-2-yl]-(3,4,5-trimethoxy-phenyl) -amine Compound of Reference Example 73 and (3,4,5-trimethoxy-phenyl) -thiourea (Reference Example 88 Example 157)
The reaction was carried out in the same manner as in to give the title compound. ¹ H-NMR (DMSO-d ₆ ) δ: 10.43 (s, 1H), 8.56 (s, 1H),
7.69 (d, 1H, J = 9.2Hz), 7.39 (d, 1H, J = 9.2Hz), 7.25
(s, 1H), 7.02 (s, 2H), 3.71 (s, 6H), 3.61 (s, 3H),
2.31 (s, 3H); MS (APCI, m / z): 465 (M + 1) +; HPLC (R): Rt. = 4.9 min. (Example 496) 2-amino-N- (4-isopropyl) Phenyl) -N- [4- (6-methyl-2-trifluoromethylimidazo [1,2-α] pyridine-3-
Yl) -thiazol-2-yl] -acetamide Using the compound of Example 483, the reaction was carried out in the same manner as in Example 405 to obtain the title compound. mp 153-156 ° C; 1H-NMR (CDCl ₃ ) δ: 8.32 (s, 1H), 7.52-7.40 (m, 4
H), 7.31 (d, 2H, J = 8.4Hz), 7.05 (d, 1H, J = 9.2Hz),
3.42 (s, 2H), 3.01 (sep, 1H, J = 7.0Hz), 2.12 (s, 2
H), 1.30 (d, 6H, J = 7.0 Hz); MS (APCI, m / z): 474 (M + 1) +; HPLC (R): Rt. = 3.6 min. (Example 497) 2- Amino-N- (4-isopropoxy-phenyl) -N- [4- (6-
Methyl 2-trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -acetamide Using the compound of Example 484, the reaction was carried out in the same manner as in Example 405 to give the title compound. Obtained. mp 140-142 ° C; 1H-NMR (CDCl ₃ ) δ: 8.37 (s, 1H), 7.52 (d, 1H, J = 8.
4Hz), 7.41 (d, 1H, J = 0.5Hz), 7.28 (d, 2H, J = 9.2H
z), 7.09-7.03 (m, 3H), 4.59 (sep, 1H, J = 6.2Hz), 3.
43 (s, 2H), 2.14 (s, 2H), 1.38 (d, 6H, J = 6.2 Hz); MS (APCI, m / z): 490 (M + 1) +; HPLC (R): Rt. = 3.4 min. (Example 498) 2-amino-N- (4-ethyl-phenyl) -N- [4- (6-methyl2-
Trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -acetamide Using the compound of Example 485, the reaction was carried out in the same manner as in Example 405 to obtain the title compound. mp 154-156 ° C; 1H-NMR (CDCl ₃ ) δ: 8.33 (s, 1H), 7.51 (d, 1H, J = 8.
9Hz), 7.42 (d, 2H, J = 6.8Hz), 7.41 (s, 1H), 7.31
(d, 2H, J = 8.4Hz), 7.06 (dd, 1H, J = 2.2Hz, 9.2Hz),
3.40 (s, 2H), 2.76 (q, 2H, J = 7.8Hz), 2.12 (s, 3H),
1.30 (t, 3H, J = 7.8 Hz); MS (APCI, m / z): 460 (M + 1) +; HPLC (R): Rt. = 3.3 min. (Example 499) 2-amino-N -[4- (6-Methyl-2-trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -N-
(4-Trifluoromethoxy-phenyl) -acetamide Using the compound of Example 486, the reaction was carried out in the same manner as in Example 405 to obtain the title compound.

Mp 123-125 ° C .; 1H-NMR (CDCl ₃ ) δ: 8.22 (s, 1H), 7.55-7.43 (m, 6
H), 7.09 (dd, 1H, J = 1.6Hz, 9.5Hz), 3.40 (s, 2H),
2.14 (s, 3H); MS (APCI, m / z): 516 (M + 1) +; HPLC (R): Rt. = 3.4 min. (Example 500) 2-dimethylamino-N- (4- Methoxy-phenyl) -N- [4- (6
-Methyl 2-trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -acetamide 1) (4-methoxy-phenyl)-[4- (6-methyl-2- Trifluoromethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -amine hydrobromide (Example 558)
A solution of 5.76 g (11.9 mmol) in 60 ml of N, N-dimethylacetamide was added with a catalyst amount of 4-pyrrolidinopyridine and 1.58 ml of triethylamine (11.9 mmol).
Mmol). While stirring at room temperature, 1.04 ml (13.1 mmol) of chloroacetyl chloride was added to 5
After dropwise addition over a period of minutes, the mixture was stirred at 60 ° C. for 6 hours. Further, 1.04 ml of chloroacetyl chloride (11.9
(Mmol) was added and stirred at room temperature for 14 hours. Ethyl acetate was added to the reaction solution, and the mixture was washed with a saturated aqueous solution of sodium hydrogen carbonate and saturated saline. After the organic layer was dried over anhydrous sodium sulfate, the solvent was concentrated under reduced pressure, and the obtained crystals were finely pulverized.
After washing with hexane-ethyl acetate, 6.07 g, 2-chloro-
N- (4-Methoxy-phenyl) -N- [4- (6-methyl-2-trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -acetamide was obtained. .

MS (APCI, m / z): 481 (M + 1) +, 483 (M + 1) +; HPLC (R): Rt. = 5.6 min. 2) Example 500 1) 2-chloro -N- (4-methoxy-
Phenyl) -N- [4- (6-methyl-2-trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl]-
Acetamide (6.07 g) dissolved in N, N-dimethylformamide (40 ml) was dissolved in sodium iodide (1.89 m).
g (12.6 mmol) and 3.0 ml of dimethylamine (50% aqueous solution) were added, and the mixture was stirred at room temperature for 2 hours. A mixed solvent of ethyl acetate and tetrahydrofuran (ethyl acetate: tetrahydrofuran = 5: 1) was added to the reaction solution, and the mixture was washed with water, a saturated aqueous solution of sodium hydrogencarbonate, and finally with a saturated saline solution. The organic layer is dried over anhydrous sodium sulfate, the solvent is concentrated under reduced pressure, the residue is purified by silica gel column chromatography (ethyl acetate / ethanol = 20: 1), and the obtained crystals are finely ground and then hexane-ethyl acetate. Washed to give the title compound, 2-dimethylamino-N- (4-methoxy-phenyl) -N- [4- (6-methyl-2-trifluoromethylimidazo [1,2-α] pyridin-3-yl)- Thiazol-2-yl]
4.52 g (73%) of -acetamide were obtained. mp 123-125 ° C; 1H-NMR (CDCl ₃ ) δ: 8.32 (s, 1H), 7.51 (d, 1H, J = 9.
2Hz), 7.39 (s, 1H), 7.32 (d, 2H, J = 8.9 Hz), 7.09-
7.04 (m, 3H), 3.88 (s, 3H), 3.13 (s, 2H), 2.34 (s,
3H), 2.14 (s, 3H); MS (APCI, m / z): 490 (M + 1) +; HPLC (R): Rt. = 3.2 min. (Example 501) 2-amino-N- ( 4-methoxy-phenyl) -N- [4- (6-methyl2
-Trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -propionamide Performed using N- (tert-butoxycarbonyl) -L-alanine and the compound of Example 558 The reaction was carried out in the same manner as in Example 405 to obtain the title compound. mp 167-168 ° C; 1H-NMR (DMSO-d6) δ 8.25 (br s, 1H), 7.63-7.58 (m,
4H), 7.30 (dd, 1H, J = 1.5Hz, 9.2Hz), 7.11 (d, 2H,
J = 9.2Hz), 3.81 (s, 3H), 3.45 (q, 1H, J = 6.8Hz), 2.1
9 (s, 3H), 1.10 (d, 3H, J = 6.8 Hz); MS (APCI, m / z): 476 (M + 1) +; HPLC (R): Rt. = 3.4 min. (Example 502) N- (4-methoxy-phenyl) -2-methylamino-N- [4- (6-
Methyl 2-trifluoromethylimidazo [1,2-α] pyridi
N-yl) -thiazol-2-yl] -acetamido (tert-butoxycarbonyl-methyl-amino) -acetic acid and the compound of Example 558 were reacted with the compound of Example 405 to give the title compound. Obtained.

Mp 145-146 ° C .; 1H-NMR (DMSO-d6) δ 8.26 (br s, 1H), 7.63-7.54 (m,
4H), 7.30 (dd, 1H, J = 1.6Hz, 9.2Hz), 7.11 (d, 2H,
J = 8.9Hz), 3.81 (s, 3H), 3.22 (s, 2H), 2.26 (s, 3
H), 2.19 (s, 3H); MS (APCI, m / z): 476 (M + 1) +; HPLC (R): Rt. = 3.3 min. (Example 503) 2-amino-N- ( 4-methoxy-phenyl) -3-methyl N- [4- (6
-Methyl 2-trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -butyrylamide (4-methoxy-phenyl)-[4- (6-methyl-2) -Trifluoromethyl-imidazo [1,2-α] pyridin-3-yl)-
Thiazol-2-yl] -amine monohydrobromide (Example 5
58) Dissolve 1.00 g (2.06 mmol) in a mixture of 40 ml of dichloromethane and 4 ml of triethylamine,
2.13 g of dicyclohexylcarbodiimide (10.3
Mmol), 2.69 g (12.4 mmol) of L-2-tert-butoxycarbonylamino-3-methyl-butanoic acid and 4-
305.4 mg (2.06 mmol) of pyrrolidinopyridine was added, and the mixture was stirred at room temperature for 24 hours. Acetic acid was added to the reaction solution, stirred for 10 minutes, and then filtered. The filtrate was concentrated under reduced pressure, the residue was dissolved in ethyl acetate, and filtered again. The filtrate was concentrated under reduced pressure, the residue was dissolved in ethyl acetate, and washed with a 5% aqueous citric acid solution, distilled water, a saturated aqueous sodium hydrogen carbonate solution, and a saturated saline solution. After the organic layer was dried over anhydrous sodium sulfate, the solvent was concentrated under reduced pressure, and the obtained residue was separated by preparative thin-layer chromatography (dichloromethane / methanol = 20:
Purified in 1). The obtained crystals were dissolved in 30 ml of ethanol, and 15 ml of hydrochloric acid-dioxane was added.
Stirred for hours. The reaction solution was concentrated under reduced pressure, the residue was dissolved in ethyl acetate, and washed with a saturated aqueous solution of sodium hydrogen carbonate and a saturated saline solution. After drying the organic layer over anhydrous sodium sulfate,
After concentrating the solvent under reduced pressure and finely crushing the obtained crystals,
Wash with hexane-ethyl acetate, and give the title compound (800 mg).
(77%).

Mp 146-147 ° C .; 1H-NMR (DMSO-d6) δ 8.26 (br s, 1H), 7.63-7.56 (m,
4H), 7.30 (dd, 1H, J = 1.6Hz, 9.2Hz), 7.11 (d, 2H,
J = 8.9Hz), 3.81 (s, 3H), 3.08 (d, 1H, J = 6.5Hz), 2.2
0 (s, 3H), 1.92-1.80 (m, 1H), 0.82 (d, 3H, J = 6.8H
z), 0.74 (d, 3H, J = 6.8 Hz); MS (APCI, m / z): 504 (M + 1) +; HPLC (R): Rt. = 3.5 min. (Example 504) pyrrolidine- 2-carboxylic acid (4-methoxy-phenyl)-[4-
(6-Methyl 2-trifluoromethylimidazo [1,2-α] pyri
Zin-3-yl) -thiazol-2-yl] -amide Compound of Example 558 and L-pyrrolidin-1,2 dicarbo
Example 503 using 1-tert-butyl acid acid
The same reaction was performed to obtain the title compound. mp 146-148 ° C; 1H-NMR (DMSO-d6) δ 8.25 (br s, 1H), 7.63-7.56 (m,
4H), 7.29 (d, 1H, J = 9.5Hz), 7.10 (d, 2H, J = 8.6H
z), 3.81 (s, 3H), 3.71-3.64 (m, 1H), 3.00-2.94 (m,
1H), 2.67-2.64 (m, 1H), 2.19 (s, 3H), 1.69-1.52
(m, 2H), 1.27-1.02 (m, 2H); MS (APCI, m / z): 502 (M + 1) +; HPLC (R): Rt. = 3.5 min. (Example 505) 2- Amino-N- (4-ethoxy-phenyl) -N- [4- (6-methyl2
-Trifluoromethylimidazo [1,2-α] pyridine-3-i
L) -thiazol-2-yl] -acetamide As in example 405 using the compound of example 487.
The reaction was performed to obtain the title compound. mp 153-155 ° C; ¹ H-NMR (DMSO-d ₆ ) δ: 8.27 (s, 1H), 7.65-7.60 (m, 2
H), 7.51 (d, 2H, J = 8.9Hz), 7.29 (d, 1H, J = 9.2Hz),
7.08 (d, 2H, J = 8.9Hz), 4.07 (q, 2H, J = 7.0Hz), 3.25
-3.20 (br, 2H), 2.20 (s, 3H), 1.35 (t, 3H, J = 6.8H
MS) (APCI, m / z): 476 (M + 1) +; HPLC (R): Rt. = 3.4 min. (Example 506) 2-amino-N- (2,3-dihydro-benzo) [1,4] dioxin-6
-Yl) -N- [4- (6-methyl-2-trifluoromethylimidazo
[1,2-α] pyridin-3-yl) -thiazol-2-yl] -ace
Toamide As in Example 405 using the compound of Example 494
The reaction was performed to obtain the title compound.

Mp 188-190 ° C .; ¹ H-NMR (DMSO-d ₆ ) δ: 8.32 (s, 1H), 7.65-7.55 (m, 2
H), 7.31 (d, 1H, J = 9.2Hz), 7.22 (s, 1H), 7.10-7.00
(m, 2H), 4.35-4.20 (br, 4H), 3.30-3.20 (br, 2H),
2.23 (s, 3H); MS (APCI, m / z): 490 (M + 1) +; HPLC (R): Rt. = 3.3 min. (Example 507) N- (4-acetyl-phenyl)- 2-amino-N- [4- (6-methyl2
-Trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -acetamide Using the compound of Example 493, the reaction was carried out in the same manner as in Example 405 to obtain the title compound. . mp 185-187 ° C; ¹ H-NMR (DMSO-d ₆ ) δ: 8.20-8.10 (m, 3H), 7.81 (d, 2
H, J = 8.9Hz), 6.45 (s, 1H), 7.60 (d, 1H, J = 9.5Hz),
7.27 (d, 1H, J = 9.5Hz), 3.25-3.20 (br, 2H), 2.63
(s, 3H), 2.15 (s, 3H); MS (APCI, m / z): 474 (M + 1) +; HPLC (R): Rt. = 3.1 min. (Example 508) 2-amino- N- [4- (6-methyl-2-trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -N-
(4-Trifluoromethylphenyl) -acetamide Using the compound of Example 490, the reaction was carried out in the same manner as in Example 405 to obtain the title compound. mp 162-165 ° C; ¹ H-NMR (DMSO-d ₆ ) δ: 8.17 (s, 1H), 7.99 (d, 2H, J =
8.4Hz), 7.91 (d, 2H, J = 8.4Hz), 7.66 (s, 1H), 7.61
(d, 1H, J = 8.6Hz), 7.29 (d, 1H, J = 9.5Hz), 3.25-3.20
(br, 2H), 2.15 (s, 3H); MS (APCI, m / z): 500 (M + 1) +; HPLC (R): Rt. = 3.5 min. (Example 509) 2-amino- N- (3,4-dimethoxy-phenyl) -N- [4- (6-methyl-2-trifluoromethylimidazo [1,2-α] pyridine-
3-yl) -thiazol-2-yl] -acetamide Using the compound of Example 488, the reaction was carried out in the same manner as in Example 405 to obtain the title compound.

Mp 182-184 ° C .; ¹ H-NMR (DMSO-d ₆ ) δ: 8.30 (s, 1H), 7.65-7.60 (m, 2
H), 7.35-7.25 (m, 2H), 7.15-7.10 (m, 2H), 3.81 (s,
3H), 3.77 (s, 3H), 3.30-3.25 (br, 2H), 2.17 (s, 3
H); MS (APCI, m / z): 492 (M + 1) +; HPLC (R): Rt. = 3.2 min. (Example 510) 2-amino-N- (3-fluoro-4-methyl) Phenyl) -N- [4- (6
-Methyl 2-trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -acetamide The title compound was reacted using the compound of Example 491 in the same manner as in Example 405. I got mp 159-161 ° C; ¹ H-NMR (DMSO-d ₆ ) δ: 8.26 (s, 1H), 7.70-7.55 (m, 3
H), 7.47 (d, 1H, J = 8.1Hz), 7.37 (d, 1H, J = 8.1Hz),
7.30 (d, 1H, J = 9.7Hz), 3.30-3.20 (br, 2H), 2.30
(s, 3H), 2.19 (s, 3H); MS (APCI, m / z): 464 (M + 1) +; HPLC (R): Rt. = 3.4 min. (Example 511) 2-amino- N- (4-chloro-phenyl) -N- [4- (6-methyl2-
Trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -acetamide Using the compound of Example 492, the reaction was carried out in the same manner as in Example 405 to obtain the title compound.

Mp 177-179 ° C .; ¹ H-NMR (DMSO-d ₆ ) δ: 8.22 (s, 1H), 7.75-7.60 (m, 6
H), 7.30 (d, 1H, J = 9.5Hz), 3.25-3.20 (br, 2H), 2.2
0 (s, 3H); MS (APCI, m / z): 466 (M + 1) +, 468 (M + 1) +; HPLC (R): Rt. = 3.4 min. (Example 512) 2- Amino-N- (3,4-dimethyl-phenyl) -N- [4- (6-methyl-2-trifluoromethylimidazo [1,2-α] pyridine-3-
Yl) -thiazol-2-yl] -acetamide Using the compound of Example 489, the reaction was carried out in the same manner as in Example 405 to obtain the title compound. mp 170-172 ° C; ¹ H-NMR (DMSO-d ₆ ) δ: 8.23 (s, 1H), 7.65-7.55 (m, 2
H), 7.39 (s, 1H), 7.35-7.25 (m, 3H), 3.25-3.20 (b
r, 2H), 2.28 (s, 3H), 2.27 (s, 3H), 2.17 (s, 3H); MS (APCI, m / z): 460 (M + 1) +; HPLC (R): Rt. = 3.5 min. (Example 513) 2-amino-N- [4- (6-methyl-2-trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -N -
(3,4,5-Trimethoxy-phenyl) -acetamide Using the compound of Example 495, the reaction was carried out in the same manner as in Example 405 to obtain the title compound. mp 173-175 ° C; ¹ H-NMR (DMSO-d ₆ ) δ: 8.33 (s, 1H), 7.65-7.60 (m, 2
H), 7.30 (d, 1H, J = 9.2Hz), 7.01 (s, 2H), 3.78 (s,
6H), 3.71 (s, 3H), 2.18 (s, 3H); MS (APCI, m / z): 522 (M + 1) +; HPLC (R): Rt. = 3.2 min. (Example 514) 2-amino-N- (6-methoxy-pyridin-3-yl) -N- [4- (6-
Methyl 2-trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -acetamide dihydrochloride The reaction was carried out as in Example 378 using the compound of Example 265. The title compound was obtained.

Mp 187-190 ° C .; 1H-NMR (DMSO-d6) δ: 8.50 (d, 1H, J = 2.4 Hz), 8.48
(brs, 2H), 8.24 (s, 1H), 8.07 (dd, 1H, J = 2.2Hz, 8.
9Hz), 7.76 (s, 1H), 7.64 (d, 1H, J = 8.9Hz), 7.31
(d, 1H, J = 9.4Hz), 7.08 (d, 1H, J = 8.9Hz), 3.92 (s,
3H), 3.81 (s, 3H), 2.22 (s, 3H); MS (APCI, m / z): 463 (M + 1) +; HPLC (R): Rt. = 3.1 min. (Example 515) N- [4- (6-chloro-2-methylimidazo [1,2-α] pyridine-
3-yl) -thiazol-2-yl] -2-dimethylamino-N- (4-
Methoxy-phenyl) -acetamide 1) [4- (6-Chloro-2-methyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl]-(4-methoxy-phenyl)- A solution of 6.99 g (15.5 mmol) of the amine (Example 81) in 70 ml of N, N-dimethylacetamide was added with a catalyst amount of 4-pyrrolidinopyridine and 2.16 ml (15.5 mmol) of triethylamine. 1.36 ml of chloroacetyl chloride while stirring at room temperature
(17.1 mmol) was added dropwise over 5 minutes.
Stirred at C for 4 hours. Further, 1.36 ml (17.1 mmol) of chloroacetyl chloride was added, and the mixture was added at room temperature for 15 minutes.
Stirred for hours. Ethyl acetate was added to the reaction solution, and the mixture was washed with a saturated aqueous solution of sodium hydrogen carbonate and saturated saline. After the organic layer was dried over anhydrous sodium sulfate, the solvent was concentrated under reduced pressure, and the obtained crystals were finely pulverized, washed with hexane-ethyl acetate, and 3.95 g (yield 57%) of 2-chloro-N- [ 4- (6-Chloro-2-methylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -N- (4-methoxy-phenyl) -acetamide was obtained.

1H-NMR (CDCl ₃ ) δ: 8.83 (s, 1H), 7.71
(d, 1H, J = 7.7Hz), 7.36 (d, 2H, J = 8.9Hz), 7.23-7.13
(m, 2H), 7.18 (d, 2H, J = 8.9Hz), 4.16 (s, 2H), 3.5
5 (s, 3H), 2.70 (s, 3H); MS (APCI, m / z): 447 (M + 1) +, 449 (M + 1) +; HPLC (R): Rt. = 3.9 min. 2) Example 515 2-chloro-N- [4- (6-chloro-
2.52 g (5.63 mmol) of 2-methylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -N- (4-methoxy-phenyl) -acetamide was added to N, N- Sodium iodide 8 dissolved in dimethylformamide 10 ml
39 mg (5.63 mmol) and 1.0 ml of a 50% -dimethylamine aqueous solution were added, and the mixture was stirred at 60 ° C for 1 hour.
Ethyl acetate was added to the reaction solution, and the mixture was washed with water, a saturated aqueous solution of sodium hydrogen carbonate, and finally with a saturated saline solution. After the organic layer was dried over anhydrous sodium sulfate, the solvent was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography (dichloromethane / dichloromethane).
After purification with methanol (10: 1), the resulting crystals were finely ground, washed with hexane-ethyl acetate and washed with the title compound, N- [4- (6-chloro-2-methylimidazo [1,2-α]. ] Pyridin-3-yl) -thiazol-2-yl] -2-dimethylamino
1.15 g of -N- (4-methoxy-phenyl) -acetamide
(45%).

Mp 154-156 ° C .; 1H-NMR (CDCl ₃ ) δ: 8.74 (dd, 1H, J = 0.8 Hz, 2.2 Hz),
7.39 (dd, 1H, J = 0.8Hz, 9.5Hz), 7.31 (d, 2H, J = 8.6H
z), 7.12 (d, 2H, J = 8.6Hz), 7.06 (s, 1H), 7.03 (dd,
1H, J = 0.8Hz, 9.5Hz), 3.91 (s, 3H), 3.17 (s, 2H),
2.61 (s, 3H), 2.36 (s, 3H); MS (APCI, m / z): 456 (M + 1) +, 458 (M + 1) +; HPLC (R): Rt. = 2.5 min. Example 516 [[4- (6-Chloro-2-methylimidazo [1,2-α] pyridine-3-
Yl) -thiazol-2-yl]-(4-methoxy-phenyl) -amino] -acetic acid methyl ester The compound of Example 81 was reacted in the same manner as in Example 518 to obtain the title compound. 1H-NMR (CDCl ₃ ) δ: 9.00 (d, 1H, J = 1.4Hz), 8.38 (d,
1H, J = 2.4Hz), 8.02 (brs, 1H), 7.84 (dd, 1H, J = 3.0H
z, 8.9Hz), 7.48 (d, 1H, J = 8.9Hz), 7.13 (dd, 1H, J =
1.9Hz, 9.5Hz), 6.86 (d, 1H, J = 8.9Hz), 6.58 (s, 1
H), 4.62 (s, 2H), 4.00 (s, 3H), 3.85 (s, 3H), 2.59
(s, 3H); MS (APCI, m / z): 444 (M + 1) +, 446 (M + 1) +; HPLC (R): Rt. = 3.7 min. (Example 517) N- [ 4- (6-chloro-2-methylimidazo [1,2-α] pyridine-
3-yl) -thiazol-2-yl] -N- (4-methoxy-phenyl) -2-methylamino-acetamide As in example 515 using the compound of example 81 and a 40% aqueous solution of -methylamine. The reaction was performed to obtain the title compound. 1H-NMR (CDCl ₃ ) δ: 8.75 (s, 1H), 7.40 (d, 1H, J = 9.
5Hz), 7.33-7.25 (m, 4H), 7.12-7.02 (m, 3H), 3.90
(s, 3H), 3.39 (s, 2H), 2.62 (s, 3H), 2.46 (s, 3H); MS (APCI, m / z): 442 (M + 1) +, 444 (M + 1) +; HPLC (R): Rt. = 2.5 min. (Example 518) [(4-Methoxy-phenyl)-[4- (6-methyl-2-trifluoromethylimidazo [1,2-α] pyridine-3] -Yl) -thiazole
2-yl] -amino] -acetic acid methyl ester (4-methoxy-phenyl)-[4- (6-methyl-2-trifluoromethyl-imidazo [1,2-α] pyridin-3-yl) -thiazole
-2-yl] -amine monohydrobromide (Example 558) 48
After dissolving 5 mg (1.00 mmol) in 5 ml of N, N-dimethylformamide, 276 mg of potassium carbonate was dissolved.
(2.00 mmol), 189 μl (2.00 mmol) of bromoacetic acid methyl ester was added, and the mixture was stirred at 50 ° C. for 1 hour. Ethyl acetate was added to the reaction solution, and the mixture was washed with water and saturated saline. After the organic layer was dried over anhydrous sodium sulfate, the solvent was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography (dichloromethane / methanol = 25:
After purification in 1), the resulting crystals are finely ground,
Wash with hexane-ethyl acetate and wash with the title compound (439 mg)
(92% yield).

Mp 140-142 ° C .; 1H-NMR (CDCl ₃ ) δ: 8.46 (d, 1H, J = 1.4 Hz), 7.58 (d,
1H, J = 9.5Hz), 7.49 (d, 2H, J = 8.9Hz), 7.16 (dd, 1
H, J = 1.9Hz, 9.2Hz), 7.00 (d, 2H, J = 8.9Hz), 6.80
(s, 1H), 4.60 (s, 2H), 3.86 (s, 3H), 3.78 (s, 3H),
2.37 (s, 3H); MS (APCI, m / z): 477 (M + 1) +; HPLC (R): Rt. = 5.7 min. (Example 519) [(4-methoxy-phenyl)-[ 4- (6-methyl-2-trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazole
[-2-yl] -amino] -acetic acid [(4-methoxy-phenyl)-[4- (6-methyl-2-trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazole
2-yl] -amino] -acetic acid methyl ester (Example 51
8) 30 mg (63 micromol) of ethanol 2 ml
, And 94 μl of a 1N aqueous solution of sodium hydroxide was added thereto, followed by stirring at room temperature for 30 minutes. 0.28 ml of a 1N aqueous solution of sodium hydroxide and 1 ml of methanol were further added and 10
Ultrasound was applied for minutes. 376 μl of 1N-hydrochloric acid aqueous solution
Was added, the solvent was concentrated under reduced pressure, ethyl acetate was added to the residue, and the mixture was washed with water and saturated saline. The organic layer was dried over anhydrous sodium sulfate, and the solvent was concentrated under reduced pressure. The obtained crystals were finely pulverized, and washed with hexane-ethyl acetate to obtain 25 mg (yield: 86%) of the title compound.

1H-NMR (DMSO-d6) δ: 12.8 (brs, 1H),
8.55 (s, 1H), 7.66 (d, 1H, J = 9.2Hz), 7.52 (d, 2H,
J = 8.9Hz), 7.36 (d, 1H, J = 9.2Hz), 7.07 (d, 2H, J = 8.
9Hz), 7.03 (s, 1H), 4.53 (s, 2H), 3.81 (s, 3H), 2.3
5 (s, 3H); MS (APCI, m / z): 463 (M + 1) +; HPLC (R): Rt. = 4.7 min. (Example 520) 2-ethylamino-N- (4- Methoxy-phenyl) -N- [4- (6-
Methyl 2-trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -acetamide Example 503 using the compound of Example 558 and (Tert butoxycarbonylethylamino) acetic acid The reaction was carried out in the same manner as in to give the title compound. mp 135-136 ° C; 1H-NMR (DMSO-d6) δ 8.26 (br s, 1H), 7.63-7.54 (m,
4H), 7.30 (d, 1H, J = 9.2Hz), 7.11 (d, 2H, J = 9.2H
z), 3.81 (s, 3H), 3.28 (s, 2H), 2.52-2.46 (m, 2H),
2.19 (s, 3H), 0.97 (t, 3H, J = 7.2Hz); MS (APCI, m / z): 490 (M + 1) +; HPLC (R): Rt. = 3.4 min. (Example 521) 2-[(4-Methoxy-phenyl)-[4- (6-methyl-2-trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -amino]- Acetamide A reaction was carried out in the same manner as in Example 518 using 2-bromoacetamide to obtain the title compound.

Mp 240-243 ° C .; 1H-NMR (DMSO-d6) δ: 8.50 (d, 1H, J = 2.4 Hz), 8.48
(brs, 2H), 8.24 (s, 1H), 8.07 (dd, 1H, J = 2.2Hz, 8.
9Hz), 7.76 (s, 1H), 7.64 (d, 1H, J = 8.9Hz), 7.31
(d, 1H, J = 9.4Hz), 7.08 (d, 1H, J = 8.9Hz), 3.92 (s,
3H), 3.81 (s, 3H), 2.22 (s, 3H); MS (APCI, m / z): 462 (M + 1) +; HPLC (R): Rt. = Min. (Example 522) (4-methoxy-phenyl)-[4- (6-methyl2-trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazole
2-yl] -amino] -acetic acid sodium salt [(4-methoxy-phenyl)-[4- (6-methyl-2-trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazole
2-yl] -amino] -acetic acid (Example 519) 161 mg
(0.349 mmol) in 3 ml of dioxane,
0.349 ml of 1N-sodium hydroxide aqueous solution (0.3
(49 mmol) and lyophilized to give 175 mg of the title compound. 1H-NMR (DMSO-d6) δ: 8.79 (s, 1H), 7.63-7.58 (m, 3
H), 7.32 (dd, 1H, J = 1.6Hz, 8.9Hz), 6.97 (d, 2H, J =
8.9Hz), 6.86 (s, 1H), 4.02 (s, 2H), 3.78 (s, 3H),
2.35 (s, 3H); (Example 523) 2-[(6-methylpyridin-3-yl)-[4- (6-methyl-2-trifluoromethylimidazo [1,2-α] pyridin-3- Yl) -thiazol-2-yl] -amino] -acetamide Using the compound of Example 456 and 2-bromoacetamide, the reaction was carried out in the same manner as in Example 518 to obtain the title compound. 1H-NMR (DMSO-d6) δ: 8.71 (d, 1H, J = 2.7Hz), 8.51
(s, 1H), 7.95 (dd, 1H, J = 2.7Hz, 8.2Hz), 7.66 (d, 1
H, J = 8.9Hz), 7.63 (brs, 1H), 7.09 (s, 1H), 4.47
(s, 2H), 3.29 (s, 3H), 2.34 (s, 3H); MS (APCI, m / z): 447 (M + 1) +; HPLC (R): Rt. = 3.2 min. Example 524) [(6-Methylpyridin-3-yl)-[4- (6-methyl-2-trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -amino ] -Acetic acid methyl ester The title compound was obtained by reacting in the same manner as in Example 518 using the compound of Example 456 and bromoacetic acid methyl ester.

1H-NMR (DMSO-d6) δ: 8.66 (d, 1H, J = 2.
7Hz), 8.35 (s, 1H), 7.91 (dd, 1H, J = 2.4Hz, 8.1Hz),
7.67 (d, 1H, J = 9.2Hz), 7.43-7.36 (m, 2H), 7.16 (s,
1H), 4.72 (s, 2H), 3.69 (s, 3H), 2.52 (s, 3H), 2.3
3 (s, 3H); MS (APCI, m / z): 462 (M + 1) +; HPLC (R): Rt. = 4.2 min. (Example 525) 2-amino-N- (6-methyl) Pyridin-3-yl) -N- [4- (6-methyl-2-trifluoromethylimidazo [1,2-α] pyridine-
3-yl) -thiazol-2-yl] -acetamide Using the compound of Example 456, the reaction was carried out in the same manner as in Example 405 to obtain the title compound. mp 151-154 ° C; ¹ H-NMR (DMSO-d ₆ ) δ: 8.68 (s, 1H), 8.20 (s, 1H),
8.00 (d, 1H, J = 8.1Hz), 7.70-7.60 (m, 2H), 7.48 (d,
1H, J = 8.4Hz), 7.30 (d, 1H, J = 9.2Hz), 3.25-3.20 (b
(r, 2H), 2.55 (s, 3H), 2.21 (s, 3H); MS (APCI, m / z): 447 (M + 1) +; HPLC (R): Rt. = 2.9 min. 526) (4-Methoxy-phenyl)-[4- (2-methyl8-nitro-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -amine monohydrobromide Using the compound of Reference Example 94 and (4-methoxy-phenyl) -thiourea (Reference Example 3), the reaction was carried out in the same manner as in Example 157 to obtain the title compound. 1H-NMR (DMSO-d6) δ: 10.33 (s, 1H), 9.45 (d, 1H, J
= 7.0Hz), 8.73 (d, 1H, J = 7.8Hz), 7.57 (d, 1H, J = 7.3H)
z), 7.52 (d, 2H, J = 9.2Hz), 7.38 (s, 1H), 6.94 (d,
2H, J = 9.2Hz), 3.73 (s, 3H), 2.68 (s, 3H); MS (APCI, m / z): 382 (M + 1) +; HPLC (R): Rt. = 3.5 min. Example 527 N- (4-methoxy-phenyl) -N- [4- (2-methyl8-nitro-
Imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -acetamide Using the compound of Example 526, the reaction was carried out in the same manner as in Example 280 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 8.89 (d, 1H, J = 6.
8Hz), 8.18 (d, 1H, J = 7.8Hz), 7.61 (s, 1H), 7.52 (d,
2H, J = 8.6Hz), 7.14 (d, 2H, J = 8.6Hz), 6.87 (t, 1H,
J = 7.3Hz), 3.85 (s, 3H), 2.53 (s, 3H), 2.09 (s, 3
H); MS (APCI, m / z): 424 (M + 1) +; HPLC (R): Rt. = 3.8 min. (Example 528) N- (6-hydroxy-pyridin-3-yl)- 2-methoxy-N- [4
-(6-Methyl 2-trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -acetamide 4.50 g of the compound of Example 265 (11.1.
Mmol) was dissolved in 30 ml of N, N-dimethylacetamide, 14.6 g (13.4 mmol) of methoxyacetyl chloride was added, and the mixture was stirred at room temperature for 2 hours. Further, 14.6 g (13.4 mmol) of methoxyacetyl chloride was added, ethyl acetate was added to the reaction solution, and the mixture was washed with a saturated aqueous solution of sodium hydrogen carbonate and a saturated saline solution. The organic layer was dried over anhydrous sodium sulfate, the solvent was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (dichloromethane: methanol = 20: 1) to give the title compound (230 m).
g and 1.60 g of the compound of Example 406 were obtained. mp 305-307 ° C; ¹ H-NMR (DMSO-d ₆ ) δ: 8.38 (s, 1H), 7.87 (s, 1H),
7.73 (d, 1H, J = 9.5Hz), 7.70-7.60 (m, 2H), 7.34 (d,
2H, J = 9.5Hz), 6.45 (d, 2H, J = 9.7Hz), 4.30-4.10 (b
r, 1H), 3.34 (s, 3H), 2.26 (s, 3H); MS (APCI, m / z): 464 (M + 1) +; HPLC (R): Rt. = 3.4 min. 529) 3- [2- (4-Methoxy-benzyl) -thiazol-4-yl] -6-methyl-2-trifluoromethylimidazo [1,2-α] pyridine 2-bromo-1- (6-methyl- 2-trifluoromethyl-imidazo
[1,2-α] pyridin-3-yl) -ethanone 177 mg (0.
55 mmol) and 100 mg (0.55 mmol) of (2- (4-methoxy-phenyl) -thioacetamide were dissolved in 40 ml of ethanol, and the mixture was heated under reflux for 15 hours. The organic layer was dried over anhydrous sodium sulfate, the solvent was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate / hexane = 1: 1) to give 147 mg (65%) of the title compound. ) Got.

¹ H-NMR (CDCl ₃ ) δ: 8.41 (s, 1H), 7.60
(d, 1H, J = 9.2Hz), 7.49 (s, 1H), 7.32 (d, 2H, J = 6.
5Hz), 7.17 (d, 1H, J = 9.2Hz), 6.93 (d, 2H, J = 8.6Hz),
4.37 (s, 2H), 3.82 (s, 3H), 2.33 (s, 3H); MS (APCI, m / z): 404 (M + 1) +; HPLC (R): Rt. = 5.9 min. Example 530) (3-Fluoro-4-methylphenyl)-[4- (6-methyl-2-trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -amine Using the compound of Reference Example 73 and the compound of (3-fluoro-4-methyl-phenyl) -thiourea (Reference Example 44), the same reaction as in Example 1 was carried out to obtain the title compound. 1H-NMR (DMSO-d6) δ: 10.57 (s, 1H), 8.54 (s, 1H),
7.71 (d, 1H, J = 3.8Hz), 7.67 (d, 1H, J = 7.8Hz), 7.40
(d, 1H, J = 9.5Hz), 7.31 (s, 1H), 7.19 (d, 1H, J = 8.1
Hz), 7.18 (s, 1H), 2.33 (s, 3H), 2.17 (s, 3H); MS (APCI, m / z): 407 (M + 1) +; HPLC (R): Rt. = 5.9 min. (Example 531) (6-Methylpyridin-3-yl)-[4- (6-methyl-2-trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl ] -Amine Using the compound of Reference Example 73 and the compound of (6-methyl-pyridin-3-yl) -thiourea (Reference Example 85), the same reaction as in Example 1 was carried out to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.54 (brs, 1H),
8.65 (d, 1H, J = 2.4Hz), 8.48 (s, 1H), 8.03 (dd, 1H,
J = 3.0Hz, 8.6Hz), 7.69 (d, 1H, J = 9.2Hz), 7.39 (d, 1
H, J = 9.5Hz), 7.31 (s, 1H), 7.20 (d, 1H, J = 8.4Hz),
2.40 (s, 3H), 2.33 (s, 3H); MS (APCI, m / z): 390 (M +
1) +; HPLC (R): Rt. = 3.1 min. (Example 532) 2- [2- (2-amino-ethoxy) -ethoxy] -N- [3- [2- (4-methoxy-phenyl) Amino) -thiazol-4-yl] -2-methylimidazo [1,2-α] pyridin-8-yl] -acetamide 2 trifluoroacetate 1) N- [4- (8-amino-2-methyl-) Imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -N- (4-methoxy-phenyl) -acetamide 729 mg (1.72 mmol) of the compound of Example 527
Was dissolved in 40 ml of methanol, and 1.69 g of zinc powder was dissolved.
(25.8 mmol) and the mixture was ice-cooled under a nitrogen stream. After 1.6 ml of acetic acid was added dropwise over 3 minutes, the mixture was refluxed for 6 hours. After the reaction solution was cooled to room temperature, it was filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was dissolved in 1-butanol, and washed with a saturated aqueous solution of sodium hydrogen carbonate and subsequently with a saturated saline solution. The organic layer solution is concentrated under reduced pressure, and the residue is subjected to silica gel column chromatography (dichloromethane: methanol =
10: 1) to give N- [4- (8-amino-2-methyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -N-
493 mg of (4-methoxy-phenyl) -acetamide (73
%).

MS (APCI, m / z): 394 (M + 1) +; HPLC (R): Rt. = 3.2 min. 2) N-acetyl-N- (2- [2-[(3- [ 2- [acetyl- (4-methoxy-phenyl) -amino] -thiazol-4-yl] -2-methyl
-Imidazo [1,2-α] pyridin-8-ylcarbamoyl) -methoxy] -ethoxy] -ethyl) -benzamide N- [4- (8-amino-2-methyl-imidazo [1,2 -
α] pyridin-3-yl) -thiazol-2-yl] -N- (4-methoxy-phenyl) -acetamide Example 532 1) 392
mg (1.00 mmol) and 440 mg (1.50 mmol) of [2- [2- (acetoxy-benzoyl-amino) -ethoxy] -ethoxy] -acetic acid dissolved in 8 ml of N, N-dimethylacetamide Was added with 0.8 ml of triethylamine. HATU (570 mg, 1.50 mmol) was added, and the mixture was stirred at 60 ° C. for 15 hours. Ethyl acetate was added to the reaction solution, and the mixture was washed with a saturated aqueous solution of sodium hydrogen carbonate and saturated saline. After drying the organic layer over anhydrous sodium sulfate,
The solvent was concentrated under reduced pressure, and 440 mg (1.50 mmol) of [2- [2- (acetoxy-benzoyl-amino) -ethoxy] -ethoxy] -acetic acid was again added to the obtained residue.
0.8 ml of triethylamine was added to the solution dissolved in 8 ml of N, N-dimethylacetamide. HATU 570mg
(1.50 mmol) and the mixture was stirred at 60 ° C. for 15 hours. Ethyl acetate was added to the reaction solution, and the mixture was washed with a saturated aqueous solution of sodium hydrogen carbonate and saturated saline. The organic layer is dried over anhydrous sodium sulfate, the solvent is concentrated under reduced pressure, the residue is purified by silica gel column chromatography (dichloromethane: methanol = 30: 1), and the obtained crystals are finely ground and washed with hexane-ethyl acetate. Compound 1
01 g was obtained.

MS (APCI, m / z): 669 (M + 1) +; HPLC (R): Rt. = 3.9 min. 3) 2- [2- (2-Amino-ethoxy) -ethoxy] -N -[3- [2-
(4-methoxy-phenylamino) -thiazol-4-yl] -2-
Methylimidazo [1,2-α] pyridin-8-yl] -acetamide 2 trifluoroacetate N-acetyl-N- (2- [2-[(3- [2- [acetyl- (4-methoxy-phenyl) ) -Amino] -thiazol-4-yl] -2-methyl-imidazo [1,2-α] pyridin-8-ylcarbamoyl) -methoxy]-
Ethoxy] -ethyl) -benzamide (1.00 g) was dissolved in methanol (30 ml) and tetrahydrofuran (15 ml), hydrazine monohydrate (1 ml) was added, and the mixture was heated under reflux for 1 hour. The reaction solution was concentrated under reduced pressure, and a mixed solvent of methanol and ethyl acetate was added to the obtained residue to dissolve phthalazide, followed by filtration.
The mother liquor was concentrated under reduced pressure, and the residue was purified by rover chromatography RP-8 (acetonitrile: water (containing 0.01% trifluoroacetic acid) = 70: 30) to give the title compound (590).
mg (81%, two steps). 1H-NMR (DMSO-d6) δ: 10.21 (s, 1H), 9.71 (s, 1H),
8.72 (d, 1H, J = 7.0Hz), 8.03 (d, 1H, J = 7.6Hz), 7.79
(brs, 1H), 7.54 (d, 2H, J = 8.9Hz), 7.09 (s, 1H), 7.0
3 (t, 1H, J = 7.0Hz), 6.93 (d, 2H, J = 8.9Hz), 4.28
(s, 2H), 3.81-3.67 (m, 6H), 3.73 (s, 3H), 3.05-3.0
0 (m, 2H), 2.57 (s, 3H); MS (APCI, m / z): 497 (M + 1) +; HPLC (R): Rt. = 2.7 min. (Example 533) 2-methoxy -N- (4-methoxy-phenyl) -N- [4- (6-methyl-2-trifluoromethylimidazo [1,2-α] pyridine-3-
Yl) -thiazol-2-yl] -acetamide The title compound was obtained by reacting the same compound as in Example 261 in the same manner as in Example 381. mp 205-207 ° C; 1H-NMR (DMSO-d6) δ: 8.25 (s, 1H), 7.63-7.56 (m, 4
H), 7.29 (dd, 2H, J = 1.6Hz, 9.2Hz), 7.10 (d, 2H, J =
8.9Hz), 4.00 (s, 2H), 3.81 (s, 3H), 3.31 (s, 3H),
2.19 (s, 3H); MS (APCI, m / z): 477 (M + 1) +; HPLC (R): Rt. = 5.0 min. (Example 534) Acetic acid [(4-methoxy-phenyl)- [4- (6-Methyl 2-trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -carbamoyl] -methyl ester Using the compound of Example 261 and acetoxyacetyl chloride The reaction was carried out in the same manner as in Example 381 to obtain the title compound. mp 218-220 ° C; 1H-NMR (DMSO-d6) δ: 8.25 (s, 1H), 7.66-7.60 (m, 4
H), 7.30 (dd, 2H, J = 1.6Hz, 9.2Hz), 7.13 (d, 2H, J =
8.9Hz), 4.60 (s, 2H), 3.81 (s, 3H), 2.20 (s, 3H),
2.13 (s, 3H); MS (APCI, m / z): 505 (M + 1) +; HPLC (R): Rt. = 5.2 min. (Example 535) 2-acetylamino N- [4- ( 6-chloro-2-methylimidazo
[1,2-α] pyridin-3-yl) -thiazol-2-yl] -N- (4
-Methoxy-phenyl) -acetamide Using the compound of Example 412, the reaction was carried out in the same manner as in Example 280 to obtain the title compound. mp 219-222 ° C; 1H-NMR (CDCl3) δ: 8.72 (dd, 1H, J = 0.8Hz, 2.2Hz),
7.43-7.28 (m, 3H), 7.16-7.03 (m, 4H), 4.06 (d, 2H,
J = 4.6Hz), 3.90 (s, 3H), 2.62 (s, 3H), 2.07 (s, 3
H); MS (APCI, m / z): 470 (M + 1) +; HPLC (R): Rt. = 2.9 min. (Example 536) 2-acetylamino N- (4-methoxy-phenyl)- N- [4- (6-
Methyl 2-trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -acetamide The compound of Example 438 was reacted in the same manner as in Example 280 to give the title compound. Obtained. mp 211-213 ° C; ¹ H-NMR (DMSO-d ₆ ) δ: 8.35-8.25 (m, 2H), 7.65-7.50
(m, 4H), 7.30 (d, 1H, J = 9.2Hz), 7.13 (d, 2H, J = 8.9H
z), 3.85-3.75 (m, 5H), 2.20 (s, 3H), 1.89 (s, 3H); MS (APCI, m / z): 504 (M + 1) +; HPLC (R): Rt. = 4.2 min. (Example 537) 2-acetylamino N- (6-methylpyridin-3-yl) -N- [4
-(6-Methyl 2-trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -acetamide Using the compound of Example 435, the reaction was carried out as in Example 280. This gave the title compound.

1H-NMR (DMSO-d6) δ: 8.74 (s, 1H), 8.3
5 (brs, 1H), 8.20 (s, 1H), 8.05 (d, 1H, J = 7.3Hz),
7.67 (s, 1H), 7.62 (d, 1H, J = 9.2Hz), 7.50 (d, 1H,
J = 8.1Hz), 7.31 (d, 1H, J = 9.4Hz), 3.80 (d, 2H, J = 4.
6Hz), 2.56 (s, 3H), 2.22 (s, 3H), 1.89 (s, 3H); MS (APCI, m / z): 489 (M + 1) +; HPLC (R): Rt. = 3.5 min. (Example 538) 2-acetylamino N- [4- (6-methyl-2-trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-
Yl] -N- (4-trifluoromethylphenyl) -acetamide Using the compound of Example 508, the reaction was carried out in the same manner as in Example 280 to obtain the title compound. mp 205-207 ° C; 1H-NMR (DMSO-d6) δ: 8.36 (t, 1H, J = 5.1Hz), 8.17
(s, 1H), 8.00 (d, 2H, J = 8.9Hz), 7.96 (d, 2H, J = 8.9
Hz), 7.68 (s, 1H), 7.61 (d, 1H, J = 9.4Hz), 7.29 (d
d, 1H, J = 1.6Hz, 9.4Hz), 3.79 (d, 2H, J = 5.7Hz), 2.1
7 (s, 3H), 1.88 (s, 3H); MS (APCI, m / z): 542 (M + 1) +; HPLC (R): Rt. = 4.6 min. (Example 539) Methylthiazol-2-yl)-[4- (6-methyl-2-trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -amine 2-amino-4-methyl Thiazole 23 mg (0.2
(0 mmol) was dissolved in 1.5 ml of acetone, and 29.6 μl (0.22 mmol) of benzoyl isothiocyanate was added, followed by stirring at room temperature for 22 hours. The reaction solution was concentrated under reduced pressure, and the obtained residue was dissolved in 1.5 ml of tetrahydrofuran. Water was added to the reaction solution, which was extracted with ethyl acetate. The organic phase was concentrated under reduced pressure, and the obtained residue was mixed with 1.5 ml of ethanol and 2-bromo-1- (6-methyl-2-trifluoro-imidazo [1,2-α] pyridin-3-yl) -ethanone ( Reference Example 73) 32 mg (0.10 mmol) was added and 4
Stir at 0 ° C. for 17 hours. The reaction solution was concentrated under reduced pressure, and the obtained residue was separated by HPLC (column Wakosil-II).
After purification by a gradient system of 5C18HG) and methanol-water (containing 0.01% trifluoroacetic acid), the solvent was concentrated under reduced pressure.
After dissolving in 5 ml, 100 mg (0.24 mmol, 2.43 mmol / g) of tris- (2-aminoethyl) -amine polystyrene HL resin was added, and the mixture was stirred at room temperature for 3 minutes. The reaction solution was filtered, and the filtrate was concentrated under reduced pressure. The obtained crystals were finely pulverized and washed with hexane-ethyl ether to obtain 6 mg of the title compound.

1H-NMR (DMSO-d6) δ: 9.11 (s, 1H), 7.9
7 (d, 1H, J = 8.9Hz), 7.72 (dd, 2H, J = 9.5Hz, 9.2Hz),
7.40 (d, 1H, J = 7.3Hz), 7.12 (s, 1H), 2.46 (s, 3
H), 2.32 (s, 3H); MS (APCI, m / z): 396 (M + 1) +; HPLC (R): Rt. = 4.9 min. (Example 540) [4- (6-methyl) 2-trifluoromethylimidazo [1,2-α]
Example 5 using pyridin-3-yl) -thiazol-2-yl]-(4-phenyl-thiazol-2-yl) -amine 2-amino-4-phenylthiazole
The reaction was carried out in the same manner as in Example 39 to obtain the title compound. 1H-NMR (DMSO-d6) δ: 8.54 (s, 1H), 8.01-7.84 (m, 2
H), 7.73-7.32 (m, 8H), 2.34 (s, 3H); MS (APCI, m / z): 458 (M + 1) +; HPLC (R): Rt. = 6.3 min. 541) [4- (5-methylthiophen-2-yl) -thiazol-2-yl]-
[4- (6-methyl-2-trifluoromethylimidazo [1,2-α]
Pyridin-3-yl) -thiazol-2-yl] -amine The reaction was carried out in the same manner as in Example 539 using 4- (5-methyl-thiophen-2-yl) -thiazol-2-ylamine to obtain the title compound. Was. 1H-NMR (DMSO-d6) δ: 8.54 (s, 1H), 7.71 (d, 1H, J =
8.9), 7.49 (s, 1H), 7.43-7.24 (m, 3H), 6.81 (dd, 1
H, 1.1Hz, 3.5Hz), 2.47 (s, 3H), 2.33 (s, 3H); MS (APCI, m / z): 478 (M + 1) +; HPLC (R): Rt. = 6.7 min Example 542 (4-methoxy-benzothiazol-2-yl)-[4- (6-methyl2
-Trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -amine The reaction was carried out in the same manner as in Example 539 using 4-methoxy-benzothiazol-2-ylamine. The compound was obtained. MS (APCI, m / z): 462 (M + 1) +; HPLC (R): Rt. = 5.8 min. (Example 543) [5- (4-tert-butyl-phenyl) -2-methyl2H -Pyrazole-
3-yl]-[4- (6-methyl-2-trifluoromethylimidazo
[1,2-α] pyridin-3-yl) -thiazol-2-yl] -amine As in Example 539 using 5-amino-3- (4-tert-butylphenyl) -1-methylpyrazole The reaction was performed to obtain the title compound. 1H-NMR (DMSO-d6) δ: 8.57 (s, 1H), 7.72-7.63 (m, 3
H), 7.42-7.38 (m, 3H), 7.33 (s, 1H), 6.85 (s, 1H),
3.81 (s, 3H), 2.32 (s, 3H), 1.29 (s, 9H); MS (APCI, m / z): 511 (M + 1) +; HPLC (R): Rt. = 6.6 min. Example 544) (2-Methyl-5-thiophen-2-yl-2H-pyrazol-3-yl)
-[4- (6-Methyl 2-trifluoromethylimidazo [1,2-α]
Pyridin-3-yl) -thiazol-2-yl] -amine The reaction was carried out in the same manner as in Example 539 using 5-amino-1-methyl-3- (thien-2-yl) pyrazole to obtain the title compound. . 1H-NMR (DMSO-d6) δ: 8.55 (s, 1H), 7.70 (d, 1H, J =
9.7Hz), 7.45-7.27 (m, 4H), 7.06 (dd, 1H, J = 3.8Hz,
5.1Hz), 6.80 (s, 1H), 3.79 (s, 3H), 2.31 (s, 3H); MS (APCI, m / z): 461 (M + 1) +; HPLC (R): Rt. = 5.0 min. (Example 545) (4-benzenesulfonylthiophen-3-yl)-[4- (6-methyl-2-trifluoromethylimidazo [1,2-α] pyridine-
3-yl) -thiazol-2-yl] -amine The reaction was carried out in the same manner as in Example 539 using 3-amino-4- (benzenesulfonylphenyl) thiophene to obtain the title compound.

MS (APCI, m / z): 521 (M + 1) +; HPLC (R): Rt. = 5.9 min. (Example 546) [4- (6-Methyl 2-trifluoromethylimidazo [ 1,2-α]
Pyridin-3-yl) -thiazol-2-yl]-(6-trifluoromethylpyridin-3-yl) -amine monohydrobromide The compound of Reference Example 73 and (6-trifluoromethyl-pyridine)
The reaction was carried out in the same manner as in Example 157 using (-3-yl) -thiourea (Reference Example 93) to obtain the title compound. 1H-NMR (DMSO-d6) δ: 11.2 (s, 1H), 8.88 (d, 1H, J =
2.4Hz), 8.44 (br s, 1H), 8.41 (d, 1H, J = 2.4Hz), 7.8
5 (d, 1H, J = 8.9Hz), 7.72 (d, 1H, J = 9.5Hz), 7.49
(s, 1H), 7.41 (dd, 1H, J = 1.6Hz, 9.5Hz), 2.33 (s, 3
H); MS (APCI, m / z): 444 (M + 1) +; HPLC (R): Rt. = 5.3 min. (Example 547) [5- (4-chlorophenyl) -2-methyl-2H -Pyrazol-3-yl]-[4- (6-methyl-2-trifluoromethyl-imidazo [1,2
-α] pyridin-3-yl) -thiazol-2-yl] -amine monohydrobromide Example 555 using 5- (4-chlorophenyl) -2-methyl-2H-pyrazol-3-ylamine The same reaction was carried out to obtain the title compound. 1H-NMR (DMSO-d6) δ: 8.56 (s, 1H), 7.76-7.68 (m, 3
H), 7.47-7.37 (m, 3H), 7.34 (s, 1H), 6.92 (s, 1H),
3.83 (s, 3H), 2.30 (s, 3H); MS (APCI, m / z): 489 (M + 1) +, 491 (M + 1) +; HPLC (R): Rt. = 5.9 min. Example 548 [4- (2,8-Dimethyl-imidazo [1,2-α] pyridin-3-yl)
-Thiazol-2-yl]-(6-trifluoromethylpyridine-
3-yl) -amine monohydrobromide The compound of Reference Example 1 and (6-trifluoromethyl-pyridine-3)
Example 1 using (-yl) -thiourea (Reference Example 93)
The reaction was carried out in the same manner as in 57 to give the title compound.

1H-NMR (DMSO-d6) δ: 11.3 (s, 1H), 8.9
6-8.91 (m, 2H), 8.38 (dd, 1H, J = 2.4Hz, 8.6Hz), 7.8
7 (d, 1H, J = 8.6Hz), 7.80 (d, 1H, J = 7.0), 7.65 (s,
1H), 7.47 (dd, 1H, J = 7.0Hz, 7.3Hz), 2.66 (s, 3H),
2.63 (s, 3H); MS (APCI, m / z): 390 (M + 1) +; HPLC (R): Rt. = 3.4 min. (Example 549) N- (4-methoxy-phenyl)- 2-methylamino-N- [4- (6-
Methyl 2-trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -acetamido dihydrochloride The compound was obtained. mp 203-206 ° C; ¹ H-NMR (DMSO-d ₆ ) δ: 9.40-9.20 (br, 1H), 8.24 (s,
1H), 7.73 (s, 1H), 7.65-7.55 (m, 3H), 7.31 (d, 1H,
J = 8.9Hz), 7.16 (d, 2H, J = 8.6Hz), 3.95-3.85 (br, 2
H), 3.83 (s, 3H), 2.60-2.50 (br, 3H), 2.20 (s, 3
H); MS (APCI, m / z): 476 (M + 1) +; HPLC (R): Rt. = 3.2 min. (Example 550) [4- (4-bromo-phenyl) -thiazole-2 -Yl]-[4- (6-methyl-2-trifluoromethylimidazo [1,2-α] pyridine-
3-yl) -thiazol-2-yl] -amine 1 trifluoroacetate 51 mg 2-amino-4- (4-bromophenyl) thiazole
(0.20 mmol) in 1.5 ml of acetone,
29.6 μl of benzoyl isothiocyanate (0.22
Mmol) and stirred at room temperature for 22 hours. The reaction solution was concentrated under reduced pressure, and the obtained residue was treated with tetrahydrofuran (1.5 m).
1N-aqueous solution of sodium hydroxide 1.0ml
Was added and stirred at 55 ° C. for 10 hours. Water was added to the reaction solution, which was extracted with ethyl acetate. The organic phase was concentrated under reduced pressure, and 1.5 ml of ethanol and 2-bromo-1- (6-methyl-2-ethanol) were added to the obtained residue.
32 mg (0.10 mmol) of trifluoro-imidazo [1,2-α] pyridin-3-yl) -ethanone (Reference Example 73) was added, and the mixture was stirred at 40 ° C. for 17 hours. The reaction solution was concentrated under reduced pressure, and the obtained residue was separated by HPLC (column Wakosil-
II5C18HG), methanol-water (0.01
% Trifluoroacetic acid) to afford the title compound.

MS (APCI, m / z): 536 (M + 1) +, 538 (M + 1) +; HPLC (R): Rt. = 7.3 min. (Example 551) [5- (5- Bromo-thiophen-2-yl) -thiazol-2-yl]
-[4- (6-Methyl 2-trifluoromethylimidazo [1,2-α]
Pyridin-3-yl) -thiazol-2-yl] -amine 1 trifluoroacetate The title compound obtained by performing a reaction in the same manner as in Example 550 using 2-amino-5- (5-bromothien-2-yl) thiazole. I got MS (APCI, m / z): 542 (M + 1) +, 544 (M + 1) +; HPLC (R): Rt. = 7.3 min. (Example 552) (5-tert-butyl-2- Methyl 2H-pyrazol-3-yl)-[4- (6
-Methyl 2-trifluoromethylimidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -amine 1 trifluoroacetate 5-amino-3-tert-butyl-1-methylpyrazole The reaction was carried out in the same manner as in Example 550 to obtain the title compound. MS (APCI, m / z): 435 (M + 1) +; HPLC (R): Rt. = 5.0 min. (Example 553) (2-methoxy-phenyl)-[4- (6-methyl2- Trifluoromethylimidazo [1,2-α] pyridin-3-yl) -1H-imidazol-2-yl] -amine 1 trifluoroacetate 2-bromo-1- (6-methyl-2-trifluoromethyl- Imidazo
[1,2-α] pyridin-3-yl) -ethanone 34.0 mg (0.
106 mmol) and 21.4 mg (0.106 mmol) of N- (2-methoxy-phenyl) -guanidine monohydrochloride are dissolved in 2.0 ml of ethanol and 44.0 mg of potassium carbonate are added.
mg (0.318 mmol) was added, and the mixture was heated under reflux for 14 hours. The reaction mixture was filtered using celite to remove insolubles, the solvent was concentrated under reduced pressure, and the obtained residue was finely pulverized and washed with hexane-ethyl acetate. The obtained crystals were separated by HPLC (column Wakosil-II5).
Purification by a gradient system of C18HG) and methanol-water (containing 0.01% trifluoroacetic acid) gave 6 mg (15%) of the title compound.

MS (APCI, m / z): 388 (M + 1) +; HPLC (R): Rt. = 3.1 min. (Example 554) (4-methoxy-phenyl)-[4- (6- Methyl 2-trifluoromethylimidazo [1,2-α] pyridin-3-yl) -1H-imidazol-2-yl] -amine 1 trifluoroacetate N- (4-methoxy-phenyl) -guanidine monohydrochloride The reaction was carried out in the same manner as in Example 553 to obtain the title compound. MS (APCI, m / z): 388 (M + 1) +; HPLC (R): Rt. = 3.1 min. (Example 555) (4-tert-butyl-thiazol-2-yl)-[4- (6-Methyl 2-trifluoromethylimidazo [1,2-α] pyridin-3-yl)-
Thiazol-2-yl] -amine monohydrobromide 2-amino-4-tert-butylthiazole 32 mg (0.20
Mmol) in 1.5 ml of acetone and 29.6 μl (0.22 mmol) of benzoyl isothiocyanate
Was added and stirred at room temperature for 22 hours. The reaction solution was concentrated under reduced pressure,
The obtained residue was dissolved in 1.5 ml of tetrahydrofuran, and 1.0 ml of a 1N aqueous solution of sodium hydroxide was added thereto.
Stirred at 5 ° C. for 10 hours. Water was added to the reaction solution, which was extracted with ethyl acetate. The organic phase was concentrated under reduced pressure, and the obtained residue was mixed with 1.5 ml of ethanol and 2-bromo-1- (6-methyl-2-trifluoro-imidazo [1,2-α] pyridin-3-yl) -ethanone ( Reference Example 73) 32 mg (0.10 mmol) was added and 40 ° C
For 17 hours. The reaction solution was concentrated under reduced pressure, and the obtained crystals were finely pulverized and then washed with hexane-ethyl acetate to obtain the title compound.

[0611] 1H-NMR (DMSO-d6) δ: 8.53 (s, 1H), 7.7
0 (d, 1H, J = 9.7Hz), 7.41-7.37 (m, 2H), 6.62 (s, 1
H), 2.32 (s, 3H), 1.31 (s, 9H); MS (APCI, m / z): 438 (M + 1) +; HPLC (R): Rt. = 6.7 min. (Example 556) [4- (2,8-dimethyl-imidazo [1,2-α] pyridin-3-yl)-
1H-Imidazol-2-yl]-(4-methoxy-phenyl) -amine 3-trifluoroacetate Example 553 using N- (4-methoxy-phenyl) -guanidine monohydrochloride and the compound of Reference Example 1 The title compound was obtained by the same reaction. 1H-NMR (DMSO-d6) δ: 8.80 (br s, 1H), 7.63 (d, 1H,
J = 6.8Hz), 7.58-7.53 (m, 3H), 7.31 (br t, 1H, J = 6.8
Hz), 7.17 (d, 2H, J = 8.9Hz), 3.85 (s, 3H), 2.59 (s,
3H), 2.54 (s, 3H); MS (APCI, m / z): 334 (M + 1) +; HPLC (R): Rt. = 2.2 min. (Example 557) [4- (2,6 -Dimethyl-imidazo [1,2-α] pyridin-3-yl)
-Thiazol-2-yl]-(6-methoxy-pyridin-3-yl)-
Carbamic acid isobutyl ester [4- (2,6-dimethyl-imidazo [1,2-α] pyridin-3-yl)-
Thiazol-2-yl]-(6-methoxy-pyridin-3-yl) -amine hydrobromide (Example 307) and isobutyl chloroformate were reacted in the same manner as in Example 301 to give the title compound. I got mp 148-150 ° C; 1H-NMR (CDCl3) δ: 8.44 (br s, 1H), 8.22 (dd, 1H,
J = 0.8Hz, 3.0Hz), 7.59 (dd, 1H, J = 2.7Hz, 8.9Hz), 7.
40 (d, 1H, J = 8.9Hz), 7.01 (s, 1H), 6.95 (dd, 1H, J
= 1.9Hz, 8.9Hz), 6.90 (dd, 1H, J = 0.8Hz, 8.9Hz), 4.0
7 (d, 2H, J = 6.5Hz), 4.01 (s, 3H), 2.59 (s, 3H), 2.
13 (s, 3H), 1.94 (sep, 1H, J = 6.5Hz), 0.86 (d, 6H, J
= 6.8 Hz); MS (APCI, m / z): 452 (M + H) +; HPLC (R): Rt. = 3.8 min. (Example 558) (4-methoxy-phenyl)-[4- ( 6-methyl-2-trifluoromethyl-imidazo [1,2-α] pyridin-3-yl) -thiazole
2-yl] -amine monohydrobromide Using the compound of Reference Example 73 and (4-methoxy-phenyl) -thiourea (Reference Example 3), the reaction was carried out in the same manner as in Example 157, and the title compound was obtained. Obtained.

[0612] ¹ H-NMR (DMSO-d ₆ ) δ: 10.31 (brs, 1H),
8.52 (d, 1H, J = 1.4Hz), 7.69 (d, 1H, J = 3.6Hz), 7.55
(dt, 2H, J = 2.2Hz, 8.9Hz), 7.39 (dd, 1H, J = 1.9Hz,
9.5Hz), 7.20 (s, 1H), 6.91 (dt, 2H, J = 2.2Hz, 8.9H
z), 4.38 (s, 3H), 3.72 (s, 3H); MS (APCI, m / z): 405 (M + 1) +; HPLC (R): Rt. = 5.3 min. (Example 559) (2,5-dimethyl-2H-pyrazol-3-yl)-[4- (6-methyl-2
-Trifluoromethyl-imidazo [1,2-α] pyridine-3-i
L) -Thiazol-2-yl] -amine monohydrobromide Example 5 using 5-amino-1,3-dimethylpyrazole
The reaction was carried out in the same manner as for 55 to give the title compound. 1H-NMR (DMSO-d6) δ: 8.50 (s, 1H), 7.69 (d, 1H, J =
9.1Hz), 7.39 (d, 1H, J = 9.1Hz), 7.30 (s, 1H), 6.24
(s, 1H), 3.69 (s, 3H), 2.33 (s, 3H), 2.12 (s, 3H); MS (APCI, m / z): 393 (M + 1) +; HPLC (R): Rt = 4.1 min. (Example 560) (2-methyl-2H-pyrazol-3-yl)-[4- (6-methyl-2-to
Trifluoromethyl-imidazo [1,2-α] pyridin-3-yl)-
Thiazol-2-yl] -amine monohydrobromide Example 555 using 5-amino-1-methylpyrazole
The reaction was carried out in the same manner as in to give the title compound. 1H-NMR (DMSO-d6) δ: 10.5 (br s, 1H), 8.47 (s, 1
H), 7.69 (d, 1H, J = 9.2Hz), 7.41-7.36 (m, 2H), 7.30
(s, 1H), 6.41 (s, 1H), 3.77 (s, 3H), 2.32 (s, 3H); MS (APCI, m / z): 379 (M + 1) +; HPLC (R): Rt = 4.0 min. (Example 561) (5-cyclopropyl-2-methyl-2H-pyrazol-3-yl)-
[4- (6-methyl-2-trifluoromethyl-imidazo [1,2-α]
Pyridin-3-yl) -thiazol-2-yl] -amine monobromide
5-cyclopropyl-2-methyl-2H-pyrazol-3-ylaminate
The title compound was reacted in the same manner as in Example 555 using
I got

1H-NMR (DMSO-d6) δ: 8.50 (s, 1H), 7.6
9 (d, 1H, J = 9.3Hz), 7.40 (d, 1H, J = 9.3Hz), 7.31 (s,
1H), 6.19 (s, 1H), 3.68 (s, 3H), 2.33 (s, 3H), 1.
81 (m, 1H), 0.89-0.82 (m, 2H), 0.64-0.60 (m, 2H); MS (APCI, m / z): 419 (M + 1) +; HPLC (R): Rt. = 4.5 min. (Example 562) N- [4- (2,6-dimethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -2-isopropoxy-N- ( 6-methoxy-pyridin-3-yl) -acetamide [4- (2,6-dimethyl-imidazo [1,2-α] pyridin-3-yl)-
Thiazol-2-yl]-(6-methoxy-pyridin-3-yl) -amine hydrobromide (Example 307) and isopropoxyacetic acid were used to carry out the reaction in the same manner as in Example 563 to give the title compound. I got 1H-NMR (CDCl3) δ 8.38 (s, 1H), 8.25 (d, 1H, J = 2.7
Hz), 7.63 (dd, 1H, J = 2.7Hz, 8.6Hz), 7.38 (d, 1H, J
= 9.5Hz), 7.05 (s, 1H), 6.95 (dd, 2H, J = 3.0Hz, 8.9H
z), 4.08 (s, 2H), 4.03 (s, 3H), 3.71-3.60 (m, 1H),
2.58 (s, 3H), 2.13 (s, 3H), 1.17 (d, 6H, J = 5.9 Hz); MS (APCI, m / z): 452 (M + 1) +; HPLC (R): Rt. = 3.4 min. (Example 563) N- [4- (2,6-dimethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -2-isobutoxy-N- ( 6-Methoxy-pyridin-3-yl) -acetamide 819 mg (6.2 mmol) of isobutoxyacetic acid was dissolved in 5 ml of benzene, and 5 ml of thionyl chloride was added thereto.
Stirred at C for 1 hour. The reaction solution was concentrated under reduced pressure, and the resulting residue was dissolved in 15 ml of N, N-dimethylacetamide under a nitrogen stream.

[4- (2,6-Dimethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl]-(6-methoxy-pyridin-3-yl) -amine bromide Hydrochloride (Example 307)
After adding 34 g (3.10 mmol), 1 ml of triethylamine was added dropwise over 3 minutes. A catalytic amount of 4-pyrrolidinopyridine was added, and the mixture was stirred at room temperature for 4 days. Ethyl acetate was added to the reaction solution, and the mixture was washed with a saturated aqueous solution of sodium hydrogen carbonate and saturated saline. After the organic layer was dried over anhydrous sodium sulfate, the solvent was concentrated under reduced pressure. The obtained residue was purified by flash chromatography (ethyl acetate), and the obtained crystals were finely pulverized and washed with hexane-ethyl acetate to obtain 513 mg (36%) of the title compound.

Mp 186-188 ° C .; 1H-NMR (CDCl3) δ 8.38 (d, 1H, J = 0.8 Hz), 8.24 (d,
1H, J = 2.7Hz), 7.63 (dd, 1H, J = 2.7Hz, 8.9Hz), 7.38
(d, 1H, J = 8.9Hz), 7.05 (s, 1H), 6.94 (dt, 2H, J = 1.
9Hz, 8.9Hz), 4.09 (s, 2H), 4.02 (s, 3H), 3.29 (d,
2H, J = 6.8Hz), 2.58 (s, 3H), 2.13 (s, 3H), 1.91 (se
p, 1H, J = 6.8Hz), 0.92 (d, 6H, J = 6.8Hz); MS (APCI, m / z): 466 (M + 1) +; HPLC (R): Rt. = 3.7 min. (Example 564) 2-benzyloxy-N- [4- (2,6-dimethyl-imidazo [1,1
2-α] pyridin-3-yl) -thiazol-2-yl] -N- (6-methoxy-pyridin-3-yl) -acetamide [4- (2,6-dimethyl-imidazo [1,2-α ] Pyridin-3-yl)-
Thiazol-2-yl]-(6-methoxy-pyridin-3-yl) -amine hydrobromide (Example 307) 1.00 g (2.3
(1 mmol) was dissolved in 10 ml of N, N-dimethylacetamide and 350 μl of triethylamine under a nitrogen stream. 4-
After adding a catalytic amount of pyrrolidinopyridine, benzyloxy
-Acetyl chloride 547 μl (3.47 mmol)
Was added and stirred at room temperature for 8 hours. Triethylamine 350
μl and benzyloxy-acetyl chloride 547 μl
(3.47 mmol), and the mixture was stirred at room temperature for 15 hours. Then, 350 μl of triethylamine and 547 μl (3.47 mmol) of benzyloxy-acetyl chloride were added, and the mixture was stirred for 2 hours. Ethyl acetate was added to the reaction solution, and the mixture was washed with a saturated aqueous solution of sodium hydrogen carbonate, water, and saturated saline. After the organic layer was dried over anhydrous sodium sulfate, the solvent was concentrated under reduced pressure. The obtained crystals were finely ground and washed with hexane-ethyl acetate to give 1.07 g of the title compound.
(93%).

1H-NMR (CDCl3) δ: 8.36 (s, 1H), 8.21
(d, 1H, J = 2.7Hz), 7.57 (dd, 1H, J = 8.9Hz, 2.7Hz),
7.40-7.20 (m, 5H), 7.06 (s, 1H), 6.96-6.89 (m, 2
H), 4.65 (s, 2H), 4.12 (s, 2H), 4.01 (s, 3H), 2.58
(s, 3H), 2.12 (s, 3H); MS (APCI, m / z): 500 (M + 1) +; HPLC (R): Rt. = 3.7 min. (Example 565) N- [4 -(2,6-Dimethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -N- (6-methoxy-pyridin-3-
Yl) -2-phenoxy-acetamide [4- (2,6-dimethyl-imidazo [1,2-α] pyridin-3-yl)-
Thiazol-2-yl]-(6-methoxy-pyridin-3-yl) -amine hydrobromide (Example 307) and the same reaction as in Example 564 using phenoxy-acetyl chloride. The compound was obtained. 1H-NMR (CDCl3) δ: 8.37 (s, 1H), 8.32 (d, 1H, J = 2.7
Hz), 7.69 (dd, 1H, J = 8.9Hz, 2.7Hz), 7.39 (d, 1H,
8.9Hz), 7.34-7.24 (m, 2H), 7.07 (s, 1H), 7.05-6.93
(m, 3H), 6.87 (m, 2H), 4.67 (s, 2H), 4.03 (s, 3
H), 2.58 (s, 3H), 2.13 (s, 3H); MS (APCI, m / z): 486 (M + 1) +; HPLC (R): Rt. = 3.7 min. (Example 566) N- [4- (2,6-dimethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -N- (6-methoxy-pyridin-3-
Yl) -2- (3,4,5-trimethoxy-benzoyloxy) -acetamide [4- (2,6-dimethyl-imidazo [1,2-α] pyridin-3-yl)-
Thiazol-2-yl]-(6-methoxy-pyridin-3-yl) -amine hydrobromide (Example 307) and 3,4,5-trimethoxybenzyl alcohol as in Example 567 The title compound was obtained by carrying out the reaction.

MS (APCI, m / z): 590 (M + 1) +; HPLC (R): Rt. = 3.5 min. (Example 567) N- [4- (2,6-dimethyl-imidazo [ 1,2-α] pyridin-3-yl) -thiazol-2-yl] -N- (6-methoxy-pyridin-3-
Yl) -2- (thiophen-2-ylmethoxy) -acetamide Under a nitrogen stream, sodium hydride, oily (containing 55%)
2.35 g (53.8 mmol) was washed twice with 20 ml of hexane, dried, and suspended in 80 ml of tetrahydrofuran. 2.1 ml of 2-thiophene methanol at room temperature
(21.6 mmol) was added dropwise over 3 minutes and stirred for 1 hour. The reaction vessel was ice-cooled and 3.00 g of bromoacetic acid (2
(1.6 mmol) and the mixture was stirred at 60 ° C. for 1.5 hours. Further, an aqueous hydrochloric acid solution was added to adjust the pH to 3. The reaction solution was extracted with ethyl acetate, and the organic phase was washed with saturated saline. After the organic layer was dried over anhydrous sodium sulfate, the solvent was concentrated under reduced pressure to obtain unpurified (thiophen-2-ylmethoxy) acetic acid 4.06.
g was obtained.

Unpurified (thiophen-2-ylmethoxy)
In a nitrogen stream, 34 mg of acetic acid was dissolved in 1 ml of N, N-dimethylacetamide, and [4- (2,6-dimethyl-imidazo [1,2-
α] pyridin-3-yl) -thiazol-2-yl]-(6-methoxy
-Pyridin-3-yl) -amine hydrobromide (Example 30)
7) 43 mg (0.1 mmol), a catalyst amount of 4-pyrrolidinopyridine and 0.1 ml of triethylamine were added. HA
660 mg (1.73 mmol) of TU was added, and the mixture was stirred at room temperature for 15 hours. Ethyl acetate was added to the reaction solution, and the mixture was washed with a saturated aqueous solution of sodium hydrogen carbonate and saturated saline. After the organic layer was dried over anhydrous sodium sulfate, the solvent was concentrated under reduced pressure, and the residue was purified by preparative thin-layer chromatography (dichloromethane / methanol = 10: 1.) To give the title compound (37 mg, 7%).
3%).

MS (APCI, m / z): 506 (M + 1) +; HPLC (R): Rt. = 3.7 min. (Example 568) Acetic acid [[4- (2,6-dimethyl-imidazo [ 1,2-α] pyridine-3
-Yl) -thiazol-2-yl]-(6-methoxy-pyridine-3-
Yl) -carbamoyl]-(S) -ethyl ester [4- (2,6-dimethyl-imidazo [1,2-α] pyridin-3-yl)-
Example 382 using thiazol-2-yl]-(6-methoxy-pyridin-3-yl) -amine hydrobromide (Example 307) and (S)-(-)-2-acetoxypropionic acid. The title compound was obtained by carrying out a reaction in the same manner as in. MS (APCI, m / z): 466 (M + 1) +; HPLC (R): Rt. = 3.4 min. (Example 569) 2-benzylamino-N- [4- (2,6-dimethyl- Imidazo [1,2
-α] pyridin-3-yl) -thiazol-2-yl] -N- (6-methoxy-pyridin-3-yl) -acetamide [4- (2,6-dimethyl-imidazo [1,2-α] (Pyridin-3-yl)-
Thiazol-2-yl]-(6-methoxy-pyridin-3-yl) -amine hydrobromide (Example 307) was reacted with benzylamine in the same manner as in Example 515 to give the title compound. Obtained. MS (APCI, m / z): 499 (M + 1) +; HPLC (R): Rt. = 2.6 min. (Example 570) 2- (benzyl-methyl-amino) -N- [4- (2 , 6-Dimethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl]
-N- (6-Methoxy-pyridin-3-yl) -acetamide [4- (2,6-dimethyl-imidazo [1,2-α] pyridin-3-yl)-
Thiazol-2-yl]-(6-methoxy-pyridin-3-yl) -amine hydrobromide (Example 307) and benzyl-methyl-
The title compound was obtained by carrying out a reaction in the same manner as in Example 515 using an amine.

MS (APCI, m / z): 513 (M + 1) +; HPLC (R): Rt. = 2.6 min. (Example 571) 2- (acetyl-methyl-amino) -N- [4 -(2,6-Dimethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl]
-N- (6-Methoxy-pyridin-3-yl) -acetamido N- [4- (2,6-dimethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl]- N- (6-methoxy-pyridine-3-
Yl) -2-methylamino-acetamide (Example 575)
21 mg (50 μmol) of dichloromethane 1.5
The solution was dissolved in acetyl chloride (35 ml), and the mixture was stirred at room temperature for 2.5 hours. Ethyl acetate was added to the reaction solution, and a saturated aqueous solution of sodium hydrogen carbonate, water,
Washed with saturated saline. After the organic layer was dried over anhydrous sodium sulfate, the solvent was concentrated under reduced pressure. The residue obtained was ground finely and washed with hexane-ethyl acetate to give the title compound 1
7 mg (74%) were obtained. 1H-NMR (CDCl3) δ: 8.39 (s, 1H), 8.31 (d, 1H, J = 2.4
Hz), 7.75 (dd, 1H, J = 8.6Hz, 2.4Hz), 7.39 (d, 1H,
9.2Hz), 7.05 (s, 1H), 6.98-6.93 (m, 2H), 4.16-4.00
(br s, 2H), 4.01 (s, 3H), 3.18 (s, 3H), 2.58 (s,
3H), 2.17 (s, 3H), 2.13 (s, 3H); MS (APCI, m / z): 465 (M + 1) +; HPLC (R): Rt. = 2.9 min. (Example 572) N- [4- (2,6-dimethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -N- (6-methoxy-pyridin-3-
Yl) -2- (2-thiophen-2-yl-ethylamino) -acetamide [4- (2,6-dimethyl-imidazo [1,2-α] pyridin-3-yl)-
Thiazol-2-yl]-(6-methoxy-pyridin-3-yl) -amine hydrobromide (Example 307) and 2-thiophen-2-
The title compound was obtained by carrying out the reaction in the same manner as in Example 515 using yl-ethylamine.

MS (APCI, m / z): 519 (M + 1) +; HPLC (R): Rt. = 2.7 min. (Example 573) N- [4- (2,6-dimethyl-imidazo [ 1,2-α] pyridin-3-yl) -thiazol-2-yl] -N- (6-methoxy-pyridin-3-
Yl) -2- (2-morpholin-4-yl-ethylamino) -acetamide [4- (2,6-dimethyl-imidazo [1,2-α] pyridin-3-yl)-
Thiazol-2-yl]-(6-methoxy-pyridin-3-yl) -amine hydrobromide (Example 307) and 2-morpholin-4-
The title compound was obtained by carrying out the reaction in the same manner as in Example 515 using yl-ethylamine. MS (APCI, m / z): 522 (M + 1) +; HPLC (R): Rt. = 2.2 min. (Example 574) [[[4- (2,6-dimethyl-imidazo [1,2 -α] pyridin-3-yl) -thiazol-2-yl]-(6-methoxy-pyridin-3-yl) -carbamoyl] -methyl] -carbamic acid-2-methoxy
-Ethyl ester 2-amino-N- [4- (2,6-dimethyl-imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -N- (6-methoxy-pyridine- 3-yl) -acetamide trihydrochloride (Example 37
8) To 400 mg (0.77 mmol), a saturated aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with ethyl acetate. After washing the organic phase with saturated saline, the organic layer was dried over anhydrous sodium sulfate and the solvent was concentrated under reduced pressure to obtain 240 mg of a free form of Example 378. This was dissolved in 5 ml of tetrahydrofuran, 100 μl of diisopropylethylamine and a catalytic amount of 4-dimethylaminopyridine were added, and 81 m of 2-methoxyethoxychloroformate was added.
g (0.59 mmol) was added and the mixture was stirred at room temperature for 3 hours.
Ethyl acetate was added to the reaction solution, and the mixture was washed with a saturated aqueous solution of sodium hydrogen carbonate and saturated saline. After the organic layer was dried over anhydrous sodium sulfate, the solvent was concentrated under reduced pressure, and the residue was subjected to flash chromatography (dichloromethane / methanol = 2).
0: 1.) to give 290 mg of the title compound.

MS (APCI, m / z): 511 (M + 1) +; HPLC (R): Rt. = 3.0 min. (Example 575) N- [4- (2,6-dimethyl-imidazo [ 1,2-α] pyridin-3-yl) -thiazol-2-yl] -N- (6-methoxy-pyridin-3-
Using yl) -2-methylamino-acetamide (tert-butoxycarbonyl-methyl-amino) -acetic acid and the compound of Example 307, the reaction was carried out in the same manner as in Example 405 to obtain the title compound. 1H-NMR (CDCl3) δ: 8.38 (s, 1H), 8.24 (d, 1H, J = 2.7
Hz), 7.62 (dd, 1H, J = 8.6Hz, 2.7Hz), 7.38 (d, 1H,
9.2Hz), 7.05 (s, 1H), 6.98-6.92 (m, 2H), 4.02 (s, 3
H), 3.36 (s, 2H), 2.59 (s, 3H), 2.45 (s, 3H), 2.13
(s, 3H); MS (APCI, m / z): 423 (M + 1) +; HPLC (R): Rt. = 2.1 min. (Example 576) N- [4- (2,6-dimethyl) -Imidazo [1,2-α] pyridin-3-yl) -thiazol-2-yl] -N- (6-methoxy-pyridin-3-
Yl) -2- [methyl- (thiophen-2-sulfonyl) -amino]-
Acetamide Using the compound of Example 575 and thiophen-2-sulfonyl chloride, the reaction was carried out in the same manner as in Example 128 (using only pyridine as the solvent) to obtain the title compound. MS (APCI, m / z): 569 (M + 1) +; HPLC (R): Rt. = 3.4 min. (Example 577) N- [4- (2,6-dimethyl-imidazo [1,2] -α] pyridin-3-yl) -thiazol-2-yl] -N- (6-methoxy-pyridin-3-
Yl) -2- [Methyl- (toluene-4-sulfonyl) -amino] -acetamide Reaction as in Example 128 using the compound of Example 575 and p-toluenesulfonyl chloride (only pyridine was used as the solvent) To give the title compound. MS (APCI, m / z): 577 (M + 1) +; HPLC (R): Rt. = 3.8 min. (Example 578) N- [4- (2,6-dimethyl-imidazo [1,2] -α] pyridin-3-yl) -thiazol-2-yl] -N- (6-methoxy-pyridin-3-
Yl) -2- [methyl- (propane-1-sulfonyl) -amino] -acetamide Same as example 128 using the compound of example 575 and propane-1-sulfonyl chloride (solvent only using pyridine) The reaction was performed to obtain the title compound. MS (APCI, m / z): 529 (M + 1) +; HPLC (R): Rt. = 3.5 min. (Example 579) N-[[[4- (2,6-dimethyl-imidazo [1 , 2-α] pyridine-3-
Yl) -thiazol-2-yl]-(6-methoxy-pyridin-3-yl) -carbamoyl] -methyl] -N-methyl-benzamide Same as example 128 using the compound of example 575 and benzoyl chloride ( The reaction was carried out using only dichloromethane as a solvent to obtain the title compound.

MS (APCI, m / z): 527 (M + 1) +; HPLC (R): Rt. = 3.4 min. (Example 580) Furan-2-carboxylic acid [[[4- (2, 6-dimethyl-imidazo [1,
2-α] pyridin-3-yl) -thiazol-2-yl]-(6-methoxy-pyridin-3-yl) -carbamoyl] -methyl] -methyl-
Amide Using the compound of Example 575 and furan-2-carbonyl chloride, the reaction was carried out in the same manner as in Example 128 (using only dichloromethane as the solvent) to obtain the title compound. MS (APCI, m / z): 517 (M + 1) +; HPLC (R): Rt. = 3.2 min. (Example 581) Hexadecanoic acid [[[4- (2,6-dimethyl-imidazo [1 , 2-α]
Pyridin-3-yl) -thiazol-2-yl]-(6-methoxy-pyridin-3-yl) -carbamoyl] -methyl] -methyl-amide Using the compound of Example 575 and palmitoyl chloride, Same (only pyridine was used as solvent)
To give the title compound. MS (APCI, m / z): 661 (M + 1) +; HPLC (R): Rt. = 6.3 min. (Example 582) N- [4- (2,6-dimethyl-imidazo [1,2] -α] pyridin-3-yl) -thiazol-2-yl] -2- (formyl-methyl-amino)-
N- (6-Methoxy-pyridin-3-yl) -acetamide 4.3 ml of formic acid was added to 10 ml of acetic anhydride, and the mixture was stirred at 60 ° C. for 2 hours. 2 ml of the reaction solution was mixed with 15 mg (36 μmol) of the compound of Example 579 in 3 ml of dichloromethane.
The solution was added and stirred at room temperature for 20 hours. Ethyl acetate was added to the reaction solution, and the mixture was washed with a saturated aqueous solution of sodium hydrogen carbonate and saturated saline. After the organic layer was dried over anhydrous sodium sulfate, the solvent was concentrated under reduced pressure, and the residue was purified by flash chromatography (dichloromethane / methanol = 15: 1.) To obtain 14 mg of the title compound.

MS (APCI, m / z): 451 (M + 1) +; HPLC (R): Rt. = 2.8 min. (Example 583) [Example: [4- (2,6-dimethyl-imidazo [1, 2-α] pyridin-3-yl)
-Thiazol-2-yl]-(4-methoxyphenyl) -carbamic acid isobutyl ester [4- (2,6-dimethyl-imidazo [1,2-α] pyridin-3-yl)-
The title compound was obtained by carrying out a reaction in the same manner as in Example 301 using thiazol-2-yl]-(4-methoxyphenyl) -amine hydrobromide (Example 57) and isobutyl chloroformate. 1H-NMR (DMSO-d ₆ ) δ: 8.41 (br s, 1H), 7.43 (dt, 2
H, J = 2.2Hz, 8.9Hz), 7.38 (s, 1H), 7.35 (d, 1H, J =
9.2Hz), 7.08 (dt, 2H, J = 2.2Hz, 8.9Hz), 7.01 (dd, 1
H, J = 2.2Hz, 9.2Hz), 4.00 (d, 2H, J = 6.2Hz), 3.81
(s, 3H), 2.46 (s, 3H), 2.02 (s, 3H), 1.99-1.93 (m,
1H), 0.78 (d, 6H, J = 6.5Hz); MS (APCI, m / z): 451 (M + H) +; HPLC (R): Rt. = 4.2 min. (Reference Example 1) 2- Bromo-1- (2,8-dimethyl-imidazo [1,2-α] pyridine-
3-yl) -ethanone (1) 1- (2,8-dimethyl-imidazo [1,2-α] pyridine-3-
649 mg (6.00 mmol) of 3-yl-ethanone 3-methyl-pyridin-2-ylamine, 0.93 ml of 3-chloro-pentane-2,4-dione
(7.80 mmol) and 514 mg of sodium bicarbonate
(6.12 mmol) was suspended in 8 ml of dimethoxyethane and heated under reflux for 19 hours. After cooling, the reaction solution was diluted with ethyl acetate and washed with water and saturated saline. After the organic layer was dried over anhydrous sodium sulfate, the solvent was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (dichloromethane / methanol = 10: 1) to give 1- (2,8-dimethyl-
717 mg of imidazo [1,2-α] pyridin-3-yl) -ethanone
(63%).

1H-NMR (CDCl3) δ: 9.61 (d, 1H, J = 6.8H
z), 7.24 (d, 1H, J = 7.0Hz), 6.93 (t, 1H, J = 7.0Hz),
2.82 (s, 3H), 2.64 (s, 3H), 2.63 (s, 3H); MS (APCI, m / z): 189 (M + H) +; HPLC (N): Rt = 1.8 min. (2 ) 2-Bromo-1- (2,8-dimethyl-imidazo [1,2-α] pyridin-3-yl) -ethanone 1- (2,8-dimethyl-imidazo [1,2-α] pyridine-3 -Il)-
715 mg (3.80 mmol) of ethanone was dissolved in 5 ml of 47% hydrobromic acid and heated to 70 ° C., followed by 196 μl of bromine.
(3.80 mmol) of a 48% solution of hydrobromic acid in 5 ml was added dropwise over 40 minutes. The reaction solution was concentrated under reduced pressure, a saturated aqueous sodium hydrogen carbonate solution was added to the obtained residue, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over anhydrous sodium sulfate, and the solvent was concentrated under reduced pressure. The obtained crude crystals were pulverized finely and washed with hexane-ethyl acetate to obtain 619 mg (61%) of the title compound. 1H-NMR (CDCl3) δ: 9.59 (d, 1H, J = 6.5Hz), 7.32 (d,
1H, J = 7.0Hz), 6.99 (t, 1H, J = 7.3Hz), 4.38 (s, 2H),
2.89 (s, 3H), 2.66 (s, 3H); MS (APCI, m / z): 267 (M + H) +, 269 (M + H) +; HPLC (N): Rt = 2.2 min. Reference Example 2) (4-trifluoromethyl-phenyl) -thiourea (1) Benzoyl-3- (4-trifluoromethyl-phenyl)
-Thiourea 8.86 g (55.0 mmol) of 4-trifluoromethylaniline was dissolved in 200 ml of acetone, 7.39 ml (55.0 mmol) of benzoylisothiocyanate was added, and the mixture was stirred at room temperature for 3 days. The reaction solution was concentrated under reduced pressure, and the obtained crystals were finely pulverized, washed with hexane-ethyl ether, and 14.2 g (79%) of benzoyl-3- (4-trifluoromethyl-phenyl) -thiourea was obtained as a colorless powder. Obtained.

1H-NMR (CDCl3) δ: 12.84 (s, 1H), 9.13
(s, 1H), 7.95-7.89 (m, 4H), 7.72-7.66 (m, 3H), 7.
60-7.54 (m, 2H), 4.37 (s, 2H), 2.85 (s, 3H), 2.42
(s, 3H); MS (FAB, m / z): 325 (M + H) +. (2) (4-trifluoromethyl-phenyl) -thiourea benzoyl-3- (4-trifluoromethyl-phenyl) -Tiourea (14.2 g, 43.5 mmol) was dissolved in tetrahydrofuran (200 ml), and sodium hydroxide (5.24 g) was dissolved.
(131 mmol) dissolved in 10 ml of water,
Stirred at 60 ° C. for 2 hours. Again sodium hydroxide 5.2
A solution of 4 g (131 mmol) in 10 ml of water was added, and the mixture was stirred at 60 ° C for 8 hours. After cooling, ethyl acetate was added to the reaction solution, which was washed with water and saturated saline. The organic layer was dried over anhydrous sodium sulfate, the solvent was concentrated under reduced pressure, and the obtained crude crystals were finely pulverized and washed with hexane-ethyl ether to obtain 8.97 g (95%) of the title compound as a colorless powder. .

1H-NMR (CDCl3) δ: 8.47 (brs, 1H), 7.71
(d, 2H, J = 8.6Hz), 7.39 (d, 2H, J = 8.6Hz), 6.28 (br
s, 2H); MS (APCI, m / z): 221 (M + H) +; HPLC (N): Rt = 3.5 min. (Reference Example 3) (4-methoxy-phenyl) -thiourea 4-methoxyaniline 15.0 g (94.0 mmol) of the hydrochloride were added to a solution of 10.0 g (132 mmol) of ammonium thiocyanate in 5 ml of water and stirred at 90 ° C. for 14 hours. The reaction solution was filtered, and the obtained crystals were finely pulverized, washed with ethanol, and then washed with 3.71 g of the title compound (22
%) As a colorless powder.

1H-NMR (DMSO-d6) δ: 9.46 (s, 1H), 7.4
0-7.10 (m, 2H), 7.22 (d, 2H, J = 8.9Hz), 6.90 (d, 2
H, J = 8.9Hz), 3.33 (s, 3H); MS (EI, m / z): 182 (M) +. (Reference Example 4) 1- (2,5-dimethyl-imidazo [1,2- α] pyridin-3-yl)-
Reference Example 1 using ethanone 2-amino-6-methylpyridine
The reaction was carried out in the same manner as in (1) to obtain the title compound.

1H-NMR (CDCl3) δ: 7.53 (d, 1H, J = 8.7H
z), 7.40 (t, 1H, J = 8.7Hz), 6.81 (d, 1H, J = 6.9Hz),
2.76 (s, 2H), 2.68 (s, 3H), 2.49 (s, 3H); MS (APCI, m / z): 189 (M + H) +; HPLC (N): Rt = 2.6 min. (Reference Example 5) 2-bromo-1- (2,6-dimethyl-imidazo [1,2-α] pyridine-
Reaction was carried out in the same manner as in Reference Example 1 using 3-yl) -ethanone 2-amino-5-methylpyridine to obtain the title compound.

1H-NMR (CDCl3) δ: 9.57 (s, 1H), 7.58
(d, 1H, J = 9.2Hz), 7.38 (dd, 1H, J = 1.9Hz, 9.2Hz), 4.
37 (s, 2H), 2.85 (s, 3H), 2.42 (s, 3H); MS (APCI, m / z): 267 (M + H) +, 269 (M + H) +; HPLC (N) : Rt = 2.4 min. (Reference Example 6) 2-bromo-1- (2,7-dimethyl-imidazo [1,2-α] pyridine-
The reaction was carried out in the same manner as in Reference Example 1 using 3-yl) -ethanone 2-amino-4-methylpyridine to obtain the title compound.

1H-NMR (CDCl3) δ: 9.58 (d, 1H, J = 7.0H
z), 7.43 (d, 1H, J = 1.6Hz), 6.91 (dd, 1H, J = 1.6Hz,
7.0Hz), 4.35 (s, 2H), 2.84 (s, 3H), 2.48 (s, 3H); MS (APCI, m / z): 267 (M + H) +, 269 (M + H) +; HPLC (N): Rt = 2.3 min. (Reference Example 7) 2-bromo-1- (2,5,7-trimethyl-imidazo [1,2-α] pyridin-3-yl) -ethanone 2-amino- The reaction was carried out in the same manner as in Reference Example 1 using 4,6-dimethylpyridine to obtain the title compound.

1H-NMR (CDCl3) δ: 7.32 (s, 1H), 6.70
(s, 1H), 4.42 (s, 2H), 2.78 (s, 3H), 2.47 (s, 3H),
2.44 (s, 3H); MS (APCI, m / z): 281 (M + H) +, 283 (M + H) +; HPLC (N): Rt = 2.5 min. (Reference Example 8) 2-methyl -Imidazo [1,2-α] pyridine-3-carboxylic acid methoxy-methyl-amide 910 mg (4.46 mmol) of 2-methyl-imidazo [1,2-α] pyridine-3-carboxylic acid ethyl ester in 10 ml of ethanol And 2N-sodium hydroxide 3.34 ml
(6.68 mmol), and the mixture was stirred at room temperature for 1.5 hours and then at 60 ° C. for 2 hours. The reaction solution was concentrated under reduced pressure, 5 ml of a hydrogen chloride-methanol solution was added, and the solvent was concentrated under reduced pressure.
The obtained crystal was used for the next reaction as it was.

1.20 g of the crystals obtained above, 602 mg (4.46 mmol) of 1-hydroxybenzotriazole, 1.86 ml (13.4 mmol) of triethylamine and N, O-dimethylhydroxylamine hydrochloride 65
2 mg (6.69 mmol) was dissolved in 15 ml of N, N-dimethylformamide and cooled with ice. 1.28 g of 1-ethyl-3- (dimethylaminopropyl) carbodiimide hydrochloride
(6.68 mmol), and the mixture was stirred for 15 hours while the temperature was naturally raised to room temperature in an ice bath. Ethyl acetate was added to the reaction solution, and the mixture was washed with a saturated aqueous solution of sodium hydrogen carbonate and saturated saline. After the organic layer was dried over anhydrous sodium sulfate, the solvent was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate) to give the title compound 65
4 mg (67%) were obtained.

1H-NMR (CDCl3) δ: 8.60 (d, 1H, J = 6.8H
z), 8.02 (brs, 1H), 7.57 (d, 1H, J = 8.9Hz), 7.28 (t,
1H, J = 8.4Hz), 6.87 (t, 1H, J = 8.4Hz), 3.58 (s, 3
H), 3.41 (s, 3H), 2.56 (s, 3H); MS (APCI, m / z): 220 (M + H) +; HPLC (N): Rt = 3.1 min. (Reference Example 9) 2 -Bromo-1- (2-methyl-imidazo [1,2-α] pyridin-3-yl) -propan-1-one (1) 1- (2-Methyl-imidazo [1,2-α] pyridine- 3-yl)
-Propan-1-one 312 mg (1.42 mmol) of 2-methyl-imidazo [1,2-α] pyridine-3-carboxylic acid methoxy-methyl-amide was dissolved in 5 ml of anhydrous tetrahydrofuran under a nitrogen stream and cooled with ice. did. Ethyl magnesium bromide (2.84 ml, 2.84 mmol, 1.0 M solution in tetrahydrofuran) was added dropwise over 5 minutes, and the mixture was stirred at the same temperature for 2 hours. Saturated ammonium chloride was added dropwise, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over anhydrous sodium sulfate,
The solvent was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate) to give 1- (2-methyl-imidazo [1,2-α] pyridin-3-yl) -propane-1-
220 mg (82%) of on were obtained.

1H-NMR (CDCl3) δ: 9.89 (d, 1H, J = 7.0H
z), 7.64 (d, 1H, J = 8.9Hz), 7.44 (dt, 1H, J = 1.1Hz,
7.0Hz), 7.01 (t, 1H, J = 6.8Hz), 2.94 (q, 2H, J = 7.3H
z), 2.81 (s, 3H), 1.29 (t, 3H, J = 7.3 Hz); MS (EI, m / z): 188 (M) +. (2) 1- (2- Reference Example 1 using methyl-imidazo [1,2-α] pyridin-3-yl) -propan-1-one
The reaction was carried out in the same manner as in (2) to obtain 2-bromo-1- (2-methyl-imidazo [1,2-α] pyridin-3-yl) -propan-1-one.

1H-NMR (CDCl3) δ: 9.78 (d, 1H, J = 6.8H
z), 7.68 (d, 1H, J = 9.2Hz), 7.52 (t, 1H, J = 7.8Hz),
7.08 (t, 1H, J = 6.8Hz), 5.17 (q, 1H, J = 6.8Hz), 2.91
(s, 3H), 1.95 (d, 3H, J = 6.8 Hz); MS (EI, m / z): 266 (M) +, 268 (M) +. (Reference Example 10) 2-bromo-1- Reference Example 1 using (6-bromo-2-methyl-imidazo [1,2-α] pyridin-3-yl) -ethanone 2-amino-5-bromo-pyridine
The reaction was carried out in the same manner as in to give the title compound.

1H-NMR (CDCl3) δ: 9.90 (s, 1H), 7.61-
7.51 (m, 2H), 4.34 (s, 2H), 2.84 (s, 3H); MS (APCI, m / z): 333 (M + H) +, 335 (M + H) +; HPLC (N) : Rt = 2.1 min. (Reference Example 11) 2-bromo-1- (2-methyl-6-trifluoromethyl-imidazo)
[1,2-α] pyridin-3-yl) -ethanone Using 2-amino-5-trifluoromethyl-pyridine, the reaction was carried out in the same manner as in Reference Example 1 to obtain the title compound.

1H-NMR (CDCl3) δ: 9.84 (s, 1H), 7.58
(d, 1H, J = 9.2Hz), 7.43 (d, 1H, J = 8.6Hz), 2.90 (s,
2H), 2.63 (s, 3H); MS (APCI, m / z): 321 (M + H) +, 323 (M + H) +; HPLC (N): Rt = 2.0 min. (Reference Example 12) Reference Example 1 using 2-bromo-1- (6-chloro-2-methyl-imidazo [1,2-α] pyridin-3-yl) -ethanone 2-amino-5-chloro-pyridine
The reaction was carried out in the same manner as in to give the title compound.

1H-NMR (CDCl3) δ: 9.82 (s, 1H), 7.62
(d, 1H, J = 9.2Hz), 7.49 (d, 1H, J = 9.2Hz), 4.36 (s,
2H), 2.86 (s, 3H); MS (APCI, m / z): 287 (M + H) +, 289 (M + H) +; HPLC (N): Rt = 2.0 min. (Reference Example 13) 2-Bromo-1- (2-methyl-imidazo [1,2-α] pyridin-3-yl) -2-phenyl-ethanone Using benzylmagnesium bromide, the reaction was carried out in the same manner as in Reference Example 9 to give the notation. The compound was obtained.

1H-NMR (CDCl3) δ: 9.81 (d, 1H, J = 6.8H
z), 7.75-7.61 (m, 3H), 7.53 (t, 1H, J = 7.8Hz), 7.43-
7.27 (m, 3H) 7.08 (t, 1H, J = 7.0Hz), 6.29 (s, 1H),
2.92 (s, 3H); MS (APCI, m / z): 329 (M + H) +, 331 (M + H) +; HPLC (N): Rt = 2.5 min. (Reference Example 14) 2-bromo -1- (2-Methyl-imidazo [1,2-α] pyridin-3-yl) -pentan-1-one The reaction was carried out in the same manner as in Reference Example 9 using butylmagnesium bromide to obtain the title compound. Was.

1H-NMR (CDCl3) δ: 9.79 (d, 1H, J = 7.0H
z), 7.69 (d, 1H, J = 8.9Hz), 7.53 (t, 1H, J = 7.6Hz),
7.09 (t, 1H, J = 7.3Hz), 5.04 (t, 1H, J = 7.0Hz), 2.90
(s, 3H), 2.28-2.14 (m, 2H), 1.52-1.43 (m, 2H), 1.00
(t, 3H, J = 7.0Hz); MS (EI, m / z): 294 (M) +, 296 (M) +. (Reference Example 15) 2-bromo-3-methyl-1- (2- Methyl-imidazo [1,2-α] pyridin-3-yl) -butan-1-one The reaction was carried out in the same manner as in Reference Example 9 using isobutylmagnesium bromide to obtain the title compound.

1H-NMR (CDCl3) δ: 9.79 (dt, 1H, J = 0.8
Hz, 7.3Hz), 7.68 (dt, 1H, J = 0.8Hz, 8.6Hz), 7.53 (d
t, 1H, J = 0.8Hz, 7.0Hz), 7.08 (dt, 1H, J = 1.3Hz, 7.0
Hz), 4.80 (d, 1H, J = 8.9Hz), 2.88 (s, 3H), 2.61-2.50
(m, 1H), 1.25 (d, 3H, J = 6.5Hz), 1.04 (d, 3H, J = 6.
MS (EI, m / z): 294 (M) +, 296 (M) +. (Reference Example 16) 2-bromo-1- (2-methyl-imidazo [1,2-α] isoquinoline-
The reaction was performed in the same manner as in Reference Example 1 using 3-yl) -ethanone isoquinolin-3-ylamine to obtain the title compound.

1H-NMR (CDCl3) δ: 10.77 (brs, 1H), 8.
14 (brs, 1H), 7.98-7.88 (m, 2H), 7.58-7.48 (m, 2H),
4.44 (s, 2H), 2.98 (s, 3H); MS (APCI, m / z): 303 (M + H) +, 305 (M + H) +; HPLC (N): Rt = 2.6 min. Reference Example 17) A reaction was performed in the same manner as in Reference Example 1 using 2-bromo-1- (2-methyl-imidazo [1,2-α] quinolin-3-yl) -ethanone isoquinolin-1-ylamine, The title compound was obtained.

1H-NMR (CDCl3) δ: 9.40 (d, 1H, J = 7.6H
z), 8.73-8.70 (m, 1H), 7.83-7.79 (m, 1H), 7.74-7.68
(m, 2H), 7.32-7.25 (m, 1H), 4.41 (s, 2H), 2.98 (s,
3H); MS (APCI, m / z): 303 (M + H) +, 305 (M + H) +; HPLC (N): Rt = 2.9 min. (Reference Example 18) 2-bromo-1- ( Reference Example 1 using 2-methyl-6-phenyl-imidazo [1,2-α] pyridin-3-yl) -ethanone 5-phenyl-pyridin-2-ylamine
The reaction was carried out in the same manner as in to give the title compound.

1H-NMR (CDCl3) δ: 10.00 (s, 1H), 7.82
-7.23 (m, 2H), 7.65-7.62 (m, 2H), 7.52-7.40 (m, 3
H), 4.41 (s, 2H), 2.90 (s, 3H); MS (APCI, m / z): 329 (M + H) +, 331 (M + H) +; HPLC (N): Rt = 2.3 min. (Reference Example 19) 2-trifluoromethyl-imidazo [1,2-α] pyridine-3-carboxylic acid methoxy-methyl-amide 2-trifluoromethyl-imidazo [1,2-α] pyridine-3- The reaction was carried out in the same manner as in Reference Example 8 using carboxylic acid ethyl ester to obtain the title compound.

1H-NMR (CDCl3) δ: 8.37 (d, 1H, J = 7.0H
z), 7.75 (d, 1H, J = 9.2Hz), 7.42 (t, 1H, J = 7.8Hz),
7.02 (t, 1H, J = 7.0Hz), 3.52 (s, 3H), 3.46 (s, 3H); MS (APCI, m / z): 274 (M + H) +; HPLC (N): Rt = 3.3 min. (Reference Example 20) 2-bromo-1- (2-trifluoromethyl-imidazo [1,2-α]
(Pyridin-3-yl) -ethanone Using the compound obtained in Reference Example 19 and methylmagnesium bromide, the reaction was carried out in the same manner as in Reference Example 9 to obtain the title compound.

1H-NMR (CDCl3) δ: 9,70 (d, 1H, J = 6.8H
z), 7.90 (d, 1H, J = 8.9Hz), 7.67 (dt, 1H, J = 0.8Hz,
8.1Hz), 7.28 (dt, 1H, J = 0.8Hz, 7.0Hz), 4.65 (s, 2
H); MS (APCI, m / z): 307 (M + H) +, 309 (M + H) + b; HPLC (N): Rt = 2.1 min. (Reference Example 21) 2-bromo-1- (2-phenyl-imidazo [1,2-α] pyridine-3-
Yl) -ethanone Using 1- (2-phenyl-imidazo [1,2-α] pyridin-3-yl) -ethanone, the reaction was carried out in the same manner as in Reference Example 1 (2).
The title compound was obtained.

1H-NMR (CDCl3) δ: 9.75 (d, 1H, J = 7.0H
z), 7.79 (d, 1H, J = 8.9Hz), 7.66-7.52 (m, 6H), 7.17
(dt, 1H, J = 1.1Hz, 7.0Hz), 4.00 (s, 2H); MS (APCI, m / z): 315 (M + H) +, 317 (M + H) +; HPLC (N) : Rt = 2.5 min. (Reference Example 22) Reference Example using 1- (8-amino-2-methyl-imidazo [1,2-α] pyridin-3-yl) -ethanone 2,3-diaminopyridine The reaction was carried out in the same manner as in 1 (1) to obtain the title compound.

1H-NMR (CDCl3) δ: 9.15 (dd, 1H, J = 1.1
Hz, 7.0Hz), 6.82 (t, 1H, J = 7.3Hz), 6.63 (dd, 1H, J
= 1.1Hz, 7.6Hz), 4.50 (brs, 2H), 2.77 (s, 3H), 2.60
(s, 3H); MS (APCI, m / z): 190 (M + H) +; HPLC (N): Rt = 3.0 min. (Reference Example 23) N- (3-acetyl-2-methyl-imidazo) [1,2-α] pyridine-8-
Yl) -2,2,2-trifluoro-acetamide 133 mg of the compound 1- (8-amino-2-methyl-imidazo [1,2-α] pyridin-3-yl) -ethanone obtained in Reference Example 22
(0.703 mmol) was dissolved in 1 ml of pyridine and 2 ml of dichloromethane and cooled with ice. Trifluoroacetic anhydride 19
9 μl (1.41 mmol) was added, and the mixture was stirred for 15 hours while being naturally warmed to room temperature in an ice bath. Ethyl acetate was added to the reaction solution, and the mixture was washed with a saturated aqueous solution of sodium hydrogen carbonate and saturated saline. After the organic layer was dried over anhydrous sodium sulfate, the solvent was concentrated under reduced pressure, and the obtained crystals were finely pulverized and washed with hexane-ethyl ether to obtain 166 mg (83%) of the title compound.

1H-NMR (CDCl3) δ: 9.47 (dd, 1H, J = 1.1
Hz, 7.0Hz), 8.36 (dd, 1H, J = 1.1Hz, 7.8Hz), 7.04
(t, 1H, J = 7.6Hz), 2.80 (s, 3H), 2.64 (s, 3H); MS (APCI, m / z): 286 (M + H) +; HPLC (N): Rt = 2.1 min. (Reference Example 24) 1- (8-amino-7-bromo-2-methyl-imidazo [1,2-α] pyridin-3-yl) -2-bromo-ethanone Compound obtained in Reference Example 23 Reference Example 1 (2)
The reaction was carried out in the same manner as in to give the title compound.

1H-NMR (CDCl3) δ: 9.04 (d, 1H, J = 7.3H
z), 7.11 (d, 1H, J = 7.3Hz), 4.97 (brs, 1H), 4.39 (s,
2H), 2.88 (s, 3H); MS (APCI, m / z): 346 (M + H) +, 348 (M + H) +; HPLC (N): Rt = 2.6 min. (Reference Example 25) 2-bromo-1-imidazo [1,2-α] pyridin-3-yl-ethanone Using imidazo [1,2-α] pyridin-3-yl-ethanone,
The reaction was carried out in the same manner as in Reference Example 1 (2) to obtain the title compound.

1H-NMR (CDCl3) δ: 9.61 (dd, 1H, J = 1.1
Hz, 7.0Hz), 8.46 (s, 1H), 7.81 (d, 1H, J = 8.1Hz),
7.58 (t, 1H, J = 7.0Hz), 7.17 (t, 1H, J = 7.0Hz), 4.38
(s, 1H), 4.39 (s, 2H), 2.88 (s, 3H); MS (APCI, m / z): 239 (M + H) +, 241 (M + H) +; HPLC (N): Rt = 2.8 min. (Reference Example 26) 1- (3-Methyl-imidazo [1,2-α] pyridin-3-yl) -ethanone 2-aminopyridine and 4-bromo-pentane-2,3-dione The reaction was carried out in the same manner as in Reference Example 1 (1) to obtain the title compound.

1H-NMR (CDCl3) δ: 7.92 (d, 1H, J = 6.8H
z), 7.65 (d, 1H, J = 9.5Hz), 7.23 (dd, 1H, J = 1.1Hz,
8.9Hz), 6.91 (t, 1H, J = 6.8Hz), 2.80 (s, 3H), 2.74
(s, 3H); MS (APCI, m / z): 175 (M + H) +; HPLC (N): Rt = 2.7 min. (Reference Example 27) 2-bromo-1- (3-methyl-imidazo [1,2-α] pyridin-2-yl) -ethanone Using the compound of Reference Example 26, a reaction was carried out in the same manner as in Reference Example 1 (2) to obtain the title compound.

1H-NMR (CDCl3) δ: 7.93 (d, 1H, J = 7.0H
z), 7.64 (d, 1H, J = 9.5Hz), 7.31-7.25 (m, 1H), 6.93
(t, 1H, J = 6.8Hz), 4.81 (s, 2H), 2.82 (s, 3H); MS (APCI, m / z): 253 (M + H) +, 255 (M + H) +; HPLC (N): Rt = 3.0 min. (Reference Example 28) 1- (8-benzyloxy-2-methyl-imidazo [1,2-α] pyridin-3-yl) -2-bromo-ethanone Under a nitrogen stream 1- (8-benzyloxy-2-methyl-imidazo [1,
2-α] pyridin-3-yl) -2-ethanone 500 mg (1.78)
Mmol) in 15 ml of anhydrous tetrahydrofuran,
Cooled to -78 ° C. 5.34 ml (5.34 mmol, 1.0 M tetrahydrofuran solution) of lithium bis (trimethylsilyl) amide was added dropwise over 3 minutes, and the mixture was added at -78 ° C for 1 minute.
Stirred for hours. Trimethylsilyl chloride 0.903
ml (7.12 mmol) was added and stirred for 30 minutes. Saturated ammonium chloride was added dropwise, and the temperature was raised to room temperature. The reaction solution was extracted with ethyl acetate, the organic layer was washed with saturated saline, dried over anhydrous sodium sulfate, and the solvent was concentrated under reduced pressure.

The obtained residue was dissolved in 15 ml of anhydrous tetrahydrofuran under a stream of nitrogen and cooled with ice. 380 mg (2.14 mmol) of N-bromosuccinimide was added, and the mixture was stirred for 13 hours while being naturally warmed to room temperature in an ice bath. Ethyl acetate was added to the reaction solution, and the mixture was washed with a saturated aqueous solution of sodium hydrogen carbonate and saturated saline. After the organic layer was dried over anhydrous sodium sulfate, the solvent was concentrated under reduced pressure, and the obtained residue was subjected to silica gel column chromatography (hexane / hexane).
The residue was purified by ethyl acetate = 1: 1) to give 343 mg of the title compound.
(54%).

1H-NMR (CDCl3) δ: 9.30 (dd, 1H, J = 1.1
Hz, 6.8Hz), 7.47 (d, 2H, J = 6.5Hz), 7.41-7.29 (m, 3
H), 6.91-6.80 (m, 2H), 5.38 (s, 2H), 4.38 (s, 2H),
2.89 (s, 3H); MS (APCI, m / z): 359 (M + H) +, 361 (M + H) +; HPLC (N): Rt = 3.2 min. (Reference Example 29) 1- ( 8-hydroxy-2-methyl-imidazo [1,2-α] pyridine-
3-yl) -2-ethanone 2.29 g (8.17 mmol) of 1- (8-benzyloxy-2-methyl-imidazo [1,2-α] pyridin-3-yl) -2-ethanone in 20 ml of methanol , Palladium-carbon (10%, 300 mg) was added, and the mixture was stirred under hydrogen pressure (1 atm) for 2 hours. The reaction solution was filtered through celite, the mother liquor was concentrated under reduced pressure, and the obtained crystals were finely pulverized and washed with hexane-ethyl acetate to obtain 1.19 g (77%) of the title compound.

1H-NMR (DMSO-d6) δ: 9.15 (d, 1H, J = 6.
8Hz), 6.98 (t, 1H, J = 7.0Hz), 6.84 (d, 1H, J = 7.8H
z), 2.72 (s, 2H), 4.38 (s, 3H), 2.57 (s, 3H); MS (APCI, m / z): 191 (M + H) +; HPLC (N): Rt = 3.1 min Reference Example 30 1- (8-Methoxy-2-methyl-imidazo [1,2-α] pyridine-3-
Il) -2-Ethanone 200 mg (1.05 mmol) of the compound obtained in Reference Example 29 was dissolved in 8 ml of methanol, and about 3 ml of (trimethylsilyl) diazomethane (10% hexane solution) was added at room temperature, followed by stirring for 1 hour. The reaction solution was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (ethyl acetate) to obtain 72 mg (34%) of the title compound.

1H-NMR (CDCl3) δ: 9.32 (d, 1H, J = 7.8H
z), 6.91 (t, 1H, J = 6.8Hz), 6.77 (d, 1H, J = 7.6Hz),
4.04 (s, 3H), 2.86 (s, 3H), 2.62 (s, 3H); MS (APCI, m / z): 205 (M + H) +; HPLC (N): Rt = 2.8 min. Example 31) 2-bromo-1- (8-methoxy-2-methyl-imidazo [1,2-α] pyridin-3-yl) -2-ethanone Reference example using the compound obtained in Reference example 30 The reaction was carried out in the same manner as in Example 28 to obtain the title compound.

1H-NMR (CDCl3) δ: 9.31 (dd, 1H, J = 1.1
Hz, 7.0Hz), 6.98 (t, 1H, J = 7.0Hz), 6.84 (dd, 1H, J
= 0.8Hz, 7.6Hz), 4.38 (s, 2H), 4.05 (s, 3H), 2.88
(s, 3H); MS (EI, m / z): 282 (M) +, 284 (M) +. (Reference Example 32) 1- [8- (tert-butyl-dimethyl-silanoyl) 2-methyl- Imidazo [1,2-α] pyridin-3-yl) -2-ethanone 509 mg (2.68 mmol) of the compound obtained in Reference Example 29 and 1.12 ml (8.03 mmol) of triethylamine were mixed with N, N-dimethyl. It was dissolved in 5 ml of formamide and cooled with ice. tert-butyl-dimethyl-silyl chloride 808mg
(5.36 mmol) was added, and the mixture was stirred for 5 hours while being naturally warmed to room temperature in an ice bath. Ethyl acetate was added to the reaction solution, and the mixture was washed with a saturated aqueous solution of sodium hydrogen carbonate and a saturated saline solution. After the organic layer was dried over anhydrous sodium sulfate, the solvent was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane / ethyl acetate = 1: 1) to obtain 816 mg (quantitative) of the title compound.

1H-NMR (CDCl3) δ: 9.39 (t, 1H, J = 4.1H
z, 7.0Hz), 6.84 (d, 2H, J = 4.1Hz), 2.79 (s, 3H), 2.
61 (s, 3H), 1.06 (s, 9H), 0.31 (s, 6H); MS (EI, m / z): 305 (M + H) +. (Reference Example 33) 1) 2-Bromo-1 -[8- (tert-butyl-dimethyl-silanoyl) 2-methyl-imidazo [1,2-α] pyridin-3-yl) -2-ethanone 2) 2-bromo-1- [7-bromo-8- (tert-butyl-dimethyl-
(Silanoyl) 2-methyl-imidazo [1,2-α] pyridin-3-yl) -2-ethanone Using the compound obtained in Reference Example 32, the reaction was carried out in the same manner as in Reference Example 28 to obtain the title compound. Was. 1) 1H-NMR (CDCl3) δ: 9.37 (t, 1H, J = 3.8Hz), 6.91
(d, 2H, J = 3.8Hz), 4.37 (s, 2H), 2.85 (s, 3H), 0.9
1 (s, 9H), 0.30 (s, 6H); MS (APCI, m / z) 383 (M + H) +, 385 (M + H) +; HPLC (N): Rt = 1.4 min. 2) 1H-NMR (CDCl3) δ 9.20 (d, 1H, J = 7.6Hz), 7.13
(d, 1H, J = 7.3Hz), 4.34 (s, 2H), 2.85 (s, 3H), 1.10
(s, 9H), 0.39 (s, 6H); MS (APCI, m / z): 461 (M + H) +, 463 (M + H) +; HPLC (N): Rt = 1.6 min. Example 34) 1- (2-methoxymethyl-imidazo [1,2-α] pyridin-3-yl) -2-ethanone 2-methoxy-N-pyridin-2-yl-acetamide 1.27
g (7.64 mmol) was dissolved in 20 ml of ethanol, and 1.74 ml (11.5 mmol) of bromoacetone was added.
The mixture was refluxed for 14 hours. The solvent was concentrated under reduced pressure, ethyl acetate was added, and the mixture was washed with a saturated aqueous solution of sodium hydrogen carbonate and a saturated saline solution. The organic layer was dried over anhydrous sodium sulfate, and the solvent was concentrated under reduced pressure. The obtained crystals were finely pulverized, washed with hexane-ethyl acetate, and 590 mg of the title compound (20 mg).
%).

MS (APCI, m / z): 205 (M + H) +; HPLC (N): Rt = 3.0 min. (Reference Example 35) 2-bromo-1- (2-methoxymethyl-imidazo [1] (2, α) pyridin-3-yl) -2-ethanone The compound of Reference Example 34 was reacted in the same manner as in Reference Example 1 (2) to obtain the title compound.

1H-NMR (CDCl3) δ: 9.70 (dt, 1H, J = 1.1
Hz, 7.0Hz), 7.76 (dt, 1H, J = 1.1Hz, 8.9Hz), 7.56 (d
t, 1H, J = 1.4Hz, 7.0Hz), 7.15 (dt, 1H, J = 1.4Hz, 7.0
Hz), 5.17 (s, 2H), 4.63 (s, 2H), 3.48 (s, 3H); MS (APCI, m / z) 283 (M + H) +, 285 (M + H) +; HPLC ( N): Rt = 2.2 min. (Reference Example 36) Using 1- (2-ethyl-imidazo [1,2-α] pyridin-3-yl) -2-ethanone N-pyridin-2-yl-propionamide Then, the reaction was carried out in the same manner as in Reference Example 34 to obtain the title compound.

1H-NMR (CDCl3) δ: 9.76 (d, 1H, J = 7.0H
z), 7.67 (d, 1H, J = 8.9Hz), 7.46 (dt, 1H, J = 1.4Hz,
7.0Hz), 7.01 (dt, 1H, J = 1.4Hz, 7.0Hz), 3.15 (q, 2
H, J = 7.6Hz), 2.66 (s, 3H), 1.47 (t, 3H, J = 7.6Hz); MS (APCI, m / z): 189 (M + H) +; HPLC (N): Rt = 1.7 min. (Reference Example 37) 2-bromo-1- (2-ethyl-imidazo [1,2-α] pyridin-3-yl) -2-ethanone Using the compound of Reference Example 36, Reference Example 1 The reaction was carried out in the same manner as in (2) to obtain the title compound.

1H-NMR (CDCl3) δ: 9.75 (dt, 1H, J = 1.1
Hz, 7.0Hz), 7.72 (dt, 1H, J = 1.1Hz, 8.9Hz), 7.52 (d
t, 1H, J = 1.4Hz, 7.0Hz), 7.08 (dt, 1H, J = 1.4Hz, 7.0
Hz), 4.40 (s, 2H), 3.15 (q, 2H, J = 7.6Hz), 1.52 (t, 3
H, J = 7.6Hz); MS (APCI, m / z): 267 (M + H) +, 269 (M + H) +; HPLC (N): Rt = 2.1 min. (Reference Example 38) 3- Acetyl-imidazo [1,2-α] pyridine-2-carboxylic acid
Methyl ester The reaction was carried out in the same manner as in Reference Example 34 using N-pyridin-2-yl-oxamic acid methyl ester to obtain the title compound.

1H-NMR (CDCl3) δ: 9.60 (dt, 1H, J = 1.1
Hz, 7.0Hz), 7.79 (dt, 1H, J = 1.1Hz, 8.9Hz), 7.53 (d
t, 1H, J = 1.4Hz, 6.8Hz), 7.12 (dt, 1H, J = 1.4Hz, 6.8
Hz), 4.06 (s, 3H), 2.75 (s, 3H); MS (APCI, m / z): 219 (M + H) +; HPLC (N): Rt = 2.2 min. (Reference Example 39) 3 -(2-bromo-acetyl) -imidazo [1,2-α] pyridine-2-
Carboxylic acid methyl ester Using the compound obtained in Reference Example 38, Reference Example 1 (2)
The reaction was carried out in the same manner as in to give the title compound.

1H-NMR (CDCl3) δ: 9.56 (dt, 1H, J = 1.1
Hz, 7.0Hz), 7.85 (dt, 1H, J = 1.1Hz, 8.9Hz), 7.59 (d
t, 1H, J = 1.4Hz, 6.8Hz), 7.19 (dt, 1H, J = 1.4Hz, 7.0
Hz), 4.82 (s, 2H), 4.09 (s, 3H); MS (EI, m / z): 296 (M) +, 298 (M) +. (Reference Example 40) N, N-dimethyl-4 -Thioureido-benzamide 80 mg (0.408 mmol) of 4-thioureido-benzoic acid are dissolved in 1.5 ml of anhydrous tetrahydrofuran, and N, N-carbonyldiimidazo [1,2-α] 0.612 is added at room temperature.
Mmol) and stirred for 30 minutes. Dimethylamine
0.5 mg of water of 100 mg (0.612 mmol) of hydrochloride
1 solution was added and stirred for 14 hours. Ethyl acetate was added to the reaction solution, and the mixture was washed with a saturated aqueous solution of sodium hydrogen carbonate and saturated saline. The organic layer was dried over anhydrous sodium sulfate, and the solvent was concentrated under reduced pressure. The obtained crystals were finely pulverized, washed with hexane-ethyl acetate, and washed with 20 mg of the title compound (22 mg).
%).

1H-NMR (DMSO-d6) δ: 9.84 (s, 1H), 7.5
6-7.48 (m, 3H), 7.44-7.32 (m, 4H), 2.95 (s, 6H); MS (APCI, m / z): 224 (M + H) +; HPLC (N): Rt = 4.6 (Reference Example 41) A reaction was carried out in the same manner as in Reference Example 40 using an aqueous solution of N-ethyl-4-thioureido-benzamide 33% -ethylamine to obtain the title compound.

1H-NMR (DMSO-d6): δ 9.88 (s, 1H), 8.3
8 (t, 3H, J = 4.9Hz), 7.90-7.40 (m, 2H), 7.79 (d, 2
H, J = 8.4Hz), 7.53 (d, 2H, J = 8.4Hz), 3.30-3.22 (m,
2H), 1.11 (t, 3H, J = 7.3 Hz); MS (APCI, m / z): 224 (M + H) +; HPLC (N): Rt = 5.0 min. (Reference Example 42) N-methoxy Using -N-methyl-4-thioureido-benzamide N, O-dimethylhydroxylamine hydrochloride, the reaction was carried out in the same manner as in Reference Example 40 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 9.91 (s, 1H), 7.9
0-7.30 (m, 2H), 7.60-7.53 (m, 4H), 3.56 (s, 3H), 3.
34 (s, 3H); MS (APCI, m / z): 240 (M + H) +; HPLC (N): Rt = 4.8 min. (Reference Example 43) (6-methoxy-pyridin-3-yl) The reaction was carried out in the same manner as in Reference Example 2 using -thiourea 6-methoxy-pyridin-3-ylamine to obtain the title compound.

1H-NMR (DMSO-d6) δ: 9.52 (s, 1H), 8.0
4 (d, 1H, J = 2.7Hz), 7.69 (dd, 1H, J = 2.7Hz, 8.9Hz),
7.67-7.40 (m, 2H), 6.79 (d, 1H, J = 8.9Hz), 3.83
(s, 3H); MS (APCI, m / z): 184 (M + H) +; HPLC (N): Rt = 3.7 min. (Reference Example 44) (3-Fluoro-4-methyl-phenyl)- Using thiourea 3-fluoro-4-methyl-phenylamine,
The reaction was carried out in the same manner as in Reference Example 2 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 9.76 (s, 1H), 7.7
0-7.30 (m, 2H), 7.40 (d, 1H, J = 12.1Hz), 7.20 (t, 1
H, J = 8.4Hz), 7.03 (dd, 1H, J = 1.9Hz, 8.1Hz), 2.18
(s, 3H); MS (APCI, m / z): 185 (M + H) +; HPLC (N): Rt = 3.6 min. (Reference Example 45) (6-Chloro-pyridin-3-yl)- The reaction was carried out in the same manner as in Reference Example 2 using thiourea 6-chloro-pyridin-3-ylamine to obtain the title compound.

1H-NMR (DMSO-d6) δ: 9.87 (s, 1H), 8.4
0 (d, 1H, J = 2.7Hz), 8.03 (dd, 1H, J = 1.1Hz, 8.4Hz),
7.46 (d, 1H, J = 8.6Hz); MS (APCI, m / z): 188 (M + H) +, 189 (M + H) +; HPLC (N): Rt = 4.0 min. (Reference example) 46) (3,5-Dimethoxy-phenyl) -thiourea The reaction was carried out in the same manner as in Reference Example 3 using 3,5-dimethoxy-phenylamine to obtain the title compound.

1H-NMR (CDCl3) δ: 7.74 (s, 1H), 6.40-
6.35 (m, 3H), 6.15 (brs, 2H), 3.76 (s, 6H); MS (APCI, m / z): 213 (M + H) +; HPLC (N): Rt = 4.1 min. Example 47) (4-Acetyl-phenyl) -thiourea Using 4-acetyl-phenylamine, a reaction was carried out in the same manner as in Reference Example 2 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.02 (s, 1H), 7.
90 (d, 2H, J = 8.6Hz), 7.66 (d, 2H, J = 8.6Hz), 2.55
(s, 3H); MS (APCI, m / z): 195 (M + H) +; HPLC (N): Rt = 4.8 min. (Reference Example 48) (4-cyano-phenyl) -thiourea 4-cyano The reaction was carried out in the same manner as in Reference Example 2 using -phenylamine to obtain the title compound.

1H-NMR (CDCl3) δ: 9.31 (s, 1H), 7.19
(d, 2H, J = 8.4Hz), 6.95 (d, 2H, J = 8.4Hz), 6.56 (s,
2H); MS (FAB, m / z): 178 (M + H) +. (Reference Example 49) The reaction was carried out in the same manner as in Reference Example 2 using ethyl 4-thioureido-ethyl benzoate. This gave the title compound.

1H-NMR (DMSO-d6) δ: 10.02 (s, 1H), 7.
89 (d, 2H, J = 8.6Hz), 7.66 (d, 2H, J = 8.6Hz), 4.29
(q, 2H, 6.8Hz), 3.38 (s, 2H), 1.31 (t, 3H, J = 6.8H
z); MS (APCI, m / z): 225 (M + H) +. HPLC (N): Rt = 4.2 min. (Reference Example 50) 1- [2- (1-methyl-cyclopropyl) -imidazo [1,2-α] pyridin-3-yl] -ethanone (1) 1-methyl-cyclopropanecarboxylic acid pyridine-
3.19 g of 2-ylamide 1-methyl-cyclopropanecarboxylic acid, 1-
2.15 g (15.9 mmol) of hydroxybenzotriazole and 1.50 g (1
5.9 mmol) was dissolved in 30 ml of tetrahydrofuran and cooled with ice. 6.11 g (31.9 mmol) of 1-ethyl-3- (dimethylaminopropyl) carbodiimide hydrochloride was added, and the mixture was stirred for 15 hours while naturally warming to room temperature in an ice bath. Ethyl acetate was added to the reaction solution, and the mixture was washed with a saturated aqueous solution of sodium hydrogen carbonate and a saturated saline solution. After the organic layer was dried over anhydrous sodium sulfate, the solvent was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane / ethyl acetate = 1: 1) to obtain 1.75 g (63%) of the title compound.

1H-NMR (CDCl3) δ: 8.27-8.19 (m, 3H),
7.72-7.67 (m, 1H), 7.05-7.00 (m, 1H), 1.49 (s, 3H),
1.35-1.29 (m, 2H), 0.74-0.70 (m, 2H); MS (APCI, m / z): 177 (M + H) +; HPLC (N): Rt = 1.5 min. (2) 1- [2- (1-methyl-cyclopropyl) -imidazo [1,2-
α] pyridin-3-yl] -ethanone 1-methyl-cyclopropanecarboxylic acid The reaction was carried out in the same manner as in Reference Example 34 using pyridine-2-ylamide to obtain the title compound.

1H-NMR (CDCl3) δ: 9.75 (d, 1H, J = 6.8H
z), 7.67 (d, 1H, J = 8.9Hz), 7.45 (t, 1H, J = 8.1Hz),
7.02 (t, 1H, J = 6.8Hz), 2.83 (s, 3H), 1.25-1.21 (m,
2H), 1.00-0.97 (m, 2H); MS (APCI, m / z): 215 (M + H) +. HPLC (N): Rt = 1.7 min. (Reference Example 51) 2-bromo-1- [2- (1-methyl-cyclopropyl) -imidazo
[1,2-α] pyridin-3-yl] -ethanone Using the compound obtained in Reference Example 50, a reaction was carried out in the same manner as in Reference Example 28 to obtain the title compound.

1H-NMR (CDCl3) δ: 9.72 (d, 1H, J = 7.0H
z), 7.71 (d, 1H, J = 6.5Hz), 7.53 (t, 1H, J = 8.9Hz),
7.09 (t, 1H, J = 7.0Hz), 4.83 (s, 2H), 1.59 (s, 3H),
1.29-1.27 (m, 2H), 1.03-0.99 (m, 2H); MS (APCI, m / z): 293 (M + H) +, 295 (M + H) +; HPLC (N): Rt = 2.1 min. (Reference Example 52) 1- (2-isopropyl-imidazo [1,2-α] pyridin-3-yl)
Using 2--2-ethanone N-pyridin-2-yl-isobutylamide, the reaction was carried out in the same manner as in Reference Example 34 to obtain the title compound.

1H-NMR (CDCl3) δ: 9.76 (d, 1H, J = 7.3H
z), 7.70 (d, 1H, J = 8.6Hz), 7.45 (t, 1H, J = 8.4Hz),
7.00 (t, 1H, J = 7.0Hz), 3.70-3.65 (m, 1H), 1.48 (s,
3H), 1.40 (s, 3H); MS (APCI, m / z): 203 (M + H) +; HPLC (N): Rt = 1.7 min. (Reference Example 53) 2-bromo-1- (2 -Isopropyl-imidazo [1,2-α] pyridin-3-yl) -2-ethanone The compound obtained in Reference Example 52 was reacted in the same manner as in Reference Example 28 to obtain the title compound.

1H-NMR (CDCl3) δ: 9.74 (d, 1H, J = 6.8H
z), 7.73 (d, 1H, J = 9.2Hz), 7.51 (t, 1H, J = 6.8Hz),
7.07 (t, 1H, J = 7.8Hz), 4.44 (s, 2H), 3.63-3.53 (m,
1H), 1.48 (s, 3H), 1.47 (s, 3H). (Reference Example 54) 1- (2-propyl-imidazo [1,2-α] pyridin-3-yl) -2-
Reference Example 34 using ethanone N-pyridin-2-yl-butylamide
The reaction was carried out in the same manner as in to give the title compound.

1H-NMR (CDCl3) δ: 9.75 (d, 1H, J = 7.0H
z), 7.66 (d, 1H, J = 8.9Hz), 7.45 (dt, 1H, J = 0.8Hz,
6.8Hz), 7.01 (t, 1H, J = 7.0Hz), 3.12-3.07 (m, 2H),
2.66 (s, 3H), 1.98-1.84 (m, 2H), 1.10 (t, 3H, J = 7.3
Hz); MS (APCI, m / z) 203 (M + H) +; HPLC (N): Rt = 1.9 min. (Reference Example 55) 2-bromo-1- (2-propyl-imidazo [1,2 -α] pyridine-3-
Il) -2-Ethanone Using the compound obtained in Reference Example 54, a reaction was carried out in the same manner as in Reference Example 28 to obtain the title compound.

1H-NMR (CDCl3) δ: 9.75 (d, 1H, J = 7.0H
z), 7.70 (d, 1H, J = 8.9Hz), 7.53 (t, 1H, J = 7.8Hz),
7.09 (t, 1H, J = 6.8Hz), 4.41 (s, 2H), 3.11 (t, 2H, J
= 8.1Hz), 2.05-1.95 (m, 2H), 1.19 (t, 3H, J = 7.3Hz). (Reference Example 56) 2-bromo-1- (2-methyl-imidazo [1,2-α] Pyridin-3-yl) -2-ethanone Using 1- (2-methyl-imidazo [1,2-α] pyridin-3-yl) -2-ethanone, the reaction was carried out in the same manner as in Reference Example 1 (2). Do,
The title compound was obtained.

1H-NMR (CDCl3) δ: 9.73 (d, 1H, J = 6.8H
z), 7.69 (d, 1H, J = 8.9Hz), 7.54 (t, 1H, J = 7.9Hz),
7.10 (t, 1H, J = 6.7Hz), 4.38 (s, 2H), 2.87 (s, 3H); MS (EI, m / z): 252 (M) +, 254 (M) +. 57) Using 2-bromo-1- (2-methyl-imidazo [1,2-α] quinolin-1-yl) -ethanone quinolin-1-ylamine, the reaction was carried out in the same manner as in Reference Example 1 to give the title compound I got

1H-NMR (CDCl3) δ: 7.87-7.70 (m, 3H),
7.67 (t, 1H, J = 7.3Hz), 7.57-7.50 (m, 2H), 4.45 (s,
(2H), 2.87 (s, 3H). (Reference Example 58) A reaction was carried out in the same manner as in Reference Example 40 using an aqueous solution of N-methyl-4-thioureido-benzamide 40% -N-methylamine to obtain the title compound. Was.

1H-NMR (DMSO-d6) δ: 9.88 (s, 1H), 8.3
6-8.34 (m, 2H), 7.85-7.76 (m, 3H), 7.54 (d, 2H, J =
(8.4 Hz), 2.78 (s, 3H). (Reference Example 59) The reaction was carried out in the same manner as in Reference Example 40 using 4-thioureido-benzamide 28% aqueous ammonia solution to obtain the title compound.

1H-NMR (DMSO-d6) δ: 9.90 (s, 1H), 7.8
9-7.74 (m, 4H), 7.53 (d, 2H, J = 8.4Hz), 7.00-6.98
(m, 2H). (Reference Example 60) 1- (2-Methyl-imidazo [1,2-α] pyrimidin-3-yl) -ethanone pentane-2,4-dione 1.02 ml (9.99 mmol) To a mixed solvent of carbon tetrachloride and water (v / v = 1 / 1,80m
1) and cooled to 0 ° C. 0.52 ml of bromine
(9.99 mmol) was added dropwise over 5 minutes, and the mixture was stirred at room temperature for 1 hour. After separating the reaction solution into a carbon tetrachloride layer and an aqueous layer, the carbon tetrachloride layer was concentrated under reduced pressure (25 ° C, 16 mmH
g), residue (3-bromo-pentane-2,4-dione) 1.0
2 g were obtained. The residue was used for the next reaction without purification.

0.40 g (4.21 g) of 2-aminopyrimidine
0.36 g (4.25 mmol) of sodium hydrogencarbonate was added to 30 ml of a dimethoxyethane solution of the above-mentioned residue (3-bromo-pentane).
-2,4-dione) was added dropwise, and the mixture was stirred at 70 ° C for 3 hours. The reaction solution was concentrated under reduced pressure and dissolved in dichloromethane. The organic layer was washed with saturated saline, dried over anhydrous sodium sulfate, and the solvent was concentrated under reduced pressure. The obtained crystals were finely pulverized and washed with chloroform-hexane to obtain 0.59 g (80%) of the title compound.

1H-NMR (CDCl3) δ: 9.98 (dd, 1H, J = 2.2
Hz, 7.0Hz), 8.72 (dd, 1H, J = 2.2Hz, 4.3Hz), 7.08 (d
d, 1H, J = 4.1Hz, 6.8Hz), 2.86 (s, 3H), 2.65 (s, 3
H). (Reference Example 61) 2-bromo-1- (2-methyl-7-trimethylsilanyl-imidazo)
[1,2-α] pyrimidin-3-yl) -ethanone 1- (2-methyl-imidazo [1,2-α] pyrimidine under nitrogen stream
3-yl) -ethanone (Reference Example 60) 100 mg (0.57)
Mmol) in 3 ml of anhydrous tetrahydrofuran.
Cooled to 78 ° C. Lithium bis (trimethylsilyl)
2.28 ml (2.28 mmol, 1.0 M solution in tetrahydrofuran) of the amide were added dropwise over 3 minutes, and the mixture was stirred at -78 ° C for 1 hour. 0.36 ml of trimethylsilyl chloride
(2.85 mmol) was added and stirred for 30 minutes. Saturated ammonium chloride was added dropwise, and the temperature was raised to room temperature.
The reaction solution was extracted with ethyl acetate, the organic layer was washed with saturated saline, dried over anhydrous sodium sulfate, and the solvent was concentrated under reduced pressure.

The obtained residue was dissolved in anhydrous tetrahydrofuran (3 ml) under a nitrogen stream and cooled with ice. 122 mg (1.14 mmol) of N-bromosuccinimide was added and the mixture was stirred for 30 minutes. Then, it heated up to room temperature and stirred for 3 hours.
Ethyl acetate was added to the reaction solution, and the mixture was washed with a saturated aqueous solution of sodium hydrogen carbonate and saturated saline. After drying the organic layer over anhydrous sodium sulfate, the solvent was concentrated under reduced pressure, and the obtained residue was purified by preparative thin-layer chromatography (ethyl acetate) to obtain the title compound (68 mg, 36%).

1H-NMR (CDCl3) δ: 8.63 (d, 1H, J = 4.3H
z), 7.33 (d, 1H, J = 4.1Hz), 4.33 (s, 2H), 2.91 (s, 3
H), 0.44 (s, 9H). (Reference Example 62) 2-trifluoromethyl-imidazo [1,2-α] pyrazine-3-carboxylic acid ethyl ester 4,4,4-trifluoro-3-oxo- Ethyl butanoate 2.40 ml (16.3 mmol) was dissolved in a mixed solvent of carbon tetrachloride and water (v / v = 1/1, 80 ml) and cooled to 0 ° C. 0.84 ml (16.3 mmol) of bromine in 1
The mixture was added dropwise over 5 minutes and stirred at room temperature for 1 hour. After separating the reaction solution into a carbon tetrachloride layer and an aqueous layer, the carbon tetrachloride layer was concentrated under reduced pressure (25 ° C., 16 mmHg), and the residue (2-bromo-4,4,4,4) was obtained.
-Trifluoro-3-oxo-butanoic acid ethyl ester)
2.66 g were obtained. The residue was used for the next reaction without purification.

To a solution of 1.50 g (15.8 mmol) of 2-aminopyrazine in 30 ml of dimethoxyethane was added 1.72 g (20.5 mmol) of sodium hydrogencarbonate, and the mixture was stirred at room temperature for 15 minutes. Bromo-4,4,4-trifluoro-3-oxo-butanoic acid ethyl ester) 2.6
6 g was added dropwise, and the mixture was stirred at 70 ° C. for 3 hours. The reaction solution was concentrated under reduced pressure and dissolved in dichloromethane. The organic layer was washed with saturated saline, dried over anhydrous sodium sulfate, and the solvent was concentrated under reduced pressure. The obtained residue was purified by column chromatography (ethyl acetate: hexane = 9: 1) to obtain 0.89 g (22%) of the title compound.

1H-NMR (CDCl3) δ: 9.34 (d, 1H, J = 1.4H
z), 9.27 (dd, 1H, J = 1.6Hz, 4.6Hz), 8.26 (d, 1H, J =
4.6Hz), 4.51 (q, 2H, J = 7.1Hz), 1.46 (t, 3H, J = 7.0H
(Reference Example 63) Trifluoromethyl-imidazo [1,2-α] pyrazine-3-carboxylic acid methoxy-methyl-amide Using the compound of Reference Example 62, a reaction was carried out in the same manner as in Reference Example 8, The title compound was obtained.

1H-NMR (CDCl3) δ: 9.26 (d, 1H, J = 1.6H
z), 8.30 (dd, 1H, J = 1.6Hz, 4.9Hz), 8.10 (d, 1H, J =
(4.9Hz), 3.52 (s, 3H), 3.48 (s, 3H). (Reference Example 64) 2-bromo-1- (2-trifluoromethyl-imidazo [1,2-α]
Pyrazin-3-yl) -ethanone Using the compound of Reference Example 63, a reaction was carried out in the same manner as in Reference Example 9 to obtain the title compound.

1H-NMR (CDCl3) δ: 9.45 (dd, 1H, J = 1.6
Hz, 4.6Hz), 9.42 (d, 1H, J = 5.1Hz), 8.39 (d, 1H, J =
(4.6 Hz), 4.65 (s, 2H). (Reference Example 65) 1.02 ml of 1- (2-methyl-imidazo [1,2-α] pyrazin-3-yl) -ethanone pentane-2,4-dione ( 9.99 mmol) in a mixed solvent of carbon tetrachloride and water (v / v = 1 / 1,80 m
1) and cooled to 0 ° C. 0.52 ml of bromine
(9.99 mmol) was added dropwise over 5 minutes, and the mixture was stirred at room temperature for 1 hour. After separating the reaction solution into a carbon tetrachloride layer and an aqueous layer, the carbon tetrachloride layer was concentrated under reduced pressure (25 ° C, 16 mmH
g), residue (3-bromo-pentane-2,4-dione) 1.0
2 g were obtained.

To a solution of 1.27 g (13.4 mmol) of 2-aminopyrazine in 10 ml of dimethoxyethane was added 1.15 g (13.7 mmol) of sodium hydrogencarbonate, and the mixture was stirred at room temperature for 15 minutes. Bromo-pentane-
2,4-dione) was added dropwise, and the mixture was stirred at 70 ° C. for 3 hours. The reaction solution was concentrated under reduced pressure and dissolved in dichloromethane. The organic layer was washed with saturated saline, dried over anhydrous sodium sulfate,
The solvent was concentrated under reduced pressure. The obtained residue is purified by column chromatography (ethyl acetate: methanol = 9:
1), 0.14 g (7.6%) of the title compound.

1H-NMR (CDCl3) δ: 9.52 (dd, 1H, J = 1.4
Hz, 4.6Hz), 9.15 (d, 1H, J = 1.1Hz), 8.14 (d, 1H, J =
(4.6Hz), 2.86 (s, 3H), 2.68 (s, 3H). (Reference Example 66) 2-bromo-1- (2-methyl-imidazo [1,2-α] pyrazin-3-yl) -ethanone Using the compound of Reference Example 65, a reaction was carried out in the same manner as in Reference Example 1 (2) to obtain the title compound.

1H-NMR (CDCl3) δ: 9.49 (dd, 1H, J = 1.4
Hz, 4.6Hz), 9.19 (s, 1H), 8.21 (d, 1H, J = 4.6Hz),
4.39 (s, 2H), 2.92 (s, 3H). (Reference Example 67) Bromo-1- (6-methyl-imidazo [1,2-α] thiazole-5-
Yl) -ethanone 1- (6-methyl-imidazo [1,2-α] thiazol-5-yl) -ethanone (J. Heterocycl. Chem .; FR; 16; 1979; 1201-1207)
Was used to carry out a reaction in the same manner as in Reference Example 1 (2) to obtain the title compound.

1H-NMR (CDCl3) δ: 8.40 (d, 1H, J = 4.6H
z), 6.98 (d, 1H, J = 4.6Hz), 4.29 (s, 2H), 2.76 (s, 3
H) (Reference Example 68) 6-chloro-2-trifluoro-imidazo [1,2-α] pyridine-3
-Carboxylic acid ethyl ester 15.0 g (81.7 mmol) of 4,4,4-trifluoro-3-oxo-butylic acid ethyl ester in water 4
0 ml and 40 ml of carbon tetrachloride. 4.2m of bromine
1 (81.7 mmol) in 10 ml of carbon tetrachloride solution was added dropwise over 1 hour at room temperature, followed by stirring at the same temperature for 1 hour. After the reaction solution was diluted with dichloromethane, it was washed with water and then with saturated saline. After drying the organic layer over anhydrous sodium sulfate,
The solvent was concentrated under reduced pressure, and the obtained residue was treated with dimethoxyethane 1
Dissolved in 00 ml. 8.75 g (68.1 mmol) of 5-chloro-pyridin-2-ylamine and 5.72 g (68.1 mmol) of sodium hydrogen carbonate were added, and the mixture was heated under reflux for 14 hours. After cooling, the reaction solution was diluted with ethyl acetate and washed with water and saturated saline. After the organic layer was dried over anhydrous sodium sulfate, the solvent was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography (hexane / ethyl acetate = 2:
Purified in 1). The obtained crystals were pulverized finely and washed with hexane-ethyl acetate to obtain 7.76 g (yield 39%) of the title compound.

1H-NMR (CDCl3) δ: 9.51 (dd, 1H, J = 0.8
Hz, 1.9Hz), 7.76 (dd, 1H, J = 0.8Hz, 9.5Hz), 7.50 (d
t, 1H, J = 1.9Hz, 9.5Hz), 4.48 (q, 2H, J = 7.0Hz), 1.4
4 (t, 3H, J = 7.0Hz); MS (APCI, m / z): 293 (M + H) +, 295 (M + H) +; HPLC (R): Rt = 5.4 min. (Reference example) 69) 6-Chloro-2-trifluoro-imidazo [1,2-α] pyridine-3
-Carboxylic acid methoxy-methyl-amide The compound obtained in Reference Example 68 was reacted in the same manner as in Reference Example 8 to obtain the title compound.

1H-NMR (CDCl3) δ: 8.46 (d, 1H, J = 1.4H
z), 7.69 (d, 1H, J = 9.7Hz), 7.38 (dd, 1H, J = 1.9Hz,
9.7Hz), 3.53 (s, 3H), 3.47 (s, 3H); MS (APCI, m / z): 308 (M + H) +, 310 (M + H) +; HPLC (R): Rt = 4.1 min. (Reference Example 70) 2-bromo-1- (6-chloro-2-trifluoro-imidazo [1,2-
α] pyridin-3-yl) -ethanone The compound obtained in Reference Example 69 was reacted in the same manner as in Reference Example 9 using methylmagnesium bromide instead of ethylmagnesium bromide in Reference Example 9 to give the title compound. Obtained.

1H-NMR (CDCl3) δ: 9.78 (d, 1H, J = 1.9
Hz), 7.84 (d, 1H, J = 9.5Hz), 7.63 (dd, 1H, J = 1.9Hz,
9.5 Hz), 4.63 (s, 2H); MS (APCI, m / z): 341 (M + H) +, 343 (M + H) +; HPLC (R): Rt = 5.2 min. (Reference Example 71) ) 6-methyl-2-trifluoro-imidazo [1,2-α] pyridine-3
-Carboxylic acid ethyl ester Reference Example 68 using 5-methyl-pyridin-2-ylamine
The reaction was carried out in the same manner as in to give the title compound.

1H-NMR (CDCl3) δ: 9.23 (d, 1H, J = 1.1H
z), 7.72 (d, 1H, J = 9.5Hz), 7.37 (dd, 1H, J = 1.6Hz,
9.2Hz), 4.46 (q, 2H, J = 7.0Hz), 2.45 (s, 3H), 1.44
(t, 3H, J = 7.0Hz); MS (APCI, m / z): 273 (M + H) +; HPLC (R): Rt = 5.1 min. (Reference Example 72) 6-methyl-2-tri Fluoro-imidazo [1,2-α] pyridine-3
-Carboxylic acid methoxy-methyl-amide The compound obtained in Reference Example 71 was reacted in the same manner as in Reference Example 8 to give the title compound.

1H-NMR (CDCl3) δ: 8.16 (s, 1H), 7.63
(d, 1H, J = 9.5Hz), 7.25 (d, 1H, J = 9.5Hz), 3.53 (s,
3H), 3.46 (s, 3H), 2.36 (s, 3H); MS (APCI, m / z): 288 (M + H) +; HPLC (R): Rt = 3.7 min. (Reference Example 73) 2 -Bromo-1- (6-methyl-2-trifluoro-imidazo [1,2-
α] pyridin-3-yl) -ethanone The compound obtained in Reference Example 72 was reacted in the same manner as in Reference Example 1 (2) to obtain the title compound.

1H-NMR (CDCl3) δ: 9.53 (d, 1H, J = 0.8H
z), 7.78 (d, 1H, J = 8.9Hz), 7.51 (dd, 1H, J = 1.6Hz,
8.9 Hz), 4.64 (s, 2H), 2.47 (s, 3H); MS (APCI, m / z): 321 (M + H) +, 323 (M + H) +; HPLC (R): Rt = 4.9 min. (Reference Example 74) 3-acetyl-2-methyl-imidazo [1,2-α] pyridine-6-carboxylic acid amide 4,4,4-trifluoro-3-oxo-butyric acid of Reference Example 68 The reaction was carried out in the same manner as in Reference Example 68 using acetylacetone in place of ethyl ester and 6-amino-nicotinamide in place of 5-chloro-pyridin-2-ylamine to obtain the title compound.

1H-NMR (DMSO-d6) δ: 10.12 (dd, 1H, J =
0.8Hz, 1.9Hz), 8.24 (brs, 1H), 7.99 (dd, 1H, J = 1.6
Hz, 9.2Hz), 7.73 (dd, 1H, J = 0.8Hz, 9.2Hz), 7.65 (b
rs, 1H), 2.75 (s, 3H), 2.61 (s, 3H); MS (APCI, m / z): 218 (M + H) +; HPLC (R): Rt = 2.0 min. (Reference Example 75 3) 3- (2-Bromo-acetyl) -2-methyl-imidazo [1,2-α] pyridine-6-carboxylic acid amide The compound obtained in Reference Example 74 was reacted in the same manner as Reference Example 1 (2). To give the title compound.

1H-NMR (DMSO-d6) δ: 10.12 (dd, 1H, J =
0.8Hz, 1.9Hz), 8.29 (brs, 1H), 8.05 (dd, 1H, J = 1.6
Hz, 9.2Hz), 7.79 (dd, 1H, J = 1.1Hz, 9.2Hz), 7.67 (b
rs, 1H), 4.81 (s, 2H), 2.79 (s, 3H); MS (APCI, m / z): 296 (M + H) +, 298 (M + H) +; HPLC (R): Rt = 2.6 min. (Reference Example 76) 1- (2-Methyl-6-nitro-imidazo [1,2-α] pyridin-3-yl) -ethanone Example 74
The reaction was carried out in the same manner as in to give the title compound.

1H-NMR (DMSO-d6) δ: 10.53 (dd, 1H, J =
0.8Hz, 2.4Hz), 8.27 (dd, 1H, J = 0.8Hz, 9.7Hz), 7.86
(dd, 1H, J = 0.5Hz, 9.7Hz), 2.79 (s, 3H), 2.66 (s,
3H); MS (APCI, m / z): 296 (M + H) +, 220 (M + H) +; HPLC (R): Rt = 3.4 min. (Reference Example 77) 2-bromo-1- ( 2-Methyl-6-nitro-imidazo [1,2-α] pyridin-3-yl) -ethanone The compound obtained in Reference Example 76 was reacted in the same manner as in Reference Example 1 (2) to obtain the title compound. Was.

1H-NMR (DMSO-d6) δ: 10.50 (dd, 1H, J =
0.8Hz, 2.4Hz), 8.33 (dd, 1H, J = 2.4Hz, 9.7Hz), 7.91
(dd, 1H, J = 0.8Hz, 9.7Hz), 4.90 (s, 2H), 2.84 (s,
3H); MS (APCI, m / z): 298 (M + H) +, 300 (M + H) +; HPLC (R): Rt = 3.9 min. (Reference Example 78) N- (5-methyl- Pyridin-2-yl) -oxamic acid methyl ester 5-methyl-pyridin-2-ylamine 8.00 g (74.0
(Mmol) was dissolved in 80 ml of dichloromethane, and the mixture was cooled with ice in a stream of nitrogen. Chloro-oxo-acetic acid
10.0 g (82.0 mmol) of methyl ester was added to 2
After the dropwise addition in 0 minutes, the temperature was naturally raised to room temperature with the ice bath kept on, followed by stirring for 2 hours. The solvent was concentrated under reduced pressure, diethyl ether was added to the obtained residue, and the precipitated crystals were collected by filtration. The crystals were suspended in ethyl acetate and washed with a saturated aqueous solution of sodium bicarbonate and subsequently with a saturated saline solution. After the organic layer was dried over anhydrous sodium sulfate, the solvent was concentrated under reduced pressure. The obtained crystals were finely pulverized and washed with ethyl acetate to obtain 6.1 g (yield 42%) of the title compound.

1H-NMR (CDCl3) δ: 9.40-9.20 (brs, 1
H), 8.25-8.05 (m, 2H), 7.58 (d, 1H, J = 8.4), 3.98
(s, 3H), 2.34 (s, 3H); MS (APCI, m / z): 195 (M + H) +; HPLC (R): Rt = 3.1 min. (Reference Example 79) 3-acetyl-6 -Methyl-imidazo [1,2-α] pyridine-2-carboxylic acid methyl ester The compound obtained in Reference Example 78 was reacted in the same manner as in Reference Example 38 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 9.26 (s, 1H), 7.7
7 (d, 1H, J = 9.2), 7.57 (d, 1H, J = 8.9), 3.96 (s, 3
H), 2.56 (s, 3H), 2.40 (s, 3H); MS (APCI, m / z) 233 (M + H) +; HPLC (R): Rt = 3.6 min. (Reference Example 80) 3- (2-Bromo-acetyl) -6-methyl-imidazo [1,2-α] pyridine-2-carboxylic acid methyl ester The compound obtained in Reference Example 79 was reacted in the same manner as in Reference Example 28 to give the title compound I got

1H-NMR (DMSO-d6) δ: 9.20 (s, 1H), 7.84
(d, 1H, J = 9.2), 7.62 (d, 1H, J = 9.2), 4.84 (s, 2
H), 3.96 (s, 3H), 2.42 (s, 3H); MS (APCI, m / z): 311 (M + H) +, 313 (M + H) +; HPLC (R): Rt = 4.2 min. (Reference Example 81) 2-Isopropyl-6-methyl-imidazo [1,2-α] pyridine-3
-Carboxylic acid ethyl ester Same as Reference Example 68, except that 4,4,4-trifluoro-3-oxo-butylic acid ethyl ester of Reference Example 68 was replaced with 4-methyl-3-oxo-pentanoic acid methyl ester. To give the title compound.

1H-NMR (DMSO-d6) δ: 9.08 (s, 1H), 7.64
(d, 1H, J = 8.9), 7.40 (d, 1H, J = 9.2), 4.37 (q, 2H,
J = 7.0), 3.74 (sep, 1H, J = 6.8), 2.37 (s, 3H), 1.36
(t, 3H, J = 7.0), 1.28 (d, 6H, J = 7.0); MS (APCI, m / z): 247 (M + H) +; HPLC (R): Rt = 3.5 min. (reference Example 82) 2-Isopropyl-6-methyl-imidazo [1,2-α] pyridine-3
-Carboxylic acid methoxy-methyl-amide The compound obtained in Reference Example 81 was reacted in the same manner as in Reference Example 8 to obtain the title compound.

1H-NMR (DMSO-d6) δ: 8.23 (s, 1H), 7.52
(d, 1H, J = 9.2), 7.11 (d, 1H, J = 9.2), 3.54 (s, 3
H), 3.43 (s, 3H), 3.32 (sep, 1H, J = 6.8), 2.32 (s,
3H), 1.36 (d, 6H, J = 7.0); MS (APCI, m / z): 262 (M + H) +; HPLC (R): Rt = 2.5 min. (Reference Example 83) 2-bromo- 1- (2-isopropyl-6-methyl-imidazo [1,2-
α] pyridin-3-yl) -ethanone The compound obtained in Reference Example 82 was reacted in the same manner as in Reference Example 9 using methylmagnesium bromide instead of ethylmagnesium bromide in Reference Example 9 to give the title compound. Obtained.

1H-NMR (CDCl3) δ: 9.58 (s, 1H), 7.62
(d, 1H, J = 8.9), 7.36 (d, 1H, J = 9.2), 4.43 (s, 2H),
3.55 (sep, 1H, J = 6.8), 2.41 (s, 3H), 1.48 (d, 6H,
J (6.8); MS (APCI, m / z): 295 (M + H) +, 296 (M + H) +; HPLC (R): Rt = 4.0 min. (Reference Example 84) (6-hydroxy- (Pyridin-3-yl) -thiourea (1) 5-amino-pyridin-2-ol 5-nitro- dissolved in 20 ml of methanol under a hydrogen stream
1.00 g (7.14 mmol) of pyridin-2-ol
Was added with 10% Pd-C (570 mg), and the mixture was stirred at room temperature for 3 hours. The reaction solution was filtered through celite, and the filtrate was concentrated under reduced pressure to give 0.939 g (94%) of 5-amino-pyridin-2-ol.
I got 1H-NMR (DMSOd-6) δ: 7.05 (dd, 1H, J = 3.0Hz, 9.5Hz),
6.74 (d, 1H, J = 3.0Hz), 6.22 (d, 1H, J = 9.2Hz), 4.2
5 (brs, 2H); MS (APCI, m / z): 111 (M + H) +; HPLC (R): Rt = 0.78 min. (2) 1-benzoyl-3- (6-hydroxy-pyridine- The same reaction as in Reference Example 2 (1) was carried out using 0.74 g (6.72 mmol) of 3-yl) -thiourea 5-amino-pyridin-2-ol to obtain 1.16 g (63%) of the title compound. I got 1H-NMR (DMSOd-6) δ: 12.01 (s, 1H), 11.65 (s, 1H),
7.97 (d, 2H, J = 7.3Hz), 7.68-7.51 (m, 6H), 6.36
(d, 1H, J = 10.0Hz); MS (APCI, m / z): 274 (M + H) +; HPLC (R): Rt = 3.1 min. (3) (6-hydroxy-pyridine-3- Yl) -thiourea Using 0.800 g (2.93 mmol) of 1-benzoyl-3- (6-hydroxy-pyridin-3-yl) thiourea,
The reaction was carried out in the same manner as in Reference Example 2 (2), and the title compound 0.1
75 g (28%) were obtained. 1H-NMR (DMSOd-6) δ: 7.89 (d, 1H, J = 7.0Hz), 7.64 (b
rs, 1H), 7.37 (brs, 1H), 7.34 (dd, 2H, J = 3.0Hz, 7.8
Hz), 6.27 (dd, 1H, J = 3.0Hz, 7.6Hz); MS (APCI, m / z): 170 (M + H) +; HPLC (R): Rt = 0.86 min. (Reference Example 85) Reference Example 2 using (6-methyl-pyridin-3-yl) -thiourea 6-methyl-pyridin-3-yl-amine
And the title compound was obtained. 1H-NMR (DMSO-d6) δ 9.66 (brs, 1H), 8.38 (brs, 1
H), 7.76 (d, 1H, J = 8.1Hz), 7.20 (d, 1H, J = 8.1Hz),
2.43 (s, 3H); (Reference Example 86) (6-ethoxy-pyridin-3-yl) -thiourea A reaction was carried out in the same manner as in Reference Example 2 using (6-ethoxy-pyridin-3-yl) amine. The title compound was obtained. ¹ H-NMR (DMSO-d ₆ ) δ: 9.47 (s, 1H), 8.02 (s, 1H),
7.67 (d, 1H, J = 8.9Hz), 7.65-7.10 (brs, 2H), 6.76
(d, 1H, J = 9.5Hz), 4.27 (q, 2H, J = 7.0Hz), 1.31 (t, 3
(H, J = 6.8 Hz); (Reference Example 87) (2,3-dihydro-benzo [1,4] dioxin-6-yl) -thiourea (2,3-dihydro-benzo [1,4] dioxin-6) The reaction was carried out in the same manner as in Reference Example 2 using (-yl) amine to obtain the title compound. ¹ H-NMR (DMSO-d ₆ ) δ: 9.65 (s, 1H), 7.60-7.20 (br,
2H), 6.93 (s, 1H), 6.80 (d, 2H, J = 8.6Hz), 6.73 (d,
(2H, J = 8.6Hz), 4.30-4.10 (br, 4H); (Reference Example 88) Using (3,4,5-trimethoxy-phenyl) -thiourea (3,4,5-trimethoxy-phenyl) amine The reaction was carried out in the same manner as in Reference Example 2 to obtain the title compound. ¹ H-NMR (DMSO-d ₆ ) δ: 9.71 (s, 1H), 7.80-7.20 (br,
(2H), 6.72 (s, 1H), 3.74 (s, 6H), 3.63 (s, 3H); (Reference Example 89) 5-acetoxy-pentanoic acid 1) 5-hydroxy-pentanoic acid benzyl
3.62 g (17.4 mmol) of the ester was added to pyridine 1
The residue was dissolved in 5 ml, acetic anhydride (3 ml) was added, and the mixture was stirred at room temperature for 14 hours. The reaction solution was concentrated under reduced pressure, ethyl acetate was added to the obtained residue, and the mixture was washed with a 10% aqueous hydrochloric acid solution, a saturated aqueous sodium hydrogen carbonate solution, and a saturated saline solution. After the organic layer was dried over anhydrous sodium sulfate, the solvent was concentrated under reduced pressure to obtain 4.07 g of 5-acetoxy-pentanoic acid benzyl ester. 2) Reference Example 89 4.07 g of 5-acetoxy-pentanoic acid benzyl ester obtained in 1) was dissolved in 40 ml of ethyl acetate, and 10% palladium-carbon 40 was added.
0 mg was added and the mixture was stirred under hydrogen pressure for 4 hours. The reaction solution was filtered through celite, and the filtrate was concentrated under reduced pressure to obtain 2.66 g of 5-acetoxy-pentanoic acid. ¹ H-NMR (CDCl ₃ ) δ: 4.09 (t, 2H, J = 5.9Hz), 2.41 (t,
(2H, J = 7.0Hz), 2.06 (s, 3H), 1.76-1.70 (m, 4H); (Reference Example 90) 5- (2-tert-butoxycarbonyl-acetoxy) -pentanoic acid N- (tert-butoxy) 3.03 g of carbonyl) glycine
(17.3 mmol) in anhydrous tetrahydrofuran 30 m
and N, N-carbonyldiimidazole (2.81 g, 17.3 mmol) was added at room temperature, followed by stirring for 30 minutes. 3.00 g (14.4 mmol) of 5-hydroxy-pentanoic acid benzyl ester was added,
Stir for 15 hours. The reaction solution was concentrated under reduced pressure, ethyl acetate was added to the obtained residue, and the mixture was washed with a 5% aqueous potassium hydrogen sulfate solution, a saturated aqueous sodium hydrogen carbonate solution, and then with a saturated saline solution. After the organic layer was dried over anhydrous sodium sulfate, the solvent was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane / ethyl acetate = 2: 1) to give 5- (2-t
4.62 g (88%) of ert-butoxycarbonyl-acetoxy) -pentanoic acid ester was obtained. Reference Example 90 The 5- (2-tert-butoxycarbonyl-acetoxy) -pentanoic acid benzyl ester obtained in 1) was referred to. The reaction was carried out in the same manner as in Example 89 2) to give the title compound. ¹ H-NMR (CDCl ₃ ) δ: 5.03 (brs, 1H), 4.20-4.14 (m, 2
H), 3.90 (d, 2H, J = 5.7Hz), 2.43-2.38 (m, 2H), 1.75
-1.70 (m, 4H), 1.45 (s, 9H); (Reference Example 91) Using 4-acetoxy-butylic acid 4-hydroxy-butylic acid benzyl ester, the reaction was carried out in the same manner as in Reference Example 89 to obtain the title compound Was. ¹ H-NMR (CDCl ₃ ) δ: 4.13 (t, 2H, J = 6.2Hz), 2.47 (t,
(2H, J = 7.0Hz), 2.06 (s, 3H), 2.05-1.80 (m, 2H); (Reference Example 92) 5- (2-tert-butoxycarbonyl- (s) amino-propionyloxy) -pentanoic acid The same reaction as in Reference Example 90 was carried out using 5-hydroxy-pentanoic acid benzyl ester and N- (tert-butoxycarbonyl) -L-alanine to obtain the title compound. ¹ H-NMR (CDCl ₃ ) δ: 5.08 (brs, 1H), 4.35-4.25 (m, 1
H), 4.18-4.26 (m, 2H), 2.43-2.36 (m, 2H), 1.75-1.68
(m, 4H), 1.45 (s, 9H), 1.38 (d, 3H, J = 7.0 Hz); (Reference Example 93) (6-trifluoromethyl-pyridin-3-yl) -thiourea 6-trifluoromethyl The reaction was carried out in the same manner as in Reference Example 2 using -pyridin-3-ylamine to obtain the title compound. ¹ H-NMR (CDCl ₃ ) δ: 10.16 (brs, 1H), 8.78 (d, 1H, J
= 2.4Hz), 8.36 (dd, 1H, J = 1.9Hz, 7.8Hz), 8.78 (d, 1
(Reference Example 94) 2-bromo-1- (2-methyl-8-nitro-imidazo [1,2-α] pyridin-3-yl) -ethanone 1) 1- ( 2-methyl-8-nitro-imidazo [1,2-α] pyridine-
3-yl) -ethanone 12.6 ml (122 mmol) of 2,4-dione was dissolved in 200 ml of carbon tetrachloride-water (1: 1), and 6,29 ml (122 mmol) of bromine was added to 10 ml of carbon tetrachloride under ice age.
Was added dropwise over 1 hour, followed by stirring at room temperature for 30 minutes. The reaction solution was diluted with dichloromethane and washed with water and saturated saline. After the organic layer was dried over anhydrous sodium sulfate, the solvent was concentrated under reduced pressure, and the residue and 10.0 g (71.9 mmol) of 2-amino-nitropyridine were dissolved in 100 ml of dimethoxyethane, and sodium hydrogencarbonate 6.0 was dissolved.
4 g (71.9 mmol) was added and the mixture was stirred at 70 ° C. for 16 hours. After cooling, the reaction solution was diluted with ethyl acetate and washed with water and saturated saline. After the organic layer was dried over anhydrous sodium sulfate, the solvent was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate) to give 1- (2-methyl-
1.48 g (yield 9%) of 8-nitro-imidazo [1,2-α] pyridin-3-yl) -ethanone was obtained. 1H-NMR (CDCl3) δ: 10.09 (d, 1H, J = 6.8Hz), 8.39
(d, 1H, J = 7.6Hz), 7.16 (t, 1H, J = 6.8Hz), 2.93 (s,
3H), 2.70 (s, 3H); MS (APCI, m / z): 220 (M + H) +; HPLC (R): Rt. = 2.9 min. 2) 2-bromo-1- (2-methyl) -8-nitro-imidazo [1,2-α]
Pyridin-3-yl) -ethanone 481 mg (2.19 mmol) of 1- (2-methyl-8-nitro-imidazo [1,2-α] pyridin-3-yl) -ethanone was 47%-
After dissolving in 5 ml of hydrobromic acid and heating to 70 ° C.,
μl (3.80 mmol) of a 48% solution of hydrobromic acid in 2 ml were added dropwise over 1 hour. The reaction solution was added little by little to about 100 ml of a saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over anhydrous sodium sulfate, and the solvent was concentrated under reduced pressure. The obtained crude crystals were finely ground and washed with hexane-ethyl acetate to obtain 636 mg (97%) of the title compound. 1H-NMR (DMSO-d6) δ: 9.88 (dd, 1H, J = 1.1Hz, 6.8H
z), 8.56 (dd, 1H, J = 1.1Hz, 7.8Hz), 7.43 (t, 1H, J =
7.8Hz), 4.88 (s, 2H), 3.32 (s, 3H), 2.87 (s, 3H); MS (APCI, m / z): 298 (M + H) +, 300 (M + 1) +; HPLC (R): Rt. = 3.5 min. (Formulation Example 1) (Hard Capsule) 100 mg in each of standard two-piece hard gelatin capsules
Powdered compound of Example 1, 150 mg lactose,
A unit capsule is prepared by filling 50 mg of cellulose and 6 mg of magnesium stearate, washing and drying. Formulation Example 2 (Soft Capsule) A mixture of the compound of Example 2 in a digestible oil, such as soybean oil, cottonseed oil or olive oil, is prepared and injected into gelatin with a positive displacement pump. Thus, a soft capsule containing 100 mg of the active ingredient is obtained, washed and dried. (Formulation Example 3) (Tablet) According to a conventional method, 100 mg of the compound of Example 3, 0.2 mg
Of colloidal silicon dioxide, 5 mg of magnesium stearate, 275 mg of microcrystalline cellulose, 11 mg of starch and 98.8 mg of lactose.

[0716] If desired, a coating is applied. Formulation Example 4 (Injection) 1.5% by weight of the compound of Example 4 was stirred in 10% by volume of propylene glycol, made up to a constant volume with water for injection, and then sterilized. I do. (Formulation Example 5) (Suspension) 100 mg of the finely divided compound of Example 5 in 5 ml,
100 mg of sodium carboxymethyl cellulose, 5
mg sodium benzoate, 1.0 g sorbitol solution
(Japanese Pharmacopoeia) and 0.025 ml of vanillin. Formulation Example 6 (Cream) 40% white petrolatum, 3% microcrystalline wax, 10% lanolin, 5% span 20, 0.3% tween 20 and 41.7% 5g of clean water
It is prepared by incorporating 100 mg of the finely divided compound of Example 6 into a system. Formulation Example 7 (Cream) Compound of Example 7 (2 parts by weight), 1,2-propanediol (5 parts by weight), glycerol stearate (5 parts by weight), spermaceti (5 parts by weight) Parts by weight), a mixture of isopropyl myristate (10 parts by weight) and polysorbate (4 parts by weight) was heated, cooled, and then, with stirring, water (69 parts by weight) was added thereto. To manufacture. (Formulation Example 8) (Solution for application) The compound of Example 8 (1 part by weight) and polyethylene glycol 300 (99 parts by weight) are mixed to prepare a solution for cloth. (Formulation Example 9) (Ointment) Compound of Example 9 (2 parts by weight), polyethylene glyco-
400 (40 parts by weight), polyethylene glycol 15
After mixing and dissolving 00 (58 parts by weight) under heating, the mixture is cooled to produce an ointment. (Test Example 1) Cytotoxicity test for various cancer cells HL-60 (Dainippon Pharmaceutical CCL-24) as a cancer cell line
0), HeLa (ATCC CCL-2), U937
(ATCC CRL-1593), CaSki (ATC
C CRL-1550) was used. The culture medium used was the following medium supplemented with 10% fetal bovine serum (manufactured by Hyclone). HL-60, U937: RPMI
1640 medium (manufactured by Asahi Glass Co., Ltd.), CaSki: MEM medium (manufactured by Gibco), HeLa: DMEM medium (manufactured by Gibco) First, the compounds of Examples 3, 269, and 280 were dissolved in dimethyl sulfoxide. 10mg /
A ml solution was made. This solution was diluted with RPMI1640 medium containing 10% fetal bovine serum to prepare a 4-fold serial dilution, which was added to a 96-well flat bottom plate (Corning Costar 3598) at 50 μl / well. 3 dispensed. At this time, the final concentration of dimethyl sulfoxide was controlled not to exceed 0.5%. Further, a liquid obtained by suspending each cancer cell line at a density of 40,000 cells / ml in each culture medium was dispensed at 150 μl / well, and cultured under 5% CO 2 and 37 ° C. for 72 hours.
After completion of the culture, an XTT / PMS solution (1 mg / ml 2,3
50 μl of -bis [2-methoxy-4-nitro-5-sulfophenyl] -2H-tetrazolium-5-carboxanilide (Sigma), 25 mM phenazine / methosulfate (Sigma) dissolved in a culture solution.
Per well and incubating at 37 ° C. for 2-4 hours, using a plate reader (Spectra Max 250,
The absorbance at 450 nm was measured using Molecular Devices, Inc., and the percentage of living cells (%) was calculated based on the following equation.

Percentage of viable cells (%) = (absorbance of well with addition of specimen / cell−absorbance of well without addition of cell) × 10
0 / (absorbance of wells with no sample added / cells-absorbance of wells with no cells added).

Finally, a graph was prepared in which the logarithm of the concentration and the percentage of living cells were plotted, and the concentration that reduced the percentage of living cells by 50% (hereinafter referred to as “ED50 value”) was determined and used as an index of cytotoxicity.

[0719]

[Table 6] ---------------------------------------------- -------- Example No.Cell line ED50 (ng / mg) ------------------------------- ----------------------- 3 Hela 1.8 U-937 1.2 CaSki 1.6 HL-60 20 269 Hela 4.8 U-937 4.5 CaSki 5.8 HL-60 4.9 280 Hela 49 U-937 49 CaSki 72 HL-60 80 ------------------------ ------------------------------

[0720]

The compound of the present invention has excellent tumor growth inhibitory activity and is therefore useful as a prophylactic or therapeutic agent for cancer.

 ──────────────────────────────────────────────────続 き Continuing from the front page (72) Inventor Toshinori Agatsuma 1-2-58 Hiromachi, Shinagawa-ku, Tokyo Inside Sankyo Co., Ltd. (72) Inventor Hidehiko Furukawa 1-2-2 Hiromachi, Shinagawa-ku, Tokyo No. 58 Sankyo Co., Ltd. (72) Inventor Shunji Narito 1-2-58 Hiromachi, Shinagawa-ku, Tokyo, Japan No. 58 Sanko Co., Ltd. (72) Inventor Shinichi Kurata 1-2-58, Hiromachi, Shinagawa-ku, Tokyo No. F term in Sankyo Co., Ltd. (reference) 4C065 AA03 BB06 CC01 DD02 EE02 HH01 JJ01 KK07 LL01 PP17 4C086 AA01 AA03 CB05 MA01 MA04 NA14 ZB21 ZB26

Claims (35)

[Claims] 1. A compound of the general formula [Wherein, R ¹ and R ² are the same or different and have the formula R ⁹ -X ²
A group (wherein R ⁹ is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkyl group having 1 to 6 carbon atoms substituted by 1 to 3 substituents selected from the following α group, 3 To an 8-membered cycloalkyl group, a substituent selected from the following β group:
A 3- to 8-membered cycloalkyl group substituted with 3 to 8 members, an aryl group having 6 to 14 carbon atoms, an aryl group having 6 to 14 carbon atoms substituted with 1 to 5 substituents selected from the following β group, A heterocyclic group, a substituent selected from the following β group:
Heterocyclic group substituted with 5 to 5 carbon atoms, aralkyl group having 7 to 15 carbon atoms, aralkyl group having 7 to 15 carbon atoms substituted with 1 to 5 substituents selected from the following β group, and 8 carbon atoms
To 16 arylalkenyl groups, an arylalkenyl group having 8 to 16 carbon atoms substituted by 1 to 5 with a substituent selected from the following β group, or a carbamoyl group, and X ² represents a single bond, carbonyl Group (-C (= O)
—), An oxycarbonyl group (—OC (＝ O) —), an aminocarbonyl group (—NHC (＝ O) —) or a sulfonyl group (—SO ₂ —). Wherein R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ are the same or different and are each a halogen atom, a cyano group, a nitro group, a formula R ¹⁰ -X ³
A group (wherein, R ¹⁰ is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkyl group having 1 to 6 carbon atoms substituted by 1 to 3 with a substituent selected from the following α group, 3 to 3 8-membered cycloalkyl group, 3- to 8-membered cycloalkyl group substituted by 1 to 3 with a substituent selected from the following β group, aryl group having 6 to 14 carbon atoms, substitution selected from the following β group An aryl group having 6 to 14 carbon atoms, a heterocyclic group substituted with 1 to 5 carbon atoms, a heterocyclic group substituted with 1 to 5 carbon atoms, and an aralkyl having 7 to 15 carbon atoms. A aralkyl group having 7 to 15 carbon atoms, an arylalkenyl group having 8 to 16 carbon atoms substituted with 1 to 5 by a substituent selected from the following β group, or a substituent selected from the following β group 8 to 1 carbon atoms substituted by 1 to 5
X 6 represents an arylalkenyl group, and X ³ represents a single bond,
Oxygen atom (-O-), sulfur atom (-S-), carbonyl group (-C (= O)-), oxycarbonyl group (-OC
(= O)-), a carbonyloxy group (-C (= O) O
-), aminocarbonyl group (-NHC (= O) - shows a) -) or a sulfonyl group (-SO _2. ) Or formula R ¹¹
R ¹² N-group (wherein, R ¹¹ and R ¹² are the same or different and are each a group represented by the formula R ¹³ -X ⁴ (where R ¹³ is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkyl group having 1 to 6 carbon atoms substituted with 1 to 3 substituents selected from the α group, a 3 to 8 membered cycloalkyl group, and 1 to 3 substituted with a substituent selected from the following β group A 3- to 8-membered cycloalkyl group, an aryl group having 6 to 14 carbon atoms, the following β
6 carbon atoms substituted with 1 to 5 substituents selected from the group
To 14 aryl groups, heterocyclic groups, heterocyclic groups substituted by 1 to 5 substituents selected from the following β group, and carbon atoms of 7
To 15 aralkyl groups, an aralkyl group having 7 to 15 carbon atoms substituted by 1 to 5 with a substituent selected from the following β group, an arylalkenyl group having 8 to 16 carbon atoms,
Or an arylalkenyl group having 8 to 16 carbon atoms, which is substituted by 1 to 5 with a substituent selected from the following β group, wherein X ⁴ is a single bond, a carbonyl group (—C (＝ O)
—), An oxycarbonyl group (—OC (＝ O) —), an aminocarbonyl group (—NHC (＝ O) —) or a sulfonyl group (—SO ₂ —). ). ) Or R ³ ,
R ^4, R ⁷ and R ⁸ is a same meaning, or respectively R ⁵ and R ⁶ indicate a benzene ring which may have a substituent together with the carbon to which are attached, R ^3, R ^4, R ⁵ and R ⁸ is a same meaning, or respectively R ⁶ and R ⁷ shows a benzene ring which may have a substituent together with the carbon to which is attached, or, R ^3, R ⁴ , R ⁵ and R ⁶ have the same meaning and represent a benzene ring which may have a substituent together with R ⁷ and R ⁸ and the carbon to which each is bonded. X
¹ represents an oxygen atom, a sulfur atom, or a formula NH group. Provided that R ¹ , R ² , R ³ , R ⁵ , R ⁶ , R ⁷ and R ⁸ are hydrogen atoms, R ⁴ is a methyl group and X ¹ is a sulfur atom. Or a pharmacologically acceptable salt thereof. α group: a halogen atom, a cyano group, a nitro group, oxodioxolenyl methyl group, wherein R ¹⁴ -X ⁵ group (wherein, R ¹⁴ is
A hydrogen atom, an amino group, an alkyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms substituted by 1 to 3 with a substituent selected from the following γ group, and a 3- to 8-membered cycloalkyl group A 3- to 8-membered cycloalkyl group substituted by 1 to 3 with a substituent selected from Group δ below, and having 6 carbon atoms
To 14 aryl groups, an aryl group having 6 to 14 carbon atoms substituted with 1 to 5 substituents selected from the following δ group, a heterocyclic group, and 1 to 3 substituents selected from the following δ group. A substituted heterocyclic group, an aralkyl group having 7 to 15 carbon atoms, an aralkyl group having 7 to 15 carbon atoms substituted by 1 to 5 with a substituent selected from the following δ group, and an aralkyl group having 8 to 16 carbon atoms An arylalkenyl group or a C8 to C16 substituted with 1 to 5 substituents selected from the following δ group:
X ⁵ represents a single bond, an oxygen atom (—O—), a sulfur atom (—S—), a carbonyl group (—C (＝ O) —), an oxycarbonyl group (—OC ( =
O)-), a carbonyloxy group (-C (= O) O-),
It represents an aminocarbonyl group (—NHC (＝ O) —) or a sulfonyl group (—SO ₂ —). ) And the formula R ¹⁶ R ¹⁷ N
-A group wherein R ¹⁶ and R ¹⁷ are the same or different and
¹⁸ -X ⁶ groups (wherein, R ¹⁸ is a hydrogen atom, having 1 to 2 carbon atoms)
0 alkyl groups, 1 substituent group selected from the following γ group
3 to 3 substituted alkyl groups having 1 to 20 carbon atoms, 3
To an 8-membered cycloalkyl group, a 3- to 8-membered cycloalkyl group substituted by 1 to 3 with a substituent selected from the following group δ, an aryl group having 6 to 14 carbon atoms, selected from the following group δ 6 to 1 carbon atoms substituted by 1 to 5 substituents
4 aryl groups, heterocyclic groups, heterocyclic groups substituted with 1 to 5 substituents selected from the following δ group, and 7 to 1 carbon atoms
5 aralkyl groups, an aralkyl group having 7 to 15 carbon atoms substituted by 1 to 5 with a substituent selected from the following δ group, an arylalkenyl group having 8 to 16 carbon atoms, or selected from the following δ group Represents an arylalkenyl group having 8 to 16 carbon atoms, which is substituted with 1 to 5 substituents,
X ⁶ is a single bond, a carbonyl group (—C (＝ O) —), an oxycarbonyl group (—OC (＝ O) —), an aminocarbonyl group (—NHC (＝ O) —) or a sulfonyl group (—S
O _2- ) is shown. Or R ¹⁶ and R ¹⁷ are taken together with the nitrogen atom to be bonded to form a heterocyclic group or the following δ
A heterocyclic group substituted by 1 to 5 with a substituent selected from the group; However, the formula R ¹⁴ -X ⁵ does not represent an alkyl group having 1 to 6 carbon atoms. ). Group β: halogen atom, cyano group, nitro group, formula R ¹⁸ -X
⁷ groups (wherein, R ¹⁸ represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkyl group having 1 to 6 carbon atoms substituted by 1 to 3 substituents selected from the following γ group, 3 To an 8-membered cycloalkyl group, and 1
A 3- to 8-membered cycloalkyl group substituted with 3 to 8 members, an aryl group having 6 to 14 carbon atoms, an aryl group having 6 to 14 carbon atoms substituted with 1 to 5 substituents selected from the following group δ, A heterocyclic group, a substituent selected from the following δ group;
Heterocyclic group substituted with 5 to 5 carbon atoms, aralkyl group having 7 to 15 carbon atoms, aralkyl group having 7 to 15 carbon atoms substituted with 1 to 5 substituents selected from the following group δ, and 8 carbon atoms
Represents an arylalkenyl group having 1 to 16 carbon atoms or an arylalkenyl group having 8 to 16 carbon atoms substituted by 1 to 5 with a substituent selected from the following group δ, and X ⁷ represents a single bond, an oxygen atom (− O-), a sulfur atom (-S-), a carbonyl group (-C (= O)-), an oxycarbonyl group (-O
C (= O)-), carbonyloxy group (-C (= O) O
-), aminocarbonyl group (-NHC (= O) - shows a) -) or a sulfonyl group (-SO _2. ) And the formula R ¹⁹
R ²⁰ N-group (wherein, R ¹⁹ and R ²⁰ are the same or different and are each a group represented by formula R ²¹ -X ⁸ (wherein R ²¹ is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkyl group having 1 to 6 carbon atoms substituted with 1 to 3 substituents selected from the group γ, a 3- to 8-membered cycloalkyl group, and 1 to 3 substituted with a substituent selected from the following group δ A 3- to 8-membered cycloalkyl group, an aryl group having 6 to 14 carbon atoms,
6 carbon atoms substituted with 1 to 5 substituents selected from the group
To 14 aryl groups, heterocyclic groups, heterocyclic groups substituted with 1 to 5 substituents selected from the following group δ, and carbon atoms of 7
To 15 aralkyl groups, an aralkyl group having 7 to 15 carbon atoms substituted by 1 to 5 with a substituent selected from the following δ group, an arylalkenyl group having 8 to 16 carbon atoms,
Or represents a 1 to 5-substituted C 8 or 16 arylalkenyl group having a carbon with a substituent selected from the following δ group, X ⁸ represents a single bond, a carbonyl group (-C (= O)
—), An oxycarbonyl group (—OC (＝ O) —), an aminocarbonyl group (—NHC (＝ O) —) or a sulfonyl group (—SO ₂ —). ). ). Group γ: an alkyl group having 1 to 6 carbon atoms, an alkyl group having 1 to 6 carbon atoms substituted with a hydroxyl group, an alkoxy group having 1 to 6 carbon atoms, a carboxyl group, an amino group, and 1 carbon atom
Or 6-substituted mono- or dialkylamino group with alkyl group, a heterocyclic group, 1 to 5-substituted heterocyclic group with a substituent selected from the following δ group, CH ₃ O (CH ₂ CH
₂ O) _n groups (where n is an integer of 1 to 6);
Halogen atom. Group δ: alkyl group having 1 to 6 carbon atoms, 1 to 6 carbon atoms
Alkoxy groups, halogen atoms, amino groups, and 1
Or an amino group substituted with two alkyl groups having 1 to 6 carbon atoms or an alkylcarbonyl group having 1 to 6 carbon atoms, or a C1 to 6 carbon atom substituted with an alkylcarbonyl group having 1 to 6 carbon atoms. Alkyl groups. 2. R ¹ is an unsubstituted phenyl group, an unsubstituted pyridyl group, an alkyl group having 1 to 6 carbon atoms,
An alkyl-oxy group having 1 to 6 carbon atoms, an alkyl group having 1 to 6 carbon atoms substituted with 1 to 3 halogen atoms,
An alkyl-carbonyl group having 1 to 6 carbon atoms, a hydroxyl group,
A halogen atom, a nitro group, a cyano group, an aminocarbonyl group, an aminocarbonyl group substituted by 1 to 2 alkyl groups having 1 to 6 carbon atoms, an alkyl group having 1 to 6 carbon atoms,
2. A phenyl group or a pyridyl group, which is monosubstituted by a carbonylamino group, an alkyloxycarbonyl group having 1 to 6 carbon atoms or an alkyl group having 1 to 3 carbon atoms and substituted by 1 to 3 hydroxyl groups. Or a pharmacologically acceptable salt thereof. Wherein R ¹ is to C 1 -C 6 alkyl group, an alkyl of 1 to 6 carbon atoms - oxy group, 1 to 3-substituted having 1 to carbon was 6 alkyl group by a halogen atom, a carbon The phenyl group or the pyridyl group according to claim 1, wherein the phenyl group or the pyridyl group is monosubstituted with an aminocarbonyl group monosubstituted with an alkylcarbonyl group having 1 to 6 alkyl atoms, a halogen atom or an alkyl group having 1 to 6 carbon atoms. A compound or a pharmacologically acceptable salt thereof. 4. The compound according to claim 1, wherein R ¹ is a phenyl group or a pyridyl group which is monosubstituted by a methyl group, a methoxy group, a trifluoromethyl group, a methylcarbonyl group, a halogen atom or a methylaminocarbonyl group. Or a pharmacologically acceptable salt thereof. 5. An alkyl-carbonyl group having 1 to 6 carbon atoms, wherein R ² is a hydrogen atom, an alkyl-carbonyl group having 1 to 6 carbon atoms, a halogen atom or / and an amino group, which is substituted by 1 to 3 carbon atoms, An aryl-carbonyl group having 6 to 14 carbon atoms, an aryl-carbonyl group having 6 to 14 carbon atoms substituted with an alkyloxy group having 1 to 6 carbon atoms, an alkyloxycarbonyl group having 1 to 6 carbon atoms, Number 1
An aminocarbonyl group substituted by 2 to 6 alkyl groups; an alkylcarbonyl group having 1 to 6 carbon atoms substituted by an alkyloxy group having 1 to 6 carbon atoms;
1 to 20 alkyl-carbonylamino-C1-6 alkyl-carbonyl group, C1-6 alkyl-carbonyloxy-C1-6 alkyl-carbonyl group, or C1 Amino-carbon number 1 to 6 substituted by 1 or 2 alkyl groups
The compound according to any one of claims 1 to 4, which is an alkyl-carbonyl group, or a pharmacologically acceptable salt thereof. Wherein R ² is a hydrogen atom, a methyl group, an ethyl group, an isopropyl group, a trifluoromethyl group, a phenyl group, 4
-Methoxyphenylcarbonyl group, methoxycarbonyl group, t-butoxycarbonyl group, dimethylaminocarbonyl group, aminomethylcarbonyl group, 2-methylpropyloxycarbonyl group, methoxymethylcarbonyl group,
Acetylaminomethylcarbonyl group, acetoxymethylenecarbonyl group, methylaminomethylenecarbonyl group,
5. The compound according to claim 1, which is a dimethylaminomethylenecarbonyl group, or a pharmacologically acceptable salt thereof. 7. R ² is a hydrogen atom, a methyl group, an ethyl group, an isopropyl group, a methoxycarbonyl group, dimethylaminocarbonyl group, aminomethyl group, 2-methyl-propyloxy group, a methoxymethyl group, The compound according to any one of claims 1 to 4, which is an acetylaminomethylcarbonyl group, an acetoxymethylenecarbonyl group, a methylaminomethylenecarbonyl group, or a dimethylaminomethylenecarbonyl group, or a pharmaceutically acceptable salt thereof. 8. R ² is a hydrogen atom, a methyl group, aminomethyl group, 2-methyl-propyloxy group, a methoxymethyl group, acetylaminomethyl group, acetoxy methylene group, methylamino methylene group, Or a dimethylaminomethylenecarbonyl group.
Or a pharmacologically acceptable salt thereof. 9. The compound according to claim 1, wherein R ³ is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 14 carbon atoms, or a pharmacologically active compound thereof. Acceptable salt. 10. The compound according to any one of claims 1 to 8, wherein R ³ is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, or a pharmaceutically acceptable salt thereof. 11. The compound according to any one of claims 1 to 8, wherein R ³ is a hydrogen atom or a methyl group, or a pharmaceutically acceptable salt thereof. (12) R ⁴ is an alkyl group having 1 to 6 carbon atoms,
A 3- to 8-membered cycloalkyl group, an alkyl group having 1 to 6 carbon atoms substituted with 1 to 3 halogen atoms,
An alkyl group having 1 to 6 carbon atoms substituted with 1 to 6 alkoxy groups, an aminocarbonyl group, an aminocarbonyl group substituted with 1 to 6 carbon atoms, an alkyl group having 1 to 6 carbon atoms, The compound according to any one of claims 1 to 11, which is an aminocarbonyl group or a carboxyl group disubstituted by a group, or a pharmaceutically acceptable salt thereof. 13. R ⁴ is a methyl group, an ethyl group, a propyl group, a 1-methylethyl group, 1-methyl - cyclopropyl group, cyclobutyl group, a trifluoromethyl group, a methoxymethyl group, a methoxycarbonyl group, an aminocarbonyl group The compound according to any one of claims 1 to 11, which is a methylaminocarbonyl group, a dimethylaminocarbonyl group, or a carboxyl group, or a pharmaceutically acceptable salt thereof. 14. R ⁴ is an alkyl group having 1 to 4 carbon atoms,
The compound according to any one of claims 1 to 11, which is an alkyl group having 1 to 4 carbon atoms or an aminocarbonyl group, which is substituted with 1 to 3 halogen atoms, or a pharmaceutically acceptable salt thereof. 15. R ⁴ is a methyl group, a 1-methylethyl group,
The compound according to any one of claims 1 to 11, which is a trifluoromethyl group or an aminocarbonyl group, or a pharmacologically acceptable salt thereof. 16. The compound according to any one of claims 1 to 11, wherein R ⁴ is a methyl group or a trifluoromethyl group, or a pharmaceutically acceptable salt thereof. 17. R ⁵ is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkyloxy group having 1 to 6 carbon atoms, a hydroxyl group, an amino group, or a carbon number substituted with 1 to 3 halogen atoms. 17. The compound according to any one of claims 1 to 16, which has 1 to 6 alkyl-carbonylamino groups, or a pharmacologically acceptable salt thereof. 18. R ⁵ is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkyloxy group having 1 to 4 carbon atoms, a hydroxyl group, an amino group, or a carbon number substituted with 1 to 3 halogen atoms. 17. The compound according to any one of claims 1 to 16, which has 1 to 4 alkyl-carbonylamino groups, or a pharmacologically acceptable salt thereof. 19. The compound according to claim 1, wherein R ⁵ is a hydrogen atom, a methyl group, a methoxy group, a hydroxyl group, an amino group or a trifluoromethylcarbonylamino group, or a pharmaceutically acceptable compound thereof. Salt. 20. The compound according to claim 1, wherein R ⁵ is a hydrogen atom, a methyl group, a methoxy group, a hydroxyl group or an amino group, or a pharmaceutically acceptable salt thereof. 21. The compound according to any one of claims 1 to 20, wherein R ⁶ is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a halogen atom, or a pharmaceutically acceptable salt thereof. 22. The compound according to any one of claims 1 to 20, wherein R ⁶ is a hydrogen atom, a methyl group or a bromine atom, or a pharmaceutically acceptable salt thereof. 23. The compound according to any one of claims 1 to 20, wherein R ⁶ is a hydrogen atom or a methyl group, or a pharmaceutically acceptable salt thereof. 24. The method according to claim 1, wherein R ⁶ is a hydrogen atom.
Or a pharmacologically acceptable salt thereof. 25. R ⁷ is a hydrogen atom, an alkyl group of 1 to 6 carbon atoms, claim 1 halogen atom, a 1 to 3-substituted alkyl group or an amino group having 1 to 6 carbon by a halogen atom 25. The compound according to any one of to 24 or a pharmacologically acceptable salt thereof. (26) R ⁷ is a hydrogen atom, a methyl group, a chlorine atom,
25. The compound according to any one of claims 1 to 24, which is a bromine atom, a trifluoromethyl group or an amino group, or a pharmaceutically acceptable salt thereof. 27. The compound according to any one of claims 1 to 24, wherein R ⁷ is a hydrogen atom, a methyl group or a chlorine atom, or a pharmaceutically acceptable salt thereof. 28. The compound or a pharmaceutically acceptable salt thereof according to any one of claims 1 to 27, wherein R ⁸ is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. 29. The compound or a pharmaceutically acceptable salt thereof according to any one of claims 1 to 27, wherein R ⁸ is a hydrogen atom or a methyl group. 30. The method according to claim 1, wherein R ⁸ is a hydrogen atom.
Or a pharmacologically acceptable salt thereof. 31. The compound or a pharmaceutically acceptable salt thereof according to claim 1, wherein X ¹ is an oxygen atom or a sulfur atom. 32. The method according to claim 1, wherein X ¹ is a sulfur atom.
Or a pharmacologically acceptable salt thereof. 33. A medicament comprising the compound according to any one of claims 1 to 32 or a pharmacologically acceptable salt thereof. 34. A cell growth inhibitor comprising the compound according to any one of claims 1 to 32 or a pharmaceutically acceptable salt thereof. 35. A therapeutic or prophylactic agent for cancer comprising the compound according to any one of claims 1 to 32 or a pharmaceutically acceptable salt thereof.