CA2655403C - Antibacterial benzothiazoles and thiazolopyridines - Google Patents
Antibacterial benzothiazoles and thiazolopyridines Download PDFInfo
- Publication number
- CA2655403C CA2655403C CA2655403A CA2655403A CA2655403C CA 2655403 C CA2655403 C CA 2655403C CA 2655403 A CA2655403 A CA 2655403A CA 2655403 A CA2655403 A CA 2655403A CA 2655403 C CA2655403 C CA 2655403C
- Authority
- CA
- Canada
- Prior art keywords
- pyridin
- ethyl
- benzothiazol
- urea
- optionally substituted
- 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
Links
- 230000000844 anti-bacterial effect Effects 0.000 title abstract description 9
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 title description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 81
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 65
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 38
- 125000006413 ring segment Chemical group 0.000 claims abstract description 38
- 239000001257 hydrogen Substances 0.000 claims abstract description 37
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract description 31
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 27
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 20
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims abstract description 12
- 125000004450 alkenylene group Chemical group 0.000 claims abstract description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 11
- 150000003568 thioethers Chemical class 0.000 claims abstract description 8
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 7
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 7
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 7
- 239000004202 carbamide Substances 0.000 claims description 138
- -1 hydroxy (C1-C6)alkyl Chemical group 0.000 claims description 59
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 56
- 125000001424 substituent group Chemical group 0.000 claims description 35
- 229910052757 nitrogen Inorganic materials 0.000 claims description 30
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000002837 carbocyclic group Chemical group 0.000 claims description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 9
- 101100490437 Mus musculus Acvrl1 gene Proteins 0.000 claims description 8
- 208000035143 Bacterial infection Diseases 0.000 claims description 7
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 7
- 125000002527 bicyclic carbocyclic group Chemical group 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 6
- FSAFVTMBEIXIOA-UHFFFAOYSA-N methyl 2-(ethylcarbamoylamino)-5-pyridin-3-yl-1,3-benzothiazole-7-carboxylate Chemical compound C=1C(C(=O)OC)=C2SC(NC(=O)NCC)=NC2=CC=1C1=CC=CN=C1 FSAFVTMBEIXIOA-UHFFFAOYSA-N 0.000 claims description 6
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical class OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims description 6
- 239000012453 solvate Substances 0.000 claims description 6
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical compound [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 6
- RYECOJGRJDOGPP-UHFFFAOYSA-N Ethylurea Chemical compound CCNC(N)=O RYECOJGRJDOGPP-UHFFFAOYSA-N 0.000 claims description 5
- 150000001204 N-oxides Chemical class 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 229960003966 nicotinamide Drugs 0.000 claims description 5
- 239000011570 nicotinamide Substances 0.000 claims description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical class C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical class C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 4
- 125000003373 pyrazinyl group Chemical class 0.000 claims description 4
- 150000003222 pyridines Chemical class 0.000 claims description 4
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 3
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 3
- ZJEYDISTLAUSNQ-UHFFFAOYSA-N n-ethyl-2-(ethylcarbamoylamino)-5-pyridin-3-yl-1,3-benzothiazole-7-carboxamide Chemical compound C=1C(C(=O)NCC)=C2SC(NC(=O)NCC)=NC2=CC=1C1=CC=CN=C1 ZJEYDISTLAUSNQ-UHFFFAOYSA-N 0.000 claims description 3
- 150000002825 nitriles Chemical class 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 150000003216 pyrazines Chemical group 0.000 claims description 3
- 150000003230 pyrimidines Chemical group 0.000 claims description 3
- MAYZWDRUFKUGGP-VIFPVBQESA-N (3s)-1-[5-tert-butyl-3-[(1-methyltetrazol-5-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound CN1N=NN=C1CN1C2=NC(C(C)(C)C)=NC(N3C[C@@H](O)CC3)=C2N=N1 MAYZWDRUFKUGGP-VIFPVBQESA-N 0.000 claims description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Chemical class C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- KUMKXVOROOAIRR-UHFFFAOYSA-N 1-(7-amino-5-pyridin-3-yl-1,3-benzothiazol-2-yl)-3-ethylurea Chemical compound C=1C(N)=C2SC(NC(=O)NCC)=NC2=CC=1C1=CC=CN=C1 KUMKXVOROOAIRR-UHFFFAOYSA-N 0.000 claims 1
- MRRPDPOIHPFYNW-UHFFFAOYSA-N 1-[5,7-bis(1-methylpyrazol-4-yl)-1,3-benzothiazol-2-yl]-3-ethylurea Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C2=CN(C)N=C2)=CC=1C=1C=NN(C)C=1 MRRPDPOIHPFYNW-UHFFFAOYSA-N 0.000 claims 1
- ZBJYXYKHZFHMPO-UHFFFAOYSA-N 1-[5,7-di(pyrimidin-5-yl)-1,3-benzothiazol-2-yl]-3-ethylurea Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC=NC=2)=CC=1C1=CN=CN=C1 ZBJYXYKHZFHMPO-UHFFFAOYSA-N 0.000 claims 1
- CFWCKJNRCHEEKD-UHFFFAOYSA-N 1-[5-(2-aminopyrimidin-5-yl)-7-pyrazin-2-yl-1,3-benzothiazol-2-yl]-3-ethylurea Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(N)=NC=2)=CC=1C1=CN=CC=N1 CFWCKJNRCHEEKD-UHFFFAOYSA-N 0.000 claims 1
- HPBSMKUOLBZKIE-UHFFFAOYSA-N 1-[5-(2-aminopyrimidin-5-yl)-7-pyridin-3-yl-1,3-benzothiazol-2-yl]-3-ethylurea Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(N)=NC=2)=CC=1C1=CC=CN=C1 HPBSMKUOLBZKIE-UHFFFAOYSA-N 0.000 claims 1
- AJZLNBKKEWGATB-UHFFFAOYSA-N 1-[5-(2-cyanopyrimidin-5-yl)-7-pyridin-3-yl-1,3-benzothiazol-2-yl]-3-ethylurea Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)C#N)=CC=1C1=CC=CN=C1 AJZLNBKKEWGATB-UHFFFAOYSA-N 0.000 claims 1
- DGQOGPCRIBUGLH-UHFFFAOYSA-N 1-[5-(5-chloropyridin-3-yl)-7-pyridin-3-yl-1,3-benzothiazol-2-yl]-3-ethylurea Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=C(Cl)C=NC=2)=CC=1C1=CC=CN=C1 DGQOGPCRIBUGLH-UHFFFAOYSA-N 0.000 claims 1
- SGNSLTNPBLDLEZ-UHFFFAOYSA-N 1-[5-(6-aminopyrazin-2-yl)-7-pyridin-3-yl-1,3-benzothiazol-2-yl]-3-ethylurea Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2N=C(N)C=NC=2)=CC=1C1=CC=CN=C1 SGNSLTNPBLDLEZ-UHFFFAOYSA-N 0.000 claims 1
- TXXAQXDFAXOYFS-UHFFFAOYSA-N 1-[5-(6-aminopyridin-3-yl)-7-pyridin-2-yl-1,3-benzothiazol-2-yl]-3-ethylurea Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(N)=CC=2)=CC=1C1=CC=CC=N1 TXXAQXDFAXOYFS-UHFFFAOYSA-N 0.000 claims 1
- OUKIFLPQSOIEKT-UHFFFAOYSA-N 1-[5-(6-cyanopyridin-3-yl)-7-pyridin-2-yl-1,3-benzothiazol-2-yl]-3-ethylurea Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=CC=2)C#N)=CC=1C1=CC=CC=N1 OUKIFLPQSOIEKT-UHFFFAOYSA-N 0.000 claims 1
- RPJBQQRLJVLNRR-UHFFFAOYSA-N 1-[5-[2-(dimethylamino)pyrimidin-5-yl]-7-pyridin-3-yl-1,3-benzothiazol-2-yl]-3-ethylurea Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(=NC=2)N(C)C)=CC=1C1=CC=CN=C1 RPJBQQRLJVLNRR-UHFFFAOYSA-N 0.000 claims 1
- RQVNNYJFQUZWRT-UHFFFAOYSA-N 1-[7-(1,3-benzothiazol-2-yl)-5-pyridin-3-yl-1,3-benzothiazol-2-yl]-3-ethylurea Chemical compound C=1C(C=2SC3=CC=CC=C3N=2)=C2SC(NC(=O)NCC)=NC2=CC=1C1=CC=CN=C1 RQVNNYJFQUZWRT-UHFFFAOYSA-N 0.000 claims 1
- OHIXHNTWIXIVIZ-UHFFFAOYSA-N 1-[7-(2-aminopyrimidin-5-yl)-5-pyrazin-2-yl-1,3-benzothiazol-2-yl]-3-ethylurea Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2N=CC=NC=2)=CC=1C1=CN=C(N)N=C1 OHIXHNTWIXIVIZ-UHFFFAOYSA-N 0.000 claims 1
- DQWYULLSSJKHBK-UHFFFAOYSA-N 1-[7-(3-aminopyridin-2-yl)-5-pyridin-3-yl-1,3-benzothiazol-2-yl]-3-ethylurea Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC=CC=2)=CC=1C1=NC=CC=C1N DQWYULLSSJKHBK-UHFFFAOYSA-N 0.000 claims 1
- VJNMTIUXMVZVAP-UHFFFAOYSA-N 1-[7-(3-cyano-6-methylpyridin-2-yl)-5-pyridin-3-yl-1,3-benzothiazol-2-yl]-3-ethylurea Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC=CC=2)=CC=1C1=NC(C)=CC=C1C#N VJNMTIUXMVZVAP-UHFFFAOYSA-N 0.000 claims 1
- ONKDPPMLHRXFQN-UHFFFAOYSA-N 1-[7-(4-aminopyridin-2-yl)-5-pyridin-3-yl-1,3-benzothiazol-2-yl]-3-ethylurea Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC=CC=2)=CC=1C1=CC(N)=CC=N1 ONKDPPMLHRXFQN-UHFFFAOYSA-N 0.000 claims 1
- GDGLPVCJEUHLRP-UHFFFAOYSA-N 1-[7-(4-aminopyrimidin-2-yl)-5-pyridin-3-yl-1,3-benzothiazol-2-yl]-3-ethylurea Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC=CC=2)=CC=1C1=NC=CC(N)=N1 GDGLPVCJEUHLRP-UHFFFAOYSA-N 0.000 claims 1
- DZFRCNWYMRXKAP-UHFFFAOYSA-N 1-[7-(4-chloropyridin-2-yl)-5-pyridin-3-yl-1,3-benzothiazol-2-yl]-3-ethylurea Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC=CC=2)=CC=1C1=CC(Cl)=CC=N1 DZFRCNWYMRXKAP-UHFFFAOYSA-N 0.000 claims 1
- XDPUMNMPAAJQMU-UHFFFAOYSA-N 1-[7-(4-cyanopyridin-2-yl)-5-pyridin-3-yl-1,3-benzothiazol-2-yl]-3-ethylurea Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC=CC=2)=CC=1C1=CC(C#N)=CC=N1 XDPUMNMPAAJQMU-UHFFFAOYSA-N 0.000 claims 1
- BOSZPPFLQLCFIM-UHFFFAOYSA-N 1-[7-(5-aminopyridin-2-yl)-5-pyridin-3-yl-1,3-benzothiazol-2-yl]-3-ethylurea Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC=CC=2)=CC=1C1=CC=C(N)C=N1 BOSZPPFLQLCFIM-UHFFFAOYSA-N 0.000 claims 1
- PQNXEOZMHDLBGR-UHFFFAOYSA-N 1-[7-(5-cyanopyridin-2-yl)-5-pyridin-3-yl-1,3-benzothiazol-2-yl]-3-ethylurea Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC=CC=2)=CC=1C1=CC=C(C#N)C=N1 PQNXEOZMHDLBGR-UHFFFAOYSA-N 0.000 claims 1
- RECWBEOJASYSOG-UHFFFAOYSA-N 1-[7-(6-aminopyrazin-2-yl)-5-pyridin-3-yl-1,3-benzothiazol-2-yl]-3-ethylurea Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC=CC=2)=CC=1C1=CN=CC(N)=N1 RECWBEOJASYSOG-UHFFFAOYSA-N 0.000 claims 1
- GEZHFBUOOJXDAC-UHFFFAOYSA-N 1-[7-(6-chloropyridin-2-yl)-5-pyridin-3-yl-1,3-benzothiazol-2-yl]-3-ethylurea Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC=CC=2)=CC=1C1=CC=CC(Cl)=N1 GEZHFBUOOJXDAC-UHFFFAOYSA-N 0.000 claims 1
- CZWBQAVOCOBPBR-UHFFFAOYSA-N 1-[7-[4-(dimethylamino)pyridin-2-yl]-5-pyridin-3-yl-1,3-benzothiazol-2-yl]-3-ethylurea Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC=CC=2)=CC=1C1=CC(N(C)C)=CC=N1 CZWBQAVOCOBPBR-UHFFFAOYSA-N 0.000 claims 1
- DVLMTBOWJUJRBM-UHFFFAOYSA-N 1-[7-[5-(aminomethyl)pyridin-2-yl]-5-pyridin-3-yl-1,3-benzothiazol-2-yl]-3-ethylurea Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC=CC=2)=CC=1C1=CC=C(CN)C=N1 DVLMTBOWJUJRBM-UHFFFAOYSA-N 0.000 claims 1
- PJYPXMWMLPCFRN-UHFFFAOYSA-N 1-[7-[6-(dimethylamino)pyridin-2-yl]-5-pyridin-3-yl-1,3-benzothiazol-2-yl]-3-ethylurea Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC=CC=2)=CC=1C1=CC=CC(N(C)C)=N1 PJYPXMWMLPCFRN-UHFFFAOYSA-N 0.000 claims 1
- YKLAJZXUMZQNHG-UHFFFAOYSA-N 1-ethyl-3-(5-imidazo[1,2-a]pyridin-6-yl-7-pyridin-3-yl-1,3-benzothiazol-2-yl)urea Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C2=CN3C=CN=C3C=C2)=CC=1C1=CC=CN=C1 YKLAJZXUMZQNHG-UHFFFAOYSA-N 0.000 claims 1
- FEHICRUGJSEKAY-UHFFFAOYSA-N 1-ethyl-3-(5-pyrazin-2-yl-7-pyridin-3-yl-1,3-benzothiazol-2-yl)urea Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2N=CC=NC=2)=CC=1C1=CC=CN=C1 FEHICRUGJSEKAY-UHFFFAOYSA-N 0.000 claims 1
- NXSFAKLMWJRZFT-UHFFFAOYSA-N 1-ethyl-3-(5-pyrazol-1-yl-7-pyridin-3-yl-1,3-benzothiazol-2-yl)urea Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(N2N=CC=C2)=CC=1C1=CC=CN=C1 NXSFAKLMWJRZFT-UHFFFAOYSA-N 0.000 claims 1
- PCCJEQLSUVKRTO-UHFFFAOYSA-N 1-ethyl-3-(5-pyridin-3-yl-7-pyrimidin-5-yl-1,3-benzothiazol-2-yl)urea Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC=CC=2)=CC=1C1=CN=CN=C1 PCCJEQLSUVKRTO-UHFFFAOYSA-N 0.000 claims 1
- PHOLAVRNANURJG-UHFFFAOYSA-N 1-ethyl-3-(5-pyridin-3-yl-7-thiophen-3-yl-1,3-benzothiazol-2-yl)urea Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC=CC=2)=CC=1C=1C=CSC=1 PHOLAVRNANURJG-UHFFFAOYSA-N 0.000 claims 1
- QPLVOQVQJITTPF-UHFFFAOYSA-N 1-ethyl-3-(7-prop-2-enyl-5-pyridin-3-yl-1,3-benzothiazol-2-yl)urea Chemical compound C=1C(CC=C)=C2SC(NC(=O)NCC)=NC2=CC=1C1=CC=CN=C1 QPLVOQVQJITTPF-UHFFFAOYSA-N 0.000 claims 1
- PRFSZCFWCRVGKH-UHFFFAOYSA-N 1-ethyl-3-(7-pyrazin-2-yl-5-pyridin-3-yl-1,3-benzothiazol-2-yl)urea Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC=CC=2)=CC=1C1=CN=CC=N1 PRFSZCFWCRVGKH-UHFFFAOYSA-N 0.000 claims 1
- KUWYVAUKYBZDIJ-UHFFFAOYSA-N 1-ethyl-3-(7-pyrazol-1-yl-5-pyridin-3-yl-1,3-benzothiazol-2-yl)urea Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC=CC=2)=CC=1N1C=CC=N1 KUWYVAUKYBZDIJ-UHFFFAOYSA-N 0.000 claims 1
- CFKVOPUFKPCECS-UHFFFAOYSA-N 1-ethyl-3-(7-pyridazin-3-yl-5-pyridin-3-yl-1,3-benzothiazol-2-yl)urea Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC=CC=2)=CC=1C1=CC=CN=N1 CFKVOPUFKPCECS-UHFFFAOYSA-N 0.000 claims 1
- YDZVDTLMNTWEPN-UHFFFAOYSA-N 1-ethyl-3-(7-pyridin-2-yl-5-pyridin-3-yl-1,3-benzothiazol-2-yl)urea Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC=CC=2)=CC=1C1=CC=CC=N1 YDZVDTLMNTWEPN-UHFFFAOYSA-N 0.000 claims 1
- PPWKMLFMRSVQIV-UHFFFAOYSA-N 1-ethyl-3-(7-pyridin-2-yl-5-pyrimidin-5-yl-1,3-benzothiazol-2-yl)urea Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC=NC=2)=CC=1C1=CC=CC=N1 PPWKMLFMRSVQIV-UHFFFAOYSA-N 0.000 claims 1
- LHSHJAAHGFIHTL-UHFFFAOYSA-N 1-ethyl-3-(7-pyridin-3-yl-5-pyridin-4-yl-1,3-benzothiazol-2-yl)urea Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=CN=CC=2)=CC=1C1=CC=CN=C1 LHSHJAAHGFIHTL-UHFFFAOYSA-N 0.000 claims 1
- PXOCVHYSXWHIDH-UHFFFAOYSA-N 1-ethyl-3-(7-pyridin-3-yl-5-pyrimidin-5-yl-1,3-benzothiazol-2-yl)urea Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC=NC=2)=CC=1C1=CC=CN=C1 PXOCVHYSXWHIDH-UHFFFAOYSA-N 0.000 claims 1
- GNCWBEQDICQXGO-UHFFFAOYSA-N 1-ethyl-3-[2-(ethylcarbamoylamino)-5-pyridin-3-yl-1,3-benzothiazol-7-yl]urea Chemical compound C=1C(NC(=O)NCC)=C2SC(NC(=O)NCC)=NC2=CC=1C1=CC=CN=C1 GNCWBEQDICQXGO-UHFFFAOYSA-N 0.000 claims 1
- DJYXSKJUBUOKBE-UHFFFAOYSA-N 1-ethyl-3-[5-(2-methoxypyrimidin-5-yl)-7-pyridin-3-yl-1,3-benzothiazol-2-yl]urea Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(OC)=NC=2)=CC=1C1=CC=CN=C1 DJYXSKJUBUOKBE-UHFFFAOYSA-N 0.000 claims 1
- GEAIQWXNJMGBCY-UHFFFAOYSA-N 1-ethyl-3-[5-(2-oxo-1h-pyridin-4-yl)-7-pyridin-2-yl-1,3-benzothiazol-2-yl]urea Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C2=CC(=O)NC=C2)=CC=1C1=CC=CC=N1 GEAIQWXNJMGBCY-UHFFFAOYSA-N 0.000 claims 1
- VZFOHTNRXUDSSK-UHFFFAOYSA-N 1-ethyl-3-[5-(3-fluorophenyl)-7-pyridin-3-yl-1,3-benzothiazol-2-yl]urea Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=C(F)C=CC=2)=CC=1C1=CC=CN=C1 VZFOHTNRXUDSSK-UHFFFAOYSA-N 0.000 claims 1
- XXJPFWVLKKJBKY-UHFFFAOYSA-N 1-ethyl-3-[5-(5-methoxypyridin-3-yl)-7-pyridin-2-yl-1,3-benzothiazol-2-yl]urea Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=C(OC)C=NC=2)=CC=1C1=CC=CC=N1 XXJPFWVLKKJBKY-UHFFFAOYSA-N 0.000 claims 1
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- 229910017604 nitric acid Inorganic materials 0.000 description 1
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- YJQPYGGHQPGBLI-KGSXXDOSSA-N novobiocin Chemical compound O1C(C)(C)[C@H](OC)[C@@H](OC(N)=O)[C@@H](O)[C@@H]1OC1=CC=C(C(O)=C(NC(=O)C=2C=C(CC=C(C)C)C(O)=CC=2)C(=O)O2)C2=C1C YJQPYGGHQPGBLI-KGSXXDOSSA-N 0.000 description 1
- 229960002950 novobiocin Drugs 0.000 description 1
- 229940006093 opthalmologic coloring agent diagnostic Drugs 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 229960000321 oxolinic acid Drugs 0.000 description 1
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 239000003182 parenteral nutrition solution Substances 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229940096826 phenylmercuric acetate Drugs 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
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- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 239000004323 potassium nitrate Substances 0.000 description 1
- 235000010333 potassium nitrate Nutrition 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 229960002429 proline Drugs 0.000 description 1
- 229940055019 propionibacterium acne Drugs 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- UMLDUMMLRZFROX-UHFFFAOYSA-N pyridin-2-ylboronic acid Chemical compound OB(O)C1=CC=CC=N1 UMLDUMMLRZFROX-UHFFFAOYSA-N 0.000 description 1
- 125000005494 pyridonyl group Chemical group 0.000 description 1
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 230000010076 replication Effects 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 229910052709 silver Inorganic materials 0.000 description 1
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- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
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- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
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- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229940063673 spermidine Drugs 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 229940037649 staphylococcus haemolyticus Drugs 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- WPLOVIFNBMNBPD-ATHMIXSHSA-N subtilin Chemical compound CC1SCC(NC2=O)C(=O)NC(CC(N)=O)C(=O)NC(C(=O)NC(CCCCN)C(=O)NC(C(C)CC)C(=O)NC(=C)C(=O)NC(CCCCN)C(O)=O)CSC(C)C2NC(=O)C(CC(C)C)NC(=O)C1NC(=O)C(CCC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C1NC(=O)C(=C/C)/NC(=O)C(CCC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)CNC(=O)C(NC(=O)C(NC(=O)C2NC(=O)CNC(=O)C3CCCN3C(=O)C(NC(=O)C3NC(=O)C(CC(C)C)NC(=O)C(=C)NC(=O)C(CCC(O)=O)NC(=O)C(NC(=O)C(CCCCN)NC(=O)C(N)CC=4C5=CC=CC=C5NC=4)CSC3)C(C)SC2)C(C)C)C(C)SC1)CC1=CC=CC=C1 WPLOVIFNBMNBPD-ATHMIXSHSA-N 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000002278 tabletting lubricant Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- GYUURHMITDQTRU-UHFFFAOYSA-N tributyl(pyridin-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=CC=N1 GYUURHMITDQTRU-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- VHXPMXQCMIGWIS-UHFFFAOYSA-M zinc;5-methyl-2h-pyridin-2-ide;bromide Chemical compound Br[Zn+].CC1=CC=[C-]N=C1 VHXPMXQCMIGWIS-UHFFFAOYSA-M 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/04—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/4965—Non-condensed pyrazines
- A61K31/497—Non-condensed pyrazines containing further heterocyclic 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
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)
- Epidemiology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0612428.3 | 2006-06-22 | ||
| GBGB0612428.3A GB0612428D0 (en) | 2006-06-22 | 2006-06-22 | Antibacterial agents |
| PCT/GB2007/002314 WO2007148093A1 (en) | 2006-06-22 | 2007-06-21 | Antibacterial compositions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2655403A1 CA2655403A1 (en) | 2007-12-27 |
| CA2655403C true CA2655403C (en) | 2014-02-04 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2655403A Expired - Fee Related CA2655403C (en) | 2006-06-22 | 2007-06-21 | Antibacterial benzothiazoles and thiazolopyridines |
Country Status (21)
| Country | Link |
|---|---|
| US (2) | US7977340B2 (enExample) |
| EP (1) | EP2034997B1 (enExample) |
| JP (1) | JP5309021B2 (enExample) |
| KR (1) | KR101443795B1 (enExample) |
| CN (1) | CN101472585B (enExample) |
| AU (1) | AU2007262791B2 (enExample) |
| BR (1) | BRPI0713501A2 (enExample) |
| CA (1) | CA2655403C (enExample) |
| DK (1) | DK2034997T3 (enExample) |
| EA (1) | EA019748B1 (enExample) |
| ES (1) | ES2403005T3 (enExample) |
| GB (1) | GB0612428D0 (enExample) |
| IL (1) | IL195687A (enExample) |
| MX (1) | MX2008015706A (enExample) |
| MY (1) | MY148682A (enExample) |
| NZ (1) | NZ574313A (enExample) |
| PL (1) | PL2034997T3 (enExample) |
| PT (1) | PT2034997E (enExample) |
| SG (1) | SG172676A1 (enExample) |
| WO (1) | WO2007148093A1 (enExample) |
| ZA (1) | ZA200900240B (enExample) |
Families Citing this family (51)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8481544B2 (en) | 2006-06-22 | 2013-07-09 | Biota Europe Limited | Antibacterial compositions |
| GB0724349D0 (en) * | 2007-12-13 | 2008-01-30 | Prolysis Ltd | Antibacterial agents |
| GB0612428D0 (en) | 2006-06-22 | 2006-08-02 | Prolysis Ltd | Antibacterial agents |
| BRPI0720057A2 (pt) | 2006-12-04 | 2013-12-17 | Astrazeneca Ab | Composto ou um sal farmaceuticamente aceitável do mesmo, composição farmacêutica, métodos de inibição de girase bacteriana de dna e/ou topoisomerase iv bacteriana em um animal de sangue quente, de produção de um efeito antibacteriano em um animal de sangue quente e de tratamento de uma infecção bacteriana em um animal de sangue quente, e, uso de um composto ou um sal farmaceuticamente aceitável do mesmo |
| GB0724342D0 (en) | 2007-12-13 | 2008-01-30 | Prolysis Ltd | Anitbacterial compositions |
| DE102008022221A1 (de) | 2008-05-06 | 2009-11-12 | Universität des Saarlandes | Inhibitoren der humanen Aldosteronsynthase CYP11B2 |
| EP2296653B1 (en) | 2008-06-03 | 2016-01-27 | Intermune, Inc. | Compounds and methods for treating inflammatory and fibrotic disorders |
| US20110166088A1 (en) * | 2008-06-25 | 2011-07-07 | Ranbaxy Laboratories Limited | Benzothiazoles and aza-analogues thereof use as antibacterial agents |
| GB0821913D0 (en) | 2008-12-02 | 2009-01-07 | Price & Co | Antibacterial compounds |
| EP2277870A1 (de) * | 2009-06-24 | 2011-01-26 | Bayer CropScience AG | Substituierte Benzoxa(thia)zole |
| US8541404B2 (en) | 2009-11-09 | 2013-09-24 | Elexopharm Gmbh | Inhibitors of the human aldosterone synthase CYP11B2 |
| KR20130012072A (ko) | 2010-03-31 | 2013-01-31 | 액테리온 파마슈티칼 리미티드 | 항박테리아성 이소퀴놀린-３-일우레아 유도체 |
| WO2011151619A1 (en) | 2010-06-01 | 2011-12-08 | Summit Corporation Plc | Compounds for the treatment of clostridium difficile associated disease |
| SI2575968T1 (sl) | 2010-06-01 | 2016-06-30 | Summit Therapeutics Plc | Spojine za zdravljenje bolezni, ki je povezana s clostridium difficile |
| WO2011151620A1 (en) | 2010-06-01 | 2011-12-08 | Summit Corporation Plc | Compounds for the treatment of clostridium difficile associated disease |
| WO2011151617A1 (en) | 2010-06-01 | 2011-12-08 | Summit Corporation Plc | Compounds for the treatment of clostridium difficile associated disease |
| WO2011151618A2 (en) | 2010-06-01 | 2011-12-08 | Summit Corporation Plc | Compounds for the treatment of clostridium difficile-associated disease |
| SG191946A1 (en) | 2011-01-14 | 2013-08-30 | Vertex Pharma | Pyrimidine gyrase and topoisomerase iv inhibitors |
| ES2705923T3 (es) | 2011-01-14 | 2019-03-27 | Spero Trinem Inc | Formas sólidas de inhibidor de girasa (R)-1-etil-3-[6-fluoro-5-[2-(1-hidroxi-1-metil-etil)pirimidin-5-il]-7-(tetrahidrofuran-2-il)-1H-bencimidazol-2-il]urea |
| EP2663558A1 (en) | 2011-01-14 | 2013-11-20 | Vertex Pharmaceuticals Incorporated | Solid forms of gyrase inhibitor (r)-1-ethyl-3-[5-[2-{1-hydroxy-1-methyl-ethyl}pyrimidin-5-yl]-7-(tetrahydrofuran-2-yl}-1h-benzimidazol-2-yl]urea |
| EP2663556B1 (en) | 2011-01-14 | 2014-10-15 | Vertex Pharmaceuticals Incorporated | Process of making gyrase and topoisomerase iv inhibitors |
| AR088729A1 (es) | 2011-03-29 | 2014-07-02 | Actelion Pharmaceuticals Ltd | Derivados de 3-ureidoisoquinolin-8-ilo y una composicion farmaceutica |
| 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 |
| WO2013106756A2 (en) | 2012-01-13 | 2013-07-18 | Rutgers, The State University Of New Jersey | Antimicrobial agents |
| EP2828245A1 (en) | 2012-03-21 | 2015-01-28 | Rutgers, The State University of New Jersey | Antimicrobial agents |
| CN104302645A (zh) * | 2012-03-22 | 2015-01-21 | 生物区欧洲有限公司 | 抗菌化合物 |
| US9572809B2 (en) | 2012-07-18 | 2017-02-21 | Spero Trinem, Inc. | Combination therapy to treat Mycobacterium diseases |
| WO2014015105A1 (en) | 2012-07-18 | 2014-01-23 | 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 |
| US9079935B2 (en) | 2012-08-13 | 2015-07-14 | The Board Of Regents Of The Nevada System Of Higher Education On Behalf Of The University Of Nevada, Las Vegas | Reducing risk of contracting Clostridium-difficile associated disease |
| AR092742A1 (es) | 2012-10-02 | 2015-04-29 | Intermune Inc | Piridinonas antifibroticas |
| US20160194279A1 (en) * | 2012-12-09 | 2016-07-07 | Council Of Scientific & Industrial Research | One pot process for the conversion of aroyl chlorides to acyl thioureas |
| US9458150B2 (en) | 2013-11-08 | 2016-10-04 | Rutgers, The State University Of New Jersey | Antimicrobial agents |
| BR112016018048A2 (pt) | 2014-02-03 | 2017-08-08 | Spero Gyrase Inc | Método para o tratamento ou prevenção de uma infecção bacteriana, uso de um inibidor de topoisomerase tipo ii bacteriana em combinação com uma polimixina ou derivado de polimixina no tratamento ou prevenção de uma infecção bacteriana, uso de um inibidor de topoisomerase tipo ii bacteriana em combinação com uma polimixina ou derivado de polimixina na preparação de um medicamento para o tratamento ou prevenção de uma infecção bacteriana, método para melhorar a atividade antibacteriana de um inibidor de topoisomerase tipo ii bacteriana, método para melhorar a eficácia bactericida de um inibidor de topoisomerase tipo ii bacteriana, composição, agente antibacteriano, processo, e, composto |
| RU2692485C2 (ru) | 2014-04-02 | 2019-06-25 | Интермьюн, Инк. | Противофиброзные пиридиноны |
| BR112017011791A2 (pt) * | 2014-12-02 | 2018-02-27 | Bayer Cropscience Aktiengesellschaft | compostos bicíclicos como agentes de controle de pragas |
| US20180000793A1 (en) | 2015-02-06 | 2018-01-04 | Ernesto Abel-Santos | Inhibiting Germination of Clostridium Perfringens Spores to Reduce Necrotic Enteritis |
| AR104259A1 (es) | 2015-04-15 | 2017-07-05 | Celgene Quanticel Res Inc | Inhibidores de bromodominio |
| CN106167486B (zh) * | 2015-05-22 | 2019-06-14 | 北京四环制药有限公司 | 单环类回旋酶和拓扑异构酶iv抑制剂 |
| CA3015768A1 (en) | 2016-02-25 | 2017-08-31 | Taxis Pharmaceuticals, Inc. | Synthetic processes and intermediates |
| MX2019008230A (es) | 2017-01-10 | 2019-10-24 | Bayer Ag | Derivados heterociclicos como agentes de control de plagas. |
| RU2019133662A (ru) | 2017-03-24 | 2021-04-26 | Тайсо Фармасьютикал Ко., Лтд. | Производное 2(1h)-хинолинона |
| EP3600298A4 (en) | 2017-03-30 | 2020-11-11 | Taxis Pharmaceuticals, Inc. | SYNTHESIS AND SYNTHESIS INTERMEDIARIES |
| TWI820231B (zh) | 2018-10-11 | 2023-11-01 | 德商拜耳廠股份有限公司 | 用於製備經取代咪唑衍生物之方法 |
| EP3999502A1 (en) | 2019-07-17 | 2022-05-25 | Summit (Oxford) Limited | Process for the preparation of ridinilazole and crystalline forms thereof |
| US20230247994A1 (en) | 2020-07-02 | 2023-08-10 | Bayer Aktiengesellschaft | Heterocyclene derivatives as pest control agents |
| GB202100470D0 (en) | 2021-01-14 | 2021-03-03 | Summit Oxford Ltd | Solid tablet dosage for of ridinilazole |
| GB202100471D0 (en) | 2021-01-14 | 2021-03-03 | Summit Oxford Ltd | Preparation of antibacterial compounds |
| US12220421B2 (en) | 2021-09-09 | 2025-02-11 | The Boards Of Regents Of The Nevada System Of Higher Education On Behalf Of The University Of Nevada, Las | Inhibitors of C. difficile spore germination |
| CN116444376B (zh) * | 2023-04-19 | 2024-01-26 | 德兴市德邦化工有限公司 | 一种3,5-二氯硝基苯的生产工艺 |
| WO2025026738A1 (en) | 2023-07-31 | 2025-02-06 | Bayer Aktiengesellschaft | 6-[5-(ethylsulfonyl)-1-methyl-1h-imidazol-4-yl]-7-methyl-3-(pentafluoroethyl)-7h-imidazo[4,5-c]pyridazine derivatives as pesticides |
| CN119350937B (zh) * | 2024-10-30 | 2025-08-12 | 广东豪之盛新材料有限公司 | 一种双组份气雾喷漆及其制备方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3810988A (en) * | 1968-11-01 | 1974-05-14 | Ciba Geigy Ag | Control of phytopathogenic fungi with n-benzothiazae-2-yl n-{40 {11 propylure |
| 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 |
| US7091227B2 (en) | 2000-02-07 | 2006-08-15 | Abbott Gmbh & Co. Kg | Benzothiazole derivatives |
| BR0112395A (pt) | 2000-06-21 | 2003-07-08 | Hoffmann La Roche | Derivados de benzotiazol |
| SI1341769T1 (sl) | 2000-12-15 | 2008-02-29 | Vertex Pharma | Inhibitorji bakterijske giraze in njihove uporabe |
| 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 |
| EP1790640A4 (en) * | 2004-09-09 | 2009-07-29 | Chugai Pharmaceutical Co Ltd | NEW IMIDAZOLIDINE DERIVATIVE AND APPLICATION THEREOF |
| GB0612428D0 (en) | 2006-06-22 | 2006-08-02 | Prolysis Ltd | Antibacterial agents |
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- 2007-06-21 DK DK07733310T patent/DK2034997T3/da active
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| US20110263590A1 (en) | 2011-10-27 |
| WO2007148093A1 (en) | 2007-12-27 |
| KR20090029817A (ko) | 2009-03-23 |
| IL195687A (en) | 2013-12-31 |
| US8389516B2 (en) | 2013-03-05 |
| AU2007262791B2 (en) | 2012-11-08 |
| EA200900047A1 (ru) | 2009-06-30 |
| JP2009541289A (ja) | 2009-11-26 |
| PL2034997T3 (pl) | 2013-04-30 |
| GB0612428D0 (en) | 2006-08-02 |
| ES2403005T3 (es) | 2013-05-13 |
| BRPI0713501A2 (pt) | 2012-03-13 |
| CA2655403A1 (en) | 2007-12-27 |
| KR101443795B1 (ko) | 2014-10-21 |
| AU2007262791A1 (en) | 2007-12-27 |
| MX2008015706A (es) | 2009-03-31 |
| CN101472585B (zh) | 2013-12-04 |
| IL195687A0 (en) | 2009-09-01 |
| US7977340B2 (en) | 2011-07-12 |
| DK2034997T3 (da) | 2013-02-11 |
| EA019748B1 (ru) | 2014-06-30 |
| EP2034997A1 (en) | 2009-03-18 |
| MY148682A (en) | 2013-05-31 |
| CN101472585A (zh) | 2009-07-01 |
| JP5309021B2 (ja) | 2013-10-09 |
| US20090197877A1 (en) | 2009-08-06 |
| PT2034997E (pt) | 2013-01-24 |
| EP2034997B1 (en) | 2012-10-17 |
| ZA200900240B (en) | 2009-12-30 |
| NZ574313A (en) | 2011-10-28 |
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