JP2017141224A5 - - Google Patents
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- Publication number
- JP2017141224A5 JP2017141224A5 JP2017022803A JP2017022803A JP2017141224A5 JP 2017141224 A5 JP2017141224 A5 JP 2017141224A5 JP 2017022803 A JP2017022803 A JP 2017022803A JP 2017022803 A JP2017022803 A JP 2017022803A JP 2017141224 A5 JP2017141224 A5 JP 2017141224A5
- 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
Links
- 125000000217 alkyl group Chemical group 0.000 claims 23
- 125000005843 halogen group Chemical group 0.000 claims 22
- -1 4-chloro-2-fluorophenyl Chemical group 0.000 claims 18
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 15
- 125000003545 alkoxy group Chemical group 0.000 claims 14
- 239000008194 pharmaceutical composition Substances 0.000 claims 13
- 125000001424 substituent group Chemical group 0.000 claims 9
- 125000003277 amino group Chemical group 0.000 claims 7
- 150000001875 compounds Chemical class 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 125000004104 aryloxy group Chemical group 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 201000008827 tuberculosis Diseases 0.000 claims 3
- 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
- SRKPEMSPDXGKEC-OZAJXLCCSA-N C1CC(=O)NC2=C(C=CC(=C21)OC[C@]3(CCN(C[C@H]3CCOC(=O)O)C4=C(C=C(C=C4F)Cl)F)O)F Chemical compound C1CC(=O)NC2=C(C=CC(=C21)OC[C@]3(CCN(C[C@H]3CCOC(=O)O)C4=C(C=C(C=C4F)Cl)F)O)F SRKPEMSPDXGKEC-OZAJXLCCSA-N 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
- 125000002252 acyl group Chemical group 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 238000003745 diagnosis Methods 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 230000000069 prophylactic effect Effects 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- 0 *N(C(CC1)=O)c2c1cccc2 Chemical compound *N(C(CC1)=O)c2c1cccc2 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2016023873 | 2016-02-10 | ||
| JP2016023873 | 2016-02-10 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017141224A JP2017141224A (ja) | 2017-08-17 |
| JP2017141224A5 true JP2017141224A5 (enExample) | 2020-02-27 |
| JP6976691B2 JP6976691B2 (ja) | 2021-12-08 |
Family
ID=59627082
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017022803A Active JP6976691B2 (ja) | 2016-02-10 | 2017-02-10 | 医薬組成物 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP6976691B2 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0812648D0 (en) * | 2008-07-10 | 2008-08-20 | Prosidion Ltd | Compounds |
-
2017
- 2017-02-10 JP JP2017022803A patent/JP6976691B2/ja active Active
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