US 12,110,299 B2Granted

Thiazole derivatives and pharmaceutically acceptable salts thereof

AssigneeYungjin Pharm. Co., Ltd.

InventorsKwang Ok Lee, Jakyung Yoo, Jun Hee Lee, Mijung Lee, Kangwoo Lee, Jieun Min

Life of this patent

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Abstract

The present invention provides a novel thiazole derivative or a pharmaceutically acceptable salt thereof, and a method for preparing the same. The thiazole derivative or pharmaceutically acceptable salt thereof according to the present invention has selective inhibitory activity against cyclin-dependent kinase (CDK) and thus can be used as a preventive or therapeutic agent for various diseases associated with CDK.

Claims17

Dependent claims

A compound represented by Formula (I), or a pharmaceutically acceptable salt thereof

wherein:
ring A is phenyl, pyridinyl, pyrazinyl, pyrazolyl, thiophenyl, thiazolyl, or piperidinyl;
ring B is phenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, pyrazolyl, imidazolyl, thiazolyl, tetrahydropyridinyl, piperidinyl, or piperazinyl;
R1 is halo, C1-C6 alkyl, C3-C7 cycloalkyl, C1-C6 haloalkyl, cyano, —SRc, —C(O)Rc, —C(O)OR, —N(Rc)(Rd), —ORc, or —C(Rg)—ORc;
Rc and Rd are each independently H or C1-C6 alkyl;
Rg is H or C1-C6 alkyl;
R2V and R2w are each independently H, halo, or C1-C6 alkyl or
R2v and R2w, taken together with the atom to which they are attached, form a C3-C7 cycloalkyl;
L1 is absent, —N(Re)—, or —*CH2N(Rc)—, * is the site in which L1 is attached to ring B;
where Re is H or C1-C6 alkyl;
or Re is bound to an atom on ring B, thereby forming ring B-fused pyrrole or pyrrolidine which is unsubstituted or substituted with C1-C6 alkyl;
wherein Rf1 is H, halo, C1-C6 alkyl, or cyano;
Rf2 and Rf3 are each independently H, C1-C6 alkyl, C3-C7 cycloalkyl, —N(Rc′ (Rd′), or —CH2N(Rc′)(Rd′);
Rc′ and Rd′ are each independently C1-C6 alkyl;
or
Rc′ and Rd′, taken together with the atom to which they are attached, form azetidinyl;
piperidinyl;
morpholinyl;
piperazinyl which is unsubstituted or substituted with C1-C6 alkyl;
2,5-diazabicyclo[2.2.1heptanyl which is unsubstituted or substituted with C1-C6 alkyl;
2-oxa-5-azabicyclo[2.2.11heptanyl:
or pyrrolidinyl which is unsubstituted or substituted with halo, hydroxy or C1-C6 alkoxy-C1-C6 alkyl;
Ra is H, halo, or C1-C6 alkyl;
Rb is H, halo, C1-C6 alkyl, C3-C7 cycloalkyl, C1-C6 alkoxy, cyano, C1-C6 haloalkyl, —N(CH3)—CH2CH—N(CH3), or piperazinyl which is unsubstituted or substituted with C1-C6 alkyl;
m and n are each integer 1.

22 more elements

A compound selected from the group consisting of

1) N-(5-(3-(1-((5-methylthiazol-2-yl)amino)-1-oxopropan-2-yl)phenyl)pyridin-2-yl)acrylamide;
2) N-(5-(3-(1-((5-cyclopropylthiazol-2-yl)amino)-1-oxopropan-2-yl)phenyl)pyridin-2-yl)acrylamide;
3) (R)-N-(5-(3-(1-((5-cyclopropylthiazol-2-yl)amino)-1-oxopropan-2-yl)phenyl)pyridin-2-yl)acrylamide;
4) N-(5-(3-(1-((5-ethylthiazol-2-yl)amino)-1-oxopropan-2-yl)phenyl)pyridin-2-yl)acrylamide;
5) (E)-4-(dimethylamino)-N-(5-(3-(1-((5-methylthiazol-2-yl)amino)-1-oxopropan-2-yl)phenyl)pyridin-2-yl)but-2-enamide;
6) (E)-N-(5-(3-(1-((5-cyclopropylthiazol-2-yl)amino)-1-oxopropan-2-yl)phenyl)pyridin-2-yl)-4-(dimethylamino)but-2-enamide;
7) (E)-4-(dimethylamino) -N-(5-(3-(1-(5-methylthiazol-2-yl)amino-1-oxopropan-2-yl)phenyl)pyridin-2-yl)but-2-enamide hydrochloride;
8) N-(3-fluoro-3′-(1-(5-methylthiazol-2-yl)amino-1-oxopropan-2-yl)-[1,1′-biphenyl]-4-yl)acrylamide
9) 2-(3-(1-acryloylindolin-5-yl)phenyl)-N-(5-methylthiazol-2-yl)propanamide;
10) (E)-N-(5-(3-(1,1-difluoro-2-((5-methylthiazol-2-yl)amino)-2-oxoethyl)phenyl)pyridin-2-yl)-4-(dimethylamino)but-2-enamide;
11) N-(6-(3-(1-((5-cyanothiazol-2-yl)amino)-1-oxopropane-2-yl)-4-fluorophenyl)pyridazin-3-yl)acrylamide;
12) 2-(3-(6-acrylamidopyridazin-3-yl)phenyl)-N-(5-cyanothiazol-2-yl)-3-methylbutanamide;
13) N-(6-(5-(1-((5-cyanothiazol-2-yl)amino)-1-oxopropan-2-yl)-2-fluorophenyl)pyridazin-3-yl)acrylamide;
14) (S)-N-((5-(3-(1-(5-cyclopropylthiazol-2-yl)amino)-1-oxopropane-2-yl)phenyl)pyridin-2-yl)acrylamide;
15) (S,E)-N-((5-(3-(1-(5-cyclopropylthiazol-2-yl)amino)-1-oxopropan-2-yl)phenyl)pyridin-2-yl)-4-(dimethylamino)but-2-enamide;
16) (S)-N-((6-(3-(1-(5-cyclopropylthiazol-2-yl)amino)-1-oxopropan-2-yl)phenyl) pyrazin-2-yl) acrylamide
17) (S,E)-4-(dimethylamino)-N-(5-(3-(1-((5-ethylthiazol-2-yl)amino)-1-oxopropan-2-yl)phenyl)pyridin-2-yl)but-2-enamide;
18) (S)-N-(5-(3-(1-((5-cyanothiazole-2-yl)amino)-1-oxopropan-2-yl)phenyl)pyridin-2-yl)acrylamide;
19) (S)-2-(3-(6-acrylamidopyridin-3-yl)phenyl)-N-(5-ethylthiazol-2-yl)butanamide;
20) (S)-2-(4′-acrylamido-3′-fluoro-[1,1′-biphenyl]-3-yl)-N-(5-ethylthiazol-2-yl)butanamide;
21) (S,E)-N-(5-(3-(1-((5-cyanothiazol-2-yl)amino)-1-oxopropan-2-yl)phenyl)pyridin-2-yl)-4-(dimethylamino)but-2-enamide;
22) (S)-N-(5-(3-(1-(5-cyclopropylthiazol-2-yl)amino)-1-oxopropan-2-yl)phenyl)pyrazin-2-yl)acrylamide;
23) (S)-N-(3′-(1-(5-cyclopropylthiazol-2-yl)amino-1-oxopropan-2-yl)-[1,1′-biphenyl]-4-yl)acrylamide;
24) (S)-N-(3′-(1-(5-cyclopropylthiazol-2-yl)amino-1-oxopropan-2-yl)-3-fluoro-[1,1′-biphenyl]-4-yl)acrylamide;
25) (S)-N-(5-(3-(1-(5-cyanothiazol-2-yl)amino-1-oxopropan-2-yl)phenyl)pyrazin-2-yl)acrylamide;
26) (S)-N-(6-(3-(1-(5-cyanothiazol-2-yl)amino-1-oxopropan-2-yl)phenyl) pyrazin-2-yl) acrylamide
27) (S)-N-(5-(3-(1-(5-cyclopropylthiazol-2-yl)amino)-1-oxopropan-2-yl)phenyl)pyrimidin-2-yl)acrylamide;
28) (S)-N-(6-(3-(1-(5-cyclopropylthiazol-2-yl)amino)-1-oxopropan-2-yl)phenyl)pyridazin-3-yl)acrylamide;
29) (S) -N-((5-(3-(1-(5-cyclopropylthiazol-2-yl)amino)-1-oxopropan-2-yl)phenyl)-3-fluoropyridin-2-yl) acrylamide
30) (S)-N-(3-cyano-3′-(1-((5-ethylthiazol-2-yl)amino)-1-oxopropan-2-yl)-[1,1′-biphenyl]-4-yl)acrylamide;
31) (S)-N-(5-(3-(1-((5-ethylthiazol-2-yl)amino)-1-oxopropan-2-yl)phenyl)-6-fluoropyridin-2-yl)acrylamide;
32) (S)-N-(6-(3-(1-((5-cyanothiazol-2-yl)amino)-1-oxopropan-2-yl)phenyl)pyridazin-3-yl)acrylamide;
33) (S)-N-(5-(3-(1-((5-cyanothiazol-2-yl)amino)-1-oxopropan-2-yl)phenyl)-3-fluoropyridin-2-yl)acrylamide;
34) (S)-N-(5-(3-(1-((5-cyanothiazol-2-yl)amino)-1-oxopropan-2-yl)phenyl)-3-methylpyrazin-2-yl)acrylamide;
35) (S)-N-(5-(3-(1-(5-isopropylthiazol-2-yl)amino)-1-oxopropan-2-yl)phenyl)pyridin-2-yl) acrylamide
36) (S)-N-(5-(3-(1-((5-isopropylthiazol-2-yl)amino)-1-oxopropan-2-yl)phenyl)pyrazin-2-yl)acrylamide;
37) (S)-N-(5-(3-(1-oxo-1-((5-(trifluoromethyl)thiazol-2-yl)amino)propan-2-yl)phenyl)pyrazin-2-yl)acrylamide;
38) (S)-N-(5-(3-(1-oxo-1-((5-(trifluoromethyl)thiazol-2-yl)amino)propan-2-yl)phenyl)pyridin-2-yl)acrylamide;
39) (S)-N-(6-(3-(1-oxo-1-((5-(trifluoromethyl)thiazol-2-yl)amino)propan-2-yl)phenyl)pyridazin-3-yl)acrylamide;
40) (S)-N-(6-(3-(1-((5-isopropylthiazol-2-yl)amino)-1-oxopropan-2-yl)phenyl)pyridazin-3-yl)acrylamide;
41) N-(5′-(1-(5-cyanothiazol-2-yl)amino-1-oxopropane-2-yl)-[3,3′-bipyridin]-6-yl) acrylamide;
42) N-(4-(1-(5-cyanothiazole-2-yl)amino-1-oxopropan-2-yl)-[2,3′-bipyridine]-6′-yl) acrylamide;
43) N-(5-(5-(1-(5-cyclopropylthiazol-2-yl)amino-1-oxopropan-2-yl)pyridin-3-yl) pyrazin-2-yl) acrylamide
44) N-(5-(5-(1-((5-cyanothiazol-2-yl)amino)-1-oxopropan-2-yl)pyridin-3-yl)pyrazin-2-yl)acrylamide;
45) N-(5-(5-(1-oxo-1-((5-(trifluoromethyl)thiazol-2-yl)amino)propan-2-yl)pyridin-3-yl)pyrazin-2-yl)acrylamide;
46) N-(5-(5-(1-((5-ethylthiazol-2-yl)amino)-1-oxopropan-2-yl)pyridin-3-yl)pyrazin-2-yl)acrylamide;
47) N-(5-(5-(1-((5-isopropylthiazol-2-yl)amino)-1-oxopropan-2-yl)pyridin-3-yl)pyrazin-2-yl)acrylamide;
48) N-(5-(5-(1-((5-acetylthiazol-2-yl)amino)-1-oxopropan-2-yl)pyridin-3-yl)pyrazin-2-yl)acrylamide;
49) N-(6-(5-(1-oxo-1-((5-(trifluoromethyl)thiazol-2-yl)amino)propan-2-yl)pyridin-3-yl)pyridazin-3-yl)acrylamide;
50) N-(4-(1-((5-cyclopropylthiazol-2-yl)amino)-1-oxopropan-2-yl)-[2,3′-bipyridine]-6′-yl)acrylamide;
51) (R)-N-(5-(5-(1-oxo-1-((5-(trifluoromethyl)thiazol-2-yl)amino)propan-2-yl)pyridin-3-yl)pyrazin-2-yl)acrylamide;
52) (S)-N-(5-(5-(1-oxo-1-((5-(trifluoromethyl)thiazol-2-yl)amino)propan-2-yl)pyridin-3-yl)pyrazin-2-yl)acrylamide;
53) N-(5-(5-(1-oxo-1-((5-(trifluoromethyl)thiazol-2-yl)amino)propan-2-yl)thiophen-3-yl)pyridin-2-yl)acrylamide;
54) N-(5-(5-(1-(5-cyclopropylthiazol-2-yl)amino-1-oxopropan-2-yl)pyridin-3-yl) pyrazin-2-yl) acrylamide
55) N-(5-(5-(2-methyl-1-oxo-1-((5-(trifluoromethyl)thiazol-2-yl)amino)propan-2-yl)pyridin-3-yl)pyrazin-2-yl)acrylamide;
56) (S)-2-(3-(5-(2-cyanoacetamido)pyrazin-2-yl)phenyl)-N-(5-(trifluoromethyl)thiazol-2-yl)propanamide;
57) N-(5-(5-(1-oxo-1-((5-(trifluoromethyl)thiazol-2-yl)amino)propan-2-yl)thiophen-3-yl)pyrazin-2-yl)acrylamide;
58) (S)-2-(3-(5-(2-cyanoacetamido)pyrazin-2-yl)phenyl)-N-(5-cyanothiazol-2-yl)propanamide;
59) N-(5-(3-methyl-1-(1-oxo-1-((5-(trifluoromethyl)thiazol-2-yl)amino)propan-2-yl)-1H-pyrazol-4-yl)pyridin-2-yl)acrylamide;
60) 2-(1‘-acryloyl-1’,2′,3′,6′-tetrahydro-[3,4′-bipyridine]-5-yl)-N-(5-cyanothiazol-2-yl)propanamide;
61) N-(5-(5-(1-((5-chlorothiazol-2-yl)amino)-1-oxopropan-2-yl)pyridin-3-yl)pyrazine-2-yl)acrylamide;
62) (S)-N-(6-(3-(1-((5-cyclopropylthiazol-2-yl)amino)-1-oxopropan-2-yl)phenyl)pyridin-3-yl)acrylamide;
63) (E)-4-(dimethylamino)-N-(5-(5-(1-oxo-1-((5-(trifluoromethyl)thiazol-2-yl)amino)propan-2-yl)pyridin-3-yl)pyrazin-2-yl)but-2-enamide;
64) 2-(5-(5-(2-cyanoacetamido)pyrazin-2-yl)pyridin-3-yl)-N-(5-(trifluoromethyl)thiazol-2-yl)propanamide;
65) (E)-2-cyano-3-cyclopropyl-N-(5-(5-(1-oxo-1-((5-(trifluoromethyl)thiazol-2-yl)amino)propan-2-yl)pyridin-3-yl)pyrazin-2-yl)acrylamide;
66) N-(5-(5-(1-((5-methoxythiazol-2-yl)amino)-1-oxopropan-2-yl)pyridin-3-yl)pyrazin-2-yl)acrylamide;
67) N-(5-(5-(1-((5-fluorothiazol-2-yl)amino)-1-oxopropan-2-yl)pyridin-3-yl)pyrazin-2-yl)acrylamide;
68) N-(2-(4-methylpiperazin-1-yl)-4-(5-(1-oxo-1-((5-(trifluoromethyl)thiazol-2-yl)amino)propan-2-yl)pyridin-3-yl)phenyl)acrylamide;
69) (E)-2-cyano-3-(dimethylamino)-N-(5-(5-(1-oxo-1-((5-(trifluoromethyl)thiazol-2-yl)amino)propan-2-yl)pyridin-3-yl)pyrazin-2-yl)acrylamide;
70) N-(1-(5-(1-oxo-1-((5-(trifluoromethyl)thiazol-2-yl)amino)propan-2-yl)pyridin-3-yl)piperidin-4-yl)acrylamide;
71) N-(5-(5-(1-((5-(methylthio)thiazol-2-yl)amino)-1-oxopropan-2-yl)pyridin-3-yl)pyrazin-2-yl)acrylamide;
72) ethyl 2-(2-(5-(5-acrylamidopyrazin-2-yl)pyridin-3-yl)propanamido)thiazole-5-carboxylate;
73) (E)-N-(5-(5-(1-((5-chlorothiazol-2-yl)amino)-1-oxopropan-2-yl)pyridin-3-yl)pyrazin-2-yl)-4-(dimethylamino)but-2-enamide;
74) (E)-4-morpholino-N-(5-(5-(1-oxo-1-((5-(trifluoromethyl)thiazol-2-yl)amino)propan-2-yl)pyridin-3-yl)pyrazin-2-yl)but-2-enamide;
75) (E)-N-(5-(5-(1-oxo-1-((5-(trifluoromethyl)thiazol-2-yl)amino)propan-2-yl)pyridin-3-yl)pyrazin-2-yl)but-2-enamide;
76) N-(5-(5-(1-((5-chlorothiazol-2-yl)amino)-1-oxopropan-2-yl)thiophen-3-yl)pyridin-2-yl)acrylamide;
77) N-(5-(5-(1-((5-ethylthiazol-2-yl)amino)-1-oxopropan-2-yl)thiophen-3-yl)pyridin-2-yl)acrylamide;
78) N-(5-(5-(1-((5-acetylthiazol-2-yl)amino)-1-oxopropan-2-yl)thiophen-3-yl)pyridin-2-yl)acrylamide;
79) 2-(5-(5-propionamidopyrazin-2-yl)pyridin-3-yl)-N-(5-(trifluoromethyl)thiazol-2-yl)propanamide;
80) (E)-4-(5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl)-N-(5-(5-(1-oxo-1-((5-(trifluoromethyl)thiazol-2-yl)amino)propan-2-yl)pyridin-3- yl)pyrazin-2-yl)but-2-enamide;
81) (S,E)-4-(dimethylamino)-N-(5-(3-(1-oxo-1-((5-(trifluoromethyl)thiazol-2-yl)amino)propan-2-yl)phenyl)pyrazin-2-yl)but-2-enamide;
82) N-(5′-(1-oxo-1-((5-(trifluoromethyl)thiazol-2-yl)amino)propan-2-yl)-[3,3′-bipyridin]-6-yl)acrylamide;
83) (E)-4-(2-oxa-5-azabicyclo[2.2.1]heptan-5-yl)-N-(5-(5-(1-oxo-1-((5-(trifluoromethyl)thiazol-2-yl)amino)propan-2-yl)pyridin-3- yl)pyrazin-2-yl)but-2-enamide;
84) N-(4-fluoro-5′-(1-oxo-1-((5-(trifluoromethyl)thiazol-2-yl)amino)propan-2-yl)[3,3′-bipyridin]-6-yl)acrylamide;
85) 2-(5-(4-acryloylpiperazin-1-yl)pyridin-3-yl)-N-(5-(trifluoromethyl)thiazol-2-yl)propanamide;
86) 2-(5-(4-acryloylpiperazin-1-yl)pyridin-3-yl)-N-(5-ethylthiazol-2-yl)propanamide;
87) N-(6-(5-(1-((5-ethylthiazol-2-yl)amino)-1-oxopropan-2-yl)thiophen-3-yl)pyridin-3-yl)acrylamide;
88) N-(5-cyano-5′-(1-oxo-1-((5-(trifluoromethyl)thiazol-2-yl)amino)propan-2-yl)[3,3′-bipyridin]-6-yl)acrylamide;
89)N-((5′-(1-oxo-1-((5-(trifluoromethyl)thiazol-2-yl)amino)propan-2-yl)-[3,3′-bipyridin]-6-yl)methyl)acrylamide;
90) N-(5′-(1-oxo-1-((5-(trifluoromethyl)thiazol-2-yl)amino)propan-2-yl)-[2,3′-bipyridin]-5-yl)acrylamide;
91) (S,E)-4-(dimethylamino)-N-(5-(3-(1-oxo-1-((5-(trifluoromethyl)thiazol-2-yl)amino)propan-2-yl)phenyl)pyrazin-2-yl)but-2-enamide;
92) (S,E)-4-morpholino-N-(5-(3-(1-oxo-1-((5-(trifluoromethyl)thiazol-2-yl)amino)propan-2-yl)phenyl)pyrazin-2-yl)but-2-enamide;
93) (S,E)-N-(5-(3-(1-((5-chlorothiazol-2-yl)amino)-1-oxopropan-2-yl)phenyl)pyrazin-2-yl)-4-(dimethylamino)but-2-enamide;
94) (E)-4-(2-oxa-5-azabicyclo[2.2.1]heptan-5-yl)-N-(5-(3-((S)-1-((5-chlorothiazol-2-yl)amino)-1-oxopropan-2-yl)phenyl)pyrazin-2-yl)but-2-enamide;
95) (S,E)-4-(4-methylpiperazin-1-yl)-N-(5-(3-(1-oxo-1-((5-(trifluoromethyl)thiazol-2-yl)amino)propan-2-yl)phenyl)pyrazin-2-yl)but-2-enamide;
96) (E)-4-(2-oxa-5-azabicyclo[2.2.1]heptan-5-yl)-N-(5-(3-((S)-1-oxo-1-((5-(trifluoromethyl)thiazol-2-yl)amino)propan-2-yl)phenyl)pyrazin-2-yl)but-2-enamide;
97) (S,E)-N-(5-(3-(1-((5-chlorothiazol-2-yl)amino)-1-oxopropan-2-yl)phenyl)pyrazin-2-yl)-4-(4-methylpiperazin-1-yl)but-2-enamide;
98) (S,E)-N-(5-(3-(1-((5-chlorothiazol-2-yl)amino)-1-oxopropan-2-yl)phenyl)pyrazin-2-yl)-4-morpholinobut-2-enamide;
99) (S,E)-4-(dimethylamino)-N-(3-fluoro-5-(3-(1-oxo-1-((5-(trifluoromethyl)thiazol-2-yl)amino)propan-2-yl)phenyl)pyridin-2-yl)but-2-enamide;
100) (S,E)-4-(dimethylamino)-N-(3-methoxy-5-(3-(1-oxo-1-((5-(trifluoromethyl)thiazol-2-yl)amino)propan-2-yl)phenyl)pyridin-2-yl)but-2-enamide;
101) (S,E)-N-(3-cyano-5-(3-(1-oxo-1-((5-(trifluoromethyl)thiazol-2-yl)amino)propan-2-yl)phenyl)pyridin-2-yl)-4-(dimethylamino)but-2-enamide;
102) (S,E)-N-(5-(3-(1-oxo-1-((5-(trifluoromethyl)thiazol-2-yl)amino)propan-2-yl)phenyl)pyrazin-2-yl)-4-(pyrrolidin-1-yl)but-2-enamide;
103) (S,E)-4-(azetidin-1-yl)-N-(5-(3-(1-oxo-1-((5-(trifluoromethyl)thiazol-2-yl)amino)propan-2-yl)phenyl)pyrazin-2-yl)but-2-enamide;
104) (S,E)-N-(5-(3-(1-((5-cyclobutylthiazol-2-yl)amino)-1-oxopropan-2-yl)phenyl)pyrazin-2-yl)-4-(dimethylamino)but-2-enamide;
105) (S,E)-4-(dimethylamino)-N-(5-(3-(1-((5-(2-hydroxypropan-2-yl)thiazol-2-yl)amino)-1-oxopropan-2-yl)phenyl)pyrazin-2-yl)but-2-enamide;
106) (S,E)-4-(dimethylamino)-N-(5-(3-(1-((5-(dimethylamino)thiazol-2-yl)amino)-1-oxopropan-2-yl)phenyl)pyrazin-2-yl)but-2-enamide;
107) (E)-4-(dimethylamino)-N-(5′-(1-oxo-1-((5-(trifluoromethyl)thiazol-2-yl)amino)propan-2-yl)-[3,3′-bipyridin]-6-yl)but-2-enamide;
108) (E)-N-(5-cyano-5′-(1-oxo-1-((5-(trifluoromethyl)thiazol-2-yl)amino)propan-2-yl)-[3,3′-bipyridin]-6-yl)-4-(dimethylamino)but-2-enamide;
109) (S,E)-4-(dimethylamino)-N-(3-methoxy-5-(3-(1-oxo-1-((5-(trifluoromethyl)thiazol-2-yl)amino)propan-2-yl)phenyl)pyrazin-2-yl)but-2-enamide;
110) (S,E)-2-(3-(1-(4-(dimethylamino)but-2-enoyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)-N-(5-(trifluoromethyl)thiazol-2-yl)propanamide;
111) (S,E)-4-(dimethylamino)-N-(5-(3-(1-oxo-1-((5-(trifluoromethyl)thiazol-2-yl)amino)propan-2-yl)phenyl)-3-(trifluoromethyl)pyridin-2-yl)but-2-enamide;
112) (S,E)-4-(dimethylamino)-N-(3-methyl-5-(3-(1-oxo-1-((5-(trifluoromethyl)thiazol-2-yl)amino)propan-2-yl)phenyl)pyridin-2-yl)but-2-enamide;
113) (S,E)-N-(3-chloro-5-(3-(1-oxo-1-((5-(trifluoromethyl)thiazol-2-yl)amino)propan-2-yl)phenyl)pyridin-2-yl)-4-(dimethylamino)but-2-enamide;
114) (S,E)-4-(diethylamino)-N-(5-(3-(1-oxo-1-((5-(trifluoromethyl)thiazol-2-yl)amino)propan-2-yl)phenyl)pyrazin-2-yl)but-2-enamide;
115) (E)-4-((R)-3-fluoropyrrolidin-1-yl)-N-(5-(3-((S)-1-oxo-1-((5-(trifluoromethyl)thiazol-2-yl)amino)propan-2-yl)phenyl)pyrazin-2-yl)but-2- enamide;
116) (S,E)-4-(dimethylamino)-N-(5-(3-(1-oxo-1-((5-(trifluoromethyl)thiazol-2-yl)amino)propan-2-yl)phenyl)pyridin-2-yl)but-2-enamide;
117) (E)-4-((S)-3-fluoropyrrolidin-1-yl)-N-(5-(3-((S)-1-oxo-1-((5-(trifluoromethyl)thiazol-2-yl)amino)propan-2-yl)phenyl)pyrazin-2-yl)but-2- enamide;
118) (E)-4-((S)-2-(methoxymethyl)pyrrolidin-1-yl)-N-(5-(3-((S)-1-oxo-1-((5-(trifluoromethyl)thiazol-2-yl)amino)propan-2-yl)phenyl)pyrazin-2-yl)but-2-enamide;
119) (E)-4-(3-hydroxypyrrolidin-1-yl)-N-(5-(3-((S)-1-oxo-1-((5-(trifluoromethyl)thiazol-2-yl)amino)propan-2-yl)phenyl)pyrazin-2-yl)but-2-enamide;
120) (S,E)-N-(5-(3-(1-oxo-1-((5-(trifluoromethyl)thiazol-2-yl)amino)propan-2-yl)phenyl)pyrazin-2-yl)-4-(piperidin-1-yl)but-2-enamide;
121) (S,E)-N-(3-cyano-5-(3-(1-((5-ethylthiazol-2-yl)amino)-1-oxopropan-2-yl)phenyl)pyridin-2-yl)-4-(dimethylamino)but-2-enamide;
122) (S,E)-2-(3-(1-(4-(dimethylamino)but-2-enoyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)-N-(5-ethylthiazol-2-yl)propanamide;
123) (E)-4-(2-oxa-5-azabicyclo[2.2.1]heptan-5-yl)-N-(3-cyano-5-(3-((S)-1-((5-ethylthiazol-2-yl)amino)-1-oxopropan-2-yl)phenyl)pyridin-2-yl)but-2-enamide;
124) (S)-N-(3-cyano-5-(3-(1-oxo-1-((5-(trifluoromethyl)thiazol-2-yl)amino)propan-2-yl)phenyl)pyridin-2-yl)acrylamide;
125) (S,E)-4-(dimethylamino)-N-(5-(3-(1-((5-ethylthiazol-2-yl)amino)-1-oxopropan-2-yl)phenyl)-3-methyl)pyridin-2-yl)but-2-enamide;
126) (S,E)-2-(3-(1-(4-(dimethylamino)but-2-enoyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)-N-(5-ethylthiazol-2-yl)propanamide;
127) (S,E)-2-(3-(1-(4-(dimethylamino)but-2-enoyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)-N-(5-ethylthiazol-2-yl)propanamide;
128) (E)-1-(3-(5-cyano-6-(4-(dimethylamino)but-2-enamido)pyridin-3-yl)phenyl)-N-(5-ethylthiazol-2-yl)cyclopropane-1-carboxamide;
129) (S,E)-4-(dimethylamino)-N-(5-(3-(1-((5-ethylthiazol-2-yl)amino)-1-oxopropan-2-yl)phenyl)pyridin-2-yl)-N-methylbut-2-enamide;
130) (S,E)-4-(dimethylamino)-N-(5-(3-(1-((5-ethylthiazol-2-yl)amino)-1-oxopropan-2-yl)phenyl)-3-fluoropyridin-2-yl)but-2-enamide;
131) (E)-4-(dimethylamino)-N-(6-(3-(1-((5-ethylthiazol-2-yl)amino)-1-oxobutan-2-yl)phenyl)pyridin-3-yl)but-2-enamide;
132) (S,E)-N-(3-cyano-5-(3-(1-((5-ethylthiazol-2-yl)amino)-1-oxopropan-2-yl)phenyl)pyridin-2-yl)-4-(dimethylamino)-N-methylbut-2-enamide;
133) (E)-1-(3-(1-(4-(dimethylamino)but-2-enoyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)-N-(5-ethylthiazol-2-yl)cyclopropane-1- carboxamide;
134) (E)-1-(3-(6-(4-(dimethylamino)but-2-enamido)-5-fluoropyridin-3-yl)phenyl)-N-(5-ethylthiazol-2-yl)cyclopropane-1-carboxamide;
135) (S,E)-N-(3-cyano-5-(3-(1-((5-ethylthiazol-2-yl)amino)-1-oxopropan-2-yl)phenyl)pyridin-2-yl)-4-morpholinobut-2-enamide;
136) (S,E)-N-(3-cyano-5-(3-(1-((5-ethylthiazol-2-yl)amino)-1-oxopropan-2-yl)phenyl)pyridin-2-yl)-4-(4-methylpiperazin-1-yl)but-2-enamide;
137) (E)-N-(5-cyano-5′-(1-((5-ethylthiazol-2-yl)amino)-1-oxopropan-2-yl)-[3,3′-bipyridin]-6-yl)-4-(dimethylamino)but-2-enamide;
138) (E)-N-(3-cyano-5-(3-(1-((5-ethylthiazol-2-yl)amino)-1-oxobutan-2-yl)phenyl)pyridin-2-yl)-4-(dimethylamino)but-2-enamide;
139) (S)-2-(3-(5-cyano-6-(2-cyanoacetamido)pyridin-3-yl)phenyl)-N-(5-ethylthiazol-2-yl)propanamide;
140) N-(5-(6-(1-((5-methylthiazol-2-yl)amino)-1-oxopropan-2-yl)pyrazin-2-yl)pyridin-2-yl)acrylamide;
141) N-(2′-(1-((5-methylthiazol-2-yl)amino)-1-oxopropan-2-yl)-[3,4′-bipyridin]-6-yl)acrylamide;
142) N-(4-(3-(1-((5-methylthiazol-2-yl)amino)-1-oxopropan-2-yl)piperidin-1-yl)phenyl)acrylamide;
143) N-(5-(2-(1-((5-methylthiazol-2-yl)amino)-1-oxopropan-2-yl)thiazol-4-yl)pyridin-2-yl)acrylamide;
144) (S)-N-(3-cyclopropyl-5-(3-(1-((5-ethylthiazol-2-yl)amino)-1-oxopropan-2-yl)phenyl)pyridin-2-yl)acrylamide;
145) (S)-N-(3-((2-(dimethylamino)ethyl)(methyl)amino)-3′-(1-((5-ethylthiazol-2-yl)amino)-1-oxopropan-2-yl)-[1,1′-biphenyl]-4-yl)acrylamide;
146) (S)-N-(5-ethylthiazol-2-yl)-2-(3-(6-(vinylsulfonamido)pyridin-3-yl)phenyl)propanamide;
147) (S)-N-(3-(3-(1-((5-ethylthiazol-2-yl)amino)-1-oxopropan-2-yl)phenyl)-1-methyl-1H-pyrazol-5-yl)acrylamide;
148) (S)-N-(4-(3-(1-((5-ethylthiazol-2-yl)amino)-1-oxopropan-2-yl)phenyl)-1H-imidazol-2-yl)acrylamide;
and
149) (S)-N-(4-(3-(1-((5-ethylthiazol-2-yl)amino)-1-oxopropan-2-yl)phenyl)thiazol-2-yl)acrylamide.

147 more elements

Dependencies are inferred from the claim text.

Facts

Application: 17/277,033Filed 11 Sep 2019
Priority: KR 10-2018-011100117 Sep 2018
Published: US 2021/0284658 A116 Sep 2021
Granted: 8 Oct 2024
Term ends: Not estimatedThe source records don’t support an estimate.

Classification13 codes

A61P 35/00
Antineoplastic agents
C07D 498/18
In which the condensed system contains three hetero rings: bridged systems
A61P 1/16
Drugs for disorders of the alimentary tract or the digestive system: for liver or gallbladder disorders, e.g. hepatoprotective agents,…
A61P 35/02
Antineoplastic agents: specific for leukemia

Family

US 2021/0284658 A1Pre-grant publication · published 16 Sep 2021
US 12,110,299 B2This patent

From the US filing history. Foreign family members aren’t listed.

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Abstract

Facts

Application

17/277,033Filed 11 Sep 2019

Priority

KR 10-2018-011100117 Sep 2018

Published

US 2021/0284658 A116 Sep 2021

Granted

8 Oct 2024

Term ends

Not estimatedThe source records don’t support an estimate.

Classification13 codes

A61P 35/00
Antineoplastic agents
C07D 498/18
In which the condensed system contains three hetero rings: bridged systems
A61P 1/16
Drugs for disorders of the alimentary tract or the digestive system: for liver or gallbladder disorders, e.g. hepatoprotective agents,…
A61P 35/02
Antineoplastic agents: specific for leukemia