JP2018501279A5 - - Google Patents
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- JP2018501279A5 JP2018501279A5 JP2017535817A JP2017535817A JP2018501279A5 JP 2018501279 A5 JP2018501279 A5 JP 2018501279A5 JP 2017535817 A JP2017535817 A JP 2017535817A JP 2017535817 A JP2017535817 A JP 2017535817A JP 2018501279 A5 JP2018501279 A5 JP 2018501279A5
- Authority
- JP
- Japan
- Prior art keywords
- thiazol
- butan
- trifluoromethoxy
- benzo
- ethoxypyridin
- 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.)
- Withdrawn
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- -1 enantiomer Chemical class 0.000 claims 35
- 150000001875 compounds Chemical class 0.000 claims 18
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 13
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 12
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 10
- 125000001246 bromo group Chemical group Br* 0.000 claims 10
- 125000001309 chloro group Chemical group Cl* 0.000 claims 10
- 238000000034 method Methods 0.000 claims 9
- 125000001153 fluoro group Chemical group F* 0.000 claims 8
- 125000003652 trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims 8
- 201000010099 disease Diseases 0.000 claims 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 7
- 125000001424 substituent group Chemical group 0.000 claims 7
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 125000000950 dibromo group Chemical group Br* 0.000 claims 6
- 125000003963 dichloro group Chemical group Cl* 0.000 claims 6
- 239000008194 pharmaceutical composition Substances 0.000 claims 6
- 125000001188 haloalkyl group Chemical group 0.000 claims 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 5
- 206010016654 Fibrosis Diseases 0.000 claims 4
- 230000004761 fibrosis Effects 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 208000017169 kidney disease Diseases 0.000 claims 4
- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 claims 4
- 210000000056 organ Anatomy 0.000 claims 4
- JKTORXLUQLQJCM-UHFFFAOYSA-N 4-phosphonobutylphosphonic acid Chemical compound OP(O)(=O)CCCCP(O)(O)=O JKTORXLUQLQJCM-UHFFFAOYSA-N 0.000 claims 3
- 206010063837 Reperfusion injury Diseases 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 125000000304 alkynyl group Chemical group 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
- 230000000302 ischemic effect Effects 0.000 claims 3
- 208000031225 myocardial ischemia Diseases 0.000 claims 3
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims 2
- PQSUYGKTWSAVDQ-ZVIOFETBSA-N Aldosterone Chemical compound C([C@@]1([C@@H](C(=O)CO)CC[C@H]1[C@@H]1CC2)C=O)[C@H](O)[C@@H]1[C@]1(C)C2=CC(=O)CC1 PQSUYGKTWSAVDQ-ZVIOFETBSA-N 0.000 claims 2
- PQSUYGKTWSAVDQ-UHFFFAOYSA-N Aldosterone Natural products C1CC2C3CCC(C(=O)CO)C3(C=O)CC(O)C2C2(C)C1=CC(=O)CC2 PQSUYGKTWSAVDQ-UHFFFAOYSA-N 0.000 claims 2
- 208000001647 Renal Insufficiency Diseases 0.000 claims 2
- 208000034189 Sclerosis Diseases 0.000 claims 2
- 229960002478 aldosterone Drugs 0.000 claims 2
- 208000026106 cerebrovascular disease Diseases 0.000 claims 2
- 230000001684 chronic effect Effects 0.000 claims 2
- 208000020832 chronic kidney disease Diseases 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000004404 heteroalkyl group Chemical group 0.000 claims 2
- 208000014674 injury Diseases 0.000 claims 2
- 208000012947 ischemia reperfusion injury Diseases 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 210000003734 kidney Anatomy 0.000 claims 2
- 201000006370 kidney failure Diseases 0.000 claims 2
- 208000019423 liver disease Diseases 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 230000002685 pulmonary effect Effects 0.000 claims 2
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims 2
- 230000008733 trauma Effects 0.000 claims 2
- VQMRHTVKQMKLIJ-GOSISDBHSA-N (1R)-1-(4-ethoxypyridin-3-yl)-1-[6-(trifluoromethoxy)-7-(trifluoromethyl)-1,3-benzothiazol-2-yl]butan-1-ol Chemical compound C(C)OC1=C(C=NC=C1)[C@@](CCC)(O)C=1SC2=C(N=1)C=CC(=C2C(F)(F)F)OC(F)(F)F VQMRHTVKQMKLIJ-GOSISDBHSA-N 0.000 claims 1
- QKXJYCLWBODRIR-LJQANCHMSA-N (1R)-1-(6-bromo-1,3-benzothiazol-2-yl)-1-(4-propoxypyridin-3-yl)butan-1-ol Chemical compound BrC1=CC2=C(N=C(S2)[C@](CCC)(O)C=2C=NC=CC=2OCCC)C=C1 QKXJYCLWBODRIR-LJQANCHMSA-N 0.000 claims 1
- QKXJYCLWBODRIR-IBGZPJMESA-N (1S)-1-(6-bromo-1,3-benzothiazol-2-yl)-1-(4-propoxypyridin-3-yl)butan-1-ol Chemical compound BrC1=CC2=C(N=C(S2)[C@@](CCC)(O)C=2C=NC=CC=2OCCC)C=C1 QKXJYCLWBODRIR-IBGZPJMESA-N 0.000 claims 1
- XCAITTYJLUXNBO-UHFFFAOYSA-N (6-bromo-1,3-benzothiazol-2-yl)-(4-methoxypyridin-3-yl)methanol Chemical compound BrC1=CC2=C(N=C(S2)C(O)C=2C=NC=CC=2OC)C=C1 XCAITTYJLUXNBO-UHFFFAOYSA-N 0.000 claims 1
- GXQFDEYQSUJOQD-UHFFFAOYSA-N (7-bromo-1,3-benzothiazol-2-yl)-(4-methoxypyridin-3-yl)methanol Chemical compound BrC1=CC=CC=2N=C(SC=21)C(O)C=1C=NC=CC=1OC GXQFDEYQSUJOQD-UHFFFAOYSA-N 0.000 claims 1
- YKYIFUROKBDHCY-ONEGZZNKSA-N (e)-4-ethoxy-1,1,1-trifluorobut-3-en-2-one Chemical group CCO\C=C\C(=O)C(F)(F)F YKYIFUROKBDHCY-ONEGZZNKSA-N 0.000 claims 1
- UBQNLMHFTVEVDI-UHFFFAOYSA-N 1-(2,2-difluoro-[1,3]dioxolo[4,5-f][1,3]benzothiazol-6-yl)-1-(4-ethoxypyridin-3-yl)butan-1-ol Chemical compound FC1(OC=2C(=CC3=C(N=C(S3)C(CCC)(O)C=3C=NC=CC=3OCC)C=2)O1)F UBQNLMHFTVEVDI-UHFFFAOYSA-N 0.000 claims 1
- BDKCCXMHCXLHMC-UHFFFAOYSA-N 1-(4-ethoxypyridin-3-yl)-1-(6-fluoro-1,3-benzothiazol-2-yl)butan-1-ol Chemical compound C(C)OC1=C(C=NC=C1)C(CCC)(O)C=1SC2=C(N=1)C=CC(=C2)F BDKCCXMHCXLHMC-UHFFFAOYSA-N 0.000 claims 1
- TUDOBQHTQXQIPS-UHFFFAOYSA-N 1-(4-ethoxypyridin-3-yl)-1-(6-methoxy-1,3-benzothiazol-2-yl)butan-1-ol Chemical compound C(C)OC1=C(C=NC=C1)C(CCC)(O)C=1SC2=C(N=1)C=CC(=C2)OC TUDOBQHTQXQIPS-UHFFFAOYSA-N 0.000 claims 1
- MLJWFSSCCIWTAT-UHFFFAOYSA-N 1-(4-ethoxypyridin-3-yl)-1-(7-methoxy-1,3-benzothiazol-2-yl)butan-1-ol Chemical compound C(C)OC1=C(C=NC=C1)C(CCC)(O)C=1SC2=C(N=1)C=CC=C2OC MLJWFSSCCIWTAT-UHFFFAOYSA-N 0.000 claims 1
- BQMOGYPOEWWFMB-UHFFFAOYSA-N 1-(4-ethoxypyridin-3-yl)-1-[5-methyl-6-(trifluoromethoxy)-1,3-benzothiazol-2-yl]butan-1-ol Chemical compound CCCC(O)(C1=NC2=CC(C)=C(OC(F)(F)F)C=C2S1)C1=C(OCC)C=CN=C1 BQMOGYPOEWWFMB-UHFFFAOYSA-N 0.000 claims 1
- KKTZJPQZRATZRC-UHFFFAOYSA-N 1-(4-ethoxypyridin-3-yl)-1-[6-(4-fluorophenoxy)-1,3-benzothiazol-2-yl]butan-1-ol Chemical compound CCCC(O)(C1=NC2=CC=C(OC3=CC=C(F)C=C3)C=C2S1)C1=C(OCC)C=CN=C1 KKTZJPQZRATZRC-UHFFFAOYSA-N 0.000 claims 1
- SSIBCWOGMLAVHE-UHFFFAOYSA-N 1-(4-ethoxypyridin-3-yl)-1-[6-(trifluoromethoxy)-1,3-benzothiazol-2-yl]butan-1-ol Chemical compound CCCC(O)(C1=NC2=CC=C(OC(F)(F)F)C=C2S1)C1=C(OCC)C=CN=C1 SSIBCWOGMLAVHE-UHFFFAOYSA-N 0.000 claims 1
- GOHMCOMJBBTHFJ-UHFFFAOYSA-N 1-(4-ethoxypyridin-3-yl)-1-[6-(trifluoromethoxy)-5-(trifluoromethyl)-1,3-benzothiazol-2-yl]butan-1-ol Chemical compound CCCC(O)(C1=NC2=CC(=C(OC(F)(F)F)C=C2S1)C(F)(F)F)C1=C(OCC)C=CN=C1 GOHMCOMJBBTHFJ-UHFFFAOYSA-N 0.000 claims 1
- OQFBVICZGBQKNC-UHFFFAOYSA-N 1-(4-ethoxypyridin-3-yl)-1-[6-(trifluoromethyl)-1,3-benzothiazol-2-yl]butan-1-ol Chemical compound CCCC(O)(C1=NC2=CC=C(C=C2S1)C(F)(F)F)C1=C(OCC)C=CN=C1 OQFBVICZGBQKNC-UHFFFAOYSA-N 0.000 claims 1
- BWMDHKRVIVLVCT-UHFFFAOYSA-N 1-(4-ethoxypyridin-3-yl)-1-[7-(trifluoromethyl)-1,3-benzothiazol-2-yl]butan-1-ol Chemical compound C(C)OC1=C(C=NC=C1)C(CCC)(O)C=1SC2=C(N=1)C=CC=C2C(F)(F)F BWMDHKRVIVLVCT-UHFFFAOYSA-N 0.000 claims 1
- FVWWFBUNBKEEFY-UHFFFAOYSA-N 1-(4-ethoxypyridin-3-yl)-1-[7-methyl-6-(trifluoromethoxy)-1,3-benzothiazol-2-yl]butan-1-ol Chemical compound CCCC(O)(C1=NC2=CC=C(OC(F)(F)F)C(C)=C2S1)C1=C(OCC)C=CN=C1 FVWWFBUNBKEEFY-UHFFFAOYSA-N 0.000 claims 1
- MQKUTHOXFMOYIB-UHFFFAOYSA-N 1-(4-methoxypyridin-3-yl)-1-(6-nitro-1,3-benzothiazol-2-yl)butan-1-ol Chemical compound CCCC(O)(C1=NC2=CC=C(C=C2S1)[N+]([O-])=O)C1=C(OC)C=CN=C1 MQKUTHOXFMOYIB-UHFFFAOYSA-N 0.000 claims 1
- APXLRVXSMIFBAZ-UHFFFAOYSA-N 1-(4-propan-2-yloxypyridin-3-yl)-1-[6-(trifluoromethoxy)-1,3-benzothiazol-2-yl]butan-1-ol Chemical compound CCCC(O)(C1=NC2=CC=C(OC(F)(F)F)C=C2S1)C1=C(OC(C)C)C=CN=C1 APXLRVXSMIFBAZ-UHFFFAOYSA-N 0.000 claims 1
- QLXSZBBYIXVXIY-UHFFFAOYSA-N 1-(4-propoxypyridin-3-yl)-1-[6-(trifluoromethoxy)-1,3-benzothiazol-2-yl]butan-1-ol Chemical compound CCCOC1=C(C=NC=C1)C(O)(CCC)C1=NC2=CC=C(OC(F)(F)F)C=C2S1 QLXSZBBYIXVXIY-UHFFFAOYSA-N 0.000 claims 1
- NCFQUOMEMVXLGE-UHFFFAOYSA-N 1-(4-propoxypyridin-3-yl)-1-[6-(trifluoromethoxy)-5-(trifluoromethyl)-1,3-benzothiazol-2-yl]butan-1-ol Chemical compound C(CC)OC1=C(C=NC=C1)C(CCC)(O)C=1SC2=C(N=1)C=C(C(=C2)OC(F)(F)F)C(F)(F)F NCFQUOMEMVXLGE-UHFFFAOYSA-N 0.000 claims 1
- YZBGHVNBPKZGJV-UHFFFAOYSA-N 1-(4-propoxypyridin-3-yl)-1-[6-(trifluoromethyl)-1,3-benzothiazol-2-yl]butan-1-ol Chemical compound CCCOC1=C(C=NC=C1)C(O)(CCC)C1=NC2=CC=C(C=C2S1)C(F)(F)F YZBGHVNBPKZGJV-UHFFFAOYSA-N 0.000 claims 1
- MOODQEWKMGHVFN-UHFFFAOYSA-N 1-(5,6-dichloro-1,3-benzothiazol-2-yl)-1-(4-ethoxypyridin-3-yl)butan-1-ol Chemical compound CCCC(O)(C1=NC2=CC(Cl)=C(Cl)C=C2S1)C1=C(OCC)C=CN=C1 MOODQEWKMGHVFN-UHFFFAOYSA-N 0.000 claims 1
- OGBBBNOKLFTFOQ-UHFFFAOYSA-N 1-(6-bromo-1,3-benzothiazol-2-yl)-1-(4-ethoxypyridin-3-yl)butan-1-ol Chemical compound BrC1=CC2=C(N=C(S2)C(CCC)(O)C=2C=NC=CC=2OCC)C=C1 OGBBBNOKLFTFOQ-UHFFFAOYSA-N 0.000 claims 1
- PPMHWVNEEKBMOU-UHFFFAOYSA-N 1-(6-bromo-1,3-benzothiazol-2-yl)-1-(4-methoxypyridin-3-yl)-2-methylpropan-1-ol Chemical compound BrC1=CC2=C(N=C(S2)C(C(C)C)(O)C=2C=NC=CC=2OC)C=C1 PPMHWVNEEKBMOU-UHFFFAOYSA-N 0.000 claims 1
- OPNVYAPWECBYFD-UHFFFAOYSA-N 1-(6-bromo-1,3-benzothiazol-2-yl)-1-(4-methoxypyridin-3-yl)butan-1-ol Chemical compound CCCC(O)(C1=NC2=CC=C(Br)C=C2S1)C1=C(OC)C=CN=C1 OPNVYAPWECBYFD-UHFFFAOYSA-N 0.000 claims 1
- JZRXRBFZLFCTOC-UHFFFAOYSA-N 1-(6-bromo-1,3-benzothiazol-2-yl)-1-(5-methoxypyridin-3-yl)butan-1-ol Chemical compound BrC1=CC2=C(N=C(S2)C(CCC)(O)C=2C=NC=C(C=2)OC)C=C1 JZRXRBFZLFCTOC-UHFFFAOYSA-N 0.000 claims 1
- PVJGZALMGYQLLD-UHFFFAOYSA-N 1-(6-bromo-1,3-benzothiazol-2-yl)-1-(5-phenylpyridin-3-yl)butan-1-ol Chemical compound CCCC(O)(C1=NC2=CC=C(Br)C=C2S1)C1=CC(=CN=C1)C1=CC=CC=C1 PVJGZALMGYQLLD-UHFFFAOYSA-N 0.000 claims 1
- MGUDQSKTDZWTLE-UHFFFAOYSA-N 1-(6-bromo-1,3-benzothiazol-2-yl)-1-(5-pyridin-3-ylpyridin-3-yl)butan-1-ol Chemical compound N1=CC(=CC(=C1)C(CCC)(O)C=1SC2=C(N=1)C=CC(=C2)Br)C=1C=NC=CC=1 MGUDQSKTDZWTLE-UHFFFAOYSA-N 0.000 claims 1
- FQHREQIOHGQNHV-UHFFFAOYSA-N 1-(6-bromo-1,3-benzothiazol-2-yl)-2-methyl-1-(4-propan-2-yloxypyridin-3-yl)propan-1-ol Chemical compound BrC1=CC2=C(N=C(S2)C(C(C)C)(O)C=2C=NC=CC=2OC(C)C)C=C1 FQHREQIOHGQNHV-UHFFFAOYSA-N 0.000 claims 1
- MEBXZUBGJQOQEC-UHFFFAOYSA-N 1-(6-bromo-1,3-benzothiazol-2-yl)-2-methyl-1-(4-propan-2-ylpyridin-3-yl)propan-1-ol Chemical compound BrC1=CC2=C(N=C(S2)C(C(C)C)(O)C=2C=NC=CC=2C(C)C)C=C1 MEBXZUBGJQOQEC-UHFFFAOYSA-N 0.000 claims 1
- JZUBCTBARQBAAG-UHFFFAOYSA-N 1-(6-bromo-5,7-dichloro-1,3-benzothiazol-2-yl)-1-(4-propoxypyridin-3-yl)butan-1-ol Chemical compound CCCOC1=C(C=NC=C1)C(O)(CCC)C1=NC2=CC(Cl)=C(Br)C(Cl)=C2S1 JZUBCTBARQBAAG-UHFFFAOYSA-N 0.000 claims 1
- WOPWMOOBSKZEQR-UHFFFAOYSA-N 1-(6-chloro-1,3-benzothiazol-2-yl)-1-(4-ethoxypyridin-3-yl)butan-1-ol Chemical compound ClC1=CC2=C(N=C(S2)C(CCC)(O)C=2C=NC=CC=2OCC)C=C1 WOPWMOOBSKZEQR-UHFFFAOYSA-N 0.000 claims 1
- BPARLILDOFMHGE-UHFFFAOYSA-N 1-(6-fluoro-1,3-benzothiazol-2-yl)-1-(5-methoxypyridin-3-yl)butan-1-ol Chemical compound CCCC(O)(C1=NC2=CC=C(F)C=C2S1)C1=CC(OC)=CN=C1 BPARLILDOFMHGE-UHFFFAOYSA-N 0.000 claims 1
- UJRONZWPIFCCDB-UHFFFAOYSA-N 1-(7-bromo-1,3-benzothiazol-2-yl)-1-(4-ethoxy-5-methoxypyridin-3-yl)butan-1-ol Chemical compound BrC1=CC=CC=2N=C(SC=21)C(CCC)(O)C=1C=NC=C(C=1OCC)OC UJRONZWPIFCCDB-UHFFFAOYSA-N 0.000 claims 1
- CSOQPYMGTWPROA-UHFFFAOYSA-N 1-(7-bromo-1,3-benzothiazol-2-yl)-1-(4-ethoxypyridin-3-yl)-2-methylpropan-1-ol Chemical compound CCOC1=C(C=NC=C1)C(O)(C(C)C)C1=NC2=CC=CC(Br)=C2S1 CSOQPYMGTWPROA-UHFFFAOYSA-N 0.000 claims 1
- YJUNHNYZWIFNBB-UHFFFAOYSA-N 1-(7-bromo-1,3-benzothiazol-2-yl)-1-(4-propan-2-ylpyridin-3-yl)butan-1-ol Chemical compound CCCC(O)(C1=NC2=CC=CC(Br)=C2S1)C1=C(C=CN=C1)C(C)C YJUNHNYZWIFNBB-UHFFFAOYSA-N 0.000 claims 1
- DFOLWANDTZNBID-UHFFFAOYSA-N 1-(7-bromo-1,3-benzothiazol-2-yl)-1-pyridin-3-ylbutan-1-ol Chemical compound CCCC(O)(C1=NC2=CC=CC(Br)=C2S1)C1=CC=CN=C1 DFOLWANDTZNBID-UHFFFAOYSA-N 0.000 claims 1
- YXLJGAJLIRAREP-UHFFFAOYSA-N 1-(7-bromo-1,3-benzothiazol-2-yl)-2-methyl-1-(4-propan-2-yloxypyridin-3-yl)propan-1-ol Chemical compound CC(C)OC1=C(C=NC=C1)C(O)(C(C)C)C1=NC2=CC=CC(Br)=C2S1 YXLJGAJLIRAREP-UHFFFAOYSA-N 0.000 claims 1
- RIJSVCKTYADKMM-UHFFFAOYSA-N 1-(7-bromo-1,3-benzothiazol-2-yl)-2-methyl-1-(4-propan-2-ylpyridin-3-yl)propan-1-ol Chemical compound BrC1=CC=CC=2N=C(SC=21)C(C(C)C)(O)C=1C=NC=CC=1C(C)C RIJSVCKTYADKMM-UHFFFAOYSA-N 0.000 claims 1
- NVFGGSVDGGAYRE-UHFFFAOYSA-N 1-(7-chloro-1,3-benzothiazol-2-yl)-1-(4-ethoxypyridin-3-yl)butan-1-ol Chemical compound ClC1=CC=CC=2N=C(SC=21)C(CCC)(O)C=1C=NC=CC=1OCC NVFGGSVDGGAYRE-UHFFFAOYSA-N 0.000 claims 1
- DCOCAURWIJSQSX-UHFFFAOYSA-N 1-[5,6-bis(trifluoromethoxy)-1,3-benzothiazol-2-yl]-1-(4-ethoxypyridin-3-yl)butan-1-ol Chemical compound CCCC(O)(C1=NC2=CC(OC(F)(F)F)=C(OC(F)(F)F)C=C2S1)C1=C(OCC)C=CN=C1 DCOCAURWIJSQSX-UHFFFAOYSA-N 0.000 claims 1
- BZUGZAFKIYOWAF-UHFFFAOYSA-N 1-[5,7-dichloro-6-(trifluoromethoxy)-1,3-benzothiazol-2-yl]-1-(4-ethoxypyridin-3-yl)butan-1-ol Chemical compound CCCC(O)(C1=NC2=CC(Cl)=C(OC(F)(F)F)C(Cl)=C2S1)C1=C(OCC)C=CN=C1 BZUGZAFKIYOWAF-UHFFFAOYSA-N 0.000 claims 1
- WRTQCXFAXUOWHG-UHFFFAOYSA-N 1-[5,7-difluoro-6-(trifluoromethoxy)-1,3-benzothiazol-2-yl]-1-(4-ethoxypyridin-3-yl)butan-1-ol Chemical compound CCCC(O)(C1=NC2=CC(F)=C(OC(F)(F)F)C(F)=C2S1)C1=C(OCC)C=CN=C1 WRTQCXFAXUOWHG-UHFFFAOYSA-N 0.000 claims 1
- YWXJGNNUFDKAIT-UHFFFAOYSA-N 1-[5-[di(propan-2-yl)amino]-1,3-benzothiazol-2-yl]-1-(5-methoxypyridin-3-yl)butan-1-ol Chemical compound CCCC(O)(C1=NC2=CC(=CC=C2S1)N(C(C)C)C(C)C)C1=CC(OC)=CN=C1 YWXJGNNUFDKAIT-UHFFFAOYSA-N 0.000 claims 1
- YDOCTUOCXVMHTJ-UHFFFAOYSA-N 1-[5-bromo-6-(trifluoromethoxy)-1,3-benzothiazol-2-yl]-1-(4-ethoxypyridin-3-yl)butan-1-ol Chemical compound CCCC(O)(C1=NC2=CC(Br)=C(OC(F)(F)F)C=C2S1)C1=C(OCC)C=CN=C1 YDOCTUOCXVMHTJ-UHFFFAOYSA-N 0.000 claims 1
- NAGBEJBDCPSAFU-UHFFFAOYSA-N 1-[5-bromo-6-(trifluoromethoxy)-1,3-benzothiazol-2-yl]-1-(4-propoxypyridin-3-yl)butan-1-ol Chemical compound CCCOC1=C(C=NC=C1)C(O)(CCC)C1=NC2=CC(Br)=C(OC(F)(F)F)C=C2S1 NAGBEJBDCPSAFU-UHFFFAOYSA-N 0.000 claims 1
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- QRPTWSRDXFIKFC-UHFFFAOYSA-N 1-[5-chloro-6-(trifluoromethoxy)-1,3-benzothiazol-2-yl]-1-(4-ethoxypyridin-3-yl)butan-1-ol Chemical compound CCCC(O)(C1=NC2=CC(Cl)=C(OC(F)(F)F)C=C2S1)C1=C(OCC)C=CN=C1 QRPTWSRDXFIKFC-UHFFFAOYSA-N 0.000 claims 1
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2015
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- 2015-12-29 AU AU2015374231A patent/AU2015374231B2/en not_active Ceased
- 2015-12-29 EP EP15876137.9A patent/EP3240778A4/en not_active Withdrawn
- 2015-12-29 CN CN201580071622.6A patent/CN107531631B/zh not_active Expired - Fee Related
- 2015-12-29 WO PCT/US2015/067801 patent/WO2016109492A1/en not_active Ceased
- 2015-12-29 US US15/540,592 patent/US10287282B2/en active Active
- 2015-12-29 JP JP2017535817A patent/JP2018501279A/ja not_active Withdrawn
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2017
- 2017-06-14 IL IL252904A patent/IL252904B/en active IP Right Grant
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2019
- 2019-04-30 US US16/399,888 patent/US10851095B2/en not_active Expired - Fee Related
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2020
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- 2020-11-11 JP JP2020188252A patent/JP7140813B2/ja active Active
- 2020-11-23 US US17/101,753 patent/US11434234B2/en active Active
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2021
- 2021-03-25 IL IL281825A patent/IL281825A/en unknown