JP2013508335A5 - - Google Patents
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- Publication number
- JP2013508335A5 JP2013508335A5 JP2012534672A JP2012534672A JP2013508335A5 JP 2013508335 A5 JP2013508335 A5 JP 2013508335A5 JP 2012534672 A JP2012534672 A JP 2012534672A JP 2012534672 A JP2012534672 A JP 2012534672A JP 2013508335 A5 JP2013508335 A5 JP 2013508335A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- tetrahydro
- pyran
- phenyl
- hydroxymethyl
- 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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- 125000000217 alkyl group Chemical group 0.000 claims 93
- 125000005843 halogen group Chemical group 0.000 claims 44
- 125000000623 heterocyclic group Chemical group 0.000 claims 37
- 150000003839 salts Chemical class 0.000 claims 35
- 125000003118 aryl group Chemical group 0.000 claims 33
- 125000003545 alkoxy group Chemical group 0.000 claims 32
- 150000001875 compounds Chemical class 0.000 claims 32
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 28
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 28
- 125000001424 substituent group Chemical group 0.000 claims 27
- 125000001072 heteroaryl group Chemical group 0.000 claims 26
- -1 chloro, fluoro, hydroxy, methyl Chemical group 0.000 claims 17
- 229910052739 hydrogen Inorganic materials 0.000 claims 15
- 239000001257 hydrogen Substances 0.000 claims 15
- 150000002431 hydrogen Chemical group 0.000 claims 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims 11
- 239000008194 pharmaceutical composition Substances 0.000 claims 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims 8
- 125000004104 aryloxy group Chemical group 0.000 claims 7
- 125000004429 atom Chemical group 0.000 claims 7
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 7
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 7
- 206010012601 diabetes mellitus Diseases 0.000 claims 6
- 125000004043 oxo group Chemical group O=* 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 125000003003 spiro group Chemical group 0.000 claims 6
- 239000000654 additive Substances 0.000 claims 5
- 230000000996 additive effect Effects 0.000 claims 5
- 229910052799 carbon Inorganic materials 0.000 claims 5
- 150000003527 tetrahydropyrans Chemical group 0.000 claims 5
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- BOIWCSUQYQXIIP-DFLSAPQXSA-N (2s,3r,4r,5s,6r)-2-[3-[(4-benzyl-2,3-dihydro-1,4-benzoxazin-6-yl)methyl]-4-chlorophenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1=CC=C(Cl)C(CC=2C=C3N(CC=4C=CC=CC=4)CCOC3=CC=2)=C1 BOIWCSUQYQXIIP-DFLSAPQXSA-N 0.000 claims 2
- JOFXGKBUQVCDAZ-RXFVIIJJSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-3-(spiro[3,4-dihydrochromene-2,1'-cyclopentane]-6-ylmethyl)phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1=CC=C(Cl)C(CC=2C=C3CCC4(CCCC4)OC3=CC=2)=C1 JOFXGKBUQVCDAZ-RXFVIIJJSA-N 0.000 claims 2
- ABADUMLIAZCWJD-UHFFFAOYSA-N 1,3-dioxole Chemical compound C1OC=CO1 ABADUMLIAZCWJD-UHFFFAOYSA-N 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 125000004470 heterocyclooxy group Chemical group 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000002950 monocyclic group Chemical group 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- CXNPIMFZMGOKRZ-YDLBFBONSA-N (2R,3S,4R,5R,6S)-6-[4-chloro-3-[(2,2-dimethyl-3,4-dihydro-1,4-benzoxazin-6-yl)methyl]phenyl]-6-methyloxane-2,3,4,5-tetrol Chemical compound ClC1=C(C=C(C=C1)[C@@]1(O[C@H]([C@H]([C@@H]([C@H]1O)O)O)O)C)CC=1C=CC2=C(NCC(O2)(C)C)C=1 CXNPIMFZMGOKRZ-YDLBFBONSA-N 0.000 claims 1
- MWKNXFDMJURVFM-ZQGJOIPISA-N (2r,3s,4r,5r,6s)-2-(hydroxymethyl)-6-[4-methoxy-3-(1,2,3,4-tetrahydroquinolin-6-ylmethyl)phenyl]oxane-3,4,5-triol Chemical compound C1=C(CC=2C=C3CCCNC3=CC=2)C(OC)=CC=C1[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O MWKNXFDMJURVFM-ZQGJOIPISA-N 0.000 claims 1
- IUYYXBYVTKKXSS-ZQGJOIPISA-N (2r,3s,4r,5r,6s)-2-(hydroxymethyl)-6-[4-methoxy-3-(1,2,3,4-tetrahydroquinolin-7-ylmethyl)phenyl]oxane-3,4,5-triol Chemical compound C1=C(CC=2C=C3NCCCC3=CC=2)C(OC)=CC=C1[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O IUYYXBYVTKKXSS-ZQGJOIPISA-N 0.000 claims 1
- OCPUJUBLDISJNK-RXFVIIJJSA-N (2r,3s,4r,5r,6s)-2-(hydroxymethyl)-6-[4-methoxy-3-(spiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ylmethyl)phenyl]oxane-3,4,5-triol Chemical compound COC1=CC=C([C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)C=C1CC(C=C1CC2)=CC=C1OC12CCC1 OCPUJUBLDISJNK-RXFVIIJJSA-N 0.000 claims 1
- GQSFEZGDYCBNSR-ZQGJOIPISA-N (2r,3s,4r,5r,6s)-2-(hydroxymethyl)-6-[4-methyl-3-(1,2,3,4-tetrahydroquinolin-7-ylmethyl)phenyl]oxane-3,4,5-triol Chemical compound C1=C(CC=2C=C3NCCCC3=CC=2)C(C)=CC=C1[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O GQSFEZGDYCBNSR-ZQGJOIPISA-N 0.000 claims 1
- VNOFFBXXFWYKLQ-RXFVIIJJSA-N (2r,3s,4r,5r,6s)-2-(hydroxymethyl)-6-[4-propan-2-yl-3-(1,2,3,4-tetrahydroquinolin-6-ylmethyl)phenyl]oxane-3,4,5-triol Chemical compound C1=C(CC=2C=C3CCCNC3=CC=2)C(C(C)C)=CC=C1[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O VNOFFBXXFWYKLQ-RXFVIIJJSA-N 0.000 claims 1
- XFJAMQQAAMJFGB-ZQGJOIPISA-N (2s,3r,4r,5s,6r)-2-[3-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-4-ethylphenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C1=C(CC=2C=C3OCCOC3=CC=2)C(CC)=CC=C1[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O XFJAMQQAAMJFGB-ZQGJOIPISA-N 0.000 claims 1
- RUVCJLHNBYZJHZ-BDHVOXNPSA-N (2s,3r,4r,5s,6r)-2-[3-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-4-methoxyphenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C1=C(CC=2C=C3OCCOC3=CC=2)C(OC)=CC=C1[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O RUVCJLHNBYZJHZ-BDHVOXNPSA-N 0.000 claims 1
- IEUXUJIJOYVFAY-ZQGJOIPISA-N (2s,3r,4r,5s,6r)-2-[3-(3,4-dihydro-2h-1,4-benzoxazin-6-ylmethyl)-4-ethylphenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C1=C(CC=2C=C3NCCOC3=CC=2)C(CC)=CC=C1[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O IEUXUJIJOYVFAY-ZQGJOIPISA-N 0.000 claims 1
- MSRYKMIVHLHUSC-BDHVOXNPSA-N (2s,3r,4r,5s,6r)-2-[3-(3,4-dihydro-2h-1,4-benzoxazin-6-ylmethyl)-4-methoxyphenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C1=C(CC=2C=C3NCCOC3=CC=2)C(OC)=CC=C1[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O MSRYKMIVHLHUSC-BDHVOXNPSA-N 0.000 claims 1
- KSOOOXHCWVAMAA-SJSRKZJXSA-N (2s,3r,4r,5s,6r)-2-[3-(3,4-dihydro-2h-1,4-benzoxazin-6-ylmethyl)-4-propan-2-ylphenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C1=C(CC=2C=C3NCCOC3=CC=2)C(C(C)C)=CC=C1[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O KSOOOXHCWVAMAA-SJSRKZJXSA-N 0.000 claims 1
- UVKPLODOGCDGSG-BDHVOXNPSA-N (2s,3r,4r,5s,6r)-2-[3-(3,4-dihydro-2h-chromen-6-ylmethyl)-4-(trifluoromethoxy)phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1=CC=C(OC(F)(F)F)C(CC=2C=C3CCCOC3=CC=2)=C1 UVKPLODOGCDGSG-BDHVOXNPSA-N 0.000 claims 1
- QNNLYRNKHQVOPL-VJLURNNQSA-N (2s,3r,4r,5s,6r)-2-[3-[(1-benzyl-3,4-dihydro-2h-quinolin-7-yl)methyl]-4-propan-2-ylphenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound CC(C)C1=CC=C([C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)C=C1CC(C=C12)=CC=C1CCCN2CC1=CC=CC=C1 QNNLYRNKHQVOPL-VJLURNNQSA-N 0.000 claims 1
- JKXGJIXLTNSXKZ-RQKPWJHBSA-N (2s,3r,4r,5s,6r)-2-[3-[(4-benzyl-2,2-dimethyl-3h-1,4-benzoxazin-6-yl)methyl]-4-chlorophenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C12=CC(CC=3C(=CC=C(C=3)[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O)Cl)=CC=C2OC(C)(C)CN1CC1=CC=CC=C1 JKXGJIXLTNSXKZ-RQKPWJHBSA-N 0.000 claims 1
- IKDUSEGUYUWRGL-SAEUYMBFSA-N (2s,3r,4r,5s,6r)-2-[3-[(4-benzyl-2,3-dihydro-1,4-benzoxazin-6-yl)methyl]-4-propan-2-ylphenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound CC(C)C1=CC=C([C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)C=C1CC(C=C12)=CC=C1OCCN2CC1=CC=CC=C1 IKDUSEGUYUWRGL-SAEUYMBFSA-N 0.000 claims 1
- WRMXDAVTEAMGLW-RQKPWJHBSA-N (2s,3r,4r,5s,6r)-2-[3-[(4-benzylspiro[3h-1,4-benzoxazine-2,1'-cyclopropane]-6-yl)methyl]-4-chlorophenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1=CC=C(Cl)C(CC=2C=C3N(CC=4C=CC=CC=4)CC4(CC4)OC3=CC=2)=C1 WRMXDAVTEAMGLW-RQKPWJHBSA-N 0.000 claims 1
- KUUZKOHHMBXMGE-BDHVOXNPSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-3-(1,2,3,4-tetrahydroisoquinolin-7-ylmethyl)phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1=CC=C(Cl)C(CC=2C=C3CNCCC3=CC=2)=C1 KUUZKOHHMBXMGE-BDHVOXNPSA-N 0.000 claims 1
- XTTIEOZDXAMWBO-BDHVOXNPSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-3-(1,2,3,4-tetrahydroquinolin-7-ylmethyl)phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1=CC=C(Cl)C(CC=2C=C3NCCCC3=CC=2)=C1 XTTIEOZDXAMWBO-BDHVOXNPSA-N 0.000 claims 1
- YMBKJXJZFLKDDI-ADAARDCZSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-3-(2,3-dihydro-1-benzofuran-5-ylmethyl)phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1=CC=C(Cl)C(CC=2C=C3CCOC3=CC=2)=C1 YMBKJXJZFLKDDI-ADAARDCZSA-N 0.000 claims 1
- FTNIERGYEVLCRV-ADAARDCZSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-3-(3,4-dihydro-2h-1,4-benzoxazin-6-ylmethyl)phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1=CC=C(Cl)C(CC=2C=C3NCCOC3=CC=2)=C1 FTNIERGYEVLCRV-ADAARDCZSA-N 0.000 claims 1
- NVHAGBPFTFLYNL-BDHVOXNPSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-3-(spiro[3,4-dihydro-1,4-benzoxazine-2,1'-cyclopropane]-6-ylmethyl)phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1=CC=C(Cl)C(CC=2C=C3NCC4(CC4)OC3=CC=2)=C1 NVHAGBPFTFLYNL-BDHVOXNPSA-N 0.000 claims 1
- YCKYXZOCAFMWQE-SJSRKZJXSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-3-(spiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ylmethyl)phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1=CC=C(Cl)C(CC=2C=C3CCC4(CCC4)OC3=CC=2)=C1 YCKYXZOCAFMWQE-SJSRKZJXSA-N 0.000 claims 1
- UVWJFVUMYXJKLK-SJSRKZJXSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-3-[(4-cyclopropyl-2,3-dihydro-1,4-benzoxazin-7-yl)methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1=CC=C(Cl)C(CC=2C=C3OCCN(C3=CC=2)C2CC2)=C1 UVWJFVUMYXJKLK-SJSRKZJXSA-N 0.000 claims 1
- JKVDIQFAMLCYRL-ZQGJOIPISA-N (2s,3r,4r,5s,6r)-2-[4-chloro-3-[(4-ethyl-2,3-dihydro-1,4-benzoxazin-6-yl)methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C1=C2N(CC)CCOC2=CC=C1CC(C(=CC=1)Cl)=CC=1[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O JKVDIQFAMLCYRL-ZQGJOIPISA-N 0.000 claims 1
- XRNTYSCFJIAWDQ-VUNWFEDTSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-3-[(4-hydroxy-3,4-dihydro-2h-chromen-6-yl)methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1=CC=C(Cl)C(CC=2C=C3C(O)CCOC3=CC=2)=C1 XRNTYSCFJIAWDQ-VUNWFEDTSA-N 0.000 claims 1
- VDMIGDKNMBPOOL-BDHVOXNPSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-3-[(4-methyl-2,3-dihydro-1,4-benzoxazin-6-yl)methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C1=C2N(C)CCOC2=CC=C1CC(C(=CC=1)Cl)=CC=1[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O VDMIGDKNMBPOOL-BDHVOXNPSA-N 0.000 claims 1
- OWJOIZYZAKGOPN-BDHVOXNPSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-3-[(4-methyl-2,3-dihydro-1,4-benzoxazin-7-yl)methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C=1C=C2N(C)CCOC2=CC=1CC(C(=CC=1)Cl)=CC=1[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O OWJOIZYZAKGOPN-BDHVOXNPSA-N 0.000 claims 1
- KQNDZYRBEHYEQA-RLXMVLCYSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-3-[[1-[(4-methoxyphenyl)methyl]-3,4-dihydro-2h-quinolin-6-yl]methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C1=CC(OC)=CC=C1CN1C2=CC=C(CC=3C(=CC=C(C=3)[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O)Cl)C=C2CCC1 KQNDZYRBEHYEQA-RLXMVLCYSA-N 0.000 claims 1
- RRHQFFQLFNUECC-RQKPWJHBSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-3-[[4-[(4-methoxyphenyl)methyl]-2,3-dihydro-1,4-benzoxazin-6-yl]methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C1=CC(OC)=CC=C1CN1C2=CC(CC=3C(=CC=C(C=3)[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O)Cl)=CC=C2OCC1 RRHQFFQLFNUECC-RQKPWJHBSA-N 0.000 claims 1
- JYOHAXKLLUXGRH-SJSRKZJXSA-N (2s,3r,4r,5s,6r)-2-[4-cyclopropyl-3-(3,4-dihydro-2h-1,4-benzoxazin-6-ylmethyl)phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C(C=C1CC=2C=C3NCCOC3=CC=2)=CC=C1C1CC1 JYOHAXKLLUXGRH-SJSRKZJXSA-N 0.000 claims 1
- VDGBFZJBLBGSAP-RXFVIIJJSA-N (2s,3r,4r,5s,6r)-2-[4-cyclopropyl-3-(3,4-dihydro-2h-chromen-6-ylmethyl)phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C(C=C1CC=2C=C3CCCOC3=CC=2)=CC=C1C1CC1 VDGBFZJBLBGSAP-RXFVIIJJSA-N 0.000 claims 1
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical group C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- XVOULZXLKDTKIY-ZQGJOIPISA-N 1-[6-[[2-chloro-5-[(2s,3r,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]phenyl]methyl]-2,3-dihydro-1,4-benzoxazin-4-yl]ethanone Chemical compound C1=C2N(C(=O)C)CCOC2=CC=C1CC(C(=CC=1)Cl)=CC=1[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O XVOULZXLKDTKIY-ZQGJOIPISA-N 0.000 claims 1
- JHUUPUMBZGWODW-UHFFFAOYSA-N 3,6-dihydro-1,2-dioxine Chemical group C1OOCC=C1 JHUUPUMBZGWODW-UHFFFAOYSA-N 0.000 claims 1
- FNGWBNFJBVVODV-ADAARDCZSA-N 6-[[2-chloro-5-[(2s,3r,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]phenyl]methyl]-2,2-dimethyl-4h-1,4-benzoxazin-3-one Chemical compound C1=C2NC(=O)C(C)(C)OC2=CC=C1CC(C(=CC=1)Cl)=CC=1[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O FNGWBNFJBVVODV-ADAARDCZSA-N 0.000 claims 1
- BAAZPPLWASSJBL-BDHVOXNPSA-N 6-[[2-chloro-5-[(2s,3r,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]phenyl]methyl]-2,3-dihydrochromen-4-one Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1=CC=C(Cl)C(CC=2C=C3C(=O)CCOC3=CC=2)=C1 BAAZPPLWASSJBL-BDHVOXNPSA-N 0.000 claims 1
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