JP2014524911A5 - - Google Patents
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- Publication number
- JP2014524911A5 JP2014524911A5 JP2014517357A JP2014517357A JP2014524911A5 JP 2014524911 A5 JP2014524911 A5 JP 2014524911A5 JP 2014517357 A JP2014517357 A JP 2014517357A JP 2014517357 A JP2014517357 A JP 2014517357A JP 2014524911 A5 JP2014524911 A5 JP 2014524911A5
- Authority
- JP
- Japan
- Prior art keywords
- fluoro
- pyrano
- tetrahydro
- thiazol
- hydroxyethyl
- 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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- 229910052739 hydrogen Inorganic materials 0.000 claims description 85
- 125000003342 alkenyl group Chemical group 0.000 claims description 56
- 125000000217 alkyl group Chemical group 0.000 claims description 56
- 125000000304 alkynyl group Chemical group 0.000 claims description 56
- 125000001153 fluoro group Chemical group F* 0.000 claims description 56
- 150000001875 compounds Chemical class 0.000 claims description 55
- 229910052799 carbon Inorganic materials 0.000 claims description 49
- 125000001424 substituent group Chemical group 0.000 claims description 49
- 229910052731 fluorine Inorganic materials 0.000 claims description 42
- 125000003545 alkoxy group Chemical group 0.000 claims description 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
- 150000003839 salts Chemical class 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 125000002252 acyl group Chemical group 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 14
- 229920002554 vinyl polymer Polymers 0.000 claims description 14
- 101001120790 Caenorhabditis elegans UDP-N-acetylglucosamine-peptide N-acetylglucosaminyltransferase Proteins 0.000 claims description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
- 201000011240 Frontotemporal dementia Diseases 0.000 claims description 8
- 208000029523 Interstitial Lung disease Diseases 0.000 claims description 8
- 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims description 8
- 201000010099 disease Diseases 0.000 claims description 8
- 230000004770 neurodegeneration Effects 0.000 claims description 8
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 7
- 208000020406 Creutzfeldt Jacob disease Diseases 0.000 claims description 6
- 208000003407 Creutzfeldt-Jakob Syndrome Diseases 0.000 claims description 6
- 208000010859 Creutzfeldt-Jakob disease Diseases 0.000 claims description 6
- 201000004624 Dermatitis Diseases 0.000 claims description 6
- 206010020751 Hypersensitivity Diseases 0.000 claims description 6
- 206010028980 Neoplasm Diseases 0.000 claims description 6
- 208000034799 Tauopathies Diseases 0.000 claims description 6
- 208000026935 allergic disease Diseases 0.000 claims description 6
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 6
- 201000011510 cancer Diseases 0.000 claims description 6
- 208000010877 cognitive disease Diseases 0.000 claims description 6
- 230000009610 hypersensitivity Effects 0.000 claims description 6
- 230000002401 inhibitory effect Effects 0.000 claims description 6
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 6
- 201000002212 progressive supranuclear palsy Diseases 0.000 claims description 6
- 208000024827 Alzheimer disease Diseases 0.000 claims description 4
- 206010012289 Dementia Diseases 0.000 claims description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- 208000000609 Pick Disease of the Brain Diseases 0.000 claims description 4
- 208000024571 Pick disease Diseases 0.000 claims description 4
- 208000036757 Postencephalitic parkinsonism Diseases 0.000 claims description 4
- 201000004681 Psoriasis Diseases 0.000 claims description 4
- 229940124639 Selective inhibitor Drugs 0.000 claims description 4
- 206010052779 Transplant rejections Diseases 0.000 claims description 4
- 206010047115 Vasculitis Diseases 0.000 claims description 4
- 230000007850 degeneration Effects 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 230000005764 inhibitory process Effects 0.000 claims description 4
- 208000027061 mild cognitive impairment Diseases 0.000 claims description 4
- 208000000170 postencephalitic Parkinson disease Diseases 0.000 claims description 4
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 4
- LHPQBKLAIXBHQU-SLBCVNJHSA-N (3ar,5r,6r,7ar)-5-[(1s)-1-hydroxyethyl]-2-(methylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazol-6-ol Chemical compound C1[C@@H](O)[C@@H]([C@H](C)O)O[C@@H]2SC(NC)=N[C@@H]21 LHPQBKLAIXBHQU-SLBCVNJHSA-N 0.000 claims description 2
- PPCNNKVPHUHGJA-LZISRMJESA-N (3ar,5r,6r,7r,7ar)-2-(azetidin-1-yl)-7-fluoro-5-[(1s)-1-hydroxyethyl]-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazol-6-ol Chemical compound S([C@H]1O[C@@H]([C@H]([C@H](F)[C@H]1N=1)O)[C@@H](O)C)C=1N1CCC1 PPCNNKVPHUHGJA-LZISRMJESA-N 0.000 claims description 2
- AZELLSBKKCSFGM-VMQOHUEUSA-N (3ar,5r,6r,7r,7ar)-2-(dimethylamino)-7-fluoro-5-[(1r)-1-hydroxyethyl]-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazol-6-ol Chemical compound F[C@H]1[C@H](O)[C@@H]([C@H](O)C)O[C@@H]2SC(N(C)C)=N[C@@H]21 AZELLSBKKCSFGM-VMQOHUEUSA-N 0.000 claims description 2
- AZELLSBKKCSFGM-LHCONQACSA-N (3ar,5r,6r,7r,7ar)-2-(dimethylamino)-7-fluoro-5-[(1s)-1-hydroxyethyl]-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazol-6-ol Chemical compound F[C@H]1[C@H](O)[C@@H]([C@@H](O)C)O[C@@H]2SC(N(C)C)=N[C@@H]21 AZELLSBKKCSFGM-LHCONQACSA-N 0.000 claims description 2
- JUBDIOYUYOXOKG-VMQOHUEUSA-N (3ar,5r,6r,7r,7ar)-2-(ethylamino)-7-fluoro-5-[(1r)-1-hydroxyethyl]-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazol-6-ol Chemical compound S1C(NCC)=N[C@H]2[C@@H]1O[C@H]([C@@H](C)O)[C@@H](O)[C@@H]2F JUBDIOYUYOXOKG-VMQOHUEUSA-N 0.000 claims description 2
- JUBDIOYUYOXOKG-LHCONQACSA-N (3ar,5r,6r,7r,7ar)-2-(ethylamino)-7-fluoro-5-[(1s)-1-hydroxyethyl]-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazol-6-ol Chemical compound S1C(NCC)=N[C@H]2[C@@H]1O[C@H]([C@H](C)O)[C@@H](O)[C@@H]2F JUBDIOYUYOXOKG-LHCONQACSA-N 0.000 claims description 2
- JUXPSVXTSBHNSY-NLZQRBTFSA-N (3ar,5r,6r,7r,7ar)-2-amino-7-fluoro-5-[(1s)-1-hydroxyethyl]-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazol-6-ol Chemical compound F[C@H]1[C@H](O)[C@@H]([C@@H](O)C)O[C@@H]2SC(N)=N[C@@H]21 JUXPSVXTSBHNSY-NLZQRBTFSA-N 0.000 claims description 2
- RKHRVXGGDIHLKC-VMRAVBONSA-N (3ar,5r,6r,7r,7ar)-5-[(1s)-3,3-difluoro-1-hydroxypropyl]-7-fluoro-2-(methylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazol-6-ol Chemical compound S1C(NC)=N[C@H]2[C@@H]1O[C@H]([C@@H](O)CC(F)F)[C@@H](O)[C@@H]2F RKHRVXGGDIHLKC-VMRAVBONSA-N 0.000 claims description 2
- WLJQSLNDQFCZQE-VFZPANTDSA-N (3ar,5r,6r,7r,7ar)-5-[(s)-cyclobutyl(hydroxy)methyl]-7-fluoro-2-(methylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazol-6-ol Chemical compound C1([C@H](O)[C@H]2O[C@H]3[C@@H]([C@H]([C@@H]2O)F)N=C(S3)NC)CCC1 WLJQSLNDQFCZQE-VFZPANTDSA-N 0.000 claims description 2
- FDPZXDQXJXLILH-PQTSNVLCSA-N (3ar,5r,6r,7r,7ar)-5-[(s)-cyclopentyl(hydroxy)methyl]-7-fluoro-2-(methylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazol-6-ol Chemical compound C1([C@H](O)[C@H]2O[C@H]3[C@@H]([C@H]([C@@H]2O)F)N=C(S3)NC)CCCC1 FDPZXDQXJXLILH-PQTSNVLCSA-N 0.000 claims description 2
- IVOAADYEBZYJSD-NRNPDCPVSA-N (3ar,5r,6r,7r,7ar)-5-[(s)-cyclopropyl(hydroxy)methyl]-7-fluoro-2-(methylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazol-6-ol Chemical compound C1([C@H](O)[C@H]2O[C@H]3[C@@H]([C@H]([C@@H]2O)F)N=C(S3)NC)CC1 IVOAADYEBZYJSD-NRNPDCPVSA-N 0.000 claims description 2
- WRBFXAOTGCXIHN-JMHNFOGYSA-N (3ar,5r,6r,7r,7ar)-7-fluoro-2-(methylamino)-5-[(1s)-3,3,3-trifluoro-1-hydroxypropyl]-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazol-6-ol Chemical compound S1C(NC)=N[C@H]2[C@@H]1O[C@H]([C@@H](O)CC(F)(F)F)[C@@H](O)[C@@H]2F WRBFXAOTGCXIHN-JMHNFOGYSA-N 0.000 claims description 2
- DYOCXHLLDLBZHU-CVBHLRHXSA-N (3ar,5r,6r,7r,7ar)-7-fluoro-5-[(1r)-1-hydroxyethyl]-2-(methylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazol-6-ol Chemical compound S1C(NC)=N[C@H]2[C@@H]1O[C@H]([C@@H](C)O)[C@@H](O)[C@@H]2F DYOCXHLLDLBZHU-CVBHLRHXSA-N 0.000 claims description 2
- NPOCUQDEGGFPDG-JMHNFOGYSA-N (3ar,5r,6r,7r,7ar)-7-fluoro-5-[(1r)-2-fluoro-1-hydroxyethyl]-2-(methylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazol-6-ol Chemical compound S1C(NC)=N[C@H]2[C@@H]1O[C@H]([C@@H](O)CF)[C@@H](O)[C@@H]2F NPOCUQDEGGFPDG-JMHNFOGYSA-N 0.000 claims description 2
- DYOCXHLLDLBZHU-JMHNFOGYSA-N (3ar,5r,6r,7r,7ar)-7-fluoro-5-[(1s)-1-hydroxyethyl]-2-(methylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazol-6-ol Chemical compound S1C(NC)=N[C@H]2[C@@H]1O[C@H]([C@H](C)O)[C@@H](O)[C@@H]2F DYOCXHLLDLBZHU-JMHNFOGYSA-N 0.000 claims description 2
- ATPLWNORUCFDIM-LHCONQACSA-N (3ar,5r,6r,7r,7ar)-7-fluoro-5-[(1s)-1-hydroxypropyl]-2-(methylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazol-6-ol Chemical compound F[C@H]1[C@H](O)[C@@H]([C@@H](O)CC)O[C@@H]2SC(NC)=N[C@@H]21 ATPLWNORUCFDIM-LHCONQACSA-N 0.000 claims description 2
- PPCNNKVPHUHGJA-ZPASOGBRSA-N (3ar,5r,6r,7s,7ar)-2-(azetidin-1-yl)-7-fluoro-5-[(1s)-1-hydroxyethyl]-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazol-6-ol Chemical compound S([C@H]1O[C@@H]([C@H]([C@@H](F)[C@H]1N=1)O)[C@@H](O)C)C=1N1CCC1 PPCNNKVPHUHGJA-ZPASOGBRSA-N 0.000 claims description 2
- AZELLSBKKCSFGM-LTUMISQWSA-N (3ar,5r,6r,7s,7ar)-2-(dimethylamino)-7-fluoro-5-[(1r)-1-hydroxyethyl]-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazol-6-ol Chemical compound F[C@@H]1[C@H](O)[C@@H]([C@H](O)C)O[C@@H]2SC(N(C)C)=N[C@@H]21 AZELLSBKKCSFGM-LTUMISQWSA-N 0.000 claims description 2
- AZELLSBKKCSFGM-JITZTYRVSA-N (3ar,5r,6r,7s,7ar)-2-(dimethylamino)-7-fluoro-5-[(1s)-1-hydroxyethyl]-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazol-6-ol Chemical compound F[C@@H]1[C@H](O)[C@@H]([C@@H](O)C)O[C@@H]2SC(N(C)C)=N[C@@H]21 AZELLSBKKCSFGM-JITZTYRVSA-N 0.000 claims description 2
- JUBDIOYUYOXOKG-LTUMISQWSA-N (3ar,5r,6r,7s,7ar)-2-(ethylamino)-7-fluoro-5-[(1r)-1-hydroxyethyl]-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazol-6-ol Chemical compound S1C(NCC)=N[C@H]2[C@@H]1O[C@H]([C@@H](C)O)[C@@H](O)[C@H]2F JUBDIOYUYOXOKG-LTUMISQWSA-N 0.000 claims description 2
- JUBDIOYUYOXOKG-JITZTYRVSA-N (3ar,5r,6r,7s,7ar)-2-(ethylamino)-7-fluoro-5-[(1s)-1-hydroxyethyl]-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazol-6-ol Chemical compound S1C(NCC)=N[C@H]2[C@@H]1O[C@H]([C@H](C)O)[C@@H](O)[C@H]2F JUBDIOYUYOXOKG-JITZTYRVSA-N 0.000 claims description 2
- WLJQSLNDQFCZQE-WYVINJBVSA-N (3ar,5r,6r,7s,7ar)-5-[(s)-cyclobutyl(hydroxy)methyl]-7-fluoro-2-(methylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazol-6-ol Chemical compound C1([C@H](O)[C@H]2O[C@H]3[C@@H]([C@@H]([C@@H]2O)F)N=C(S3)NC)CCC1 WLJQSLNDQFCZQE-WYVINJBVSA-N 0.000 claims description 2
- FDPZXDQXJXLILH-KTWSDMTRSA-N (3ar,5r,6r,7s,7ar)-5-[(s)-cyclopentyl(hydroxy)methyl]-7-fluoro-2-(methylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazol-6-ol Chemical compound C1([C@H](O)[C@H]2O[C@H]3[C@@H]([C@@H]([C@@H]2O)F)N=C(S3)NC)CCCC1 FDPZXDQXJXLILH-KTWSDMTRSA-N 0.000 claims description 2
- IVOAADYEBZYJSD-KIOSUUARSA-N (3ar,5r,6r,7s,7ar)-5-[(s)-cyclopropyl(hydroxy)methyl]-7-fluoro-2-(methylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazol-6-ol Chemical compound C1([C@H](O)[C@H]2O[C@H]3[C@@H]([C@@H]([C@@H]2O)F)N=C(S3)NC)CC1 IVOAADYEBZYJSD-KIOSUUARSA-N 0.000 claims description 2
- WRBFXAOTGCXIHN-ANBNMOMCSA-N (3ar,5r,6r,7s,7ar)-7-fluoro-2-(methylamino)-5-[(1s)-3,3,3-trifluoro-1-hydroxypropyl]-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazol-6-ol Chemical compound S1C(NC)=N[C@H]2[C@@H]1O[C@H]([C@@H](O)CC(F)(F)F)[C@@H](O)[C@H]2F WRBFXAOTGCXIHN-ANBNMOMCSA-N 0.000 claims description 2
- DYOCXHLLDLBZHU-PSGKDBJXSA-N (3ar,5r,6r,7s,7ar)-7-fluoro-5-[(1r)-1-hydroxyethyl]-2-(methylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazol-6-ol Chemical compound S1C(NC)=N[C@H]2[C@@H]1O[C@H]([C@@H](C)O)[C@@H](O)[C@H]2F DYOCXHLLDLBZHU-PSGKDBJXSA-N 0.000 claims description 2
- NPOCUQDEGGFPDG-ANBNMOMCSA-N (3ar,5r,6r,7s,7ar)-7-fluoro-5-[(1r)-2-fluoro-1-hydroxyethyl]-2-(methylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazol-6-ol Chemical compound S1C(NC)=N[C@H]2[C@@H]1O[C@H]([C@@H](O)CF)[C@@H](O)[C@H]2F NPOCUQDEGGFPDG-ANBNMOMCSA-N 0.000 claims description 2
- DYOCXHLLDLBZHU-ANBNMOMCSA-N (3ar,5r,6r,7s,7ar)-7-fluoro-5-[(1s)-1-hydroxyethyl]-2-(methylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazol-6-ol Chemical compound S1C(NC)=N[C@H]2[C@@H]1O[C@H]([C@H](C)O)[C@@H](O)[C@H]2F DYOCXHLLDLBZHU-ANBNMOMCSA-N 0.000 claims description 2
- KUNRIBDRTKJULI-ALMWHKAHSA-N (3ar,5r,6r,7s,7ar)-7-fluoro-5-[(1s)-1-hydroxyethyl]-2-pyrrolidin-1-yl-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazol-6-ol Chemical compound S([C@H]1O[C@@H]([C@H]([C@@H](F)[C@H]1N=1)O)[C@@H](O)C)C=1N1CCCC1 KUNRIBDRTKJULI-ALMWHKAHSA-N 0.000 claims description 2
- ATPLWNORUCFDIM-JITZTYRVSA-N (3ar,5r,6r,7s,7ar)-7-fluoro-5-[(1s)-1-hydroxypropyl]-2-(methylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazol-6-ol Chemical compound F[C@@H]1[C@H](O)[C@@H]([C@@H](O)CC)O[C@@H]2SC(NC)=N[C@@H]21 ATPLWNORUCFDIM-JITZTYRVSA-N 0.000 claims description 2
- AKRHTVJJYIYPNW-SYHAXYEDSA-N (3ar,5r,6s,7ar)-2-(dimethylamino)-5-[(1r)-1-hydroxyethyl]-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazol-6-ol Chemical compound C1[C@H](O)[C@@H]([C@H](O)C)O[C@@H]2SC(N(C)C)=N[C@@H]21 AKRHTVJJYIYPNW-SYHAXYEDSA-N 0.000 claims description 2
- AKRHTVJJYIYPNW-KVEIKIFDSA-N (3ar,5r,6s,7ar)-2-(dimethylamino)-5-[(1s)-1-hydroxyethyl]-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazol-6-ol Chemical compound C1[C@H](O)[C@@H]([C@@H](O)C)O[C@@H]2SC(N(C)C)=N[C@@H]21 AKRHTVJJYIYPNW-KVEIKIFDSA-N 0.000 claims description 2
- RDSKELZKZXOPKR-SYHAXYEDSA-N (3ar,5r,6s,7ar)-2-(ethylamino)-5-[(1r)-1-hydroxyethyl]-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazol-6-ol Chemical compound C1[C@H](O)[C@@H]([C@@H](C)O)O[C@@H]2SC(NCC)=N[C@@H]21 RDSKELZKZXOPKR-SYHAXYEDSA-N 0.000 claims description 2
- RDSKELZKZXOPKR-KVEIKIFDSA-N (3ar,5r,6s,7ar)-2-(ethylamino)-5-[(1s)-1-hydroxyethyl]-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazol-6-ol Chemical compound C1[C@H](O)[C@@H]([C@H](C)O)O[C@@H]2SC(NCC)=N[C@@H]21 RDSKELZKZXOPKR-KVEIKIFDSA-N 0.000 claims description 2
- LHPQBKLAIXBHQU-JAJWTYFOSA-N (3ar,5r,6s,7ar)-5-[(1r)-1-hydroxyethyl]-2-(methylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazol-6-ol Chemical compound C1[C@H](O)[C@@H]([C@@H](C)O)O[C@@H]2SC(NC)=N[C@@H]21 LHPQBKLAIXBHQU-JAJWTYFOSA-N 0.000 claims description 2
- LHPQBKLAIXBHQU-BZCSJUTBSA-N (3ar,5r,6s,7ar)-5-[(1s)-1-hydroxyethyl]-2-(methylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazol-6-ol Chemical compound C1[C@H](O)[C@@H]([C@H](C)O)O[C@@H]2SC(NC)=N[C@@H]21 LHPQBKLAIXBHQU-BZCSJUTBSA-N 0.000 claims description 2
- DYOCXHLLDLBZHU-ORBTUSEBSA-N (3ar,5r,6s,7r,7ar)-7-fluoro-5-[(1r)-1-hydroxyethyl]-2-(methylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazol-6-ol Chemical compound S1C(NC)=N[C@H]2[C@@H]1O[C@H]([C@@H](C)O)[C@H](O)[C@@H]2F DYOCXHLLDLBZHU-ORBTUSEBSA-N 0.000 claims description 2
- DYOCXHLLDLBZHU-GUHFPMLUSA-N (3ar,5r,6s,7r,7ar)-7-fluoro-5-[(1s)-1-hydroxyethyl]-2-(methylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazol-6-ol Chemical compound S1C(NC)=N[C@H]2[C@@H]1O[C@H]([C@H](C)O)[C@H](O)[C@@H]2F DYOCXHLLDLBZHU-GUHFPMLUSA-N 0.000 claims description 2
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| AU2009276223B2 (en) | 2008-08-01 | 2015-04-02 | Simon Fraser University | Selective glycosidase inhibitors and uses thereof |
| EP2569291B1 (en) | 2010-05-11 | 2016-04-06 | Simon Fraser University | Selective glycosidase inhibitors and uses thereof |
| EP2638052B1 (en) | 2010-11-08 | 2017-03-22 | Alectos Therapeutics, Inc. | Selective glycosidase inhibitors and uses thereof |
| BR112013016179A2 (pt) | 2010-12-23 | 2018-07-10 | Alectos Therapeutics Inc | inibidores seletivos da glicosidase e usos dos mesmos. |
| WO2012126091A1 (en) | 2011-03-24 | 2012-09-27 | Alectos Therapeutics Inc. | Selective glycosidase inhibitors and uses thereof |
| WO2012129651A1 (en) | 2011-03-31 | 2012-10-04 | Alectos Therapeutics Inc. | Selective glycosidase inhibitors and uses thereof |
| WO2013000084A1 (en) | 2011-06-27 | 2013-01-03 | Alectos Therapeutics Inc. | Selective glycosidase inhibitors and uses thereof |
| US9199949B2 (en) | 2011-06-27 | 2015-12-01 | Alectos Therapeutics Inc. | Selective glycosidase inhibitors and uses thereof |
| WO2013000086A1 (en) | 2011-06-27 | 2013-01-03 | Alectos Therapeutics Inc. | Selective glycosidase inhibitors and uses thereof |
| EP2890676B1 (en) | 2012-08-31 | 2018-12-05 | Alectos Therapeutics Inc. | Glycosidase inhibitors and uses thereof |
| US9809537B2 (en) | 2012-08-31 | 2017-11-07 | Alectos Therapeutics Inc. | Glycosidase inhibitors and uses thereof |
| JP2015534991A (ja) | 2012-10-31 | 2015-12-07 | アレクトス・セラピューティクス・インコーポレイテッド | グリコシダーゼ阻害剤およびその使用 |
| WO2014100934A1 (en) | 2012-12-24 | 2014-07-03 | Merck Sharp & Dohme Corp. | Glycosidase inhibitors and uses thereof |
| CN120796168A (zh) | 2013-06-11 | 2025-10-17 | 哈佛学院校长同事会 | SC-β细胞以及用于产生其的组合物和方法 |
| AR106977A1 (es) * | 2015-12-14 | 2018-03-07 | Amicus Therapeutics Inc | Compuestos para el tratamiento de la enfermedad de alzheimer y/o la angiopatía amiloide cerebral |
| AU2019214048B2 (en) * | 2018-02-01 | 2023-03-16 | Japan Tobacco Inc. | Nitrogenated heterocyclic amide compound, and use thereof for medical purposes |
| GB201907716D0 (en) | 2019-05-31 | 2019-07-17 | Smith & Nephew | Systems and methods for extending operational time of negative pressure wound treatment apparatuses |
| GB202000274D0 (en) | 2020-01-09 | 2020-02-26 | Smith & Nephew | Systems and methods for monitoring operational lifetime of negative pressure wound treatment apparatuses |
| GB202104922D0 (en) | 2021-04-07 | 2021-05-19 | Smith & Nephew | Temperature monitoring and control for negative pressure wound therapy systems |
| CN116322815A (zh) | 2020-10-05 | 2023-06-23 | T.J.史密夫及内修有限公司 | 用于负压伤口疗法系统的温度监测和控制 |
| KR102533471B1 (ko) | 2020-11-23 | 2023-05-19 | (주) 메디프론디비티 | O-GlcNAcase 저해 활성을 갖는 화합물 및 이의 용도 |
| EP4359028A1 (en) | 2021-06-25 | 2024-05-01 | T.J. Smith and Nephew, Limited | Liquid ingress protection and design of electronic circutry for negative pressure wound therapy systems |
| GB202109154D0 (en) | 2021-06-25 | 2021-08-11 | Smith & Nephew | Liquid ingress protection for negative pressure wound therapy systems |
| GB202110240D0 (en) | 2021-07-16 | 2021-09-01 | Smith & Nephew | Reduced pressure apparatuses and methods |
| WO2023131680A1 (en) | 2022-01-10 | 2023-07-13 | T.J.Smith And Nephew,Limited | Temperature detection and protection for negative pressure wound therapy systems |
| WO2023135177A1 (en) | 2022-01-14 | 2023-07-20 | T.J.Smith And Nephew, Limited | Self-calibration with dynamic therapy performance for negative pressure wound therapy devices |
| GB202304922D0 (en) | 2023-04-03 | 2023-05-17 | Smith & Nephew | Printed circuit board configurations for negative pressure wound therapy devices |
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| SU1441749A1 (ru) * | 1987-03-16 | 1996-01-10 | Институт Тонкой Органической Химии Им.А.Л.Мнджояна | 2-АМИНО-5,5-ДИМЕТИЛ-4,5-ДИГИДРО-7Н-ПИРАНО [4,3-d] ТИАЗОЛ, ОБЛАДАЮЩИЙ ТРАНКВИЛИЗИРУЮЩЕЙ АКТИВНОСТЬЮ |
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| JPH07316178A (ja) | 1994-05-25 | 1995-12-05 | Sankyo Co Ltd | 糖アミノオキサゾリン類 |
| JPH09132585A (ja) | 1995-11-10 | 1997-05-20 | Shin Etsu Chem Co Ltd | 新規アミノ糖及びキトオリゴ糖又はその類似オリゴ糖の製造方法 |
| JP4233262B2 (ja) | 2001-03-14 | 2009-03-04 | 生化学工業株式会社 | カルバ糖アミン誘導体及びそれを用いるグリコシダーゼ阻害剤 |
| JP4866515B2 (ja) | 2001-07-02 | 2012-02-01 | 生化学工業株式会社 | 糖オキサゾリン誘導体の製造方法 |
| US20080166323A1 (en) | 2004-04-14 | 2008-07-10 | Uab Research Foundation | Activators of Hexosamine Biosynthesis as Inhibitors of Injury Induced by Ischemia or Hermorrhagic Shock |
| US20080287375A1 (en) | 2005-03-01 | 2008-11-20 | Simon Fraser University | Selective Glycosidase Inhibitors, Methods of Making Inhibitors, and Uses Thereof |
| JP5380293B2 (ja) | 2006-08-31 | 2014-01-08 | サイモン・フレーザー・ユニバーシティ | 選択的グリコシダーゼ阻害剤およびその使用 |
| CN107253970A (zh) | 2006-08-31 | 2017-10-17 | 西蒙·弗雷瑟大学 | 选择性糖苷酶抑制剂及其用途 |
| AU2009276223B2 (en) | 2008-08-01 | 2015-04-02 | Simon Fraser University | Selective glycosidase inhibitors and uses thereof |
| CA2732335A1 (en) | 2008-08-01 | 2010-02-04 | Simon Fraser University | Selective glycosidase inhibitors and uses thereof |
| AU2009299073B2 (en) | 2008-09-16 | 2015-04-02 | Simon Fraser University | Selective glycosidase inhibitors and uses thereof |
| EP2569291B1 (en) | 2010-05-11 | 2016-04-06 | Simon Fraser University | Selective glycosidase inhibitors and uses thereof |
| EP2638052B1 (en) | 2010-11-08 | 2017-03-22 | Alectos Therapeutics, Inc. | Selective glycosidase inhibitors and uses thereof |
| WO2012061971A1 (en) | 2010-11-08 | 2012-05-18 | Alectos Therapeutics Inc. | Selective glycosidase inhibitors and uses thereof |
| TW201249848A (en) * | 2010-11-08 | 2012-12-16 | Merck Sharp & Dohme | Selective glycosidase inhibitors and uses thereof |
| WO2012061972A1 (en) * | 2010-11-08 | 2012-05-18 | Alectos Therapeutics Inc. | Selective glycosidase inhibitors and uses thereof |
| BR112013016179A2 (pt) * | 2010-12-23 | 2018-07-10 | Alectos Therapeutics Inc | inibidores seletivos da glicosidase e usos dos mesmos. |
| GB201103526D0 (en) | 2011-03-02 | 2011-04-13 | Summit Corp Plc | Selective glycosidase inhibitors and uses thereof |
| WO2012126091A1 (en) | 2011-03-24 | 2012-09-27 | Alectos Therapeutics Inc. | Selective glycosidase inhibitors and uses thereof |
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| WO2013000084A1 (en) | 2011-06-27 | 2013-01-03 | Alectos Therapeutics Inc. | Selective glycosidase inhibitors and uses thereof |
| WO2013000086A1 (en) | 2011-06-27 | 2013-01-03 | Alectos Therapeutics Inc. | Selective glycosidase inhibitors and uses thereof |
| US9199949B2 (en) | 2011-06-27 | 2015-12-01 | Alectos Therapeutics Inc. | Selective glycosidase inhibitors and uses thereof |
| EP2744338B1 (en) | 2011-08-18 | 2016-04-27 | Merck Sharp & Dohme Corp. | Selective glycosidase inhibitors and uses thereof |
| CA2845149C (en) | 2011-08-25 | 2019-12-31 | Merck Patent Gmbh | Pyrano[3,2-d] [1,3]thiazole as glycosidase inhibitors |
| EP2847199B1 (en) | 2012-05-08 | 2017-10-25 | Merck Sharp & Dohme Corp. | Permeable glycosidase inhibitors and uses thereof |
| US9809537B2 (en) | 2012-08-31 | 2017-11-07 | Alectos Therapeutics Inc. | Glycosidase inhibitors and uses thereof |
| EP2890676B1 (en) | 2012-08-31 | 2018-12-05 | Alectos Therapeutics Inc. | Glycosidase inhibitors and uses thereof |
| US9522883B2 (en) | 2012-08-31 | 2016-12-20 | Alectos Therapeutics Inc. | Glycosidase inhibitors and uses thereof |
| US20150299122A1 (en) | 2012-08-31 | 2015-10-22 | Alectos Therapeutics Inc. | Glycosidase inhibitors and uses thereof |
| JP2015534991A (ja) | 2012-10-31 | 2015-12-07 | アレクトス・セラピューティクス・インコーポレイテッド | グリコシダーゼ阻害剤およびその使用 |
| WO2014100934A1 (en) | 2012-12-24 | 2014-07-03 | Merck Sharp & Dohme Corp. | Glycosidase inhibitors and uses thereof |
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