JP2015534991A5 - - Google Patents
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- JP2015534991A5 JP2015534991A5 JP2015538226A JP2015538226A JP2015534991A5 JP 2015534991 A5 JP2015534991 A5 JP 2015534991A5 JP 2015538226 A JP2015538226 A JP 2015538226A JP 2015538226 A JP2015538226 A JP 2015538226A JP 2015534991 A5 JP2015534991 A5 JP 2015534991A5
- Authority
- JP
- Japan
- Prior art keywords
- thiopyrano
- tetrahydro
- fluoro
- methylamino
- diol
- 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.)
- Pending
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 72
- 125000003342 alkenyl group Chemical group 0.000 claims description 48
- 125000000217 alkyl group Chemical group 0.000 claims description 48
- 125000000304 alkynyl group Chemical group 0.000 claims description 48
- 229910052731 fluorine Inorganic materials 0.000 claims description 48
- 125000001153 fluoro group Chemical group F* 0.000 claims description 48
- 125000001424 substituent group Chemical group 0.000 claims description 48
- 229910052799 carbon Inorganic materials 0.000 claims description 42
- 150000001875 compounds Chemical class 0.000 claims description 38
- 125000003545 alkoxy group Chemical group 0.000 claims description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 18
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 101001120790 Caenorhabditis elegans UDP-N-acetylglucosamine-peptide N-acetylglucosaminyltransferase Proteins 0.000 claims description 10
- 201000011240 Frontotemporal dementia Diseases 0.000 claims description 8
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 8
- 201000010099 disease Diseases 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 8
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- 208000010859 Creutzfeldt-Jakob disease Diseases 0.000 claims description 6
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- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
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- 206010047115 Vasculitis Diseases 0.000 claims description 4
- 230000007850 degeneration Effects 0.000 claims description 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 4
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- MWNSLTYIIVHOQL-BZCSJUTBSA-N (3ar,5r,6s,7ar)-5-[(1s)-1-hydroxyethyl]-2-(methylamino)-5,6,7,7a-tetrahydro-3ah-thiopyrano[3,2-d][1,3]thiazol-6-ol Chemical compound C1[C@H](O)[C@@H]([C@H](C)O)S[C@@H]2SC(NC)=N[C@@H]21 MWNSLTYIIVHOQL-BZCSJUTBSA-N 0.000 claims description 2
- MLLXFDVHCCYLQB-JGKVKWKGSA-N (3ar,5r,6s,7r,7ar)-5-(hydroxymethyl)-2-(prop-2-ynylamino)-5,6,7,7a-tetrahydro-3ah-thiopyrano[3,2-d][1,3]thiazole-6,7-diol Chemical compound O[C@H]1[C@H](O)[C@@H](CO)S[C@@H]2SC(NCC#C)=N[C@@H]21 MLLXFDVHCCYLQB-JGKVKWKGSA-N 0.000 claims description 2
- JVQQLIJJIHETCG-FMDGEEDCSA-N (3ar,5r,6s,7r,7ar)-5-(hydroxymethyl)-2-[methoxy(methyl)amino]-5,6,7,7a-tetrahydro-3ah-thiopyrano[3,2-d][1,3]thiazole-6,7-diol Chemical compound [C@@H]1([C@H]([C@H](O)[C@@H](CO)S2)O)[C@H]2SC(N(C)OC)=N1 JVQQLIJJIHETCG-FMDGEEDCSA-N 0.000 claims description 2
- NKWWAKGWZXYHJT-JMHNFOGYSA-N (3ar,5r,6s,7r,7ar)-5-[(1s)-1-hydroxyethyl]-2-(methylamino)-5,6,7,7a-tetrahydro-3ah-thiopyrano[3,2-d][1,3]thiazole-6,7-diol Chemical compound [C@@H]1([C@H]([C@H](O)[C@@H]([C@H](C)O)S2)O)[C@H]2SC(NC)=N1 NKWWAKGWZXYHJT-JMHNFOGYSA-N 0.000 claims description 2
- VTMABFSHBNXTCW-HDLKOFKZSA-N (3ar,5r,6s,7r,7ar)-5-[(s)-hydroxy(phenyl)methyl]-2-(methylamino)-5,6,7,7a-tetrahydro-3ah-thiopyrano[3,2-d][1,3]thiazole-6,7-diol Chemical compound C1([C@H](O)[C@H]2S[C@H]3[C@@H]([C@H]([C@@H]2O)O)N=C(S3)NC)=CC=CC=C1 VTMABFSHBNXTCW-HDLKOFKZSA-N 0.000 claims description 2
- REQZJMOBRFKGGT-ZNSALQAWSA-N (3ar,5r,6s,7r,7ar)-5-[(s)-hydroxy(pyridin-3-yl)methyl]-2-(methylamino)-5,6,7,7a-tetrahydro-3ah-thiopyrano[3,2-d][1,3]thiazole-6,7-diol Chemical compound C1([C@H](O)[C@H]2S[C@H]3[C@@H]([C@H]([C@@H]2O)O)N=C(S3)NC)=CC=CN=C1 REQZJMOBRFKGGT-ZNSALQAWSA-N 0.000 claims description 2
- ORWXWXFTGYXWLY-JMHNFOGYSA-N (3ar,5r,6s,7r,7ar)-7-fluoro-5-[(1s)-1-hydroxyethyl]-2-(methylamino)-5,6,7,7a-tetrahydro-3ah-thiopyrano[3,2-d][1,3]thiazol-6-ol Chemical compound [C@@H]1([C@H]([C@H](O)[C@@H]([C@H](C)O)S2)F)[C@H]2SC(NC)=N1 ORWXWXFTGYXWLY-JMHNFOGYSA-N 0.000 claims description 2
- ULQATFNIZULGRZ-UELCQGJWSA-N (3ar,5s,6s,7ar)-5-(difluoromethyl)-2-(methylamino)-5,6,7,7a-tetrahydro-3ah-thiopyrano[3,2-d][1,3]thiazol-6-ol Chemical compound C1[C@H](O)[C@@H](C(F)F)S[C@@H]2SC(NC)=N[C@@H]21 ULQATFNIZULGRZ-UELCQGJWSA-N 0.000 claims description 2
- IHMSPWGRROGUCB-NTXXKDEISA-N (3ar,5s,6s,7r,7ar)-2-(azetidin-1-yl)-7-fluoro-5-[(1s)-2,2,2-trifluoro-1-hydroxyethyl]-5,6,7,7a-tetrahydro-3ah-thiopyrano[3,2-d][1,3]thiazol-6-ol Chemical compound S([C@H]1S[C@@H]([C@H]([C@H](F)[C@H]1N=1)O)[C@@H](O)C(F)(F)F)C=1N1CCC1 IHMSPWGRROGUCB-NTXXKDEISA-N 0.000 claims description 2
- OJJTZSAZGYIMDH-FJPOHGBRSA-N (3ar,5s,6s,7r,7ar)-2-(methylamino)-5-[(1s)-2,2,2-trifluoro-1-hydroxyethyl]-5,6,7,7a-tetrahydro-3ah-thiopyrano[3,2-d][1,3]thiazole-6,7-diol Chemical compound [C@@H]1([C@H]([C@H](O)[C@@H]([C@@H](O)C(F)(F)F)S2)O)[C@H]2SC(NC)=N1 OJJTZSAZGYIMDH-FJPOHGBRSA-N 0.000 claims description 2
- BTTYPUZBBMQPNX-RLZVPWTLSA-N (3ar,5s,6s,7r,7ar)-5-(difluoromethyl)-7-fluoro-2-(methylamino)-5,6,7,7a-tetrahydro-3ah-thiopyrano[3,2-d][1,3]thiazol-6-ol Chemical compound [C@@H]1([C@H]([C@H](O)[C@@H](C(F)F)S2)F)[C@H]2SC(NC)=N1 BTTYPUZBBMQPNX-RLZVPWTLSA-N 0.000 claims description 2
- UAURVGMIFJYDPD-NYMZXIIRSA-N (3ar,5s,6s,7r,7ar)-7-fluoro-5-(fluoromethyl)-2-(methylamino)-5,6,7,7a-tetrahydro-3ah-thiopyrano[3,2-d][1,3]thiazol-6-ol Chemical compound [C@@H]1([C@H]([C@H](O)[C@@H](CF)S2)F)[C@H]2SC(NC)=N1 UAURVGMIFJYDPD-NYMZXIIRSA-N 0.000 claims description 2
- BTTYPUZBBMQPNX-SDDMPLOYSA-N (3ar,5s,6s,7s,7ar)-5-(difluoromethyl)-7-fluoro-2-(methylamino)-5,6,7,7a-tetrahydro-3ah-thiopyrano[3,2-d][1,3]thiazol-6-ol Chemical compound [C@@H]1([C@@H]([C@H](O)[C@@H](C(F)F)S2)F)[C@H]2SC(NC)=N1 BTTYPUZBBMQPNX-SDDMPLOYSA-N 0.000 claims description 2
- OFHDLQIPFPSNRW-YMVPXFTJSA-N (3as,5r,6s,7ar)-5-[(1s)-1-hydroxyethyl]-2-(methylamino)-5,6,7,7a-tetrahydro-3ah-thiopyrano[3,2-d][1,3]oxazol-6-ol Chemical compound C1[C@H](O)[C@@H]([C@H](C)O)S[C@@H]2OC(NC)=N[C@@H]21 OFHDLQIPFPSNRW-YMVPXFTJSA-N 0.000 claims description 2
- GNRIQRPBAHFTHH-MZNFZHPNSA-N (3as,5r,6s,7r,7ar)-5-[(1s)-1-hydroxyethyl]-2-(methylamino)-5,6,7,7a-tetrahydro-3ah-thiopyrano[3,2-d][1,3]oxazole-6,7-diol Chemical compound [C@@H]1([C@H]([C@H](O)[C@@H]([C@H](C)O)S2)O)[C@H]2OC(NC)=N1 GNRIQRPBAHFTHH-MZNFZHPNSA-N 0.000 claims description 2
- SPFWTDOICVQDMX-MZNFZHPNSA-N (3as,5r,6s,7r,7ar)-7-fluoro-5-[(1s)-1-hydroxyethyl]-2-(methylamino)-5,6,7,7a-tetrahydro-3ah-thiopyrano[3,2-d][1,3]oxazol-6-ol Chemical compound [C@@H]1([C@H]([C@H](O)[C@@H]([C@H](C)O)S2)F)[C@H]2OC(NC)=N1 SPFWTDOICVQDMX-MZNFZHPNSA-N 0.000 claims description 2
- SPFWTDOICVQDMX-RJDKYLDESA-N (3as,5r,6s,7s,7ar)-7-fluoro-5-[(1s)-1-hydroxyethyl]-2-(methylamino)-5,6,7,7a-tetrahydro-3ah-thiopyrano[3,2-d][1,3]oxazol-6-ol Chemical compound [C@@H]1([C@@H]([C@H](O)[C@@H]([C@H](C)O)S2)F)[C@H]2OC(NC)=N1 SPFWTDOICVQDMX-RJDKYLDESA-N 0.000 claims description 2
- JTKJZPKDGCQYNZ-GZFNIDBVSA-N (3as,5s,6s,7ar)-5-(difluoromethyl)-2-(methylamino)-5,6,7,7a-tetrahydro-3ah-thiopyrano[3,2-d][1,3]oxazol-6-ol Chemical compound C1[C@H](O)[C@@H](C(F)F)S[C@@H]2OC(NC)=N[C@@H]21 JTKJZPKDGCQYNZ-GZFNIDBVSA-N 0.000 claims description 2
- DYDCDUIFQMZNEJ-JIOKVTTDSA-N (3as,5s,6s,7r,7ar)-2-(methylamino)-5-[(1s)-2,2,2-trifluoro-1-hydroxyethyl]-5,6,7,7a-tetrahydro-3ah-thiopyrano[3,2-d][1,3]oxazole-6,7-diol Chemical compound [C@@H]1([C@H]([C@H](O)[C@@H]([C@@H](O)C(F)(F)F)S2)O)[C@H]2OC(NC)=N1 DYDCDUIFQMZNEJ-JIOKVTTDSA-N 0.000 claims description 2
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- XTOHHFAZZIZQDF-GKHCUFPYSA-N (3as,5s,6s,7r,7ar)-7-fluoro-5-(fluoromethyl)-2-(methylamino)-5,6,7,7a-tetrahydro-3ah-thiopyrano[3,2-d][1,3]oxazol-6-ol Chemical compound [C@@H]1([C@H]([C@H](O)[C@@H](CF)S2)F)[C@H]2OC(NC)=N1 XTOHHFAZZIZQDF-GKHCUFPYSA-N 0.000 claims description 2
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- 125000006325 2-propenyl amino group Chemical group [H]C([H])=C([H])C([H])([H])N([H])* 0.000 claims description 2
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261720708P | 2012-10-31 | 2012-10-31 | |
| US61/720,708 | 2012-10-31 | ||
| PCT/CA2013/050822 WO2014067003A1 (en) | 2012-10-31 | 2013-10-30 | Glycosidase inhibitors and uses thereof |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018117768A Division JP2018172405A (ja) | 2012-10-31 | 2018-06-21 | グリコシダーゼ阻害剤およびその使用 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2015534991A JP2015534991A (ja) | 2015-12-07 |
| JP2015534991A5 true JP2015534991A5 (https=) | 2016-11-24 |
Family
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| Application Number | Title | Priority Date | Filing Date |
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| JP2015538226A Pending JP2015534991A (ja) | 2012-10-31 | 2013-10-30 | グリコシダーゼ阻害剤およびその使用 |
| JP2018117768A Pending JP2018172405A (ja) | 2012-10-31 | 2018-06-21 | グリコシダーゼ阻害剤およびその使用 |
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| JP (2) | JP2015534991A (https=) |
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| BR (1) | BR112015009638A2 (https=) |
| CA (1) | CA2890115A1 (https=) |
| RU (1) | RU2672873C2 (https=) |
| WO (1) | WO2014067003A1 (https=) |
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| EP2321289A4 (en) | 2008-08-01 | 2011-11-16 | Univ Fraser Simon | SELECTIVE GLYCOSIDASE HEMMER AND ITS USE |
| US9120781B2 (en) | 2010-05-11 | 2015-09-01 | Simon Fraser University | Selective glycosidase inhibitors and uses thereof |
| US8933040B2 (en) | 2010-11-08 | 2015-01-13 | Craig A. Coburn | Selective glycosidase inhibitors and uses thereof |
| DK2655388T3 (en) | 2010-12-23 | 2016-09-19 | Alectos Therapeutics Inc | Selective glykosidaseinhibitorer and uses thereof |
| WO2012126091A1 (en) | 2011-03-24 | 2012-09-27 | Alectos Therapeutics Inc. | Selective glycosidase inhibitors and uses thereof |
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| CN103889996B (zh) | 2011-06-27 | 2016-02-03 | 阿列科托斯治疗有限公司 | 选择性糖苷酶抑制剂及其用途 |
| WO2013000086A1 (en) | 2011-06-27 | 2013-01-03 | Alectos Therapeutics Inc. | Selective glycosidase inhibitors and uses thereof |
| WO2013000085A1 (en) | 2011-06-27 | 2013-01-03 | Alectos Therapeutics Inc. | Selective glycosidase inhibitors and uses thereof |
| WO2014032185A1 (en) | 2012-08-31 | 2014-03-06 | Alectos Therapeutics Inc. | Glycosidase inhibitors and uses thereof |
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| WO2014100934A1 (en) | 2012-12-24 | 2014-07-03 | Merck Sharp & Dohme Corp. | Glycosidase inhibitors and uses thereof |
| US12180205B2 (en) | 2018-09-19 | 2024-12-31 | Biogen Ma Inc. | O-glycoprotein-2-acetamido-2-deoxy-3-d-glucopyranosidase inhibitors |
| EP3966199B1 (en) * | 2019-05-10 | 2026-03-18 | Alectos Therapeutics Inc. | Non-lysosomal glucosylceramidase inhibitors and uses thereof |
| WO2024083820A1 (en) | 2022-10-18 | 2024-04-25 | Institut National de la Santé et de la Recherche Médicale | Method and composition for determining the level of o-glcnacylation in horses |
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-
2013
- 2013-10-30 WO PCT/CA2013/050822 patent/WO2014067003A1/en not_active Ceased
- 2013-10-30 RU RU2015120556A patent/RU2672873C2/ru not_active IP Right Cessation
- 2013-10-30 CA CA2890115A patent/CA2890115A1/en not_active Abandoned
- 2013-10-30 CN CN201380064854.XA patent/CN104837845B/zh not_active Expired - Fee Related
- 2013-10-30 BR BR112015009638A patent/BR112015009638A2/pt not_active Application Discontinuation
- 2013-10-30 AU AU2013337570A patent/AU2013337570B2/en not_active Ceased
- 2013-10-30 US US14/439,790 patent/US9695197B2/en not_active Expired - Fee Related
- 2013-10-30 KR KR1020157013109A patent/KR20150079711A/ko not_active Ceased
- 2013-10-30 JP JP2015538226A patent/JP2015534991A/ja active Pending
- 2013-10-30 EP EP13852129.9A patent/EP2914604A4/en not_active Ceased
-
2018
- 2018-06-21 JP JP2018117768A patent/JP2018172405A/ja active Pending
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