JPWO2021028336A5 - - Google Patents
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- Publication number
- JPWO2021028336A5 JPWO2021028336A5 JP2022507725A JP2022507725A JPWO2021028336A5 JP WO2021028336 A5 JPWO2021028336 A5 JP WO2021028336A5 JP 2022507725 A JP2022507725 A JP 2022507725A JP 2022507725 A JP2022507725 A JP 2022507725A JP WO2021028336 A5 JPWO2021028336 A5 JP WO2021028336A5
- Authority
- JP
- Japan
- Prior art keywords
- pyran
- triazol
- methyl
- thio
- tetrahydro
- 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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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 67
- -1 tetrahydro-2H-pyran-4,4-diyl Chemical group 0.000 claims 50
- 125000001424 substituent group Chemical group 0.000 claims 19
- BHDLTOUYJMTTTM-UHFFFAOYSA-N oxan-3-ol Chemical compound OC1CCCOC1 BHDLTOUYJMTTTM-UHFFFAOYSA-N 0.000 claims 17
- ZUSWDTWYONAOPH-UHFFFAOYSA-N [2-(trifluoromethyl)phenyl]hydrazine;hydrochloride Chemical group [Cl-].[NH3+]NC1=CC=CC=C1C(F)(F)F ZUSWDTWYONAOPH-UHFFFAOYSA-N 0.000 claims 15
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 15
- 150000001875 compounds Chemical class 0.000 claims 14
- 150000003839 salts Chemical class 0.000 claims 12
- 229910052736 halogen Inorganic materials 0.000 claims 11
- 150000002367 halogens Chemical class 0.000 claims 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 10
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 6
- 229910052799 carbon Inorganic materials 0.000 claims 5
- 125000004432 carbon atom Chemical group C* 0.000 claims 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 150000002009 diols Chemical class 0.000 claims 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 4
- 208000024172 Cardiovascular disease Diseases 0.000 claims 4
- 208000018522 Gastrointestinal disease Diseases 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- 208000035475 disorder Diseases 0.000 claims 3
- 125000001153 fluoro group Chemical group F* 0.000 claims 3
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 2
- 208000009304 Acute Kidney Injury Diseases 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 208000023275 Autoimmune disease Diseases 0.000 claims 2
- 208000029523 Interstitial Lung disease Diseases 0.000 claims 2
- 208000019693 Lung disease Diseases 0.000 claims 2
- 208000016222 Pancreatic disease Diseases 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- 208000033626 Renal failure acute Diseases 0.000 claims 2
- 201000011040 acute kidney failure Diseases 0.000 claims 2
- 208000020832 chronic kidney disease Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 208000027866 inflammatory disease Diseases 0.000 claims 2
- 230000002757 inflammatory effect Effects 0.000 claims 2
- 208000019423 liver disease Diseases 0.000 claims 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- BUGOPWGPQGYYGR-UHFFFAOYSA-N thiane 1,1-dioxide Chemical compound O=S1(=O)CCCCC1 BUGOPWGPQGYYGR-UHFFFAOYSA-N 0.000 claims 2
- RWVAINKLJZNRAP-PIYILYQRSA-N (2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-[(1R)-2-hydroxy-2-methyl-1-(3,5,6-trimethylpyrazin-2-yl)propyl]sulfanyl-4-[4-(3,4,5-trifluorophenyl)triazol-1-yl]oxane-3,5-diol Chemical compound OC([C@@H](C1=NC(=C(N=C1C)C)C)S[C@@H]1O[C@@H]([C@@H]([C@@H]([C@H]1O)N1N=NC(=C1)C1=CC(=C(C(=C1)F)F)F)O)CO)(C)C RWVAINKLJZNRAP-PIYILYQRSA-N 0.000 claims 1
- IHFJDOKDEMDMPK-QKEDNXFGSA-N (2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-[(1R)-2-hydroxy-2-methyl-1-(4-methylthiophen-3-yl)propyl]sulfanyl-4-[4-(3,4,5-trifluorophenyl)triazol-1-yl]oxane-3,5-diol Chemical compound OC([C@@H](C1=CSC=C1C)S[C@@H]1O[C@@H]([C@@H]([C@@H]([C@H]1O)N1N=NC(=C1)C1=CC(=C(C(=C1)F)F)F)O)CO)(C)C IHFJDOKDEMDMPK-QKEDNXFGSA-N 0.000 claims 1
- VCUAXODKLDNVTA-CCUOSZMHSA-N (2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-[(1R)-2-hydroxy-2-methyl-1-[2-(2-methylpropyl)phenyl]propyl]sulfanyl-4-[4-(3,4,5-trifluorophenyl)triazol-1-yl]oxane-3,5-diol Chemical compound OC([C@@H](C1=C(C=CC=C1)CC(C)C)S[C@@H]1O[C@@H]([C@@H]([C@@H]([C@H]1O)N1N=NC(=C1)C1=CC(=C(C(=C1)F)F)F)O)CO)(C)C VCUAXODKLDNVTA-CCUOSZMHSA-N 0.000 claims 1
- UXYQSSOTPZPFQU-ARQYYYJSSA-N (2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-[(1R)-2-hydroxy-2-methyl-1-[2-(trifluoromethyl)phenyl]propyl]sulfanyl-4-[4-(3,4,5-trifluorophenyl)triazol-1-yl]oxane-3,5-diol Chemical compound OC([C@@H](C1=C(C=CC=C1)C(F)(F)F)S[C@@H]1O[C@@H]([C@@H]([C@@H]([C@H]1O)N1N=NC(=C1)C1=CC(=C(C(=C1)F)F)F)O)CO)(C)C UXYQSSOTPZPFQU-ARQYYYJSSA-N 0.000 claims 1
- ZVTTYXUKQGMTDA-TUFAUPKWSA-N (2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-[(1R,2S)-2-hydroxy-1-[2-(trifluoromethyl)phenyl]butyl]sulfanyl-4-[4-(3,4,5-trifluorophenyl)triazol-1-yl]oxane-3,5-diol Chemical compound O[C@H]([C@@H](C1=C(C=CC=C1)C(F)(F)F)S[C@@H]1O[C@@H]([C@@H]([C@@H]([C@H]1O)N1N=NC(=C1)C1=CC(=C(C(=C1)F)F)F)O)CO)CC ZVTTYXUKQGMTDA-TUFAUPKWSA-N 0.000 claims 1
- OMTAZSIELSHOQY-HCRCWBKNSA-N (2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-[(R)-(4-hydroxyoxan-4-yl)-[2-(trifluoromethyl)phenyl]methyl]sulfanyl-4-[4-(3,4,5-trifluorophenyl)triazol-1-yl]oxane-3,5-diol Chemical compound OC[C@H]1O[C@H]([C@@H]([C@H]([C@H]1O)N1N=NC(=C1)C1=CC(=C(C(=C1)F)F)F)O)S[C@H](C1=C(C=CC=C1)C(F)(F)F)C1(CCOCC1)O OMTAZSIELSHOQY-HCRCWBKNSA-N 0.000 claims 1
- MWQPPBAGYPLFPF-HCRCWBKNSA-N (2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-[(R)-(4-hydroxypiperidin-4-yl)-[2-(trifluoromethyl)phenyl]methyl]sulfanyl-4-[4-(3,4,5-trifluorophenyl)triazol-1-yl]oxane-3,5-diol Chemical compound OC[C@H]1O[C@H]([C@@H]([C@H]([C@H]1O)N1N=NC(=C1)C1=CC(=C(C(=C1)F)F)F)O)S[C@H](C1=C(C=CC=C1)C(F)(F)F)C1(CCNCC1)O MWQPPBAGYPLFPF-HCRCWBKNSA-N 0.000 claims 1
- NDCUFUOVKZGBTA-IXLLXOEKSA-N (2R,3R,4S,5R,6S)-6-[(R)-(1-hydroxycyclohexyl)-[3-(trifluoromethyl)pyridin-2-yl]methyl]sulfanyl-2-(hydroxymethyl)-5-methoxy-4-[4-(3,4,5-trifluorophenyl)triazol-1-yl]oxan-3-ol Chemical compound OC1(CCCCC1)[C@H](S[C@H]1[C@@H]([C@H]([C@H]([C@H](O1)CO)O)N1N=NC(=C1)C1=CC(=C(C(=C1)F)F)F)OC)C1=NC=CC=C1C(F)(F)F NDCUFUOVKZGBTA-IXLLXOEKSA-N 0.000 claims 1
- ZCMYCQOLFBSHRZ-MXEMPPLSSA-N (2R,3R,4S,5R,6S)-6-[(R)-(3-chloropyrazin-2-yl)-(4,4-difluoro-1-hydroxycyclohexyl)methyl]sulfanyl-2-(hydroxymethyl)-5-methoxy-4-[4-(3,4,5-trifluorophenyl)triazol-1-yl]oxan-3-ol Chemical compound ClC=1C(=NC=CN=1)[C@@H](S[C@H]1[C@@H]([C@H]([C@H]([C@H](O1)CO)O)N1N=NC(=C1)C1=CC(=C(C(=C1)F)F)F)OC)C1(CCC(CC1)(F)F)O ZCMYCQOLFBSHRZ-MXEMPPLSSA-N 0.000 claims 1
- HEAHGFKBVBBTBI-RKVUVZGQSA-N (2R,3R,4S,5R,6S)-6-[(R)-(4,4-difluoro-1-hydroxycyclohexyl)-(3-methylpyridin-2-yl)methyl]sulfanyl-2-(hydroxymethyl)-5-methoxy-4-[4-(2,3,4-trifluorophenyl)triazol-1-yl]oxan-3-ol Chemical compound FC1(CCC(CC1)(O)[C@H](S[C@H]1[C@@H]([C@H]([C@H]([C@H](O1)CO)O)N1N=NC(=C1)C1=C(C(=C(C=C1)F)F)F)OC)C1=NC=CC=C1C)F HEAHGFKBVBBTBI-RKVUVZGQSA-N 0.000 claims 1
- KCOWHCDRLIWHMC-PIYILYQRSA-N (2R,3R,4S,5R,6S)-6-[(R)-(4,4-difluoro-1-hydroxycyclohexyl)-(4-methyl-1,2-oxazol-3-yl)methyl]sulfanyl-2-(hydroxymethyl)-5-methoxy-4-[4-(3,4,5-trifluorophenyl)triazol-1-yl]oxan-3-ol Chemical compound FC1(CCC(CC1)(O)[C@H](S[C@H]1[C@@H]([C@H]([C@H]([C@H](O1)CO)O)N1N=NC(=C1)C1=CC(=C(C(=C1)F)F)F)OC)C1=NOC=C1C)F KCOWHCDRLIWHMC-PIYILYQRSA-N 0.000 claims 1
- IXFHANIKWLCTHH-DYRNCQFLSA-N (2S,3R,4S,5R,6R)-2-[(1R)-1-(3,5-dimethyl-1,2-oxazol-4-yl)-2-hydroxy-2-methylpropyl]sulfanyl-6-(hydroxymethyl)-4-[4-(3,4,5-trifluorophenyl)triazol-1-yl]oxane-3,5-diol Chemical compound CC1=NOC(=C1[C@H](C(C)(C)O)S[C@@H]1O[C@@H]([C@@H]([C@@H]([C@H]1O)N1N=NC(=C1)C1=CC(=C(C(=C1)F)F)F)O)CO)C IXFHANIKWLCTHH-DYRNCQFLSA-N 0.000 claims 1
- JJZPDIJDTAPLKD-WWJMMCNDSA-N (2S,3R,4S,5R,6R)-2-[(R)-(1-hydroxy-3,3-dimethylcyclobutyl)-(2-methylphenyl)methyl]sulfanyl-6-(hydroxymethyl)-4-[4-(3,4,5-trifluorophenyl)triazol-1-yl]oxane-3,5-diol Chemical compound OC1(CC(C1)(C)C)[C@H](S[C@@H]1O[C@@H]([C@@H]([C@@H]([C@H]1O)N1N=NC(=C1)C1=CC(=C(C(=C1)F)F)F)O)CO)C1=C(C=CC=C1)C JJZPDIJDTAPLKD-WWJMMCNDSA-N 0.000 claims 1
- URNHDQNEVNGJOB-CCUOSZMHSA-N (2S,3R,4S,5R,6R)-2-[(R)-(1-hydroxycyclohexyl)-(2-methylphenyl)methyl]sulfanyl-6-(hydroxymethyl)-4-[4-(3,4,5-trifluorophenyl)triazol-1-yl]oxane-3,5-diol Chemical compound OC1(CCCCC1)[C@H](S[C@@H]1O[C@@H]([C@@H]([C@@H]([C@H]1O)N1N=NC(=C1)C1=CC(=C(C(=C1)F)F)F)O)CO)C1=C(C=CC=C1)C URNHDQNEVNGJOB-CCUOSZMHSA-N 0.000 claims 1
- CIGFKUJDPVQRDL-PIYILYQRSA-N (2S,3R,4S,5R,6R)-2-[(R)-(1-hydroxycyclopentyl)-[3-(trifluoromethyl)pyridin-2-yl]methyl]sulfanyl-6-(hydroxymethyl)-4-[4-(3,4,5-trifluorophenyl)triazol-1-yl]oxane-3,5-diol Chemical compound OC1(CCCC1)[C@H](S[C@@H]1O[C@@H]([C@@H]([C@@H]([C@H]1O)N1N=NC(=C1)C1=CC(=C(C(=C1)F)F)F)O)CO)C1=NC=CC=C1C(F)(F)F CIGFKUJDPVQRDL-PIYILYQRSA-N 0.000 claims 1
- MRXLXSNWYYFUEC-ARQYYYJSSA-N (2S,3R,4S,5R,6R)-2-[(R)-(3,3-difluoro-1-hydroxycyclobutyl)-[2-(trifluoromethyl)phenyl]methyl]sulfanyl-6-(hydroxymethyl)-4-[4-(3,4,5-trifluorophenyl)triazol-1-yl]oxane-3,5-diol Chemical compound FC1(CC(C1)(O)[C@H](S[C@@H]1O[C@@H]([C@@H]([C@@H]([C@H]1O)N1N=NC(=C1)C1=CC(=C(C(=C1)F)F)F)O)CO)C1=C(C=CC=C1)C(F)(F)F)F MRXLXSNWYYFUEC-ARQYYYJSSA-N 0.000 claims 1
- IZMODIXZHBQMGN-SUVLSFNQSA-N (2S,3R,4S,5R,6R)-2-[(R)-(4,4-difluoro-1-hydroxycyclohexyl)-(3-methylpyridin-2-yl)methyl]sulfanyl-6-(hydroxymethyl)-4-[4-(3,4,5-trifluorophenyl)triazol-1-yl]oxane-3,5-diol Chemical compound FC1(CCC(CC1)(O)[C@H](S[C@@H]1O[C@@H]([C@@H]([C@@H]([C@H]1O)N1N=NC(=C1)C1=CC(=C(C(=C1)F)F)F)O)CO)C1=NC=CC=C1C)F IZMODIXZHBQMGN-SUVLSFNQSA-N 0.000 claims 1
- JHGAFKHUAZYRCY-PIYILYQRSA-N (2S,3R,4S,5R,6R)-2-[(R)-(4,4-difluoro-1-hydroxycyclohexyl)-(4-methylpyridazin-3-yl)methyl]sulfanyl-6-(hydroxymethyl)-4-[4-(3,4,5-trifluorophenyl)triazol-1-yl]oxane-3,5-diol Chemical compound FC1(CCC(CC1)(O)[C@H](S[C@@H]1O[C@@H]([C@@H]([C@@H]([C@H]1O)N1N=NC(=C1)C1=CC(=C(C(=C1)F)F)F)O)CO)C=1N=NC=CC=1C)F JHGAFKHUAZYRCY-PIYILYQRSA-N 0.000 claims 1
- YCMXGDOUAVBIIP-RUZUSBSMSA-N (2S,3R,4S,5R,6R)-2-[(R)-[(2R,3R)-1-hydroxy-2,3-dimethylcyclobutyl]-(2-methylphenyl)methyl]sulfanyl-6-(hydroxymethyl)-4-[4-(3,4,5-trifluorophenyl)triazol-1-yl]oxane-3,5-diol Chemical compound OC1([C@@H]([C@@H](C1)C)C)[C@H](S[C@@H]1O[C@@H]([C@@H]([C@@H]([C@H]1O)N1N=NC(=C1)C1=CC(=C(C(=C1)F)F)F)O)CO)C1=C(C=CC=C1)C YCMXGDOUAVBIIP-RUZUSBSMSA-N 0.000 claims 1
- KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical group C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 claims 1
- CDRCCUUIHFOAGV-WWJMMCNDSA-N BrC1=C(C=C(C=C1)C=1N=NN(C=1)[C@H]1[C@H]([C@H](O[C@H]([C@@H]1OC)S[C@H](C1=NC=CC=C1C)C1(CCC(CC1)(F)F)O)CO)O)F Chemical compound BrC1=C(C=C(C=C1)C=1N=NN(C=1)[C@H]1[C@H]([C@H](O[C@H]([C@@H]1OC)S[C@H](C1=NC=CC=C1C)C1(CCC(CC1)(F)F)O)CO)O)F CDRCCUUIHFOAGV-WWJMMCNDSA-N 0.000 claims 1
- XYAZFHUFNFFRDL-WTGKAQRQSA-N BrC1=C(C=CC=C1)[C@H](CO)S[C@@H]1O[C@@H]([C@@H]([C@@H]([C@H]1O)N1N=NC(=C1)C1=CC(=C(C(=C1)F)F)F)O)CO Chemical compound BrC1=C(C=CC=C1)[C@H](CO)S[C@@H]1O[C@@H]([C@@H]([C@@H]([C@H]1O)N1N=NC(=C1)C1=CC(=C(C(=C1)F)F)F)O)CO XYAZFHUFNFFRDL-WTGKAQRQSA-N 0.000 claims 1
- YEQKHJOSZVGPDE-ARQYYYJSSA-N C(C)C([C@@H](C=1C(=NOC=1)C)S[C@@H]1O[C@@H]([C@@H]([C@@H]([C@H]1O)N1N=NC(=C1)C1=CC(=C(C(=C1)F)F)F)O)CO)(CC)O Chemical compound C(C)C([C@@H](C=1C(=NOC=1)C)S[C@@H]1O[C@@H]([C@@H]([C@@H]([C@H]1O)N1N=NC(=C1)C1=CC(=C(C(=C1)F)F)F)O)CO)(CC)O YEQKHJOSZVGPDE-ARQYYYJSSA-N 0.000 claims 1
- DHEABPUFHXGQJB-HCRCWBKNSA-N C(C)C1=C(C=CC=C1)[C@H](C(C)(C)O)S[C@@H]1O[C@@H]([C@@H]([C@@H]([C@H]1O)N1N=NC(=C1)C1=CC(=C(C(=C1)F)F)F)O)CO Chemical compound C(C)C1=C(C=CC=C1)[C@H](C(C)(C)O)S[C@@H]1O[C@@H]([C@@H]([C@@H]([C@H]1O)N1N=NC(=C1)C1=CC(=C(C(=C1)F)F)F)O)CO DHEABPUFHXGQJB-HCRCWBKNSA-N 0.000 claims 1
- KYJFFRQAMGUMCP-WIBPYNGWSA-N C1(=C(C=CC=C1)[C@H](C(C)(C)O)S[C@@H]1O[C@@H]([C@@H]([C@@H]([C@H]1O)N1N=NC(=C1)C1=CC(=C(C(=C1)F)F)F)O)CO)C1=CC=CC=C1 Chemical compound C1(=C(C=CC=C1)[C@H](C(C)(C)O)S[C@@H]1O[C@@H]([C@@H]([C@@H]([C@H]1O)N1N=NC(=C1)C1=CC(=C(C(=C1)F)F)F)O)CO)C1=CC=CC=C1 KYJFFRQAMGUMCP-WIBPYNGWSA-N 0.000 claims 1
- YEKATUZSHNIHKQ-BEZHJQARSA-N C1(CC1)C1=C(C(=NO1)C)[C@@H](S[C@@H]1O[C@@H]([C@@H]([C@@H]([C@H]1O)N1N=NC(=C1)C1=CC(=C(C(=C1)F)F)F)O)CO)C1(CCCCC1)O Chemical compound C1(CC1)C1=C(C(=NO1)C)[C@@H](S[C@@H]1O[C@@H]([C@@H]([C@@H]([C@H]1O)N1N=NC(=C1)C1=CC(=C(C(=C1)F)F)F)O)CO)C1(CCCCC1)O YEKATUZSHNIHKQ-BEZHJQARSA-N 0.000 claims 1
- HZFDOXFDIQICHC-GZNZYZJMSA-N C1(CC1)C1=C(C(=NO1)C)[C@@H](S[C@H]1[C@@H]([C@H]([C@H]([C@H](O1)CO)O)N1N=NC(=C1)C1=CC(=C(C(=C1)F)F)F)OC)C1(CCCCC1)O Chemical compound C1(CC1)C1=C(C(=NO1)C)[C@@H](S[C@H]1[C@@H]([C@H]([C@H]([C@H](O1)CO)O)N1N=NC(=C1)C1=CC(=C(C(=C1)F)F)F)OC)C1(CCCCC1)O HZFDOXFDIQICHC-GZNZYZJMSA-N 0.000 claims 1
- WDWOQFCPKPBHHP-ZPYPPCPKSA-N C1(CC1)C1=C(C=CC=C1)[C@@H](S[C@@H]1O[C@@H]([C@@H]([C@@H]([C@H]1O)N1N=NC(=C1)C1=CC(=C(C(=C1)F)F)F)O)CO)C1(CCC(CC1)(F)F)O Chemical compound C1(CC1)C1=C(C=CC=C1)[C@@H](S[C@@H]1O[C@@H]([C@@H]([C@@H]([C@H]1O)N1N=NC(=C1)C1=CC(=C(C(=C1)F)F)F)O)CO)C1(CCC(CC1)(F)F)O WDWOQFCPKPBHHP-ZPYPPCPKSA-N 0.000 claims 1
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| JP2022508719A (ja) | 2018-10-15 | 2022-01-19 | ガレクト バイオテック エービー | ガレクチンのガラクトシド阻害剤のプロドラッグ |
| CN113366007A (zh) | 2018-10-15 | 2021-09-07 | 格莱克特生物技术公司 | 半乳糖凝集素的半乳糖苷抑制剂 |
| JP7486484B2 (ja) | 2018-11-21 | 2024-05-17 | ガレクト バイオテック エービー | ガレクチンのα－Ｄ－ガラクトシド阻害剤 |
| EP3953349A1 (en) | 2019-04-10 | 2022-02-16 | Bristol-Myers Squibb Company | Small molecule inhibitors of galectin-3 |
| CA3141436A1 (en) | 2019-07-03 | 2021-01-07 | Fredrik Zetterberg | Novel galactoside inhibitor of galectins |
| CN114450282A (zh) | 2019-07-05 | 2022-05-06 | 格莱克特生物技术公司 | 半乳糖凝集素的新型半乳糖苷抑制剂 |
| EP4010348B1 (en) | 2019-08-09 | 2023-12-20 | Idorsia Pharmaceuticals Ltd | (2-acetamidyl)thio-beta-d-galactopyranoside derivatives |
| JP7604457B2 (ja) | 2019-08-15 | 2024-12-23 | イドルシア・ファーマシューティカルズ・リミテッド | ２－ヒドロキシシクロアルカン－１－カルバモイル誘導体 |
| CA3148365A1 (en) | 2019-08-29 | 2021-03-04 | Martin Bolli | Alpha-d-galactopyranoside derivatives |
| ES3014851T3 (en) | 2020-10-06 | 2025-04-25 | Idorsia Pharmaceuticals Ltd | Spiro derivatives of alpha-d-galactopyranosides |
| KR20230104190A (ko) | 2020-11-02 | 2023-07-07 | 이도르시아 파마슈티컬스 리미티드 | 갈렉틴-3 억제 2-히드록시시클로알칸-1-카르바모일 유도체 |
| KR20230145111A (ko) | 2021-02-09 | 2023-10-17 | 이도르시아 파마슈티컬스 리미티드 | 히드록시헤테로시클로알칸-카르바모일 유도체 |
| PL4301748T3 (pl) | 2021-03-03 | 2025-09-08 | Idorsia Pharmaceuticals Ltd | Triazolilo-metylo podstawione pochodne alfa-d-galaktopiranozydu |
-
2020
- 2020-08-07 CN CN202080056681.7A patent/CN114206893A/zh active Pending
- 2020-08-07 US US17/633,895 patent/US12404295B2/en active Active
- 2020-08-07 WO PCT/EP2020/072238 patent/WO2021028336A1/en not_active Ceased
- 2020-08-07 EP EP20751158.5A patent/EP4010076B1/en active Active
- 2020-08-07 ES ES20751158T patent/ES2972509T3/es active Active
- 2020-08-07 CA CA3147082A patent/CA3147082A1/en active Pending
- 2020-08-07 JP JP2022507725A patent/JP7612662B2/ja active Active
- 2020-08-07 KR KR1020227007509A patent/KR102854071B1/ko active Active
- 2020-08-07 TW TW109126972A patent/TWI873165B/zh active
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