JP2017524006A5 - - Google Patents
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- Publication number
- JP2017524006A5 JP2017524006A5 JP2017506993A JP2017506993A JP2017524006A5 JP 2017524006 A5 JP2017524006 A5 JP 2017524006A5 JP 2017506993 A JP2017506993 A JP 2017506993A JP 2017506993 A JP2017506993 A JP 2017506993A JP 2017524006 A5 JP2017524006 A5 JP 2017524006A5
- Authority
- JP
- Japan
- Prior art keywords
- oxo
- fluoropyridin
- formula
- trifluoroethylimino
- dimethyl
- 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
- -1 cyano, methyl Chemical group 0.000 claims 29
- 150000001875 compounds Chemical class 0.000 claims 25
- 229910052736 halogen Inorganic materials 0.000 claims 10
- 150000002367 halogens Chemical class 0.000 claims 7
- 102000013455 Amyloid beta-Peptides Human genes 0.000 claims 6
- 108010090849 Amyloid beta-Peptides Proteins 0.000 claims 6
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 5
- 125000001424 substituent group Chemical group 0.000 claims 4
- 208000037259 Amyloid Plaque Diseases 0.000 claims 3
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 230000001225 therapeutic effect Effects 0.000 claims 3
- IQNFOMCQCZMGLC-HJFSHJIFSA-N (1R,5R)-5-[3-fluoro-6-(1H-pyrazol-5-yl)pyridin-2-yl]-2,5-dimethyl-1-oxo-1-(2,2,2-trifluoroethylimino)-6H-1,2,4-thiadiazin-3-amine Chemical compound FC=1C(=NC(=CC=1)C1=CC=NN1)[C@]1(N=C(N([S@@](C1)(=NCC(F)(F)F)=O)C)N)C IQNFOMCQCZMGLC-HJFSHJIFSA-N 0.000 claims 2
- ZVOYHRVXWDOKFR-PEGYKEAPSA-N (1R,5R)-5-[6-(5-chlorothiophen-2-yl)-3-fluoropyridin-2-yl]-2,5-dimethyl-1-oxo-1-(2,2,2-trifluoroethylimino)-6H-1,2,4-thiadiazin-3-amine Chemical compound ClC1=CC=C(S1)C1=CC=C(C(=N1)[C@]1(N=C(N([S@@](C1)(=NCC(F)(F)F)=O)C)N)C)F ZVOYHRVXWDOKFR-PEGYKEAPSA-N 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- ZBTYNHZFTNANRV-BUBHHJDNSA-N BrC1=CC=C(C(=N1)[C@]1(N=C(N([S@](C1)(=NCC(F)(F)F)=O)C)N)C)F Chemical compound BrC1=CC=C(C(=N1)[C@]1(N=C(N([S@](C1)(=NCC(F)(F)F)=O)C)N)C)F ZBTYNHZFTNANRV-BUBHHJDNSA-N 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 208000037765 diseases and disorders Diseases 0.000 claims 2
- 238000011321 prophylaxis Methods 0.000 claims 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims 2
- JBXOHZKYCIIYIA-GNDHZGTQSA-N BrC1=CC=C(C(=N1)[C@]1(N=C(N(S(C1)(=O)=NC)CC(F)(F)F)N)C)F Chemical compound BrC1=CC=C(C(=N1)[C@]1(N=C(N(S(C1)(=O)=NC)CC(F)(F)F)N)C)F JBXOHZKYCIIYIA-GNDHZGTQSA-N 0.000 claims 1
- ZBTYNHZFTNANRV-APXPCNQMSA-N BrC1=CC=C(C(=N1)[C@]1(N=C(N([S@@](C1)(=NCC(F)(F)F)=O)C)N)C)F Chemical compound BrC1=CC=C(C(=N1)[C@]1(N=C(N([S@@](C1)(=NCC(F)(F)F)=O)C)N)C)F ZBTYNHZFTNANRV-APXPCNQMSA-N 0.000 claims 1
- NUVYICOKNIIFEN-JTHIVGNPSA-N N-[6-[(1R,5R)-3-amino-2,5-dimethyl-1-oxo-1-(2,2,2-trifluoroethylimino)-6H-1,2,4-thiadiazin-5-yl]-5-fluoropyridin-2-yl]-5-but-2-ynoxypyrazine-2-carboxamide Chemical compound NC=1N([S@@](C[C@@](N=1)(C)C1=C(C=CC(=N1)NC(=O)C1=NC=C(N=C1)OCC#CC)F)(=NCC(F)(F)F)=O)C NUVYICOKNIIFEN-JTHIVGNPSA-N 0.000 claims 1
- CUQYOKPNIRBTAZ-HSVJZKSBSA-N N-[6-[(1R,5R)-3-amino-2,5-dimethyl-1-oxo-1-(2,2,2-trifluoroethylimino)-6H-1,2,4-thiadiazin-5-yl]-5-fluoropyridin-2-yl]-5-cyano-3-methylpyridine-2-carboxamide Chemical compound NC=1N([S@@](C[C@@](N=1)(C)C1=C(C=CC(=N1)NC(=O)C1=NC=C(C=C1C)C#N)F)(=NCC(F)(F)F)=O)C CUQYOKPNIRBTAZ-HSVJZKSBSA-N 0.000 claims 1
- MBZBTDINMMUJLX-USXNREEHSA-N N-[6-[(1R,5R)-3-amino-2,5-dimethyl-1-oxo-1-(2,2,2-trifluoroethylimino)-6H-1,2,4-thiadiazin-5-yl]-5-fluoropyridin-2-yl]-5-cyanopyridine-2-carboxamide Chemical compound NC=1N([S@@](C[C@@](N=1)(C)C1=C(C=CC(=N1)NC(=O)C1=NC=C(C=C1)C#N)F)(=NCC(F)(F)F)=O)C MBZBTDINMMUJLX-USXNREEHSA-N 0.000 claims 1
- UZOYZJDFERWLPF-USXNREEHSA-N N-[6-[(1R,5R)-3-amino-2,5-dimethyl-1-oxo-1-(2,2,2-trifluoroethylimino)-6H-1,2,4-thiadiazin-5-yl]-5-fluoropyridin-2-yl]-5-fluoro-3-methylpyridine-2-carboxamide Chemical compound NC=1N([S@@](C[C@@](N=1)(C)C1=C(C=CC(=N1)NC(=O)C1=NC=C(C=C1C)F)F)(=NCC(F)(F)F)=O)C UZOYZJDFERWLPF-USXNREEHSA-N 0.000 claims 1
- RYOMQTOPQKEDSX-TXULOHPCSA-N N-[6-[(1R,5R)-3-amino-2,5-dimethyl-1-oxo-1-(2,2,2-trifluoroethylimino)-6H-1,2,4-thiadiazin-5-yl]-5-fluoropyridin-2-yl]-5-methoxypyrazine-2-carboxamide Chemical compound NC=1N([S@@](C[C@@](N=1)(C)C1=C(C=CC(=N1)NC(=O)C1=NC=C(N=C1)OC)F)(=NCC(F)(F)F)=O)C RYOMQTOPQKEDSX-TXULOHPCSA-N 0.000 claims 1
- VQRZLLKYMXQQIK-PTIIMASVSA-N NC=1N([S@@](C[C@@](N=1)(C)C1=C(C=CC(=N1)NC(=O)C1=NC=C(C=C1)OCC#C)F)(=NCC(F)(F)F)=O)C Chemical compound NC=1N([S@@](C[C@@](N=1)(C)C1=C(C=CC(=N1)NC(=O)C1=NC=C(C=C1)OCC#C)F)(=NCC(F)(F)F)=O)C VQRZLLKYMXQQIK-PTIIMASVSA-N 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 230000003941 amyloidogenesis Effects 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP14181123 | 2014-08-15 | ||
| EP14181123.2 | 2014-08-15 | ||
| PCT/EP2015/068506 WO2016023927A1 (en) | 2014-08-15 | 2015-08-12 | 2,2,2-trifluoroethyl-thiadiazines |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017524006A JP2017524006A (ja) | 2017-08-24 |
| JP2017524006A5 true JP2017524006A5 (https=) | 2018-07-26 |
| JP6543697B2 JP6543697B2 (ja) | 2019-07-10 |
Family
ID=51302940
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017506993A Expired - Fee Related JP6543697B2 (ja) | 2014-08-15 | 2015-08-12 | ２，２，２−トリフルオロエチル−チアジアジン類 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US9896438B2 (https=) |
| EP (1) | EP3180330B1 (https=) |
| JP (1) | JP6543697B2 (https=) |
| KR (1) | KR20170043581A (https=) |
| CN (1) | CN106459006B (https=) |
| BR (1) | BR112016026814A8 (https=) |
| CA (1) | CA2952160A1 (https=) |
| MX (1) | MX375329B (https=) |
| RU (1) | RU2692102C2 (https=) |
| WO (1) | WO2016023927A1 (https=) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109180672A (zh) * | 2018-09-29 | 2019-01-11 | 广东东阳光药业有限公司 | 亚氨基噻二嗪二氧化物衍生物及其用途 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19500558A1 (de) * | 1995-01-11 | 1996-07-18 | Merck Patent Gmbh | 3-Alkoxycarbonyl-thiadiazinone |
| EP2485590B1 (en) | 2009-10-08 | 2015-01-07 | Merck Sharp & Dohme Corp. | Pentafluorosulfur imino heterocyclic compounds as bace-1 inhibitors, compositions, and their use |
| UA108363C2 (uk) * | 2009-10-08 | 2015-04-27 | Похідні імінотіадіазиндіоксиду як інгібітори bace, композиція на їх основі і їх застосування | |
| WO2014150331A1 (en) * | 2013-03-15 | 2014-09-25 | Merck Sharp & Dohme Corp. | S-imino-s-oxo iminothiazine compounds as bace inhibitors, compositions, and their use |
| US9428476B2 (en) * | 2013-03-15 | 2016-08-30 | Merck Sharp & Dohme Corp. | S-imino-S-oxo-iminothiadiazine compounds as BACE inhibitors, compositions, and their use |
| CN105683199B (zh) * | 2013-12-20 | 2018-06-26 | 豪夫迈·罗氏有限公司 | 5-芳基-1-亚氨基-1-氧代-[1，2，4]噻二嗪 |
-
2015
- 2015-08-12 US US15/502,044 patent/US9896438B2/en not_active Expired - Fee Related
- 2015-08-12 RU RU2017107495A patent/RU2692102C2/ru active
- 2015-08-12 MX MX2016016061A patent/MX375329B/es active IP Right Grant
- 2015-08-12 KR KR1020177006946A patent/KR20170043581A/ko not_active Ceased
- 2015-08-12 EP EP15748252.2A patent/EP3180330B1/en not_active Not-in-force
- 2015-08-12 JP JP2017506993A patent/JP6543697B2/ja not_active Expired - Fee Related
- 2015-08-12 WO PCT/EP2015/068506 patent/WO2016023927A1/en not_active Ceased
- 2015-08-12 CN CN201580032183.8A patent/CN106459006B/zh not_active Expired - Fee Related
- 2015-08-12 BR BR112016026814A patent/BR112016026814A8/pt active Search and Examination
- 2015-08-12 CA CA2952160A patent/CA2952160A1/en not_active Abandoned