JP2009524677A5 - - Google Patents
Download PDFInfo
- Publication number
- 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
Links
- -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
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US76197406P | 2006-01-25 | 2006-01-25 | |
| US76193306P | 2006-01-25 | 2006-01-25 | |
| PCT/US2007/002121 WO2007087427A2 (en) | 2006-01-25 | 2007-01-25 | Thiazole and thiadiazole compounds for inflammation and immune-related uses |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2009524677A JP2009524677A (ja) | 2009-07-02 |
| JP2009524677A5 true JP2009524677A5 (enExample) | 2010-03-11 |
Family
ID=38309864
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008552423A Pending JP2009524677A (ja) | 2006-01-25 | 2007-01-25 | 炎症および免疫関連使用用のチアゾールおよびチアジアゾール化合物 |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US8455658B2 (enExample) |
| EP (1) | EP1983980A4 (enExample) |
| JP (1) | JP2009524677A (enExample) |
| AU (1) | AU2007208225B2 (enExample) |
| CA (1) | CA2639910A1 (enExample) |
| TW (1) | TWI444370B (enExample) |
| WO (1) | WO2007087427A2 (enExample) |
Families Citing this family (110)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2003201573B2 (en) * | 2002-01-22 | 2009-02-26 | Biomatera Inc. | Method of drying biodegradable polymers |
| JP2009524683A (ja) | 2006-01-25 | 2009-07-02 | シンタ ファーマシューティカルズ コーポレーション | 炎症および免疫関連用途のためのビニル−フェニル誘導体 |
| CA2640090A1 (en) * | 2006-01-25 | 2007-08-02 | Synta Pharmaceuticals Corp. | Substituted aromatic compounds for inflammation and immune-related uses |
| CA2639913A1 (en) * | 2006-01-25 | 2007-08-02 | Synta Pharmaceutical Corp. | Phenyl and pyridyl compounds for inflammation and immune-related uses |
| JP2009528273A (ja) * | 2006-01-25 | 2009-08-06 | シンタ ファーマシューティカルズ コーポレーション | 炎症および免疫関連使用用の置換ビアリール化合物 |
| CA2645434A1 (en) | 2006-03-20 | 2007-09-27 | Synta Pharmaceutical Corp. | Benzoimidazolyl-parazine 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 |
| CA2696349A1 (en) | 2007-08-15 | 2009-02-19 | President And Fellows Of Harvard College | Heterocyclic inhibitors of necroptosis |
| CN101854933A (zh) | 2007-09-10 | 2010-10-06 | 钙医学公司 | 调节细胞内钙的化合物 |
| WO2009076454A2 (en) * | 2007-12-12 | 2009-06-18 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| US20110052643A1 (en) * | 2008-01-07 | 2011-03-03 | Synta Pharmaceuticals Corp. | Compounds for inflammation and immune-related uses |
| US7906553B2 (en) * | 2008-08-27 | 2011-03-15 | Calcimedica, Inc. | Substituted thiophene modulators of intracellular calcium |
| MY154000A (en) | 2008-09-22 | 2015-04-30 | Cayman Chem Co | Multiheteroaryl compounds as inhibitors of h-pgds and their use for treating prostaglandin d2 mediated diseases |
| US8524763B2 (en) * | 2008-09-22 | 2013-09-03 | Calcimedica, Inc. | Inhibitors of store operated calcium release |
| US8143269B2 (en) * | 2008-10-03 | 2012-03-27 | Calcimedica, Inc. | Inhibitors of store operated calcium release |
| UA107791C2 (en) | 2009-05-05 | 2015-02-25 | Dow Agrosciences Llc | Pesticidal compositions |
| EP2477982A4 (en) * | 2009-09-16 | 2013-04-03 | Calcimedica Inc | COMPOUNDS THAT MODULATE INTRACELLULAR CALCIUM |
| EP2305660A1 (en) * | 2009-09-25 | 2011-04-06 | Almirall, S.A. | New thiadiazole derivatives |
| US8377970B2 (en) | 2009-10-08 | 2013-02-19 | Rhizen Pharmaceuticals Sa | Modulators of calcium release-activated calcium channel |
| US8993612B2 (en) | 2009-10-08 | 2015-03-31 | Rhizen Pharmaceuticals Sa | Modulators of calcium release-activated calcium channel and methods for treatment of non-small cell lung cancer |
| US10703722B2 (en) | 2010-04-27 | 2020-07-07 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| CA2797533A1 (en) | 2010-04-27 | 2011-11-10 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| PL2563776T3 (pl) | 2010-04-27 | 2017-01-31 | Calcimedica Inc | Związki, które modulują wewnątrzkomórkowy wapń |
| EP2568809A4 (en) | 2010-05-12 | 2013-11-06 | Univ Vanderbilt | HETEROCYCLIC ALLOSTERE SULFON MGLUR4 POTENTIATORS, COMPOSITIONS AND METHODS OF TREATING NEUROLOGICAL DYSFUNCTIONS |
| BR112012033715A2 (pt) * | 2010-07-02 | 2016-11-22 | Gilead Sciences Inc | inibidores de quinase de regulação de sinal de apoptose. |
| WO2012027710A2 (en) | 2010-08-27 | 2012-03-01 | Calcimedica Inc. | Compounds that modulate intracellular calcium |
| MX355782B (es) | 2010-11-03 | 2018-04-30 | Dow Agrosciences Llc | Composiciones pesticidas y procesos relacionados a las mismas. |
| CN102532123B (zh) * | 2010-12-29 | 2016-03-09 | 中国医学科学院药物研究所 | 噻唑-5-甲酰胺化合物、及其制法和药物组合物与用途 |
| UA112539C2 (uk) | 2011-03-03 | 2016-09-26 | Новартіс Аг | Спосіб одержання похідних 2-карбоксамідциклоаміносечовини |
| US9255072B2 (en) * | 2011-03-04 | 2016-02-09 | National Health Rsearch Institutes | Pyrazole compounds and thiazole compounds as protein kinases inhibitors |
| WO2012121168A1 (ja) * | 2011-03-04 | 2012-09-13 | 国立大学法人京都大学 | キナーゼ阻害剤 |
| JP5985611B2 (ja) * | 2011-05-03 | 2016-09-06 | シンタ ファーマシューティカルズ コーポレーション | 炎症および免疫関連用途のための化合物 |
| US20120316182A1 (en) | 2011-06-10 | 2012-12-13 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| CN103058949A (zh) * | 2011-10-18 | 2013-04-24 | 华东理工大学 | 做为dhodh抑制剂的噻唑衍生物及其应用 |
| WO2013059677A1 (en) | 2011-10-19 | 2013-04-25 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| CN104010505B (zh) | 2011-10-26 | 2017-03-15 | 陶氏益农公司 | 杀虫组合物和与其相关的方法 |
| US9499533B2 (en) | 2012-03-27 | 2016-11-22 | Shionogi & Co., Ltd. | Aromatic 5-membered heterocyclic derivative having TRPV4-Inhibiting activity |
| US9282739B2 (en) | 2012-04-27 | 2016-03-15 | Dow Agrosciences Llc | Pesticidal compositions and processes related thereto |
| BR122014028247A2 (pt) | 2012-04-27 | 2019-05-07 | Dow Agrosciences Llc | composições pesticidas, processo para controlar praga, uso de uma molécula, processo para aumentar a saúde, rendimento, vigor, qualidade ou tolerância de uma planta e processos para produção de compostos |
| US9708288B2 (en) | 2012-04-27 | 2017-07-18 | Dow Agrosciences Llc | Pesticidal compositions and processes related thereto |
| KR101742954B1 (ko) * | 2012-05-31 | 2017-06-02 | 페넥스 파마슈티컬스 아게 | 고아 핵 수용체 ror[감마]의 조절제로서의 카복사미드 또는 설폰아미드가 치환된 티아졸 및 관련된 유도체 |
| US9512116B2 (en) | 2012-10-12 | 2016-12-06 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| EP2738172A1 (en) | 2012-11-28 | 2014-06-04 | Almirall, S.A. | New bicyclic compounds as crac channel modulators |
| EP2746260A1 (en) | 2012-12-21 | 2014-06-25 | Basf Se | Substituted [1,2,4]triazole and imidazole compounds |
| EP2746259A1 (en) | 2012-12-21 | 2014-06-25 | Basf Se | Substituted [1,2,4]triazole and imidazole compounds |
| WO2014108337A1 (en) | 2013-01-10 | 2014-07-17 | Grünenthal GmbH | Pyrazolyl-based carboxamides i as crac channel inhibitors |
| AU2014204977A1 (en) | 2013-01-10 | 2015-08-20 | Grunenthal Gmbh | Pyrazolyl-based carboxamides II as CRAC channel inhibitors |
| US20160024098A1 (en) | 2013-03-15 | 2016-01-28 | President And Fellows Of Harvard College | Hybrid necroptosis inhibitors |
| EP3016950B1 (en) | 2013-07-02 | 2017-06-07 | Bristol-Myers Squibb Company | Tricyclic pyrido-carboxamide derivatives as rock inhibitors |
| CN105492444B (zh) | 2013-07-02 | 2018-09-07 | 百时美施贵宝公司 | 作为rock抑制剂的三环吡啶-甲酰胺衍生物 |
| EP2848615A1 (en) | 2013-07-03 | 2015-03-18 | Almirall, S.A. | New pyrazole derivatives as CRAC channel modulators |
| KR20160072155A (ko) | 2013-10-17 | 2016-06-22 | 다우 아그로사이언시즈 엘엘씨 | 살충성 화합물의 제조 방법 |
| MX2016004941A (es) | 2013-10-17 | 2016-06-28 | Dow Agrosciences Llc | Proceso para la preparacion de compuestos plaguicidas. |
| MX2016004946A (es) | 2013-10-17 | 2016-06-28 | Dow Agrosciences Llc | Procesos para la preparacion de compuestos plaguicidas. |
| US9102655B2 (en) | 2013-10-17 | 2015-08-11 | Dow Agrosciences Llc | Processes for the preparation of pesticidal compounds |
| JP2016536295A (ja) | 2013-10-17 | 2016-11-24 | ダウ アグロサイエンシィズ エルエルシー | 有害生物防除性化合物の製造方法 |
| EP3057430A4 (en) | 2013-10-17 | 2017-09-13 | Dow AgroSciences LLC | Processes for the preparation of pesticidal compounds |
| BR112016007518A2 (pt) | 2013-10-17 | 2017-08-01 | Dow Agrosciences Llc | processos para a preparação de compostos pesticidas |
| AR098092A1 (es) | 2013-10-22 | 2016-05-04 | Dow Agrosciences Llc | Composiciones plaguicidas sinérgicas y los métodos relacionados |
| BR112016008045B1 (pt) | 2013-10-22 | 2019-12-24 | Dow Agrosciences Llc | composição pesticida |
| WO2015061149A1 (en) | 2013-10-22 | 2015-04-30 | Dow Agrosciences Llc | Synergistic pesticidal compositions and related methods |
| AR098094A1 (es) | 2013-10-22 | 2016-05-04 | Dow Agrosciences Llc | Composiciones plaguicidas sinérgicas y métodos relacionados |
| NZ719776A (en) | 2013-10-22 | 2017-06-30 | Dow Agrosciences Llc | Synergistic pesticidal compositions and related methods |
| MX2016005335A (es) | 2013-10-22 | 2017-01-05 | Dow Agrosciences Llc | Composiciones pesticidas y metodos relacionados. |
| TW201519775A (zh) | 2013-10-22 | 2015-06-01 | Dow Agrosciences Llc | 協同性殺蟲組成物及相關方法（七） |
| KR20160075624A (ko) | 2013-10-22 | 2016-06-29 | 다우 아그로사이언시즈 엘엘씨 | 살충 조성물 및 관련 방법 |
| MX2016005308A (es) | 2013-10-22 | 2016-08-08 | Dow Agrosciences Llc | Composiciones pesticidas sinergicas y metodos relacionados. |
| MX2016005319A (es) | 2013-10-22 | 2016-08-12 | Dow Agrosciences Llc | Composiciones pesticidas y metodos relacionados. |
| RU2667777C2 (ru) | 2013-10-22 | 2018-09-24 | ДАУ АГРОСАЙЕНСИЗ ЭлЭлСи | Пестицидные композиции и связанные с ними способы |
| NZ720113A (en) | 2013-10-22 | 2017-06-30 | Dow Agrosciences Llc | Synergistic pesticidal compositions and related methods |
| US9282740B2 (en) | 2013-10-22 | 2016-03-15 | Dow Agrosciences Llc | Synergistic pesticidal compositions and related methods |
| CN105828611A (zh) | 2013-10-22 | 2016-08-03 | 美国陶氏益农公司 | 协同杀虫组合物和相关方法 |
| WO2015061145A1 (en) | 2013-10-22 | 2015-04-30 | Dow Agrosciences Llc | Synergistic pesticidal compositions and related methods |
| CA2926345A1 (en) | 2013-10-22 | 2015-04-30 | Dow Agrosciences Llc | Synergistic pesticidal compositions and related methods |
| US9497966B2 (en) | 2013-10-22 | 2016-11-22 | Dow Agrosciences Llc | Pesticidal compositions and related methods |
| JP6327841B2 (ja) * | 2013-12-06 | 2018-05-23 | 住友精化株式会社 | 芳香族チアゾール化合物の製造方法 |
| WO2015197187A1 (en) | 2014-06-24 | 2015-12-30 | Grünenthal GmbH | Pyrazolyl-based carboxamides v |
| EP3174856A4 (en) | 2014-07-31 | 2018-01-10 | Dow AgroSciences LLC | Process for the preparation of 3-(3-chloro-1h-pyrazol-1-yl)pyridine |
| CN106470976A (zh) | 2014-07-31 | 2017-03-01 | 美国陶氏益农公司 | 制备3‑(3‑氯‑1h‑吡唑‑1‑基)吡啶的方法 |
| WO2016018443A1 (en) | 2014-07-31 | 2016-02-04 | Dow Agrosciences Llc | Process for the preparation of 3-(3-chloro-1h-pyrazol-1-yl)pyridine |
| WO2016028328A1 (en) | 2014-08-19 | 2016-02-25 | Dow Agrosciences Llc | Process for the preparation of 3-(3-chloro-1h-pyrazol-1-yl)pyridine |
| CN107074775A (zh) | 2014-09-12 | 2017-08-18 | 美国陶氏益农公司 | 3‑(3‑氯‑1h‑吡唑‑1‑基)吡啶的制备方法 |
| SMT201900706T1 (it) | 2014-10-30 | 2020-01-14 | Janssen Pharmaceutica Nv | Tiazoli sostituiti con ammide come modulatori di rorgammat |
| JOP20200117A1 (ar) | 2014-10-30 | 2017-06-16 | Janssen Pharmaceutica Nv | كحولات ثلاثي فلوروميثيل كمُعدلات للمستقبل النووي جاما تي المرتبط بحمض الريتيونَويك ROR?t |
| RS58250B1 (sr) | 2014-10-30 | 2019-03-29 | Janssen Pharmaceutica Nv | Tiazoli kao modulatori roryt |
| EA036265B1 (ru) | 2015-02-27 | 2020-10-20 | Кальцимедика, Инк. | Лечение панкреатита |
| WO2016183173A1 (en) * | 2015-05-12 | 2016-11-17 | Avista Pharma Solutions | Antiparasitic compounds |
| CA2995094A1 (en) | 2015-08-07 | 2017-02-16 | Calcimedica, Inc. | Use of crac channel inhibitors for the treatment of stroke and traumatic brain injury |
| WO2017109793A1 (en) * | 2015-12-21 | 2017-06-29 | Council Of Scientific & Industrial Research | Novel 1,2,3 triazole-thiazole compounds, process for preparation and use thereof |
| WO2017135786A1 (ko) * | 2016-02-05 | 2017-08-10 | 연세대학교 산학협력단 | 신규 아미드 화합물 및 이의 용도 |
| EP3442952A1 (en) * | 2016-04-11 | 2019-02-20 | Genfit | Methods of treatment of cholestasis and fibrosis |
| HUE052886T2 (hu) | 2016-04-11 | 2021-05-28 | Genfit | Módszerek kolesztázisos és fibrotikus betegségek kezelésére |
| TW201803869A (zh) | 2016-04-27 | 2018-02-01 | 健生藥品公司 | 作為ＲＯＲγＴ調節劑之６－胺基吡啶－３－基噻唑 |
| CN105943535B (zh) * | 2016-05-23 | 2017-05-31 | 泉州市景江电子科技有限公司 | 一种治疗乙肝的药物组合物 |
| JP2020503336A (ja) | 2016-12-29 | 2020-01-30 | ダウ アグロサイエンシィズ エルエルシー | 殺有害生物化合物の調製方法 |
| US10233155B2 (en) | 2016-12-29 | 2019-03-19 | Dow Agrosciences Llc | Processes for the preparation of pesticide compounds |
| CN108299418A (zh) * | 2017-09-14 | 2018-07-20 | 刘双伟 | 一种抗过敏和哮喘的噻唑基烟酰胺类化合物的合成方法 |
| CN107400124A (zh) * | 2017-09-14 | 2017-11-28 | 刘双伟 | 一种烟酰胺类化合物、合成路线及其在制备抗过敏药物中的应用 |
| JP2021527660A (ja) | 2018-06-18 | 2021-10-14 | ヤンセン ファーマシューティカ エヌ．ベー． | ＲＯＲγｔのモジュレータとしてのフェニル及びピリジニル置換イミダゾール |
| US10975037B2 (en) | 2018-06-18 | 2021-04-13 | Janssen Pharmaceutica Nv | Phenyl substituted pyrazoles as modulators of RORγt |
| ES2928246T3 (es) | 2018-06-18 | 2022-11-16 | Janssen Pharmaceutica Nv | 6-aminopiridin-3-il pirazoles como moduladores de RORyt |
| CN112292373A (zh) | 2018-06-18 | 2021-01-29 | 詹森药业有限公司 | 作为RORγt的调节剂的吡啶基吡唑类 |
| MX2021003094A (es) | 2018-09-14 | 2021-05-12 | Rhizen Pharmaceuticals A G | Composiciones que comprenden un inhibidor de crac y un corticosteroide y métodos de uso de estas. |
| KR102732033B1 (ko) * | 2019-07-26 | 2024-11-20 | 아주대학교산학협력단 | Tlr7 및 tlr9의 신호전달 경로를 억제하는 신규한 소분자 화합물 및 그 용도 |
| AR120896A1 (es) * | 2019-12-25 | 2022-03-30 | Astellas Pharma Inc | COMPUESTO DE PIRIDAZINIL-TIAZOLCARBOXAMIDA COMO INHIBIDORES DE DGKz |
| CA3167339A1 (en) | 2020-01-13 | 2021-07-22 | Verge Analytics, Inc. | Substituted pyrazolo-pyrimidines and uses thereof |
| CR20230415A (es) * | 2020-11-30 | 2023-09-08 | Kotobuki Pharmaceutical Co Ltd | Compuesto de heteroarilcarboxamida |
| CN116199682B (zh) * | 2023-03-17 | 2025-04-22 | 凯思凯迪（上海）医药科技有限公司 | 一种苯基噻唑基苯甲酰胺类化合物及其应用 |
| KR20250144817A (ko) * | 2024-03-27 | 2025-10-13 | 동국대학교 산학협력단 | 신규 옥사다이아졸 유도체 및 이를 포함하는 암 예방 또는 치료용 조성물 |
| CN118415982B (zh) * | 2024-04-15 | 2024-12-10 | 山东京卫制药有限公司 | 一种硝酸2-（4-甲基噻唑-5-基）乙酯盐酸盐鼻喷剂及其制备方法 |
Family Cites Families (61)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3536809A (en) * | 1969-02-17 | 1970-10-27 | Alza Corp | Medication method |
| US3598123A (en) * | 1969-04-01 | 1971-08-10 | Alza Corp | Bandage for administering drugs |
| US3794636A (en) * | 1971-09-03 | 1974-02-26 | Uniroyal Ltd | Process for preparation of thiazole hydrohalides |
| US3845770A (en) * | 1972-06-05 | 1974-11-05 | Alza Corp | Osmatic dispensing device for releasing beneficial agent |
| US3916899A (en) * | 1973-04-25 | 1975-11-04 | Alza Corp | Osmotic dispensing device with maximum and minimum sizes for the passageway |
| US4008719A (en) * | 1976-02-02 | 1977-02-22 | Alza Corporation | Osmotic system having laminar arrangement for programming delivery of active agent |
| GR65893B (enExample) | 1976-02-09 | 1980-12-01 | Lilly Co Eli | |
| US4141984A (en) * | 1976-11-10 | 1979-02-27 | Eli Lilly And Company | N-(1,3,4-thiadiazol-2-yl)benzamides |
| DD138903A1 (de) | 1978-08-25 | 1979-11-28 | Hans U Kibbel | Verfahren zur herstellung von 4-alkylmercapto-2-aryl-5-aryliden-imino-thiazolen |
| DD222022A1 (de) | 1984-02-27 | 1985-05-08 | Pieck Uni Rostock W | Verfahren zur herstellung von alkylammonium 2-aryl-5-benzyliden-aminothiazol-4-thiolaten |
| IE58110B1 (en) * | 1984-10-30 | 1993-07-14 | Elan Corp Plc | Controlled release powder and process for its preparation |
| DE3864248D1 (de) * | 1987-12-14 | 1991-09-19 | Sawai Seiyaku Kk | Carboxamide mit tetrazol- und thiazol-ringen und ihre anwendung. |
| JPH0228175A (ja) | 1987-12-14 | 1990-01-30 | Sawai Seiyaku Kk | チアゾール環およびテトラゾール環を有するカルボキシアミド誘導体およびその用途 |
| US5073543A (en) * | 1988-07-21 | 1991-12-17 | G. D. Searle & Co. | Controlled release formulations of trophic factors in ganglioside-lipsome vehicle |
| IT1229203B (it) * | 1989-03-22 | 1991-07-25 | Bioresearch Spa | Impiego di acido 5 metiltetraidrofolico, di acido 5 formiltetraidrofolico e dei loro sali farmaceuticamente accettabili per la preparazione di composizioni farmaceutiche in forma a rilascio controllato attive nella terapia dei disturbi mentali organici e composizioni farmaceutiche relative. |
| US5244867A (en) * | 1989-09-26 | 1993-09-14 | Basf Aktiengesellschaft | Oxazole- and thiazolecarboxamides |
| US5120548A (en) * | 1989-11-07 | 1992-06-09 | Merck & Co., Inc. | Swelling modulated polymeric drug delivery device |
| US5733566A (en) * | 1990-05-15 | 1998-03-31 | Alkermes Controlled Therapeutics Inc. Ii | Controlled release of antiparasitic agents in animals |
| FR2677356B1 (fr) * | 1991-06-05 | 1995-03-17 | Sanofi Sa | Derives heterocycliques d'acylamino-2 thiazoles-5 substitues, leur preparation et compositions pharmaceutiques en contenant. |
| US5580578A (en) * | 1992-01-27 | 1996-12-03 | Euro-Celtique, S.A. | Controlled release formulations coated with aqueous dispersions of acrylic polymers |
| US5591767A (en) * | 1993-01-25 | 1997-01-07 | Pharmetrix Corporation | Liquid reservoir transdermal patch for the administration of ketorolac |
| AU7551894A (en) * | 1993-09-09 | 1995-03-27 | E.I. Du Pont De Nemours And Company | Fungicidal, miticidal and arthropodicidal aminopyrimidines |
| JPH07149746A (ja) | 1993-11-30 | 1995-06-13 | Hisamitsu Pharmaceut Co Inc | 新規な２−置換アミノチアゾール誘導体 |
| IT1270594B (it) * | 1994-07-07 | 1997-05-07 | Recordati Chem Pharm | Composizione farmaceutica a rilascio controllato di moguisteina in sospensione liquida |
| JPH10504542A (ja) * | 1994-07-27 | 1998-05-06 | ジー．ディー．サール アンド カンパニー | 炎症処置用の置換チアゾール化合物 |
| US6274171B1 (en) * | 1996-03-25 | 2001-08-14 | American Home Products Corporation | Extended release formulation of venlafaxine hydrochloride |
| MY128323A (en) * | 1996-09-30 | 2007-01-31 | Otsuka Pharma Co Ltd | Thiazole derivatives for inhibition of cytokine production and of cell adhesion |
| WO2000006085A2 (en) | 1998-07-28 | 2000-02-10 | Smithkline Beecham Corporation | Compounds and methods |
| AU3126700A (en) * | 1998-12-18 | 2000-07-03 | Du Pont Pharmaceuticals Company | N-ureidoalkyl-piperidines as modulators of chemokine receptor activity |
| CN1376150A (zh) * | 1999-07-26 | 2002-10-23 | 盐野义制药株式会社 | 具有血栓形成素受体拮抗作用的药物组合物 |
| US7495018B2 (en) * | 2000-03-30 | 2009-02-24 | Takeda Pharmaceutical Company Limited | Substituted 1,3-thiazole compounds, their production and use |
| JP2002302488A (ja) * | 2000-03-30 | 2002-10-18 | Takeda Chem Ind Ltd | 置換１，３−チアゾール化合物、その製造法および用途 |
| JP4880816B2 (ja) | 2000-12-15 | 2012-02-22 | 株式会社ヤクルト本社 | 皮膚老化防止剤 |
| US8263657B2 (en) | 2000-12-18 | 2012-09-11 | Institute Of Medicinal Molecular Design, Inc. | Inhibitors against the production and release of inflammatory cytokines |
| CA2436739A1 (en) * | 2000-12-26 | 2002-07-04 | Takeda Chemical Industries, Ltd. | Combination agent |
| JP2002302458A (ja) | 2000-12-26 | 2002-10-18 | Takeda Chem Ind Ltd | 併用薬 |
| US7199124B2 (en) * | 2001-02-02 | 2007-04-03 | Takeda Pharmaceutical Company Limited | JNK inhibitor |
| JP2002302445A (ja) | 2001-02-02 | 2002-10-18 | Takeda Chem Ind Ltd | Ｊｎｋ阻害剤 |
| US20040242637A1 (en) | 2001-08-17 | 2004-12-02 | Hartman George D | Tyrosine kinase inhibitors |
| WO2003072102A1 (en) * | 2002-02-25 | 2003-09-04 | Eli Lilly And Company | Peroxisome proliferator activated receptor modulators |
| US20060100257A1 (en) * | 2002-06-05 | 2006-05-11 | Susumu Muto | Inhibitors against the activation of ap-1 and nfat |
| US20040110802A1 (en) | 2002-08-23 | 2004-06-10 | Atli Thorarensen | Antibacterial benzoic acid derivatives |
| US6737382B1 (en) * | 2002-10-23 | 2004-05-18 | Nippon Soda Co. Ltd. | Insecticidal aminothiazole derivatives |
| US7960369B2 (en) | 2002-11-08 | 2011-06-14 | Takeda Pharmaceutical Company Limited | Receptor function regulator |
| US7273866B2 (en) * | 2002-12-20 | 2007-09-25 | Bristol-Myers Squibb Company | 2-aryl thiazole derivatives as KCNQ modulators |
| US6987118B2 (en) * | 2003-05-21 | 2006-01-17 | Pfizer Inc. | Tetrahydroisoquinoline derivatives as PPAR-alpha activators |
| WO2005002673A1 (en) | 2003-07-03 | 2005-01-13 | Astex Therapeutics Limited | Raf kinase inhibitors |
| WO2005007151A1 (ja) | 2003-07-16 | 2005-01-27 | Institute Of Medicinal Molecular Design. Inc. | 皮膚色素沈着の治療剤 |
| EP1653968A4 (en) * | 2003-07-23 | 2006-09-06 | Synta Pharmaceuticals Corp | METHOD FOR MODULATING CALCIUMION RELIEF ACTIVATED CALCIUMION CHANNELS |
| 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 |
| EP1664006A2 (en) * | 2003-09-06 | 2006-06-07 | Vertex Pharmaceuticals Incorporated | Modulators of atp-binding cassette transporters |
| WO2005034957A1 (ja) * | 2003-10-08 | 2005-04-21 | Meiji Seika Kaisha, Ltd. | セフジトレン ピボキシルを含有する非晶性抗菌組成物 |
| WO2005044194A2 (en) | 2003-10-28 | 2005-05-19 | Pharmacia Corporation | TREATMENT OR PREVENTION OF NEOPLASIA BY USE OF AN Hsp90 INHIBITOR |
| ES2629414T3 (es) | 2003-12-26 | 2017-08-09 | Kyowa Hakko Kirin Co., Ltd. | Derivados de tiazol |
| EP1732900A4 (en) * | 2004-03-25 | 2007-12-12 | Synta Pharmaceuticals Corp | ACRYLONITRILE DERIVATIVES FOR THE TREATMENT OR PREVENTION OF INFLAMMATION AND IMMUNE DISORDERS |
| CA2589695A1 (en) | 2004-12-17 | 2006-06-22 | Eli Lilly And Company | Thiazolopyridinone derivates as mch receptor antagonists |
| JP2008542240A (ja) | 2005-05-24 | 2008-11-27 | ラボラトワール セローノ ソシエテ アノニム | チアゾール誘導体及びその使用 |
| CA2640090A1 (en) * | 2006-01-25 | 2007-08-02 | Synta Pharmaceuticals Corp. | Substituted aromatic compounds for inflammation and immune-related uses |
| JP2009528273A (ja) * | 2006-01-25 | 2009-08-06 | シンタ ファーマシューティカルズ コーポレーション | 炎症および免疫関連使用用の置換ビアリール化合物 |
| JP2009524683A (ja) * | 2006-01-25 | 2009-07-02 | シンタ ファーマシューティカルズ コーポレーション | 炎症および免疫関連用途のためのビニル−フェニル誘導体 |
| CA2639913A1 (en) * | 2006-01-25 | 2007-08-02 | Synta Pharmaceutical Corp. | Phenyl and pyridyl compounds for inflammation and immune-related uses |
-
2007
- 2007-01-25 EP EP07717039A patent/EP1983980A4/en not_active Withdrawn
- 2007-01-25 US US11/698,772 patent/US8455658B2/en not_active Expired - Fee Related
- 2007-01-25 TW TW096102794A patent/TWI444370B/zh not_active IP Right Cessation
- 2007-01-25 AU AU2007208225A patent/AU2007208225B2/en not_active Ceased
- 2007-01-25 WO PCT/US2007/002121 patent/WO2007087427A2/en not_active Ceased
- 2007-01-25 JP JP2008552423A patent/JP2009524677A/ja active Pending
- 2007-01-25 CA CA002639910A patent/CA2639910A1/en not_active Abandoned
-
2013
- 2013-05-16 US US13/895,590 patent/US20140135331A9/en not_active Abandoned
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2009524677A5 (enExample) | ||
| JP2008526866A5 (enExample) | ||
| JP2009525285A5 (enExample) | ||
| JP2006506340A5 (enExample) | ||
| DK2038265T3 (en) | Inhibitors of human protein tyrosine phosphatase and methods of use | |
| AU2007208225B2 (en) | Thiazole and thiadiazole compounds for inflammation and immune-related uses | |
| IL303196A (en) | Heteroaryl-substituted pyridines and methods of use | |
| JP2009524683A5 (enExample) | ||
| WO2012047966A4 (en) | Compositions and methods for treating ocular edema, neovascularization and related diseases | |
| RU2005129729A (ru) | Производные гетероарилкарбамоилбензола | |
| JP2008501673A5 (enExample) | ||
| JP2009513563A5 (enExample) | ||
| RU2011133833A (ru) | Способы лечения синдрома сосудистой утечки | |
| JP2019517455A5 (enExample) | ||
| JP2006077019A5 (enExample) | ||
| JP2007523142A5 (enExample) | ||
| HRP20110825T1 (hr) | Derivati aminotriazola kao alx agonisti | |
| JP2009529059A5 (enExample) | ||
| JP2013530240A5 (enExample) | ||
| JP2007519735A5 (enExample) | ||
| JP2009524678A5 (enExample) | ||
| RU2009102516A (ru) | Ингибиторы протеинтирозинфосфатазы человека и способы их использования | |
| US20130023542A1 (en) | Human protein tyrosine phosphatase inhibitors and methods of use | |
| JP2015517580A5 (enExample) | ||
| JP2010540462A5 (enExample) |