AU2007262791B2 - Antibacterial compositions - Google Patents

Info

Publication number

AU2007262791B2

AU2007262791B2 AU2007262791A AU2007262791A AU2007262791B2 AU 2007262791 B2 AU2007262791 B2 AU 2007262791B2 AU 2007262791 A AU2007262791 A AU 2007262791A AU 2007262791 A AU2007262791 A AU 2007262791A AU 2007262791 B2 AU2007262791 B2 AU 2007262791B2

Authority

AU

Australia

Prior art keywords

pyridin

ethyl

benzothiazol

urea

amino

Prior art date

2006-06-22

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.)

Ceased

Links

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• Global Dossier
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• 230000000844 anti-bacterial effect Effects 0.000 title claims abstract description 11
• 239000000203 mixture Substances 0.000 title claims description 47
• 150000001875 compounds Chemical class 0.000 claims abstract description 96
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 61
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 30
• 239000001257 hydrogen Substances 0.000 claims abstract description 29
• 125000006413 ring segment Chemical group 0.000 claims abstract description 27
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 24
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 15
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 10
• 125000004450 alkenylene group Chemical group 0.000 claims abstract description 8
• 125000002947 alkylene group Chemical group 0.000 claims abstract description 8
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 7
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 6
• 150000003568 thioethers Chemical class 0.000 claims abstract description 6
• 125000003342 alkenyl group Chemical group 0.000 claims abstract description 4
• 239000004202 carbamide Substances 0.000 claims description 159
• -1 alkynylene radical Chemical class 0.000 claims description 73
• 125000004190 benzothiazol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N=C(*)SC2=C1[H] 0.000 claims description 68
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 42
• 125000001424 substituent group Chemical group 0.000 claims description 21
• 230000001580 bacterial effect Effects 0.000 claims description 16
• 150000003254 radicals Chemical class 0.000 claims description 15
• 150000003839 salts Chemical class 0.000 claims description 14
• 238000000034 method Methods 0.000 claims description 12
• 125000004432 carbon atom Chemical group C* 0.000 claims description 11
• RYECOJGRJDOGPP-UHFFFAOYSA-N Ethylurea Chemical compound CCNC(N)=O RYECOJGRJDOGPP-UHFFFAOYSA-N 0.000 claims description 9
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
• 125000002837 carbocyclic group Chemical group 0.000 claims description 8
• 238000011109 contamination Methods 0.000 claims description 8
• 238000002360 preparation method Methods 0.000 claims description 8
• JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
• 208000035143 Bacterial infection Diseases 0.000 claims description 7
• 208000022362 bacterial infectious disease Diseases 0.000 claims description 7
• 239000012453 solvate Substances 0.000 claims description 7
• 150000001204 N-oxides Chemical class 0.000 claims description 6
• 125000003545 alkoxy group Chemical group 0.000 claims description 6
• 125000002527 bicyclic carbocyclic group Chemical group 0.000 claims description 6
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
• 125000004193 piperazinyl group Chemical group 0.000 claims description 6
• DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 6
• 125000002757 morpholinyl group Chemical group 0.000 claims description 5
• 229960003966 nicotinamide Drugs 0.000 claims description 5
• 239000011570 nicotinamide Substances 0.000 claims description 5
• 125000003386 piperidinyl group Chemical group 0.000 claims description 5
• UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical group OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims description 5
• 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 description 4
• 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 4
• 125000003373 pyrazinyl group Chemical class 0.000 claims description 4
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
• AVWSSTUQTRXLKU-UHFFFAOYSA-N 1-(4,6-dipyridin-2-yl-1,3-benzothiazol-2-yl)-3-ethylurea Chemical compound C1=C2SC(NC(=O)NCC)=NC2=C(C=2N=CC=CC=2)C=C1C1=CC=CC=N1 AVWSSTUQTRXLKU-UHFFFAOYSA-N 0.000 claims description 3
• RPAMVQYUDWHMIP-UHFFFAOYSA-N 1-ethyl-3-[5-(2-oxopyridin-1-yl)-7-pyridin-3-yl-1,3-benzothiazol-2-yl]urea Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(N2C(C=CC=C2)=O)=CC=1C1=CC=CN=C1 RPAMVQYUDWHMIP-UHFFFAOYSA-N 0.000 claims description 3
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical class C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 3
• 125000002496 methyl group Chemical group [H]C([H])([H])* 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
• 150000003222 pyridines Chemical class 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
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
• XMAQDXIHXBQZRR-UHFFFAOYSA-N 1-[5,7-di(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=CC=N1 XMAQDXIHXBQZRR-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• 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 description 2
• 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 description 2
• NLHCACXOIRURFD-UHFFFAOYSA-N 1-ethyl-3-[7-(2-methoxy-1,3-thiazol-4-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=CSC(OC)=N1 NLHCACXOIRURFD-UHFFFAOYSA-N 0.000 claims description 2
• JGTGXLYXRUZYLS-UHFFFAOYSA-N 1-ethyl-3-[7-(5-methylpyridin-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=C(C)C=N1 JGTGXLYXRUZYLS-UHFFFAOYSA-N 0.000 claims description 2
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
• 150000004677 hydrates Chemical class 0.000 claims description 2
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
• 150000003216 pyrazines Chemical group 0.000 claims description 2
• 150000003230 pyrimidines Chemical group 0.000 claims description 2
• 239000000758 substrate Substances 0.000 claims description 2
• 150000002431 hydrogen Chemical class 0.000 claims 5
• DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims 4
• 229910014585 C2-Ce Inorganic materials 0.000 claims 3
• JETJLRRENJKHBB-UHFFFAOYSA-N 1-ethyl-3-[5-[6-(2-hydroxyethyl)pyridin-3-yl]-7-pyridin-2-yl-1,3-benzothiazol-2-yl]urea Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC(CCO)=CC=2)=CC=1C1=CC=CC=N1 JETJLRRENJKHBB-UHFFFAOYSA-N 0.000 claims 2
• 101100490437 Mus musculus Acvrl1 gene Proteins 0.000 claims 2
• 235000005152 nicotinamide Nutrition 0.000 claims 2
• IHJMDGMHTJDDIS-UHFFFAOYSA-N 1-(7-cyclopropyl-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=1C1CC1 IHJMDGMHTJDDIS-UHFFFAOYSA-N 0.000 claims 1
• DQBOLZYHOONFIL-UHFFFAOYSA-N 1-[5,7-bis[4-(morpholin-4-ylmethyl)phenyl]-1,3-benzothiazol-2-yl]-3-ethylurea Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=CC(CN3CCOCC3)=CC=2)=CC=1C(C=C1)=CC=C1CN1CCOCC1 DQBOLZYHOONFIL-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
• 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
• RIRHZGBXISMLES-UHFFFAOYSA-N 1-[5-(5-cyanopyridin-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(C=NC=2)C#N)=CC=1C1=CC=CN=C1 RIRHZGBXISMLES-UHFFFAOYSA-N 0.000 claims 1
• JGZIXTLTDUKVBC-UHFFFAOYSA-N 1-[5-(6-aminopyridin-3-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)=CC=2)=CC=1C1=CC=CN=C1 JGZIXTLTDUKVBC-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
• OKNNRXRRXYQSIN-UHFFFAOYSA-N 1-[5-(6-cyanopyridin-3-yl)-7-pyridin-3-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=CN=C1 OKNNRXRRXYQSIN-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
• SBRBWCSORKMVMO-UHFFFAOYSA-N 1-[5-[6-[[bis(2-methoxyethyl)amino]methyl]pyridin-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(CN(CCOC)CCOC)=CC=2)=CC=1C1=CC=CC=N1 SBRBWCSORKMVMO-UHFFFAOYSA-N 0.000 claims 1
• JEBNMAUZFPJYOF-UHFFFAOYSA-N 1-[7-(2,4-dimethyl-1,3-thiazol-5-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=1C=1SC(C)=NC=1C JEBNMAUZFPJYOF-UHFFFAOYSA-N 0.000 claims 1
• JTCKLWFGJXXDHS-UHFFFAOYSA-N 1-[7-(2-aminopyrimidin-4-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=NC(N)=N1 JTCKLWFGJXXDHS-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
• XFVJZCWTYITJRB-UHFFFAOYSA-N 1-[7-(2-aminopyrimidin-5-yl)-5-pyridin-2-yl-1,3-benzothiazol-2-yl]-3-ethylurea Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2N=CC=CC=2)=CC=1C1=CN=C(N)N=C1 XFVJZCWTYITJRB-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
• FGUOBUOPDTXHLP-UHFFFAOYSA-N 1-[7-(3-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=NC=CC=C1C#N FGUOBUOPDTXHLP-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
• 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
• 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
• 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
• 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
• UUEQSDABILAJPW-UHFFFAOYSA-N 1-ethyl-3-(7-phenyl-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=C1 UUEQSDABILAJPW-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
• 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
• 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
• 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
• 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
• FSNBELDSQMNBIU-UHFFFAOYSA-N 1-ethyl-3-[5-[1-(2-hydroxyethyl)-2-oxopyridin-4-yl]-7-pyridin-2-yl-1,3-benzothiazol-2-yl]urea Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C2=CC(=O)N(CCO)C=C2)=CC=1C1=CC=CC=N1 FSNBELDSQMNBIU-UHFFFAOYSA-N 0.000 claims 1
• HYOAZHFLYJHNKJ-UHFFFAOYSA-N 1-ethyl-3-[5-[4-(hydroxymethyl)phenyl]-7-pyridin-3-yl-1,3-benzothiazol-2-yl]urea Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=CC(CO)=CC=2)=CC=1C1=CC=CN=C1 HYOAZHFLYJHNKJ-UHFFFAOYSA-N 0.000 claims 1
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