JP2011506417A5 - - Google Patents
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- JP2011506417A5 JP2011506417A5 JP2010537517A JP2010537517A JP2011506417A5 JP 2011506417 A5 JP2011506417 A5 JP 2011506417A5 JP 2010537517 A JP2010537517 A JP 2010537517A JP 2010537517 A JP2010537517 A JP 2010537517A JP 2011506417 A5 JP2011506417 A5 JP 2011506417A5
- Authority
- JP
- Japan
- Prior art keywords
- thiazol
- ethyl
- benzo
- urea
- 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.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims 13
- -1 1-ethyl-3- (5- (1- (2-morpholinoethyl) -1H-pyrazol-4-yl) benzo [d] thiazol-2-yl) urea 1- (5- (1H-pyrazol-3-yl) benzo [d] thiazol-2-yl) -3-ethylurea Chemical compound 0.000 claims 10
- 239000004202 carbamide Substances 0.000 claims 7
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 5
- 125000000623 heterocyclic group Chemical group 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 125000006413 ring segment Chemical group 0.000 claims 5
- 125000001424 substituent group Chemical group 0.000 claims 5
- 125000005605 benzo group Chemical group 0.000 claims 4
- 150000001204 N-oxides Chemical class 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000003386 piperidinyl group Chemical group 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical class O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical class C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical class OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
- OJEJUFGAKHQYSC-UHFFFAOYSA-N 1-[5-(3,4-dihydro-2h-pyrido[3,2-b][1,4]oxazin-7-yl)-1,3-benzothiazol-2-yl]-3-ethylurea Chemical compound N1CCOC2=CC(C=3C=C4N=C(SC4=CC=3)NC(=O)NCC)=CN=C21 OJEJUFGAKHQYSC-UHFFFAOYSA-N 0.000 claims 1
- FQDMAJAJQGUZKU-UHFFFAOYSA-N 1-[5-[1-(2-ethoxyethyl)-6-oxopyridin-3-yl]-1,3-benzothiazol-2-yl]-3-ethylurea Chemical compound C=1C=C2SC(NC(=O)NCC)=NC2=CC=1C=1C=CC(=O)N(CCOCC)C=1 FQDMAJAJQGUZKU-UHFFFAOYSA-N 0.000 claims 1
- AJEYDFVTRGYAPW-UHFFFAOYSA-N 1-[5-[1-[2-(dimethylamino)ethyl]-2-oxopyridin-4-yl]-6-fluoro-1,3-benzothiazol-2-yl]-3-ethylurea Chemical compound FC=1C=C2SC(NC(=O)NCC)=NC2=CC=1C=1C=CN(CCN(C)C)C(=O)C=1 AJEYDFVTRGYAPW-UHFFFAOYSA-N 0.000 claims 1
- FEZCMLSGFJEISW-UHFFFAOYSA-N 1-[5-[1-[3-(dimethylamino)propyl]-2-methyl-6-oxopyridin-4-yl]-6-fluoro-1,3-benzothiazol-2-yl]-3-ethylurea Chemical compound FC=1C=C2SC(NC(=O)NCC)=NC2=CC=1C=1C=C(C)N(CCCN(C)C)C(=O)C=1 FEZCMLSGFJEISW-UHFFFAOYSA-N 0.000 claims 1
- KDXZKBAHQKXWHE-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-6-fluoro-1,3-benzothiazol-5-yl]pyrimidin-2-yl]piperidine-3-carboxylic acid Chemical compound FC=1C=C2SC(NC(=O)NCC)=NC2=CC=1C(C=N1)=CN=C1N1CCCC(C(O)=O)C1 KDXZKBAHQKXWHE-UHFFFAOYSA-N 0.000 claims 1
- LCOMOVQMUQSDLR-UHFFFAOYSA-N 1-[5-[2-(ethylcarbamoylamino)-6-fluoro-1,3-benzothiazol-5-yl]pyrimidin-2-yl]piperidine-4-carboxylic acid Chemical compound FC=1C=C2SC(NC(=O)NCC)=NC2=CC=1C(C=N1)=CN=C1N1CCC(C(O)=O)CC1 LCOMOVQMUQSDLR-UHFFFAOYSA-N 0.000 claims 1
- SFMXVVTWITVKDF-UHFFFAOYSA-N 1-ethyl-3-(5-imidazo[1,2-a]pyridin-3-yl-1,3-benzothiazol-2-yl)urea Chemical compound C1=CC=CN2C(C=3C=C4N=C(SC4=CC=3)NC(=O)NCC)=CN=C21 SFMXVVTWITVKDF-UHFFFAOYSA-N 0.000 claims 1
- UVJOZSJQTBNSBC-UHFFFAOYSA-N 1-ethyl-3-(5-imidazo[1,2-a]pyridin-6-yl-1,3-benzothiazol-2-yl)urea Chemical compound C1=CC2=NC=CN2C=C1C1=CC=C(SC(NC(=O)NCC)=N2)C2=C1 UVJOZSJQTBNSBC-UHFFFAOYSA-N 0.000 claims 1
- BMIPFLDVVQUCKM-UHFFFAOYSA-N 1-ethyl-3-(5-isoquinolin-4-yl-1,3-benzothiazol-2-yl)urea Chemical compound C1=CC=C2C(C=3C=C4N=C(SC4=CC=3)NC(=O)NCC)=CN=CC2=C1 BMIPFLDVVQUCKM-UHFFFAOYSA-N 0.000 claims 1
- JUZOPGNAEFIKMI-UHFFFAOYSA-N 1-ethyl-3-(5-pyridin-3-yl-1,3-benzothiazol-2-yl)urea Chemical compound C=1C=C2SC(NC(=O)NCC)=NC2=CC=1C1=CC=CN=C1 JUZOPGNAEFIKMI-UHFFFAOYSA-N 0.000 claims 1
- SESBOEYJZCQDBQ-UHFFFAOYSA-N 1-ethyl-3-(6-fluoro-5-pyridin-3-yl-1,3-benzothiazol-2-yl)urea Chemical compound FC=1C=C2SC(NC(=O)NCC)=NC2=CC=1C1=CC=CN=C1 SESBOEYJZCQDBQ-UHFFFAOYSA-N 0.000 claims 1
- PDKCJJJNEIYSTR-UHFFFAOYSA-N 1-ethyl-3-(6-methoxy-5-pyridin-3-yl-1,3-benzothiazol-2-yl)urea Chemical compound COC=1C=C2SC(NC(=O)NCC)=NC2=CC=1C1=CC=CN=C1 PDKCJJJNEIYSTR-UHFFFAOYSA-N 0.000 claims 1
- LCRAXLYNKHWKRF-UHFFFAOYSA-N 1-ethyl-3-(6-methyl-5-pyridin-3-yl-1,3-benzothiazol-2-yl)urea Chemical compound CC=1C=C2SC(NC(=O)NCC)=NC2=CC=1C1=CC=CN=C1 LCRAXLYNKHWKRF-UHFFFAOYSA-N 0.000 claims 1
- OJIRJPXQGLKPLX-UHFFFAOYSA-N 1-ethyl-3-(6-pyridin-3-yl-[1,3]thiazolo[5,4-b]pyridin-2-yl)urea Chemical compound C=1N=C2SC(NC(=O)NCC)=NC2=CC=1C1=CC=CN=C1 OJIRJPXQGLKPLX-UHFFFAOYSA-N 0.000 claims 1
- ICIZQHAUBHCDNR-UHFFFAOYSA-N 1-ethyl-3-[5-(1-methyl-2-oxopyridin-4-yl)-1,3-benzothiazol-2-yl]urea Chemical compound C=1C=C2SC(NC(=O)NCC)=NC2=CC=1C=1C=CN(C)C(=O)C=1 ICIZQHAUBHCDNR-UHFFFAOYSA-N 0.000 claims 1
- KBYWLNLMISYCJJ-UHFFFAOYSA-N 1-ethyl-3-[5-(1-methylpyrazol-4-yl)-1,3-benzothiazol-2-yl]urea Chemical compound C=1C=C2SC(NC(=O)NCC)=NC2=CC=1C=1C=NN(C)C=1 KBYWLNLMISYCJJ-UHFFFAOYSA-N 0.000 claims 1
- DOZXCIUTWZEEFA-UHFFFAOYSA-N 1-ethyl-3-[5-(1h-pyrazol-4-yl)-1,3-benzothiazol-2-yl]urea Chemical compound C=1C=C2SC(NC(=O)NCC)=NC2=CC=1C=1C=NNC=1 DOZXCIUTWZEEFA-UHFFFAOYSA-N 0.000 claims 1
- IERZWUZDMPGDGZ-UHFFFAOYSA-N 1-ethyl-3-[5-(2-imidazol-1-ylpyrimidin-5-yl)-1,3-benzothiazol-2-yl]urea Chemical compound C=1C=C2SC(NC(=O)NCC)=NC2=CC=1C(C=N1)=CN=C1N1C=CN=C1 IERZWUZDMPGDGZ-UHFFFAOYSA-N 0.000 claims 1
- WDNOXIWYTZTYIJ-UHFFFAOYSA-N 1-ethyl-3-[5-(2-methoxy-1,3-thiazol-5-yl)-1,3-benzothiazol-2-yl]urea Chemical compound C=1C=C2SC(NC(=O)NCC)=NC2=CC=1C1=CN=C(OC)S1 WDNOXIWYTZTYIJ-UHFFFAOYSA-N 0.000 claims 1
- PJIDOBXNQXKBPI-UHFFFAOYSA-N 1-ethyl-3-[5-(2-methyl-6-oxopyran-4-yl)-1,3-benzothiazol-2-yl]urea Chemical compound C=1C=C2SC(NC(=O)NCC)=NC2=CC=1C=1C=C(C)OC(=O)C=1 PJIDOBXNQXKBPI-UHFFFAOYSA-N 0.000 claims 1
- KUAXFNLPHDBQLR-UHFFFAOYSA-N 1-ethyl-3-[5-(2-oxo-1h-pyridin-4-yl)-1,3-benzothiazol-2-yl]urea Chemical compound C=1C=C2SC(NC(=O)NCC)=NC2=CC=1C=1C=CNC(=O)C=1 KUAXFNLPHDBQLR-UHFFFAOYSA-N 0.000 claims 1
- DXWPTVSFXJWYGK-UHFFFAOYSA-N 1-ethyl-3-[5-(2-oxo-3h-1,3-thiazol-5-yl)-1,3-benzothiazol-2-yl]urea Chemical compound C=1C=C2SC(NC(=O)NCC)=NC2=CC=1C1=CN=C(O)S1 DXWPTVSFXJWYGK-UHFFFAOYSA-N 0.000 claims 1
- DVLHFOLCJLLICM-UHFFFAOYSA-N 1-ethyl-3-[5-(6-morpholin-4-ylpyridin-3-yl)-1,3-benzothiazol-2-yl]urea Chemical compound C=1C=C2SC(NC(=O)NCC)=NC2=CC=1C(C=N1)=CC=C1N1CCOCC1 DVLHFOLCJLLICM-UHFFFAOYSA-N 0.000 claims 1
- NPGBSWIIMNZWLH-UHFFFAOYSA-N 1-ethyl-3-[5-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-1,3-benzothiazol-2-yl]urea Chemical compound C1=CC2=NC=NN2C=C1C1=CC=C(SC(NC(=O)NCC)=N2)C2=C1 NPGBSWIIMNZWLH-UHFFFAOYSA-N 0.000 claims 1
- PJYWQWOTVHBJOX-UHFFFAOYSA-N 1-ethyl-3-[5-([1,2,4]triazolo[4,3-a]pyridin-6-yl)-1,3-benzothiazol-2-yl]urea Chemical compound C1=CC2=NN=CN2C=C1C1=CC=C(SC(NC(=O)NCC)=N2)C2=C1 PJYWQWOTVHBJOX-UHFFFAOYSA-N 0.000 claims 1
- ZCVPLGHYRBGXJA-UHFFFAOYSA-N 1-ethyl-3-[5-(tetrazolo[1,5-a]pyridin-6-yl)-1,3-benzothiazol-2-yl]urea Chemical compound C1=CC2=NN=NN2C=C1C1=CC=C(SC(NC(=O)NCC)=N2)C2=C1 ZCVPLGHYRBGXJA-UHFFFAOYSA-N 0.000 claims 1
- RTGPBFZARVRBQG-UHFFFAOYSA-N 1-ethyl-3-[5-[1-(2-hydroxyethyl)-2-methyl-6-oxopyridin-4-yl]-1,3-benzothiazol-2-yl]urea Chemical compound C=1C=C2SC(NC(=O)NCC)=NC2=CC=1C=1C=C(C)N(CCO)C(=O)C=1 RTGPBFZARVRBQG-UHFFFAOYSA-N 0.000 claims 1
- GTWCSQSSJHDDRA-UHFFFAOYSA-N 1-ethyl-3-[5-[1-(2-methoxyethyl)-2-methyl-6-oxopyridin-4-yl]-1,3-benzothiazol-2-yl]urea Chemical compound C=1C=C2SC(NC(=O)NCC)=NC2=CC=1C=1C=C(C)N(CCOC)C(=O)C=1 GTWCSQSSJHDDRA-UHFFFAOYSA-N 0.000 claims 1
- XOCHVIVRFUZYLK-UHFFFAOYSA-N 1-ethyl-3-[5-[2-(hydroxymethyl)-3-methylimidazol-4-yl]-1,3-benzothiazol-2-yl]urea Chemical compound C=1C=C2SC(NC(=O)NCC)=NC2=CC=1C1=CN=C(CO)N1C XOCHVIVRFUZYLK-UHFFFAOYSA-N 0.000 claims 1
- YQEOHQLMFVMQRC-UHFFFAOYSA-N 1-ethyl-3-[5-[2-methyl-1-[(6-methylpyridin-2-yl)methyl]-6-oxopyridin-4-yl]-1,3-benzothiazol-2-yl]urea Chemical compound C=1C=C2SC(NC(=O)NCC)=NC2=CC=1C(=CC1=O)C=C(C)N1CC1=CC=CC(C)=N1 YQEOHQLMFVMQRC-UHFFFAOYSA-N 0.000 claims 1
- VRJPCTKUYUJVMD-UHFFFAOYSA-N 1-ethyl-3-[5-[2-methyl-6-oxo-1-(pyridin-2-ylmethyl)pyridin-4-yl]-1,3-benzothiazol-2-yl]urea Chemical compound C=1C=C2SC(NC(=O)NCC)=NC2=CC=1C(=CC1=O)C=C(C)N1CC1=CC=CC=N1 VRJPCTKUYUJVMD-UHFFFAOYSA-N 0.000 claims 1
- YTOMRFZBGJFQDF-UHFFFAOYSA-N 1-ethyl-3-[5-[2-methyl-6-oxo-1-(pyridin-3-ylmethyl)pyridin-4-yl]-1,3-benzothiazol-2-yl]urea Chemical compound C=1C=C2SC(NC(=O)NCC)=NC2=CC=1C(=CC1=O)C=C(C)N1CC1=CC=CN=C1 YTOMRFZBGJFQDF-UHFFFAOYSA-N 0.000 claims 1
- AUMSVPWMSORTBR-UHFFFAOYSA-N 1-ethyl-3-[5-[5-(2-oxopyridin-1-yl)pyrazin-2-yl]-1,3-benzothiazol-2-yl]urea Chemical compound C=1C=C2SC(NC(=O)NCC)=NC2=CC=1C(N=C1)=CN=C1N1C=CC=CC1=O AUMSVPWMSORTBR-UHFFFAOYSA-N 0.000 claims 1
- ICTNNBOJDBSQTE-UHFFFAOYSA-N 1-ethyl-3-[5-[6-(2-methyltetrazol-5-yl)pyridin-3-yl]-1,3-benzothiazol-2-yl]urea Chemical compound C=1C=C2SC(NC(=O)NCC)=NC2=CC=1C(C=N1)=CC=C1C=1N=NN(C)N=1 ICTNNBOJDBSQTE-UHFFFAOYSA-N 0.000 claims 1
- CPPMKAZKQCKFRT-UHFFFAOYSA-N 1-ethyl-3-[5-[6-(hydroxymethyl)pyridin-3-yl]-1,3-benzothiazol-2-yl]urea Chemical compound C=1C=C2SC(NC(=O)NCC)=NC2=CC=1C1=CC=C(CO)N=C1 CPPMKAZKQCKFRT-UHFFFAOYSA-N 0.000 claims 1
- XRRFWZVFIZUJQM-UHFFFAOYSA-N 1-ethyl-3-[6-(2-methyl-6-oxopyran-4-yl)-[1,3]thiazolo[5,4-b]pyridin-2-yl]urea Chemical compound C=1N=C2SC(NC(=O)NCC)=NC2=CC=1C=1C=C(C)OC(=O)C=1 XRRFWZVFIZUJQM-UHFFFAOYSA-N 0.000 claims 1
- VIIUMBFCEKKFAH-UHFFFAOYSA-N 1-ethyl-3-[6-fluoro-5-(1,3-thiazol-5-yl)-1,3-benzothiazol-2-yl]urea Chemical compound FC=1C=C2SC(NC(=O)NCC)=NC2=CC=1C1=CN=CS1 VIIUMBFCEKKFAH-UHFFFAOYSA-N 0.000 claims 1
- SFAIZLCVDNVGGJ-UHFFFAOYSA-N 1-ethyl-3-[6-fluoro-5-(1-methyl-2-oxopyridin-4-yl)-1,3-benzothiazol-2-yl]urea Chemical compound FC=1C=C2SC(NC(=O)NCC)=NC2=CC=1C=1C=CN(C)C(=O)C=1 SFAIZLCVDNVGGJ-UHFFFAOYSA-N 0.000 claims 1
- LSZDLXKNEREMBW-UHFFFAOYSA-N 1-ethyl-3-[6-fluoro-5-(1h-pyrrolo[2,3-b]pyridin-3-yl)-1,3-benzothiazol-2-yl]urea Chemical compound C1=CC=C2C(C=3C=C4N=C(SC4=CC=3F)NC(=O)NCC)=CNC2=N1 LSZDLXKNEREMBW-UHFFFAOYSA-N 0.000 claims 1
- WQCUFLPVZRAJKU-UHFFFAOYSA-N 1-ethyl-3-[6-fluoro-5-(2-methylsulfonylpyrimidin-5-yl)-1,3-benzothiazol-2-yl]urea Chemical compound FC=1C=C2SC(NC(=O)NCC)=NC2=CC=1C1=CN=C(S(C)(=O)=O)N=C1 WQCUFLPVZRAJKU-UHFFFAOYSA-N 0.000 claims 1
- SZTVSKREVPNNNI-UHFFFAOYSA-N 1-ethyl-3-[6-fluoro-5-(2-oxo-1-pyrrolidin-3-ylpyridin-4-yl)-1,3-benzothiazol-2-yl]urea Chemical compound FC=1C=C2SC(NC(=O)NCC)=NC2=CC=1C(=CC1=O)C=CN1C1CCNC1 SZTVSKREVPNNNI-UHFFFAOYSA-N 0.000 claims 1
- HYXWDZXHFJPHJW-UHFFFAOYSA-N 1-ethyl-3-[6-fluoro-5-(2-piperazin-1-ylpyrimidin-5-yl)-1,3-benzothiazol-2-yl]urea;hydrochloride Chemical compound Cl.FC=1C=C2SC(NC(=O)NCC)=NC2=CC=1C(C=N1)=CN=C1N1CCNCC1 HYXWDZXHFJPHJW-UHFFFAOYSA-N 0.000 claims 1
- CDRBZIWHZFQOGA-UHFFFAOYSA-N 1-ethyl-3-[6-fluoro-5-(4-methoxypyridin-2-yl)-1,3-benzothiazol-2-yl]urea Chemical compound FC=1C=C2SC(NC(=O)NCC)=NC2=CC=1C1=CC(OC)=CC=N1 CDRBZIWHZFQOGA-UHFFFAOYSA-N 0.000 claims 1
- RWBYPNPZWLOZBK-UHFFFAOYSA-N 1-ethyl-3-[6-fluoro-5-(5-hydroxypyridin-3-yl)-1,3-benzothiazol-2-yl]urea Chemical compound FC=1C=C2SC(NC(=O)NCC)=NC2=CC=1C1=CN=CC(O)=C1 RWBYPNPZWLOZBK-UHFFFAOYSA-N 0.000 claims 1
- YXDKIVLKMWAVNA-UHFFFAOYSA-N 1-ethyl-3-[6-fluoro-5-(5-methoxypyridin-3-yl)-1,3-benzothiazol-2-yl]urea Chemical compound FC=1C=C2SC(NC(=O)NCC)=NC2=CC=1C1=CN=CC(OC)=C1 YXDKIVLKMWAVNA-UHFFFAOYSA-N 0.000 claims 1
- WBXQNQAKOAPQIS-UHFFFAOYSA-N 1-ethyl-3-[6-fluoro-5-[1-(2-morpholin-4-ylethyl)-2-oxopyridin-4-yl]-1,3-benzothiazol-2-yl]urea Chemical compound FC=1C=C2SC(NC(=O)NCC)=NC2=CC=1C(=CC1=O)C=CN1CCN1CCOCC1 WBXQNQAKOAPQIS-UHFFFAOYSA-N 0.000 claims 1
- CJEOICZZUAJJTM-UHFFFAOYSA-N 1-ethyl-3-[6-fluoro-5-[2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]-1,3-benzothiazol-2-yl]urea Chemical compound FC=1C=C2SC(NC(=O)NCC)=NC2=CC=1C(C=N1)=CN=C1N1CCN(C)CC1 CJEOICZZUAJJTM-UHFFFAOYSA-N 0.000 claims 1
- GKZOCNOYDIKRMN-UHFFFAOYSA-N 1-ethyl-3-[6-fluoro-5-[2-[4-(2-hydroxyethyl)piperazin-1-yl]pyrimidin-5-yl]-1,3-benzothiazol-2-yl]urea Chemical compound FC=1C=C2SC(NC(=O)NCC)=NC2=CC=1C(C=N1)=CN=C1N1CCN(CCO)CC1 GKZOCNOYDIKRMN-UHFFFAOYSA-N 0.000 claims 1
- IGPLFESYPJKUIT-UHFFFAOYSA-N 1-ethyl-3-[6-fluoro-5-[2-methyl-1-[(1-methylimidazol-4-yl)methyl]-6-oxopyridin-4-yl]-1,3-benzothiazol-2-yl]urea Chemical compound FC=1C=C2SC(NC(=O)NCC)=NC2=CC=1C(=CC1=O)C=C(C)N1CC1=CN(C)C=N1 IGPLFESYPJKUIT-UHFFFAOYSA-N 0.000 claims 1
- ZWMXKXNCZAXWND-UHFFFAOYSA-N 1-ethyl-3-[6-fluoro-5-[2-methyl-1-[1-(6-methylpyridin-3-yl)ethyl]-6-oxopyridin-4-yl]-1,3-benzothiazol-2-yl]urea Chemical compound FC=1C=C2SC(NC(=O)NCC)=NC2=CC=1C(=CC1=O)C=C(C)N1C(C)C1=CC=C(C)N=C1 ZWMXKXNCZAXWND-UHFFFAOYSA-N 0.000 claims 1
- COWUIVSDMZNIOO-UHFFFAOYSA-N 1-ethyl-3-[6-fluoro-5-[6-(hydroxymethyl)pyridin-3-yl]-1,3-benzothiazol-2-yl]urea Chemical compound FC=1C=C2SC(NC(=O)NCC)=NC2=CC=1C1=CC=C(CO)N=C1 COWUIVSDMZNIOO-UHFFFAOYSA-N 0.000 claims 1
- RMMFLZYVRZYEJH-UHFFFAOYSA-N 1-ethyl-3-[6-fluoro-5-[6-(morpholin-4-ylmethyl)pyridin-3-yl]-1,3-benzothiazol-2-yl]urea Chemical compound FC=1C=C2SC(NC(=O)NCC)=NC2=CC=1C(C=N1)=CC=C1CN1CCOCC1 RMMFLZYVRZYEJH-UHFFFAOYSA-N 0.000 claims 1
- CCKSWMJYOYEDBJ-UHFFFAOYSA-N 1-ethyl-3-[6-fluoro-5-[6-[(Z)-N'-hydroxycarbamimidoyl]pyridin-3-yl]-1,3-benzothiazol-2-yl]urea Chemical compound FC=1C=C2SC(NC(=O)NCC)=NC2=CC=1C1=CC=C(C(N)=NO)N=C1 CCKSWMJYOYEDBJ-UHFFFAOYSA-N 0.000 claims 1
- CBQNUCICVBMAEN-UHFFFAOYSA-N 1-ethyl-3-[6-methoxy-5-(1-methyl-2-oxopyridin-4-yl)-1,3-benzothiazol-2-yl]urea Chemical compound COC=1C=C2SC(NC(=O)NCC)=NC2=CC=1C=1C=CN(C)C(=O)C=1 CBQNUCICVBMAEN-UHFFFAOYSA-N 0.000 claims 1
- JWQRMITVLGIGCV-UHFFFAOYSA-N 2-[5-[2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyridin-2-yl]-n-methylacetamide Chemical compound C=1C=C2SC(NC(=O)NCC)=NC2=CC=1C1=CC=C(CC(=O)NC)N=C1 JWQRMITVLGIGCV-UHFFFAOYSA-N 0.000 claims 1
- JFYRHAFXWNLJHD-UHFFFAOYSA-N 2-[5-[2-(ethylcarbamoylamino)-6-fluoro-1,3-benzothiazol-5-yl]pyridin-2-yl]-n-methylacetamide Chemical compound FC=1C=C2SC(NC(=O)NCC)=NC2=CC=1C1=CC=C(CC(=O)NC)N=C1 JFYRHAFXWNLJHD-UHFFFAOYSA-N 0.000 claims 1
- ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical class O=C1C=CC=CO1 ZPSJGADGUYYRKE-UHFFFAOYSA-N 0.000 claims 1
- 208000035143 Bacterial infection Diseases 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Chemical class C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical class C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
- 125000004450 alkenylene group Chemical group 0.000 claims 1
- 125000004419 alkynylene group Chemical group 0.000 claims 1
- 239000003242 anti bacterial agent Substances 0.000 claims 1
- 208000022362 bacterial infectious disease Diseases 0.000 claims 1
- 125000002527 bicyclic carbocyclic group Chemical group 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- LEMCBKVVDHBCFN-UHFFFAOYSA-N ethyl 7-[2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]-1-methyl-4-oxoquinoline-3-carboxylate Chemical compound CN1C=C(C(=O)OCC)C(=O)C=2C1=CC(C=1C=C3N=C(SC3=CC=1)NC(=O)NCC)=CC=2 LEMCBKVVDHBCFN-UHFFFAOYSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000001620 monocyclic carbocycle group Chemical group 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- RCWOKJMBZJIAFP-UHFFFAOYSA-N n-[5-[2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyridin-2-yl]acetamide Chemical compound C=1C=C2SC(NC(=O)NCC)=NC2=CC=1C1=CC=C(NC(C)=O)N=C1 RCWOKJMBZJIAFP-UHFFFAOYSA-N 0.000 claims 1
- NEDNPDQFFWXYMP-UHFFFAOYSA-N n-[5-[2-(ethylcarbamoylamino)-6-fluoro-1,3-benzothiazol-5-yl]pyridin-2-yl]acetamide Chemical compound FC=1C=C2SC(NC(=O)NCC)=NC2=CC=1C1=CC=C(NC(C)=O)N=C1 NEDNPDQFFWXYMP-UHFFFAOYSA-N 0.000 claims 1
- FUBZAHXLDYKNDC-UHFFFAOYSA-N n-[5-[2-(ethylcarbamoylamino)-[1,3]thiazolo[5,4-b]pyridin-6-yl]pyridin-2-yl]acetamide Chemical compound C=1N=C2SC(NC(=O)NCC)=NC2=CC=1C1=CC=C(NC(C)=O)N=C1 FUBZAHXLDYKNDC-UHFFFAOYSA-N 0.000 claims 1
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 230000000069 prophylactic effect Effects 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 150000003222 pyridines Chemical class 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- NYCVCXMSZNOGDH-UHFFFAOYSA-N pyrrolidine-1-carboxylic acid Chemical compound OC(=O)N1CCCC1 NYCVCXMSZNOGDH-UHFFFAOYSA-N 0.000 claims 1
- 125000003831 tetrazolyl group Chemical group 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- 150000003568 thioethers Chemical class 0.000 claims 1
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| CA2725689A1 (en) * | 2008-06-04 | 2009-12-10 | Astrazeneca Ab | Thiazolo [5,4-b] pyridine and oxazolo [5,4-b] pyridine derivatives as antibacterial agents |
| WO2009156966A1 (en) * | 2008-06-25 | 2009-12-30 | Ranbaxy Laboratories Limited | Benzothiazoles and aza-analogues thereof use as antibacterial agents |
| CN102712647B (zh) * | 2009-10-16 | 2018-04-24 | 梅琳塔治疗公司 | 抗微生物化合物和其制备和使用方法 |
| JP2013508299A (ja) | 2009-10-16 | 2013-03-07 | リブ−エックス ファーマシューティカルズ，インコーポレイテッド | 抗微生物性化合物および抗微生物性化合物の製造方法および使用方法 |
| PH12012500734A1 (en) | 2009-10-16 | 2012-11-26 | Melinta Therapeutics Inc | Antimicrobial compounds and methods of making and using the same |
| KR20130012072A (ko) * | 2010-03-31 | 2013-01-31 | 액테리온 파마슈티칼 리미티드 | 항박테리아성 이소퀴놀린-３-일우레아 유도체 |
| WO2011149822A1 (en) | 2010-05-26 | 2011-12-01 | Boehringer Ingelheim International Gmbh | 2-oxo-1,2-dihydropyridin-4-ylboronic acid derivatives |
| WO2012045124A1 (en) * | 2010-10-08 | 2012-04-12 | Biota Europe Ltd | Bacteria topoisomerase ii inhibiting 2-ethylcarbamoylamino-1, 3-benzothiazol-5-yls |
| TWI546298B (zh) | 2011-01-14 | 2016-08-21 | 維泰克斯製藥公司 | 旋轉酶及拓樸異構酶ｉｖ抑制劑 |
| CA2824403C (en) | 2011-01-14 | 2019-09-24 | Vertex Pharmaceuticals Incorporated | Solid forms of gyrase inhibitor (r)-1-ethyl-3-[6-fluoro-5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-7-(tetrahydrofuran-2-yl)-1h-benzimidazol-2-yl]urea |
| ES2526902T3 (es) | 2011-01-14 | 2015-01-16 | Vertex Pharmaceuticals Incorporated | Procesos de producción de inhibidores de la girasa y topoisomerasa IV |
| BR112013017977A2 (pt) | 2011-01-14 | 2019-09-24 | Vertex Pharma | formas sólidas de inibidor de girase (r) 1-etil-3-[5-[2-{1-hidroxi-1-metil-etil}pirimidin-5-il]-7-(tetrai-drofuran-2-il)-1h-benzimidazol-2-il]ureia |
| EP2691399B1 (en) * | 2011-03-28 | 2016-07-13 | F.Hoffmann-La Roche Ag | Thiazolopyrimidine compounds |
| AR088729A1 (es) | 2011-03-29 | 2014-07-02 | Actelion Pharmaceuticals Ltd | Derivados de 3-ureidoisoquinolin-8-ilo y una composicion farmaceutica |
| CN103958514B (zh) | 2011-04-15 | 2018-07-03 | 梅琳塔治疗公司 | 抗微生物化合物及制备和使用所述化合物的方法 |
| EP2721026B1 (en) | 2011-06-20 | 2016-03-02 | Vertex Pharmaceuticals Incorporated | Phosphate esters of gyrase and topoisomerase inhibitors |
| US9822108B2 (en) | 2012-01-13 | 2017-11-21 | Rutgers, The State University Of New Jersey | Antimicrobial agents |
| CA2868002C (en) | 2012-03-21 | 2021-07-13 | Rutgers, The State University Of New Jersey | Antimicrobial agents |
| EP2828257B1 (en) * | 2012-03-22 | 2017-07-26 | Biota Europe Ltd | Antibacterial compounds |
| NZ703020A (en) * | 2012-07-10 | 2017-08-25 | Bayer Pharma AG | Method for preparing substituted triazolopyridines |
| US9572809B2 (en) | 2012-07-18 | 2017-02-21 | Spero Trinem, Inc. | Combination therapy to treat Mycobacterium diseases |
| JP6186434B2 (ja) * | 2012-07-18 | 2017-08-23 | サンシャイン・レイク・ファーマ・カンパニー・リミテッドＳｕｎｓｈｉｎｅ Ｌａｋｅ Ｐｈａｒｍａ Ｃｏ．，Ｌｔｄ． | 窒素複素環誘導体及びその医薬品への応用 |
| US9018216B2 (en) | 2012-07-18 | 2015-04-28 | Vertex Pharmaceuticals Incorporated | Solid forms of (R)-2-(5-(2-(3-ethylureido)-6-fluoro-7-(tetrahydrofuran-2-yl)-1H-benzo[d]imidazol-5-yl)pyrimidin-2-yl)propan-2-yl dihydrogen phosphate and salts thereof |
| BR112015014145B1 (pt) | 2012-12-21 | 2020-12-29 | Janssen Sciences Ireland Uc | compostos antibacterianos, composição farmacêutica, seus processos de preparação e combinação |
| EP3038623A4 (en) | 2013-09-09 | 2017-04-19 | Melinta Therapeutics, Inc. | Antimicrobial compounds and methods of making and using the same |
| MX2016002975A (es) | 2013-09-09 | 2016-10-21 | Melinta Therapeutics Inc | Compuestos antimicrobianos y métodos de fabricación y utilización de los mismos. |
| US9458150B2 (en) | 2013-11-08 | 2016-10-04 | Rutgers, The State University Of New Jersey | Antimicrobial agents |
| MX2016010057A (es) | 2014-02-03 | 2017-04-27 | Spero Gyrase Inc | Compuestos antibacterianos. |
| CN105367547B (zh) * | 2014-08-19 | 2019-04-23 | 北京桦冠生物技术有限公司 | 一种噁唑啉酮抗生素的新合成工艺 |
| AR102215A1 (es) * | 2014-10-10 | 2017-02-15 | Glaxosmithkline Ip Dev Ltd | Compuesto de pirazol-4-carboxamida, composición farmacéutica que lo comprende y su uso para la fabricación de un medicamento |
| BR112017019349A2 (pt) | 2015-03-11 | 2018-06-05 | Melinta Therapeutics Inc | compostos antimicrobianos e métodos de fabricação e uso dos mesmos |
| US10513528B2 (en) | 2016-02-25 | 2019-12-24 | Taxis Pharmaceuticals, Inc. | Synthetic processes and intermediates |
| CN109069492B (zh) | 2016-04-08 | 2021-12-10 | 快尔生物技术公司 | 环稠和的噻唑啉2-吡啶酮、其制备方法及其在治疗和/或预防结核中的用途 |
| US11098047B2 (en) | 2016-05-06 | 2021-08-24 | BioVersys AG | Antimicrobials and methods of making and using same |
| CN110446699A (zh) | 2017-03-24 | 2019-11-12 | 大正制药株式会社 | 2（1h）-喹啉酮衍生物 |
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| CN107325093B (zh) * | 2017-07-09 | 2020-06-05 | 西南科技大学 | 具抗菌活性的硫脲类化合物合成及应用 |
| PT3589632T (pt) | 2018-02-23 | 2020-12-09 | Fraunhofer Ges Forschung | Novos inibidores de glutaminil ciclases bacterianas para utilização no tratamento de doenças periodontais e relacionadas |
| CN119874700A (zh) | 2019-09-13 | 2025-04-25 | 林伯士萨顿公司 | Hpk1拮抗剂和其用途 |
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| CH505543A (de) | 1968-11-01 | 1971-04-15 | Ciba Geigy Ag | Schädlingsbekämpfungsmittel |
| US4028374A (en) * | 1975-11-03 | 1977-06-07 | Morton-Norwich Products, Inc. | Antibacterial thiocyanatobenzothiazoles |
| JPS57149280A (en) * | 1981-03-10 | 1982-09-14 | Kyowa Hakko Kogyo Co Ltd | Amino acid derivative and its preparation |
| JP2003521543A (ja) | 2000-02-07 | 2003-07-15 | アボット ゲーエムベーハー ウント カンパニー カーゲー | ２−ベンゾチアゾリル尿素誘導体およびそのプロテインキナーゼ阻害剤としての使用 |
| CZ2003182A3 (cs) | 2000-06-21 | 2003-06-18 | F. Hoffmann-La Roche Ag | Deriváty benzothiazolu |
| BR0116216A (pt) * | 2000-12-15 | 2004-08-17 | Vertex Pharma | Inibidores de girase e seus usos |
| CA2489128C (en) | 2002-06-13 | 2012-01-03 | Vertex Pharmaceuticals Incorporated | 2-ureido-6-heteroaryl-3h-benzoimidazole-4-carboxylic acid derivatives and related compounds as gyrase and/or topoisomerase iv inhibitors for the treatment of bacterial infections |
| AR042956A1 (es) | 2003-01-31 | 2005-07-13 | Vertex Pharma | Inhibidores de girasa y usos de los mismos |
| US20050130974A1 (en) | 2003-10-17 | 2005-06-16 | Rigel Pharmaceuticals, Inc. | Benzothiazole compositions and their use as ubiquitin ligase inhibitors |
| AU2005280908A1 (en) * | 2004-09-09 | 2006-03-16 | Chugai Seiyaku Kabushiki Kaisha | Novel imidazolidine derivative and use thereof |
| GB0612428D0 (en) | 2006-06-22 | 2006-08-02 | Prolysis Ltd | Antibacterial agents |
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