JP2020503295A5 - - Google Patents
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- JP2020503295A5 JP2020503295A5 JP2019531735A JP2019531735A JP2020503295A5 JP 2020503295 A5 JP2020503295 A5 JP 2020503295A5 JP 2019531735 A JP2019531735 A JP 2019531735A JP 2019531735 A JP2019531735 A JP 2019531735A JP 2020503295 A5 JP2020503295 A5 JP 2020503295A5
- Authority
- JP
- Japan
- Prior art keywords
- hepta
- thia
- azabicyclo
- ethynyl
- amino
- 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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- 150000001875 compounds Chemical class 0.000 claims 47
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 33
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 33
- -1 2-propynyloxy Chemical group 0.000 claims 32
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 23
- 150000003839 salts Chemical class 0.000 claims 23
- GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 claims 16
- 125000000217 alkyl group Chemical group 0.000 claims 9
- 206010012289 Dementia Diseases 0.000 claims 8
- 229910052757 nitrogen Inorganic materials 0.000 claims 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 229940079593 drug Drugs 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- SSXJHQZOHUYEGD-UHFFFAOYSA-N 3-Methoxynobiletin Chemical compound C1=C(OC)C(OC)=CC=C1C1=C(OC)C(=O)C2=C(OC)C(OC)=C(OC)C(OC)=C2O1 SSXJHQZOHUYEGD-UHFFFAOYSA-N 0.000 claims 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 4
- 208000024827 Alzheimer disease Diseases 0.000 claims 4
- 208000010877 cognitive disease Diseases 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 4
- 125000001786 isothiazolyl group Chemical group 0.000 claims 4
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- OADSMBXFJIAAJA-UHFFFAOYSA-N oct-4-enamide Chemical compound CCCC=CCCC(N)=O OADSMBXFJIAAJA-UHFFFAOYSA-N 0.000 claims 4
- 125000004076 pyridyl group Chemical group 0.000 claims 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 4
- 125000000335 thiazolyl group Chemical group 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- WRIHTLGFUKBBKQ-CEAUUGKZSA-N (1S,5S)-5-[5-[2-(5-chloro-3-methylpyridin-2-yl)ethynyl]-2-fluorophenyl]-1-(methoxymethyl)-5-methyl-2-thia-4-azabicyclo[4.1.0]hept-3-en-3-amine Chemical compound ClC=1C=C(C(=NC=1)C#CC=1C=CC(=C(C=1)[C@]1(N=C(S[C@]2(CC12)COC)N)C)F)C WRIHTLGFUKBBKQ-CEAUUGKZSA-N 0.000 claims 2
- OMEMOIMHKXXIAX-AGILITTLSA-N (1S,5S,6S)-1,5-bis(fluoromethyl)-5-[2-fluoro-5-[2-[5-(1,3-oxazol-2-ylmethoxy)pyridin-2-yl]ethynyl]phenyl]-2-thia-4-azabicyclo[4.1.0]hept-3-en-3-amine Chemical compound FC1=C(C=C(C=C1)C#CC1=NC=C(C=C1)OCC=1OC=CN=1)[C@]1(N=C(S[C@]2(C[C@@H]12)CF)N)CF OMEMOIMHKXXIAX-AGILITTLSA-N 0.000 claims 2
- RAHDYDYNSIAFMG-FDJWOJMMSA-N (1S,5S,6S)-3-amino-5-[2-fluoro-5-[2-[3-methyl-5-(1,3-oxazol-2-ylmethoxy)pyridin-2-yl]ethynyl]phenyl]-N,N,5-trimethyl-2-thia-4-azabicyclo[4.1.0]hept-3-ene-1-carboxamide Chemical compound NC=1S[C@]2(C[C@H]2[C@@](N=1)(C)C1=C(C=CC(=C1)C#CC1=NC=C(C=C1C)OCC=1OC=CN=1)F)C(=O)N(C)C RAHDYDYNSIAFMG-FDJWOJMMSA-N 0.000 claims 2
- CBYOFAWUWAYPKP-KSEOMHKRSA-N (1S,5S,6S)-3-amino-5-[5-[2-(5-cyano-3-methylpyridin-2-yl)ethynyl]-2-fluorophenyl]-5-methyl-2-thia-4-azabicyclo[4.1.0]hept-3-ene-1-carbonitrile Chemical compound NC=1S[C@]2(C[C@H]2[C@@](N=1)(C)C1=C(C=CC(=C1)C#CC1=NC=C(C=C1C)C#N)F)C#N CBYOFAWUWAYPKP-KSEOMHKRSA-N 0.000 claims 2
- KEYGOCWGASLCFN-ZTCOLXNVSA-N (1S,5S,6S)-3-amino-5-[5-[2-(5-cyano-3-methylpyridin-2-yl)ethynyl]-2-fluorophenyl]-N,N,5-trimethyl-2-thia-4-azabicyclo[4.1.0]hept-3-ene-1-carboxamide Chemical compound NC=1S[C@]2(C[C@H]2[C@@](N=1)(C)C1=C(C=CC(=C1)C#CC1=NC=C(C=C1C)C#N)F)C(=O)N(C)C KEYGOCWGASLCFN-ZTCOLXNVSA-N 0.000 claims 2
- FAQNBNVGHSOMNY-MISYRCLQSA-N (1S,5S,6S)-5-[5-[2-(5-chloropyridin-2-yl)ethynyl]-2-fluorophenyl]-1,5-bis(fluoromethyl)-2-thia-4-azabicyclo[4.1.0]hept-3-en-3-amine Chemical compound ClC=1C=CC(=NC=1)C#CC=1C=CC(=C(C=1)[C@]1(N=C(S[C@]2(C[C@@H]12)CF)N)CF)F FAQNBNVGHSOMNY-MISYRCLQSA-N 0.000 claims 2
- AOKKWUDSGZAXHM-HSWNYDEUSA-N (E)-3-[(1R,5S,6S)-3-amino-5-[5-[2-(5-cyanopyridin-2-yl)ethynyl]-2-fluorophenyl]-5-(fluoromethyl)-2-thia-4-azabicyclo[4.1.0]hept-3-en-1-yl]-N,N-dimethylprop-2-enamide Chemical compound NC=1S[C@]2(C[C@H]2[C@@](N=1)(CF)C1=C(C=CC(=C1)C#CC1=NC=C(C=C1)C#N)F)/C=C/C(=O)N(C)C AOKKWUDSGZAXHM-HSWNYDEUSA-N 0.000 claims 2
- XWXPRCDFFCVMNT-UHFFFAOYSA-N 1,3-thiazole-5-carbonitrile Chemical compound N#CC1=CN=CS1 XWXPRCDFFCVMNT-UHFFFAOYSA-N 0.000 claims 2
- AFTWTRHAYWBSST-ONGRUHMKSA-N 2-[2-[3-[(1R,5S,6S)-3-amino-5-(fluoromethyl)-1-[(E)-3-morpholin-4-yl-3-oxoprop-1-enyl]-2-thia-4-azabicyclo[4.1.0]hept-3-en-5-yl]-4-fluorophenyl]ethynyl]pyrimidine-5-carbonitrile Chemical compound NC1=N[C@@](CF)([C@@H]2C[C@@]2(S1)\C=C\C(=O)N1CCOCC1)c1cc(ccc1F)C#Cc1ncc(cn1)C#N AFTWTRHAYWBSST-ONGRUHMKSA-N 0.000 claims 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- HKMWURYHQXDLAG-NVAWJBEOSA-N 4-[2-[3-[(1R,5S,6S)-3-amino-5-(fluoromethyl)-1-[(E)-3-morpholin-4-yl-3-oxoprop-1-enyl]-2-thia-4-azabicyclo[4.1.0]hept-3-en-5-yl]-4-fluorophenyl]ethynyl]benzonitrile Chemical compound NC1=N[C@@](CF)([C@@H]2C[C@@]2(S1)\C=C\C(=O)N1CCOCC1)c1cc(ccc1F)C#Cc1ccc(cc1)C#N HKMWURYHQXDLAG-NVAWJBEOSA-N 0.000 claims 2
- RJOFQCKQEMAZEM-BAGYTPMASA-N 6-[2-[3-[(1R,5S,6S)-3-amino-1-(cyanomethyl)-5-(fluoromethyl)-2-thia-4-azabicyclo[4.1.0]hept-3-en-5-yl]-4-fluorophenyl]ethynyl]pyridine-3-carbonitrile Chemical compound NC=1S[C@]2(C[C@H]2[C@@](N=1)(CF)C=1C=C(C=CC=1F)C#CC1=NC=C(C#N)C=C1)CC#N RJOFQCKQEMAZEM-BAGYTPMASA-N 0.000 claims 2
- KJOFKJHARIZLRZ-ALCSNEQFSA-N 6-[2-[3-[(1R,5S,6S)-3-amino-5-(fluoromethyl)-1-[(E)-3-morpholin-4-yl-3-oxoprop-1-enyl]-2-thia-4-azabicyclo[4.1.0]hept-3-en-5-yl]-4-fluorophenyl]ethynyl]-5-methylpyridine-3-carbonitrile Chemical compound NC=1S[C@]2(C[C@H]2[C@@](N=1)(CF)C=1C=C(C=CC=1F)C#CC1=NC=C(C#N)C=C1C)\C=C\C(=O)N1CCOCC1 KJOFKJHARIZLRZ-ALCSNEQFSA-N 0.000 claims 2
- FRVCLHJFWPHQDO-ACYVMRIUSA-N 6-[2-[3-[(1R,5S,6S)-3-amino-5-(fluoromethyl)-1-[(E)-3-morpholin-4-yl-3-oxoprop-1-enyl]-2-thia-4-azabicyclo[4.1.0]hept-3-en-5-yl]-4-fluorophenyl]ethynyl]pyridine-3-carbonitrile Chemical compound NC=1S[C@]2(C[C@H]2[C@@](N=1)(CF)C=1C=C(C=CC=1F)C#CC1=NC=C(C#N)C=C1)\C=C\C(=O)N1CCOCC1 FRVCLHJFWPHQDO-ACYVMRIUSA-N 0.000 claims 2
- MYTZXYYCRAMPEU-PWIZWCRZSA-N 6-[2-[5-[(1S,5S,6S)-3-amino-1-(fluoromethyl)-5-methyl-2-thia-4-azabicyclo[4.1.0]hept-3-en-5-yl]-6-fluoropyridin-3-yl]ethynyl]pyridine-3-carbonitrile Chemical compound NC=1S[C@]2(C[C@H]2[C@@](N=1)(C)C=1C=C(C=NC=1F)C#CC1=NC=C(C#N)C=C1)CF MYTZXYYCRAMPEU-PWIZWCRZSA-N 0.000 claims 2
- 206010008111 Cerebral haemorrhage Diseases 0.000 claims 2
- 208000028698 Cognitive impairment Diseases 0.000 claims 2
- 208000011990 Corticobasal Degeneration Diseases 0.000 claims 2
- 201000010374 Down Syndrome Diseases 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- DZHSAHHDTRWUTF-SIQRNXPUSA-N amyloid-beta polypeptide 42 Chemical compound C([C@@H](C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@H](C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)NCC(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(O)=O)[C@@H](C)CC)C(C)C)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@@H](NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)CNC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC(O)=O)C(C)C)C(C)C)C1=CC=CC=C1 DZHSAHHDTRWUTF-SIQRNXPUSA-N 0.000 claims 2
- 206010002022 amyloidosis Diseases 0.000 claims 2
- 210000004556 brain Anatomy 0.000 claims 2
- 230000002490 cerebral effect Effects 0.000 claims 2
- 210000001175 cerebrospinal fluid Anatomy 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- PMSVVUSIPKHUMT-UHFFFAOYSA-N cyanopyrazine Chemical compound N#CC1=CN=CC=N1 PMSVVUSIPKHUMT-UHFFFAOYSA-N 0.000 claims 2
- YGUTWCADDMAUOD-UHFFFAOYSA-N hept-3-en-3-amine Chemical compound CCCC=C(N)CC YGUTWCADDMAUOD-UHFFFAOYSA-N 0.000 claims 2
- 230000007505 plaque formation Effects 0.000 claims 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims 2
- CFWGZKJFJHRPLR-XKQJLSEDSA-N (1S,5S,6S)-3-amino-5-(5-ethynyl-2-fluorophenyl)-N,N,5-trimethyl-2-thia-4-azabicyclo[4.1.0]hept-3-ene-1-carboxamide Chemical compound NC=1S[C@]2(C[C@H]2[C@@](N=1)(C)C1=C(C=CC(=C1)C#C)F)C(=O)N(C)C CFWGZKJFJHRPLR-XKQJLSEDSA-N 0.000 claims 1
- MOAJIFLFRHPNCU-GPUOULLFSA-N (1S,5S,6S)-3-amino-5-[2-fluoro-5-[2-(5-prop-2-ynoxypyridin-2-yl)ethynyl]phenyl]-N,N,5-trimethyl-2-thia-4-azabicyclo[4.1.0]hept-3-ene-1-carboxamide Chemical compound NC=1S[C@]2(C[C@H]2[C@@](N=1)(C)C1=C(C=CC(=C1)C#CC1=NC=C(C=C1)OCC#C)F)C(=O)N(C)C MOAJIFLFRHPNCU-GPUOULLFSA-N 0.000 claims 1
- ASCVRCHPGUMCIB-ZTCOLXNVSA-N (1S,5S,6S)-3-amino-5-[5-[2-(5-cyano-3-methylpyridin-2-yl)ethynyl]-2-fluorophenyl]-5-(fluoromethyl)-N,N-dimethyl-2-thia-4-azabicyclo[4.1.0]hept-3-ene-1-carboxamide Chemical compound NC=1S[C@]2(C[C@H]2[C@@](N=1)(CF)C1=C(C=CC(=C1)C#CC1=NC=C(C=C1C)C#N)F)C(=O)N(C)C ASCVRCHPGUMCIB-ZTCOLXNVSA-N 0.000 claims 1
- MLJGESCVVGWMSL-MISYRCLQSA-N (1S,5S,6S)-5-[5-[2-(4-chloropyridin-2-yl)ethynyl]-2-fluorophenyl]-1,5-bis(fluoromethyl)-2-thia-4-azabicyclo[4.1.0]hept-3-en-3-amine Chemical compound ClC1=CC(=NC=C1)C#CC=1C=CC(=C(C=1)[C@]1(N=C(S[C@]2(C[C@@H]12)CF)N)CF)F MLJGESCVVGWMSL-MISYRCLQSA-N 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 1
- UUCVLVXHCQKZPD-ZEBAXETDSA-N (E)-3-[(1R,5S,6S)-3-amino-5-[5-[2-(5-chloropyrimidin-2-yl)ethynyl]-2-fluorophenyl]-5-(fluoromethyl)-2-thia-4-azabicyclo[4.1.0]hept-3-en-1-yl]-1-morpholin-4-ylprop-2-en-1-one Chemical compound NC=1S[C@]2(C[C@H]2[C@@](N=1)(CF)C1=C(C=CC(=C1)C#CC1=NC=C(C=N1)Cl)F)/C=C/C(=O)N1CCOCC1 UUCVLVXHCQKZPD-ZEBAXETDSA-N 0.000 claims 1
- NGFGTPHIPOZBPD-HZQXDJCGSA-N 6-[2-[3-[(1R,5S,6S)-3-amino-5-(fluoromethyl)-1-[(E)-3-morpholin-4-yl-3-oxoprop-1-enyl]-2-thia-4-azabicyclo[4.1.0]hept-3-en-5-yl]-4-fluorophenyl]ethynyl]-5-fluoropyridine-3-carbonitrile Chemical compound NC=1S[C@]2(C[C@H]2[C@@](N=1)(CF)C=1C=C(C=CC=1F)C#CC1=NC=C(C#N)C=C1F)\C=C\C(=O)N1CCOCC1 NGFGTPHIPOZBPD-HZQXDJCGSA-N 0.000 claims 1
- KTNWHHMLWOVZTA-RQFYCUQDSA-N 6-[2-[5-[(1S,5S)-3-amino-5-methyl-1-(pyrrolidine-1-carbonyl)-2-thia-4-azabicyclo[4.1.0]hept-3-en-5-yl]-6-fluoropyridin-3-yl]ethynyl]-5-methylpyridine-3-carbonitrile Chemical compound NC=1S[C@]2(CC2[C@@](N=1)(C)C=1C=C(C=NC=1F)C#CC1=NC=C(C#N)C=C1C)C(=O)N1CCCC1 KTNWHHMLWOVZTA-RQFYCUQDSA-N 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 208000012902 Nervous system disease Diseases 0.000 claims 1
- 206010033799 Paralysis Diseases 0.000 claims 1
- 206010048327 Supranuclear palsy Diseases 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 208000027061 mild cognitive impairment Diseases 0.000 claims 1
- 201000001119 neuropathy Diseases 0.000 claims 1
- 230000007823 neuropathy Effects 0.000 claims 1
- 208000033808 peripheral neuropathy Diseases 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662434721P | 2016-12-15 | 2016-12-15 | |
| US62/434,721 | 2016-12-15 | ||
| PCT/US2017/066184 WO2018112086A1 (en) | 2016-12-15 | 2017-12-13 | Cyclopropyl fused thiazine derivatives as beta-secretase inhibitors and methods of use |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2020503295A JP2020503295A (ja) | 2020-01-30 |
| JP2020503295A5 true JP2020503295A5 (enExample) | 2021-01-28 |
| JP7159161B2 JP7159161B2 (ja) | 2022-10-24 |
Family
ID=60888747
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019531735A Active JP7159161B2 (ja) | 2016-12-15 | 2017-12-13 | β－セクレターゼ阻害剤としてのシクロプロピル縮合チアジン誘導体および使用方法 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US10889581B2 (enExample) |
| EP (1) | EP3555085B1 (enExample) |
| JP (1) | JP7159161B2 (enExample) |
| AU (1) | AU2017378316B2 (enExample) |
| MX (1) | MX386618B (enExample) |
| WO (1) | WO2018112086A1 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10889581B2 (en) | 2016-12-15 | 2021-01-12 | Amgen Inc. | Cyclopropyl fused thiazine derivatives as beta-secretase inhibitors and methods of use |
| MA54100A (fr) | 2016-12-15 | 2021-10-20 | Amgen Inc | Dérivés de thiazine en tant qu'inhibiteurs de bêta-sécrétase et procédés d'utilisation |
| US11021493B2 (en) | 2016-12-15 | 2021-06-01 | Amgen Inc. | 1,4-thiazine dioxide and 1,2,4-thiadiazine dioxide derivatives as beta-secretase inhibitors and methods of use |
| EP3555106B1 (en) | 2016-12-15 | 2022-03-09 | Amgen Inc. | Bicyclic thiazine and oxazine derivatives as beta-secretase inhibitors and methods of use |
| US10947223B2 (en) | 2016-12-15 | 2021-03-16 | Amgen Inc. | Substituted oxazines as beta-secretase inhibitors |
Family Cites Families (62)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5441870A (en) | 1992-04-15 | 1995-08-15 | Athena Neurosciences, Inc. | Methods for monitoring cellular processing of β-amyloid precursor protein |
| SI9300303A (en) | 1993-06-08 | 1994-12-31 | Krka Tovarna Zdravil | Process for isolation of hypolipemic effective substance |
| JPH11507538A (ja) | 1995-06-07 | 1999-07-06 | アテナ ニューロサイエンシズ インコーポレイティド | β−セクレターゼ、β−セクレターゼに対する抗体、及びβ−セクレターゼ阻害を検出するためのアッセイ |
| HK1042730B (zh) | 1998-09-24 | 2005-11-18 | 法玛西雅厄普约翰美国公司 | 阿尔茨海默氏疾病分泌酶 |
| EP2597087B1 (en) | 2005-10-25 | 2016-03-30 | Shionogi&Co., Ltd. | Dihydrooxazine and tetrahydropyrimidine derivatives as BACE 1 inhibitors |
| JP5383483B2 (ja) | 2007-04-24 | 2014-01-08 | 塩野義製薬株式会社 | アルツハイマー症治療用医薬組成物 |
| AU2008245082B8 (en) | 2007-04-24 | 2012-09-13 | Shionogi & Co., Ltd. | Aminodihydrothiazine derivatives substituted with a cyclic group |
| HUE026064T2 (en) | 2008-01-18 | 2016-05-30 | Eisai R&D Man Co Ltd | Condensed aminodihydrothiazine derivatives |
| TWI431004B (zh) | 2008-05-02 | 2014-03-21 | Lilly Co Eli | Ｂａｃｅ抑制劑 |
| NZ589590A (en) | 2008-06-13 | 2012-05-25 | Shionogi & Co | Sulfur-containing heterocyclic derivative having beta-secretase-inhibiting activity |
| ES2433223T3 (es) | 2008-07-28 | 2013-12-10 | Eisai R&D Management Co., Ltd. | Derivados de espiroaminodihidrotiazina |
| WO2010013302A1 (ja) | 2008-07-28 | 2010-02-04 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | スピロアミノジヒドロチアジン誘導体 |
| ES2539859T3 (es) | 2008-09-30 | 2015-07-06 | Eisai R&D Management Co., Ltd. | Nuevo derivado de aminodihidrotiazina condensado |
| AR077277A1 (es) | 2009-07-09 | 2011-08-17 | Lilly Co Eli | Compuestos de biciclo (1,3)tiazin-2-amina formulacion farmaceutica que lo comprende y su uso para la manufactura de un medicamento util para el tratamiento de la enfermedad de alzheimer |
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2017
- 2017-12-13 US US16/466,199 patent/US10889581B2/en active Active
- 2017-12-13 MX MX2019007103A patent/MX386618B/es unknown
- 2017-12-13 AU AU2017378316A patent/AU2017378316B2/en active Active
- 2017-12-13 EP EP17822987.8A patent/EP3555085B1/en active Active
- 2017-12-13 JP JP2019531735A patent/JP7159161B2/ja active Active
- 2017-12-13 WO PCT/US2017/066184 patent/WO2018112086A1/en not_active Ceased