JP5384744B2 - グリコシド誘導体およびその使用 - Google Patents

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Publication number

JP5384744B2

JP5384744B2 JP2012534672A JP2012534672A JP5384744B2 JP 5384744 B2 JP5384744 B2 JP 5384744B2 JP 2012534672 A JP2012534672 A JP 2012534672A JP 2012534672 A JP2012534672 A JP 2012534672A JP 5384744 B2 JP5384744 B2 JP 5384744B2

Authority

JP

Japan

Prior art keywords

tetrahydro

pyran

phenyl

ylmethyl

hydroxymethyl

Prior art date

2009-10-20

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.)

Expired - Fee Related

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• 229930182470 glycoside Natural products 0.000 title description 3
• 150000002338 glycosides Chemical class 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims description 242
• -1 2H-benzo [1,4] oxazin-7-ylmethyl Chemical group 0.000 claims description 153
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 68
• 150000003839 salts Chemical class 0.000 claims description 63
• 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 description 42
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 42
• 238000011282 treatment Methods 0.000 claims description 37
• 201000010099 disease Diseases 0.000 claims description 35
• 239000008103 glucose Substances 0.000 claims description 28
• 206010012601 diabetes mellitus Diseases 0.000 claims description 23
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 23
• 239000011734 sodium Substances 0.000 claims description 20
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 18
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
• 229910052708 sodium Inorganic materials 0.000 claims description 17
• 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 description 16
• 239000000654 additive Substances 0.000 claims description 16
• 230000001404 mediated effect Effects 0.000 claims description 15
• 239000008194 pharmaceutical composition Substances 0.000 claims description 15
• 125000003003 spiro group Chemical group 0.000 claims description 15
• YNCHESVKDKRUDJ-SJSRKZJXSA-N (2s,3r,4r,5s,6r)-2-[4-cyclopropyl-3-(2,3-dihydro-1,4-benzodioxin-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=C3OCCOC3=CC=2)=CC=C1C1CC1 YNCHESVKDKRUDJ-SJSRKZJXSA-N 0.000 claims description 14
• 150000002148 esters Chemical class 0.000 claims description 14
• 206010022489 Insulin Resistance Diseases 0.000 claims description 12
• 102000034534 Cotransporters Human genes 0.000 claims description 11
• 108020003264 Cotransporters Proteins 0.000 claims description 11
• 208000008589 Obesity Diseases 0.000 claims description 11
• 235000020824 obesity Nutrition 0.000 claims description 11
• 230000000996 additive effect Effects 0.000 claims description 10
• 201000001421 hyperglycemia Diseases 0.000 claims description 6
• 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 description 5
• 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 description 5
• 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 description 5
• 208000032928 Dyslipidaemia Diseases 0.000 claims description 5
• 206010020772 Hypertension Diseases 0.000 claims description 5
• 208000017170 Lipid metabolism disease Diseases 0.000 claims description 5
• 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 description 4
• 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 description 4
• 241000124008 Mammalia Species 0.000 claims description 4
• KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 4
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
• DIXJYYPYYYQVJQ-AVGHQTNXSA-N methyl 6-[[2-chloro-5-[(2s,3r,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]phenyl]methyl]-3,4-dihydro-2h-1,4-benzoxazine-2-carboxylate Chemical compound C=1C=C2OC(C(=O)OC)CNC2=CC=1CC(C(=CC=1)Cl)=CC=1[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O DIXJYYPYYYQVJQ-AVGHQTNXSA-N 0.000 claims description 4
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
• 208000011580 syndromic disease Diseases 0.000 claims description 4
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• MZSXGYZCLGHHIZ-AOALBDIGSA-N 6-[[2-chloro-5-[(2s,3r,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]phenyl]methyl]-3,4-dihydro-2h-1,4-benzoxazine-2-carbonitrile 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=C3NCC(OC3=CC=2)C#N)=C1 MZSXGYZCLGHHIZ-AOALBDIGSA-N 0.000 claims description 3
• 206010027525 Microalbuminuria Diseases 0.000 claims description 3
• 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
• 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 description 2
• 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 description 2
• YMNIFHGEVXFRRB-DFLSAPQXSA-N (2s,3r,4r,5s,6r)-2-[3-(3,4-dihydro-2h-1,4-benzoxazin-6-ylmethyl)-4-(4-methylphenyl)phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C1=CC(C)=CC=C1C1=CC=C([C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)C=C1CC1=CC=C(OCCN2)C2=C1 YMNIFHGEVXFRRB-DFLSAPQXSA-N 0.000 claims description 2
• DVKUSDXNSFOFKS-ADAARDCZSA-N (2s,3r,4r,5s,6r)-2-[3-(3,4-dihydro-2h-1,4-benzoxazin-6-ylmethyl)-4-fluorophenyl]-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(F)C(CC=2C=C3NCCOC3=CC=2)=C1 DVKUSDXNSFOFKS-ADAARDCZSA-N 0.000 claims description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• PVTXJGJDOHYFOX-UHFFFAOYSA-N 2h-1,4-benzoxazine Chemical compound C1=CC=C2N=CCOC2=C1 PVTXJGJDOHYFOX-UHFFFAOYSA-N 0.000 claims description 2
• YHWMFDLNZGIJSD-UHFFFAOYSA-N 2h-1,4-oxazine Chemical compound C1OC=CN=C1 YHWMFDLNZGIJSD-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• FSRJARNFARVFPC-BDHVOXNPSA-N 6-[[2-chloro-5-[(2s,3r,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]phenyl]methyl]chromen-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)C=COC3=CC=2)=C1 FSRJARNFARVFPC-BDHVOXNPSA-N 0.000 claims description 2
• FBHUAAQASTXZAS-RXFVIIJJSA-N 6-[[2-chloro-5-[(2s,3r,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]phenyl]methyl]spiro[3h-chromene-2,4'-piperidine]-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)CC4(CCNCC4)OC3=CC=2)=C1 FBHUAAQASTXZAS-RXFVIIJJSA-N 0.000 claims description 2
• ZECVUQDNEANOBO-LUTHVSDMSA-N [(2r,3r,4r,5s)-3,4,5-triacetyloxy-6-[3-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-4-ethylphenyl]oxan-2-yl]methyl acetate Chemical compound C1=C(CC=2C=C3OCCOC3=CC=2)C(CC)=CC=C1C1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O ZECVUQDNEANOBO-LUTHVSDMSA-N 0.000 claims description 2
• WGTFHBOPFPZZFH-BXZFMWHFSA-N [(2r,3r,4r,5s)-3,4,5-triacetyloxy-6-[4-cyclopropyl-3-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)phenyl]oxan-2-yl]methyl acetate Chemical compound CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(=O)C)OC1C(C=C1CC=2C=C3OCCOC3=CC=2)=CC=C1C1CC1 WGTFHBOPFPZZFH-BXZFMWHFSA-N 0.000 claims description 2
• VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical compound C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 claims description 2
• POCFBDFTJMJWLG-UHFFFAOYSA-N dihydrosinapic acid methyl ester Natural products COC(=O)CCC1=CC(OC)=C(O)C(OC)=C1 POCFBDFTJMJWLG-UHFFFAOYSA-N 0.000 claims description 2
• PWDJCVFKMIQLDE-ZQGJOIPISA-N ethyl 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-benzoxazine-4-carboxylate Chemical compound C1=C2N(C(=O)OCC)CCOC2=CC=C1CC(C(=CC=1)Cl)=CC=1[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O PWDJCVFKMIQLDE-ZQGJOIPISA-N 0.000 claims description 2
• XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims 2
• 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
• 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
• WKVLZIFCTJQOME-RQKPWJHBSA-N (2s,3r,4r,5s,6r)-2-[3-[(2-benzyl-3,4-dihydro-1h-isoquinolin-7-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=C3CN(CC=4C=CC=CC=4)CCC3=CC=2)=C1 WKVLZIFCTJQOME-RQKPWJHBSA-N 0.000 claims 1
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