JP5539898B2 - 抗菌活性縮合チアゾール - Google Patents
抗菌活性縮合チアゾール Download PDFInfo
- Publication number
- JP5539898B2 JP5539898B2 JP2010537517A JP2010537517A JP5539898B2 JP 5539898 B2 JP5539898 B2 JP 5539898B2 JP 2010537517 A JP2010537517 A JP 2010537517A JP 2010537517 A JP2010537517 A JP 2010537517A JP 5539898 B2 JP5539898 B2 JP 5539898B2
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- JP
- Japan
- Prior art keywords
- ethyl
- thiazol
- mmol
- urea
- benzo
- 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.)
- Expired - Fee Related
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- 230000000844 anti-bacterial effect Effects 0.000 title description 12
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 89
- -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 description 58
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 32
- 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 description 23
- 239000004202 carbamide Substances 0.000 claims description 22
- 125000000623 heterocyclic group Chemical group 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- 125000006413 ring segment Chemical group 0.000 claims description 19
- 125000001424 substituent group Chemical group 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 12
- 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 description 9
- 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 description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000005605 benzo group Chemical group 0.000 claims description 9
- 125000003386 piperidinyl group Chemical group 0.000 claims description 9
- 125000004076 pyridyl group Chemical group 0.000 claims description 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
- 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 description 8
- 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 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
- 208000035143 Bacterial infection Diseases 0.000 claims description 6
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 6
- 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 description 5
- 125000002757 morpholinyl group Chemical group 0.000 claims description 5
- 125000004193 piperazinyl group Chemical group 0.000 claims description 5
- DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 claims description 5
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 5
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims description 5
- 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 description 4
- 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 description 4
- DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical class O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 claims description 4
- 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 description 4
- 150000001204 N-oxides Chemical class 0.000 claims description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical class C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 4
- 125000001620 monocyclic carbocycle group Chemical group 0.000 claims description 4
- 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 description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical class OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- NYCVCXMSZNOGDH-UHFFFAOYSA-N pyrrolidine-1-carboxylic acid Chemical compound OC(=O)N1CCCC1 NYCVCXMSZNOGDH-UHFFFAOYSA-N 0.000 claims description 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000002527 bicyclic carbocyclic group Chemical group 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 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 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
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- UKCBGXCNXOKVTF-UHFFFAOYSA-N tert-butyl 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C1=NC=C(Br)C=N1 UKCBGXCNXOKVTF-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/428—Thiazoles condensed with carbocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D277/82—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
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| PCT/GB2008/004114 WO2009074812A1 (en) | 2007-12-13 | 2008-12-12 | Antibacterial condensed thiazoles |
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| WO (1) | WO2009074812A1 (enExample) |
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| KR20110031419A (ko) * | 2008-06-04 | 2011-03-28 | 아스트라제네카 아베 | 항박테리아제로서의 티아졸로[5,4b]피리딘 및 옥사졸로[5,4b]피리딘 유도체 |
| US20110166088A1 (en) * | 2008-06-25 | 2011-07-07 | Ranbaxy Laboratories Limited | Benzothiazoles and aza-analogues thereof use as antibacterial agents |
| CN102725274A (zh) | 2009-10-16 | 2012-10-10 | Rib-X制药公司 | 抗微生物化合物和其制备和使用方法 |
| KR20190044136A (ko) * | 2009-10-16 | 2019-04-29 | 멜린타 서브시디어리 코프. | 항미생물성 화합물 및 이의 제조 방법 및 사용 방법 |
| NZ599289A (en) | 2009-10-16 | 2014-11-28 | Melinta Therapeutics Inc | Antimicrobial compounds and methods of making and using the same |
| WO2011121555A1 (en) | 2010-03-31 | 2011-10-06 | Actelion Pharmaceuticals Ltd | Antibacterial isoquinolin-3-ylurea derivatives |
| WO2011149822A1 (en) | 2010-05-26 | 2011-12-01 | Boehringer Ingelheim International Gmbh | 2-oxo-1,2-dihydropyridin-4-ylboronic acid derivatives |
| EP2625178A4 (en) * | 2010-10-08 | 2014-04-30 | Biota Europe Ltd | BACTERIA TOPOISOMERASE II FOR INHIBITING 2-ETHYL CARBAMOYLAMINE-1,3-BENZOTHIAZOL-5-YLENE |
| SG191946A1 (en) | 2011-01-14 | 2013-08-30 | Vertex Pharma | Pyrimidine gyrase and topoisomerase iv inhibitors |
| WO2012097273A1 (en) | 2011-01-14 | 2012-07-19 | 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 |
| AU2012205420B2 (en) | 2011-01-14 | 2016-12-08 | Spero Therapeutics, Inc. | Process of making gyrase and topoisomerase IV inhibitors |
| RU2013137753A (ru) | 2011-01-14 | 2015-02-20 | Вертекс Фармасьютикалз Инкорпорейтед | Твердые формы ингибитора гиразы (r)-1-этил-3-[5-[2-(1-гидрокси-1-метилэтил)пиримидин-5-ил]-7-(тетрагидрофуран-2-ил)-1н-бензимидазол-2-ил]мочевины |
| CA2828824A1 (en) * | 2011-03-28 | 2012-10-04 | 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 |
| EA201391536A1 (ru) | 2011-04-15 | 2014-08-29 | Мелинта Терапьютикс, Инк. | Противомикробные соединения и способы их получения и применения |
| CN103702994B (zh) | 2011-06-20 | 2016-03-23 | 沃泰克斯药物股份有限公司 | 旋转酶和拓扑异构酶抑制剂的磷酸酯 |
| US9822108B2 (en) | 2012-01-13 | 2017-11-21 | Rutgers, The State University Of New Jersey | Antimicrobial agents |
| AU2013235038A1 (en) | 2012-03-21 | 2014-10-09 | Malvika Kaul | Antimicrobial agents |
| CN104302645A (zh) * | 2012-03-22 | 2015-01-21 | 生物区欧洲有限公司 | 抗菌化合物 |
| CN104603136B (zh) * | 2012-07-10 | 2017-06-27 | 拜耳医药股份有限公司 | 制备取代的三唑并吡啶的方法 |
| 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 |
| US9572809B2 (en) | 2012-07-18 | 2017-02-21 | Spero Trinem, Inc. | Combination therapy to treat Mycobacterium diseases |
| KR102057877B1 (ko) | 2012-07-18 | 2019-12-20 | 노스 앤드 사우스 브라더 파마시 인베스트먼트 컴파니 리미티드 | 질소함유 헤테로고리 유도체 및 그의 약물에서의 용도 |
| UA117672C2 (uk) | 2012-12-21 | 2018-09-10 | ЯНССЕН САЙЄНСІЗ АЙРЛЕНД ЮСі | Антибактеріальні сполуки |
| EP3038623A4 (en) | 2013-09-09 | 2017-04-19 | Melinta Therapeutics, Inc. | Antimicrobial compounds and methods of making and using the same |
| SG10201801956SA (en) | 2013-09-09 | 2018-04-27 | Melinta Therapeutics Inc | Antimicrobial compounds and methods of making and using the same |
| US9458150B2 (en) | 2013-11-08 | 2016-10-04 | Rutgers, The State University Of New Jersey | Antimicrobial agents |
| SG11201606332PA (en) | 2014-02-03 | 2016-09-29 | Spero Gyrase Inc | Antibacterial combinations comprising polymyxin |
| 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 |
| JP2018507881A (ja) | 2015-03-11 | 2018-03-22 | メリンタ セラピューティクス,インコーポレイテッド | 抗微生物化合物ならびにこれらを作製および使用する方法 |
| 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 |
| CA3023317A1 (en) | 2016-05-06 | 2017-11-09 | Melinta Therapeutics, Inc. | Antimicrobials and methods of making and using same |
| WO2018174288A1 (ja) | 2017-03-24 | 2018-09-27 | 大正製薬株式会社 | 2(1h)-キノリノン誘導体 |
| US10774093B2 (en) | 2017-03-30 | 2020-09-15 | Taxis Pharmaceuticals, Inc. | Synthetic processes and synthetic intermediates |
| 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 |
| AU2019223215B2 (en) | 2018-02-23 | 2022-09-15 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Novel inhibitors of bacterial glutaminyl cyclases for use in the treatment of periodontal and related diseases |
| BR112022004451A2 (pt) | 2019-09-13 | 2022-06-21 | Nimbus Saturn Inc | Antagonistas de hpk1 e usos dos mesmos |
| CN117120090A (zh) | 2021-02-12 | 2023-11-24 | 林伯士萨顿公司 | Hpk1拮抗剂和其用途 |
| JP2024509192A (ja) | 2021-03-05 | 2024-02-29 | ニンバス サターン, インコーポレイテッド | Hpk1アンタゴニスト及びその使用 |
| JP2024513011A (ja) | 2021-03-29 | 2024-03-21 | ニンバス サターン, インコーポレイテッド | Hpk1アンタゴニスト及びその使用 |
| WO2025202955A1 (en) | 2024-03-28 | 2025-10-02 | Pi Industries Ltd. | Fused bicyclic compounds and their use as pest control agents |
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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 |
| SK12712002A3 (sk) | 2000-02-07 | 2003-02-04 | Abbott Gmbh & Co. Kg | Deriváty 2-benzotiazolylmočoviny a ich použitie ako inhibítorov proteínkináz |
| CA2413086C (en) | 2000-06-21 | 2011-06-28 | Alexander Alanine | Benzothiazole derivatives |
| IL156031A0 (en) * | 2000-12-15 | 2003-12-23 | Vertex Pharma | Fused heterocyclic derivatives and pharmaceutical compositions containing the same |
| 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 |
| EP1680431A1 (en) | 2003-10-17 | 2006-07-19 | Rigel Pharmaceuticals, Inc. | Benzothiazole and thiazole'5,5-b!pyridine compositions and their use as ubiquitin ligase inhibitors |
| TW200621723A (en) * | 2004-09-09 | 2006-07-01 | Chugai Pharmaceutical Co Ltd | Novel imidazolidine derivative and use thereof |
| GB0612428D0 (en) | 2006-06-22 | 2006-08-02 | Prolysis Ltd | Antibacterial agents |
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2007
- 2007-12-13 GB GBGB0724342.1A patent/GB0724342D0/en not_active Ceased
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2008
- 2008-12-12 NZ NZ586508A patent/NZ586508A/en not_active IP Right Cessation
- 2008-12-12 EP EP20080859786 patent/EP2231653B1/en not_active Not-in-force
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- 2008-12-12 BR BRPI0820656-2A patent/BRPI0820656A2/pt not_active IP Right Cessation
- 2008-12-12 CN CN200880126437.2A patent/CN102015700B/zh not_active Expired - Fee Related
- 2008-12-12 WO PCT/GB2008/004114 patent/WO2009074812A1/en not_active Ceased
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- 2008-12-12 CA CA 2709021 patent/CA2709021A1/en not_active Abandoned
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Also Published As
| Publication number | Publication date |
|---|---|
| US8299065B2 (en) | 2012-10-30 |
| EA201000993A1 (ru) | 2011-02-28 |
| KR20100105847A (ko) | 2010-09-30 |
| US20100305067A1 (en) | 2010-12-02 |
| NZ586508A (en) | 2012-05-25 |
| AU2008334427B2 (en) | 2014-06-19 |
| CA2709021A1 (en) | 2009-06-18 |
| CN102015700A (zh) | 2011-04-13 |
| EP2231653B1 (en) | 2013-04-03 |
| JP2011506417A (ja) | 2011-03-03 |
| EP2231653A1 (en) | 2010-09-29 |
| AU2008334427A1 (en) | 2009-06-18 |
| WO2009074812A1 (en) | 2009-06-18 |
| CN102015700B (zh) | 2014-12-03 |
| GB0724342D0 (en) | 2008-01-30 |
| ES2416059T3 (es) | 2013-07-30 |
| MX2010006428A (es) | 2010-09-30 |
| EA018104B1 (ru) | 2013-05-30 |
| BRPI0820656A2 (pt) | 2015-06-16 |
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