JP2017525697A5 - - Google Patents
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- Publication number
- JP2017525697A5 JP2017525697A5 JP2017507903A JP2017507903A JP2017525697A5 JP 2017525697 A5 JP2017525697 A5 JP 2017525697A5 JP 2017507903 A JP2017507903 A JP 2017507903A JP 2017507903 A JP2017507903 A JP 2017507903A JP 2017525697 A5 JP2017525697 A5 JP 2017525697A5
- Authority
- JP
- Japan
- Prior art keywords
- fluoro
- methoxy
- chloro
- fluorophenyl
- hydroxypiperidin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- -1 4-Chloro-2-fluorophenyl Chemical group 0.000 claims description 65
- 125000000217 alkyl group Chemical group 0.000 claims description 48
- 125000005843 halogen group Chemical group 0.000 claims description 44
- 125000003545 alkoxy group Chemical group 0.000 claims description 28
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 27
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 18
- 125000003277 amino group Chemical group 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000005493 quinolyl group Chemical group 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000004043 oxo group Chemical group O=* 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- PNKMABCRDORNBA-UHFFFAOYSA-N BrC1=CC(=C(C=C1)N1CCC(CC1)(O)COC1=C2CCC(NC2=C(C(=C1)F)F)=O)F Chemical compound BrC1=CC(=C(C=C1)N1CCC(CC1)(O)COC1=C2CCC(NC2=C(C(=C1)F)F)=O)F PNKMABCRDORNBA-UHFFFAOYSA-N 0.000 claims 2
- UKOJXJOKMBFYSG-TZIWHRDSSA-N BrC1=CC(=C(C=C1)N1C[C@H]([C@](CC1)(O)COC1=C2CCC(NC2=CC=C1)=O)O)F Chemical compound BrC1=CC(=C(C=C1)N1C[C@H]([C@](CC1)(O)COC1=C2CCC(NC2=CC=C1)=O)O)F UKOJXJOKMBFYSG-TZIWHRDSSA-N 0.000 claims 2
- KACCWIRHKUQZGN-HYBUGGRVSA-N BrC=1C(=NC2=CC=C(C=C2C=1)Cl)N1C[C@H]([C@](CC1)(O)COC1=C2CCC(NC2=C(C=C1)F)=O)O Chemical compound BrC=1C(=NC2=CC=C(C=C2C=1)Cl)N1C[C@H]([C@](CC1)(O)COC1=C2CCC(NC2=C(C=C1)F)=O)O KACCWIRHKUQZGN-HYBUGGRVSA-N 0.000 claims 2
- YSNFUXGRTDAYBG-NFBKMPQASA-N C(C)(=O)O[C@@H]1CN(CC[C@@]1(O)COC1=C2CCC(NC2=C(C=C1)F)=O)C1=C(C=C(C=C1)Cl)F Chemical compound C(C)(=O)O[C@@H]1CN(CC[C@@]1(O)COC1=C2CCC(NC2=C(C=C1)F)=O)C1=C(C=C(C=C1)Cl)F YSNFUXGRTDAYBG-NFBKMPQASA-N 0.000 claims 2
- SJYQNQNIDJQREE-UHFFFAOYSA-N C(C)OC1=CC(=C(C=C1)N1CCC(CC1)(O)COC1=C2CCC(NC2=C(C=C1)F)=O)F Chemical compound C(C)OC1=CC(=C(C=C1)N1CCC(CC1)(O)COC1=C2CCC(NC2=C(C=C1)F)=O)F SJYQNQNIDJQREE-UHFFFAOYSA-N 0.000 claims 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 2
- VWJBVSROHZREFF-UHFFFAOYSA-N ClC1=C(C=C(C(=C1)Cl)F)N1CCC(CC1)(O)COC1=C2CCC(NC2=C(C(=C1)F)C)=O Chemical compound ClC1=C(C=C(C(=C1)Cl)F)N1CCC(CC1)(O)COC1=C2CCC(NC2=C(C(=C1)F)C)=O VWJBVSROHZREFF-UHFFFAOYSA-N 0.000 claims 2
- AOKOIPQQLYQLFH-UHFFFAOYSA-N ClC1=CC(=C(C(=C1)F)N1CCC(CC1)(O)CCC1=C2CCC(NC2=C(C=C1)F)=O)F Chemical compound ClC1=CC(=C(C(=C1)F)N1CCC(CC1)(O)CCC1=C2CCC(NC2=C(C=C1)F)=O)F AOKOIPQQLYQLFH-UHFFFAOYSA-N 0.000 claims 2
- CJEKLPZVOGHISH-UWJYYQICSA-N ClC1=CC(=C(C(=C1)F)N1C[C@@H]([C@@](CC1)(O)COC1=C2CCC(NC2=C(C=C1)F)=O)F)F Chemical compound ClC1=CC(=C(C(=C1)F)N1C[C@@H]([C@@](CC1)(O)COC1=C2CCC(NC2=C(C=C1)F)=O)F)F CJEKLPZVOGHISH-UWJYYQICSA-N 0.000 claims 2
- CJEKLPZVOGHISH-LAUBAEHRSA-N ClC1=CC(=C(C(=C1)F)N1C[C@@H]([C@](CC1)(O)COC1=C2CCC(NC2=C(C=C1)F)=O)F)F Chemical compound ClC1=CC(=C(C(=C1)F)N1C[C@@H]([C@](CC1)(O)COC1=C2CCC(NC2=C(C=C1)F)=O)F)F CJEKLPZVOGHISH-LAUBAEHRSA-N 0.000 claims 2
- XZISSTDXPBUCJA-LAUBAEHRSA-N ClC1=CC(=C(C(=C1)F)N1C[C@@H]([C@](CC1)(O)COC1=C2CCC(NC2=C(C=C1)F)=O)O)F Chemical compound ClC1=CC(=C(C(=C1)F)N1C[C@@H]([C@](CC1)(O)COC1=C2CCC(NC2=C(C=C1)F)=O)O)F XZISSTDXPBUCJA-LAUBAEHRSA-N 0.000 claims 2
- CJEKLPZVOGHISH-UTKZUKDTSA-N ClC1=CC(=C(C(=C1)F)N1C[C@H]([C@@](CC1)(O)COC1=C2CCC(NC2=C(C=C1)F)=O)F)F Chemical compound ClC1=CC(=C(C(=C1)F)N1C[C@H]([C@@](CC1)(O)COC1=C2CCC(NC2=C(C=C1)F)=O)F)F CJEKLPZVOGHISH-UTKZUKDTSA-N 0.000 claims 2
- CJEKLPZVOGHISH-DYESRHJHSA-N ClC1=CC(=C(C(=C1)F)N1C[C@H]([C@](CC1)(O)COC1=C2CCC(NC2=C(C=C1)F)=O)F)F Chemical compound ClC1=CC(=C(C(=C1)F)N1C[C@H]([C@](CC1)(O)COC1=C2CCC(NC2=C(C=C1)F)=O)F)F CJEKLPZVOGHISH-DYESRHJHSA-N 0.000 claims 2
- XZISSTDXPBUCJA-DYESRHJHSA-N ClC1=CC(=C(C(=C1)F)N1C[C@H]([C@](CC1)(O)COC1=C2CCC(NC2=C(C=C1)F)=O)O)F Chemical compound ClC1=CC(=C(C(=C1)F)N1C[C@H]([C@](CC1)(O)COC1=C2CCC(NC2=C(C=C1)F)=O)O)F XZISSTDXPBUCJA-DYESRHJHSA-N 0.000 claims 2
- SJYAXBUQMKWWFS-UHFFFAOYSA-N ClC1=CC(=C(C=C1)N1CCC(CC1)(O)COC1=C2C=CC(NC2=CC=C1)=O)F Chemical compound ClC1=CC(=C(C=C1)N1CCC(CC1)(O)COC1=C2C=CC(NC2=CC=C1)=O)F SJYAXBUQMKWWFS-UHFFFAOYSA-N 0.000 claims 2
- ITGMMAFQJUQFHS-UHFFFAOYSA-N ClC1=CC(=C(C=C1)N1CCC(CC1)(O)COC1=C2CCC(NC2=C(C=C1)F)=O)F Chemical compound ClC1=CC(=C(C=C1)N1CCC(CC1)(O)COC1=C2CCC(NC2=C(C=C1)F)=O)F ITGMMAFQJUQFHS-UHFFFAOYSA-N 0.000 claims 2
- DHURUPBJOVKMAG-UHFFFAOYSA-N ClC1=CC(=C(C=C1)N1CCC(CC1)(O)COC1=C2CCC(NC2=CC(=C1)F)=O)F Chemical compound ClC1=CC(=C(C=C1)N1CCC(CC1)(O)COC1=C2CCC(NC2=CC(=C1)F)=O)F DHURUPBJOVKMAG-UHFFFAOYSA-N 0.000 claims 2
- YCUYBFIXAQWMCZ-UHFFFAOYSA-N ClC1=CC(=C(C=C1)N1CCC(CC1)(O)CSC1=C2CCC(NC2=C(C=C1)F)=O)F Chemical compound ClC1=CC(=C(C=C1)N1CCC(CC1)(O)CSC1=C2CCC(NC2=C(C=C1)F)=O)F YCUYBFIXAQWMCZ-UHFFFAOYSA-N 0.000 claims 2
- ILHQSBVTSSNISF-BVYCBKJFSA-N ClC1=CC(=C(C=C1)[C@]1(C[C@H]([C@](CC1)(O)COC1=C2CCC(NC2=C(C=C1)F)=O)O)O)F Chemical compound ClC1=CC(=C(C=C1)[C@]1(C[C@H]([C@](CC1)(O)COC1=C2CCC(NC2=C(C=C1)F)=O)O)O)F ILHQSBVTSSNISF-BVYCBKJFSA-N 0.000 claims 2
- YRZRZJKDBAJOPE-UHFFFAOYSA-N ClC1=CC=C(C=C1)N1CCC(CC1)(O)COC1=C2CCC(NC2=C(C=C1)F)=O Chemical compound ClC1=CC=C(C=C1)N1CCC(CC1)(O)COC1=C2CCC(NC2=C(C=C1)F)=O YRZRZJKDBAJOPE-UHFFFAOYSA-N 0.000 claims 2
- HLGNPDZREPJBOZ-UHFFFAOYSA-N ClC=1C(=CC(=C2CCC(NC=12)=O)OCC1(CCN(CC1)C1=C(C=C(C=C1F)F)F)O)F Chemical compound ClC=1C(=CC(=C2CCC(NC=12)=O)OCC1(CCN(CC1)C1=C(C=C(C=C1F)F)F)O)F HLGNPDZREPJBOZ-UHFFFAOYSA-N 0.000 claims 2
- JEDCEAVJJFLIBQ-UHFFFAOYSA-N ClC=1C(=NC=C(C=1)Cl)N1CCC(CC1)(F)COC1=C2CCC(NC2=C(C=C1)F)=O Chemical compound ClC=1C(=NC=C(C=1)Cl)N1CCC(CC1)(F)COC1=C2CCC(NC2=C(C=C1)F)=O JEDCEAVJJFLIBQ-UHFFFAOYSA-N 0.000 claims 2
- PRLGUXQPJMIARM-UHFFFAOYSA-N ClC=1C(=NC=C(C=1)Cl)N1CCC(CC1)(O)CNC1=C2CCC(NC2=C(C=C1)F)=O Chemical compound ClC=1C(=NC=C(C=1)Cl)N1CCC(CC1)(O)CNC1=C2CCC(NC2=C(C=C1)F)=O PRLGUXQPJMIARM-UHFFFAOYSA-N 0.000 claims 2
- WJYKQMYNUKMOJG-UHFFFAOYSA-N ClC=1C(=NC=C(C=1)Cl)N1CCC(CC1)COC1=C2CCC(NC2=C(C=C1)F)=O Chemical compound ClC=1C(=NC=C(C=1)Cl)N1CCC(CC1)COC1=C2CCC(NC2=C(C=C1)F)=O WJYKQMYNUKMOJG-UHFFFAOYSA-N 0.000 claims 2
- XYOIGTKIPNTGOU-JXFKEZNVSA-N ClC=1C(=NC=C(C=1)Cl)N1C[C@@H]([C@@](CC1)(O)COC1=C2CCC(NC2=C(C=C1)F)=O)O Chemical compound ClC=1C(=NC=C(C=1)Cl)N1C[C@@H]([C@@](CC1)(O)COC1=C2CCC(NC2=C(C=C1)F)=O)O XYOIGTKIPNTGOU-JXFKEZNVSA-N 0.000 claims 2
- XYOIGTKIPNTGOU-OXQOHEQNSA-N ClC=1C(=NC=C(C=1)Cl)N1C[C@H]([C@](CC1)(O)COC1=C2CCC(NC2=C(C=C1)F)=O)O Chemical compound ClC=1C(=NC=C(C=1)Cl)N1C[C@H]([C@](CC1)(O)COC1=C2CCC(NC2=C(C=C1)F)=O)O XYOIGTKIPNTGOU-OXQOHEQNSA-N 0.000 claims 2
- RLTYAGFJTBFSOM-UHFFFAOYSA-N ClC=1C=CC(=C2CCC(NC=12)=O)OCC1(CCN(CC1)C1=C(C=C(C(=C1)OCCOC)Cl)F)O Chemical compound ClC=1C=CC(=C2CCC(NC=12)=O)OCC1(CCN(CC1)C1=C(C=C(C(=C1)OCCOC)Cl)F)O RLTYAGFJTBFSOM-UHFFFAOYSA-N 0.000 claims 2
- XZOPYRCRTAXGRQ-UHFFFAOYSA-N ClC=1C=CC(=C2CCC(NC=12)=O)OCC1(CCN(CC1)C1=C(C=C(C=C1F)Cl)F)O Chemical compound ClC=1C=CC(=C2CCC(NC=12)=O)OCC1(CCN(CC1)C1=C(C=C(C=C1F)Cl)F)O XZOPYRCRTAXGRQ-UHFFFAOYSA-N 0.000 claims 2
- XHTDXDGZNQMAPA-UHFFFAOYSA-N ClC=1C=CC(=C2CCC(NC=12)=O)OCC1(CCN(CC1)C1=NC=C(C=C1Cl)Cl)O Chemical compound ClC=1C=CC(=C2CCC(NC=12)=O)OCC1(CCN(CC1)C1=NC=C(C=C1Cl)Cl)O XHTDXDGZNQMAPA-UHFFFAOYSA-N 0.000 claims 2
- IOUGAMRYVMXZHC-UHFFFAOYSA-N FC=1C=CC(=C2CCC(NC=12)=O)OCC1(CCN(CC1)C1=C(C=C(C=C1)OCC1=CC=C(C=C1)OC(F)(F)F)F)O Chemical compound FC=1C=CC(=C2CCC(NC=12)=O)OCC1(CCN(CC1)C1=C(C=C(C=C1)OCC1=CC=C(C=C1)OC(F)(F)F)F)O IOUGAMRYVMXZHC-UHFFFAOYSA-N 0.000 claims 2
- OKDBWDVZZXLVGR-UHFFFAOYSA-N NC1(CCN(CC1)C1=C(C=C(C=C1)Cl)F)COC1=C2C=CC(NC2=C(C=C1)Cl)=O Chemical compound NC1(CCN(CC1)C1=C(C=C(C=C1)Cl)F)COC1=C2C=CC(NC2=C(C=C1)Cl)=O OKDBWDVZZXLVGR-UHFFFAOYSA-N 0.000 claims 2
- XXYCCPVXWLCUTP-UHFFFAOYSA-N NC1(CCN(CC1)C1=C(C=C(C=C1)Cl)F)COC1=C2CCC(NC2=C(C=C1)Cl)=O Chemical compound NC1(CCN(CC1)C1=C(C=C(C=C1)Cl)F)COC1=C2CCC(NC2=C(C=C1)Cl)=O XXYCCPVXWLCUTP-UHFFFAOYSA-N 0.000 claims 2
- RDQYZGCHTOJTTN-UHFFFAOYSA-N NC1(CCN(CC1)C1=NC=C(C=C1Cl)Cl)COC1=C2CCC(NC2=C(C=C1)F)=O Chemical compound NC1(CCN(CC1)C1=NC=C(C=C1Cl)Cl)COC1=C2CCC(NC2=C(C=C1)F)=O RDQYZGCHTOJTTN-UHFFFAOYSA-N 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 15
- 229910052731 fluorine Inorganic materials 0.000 description 15
- 239000011737 fluorine Substances 0.000 description 15
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 125000005090 alkenylcarbonyl group Chemical group 0.000 description 2
- 125000005133 alkynyloxy group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 1
- 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 description 1
- 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 description 1
- MWFMGBPGAXYFAR-UHFFFAOYSA-N 2-hydroxy-2-methylpropanenitrile Chemical compound CC(C)(O)C#N MWFMGBPGAXYFAR-UHFFFAOYSA-N 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 0 CC*C(C(C)*)(C1(CC*(C)CC1)O)NC Chemical compound CC*C(C(C)*)(C1(CC*(C)CC1)O)NC 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 description 1
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- 125000005290 ethynyloxy group Chemical group C(#C)O* 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2014174528 | 2014-08-28 | ||
| JP2014174528 | 2014-08-28 | ||
| PCT/JP2015/004371 WO2016031255A1 (en) | 2014-08-28 | 2015-08-28 | Heterobicyclic compounds and their use for the treatment of tuberculosis |
Publications (3)
| Publication Number | Publication Date |
|---|---|
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| TWI687409B (zh) * | 2014-08-28 | 2020-03-11 | 日商大塚製藥股份有限公司 | 稠合雜環化合物 |
| EP3421454B9 (en) * | 2016-02-26 | 2023-08-09 | Otsuka Pharmaceutical Co., Ltd. | Piperidine derivative |
| WO2019239382A1 (en) | 2018-06-15 | 2019-12-19 | Cadila Healthcare Limited | Condensed azaheteroaryl compounds having antibacterial activity against tuberculosis bacteria |
| JP2023085582A (ja) * | 2020-05-11 | 2023-06-21 | 大塚製薬株式会社 | ジヒドロキノリノン化合物の共結晶 |
| KR20220022877A (ko) * | 2020-08-19 | 2022-02-28 | 주식회사 미토이뮨테라퓨틱스 | Ｍabc-R 감염에 의한 병적 염증 치료제로서의 미토콘드리아 표적 항산화제 |
| CN116102537B (zh) * | 2021-11-10 | 2024-10-01 | 四川大学 | 一种喹啉酮类衍生物及其制备方法和用途 |
| CN116589448B (zh) * | 2023-04-24 | 2025-10-28 | 西南交通大学 | 一种3,4-二氢喹啉酮衍生物及其应用 |
| WO2025183016A1 (ja) * | 2024-02-26 | 2025-09-04 | 大塚製薬株式会社 | Ｑｕａｂｏｄｅｐｉｓｔａｔ含有組成物 |
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| JP2608788B2 (ja) * | 1988-10-31 | 1997-05-14 | 大塚製薬 株式会社 | 精神分裂病治療剤 |
| US5668127A (en) | 1995-06-26 | 1997-09-16 | Pathogenesis Corporation | Nitroimidazole antibacterial compounds and methods of use thereof |
| AR041198A1 (es) | 2002-10-11 | 2005-05-04 | Otsuka Pharma Co Ltd | Compuesto 2,3-dihidro-6-nitroimidazo[2,1-b] oxaxol, y composiciones farmaceuticas que lo contienen |
| GB0319150D0 (en) * | 2003-08-14 | 2003-09-17 | Glaxo Group Ltd | Novel compounds |
| PT1678185E (pt) | 2003-10-31 | 2009-01-13 | Otsuka Pharma Co Ltd | Compostos 2,3-di-hidro-6-nitroimidazo[2,1-b]oxazole para o tratamento da tuberculose |
| JP4761756B2 (ja) | 2003-10-31 | 2011-08-31 | 大塚製薬株式会社 | ２，３−ジヒドロイミダゾ［２，１−ｂ］オキサゾ−ル化合物 |
| CN100497345C (zh) * | 2003-10-31 | 2009-06-10 | 大塚制药株式会社 | 治疗结核病的2,3-二氢-6-硝基咪唑并[2,1-b]唑化合物 |
| LT2502911T (lt) * | 2004-06-24 | 2017-09-11 | Vertex Pharmaceuticals Incorporated | Atp surišančios kasetės transporterių moduliatoriai |
| EP2520567A3 (en) | 2006-02-23 | 2012-12-12 | Shionogi & Co., Ltd. | Nitrogen-containing heterocycle derivatives substituted with cyclic group |
| GB0812648D0 (en) * | 2008-07-10 | 2008-08-20 | Prosidion Ltd | Compounds |
| WO2010045987A1 (en) * | 2008-10-23 | 2010-04-29 | Glaxo Group Limited | Substituted (aza) -1-methyl-1h-quin0lin-2-0nes as antibacterials |
| BR112012002214B1 (pt) | 2009-07-31 | 2022-01-25 | Global Alliance For Tb Drug Development | Análogos de nitroimidazooxazina e nitroimidazooxazol, seus usos e composição farmacêutica |
| US9051333B2 (en) | 2011-04-15 | 2015-06-09 | Otsuka Pharmaceutical Co., Ltd. | 6,7-dihydroimidazo [2,1-b] [1,3]oxazine bactericides |
| TWI687409B (zh) * | 2014-08-28 | 2020-03-11 | 日商大塚製藥股份有限公司 | 稠合雜環化合物 |
| EP3421454B9 (en) * | 2016-02-26 | 2023-08-09 | Otsuka Pharmaceutical Co., Ltd. | Piperidine derivative |
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