JP2009524677A5 - - Google Patents
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- JP2009524677A5 JP2009524677A5 JP2008552423A JP2008552423A JP2009524677A5 JP 2009524677 A5 JP2009524677 A5 JP 2009524677A5 JP 2008552423 A JP2008552423 A JP 2008552423A JP 2008552423 A JP2008552423 A JP 2008552423A JP 2009524677 A5 JP2009524677 A5 JP 2009524677A5
- Authority
- JP
- Japan
- Prior art keywords
- optionally substituted
- phenyl
- thiazol
- trifluoromethyl
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- -1 -OR 4 Chemical group 0.000 claims 63
- 150000001875 compounds Chemical class 0.000 claims 51
- 125000001072 heteroaryl group Chemical group 0.000 claims 39
- 125000000623 heterocyclic group Chemical group 0.000 claims 34
- 125000003107 substituted aryl group Chemical group 0.000 claims 33
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 29
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 28
- 125000005017 substituted alkenyl group Chemical group 0.000 claims 28
- 125000003710 aryl alkyl group Chemical group 0.000 claims 27
- 125000004475 heteroaralkyl group Chemical group 0.000 claims 27
- 125000000547 substituted alkyl group Chemical group 0.000 claims 27
- 125000004426 substituted alkynyl group Chemical group 0.000 claims 27
- 125000005843 halogen group Chemical group 0.000 claims 26
- 125000000217 alkyl group Chemical group 0.000 claims 23
- 125000004093 cyano group Chemical group *C#N 0.000 claims 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 16
- 125000001309 chloro group Chemical group Cl* 0.000 claims 13
- 125000001424 substituent group Chemical group 0.000 claims 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 12
- 125000001188 haloalkyl group Chemical group 0.000 claims 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 12
- 125000004438 haloalkoxy group Chemical group 0.000 claims 9
- 125000001246 bromo group Chemical group Br* 0.000 claims 8
- 125000001153 fluoro group Chemical group F* 0.000 claims 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 8
- 125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 claims 7
- 229910052757 nitrogen Inorganic materials 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 125000004076 pyridyl group Chemical group 0.000 claims 5
- AVRQBXVUUXHRMY-UHFFFAOYSA-N 2,6-difluorobenzamide Chemical compound NC(=O)C1=C(F)C=CC=C1F AVRQBXVUUXHRMY-UHFFFAOYSA-N 0.000 claims 4
- 125000003282 alkyl amino group Chemical group 0.000 claims 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims 4
- 125000002971 oxazolyl group Chemical group 0.000 claims 4
- 125000000335 thiazolyl group Chemical group 0.000 claims 4
- 125000002757 morpholinyl group Chemical group 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 230000002265 prevention Effects 0.000 claims 3
- 239000000651 prodrug Substances 0.000 claims 3
- 229940002612 prodrug Drugs 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 239000012453 solvate Substances 0.000 claims 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims 3
- DTNSDCJFTHMDAK-UHFFFAOYSA-N 2-cyanobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C#N DTNSDCJFTHMDAK-UHFFFAOYSA-N 0.000 claims 2
- QMDMUIQZTHZWGH-UHFFFAOYSA-N 3-methylpyridine-4-carboxamide Chemical compound CC1=CN=CC=C1C(N)=O QMDMUIQZTHZWGH-UHFFFAOYSA-N 0.000 claims 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 230000005931 immune cell recruitment Effects 0.000 claims 2
- 230000003834 intracellular effect Effects 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- PUQWWUNZUBYOMY-UHFFFAOYSA-N n-[4-(2,5-dimethoxyphenyl)-1,3-thiazol-2-yl]-2,6-difluorobenzamide Chemical compound COC1=CC=C(OC)C(C=2N=C(NC(=O)C=3C(=CC=CC=3F)F)SC=2)=C1 PUQWWUNZUBYOMY-UHFFFAOYSA-N 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims 2
- ARECGWDLHRTHRH-UHFFFAOYSA-N 2,6-difluoro-n-(4-methyl-5-pyridin-3-yl-1,3-thiazol-2-yl)benzamide Chemical compound S1C(C=2C=NC=CC=2)=C(C)N=C1NC(=O)C1=C(F)C=CC=C1F ARECGWDLHRTHRH-UHFFFAOYSA-N 0.000 claims 1
- JOYAMVVOHQJMBI-UHFFFAOYSA-N 2,6-difluoro-n-(4-methyl-5-pyridin-4-yl-1,3-thiazol-2-yl)benzamide Chemical compound S1C(C=2C=CN=CC=2)=C(C)N=C1NC(=O)C1=C(F)C=CC=C1F JOYAMVVOHQJMBI-UHFFFAOYSA-N 0.000 claims 1
- AXYZEFQWLFAGRI-UHFFFAOYSA-N 2,6-difluoro-n-(4-methyl-5-pyridin-4-yl-1,3-thiazol-2-yl)benzamide;hydrobromide Chemical compound Br.S1C(C=2C=CN=CC=2)=C(C)N=C1NC(=O)C1=C(F)C=CC=C1F AXYZEFQWLFAGRI-UHFFFAOYSA-N 0.000 claims 1
- YRHNHMMVGLICDU-UHFFFAOYSA-N 2,6-difluoro-n-(4-methyl-5-thiophen-2-yl-1,3-thiazol-2-yl)benzamide Chemical compound S1C(C=2SC=CC=2)=C(C)N=C1NC(=O)C1=C(F)C=CC=C1F YRHNHMMVGLICDU-UHFFFAOYSA-N 0.000 claims 1
- XRCGNECSKSISBL-UHFFFAOYSA-N 2,6-difluoro-n-(4-methyl-5-thiophen-3-yl-1,3-thiazol-2-yl)benzamide Chemical compound S1C(C2=CSC=C2)=C(C)N=C1NC(=O)C1=C(F)C=CC=C1F XRCGNECSKSISBL-UHFFFAOYSA-N 0.000 claims 1
- JHIRFISORPMPSQ-UHFFFAOYSA-N 2,6-difluoro-n-[4-(1,2-oxazol-3-yl)-5-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]benzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC1=NC(C2=NOC=C2)=C(C=2C=C(C=CC=2)C(F)(F)F)S1 JHIRFISORPMPSQ-UHFFFAOYSA-N 0.000 claims 1
- LMUZEDUQLAAFLT-UHFFFAOYSA-N 2,6-difluoro-n-[4-(1,3,4-oxadiazol-2-yl)-5-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]benzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC1=NC(C=2OC=NN=2)=C(C=2C=C(C=CC=2)C(F)(F)F)S1 LMUZEDUQLAAFLT-UHFFFAOYSA-N 0.000 claims 1
- NYZMPLCWTQKRJK-UHFFFAOYSA-N 2,6-difluoro-n-[4-(1,3-oxazol-5-yl)-5-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]benzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC1=NC(C=2OC=NC=2)=C(C=2C=C(C=CC=2)C(F)(F)F)S1 NYZMPLCWTQKRJK-UHFFFAOYSA-N 0.000 claims 1
- OSYUTNVAYBPRQG-UHFFFAOYSA-N 2,6-difluoro-n-[4-(1-hydroxyethyl)-5-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]benzamide Chemical compound S1C(C=2C=C(C=CC=2)C(F)(F)F)=C(C(O)C)N=C1NC(=O)C1=C(F)C=CC=C1F OSYUTNVAYBPRQG-UHFFFAOYSA-N 0.000 claims 1
- MWSMKQPENXMRNB-UHFFFAOYSA-N 2,6-difluoro-n-[4-(1h-imidazol-2-yl)-5-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]benzamide;hydrochloride Chemical compound Cl.FC1=CC=CC(F)=C1C(=O)NC1=NC(C=2NC=CN=2)=C(C=2C=C(C=CC=2)C(F)(F)F)S1 MWSMKQPENXMRNB-UHFFFAOYSA-N 0.000 claims 1
- RINXDLOPSAGXNS-UHFFFAOYSA-N 2,6-difluoro-n-[4-(1h-pyrazol-5-yl)-5-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]benzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC1=NC(C2=NNC=C2)=C(C=2C=C(C=CC=2)C(F)(F)F)S1 RINXDLOPSAGXNS-UHFFFAOYSA-N 0.000 claims 1
- XVZZUSSPILKGTJ-UHFFFAOYSA-N 2,6-difluoro-n-[4-(2-hydroxypropan-2-yl)-5-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]benzamide Chemical compound S1C(C=2C=C(C=CC=2)C(F)(F)F)=C(C(C)(O)C)N=C1NC(=O)C1=C(F)C=CC=C1F XVZZUSSPILKGTJ-UHFFFAOYSA-N 0.000 claims 1
- OREDVPGFICXHDS-UHFFFAOYSA-N 2,6-difluoro-n-[4-(2-methyl-1,3-thiazol-4-yl)-5-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]benzamide Chemical compound S1C(C)=NC(C2=C(SC(NC(=O)C=3C(=CC=CC=3F)F)=N2)C=2C=C(C=CC=2)C(F)(F)F)=C1 OREDVPGFICXHDS-UHFFFAOYSA-N 0.000 claims 1
- OOHKSGRPWCFEIV-UHFFFAOYSA-N 2,6-difluoro-n-[4-(3-methylimidazol-4-yl)-5-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]benzamide Chemical compound CN1C=NC=C1C1=C(C=2C=C(C=CC=2)C(F)(F)F)SC(NC(=O)C=2C(=CC=CC=2F)F)=N1 OOHKSGRPWCFEIV-UHFFFAOYSA-N 0.000 claims 1
- LZHYDQVOZYXEBH-UHFFFAOYSA-N 2,6-difluoro-n-[4-(6-methylpyridin-2-yl)-5-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]benzamide Chemical compound CC1=CC=CC(C2=C(SC(NC(=O)C=3C(=CC=CC=3F)F)=N2)C=2C=C(C=CC=2)C(F)(F)F)=N1 LZHYDQVOZYXEBH-UHFFFAOYSA-N 0.000 claims 1
- WDPQDLYETMXUBA-UHFFFAOYSA-N 2,6-difluoro-n-[4-(hydroxymethyl)-5-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]benzamide Chemical compound S1C(C=2C=C(C=CC=2)C(F)(F)F)=C(CO)N=C1NC(=O)C1=C(F)C=CC=C1F WDPQDLYETMXUBA-UHFFFAOYSA-N 0.000 claims 1
- KHNUXYCJONMJPC-UHFFFAOYSA-N 2,6-difluoro-n-[4-formyl-5-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]benzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC1=NC(C=O)=C(C=2C=C(C=CC=2)C(F)(F)F)S1 KHNUXYCJONMJPC-UHFFFAOYSA-N 0.000 claims 1
- RYWJFQAHCQBFOE-UHFFFAOYSA-N 2,6-difluoro-n-[4-methyl-5-(2-methyl-1,3-thiazol-4-yl)-1,3-thiazol-2-yl]benzamide Chemical compound S1C(C)=NC(C2=C(N=C(NC(=O)C=3C(=CC=CC=3F)F)S2)C)=C1 RYWJFQAHCQBFOE-UHFFFAOYSA-N 0.000 claims 1
- QNAAZCJHKQTXGO-UHFFFAOYSA-N 2,6-difluoro-n-[4-methyl-5-(2-morpholin-4-ylpyridin-4-yl)-1,3-thiazol-2-yl]benzamide Chemical compound S1C(C=2C=C(N=CC=2)N2CCOCC2)=C(C)N=C1NC(=O)C1=C(F)C=CC=C1F QNAAZCJHKQTXGO-UHFFFAOYSA-N 0.000 claims 1
- CJHJMVFQKWSVPD-UHFFFAOYSA-N 2,6-difluoro-n-[4-methyl-5-(4-nitrophenyl)-1,3-thiazol-2-yl]benzamide Chemical compound S1C(C=2C=CC(=CC=2)[N+]([O-])=O)=C(C)N=C1NC(=O)C1=C(F)C=CC=C1F CJHJMVFQKWSVPD-UHFFFAOYSA-N 0.000 claims 1
- VKWISXSRLNKHAP-UHFFFAOYSA-N 2,6-difluoro-n-[4-methyl-5-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]-1,3-thiazol-2-yl]benzamide Chemical compound S1C(C=2C(=CC=C(C=2)C=2OC=CN=2)C)=C(C)N=C1NC(=O)C1=C(F)C=CC=C1F VKWISXSRLNKHAP-UHFFFAOYSA-N 0.000 claims 1
- KUFHKPXEKORDRF-UHFFFAOYSA-N 2,6-difluoro-n-[4-methyl-5-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]benzamide Chemical compound S1C(C=2C=C(C=CC=2)C(F)(F)F)=C(C)N=C1NC(=O)C1=C(F)C=CC=C1F KUFHKPXEKORDRF-UHFFFAOYSA-N 0.000 claims 1
- POVLMKLRFYNORH-UHFFFAOYSA-N 2,6-difluoro-n-[4-prop-1-en-2-yl-5-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]benzamide Chemical compound S1C(C=2C=C(C=CC=2)C(F)(F)F)=C(C(=C)C)N=C1NC(=O)C1=C(F)C=CC=C1F POVLMKLRFYNORH-UHFFFAOYSA-N 0.000 claims 1
- SBNYOJBOUCAOSB-UHFFFAOYSA-N 2,6-difluoro-n-[4-propan-2-yl-5-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]benzamide Chemical compound S1C(C=2C=C(C=CC=2)C(F)(F)F)=C(C(C)C)N=C1NC(=O)C1=C(F)C=CC=C1F SBNYOJBOUCAOSB-UHFFFAOYSA-N 0.000 claims 1
- KOUDCCLVTRPYIQ-UHFFFAOYSA-N 2,6-difluoro-n-[4-propanoyl-5-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]benzamide Chemical compound S1C(C=2C=C(C=CC=2)C(F)(F)F)=C(C(=O)CC)N=C1NC(=O)C1=C(F)C=CC=C1F KOUDCCLVTRPYIQ-UHFFFAOYSA-N 0.000 claims 1
- WKDNRYIACMZTMZ-UHFFFAOYSA-N 2,6-difluoro-n-[4-pyridin-2-yl-5-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]benzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC1=NC(C=2N=CC=CC=2)=C(C=2C=C(C=CC=2)C(F)(F)F)S1 WKDNRYIACMZTMZ-UHFFFAOYSA-N 0.000 claims 1
- JBYIMZRICHWBEA-UHFFFAOYSA-N 2,6-difluoro-n-[5-(3-fluorophenyl)-4-(hydroxymethyl)-1,3-thiazol-2-yl]benzamide Chemical compound S1C(C=2C=C(F)C=CC=2)=C(CO)N=C1NC(=O)C1=C(F)C=CC=C1F JBYIMZRICHWBEA-UHFFFAOYSA-N 0.000 claims 1
- RROCJKPOZXZHNE-UHFFFAOYSA-N 2,6-difluoro-n-[5-[2-prop-2-enoxy-5-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]benzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC1=NC=C(C=2C(=CC=C(C=2)C(F)(F)F)OCC=C)S1 RROCJKPOZXZHNE-UHFFFAOYSA-N 0.000 claims 1
- IMZJBQQCIJHXAQ-UHFFFAOYSA-N 2,6-difluoro-n-[5-[3-(2-methyltetrazol-5-yl)phenyl]-1,3-thiazol-2-yl]benzamide Chemical compound CN1N=NC(C=2C=C(C=CC=2)C=2SC(NC(=O)C=3C(=CC=CC=3F)F)=NC=2)=N1 IMZJBQQCIJHXAQ-UHFFFAOYSA-N 0.000 claims 1
- WOSKFRFJQRMKJA-UHFFFAOYSA-N 2,6-difluoro-n-[5-[3-(trifluoromethyl)phenyl]-4-(5-trimethylsilyl-1,2-oxazol-3-yl)-1,3-thiazol-2-yl]benzamide Chemical compound O1C([Si](C)(C)C)=CC(C2=C(SC(NC(=O)C=3C(=CC=CC=3F)F)=N2)C=2C=C(C=CC=2)C(F)(F)F)=N1 WOSKFRFJQRMKJA-UHFFFAOYSA-N 0.000 claims 1
- ODUZJBKKYBQIBX-UHFFFAOYSA-N 2,6-difluoroaniline Chemical compound NC1=C(F)C=CC=C1F ODUZJBKKYBQIBX-UHFFFAOYSA-N 0.000 claims 1
- IZJWUQPWWWQLQX-UHFFFAOYSA-N 2-[(2,6-difluorobenzoyl)amino]-5-[3-(trifluoromethyl)phenyl]-1,3-thiazole-4-carboxylic acid Chemical compound S1C(C=2C=C(C=CC=2)C(F)(F)F)=C(C(=O)O)N=C1NC(=O)C1=C(F)C=CC=C1F IZJWUQPWWWQLQX-UHFFFAOYSA-N 0.000 claims 1
- XFLYGKSPECTGIP-UHFFFAOYSA-N 2-[2-chloro-5-(trifluoromethyl)phenyl]-n-(2,6-difluorophenyl)-4-methyl-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C=2C(=CC=C(C=2)C(F)(F)F)Cl)SC=1C(=O)NC1=C(F)C=CC=C1F XFLYGKSPECTGIP-UHFFFAOYSA-N 0.000 claims 1
- VADKRMSMGWJZCF-UHFFFAOYSA-N 2-bromophenol Chemical compound OC1=CC=CC=C1Br VADKRMSMGWJZCF-UHFFFAOYSA-N 0.000 claims 1
- WLAOZKAHMXLQFY-UHFFFAOYSA-N 3-fluoro-n-[4-methyl-5-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]pyridine-4-carboxamide Chemical compound S1C(C=2C=C(C=CC=2)C(F)(F)F)=C(C)N=C1NC(=O)C1=CC=NC=C1F WLAOZKAHMXLQFY-UHFFFAOYSA-N 0.000 claims 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
- UNOBSGYLZJUXDJ-UHFFFAOYSA-N 3-methyl-n-(4-methyl-5-pyridin-4-yl-1,3-thiazol-2-yl)pyridine-4-carboxamide Chemical compound S1C(C=2C=CN=CC=2)=C(C)N=C1NC(=O)C1=CC=NC=C1C UNOBSGYLZJUXDJ-UHFFFAOYSA-N 0.000 claims 1
- IYYAXYFQKKSHSX-UHFFFAOYSA-N 3-methyl-n-[4-methyl-5-(4-nitrophenyl)-1,3-thiazol-2-yl]pyridine-4-carboxamide Chemical compound S1C(C=2C=CC(=CC=2)[N+]([O-])=O)=C(C)N=C1NC(=O)C1=CC=NC=C1C IYYAXYFQKKSHSX-UHFFFAOYSA-N 0.000 claims 1
- FHAOWTQICJXLCH-UHFFFAOYSA-N 3-methyl-n-[4-methyl-5-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]pyridine-4-carboxamide Chemical compound S1C(C=2C=C(C=CC=2)C(F)(F)F)=C(C)N=C1NC(=O)C1=CC=NC=C1C FHAOWTQICJXLCH-UHFFFAOYSA-N 0.000 claims 1
- HKGANQPELRXKPH-UHFFFAOYSA-N 4-methyl-n-[4-methyl-5-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]thiadiazole-5-carboxamide Chemical compound N1=NSC(C(=O)NC=2SC(=C(C)N=2)C=2C=C(C=CC=2)C(F)(F)F)=C1C HKGANQPELRXKPH-UHFFFAOYSA-N 0.000 claims 1
- PTVNFIPMUFCMIY-UHFFFAOYSA-N 5-[2-chloro-5-(trifluoromethyl)phenyl]-n-(2,6-difluorophenyl)-4-methyl-1,3-thiazole-2-carboxamide Chemical compound CC=1N=C(C(=O)NC=2C(=CC=CC=2F)F)SC=1C1=CC(C(F)(F)F)=CC=C1Cl PTVNFIPMUFCMIY-UHFFFAOYSA-N 0.000 claims 1
- SCJPAZKOYPVFRT-UHFFFAOYSA-N 5-[2-chloro-5-(trifluoromethyl)phenyl]-n-(3-methylpyridin-4-yl)-1,3-thiazole-2-carboxamide Chemical compound CC1=CN=CC=C1NC(=O)C1=NC=C(C=2C(=CC=C(C=2)C(F)(F)F)Cl)S1 SCJPAZKOYPVFRT-UHFFFAOYSA-N 0.000 claims 1
- 102000004310 Ion Channels Human genes 0.000 claims 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 1
- 210000001744 T-lymphocyte Anatomy 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 208000026935 allergic disease Diseases 0.000 claims 1
- 125000005336 allyloxy group Chemical group 0.000 claims 1
- 239000000427 antigen Substances 0.000 claims 1
- 102000036639 antigens Human genes 0.000 claims 1
- 108091007433 antigens Proteins 0.000 claims 1
- 210000003719 b-lymphocyte Anatomy 0.000 claims 1
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 230000016396 cytokine production Effects 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- OJENZBBDWGSYIQ-UHFFFAOYSA-N ethyl 4-[2-[(2,6-difluorobenzoyl)amino]-5-[3-(trifluoromethyl)phenyl]-1,3-thiazol-4-yl]-5-methyl-1,3-thiazole-2-carboxylate Chemical compound S1C(C(=O)OCC)=NC(C2=C(SC(NC(=O)C=3C(=CC=CC=3F)F)=N2)C=2C=C(C=CC=2)C(F)(F)F)=C1C OJENZBBDWGSYIQ-UHFFFAOYSA-N 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 210000000987 immune system Anatomy 0.000 claims 1
- 208000026278 immune system disease Diseases 0.000 claims 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 1
- 230000004968 inflammatory condition Effects 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- FKBHMHFOZOFWLT-UHFFFAOYSA-N methyl 2-[(2,6-difluorobenzoyl)amino]-5-(3-methoxyphenyl)-1,3-thiazole-4-carboxylate Chemical compound S1C(C=2C=C(OC)C=CC=2)=C(C(=O)OC)N=C1NC(=O)C1=C(F)C=CC=C1F FKBHMHFOZOFWLT-UHFFFAOYSA-N 0.000 claims 1
- JNYSAFDNFKBOSV-UHFFFAOYSA-N methyl 2-[(2,6-difluorobenzoyl)amino]-5-[2-prop-2-enoxy-5-(trifluoromethyl)phenyl]-1,3-thiazole-4-carboxylate Chemical compound S1C(C=2C(=CC=C(C=2)C(F)(F)F)OCC=C)=C(C(=O)OC)N=C1NC(=O)C1=C(F)C=CC=C1F JNYSAFDNFKBOSV-UHFFFAOYSA-N 0.000 claims 1
- KKQKKSSVBCUQPM-UHFFFAOYSA-N methyl 2-[(2,6-difluorobenzoyl)amino]-5-[3-(trifluoromethyl)phenyl]-1,3-thiazole-4-carboxylate Chemical compound S1C(C=2C=C(C=CC=2)C(F)(F)F)=C(C(=O)OC)N=C1NC(=O)C1=C(F)C=CC=C1F KKQKKSSVBCUQPM-UHFFFAOYSA-N 0.000 claims 1
- OTWZTUCHGGLLSA-UHFFFAOYSA-N methyl 3-[2-[(2,6-difluorobenzoyl)amino]-4-methyl-1,3-thiazol-5-yl]benzoate Chemical compound COC(=O)C1=CC=CC(C2=C(N=C(NC(=O)C=3C(=CC=CC=3F)F)S2)C)=C1 OTWZTUCHGGLLSA-UHFFFAOYSA-N 0.000 claims 1
- QHACIPXGPQFIKF-UHFFFAOYSA-N n-(2,6-difluorophenyl)-4-methyl-5-[3-(1,3,4-oxadiazol-2-yl)phenyl]-1,3-thiazole-2-carboxamide Chemical compound CC=1N=C(C(=O)NC=2C(=CC=CC=2F)F)SC=1C(C=1)=CC=CC=1C1=NN=CO1 QHACIPXGPQFIKF-UHFFFAOYSA-N 0.000 claims 1
- MPPWPOQZDGGEQT-UHFFFAOYSA-N n-[(2,6-difluorophenyl)methyl]-4-methyl-5-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-amine Chemical compound S1C(C=2C=C(C=CC=2)C(F)(F)F)=C(C)N=C1NCC1=C(F)C=CC=C1F MPPWPOQZDGGEQT-UHFFFAOYSA-N 0.000 claims 1
- HJSDVGSZOUHMHW-UHFFFAOYSA-N n-[4-(2,4-dichlorophenyl)-1,3-thiazol-2-yl]-2,6-difluorobenzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC1=NC(C=2C(=CC(Cl)=CC=2)Cl)=CS1 HJSDVGSZOUHMHW-UHFFFAOYSA-N 0.000 claims 1
- GHWIFWNGXKKHRQ-UHFFFAOYSA-N n-[4-(2,4-dimethyl-1,3-oxazol-5-yl)-5-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]-2,6-difluorobenzamide Chemical compound O1C(C)=NC(C)=C1C1=C(C=2C=C(C=CC=2)C(F)(F)F)SC(NC(=O)C=2C(=CC=CC=2F)F)=N1 GHWIFWNGXKKHRQ-UHFFFAOYSA-N 0.000 claims 1
- CLZHQVFQHIUZLD-UHFFFAOYSA-N n-[4-(2,5-dimethyl-1,3-thiazol-4-yl)-5-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]-2,6-difluorobenzamide Chemical compound S1C(C)=NC(C2=C(SC(NC(=O)C=3C(=CC=CC=3F)F)=N2)C=2C=C(C=CC=2)C(F)(F)F)=C1C CLZHQVFQHIUZLD-UHFFFAOYSA-N 0.000 claims 1
- MOEQXMVEEHRNSP-UHFFFAOYSA-N n-[4-(2-amino-1,3-thiazol-4-yl)-5-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]-2,6-difluorobenzamide Chemical compound S1C(N)=NC(C2=C(SC(NC(=O)C=3C(=CC=CC=3F)F)=N2)C=2C=C(C=CC=2)C(F)(F)F)=C1 MOEQXMVEEHRNSP-UHFFFAOYSA-N 0.000 claims 1
- NGMPCBBGTDPNJA-UHFFFAOYSA-N n-[4-(2-bromoacetyl)-5-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]-2,6-difluorobenzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC1=NC(C(=O)CBr)=C(C=2C=C(C=CC=2)C(F)(F)F)S1 NGMPCBBGTDPNJA-UHFFFAOYSA-N 0.000 claims 1
- ATOOTUUEXSMODA-UHFFFAOYSA-N n-[4-(3,4-dimethoxyphenyl)-5-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]-2,6-difluorobenzamide Chemical compound C1=C(OC)C(OC)=CC=C1C1=C(C=2C=C(C=CC=2)C(F)(F)F)SC(NC(=O)C=2C(=CC=CC=2F)F)=N1 ATOOTUUEXSMODA-UHFFFAOYSA-N 0.000 claims 1
- PAGANBXATYFCTF-UHFFFAOYSA-N n-[4-(4,5-dihydro-1,3-oxazol-2-yl)-5-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]-2,6-difluorobenzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC1=NC(C=2OCCN=2)=C(C=2C=C(C=CC=2)C(F)(F)F)S1 PAGANBXATYFCTF-UHFFFAOYSA-N 0.000 claims 1
- DVWZFYUJIJOMAU-UHFFFAOYSA-N n-[4-(4,5-dihydro-1h-imidazol-2-yl)-5-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]-2,6-difluorobenzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC1=NC(C=2NCCN=2)=C(C=2C=C(C=CC=2)C(F)(F)F)S1 DVWZFYUJIJOMAU-UHFFFAOYSA-N 0.000 claims 1
- WYAROCQKDHIRBZ-UHFFFAOYSA-N n-[4-(chloromethyl)-5-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]-2,6-difluorobenzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC1=NC(CCl)=C(C=2C=C(C=CC=2)C(F)(F)F)S1 WYAROCQKDHIRBZ-UHFFFAOYSA-N 0.000 claims 1
- ADUXGSRJWAACCF-UHFFFAOYSA-N n-[4-[(dimethylamino)methyl]-5-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]-2,6-difluorobenzamide Chemical compound S1C(C=2C=C(C=CC=2)C(F)(F)F)=C(CN(C)C)N=C1NC(=O)C1=C(F)C=CC=C1F ADUXGSRJWAACCF-UHFFFAOYSA-N 0.000 claims 1
- DPOXBSFZICYHBU-UHFFFAOYSA-N n-[4-[4-(dimethylamino)phenyl]-5-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]-2,6-difluorobenzamide Chemical compound C1=CC(N(C)C)=CC=C1C1=C(C=2C=C(C=CC=2)C(F)(F)F)SC(NC(=O)C=2C(=CC=CC=2F)F)=N1 DPOXBSFZICYHBU-UHFFFAOYSA-N 0.000 claims 1
- CTQZGJIKHFKHMN-UHFFFAOYSA-N n-[4-acetyl-5-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]-2,6-difluorobenzamide Chemical compound S1C(C=2C=C(C=CC=2)C(F)(F)F)=C(C(=O)C)N=C1NC(=O)C1=C(F)C=CC=C1F CTQZGJIKHFKHMN-UHFFFAOYSA-N 0.000 claims 1
- RXFOILPYBNWCIE-UHFFFAOYSA-N n-[4-amino-5-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]-2,6-difluorobenzamide Chemical compound S1C(C=2C=C(C=CC=2)C(F)(F)F)=C(N)N=C1NC(=O)C1=C(F)C=CC=C1F RXFOILPYBNWCIE-UHFFFAOYSA-N 0.000 claims 1
- AOYDHSCFPDWSFT-UHFFFAOYSA-N n-[4-chloro-5-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]-2,6-difluorobenzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC1=NC(Cl)=C(C=2C=C(C=CC=2)C(F)(F)F)S1 AOYDHSCFPDWSFT-UHFFFAOYSA-N 0.000 claims 1
- OOPHTDZEMSMIEU-UHFFFAOYSA-N n-[4-cyano-5-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]-2,6-difluorobenzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC1=NC(C#N)=C(C=2C=C(C=CC=2)C(F)(F)F)S1 OOPHTDZEMSMIEU-UHFFFAOYSA-N 0.000 claims 1
- ULKHOEUPZDRAII-UHFFFAOYSA-N n-[4-cyclopropyl-5-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]-2,6-difluorobenzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC1=NC(C2CC2)=C(C=2C=C(C=CC=2)C(F)(F)F)S1 ULKHOEUPZDRAII-UHFFFAOYSA-N 0.000 claims 1
- FXPXNKOOZOQPPT-UHFFFAOYSA-N n-[4-cyclopropyl-5-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]-3-methylpyridine-4-carboxamide Chemical compound CC1=CN=CC=C1C(=O)NC1=NC(C2CC2)=C(C=2C=C(C=CC=2)C(F)(F)F)S1 FXPXNKOOZOQPPT-UHFFFAOYSA-N 0.000 claims 1
- JDDNBJDXADBIJY-UHFFFAOYSA-N n-[4-ethenyl-5-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]-2,6-difluorobenzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC1=NC(C=C)=C(C=2C=C(C=CC=2)C(F)(F)F)S1 JDDNBJDXADBIJY-UHFFFAOYSA-N 0.000 claims 1
- ZRSZMDCTSHJHLX-UHFFFAOYSA-N n-[4-ethyl-5-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]-2,6-difluorobenzamide Chemical compound S1C(C=2C=C(C=CC=2)C(F)(F)F)=C(CC)N=C1NC(=O)C1=C(F)C=CC=C1F ZRSZMDCTSHJHLX-UHFFFAOYSA-N 0.000 claims 1
- HJFXFMQZSITWTM-UHFFFAOYSA-N n-[4-ethynyl-5-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]-2,6-difluorobenzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC1=NC(C#C)=C(C=2C=C(C=CC=2)C(F)(F)F)S1 HJFXFMQZSITWTM-UHFFFAOYSA-N 0.000 claims 1
- LTWAXZUUICFIJX-UHFFFAOYSA-N n-[5-(2,5-dibromothiophen-3-yl)-4-methyl-1,3-thiazol-2-yl]-2,6-difluorobenzamide Chemical compound S1C(C2=C(SC(Br)=C2)Br)=C(C)N=C1NC(=O)C1=C(F)C=CC=C1F LTWAXZUUICFIJX-UHFFFAOYSA-N 0.000 claims 1
- PZAQVTNPEIPHJZ-UHFFFAOYSA-N n-[5-(2,5-dimethoxyphenyl)-1,3-thiazol-2-yl]-2,6-difluorobenzamide Chemical compound COC1=CC=C(OC)C(C=2SC(NC(=O)C=3C(=CC=CC=3F)F)=NC=2)=C1 PZAQVTNPEIPHJZ-UHFFFAOYSA-N 0.000 claims 1
- AOZJRFYPYSNXLN-UHFFFAOYSA-N n-[5-(2,5-dimethoxyphenyl)-4-methyl-1,3-thiazol-2-yl]-2,6-difluorobenzamide Chemical compound COC1=CC=C(OC)C(C2=C(N=C(NC(=O)C=3C(=CC=CC=3F)F)S2)C)=C1 AOZJRFYPYSNXLN-UHFFFAOYSA-N 0.000 claims 1
- LNNQQBQEZYQADQ-UHFFFAOYSA-N n-[5-(2,5-dimethylcyclohexen-1-yl)-1,3-thiazol-2-yl]-3-methylpyridine-4-carboxamide Chemical compound C1C(C)CCC(C)=C1C(S1)=CN=C1NC(=O)C1=CC=NC=C1C LNNQQBQEZYQADQ-UHFFFAOYSA-N 0.000 claims 1
- BDHPUOMUSDUSIC-UHFFFAOYSA-N n-[5-(2-bromo-4,5-dimethoxyphenyl)-4-methyl-1,3-thiazol-2-yl]-2,6-difluorobenzamide Chemical compound C1=C(OC)C(OC)=CC(Br)=C1C1=C(C)N=C(NC(=O)C=2C(=CC=CC=2F)F)S1 BDHPUOMUSDUSIC-UHFFFAOYSA-N 0.000 claims 1
- QPUIXRJRQHUCDM-UHFFFAOYSA-N n-[5-(2-bromo-5-methoxyphenyl)-4-methyl-1,3-thiazol-2-yl]-2,6-difluorobenzamide Chemical compound COC1=CC=C(Br)C(C2=C(N=C(NC(=O)C=3C(=CC=CC=3F)F)S2)C)=C1 QPUIXRJRQHUCDM-UHFFFAOYSA-N 0.000 claims 1
- HASANRVKGSSJEU-UHFFFAOYSA-N n-[5-(2-bromopyridin-4-yl)-4-methyl-1,3-thiazol-2-yl]-2,6-difluorobenzamide Chemical compound S1C(C=2C=C(Br)N=CC=2)=C(C)N=C1NC(=O)C1=C(F)C=CC=C1F HASANRVKGSSJEU-UHFFFAOYSA-N 0.000 claims 1
- PEGUEQBFWKQFMO-UHFFFAOYSA-N n-[5-(2-cyanopyridin-4-yl)-4-methyl-1,3-thiazol-2-yl]-2,6-difluorobenzamide Chemical compound S1C(C=2C=C(N=CC=2)C#N)=C(C)N=C1NC(=O)C1=C(F)C=CC=C1F PEGUEQBFWKQFMO-UHFFFAOYSA-N 0.000 claims 1
- PVHZIASAHQCHBD-UHFFFAOYSA-N n-[5-(3,4-dimethoxyphenyl)-4-methyl-1,3-thiazol-2-yl]-2,6-difluorobenzamide Chemical compound C1=C(OC)C(OC)=CC=C1C1=C(C)N=C(NC(=O)C=2C(=CC=CC=2F)F)S1 PVHZIASAHQCHBD-UHFFFAOYSA-N 0.000 claims 1
- DTIKDGOJUZCYHB-UHFFFAOYSA-N n-[5-(3-cyanophenyl)-1,3-thiazol-2-yl]-2,6-difluorobenzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC1=NC=C(C=2C=C(C=CC=2)C#N)S1 DTIKDGOJUZCYHB-UHFFFAOYSA-N 0.000 claims 1
- WEBIYSDQKPNOKD-UHFFFAOYSA-N n-[5-(3-cyanophenyl)-4-methyl-1,3-thiazol-2-yl]-2,6-difluorobenzamide Chemical compound S1C(C=2C=C(C=CC=2)C#N)=C(C)N=C1NC(=O)C1=C(F)C=CC=C1F WEBIYSDQKPNOKD-UHFFFAOYSA-N 0.000 claims 1
- PAQGXAZFZGYWLX-UHFFFAOYSA-N n-[5-(4-chloropyridin-2-yl)-4-methyl-1,3-thiazol-2-yl]-2,6-difluorobenzamide Chemical compound S1C(C=2N=CC=C(Cl)C=2)=C(C)N=C1NC(=O)C1=C(F)C=CC=C1F PAQGXAZFZGYWLX-UHFFFAOYSA-N 0.000 claims 1
- BKLCIZQQRGIQBZ-UHFFFAOYSA-N n-[5-(4-chloropyridin-2-yl)-4-methyl-1,3-thiazol-2-yl]-3-methylpyridine-4-carboxamide;hydrochloride Chemical compound Cl.S1C(C=2N=CC=C(Cl)C=2)=C(C)N=C1NC(=O)C1=CC=NC=C1C BKLCIZQQRGIQBZ-UHFFFAOYSA-N 0.000 claims 1
- GNMHWICCICZVAN-UHFFFAOYSA-N n-[5-(5-bromothiophen-2-yl)-4-methyl-1,3-thiazol-2-yl]-2,6-difluorobenzamide Chemical compound S1C(C=2SC(Br)=CC=2)=C(C)N=C1NC(=O)C1=C(F)C=CC=C1F GNMHWICCICZVAN-UHFFFAOYSA-N 0.000 claims 1
- KVXFLFROOBMUGT-UHFFFAOYSA-N n-[5-(7-bromo-1,3-benzodioxol-5-yl)-4-methyl-1,3-thiazol-2-yl]-2,6-difluorobenzamide Chemical compound S1C(C=2C=C(Br)C=3OCOC=3C=2)=C(C)N=C1NC(=O)C1=C(F)C=CC=C1F KVXFLFROOBMUGT-UHFFFAOYSA-N 0.000 claims 1
- ZGQUIBYTJLLUPE-UHFFFAOYSA-N n-[5-(7-cyano-1,3-benzodioxol-5-yl)-4-methyl-1,3-thiazol-2-yl]-2,6-difluorobenzamide Chemical compound S1C(C=2C=C(C=3OCOC=3C=2)C#N)=C(C)N=C1NC(=O)C1=C(F)C=CC=C1F ZGQUIBYTJLLUPE-UHFFFAOYSA-N 0.000 claims 1
- QJYLREOKBQKMTO-UHFFFAOYSA-N n-[5-[2-chloro-5-(trifluoromethyl)phenyl]-1,3,4-thiadiazol-2-yl]-2,6-difluorobenzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC1=NN=C(C=2C(=CC=C(C=2)C(F)(F)F)Cl)S1 QJYLREOKBQKMTO-UHFFFAOYSA-N 0.000 claims 1
- YCEVANSKDGKSIN-UHFFFAOYSA-N n-[5-[2-chloro-5-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]-2,6-difluorobenzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC1=NC=C(C=2C(=CC=C(C=2)C(F)(F)F)Cl)S1 YCEVANSKDGKSIN-UHFFFAOYSA-N 0.000 claims 1
- WKPSQKLBNOMUMS-UHFFFAOYSA-N n-[5-[4-(dimethylamino)phenyl]-4-methyl-1,3-thiazol-2-yl]-2,6-difluorobenzamide Chemical compound C1=CC(N(C)C)=CC=C1C1=C(C)N=C(NC(=O)C=2C(=CC=CC=2F)F)S1 WKPSQKLBNOMUMS-UHFFFAOYSA-N 0.000 claims 1
- JJUHBUKWNCYFHU-UHFFFAOYSA-N n-[5-[4-(dimethylamino)phenyl]-4-methyl-1,3-thiazol-2-yl]-3-methylpyridine-4-carboxamide Chemical compound C1=CC(N(C)C)=CC=C1C1=C(C)N=C(NC(=O)C=2C(=CN=CC=2)C)S1 JJUHBUKWNCYFHU-UHFFFAOYSA-N 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 1
- 150000002790 naphthalenes Chemical class 0.000 claims 1
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 1
- 125000004304 oxazol-5-yl group Chemical group O1C=NC=C1* 0.000 claims 1
- 230000035755 proliferation Effects 0.000 claims 1
- WQRBOENCMVUGFG-UHFFFAOYSA-M sodium;(2,6-difluorobenzoyl)-[4-methyl-5-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]azanide Chemical compound [Na+].S1C(C=2C=C(C=CC=2)C(F)(F)F)=C(C)N=C1[N-]C(=O)C1=C(F)C=CC=C1F WQRBOENCMVUGFG-UHFFFAOYSA-M 0.000 claims 1
- MXTFDIZITLYYSU-UHFFFAOYSA-M sodium;(3-methylpyridine-4-carbonyl)-[4-methyl-5-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]azanide Chemical compound [Na+].S1C(C=2C=C(C=CC=2)C(F)(F)F)=C(C)N=C1[N-]C(=O)C1=CC=NC=C1C MXTFDIZITLYYSU-UHFFFAOYSA-M 0.000 claims 1
- 230000001629 suppression Effects 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- GGNIKGLUPSHSBV-UHFFFAOYSA-N thiazole-5-carboxamide Chemical compound NC(=O)C1=CN=CS1 GGNIKGLUPSHSBV-UHFFFAOYSA-N 0.000 claims 1
- 150000003557 thiazoles Chemical class 0.000 claims 1
- 0 CC(CCC(*)=C1)=C1c([s]1)c(*)nc1I* Chemical compound CC(CCC(*)=C1)=C1c([s]1)c(*)nc1I* 0.000 description 7
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| CN100406567C (zh) * | 2002-01-22 | 2008-07-30 | 生物材料公司 | 生物可降解聚合物的干燥方法 |
| WO2007087441A2 (en) * | 2006-01-25 | 2007-08-02 | Synta Pharmaceuticals Corp. | Substituted aromatic compounds for inflammation and immune-related uses |
| WO2007087442A2 (en) * | 2006-01-25 | 2007-08-02 | Synta Pharmaceuticals Corp. | Substituted biaryl compounds for inflammation and immune-related uses |
| US20070275960A1 (en) * | 2006-01-25 | 2007-11-29 | Synta Pharmaceuticals Corp. | Phenyl and pyridyl compounds for inflammation and immune-related uses |
| WO2007087443A2 (en) | 2006-01-25 | 2007-08-02 | Synta Pharmaceuticals Corp. | Vinyl-phenyl derivatives for inflammation and immune-related uses |
| US8119643B2 (en) * | 2006-03-20 | 2012-02-21 | Synta Pharmaceuticals Corp. | Benzoimidazolyl-pyrazine compounds for inflammation and immune-related uses |
| US8779154B2 (en) * | 2006-09-26 | 2014-07-15 | Qinglin Che | Fused ring compounds for inflammation and immune-related uses |
| US20090099242A1 (en) | 2007-08-15 | 2009-04-16 | Cuny Gregory D | Heterocyclic inhibitors of necroptosis |
| JP5411141B2 (ja) | 2007-09-10 | 2014-02-12 | カルシメディカ，インク． | 細胞内カルシウムを調節する化合物 |
| US8389567B2 (en) * | 2007-12-12 | 2013-03-05 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| EP2240029A4 (en) * | 2008-01-07 | 2012-08-22 | Synta Pharmaceuticals Corp | COMPOUNDS FOR USE AGAINST INFLAMMATORY AND IMMUNOMIC DISEASES |
| US7906553B2 (en) * | 2008-08-27 | 2011-03-15 | Calcimedica, Inc. | Substituted thiophene modulators of intracellular calcium |
| US8524763B2 (en) * | 2008-09-22 | 2013-09-03 | Calcimedica, Inc. | Inhibitors of store operated calcium release |
| US8536185B2 (en) | 2008-09-22 | 2013-09-17 | Cayman Chemical Company, Incorporated | Multiheteroaryl compounds as inhibitors of H-PGDS and their use for treating prostaglandin D2 mediated diseases |
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| WO2005002673A1 (en) | 2003-07-03 | 2005-01-13 | Astex Therapeutics Limited | Raf kinase inhibitors |
| RU2006104697A (ru) | 2003-07-16 | 2006-06-27 | Инститьют Оф Медисинал Молекьюлар Дизайн. Инк. (Jp) | Лекарственное средство для лечения пигментации кожи |
| CN1826121B (zh) * | 2003-07-23 | 2013-05-29 | 幸讬制药公司 | 苯基与吡啶基衍生物用于制备调控钙离子释放活化钙离子通道的药物的用途 |
| US20050107438A1 (en) * | 2003-09-03 | 2005-05-19 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition comprising 3-[(2-{[4-(Hexyloxycarbonylaminoiminomethyl) phenylamino]-methyl}-1-methyl-1H-benzimidazol-5-carbonyl)-pyridin-2-yl-amino]-propionic acid ethyl ester or a salt therefore |
| RU2006111093A (ru) * | 2003-09-06 | 2007-10-27 | Вертекс Фармасьютикалз Инкорпорейтед (Us) | Модуляторы атр-связывающих кассетных транспортеров |
| PT1671635E (pt) * | 2003-10-08 | 2012-01-17 | Meiji Seika Pharma Co Ltd | Composição de antibiótico amorfo contendo cefditoreno pivoxil |
| WO2005044194A2 (en) | 2003-10-28 | 2005-05-19 | Pharmacia Corporation | TREATMENT OR PREVENTION OF NEOPLASIA BY USE OF AN Hsp90 INHIBITOR |
| CA2551611C (en) * | 2003-12-26 | 2013-06-25 | Kyowa Kirin Co., Ltd. | Thiazole derivatives for treating or preventing parkinson's disease |
| WO2005091752A2 (en) * | 2004-03-25 | 2005-10-06 | Synta Pharmaceuticals Corp. | Acrylonitrile derivatives for inflammation and immune-related uses |
| US7902356B2 (en) | 2004-12-17 | 2011-03-08 | Eli Lilly And Company | Thiazolopyridinone derivates as MCH receptor antagonists |
| DK1885716T3 (da) | 2005-05-24 | 2013-02-11 | Merck Serono Sa | Thiazolderivater og anvendelse deraf |
| WO2007087441A2 (en) * | 2006-01-25 | 2007-08-02 | Synta Pharmaceuticals Corp. | Substituted aromatic compounds for inflammation and immune-related uses |
| US20070275960A1 (en) * | 2006-01-25 | 2007-11-29 | Synta Pharmaceuticals Corp. | Phenyl and pyridyl compounds for inflammation and immune-related uses |
| WO2007087442A2 (en) * | 2006-01-25 | 2007-08-02 | Synta Pharmaceuticals Corp. | Substituted biaryl compounds for inflammation and immune-related uses |
| WO2007087443A2 (en) * | 2006-01-25 | 2007-08-02 | Synta Pharmaceuticals Corp. | Vinyl-phenyl derivatives for inflammation and immune-related uses |
-
2007
- 2007-01-25 CA CA002639910A patent/CA2639910A1/en not_active Abandoned
- 2007-01-25 TW TW096102794A patent/TWI444370B/zh not_active IP Right Cessation
- 2007-01-25 US US11/698,772 patent/US8455658B2/en not_active Expired - Fee Related
- 2007-01-25 AU AU2007208225A patent/AU2007208225B2/en not_active Ceased
- 2007-01-25 JP JP2008552423A patent/JP2009524677A/ja active Pending
- 2007-01-25 WO PCT/US2007/002121 patent/WO2007087427A2/en not_active Ceased
- 2007-01-25 EP EP07717039A patent/EP1983980A4/en not_active Withdrawn
-
2013
- 2013-05-16 US US13/895,590 patent/US20140135331A9/en not_active Abandoned
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