JP2013508335A5 - - Google Patents
Download PDFInfo
- 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
Links
- 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
- 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 1
- MXOIJFQMEOPURY-RQXATKFSSA-N 6-[[2-chloro-5-[(2s,3r,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]phenyl]methyl]-4h-1,4-benzoxazin-3-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=C3NC(=O)COC3=CC=2)=C1 MXOIJFQMEOPURY-RQXATKFSSA-N 0.000 claims 1
- 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 1
- RXBYZHBPWFNHJO-RQXATKFSSA-N 7-[[2-chloro-5-[(2s,3r,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]phenyl]methyl]-4h-1,4-benzoxazin-3-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=C3OCC(=O)NC3=CC=2)=C1 RXBYZHBPWFNHJO-RQXATKFSSA-N 0.000 claims 1
- 102000034534 Cotransporters Human genes 0.000 claims 1
- 108020003264 Cotransporters Proteins 0.000 claims 1
- 208000032928 Dyslipidaemia Diseases 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- 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 1
- 206010022489 Insulin Resistance Diseases 0.000 claims 1
- 208000017170 Lipid metabolism disease Diseases 0.000 claims 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims 1
- 239000004472 Lysine Substances 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- 206010027525 Microalbuminuria Diseases 0.000 claims 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- UJNRUYFASNGLPC-GGINGMSCSA-N [(2r,3r,4r,5s,6s)-3,4,5-triacetyloxy-6-[4-chloro-3-[(2-cyano-3,4-dihydro-2h-1,4-benzoxazin-6-yl)methyl]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)O[C@H]1C1=CC=C(Cl)C(CC=2C=C3NCC(OC3=CC=2)C#N)=C1 UJNRUYFASNGLPC-GGINGMSCSA-N 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 239000003245 coal Substances 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 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 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 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 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 1
- 239000008103 glucose Substances 0.000 claims 1
- 201000001421 hyperglycemia Diseases 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 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 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 claims 1
- 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN2173/DEL/2009 | 2009-10-20 | ||
| IN2173DE2009 | 2009-10-20 | ||
| IN2689DE2009 | 2009-12-23 | ||
| IN2689/DEL/2009 | 2009-12-23 | ||
| PCT/EP2010/065747 WO2011048112A1 (en) | 2009-10-20 | 2010-10-19 | Glycoside derivatives and uses thereof |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013207478A Division JP2014040451A (ja) | 2009-10-20 | 2013-10-02 | グリコシド誘導体およびその使用 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013508335A JP2013508335A (ja) | 2013-03-07 |
| JP2013508335A5 true JP2013508335A5 (enExample) | 2013-07-18 |
| JP5384744B2 JP5384744B2 (ja) | 2014-01-08 |
Family
ID=43216622
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012534672A Expired - Fee Related JP5384744B2 (ja) | 2009-10-20 | 2010-10-19 | グリコシド誘導体およびその使用 |
| JP2013207478A Pending JP2014040451A (ja) | 2009-10-20 | 2013-10-02 | グリコシド誘導体およびその使用 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013207478A Pending JP2014040451A (ja) | 2009-10-20 | 2013-10-02 | グリコシド誘導体およびその使用 |
Country Status (39)
Families Citing this family (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BRPI1013559A2 (pt) | 2009-03-23 | 2016-04-12 | Glenmark Pharmaceuticals Sa | compostos, composição farmacêutica, método de tratamento de doença ou condição associada à função trpa1 e respectivos usos |
| US20110009347A1 (en) | 2009-07-08 | 2011-01-13 | Yin Liang | Combination therapy for the treatment of diabetes |
| US8163704B2 (en) * | 2009-10-20 | 2012-04-24 | Novartis Ag | Glycoside derivatives and uses thereof |
| CN102134226B (zh) * | 2010-01-26 | 2013-06-12 | 天津药物研究院 | 一类苯基c-葡萄糖苷衍生物、其制备方法和用途 |
| ES2596291T3 (es) | 2010-05-11 | 2017-01-05 | Janssen Pharmaceutica, N.V. | Formulaciones farmacéuticas que comprenden derivados de 1-(beta-d-glucopiranosil)-2-tienilmetilbenceno como inhibidores de sglt |
| CN103596944B (zh) | 2011-04-13 | 2017-02-22 | 詹森药业有限公司 | 可用作sglt2的抑制剂的化合物的制备方法 |
| US8614195B2 (en) * | 2011-04-14 | 2013-12-24 | Novartis Ag | Glycoside derivatives and uses thereof |
| CA2832951A1 (en) | 2011-04-14 | 2012-10-18 | Novartis Ag | Glycoside derivatives and uses thereof |
| US9035044B2 (en) * | 2011-05-09 | 2015-05-19 | Janssen Pharmaceutica Nv | L-proline and citric acid co-crystals of (2S, 3R, 4R, 5S,6R)-2-(3-((5-(4-fluorophenyl)thiopen-2-yl)methyl)4-methylphenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol |
| US9034921B2 (en) | 2011-06-01 | 2015-05-19 | Green Cross Corporation | Diphenylmethane derivatives as SGLT2 inhibitors |
| CN102827122B (zh) * | 2011-06-17 | 2015-01-14 | 山东轩竹医药科技有限公司 | 糖苷衍生物 |
| CN102863417B (zh) * | 2011-07-09 | 2015-01-14 | 山东轩竹医药科技有限公司 | C-糖苷衍生物 |
| TWI589576B (zh) | 2011-07-15 | 2017-07-01 | 諾華公司 | 氮雜－雙環二芳基醚之鹽類及製造彼等或其前驅物之方法 |
| AR087701A1 (es) * | 2011-08-31 | 2014-04-09 | Japan Tobacco Inc | Derivados de pirazol con actividad inhibidora de sglt1 |
| UA113086C2 (xx) | 2012-05-10 | 2016-12-12 | Піразольні сполуки як інгібітори sglt1 | |
| WO2014164286A1 (en) * | 2013-03-11 | 2014-10-09 | Janssen Pharmaceutica Nv | Dual sglt1/sglt2 inhibitors |
| EP3010586A1 (en) | 2013-06-21 | 2016-04-27 | Lupin Limited | Substituted heterocyclic compounds as crac modulators |
| EP3013810A1 (en) | 2013-06-24 | 2016-05-04 | Lupin Limited | Chromane and chromene derivatives and their use as crac modulators |
| CN104250272B (zh) * | 2013-06-27 | 2018-10-09 | 上海方楠生物科技有限公司 | 一种利用微反应器制备列净类药物中间体的方法 |
| CN107311992B (zh) * | 2013-09-09 | 2020-08-18 | 上海研健新药研发有限公司 | C-芳基葡糖苷衍生物、其制备方法及其在医药上的应用 |
| AR098670A1 (es) | 2013-11-08 | 2016-06-08 | Lilly Co Eli | Inhibidor de sglt1 |
| CN104017031A (zh) * | 2014-06-21 | 2014-09-03 | 李友香 | 降血糖药物和组合物 |
| CN104031098A (zh) * | 2014-06-21 | 2014-09-10 | 李友香 | 降糖药物 |
| CN105294624B (zh) * | 2015-11-16 | 2018-01-12 | 山东罗欣药业集团股份有限公司 | 一种达格列净的制备方法 |
| TN2018000437A1 (en) | 2016-06-17 | 2020-06-15 | Dae Woong Pharma | Method for producing diphenylmethane derivative |
| WO2018089449A1 (en) * | 2016-11-10 | 2018-05-17 | Janssen Pharmaceutica Nv | Benzocyclobutane derivatives useful as dual sglt1/sglt2 modulators |
| CN108203432B (zh) * | 2016-12-20 | 2021-03-02 | 宜昌东阳光长江药业股份有限公司 | 吡喃葡萄糖基衍生物及其在医药上的应用 |
| AR111161A1 (es) | 2017-03-03 | 2019-06-12 | Novartis Ag | Régimen de dosificación para el inhibidor sglt1/2 (licogliflozin) |
| WO2018189671A1 (en) * | 2017-04-12 | 2018-10-18 | Novartis Ag | Use of lik066 in heart failure patients |
| AU2018287810B2 (en) * | 2017-06-21 | 2021-03-25 | Novartis Ag | Licofligozin for the treatment of non-alcoholic steatohepatitis |
| US10696662B2 (en) | 2017-08-21 | 2020-06-30 | Janssen Pharmaceutica Nv | 5-fluoro-C-(aryl or heterocyclyl)-glycoside derivatives useful as dual SGLT1 / SGLT2 modulators |
| GB201721957D0 (en) | 2017-12-27 | 2018-02-07 | Bp Oil Int | Methods for preparing fuel additives |
| GB201721960D0 (en) | 2017-12-27 | 2018-02-07 | Bp Oil Int | Methods for preparing fuel additives |
| GB201721961D0 (en) | 2017-12-27 | 2018-02-07 | Bp Oil Int | Methods for preparing fuel additives |
| GB201721967D0 (en) | 2017-12-27 | 2018-02-07 | Bp Oil Int | Methods for preparing fuel additives |
| GB201721964D0 (en) | 2017-12-27 | 2018-02-07 | Bp Oil Int | Methods for preparing fuel additives |
| CN112424207B (zh) | 2018-07-25 | 2024-03-19 | 诺华股份有限公司 | Nlrp3炎性小体抑制剂 |
| CN108863736A (zh) * | 2018-07-27 | 2018-11-23 | 福州大学 | 一种羰基功能化的芳香羧酸的制备方法 |
| WO2020039394A1 (en) | 2018-08-24 | 2020-02-27 | Novartis Ag | New drug combinations |
| WO2020151620A1 (zh) * | 2019-01-24 | 2020-07-30 | 北京盈科瑞创新药物研究有限公司 | 化合物、其制备方法及其作为药物中间体的应用 |
| WO2020151623A1 (zh) * | 2019-01-24 | 2020-07-30 | 北京盈科瑞创新药物研究有限公司 | 化合物、其制备方法及其作为药物中间体的应用 |
| UY38687A (es) | 2019-05-17 | 2023-05-15 | Novartis Ag | Inhibidores del inflamasoma nlrp3, composiciones, combinaciones de los mismos y métodos para su uso |
| CA3142905A1 (en) | 2019-07-23 | 2021-01-28 | Novartis Ag | Combination treatment of liver diseases using fxr agonists |
| CN111099975A (zh) * | 2019-12-23 | 2020-05-05 | 河北合佳医药科技集团股份有限公司 | 一种5-溴-2-氯-4’-乙氧基二苯甲酮的制备方法 |
| JP7833464B2 (ja) * | 2020-11-19 | 2026-03-19 | ベイジン・インクリーズ・イノベーティブ・ドラッグ・カンパニー，リミテッド | グリコシド系誘導体及びその製造方法と応用 |
| KR20220080880A (ko) * | 2020-12-08 | 2022-06-15 | 주식회사 종근당 | 엠파글리플로진 공결정을 함유하는 약제학적 조성물 |
| UY40374A (es) | 2022-08-03 | 2024-02-15 | Novartis Ag | Inhibidores de inflamasoma nlrp3 |
Family Cites Families (64)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1020944C (zh) | 1990-01-30 | 1993-05-26 | 阿图尔-费希尔股份公司费希尔厂 | 紧固件 |
| US5410031A (en) | 1992-02-24 | 1995-04-25 | The Regents Of The University Of California Office Of Technology Transfer | Nucleoside cotransporter protein cDNA |
| US5410054A (en) | 1993-07-20 | 1995-04-25 | Merck Frosst Canada, Inc. | Heteroaryl quinolines as inhibitors of leukotriene biosynthesis |
| AU6024998A (en) | 1997-01-15 | 1998-08-07 | Glycomed Incorporated | Aryl c-glycoside compounds and sulfated esters thereof |
| BRPI0013667B8 (pt) | 1999-08-31 | 2021-05-25 | Kissei Pharmaceutical | derivados de glucopiranosiloxipirazol, composições medicinais contendo os mesmos e seus intermediários na produção deles |
| US6515117B2 (en) * | 1999-10-12 | 2003-02-04 | Bristol-Myers Squibb Company | C-aryl glucoside SGLT2 inhibitors and method |
| PH12000002657B1 (en) | 1999-10-12 | 2006-02-21 | Bristol Myers Squibb Co | C-aryl glucoside SGLT2 inhibitors |
| JP4272319B2 (ja) * | 1999-11-30 | 2009-06-03 | アイシン精機株式会社 | ヘッドレスト装置 |
| JP4456768B2 (ja) | 2000-02-02 | 2010-04-28 | 壽製薬株式会社 | Ｃ−配糖体を含有する薬剤 |
| US6627611B2 (en) * | 2000-02-02 | 2003-09-30 | Kotobuki Pharmaceutical Co Ltd | C-glycosides and preparation of thereof as antidiabetic agents |
| CZ20023023A3 (cs) | 2000-03-17 | 2003-04-16 | Kissei Pharmaceutical Co., Ltd. | Glukopyranosyloxybenzylbenzenové deriváty, léčivé směsi obsahující tyto látky a meziprodukty pro přípravu derivátů |
| US6683056B2 (en) | 2000-03-30 | 2004-01-27 | Bristol-Myers Squibb Company | O-aryl glucoside SGLT2 inhibitors and method |
| EP1329456B1 (en) | 2000-09-29 | 2006-08-09 | Kissei Pharmaceutical Co., Ltd. | Glucopyranosyloxybenzylbenzene derivatives and medicinal compositions containing the same |
| US6936590B2 (en) | 2001-03-13 | 2005-08-30 | Bristol Myers Squibb Company | C-aryl glucoside SGLT2 inhibitors and method |
| US20030045553A1 (en) | 2001-04-04 | 2003-03-06 | Bussolari Jacqueline C. | Combination therapy comprising glucose reabsorption inhibitors and PPAR modulators |
| WO2002080935A1 (en) | 2001-04-04 | 2002-10-17 | Ortho Mcneil Pharmaceutical, Inc. | Combination therapy comprising glucose reabsorption inhibitors and retinoid-x receptor modulators |
| US20030087843A1 (en) | 2001-09-05 | 2003-05-08 | Washburn William N. | O-pyrazole glucoside SGLT2 inhibitors and method of use |
| DE10231370B4 (de) | 2002-07-11 | 2006-04-06 | Sanofi-Aventis Deutschland Gmbh | Thiophenglycosidderivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zur Herstellung dieser Arzneimittel |
| JP2004137245A (ja) | 2002-08-23 | 2004-05-13 | Kissei Pharmaceut Co Ltd | ピラゾール誘導体、それを含有する医薬組成物、その医薬用途及びその製造中間体 |
| EP1568380A4 (en) | 2002-12-04 | 2009-10-21 | Kissei Pharmaceutical | PREVENTION OR TREATMENT OF DISEASES DUE TO HYPERGLYCEMIA |
| DE10258008B4 (de) | 2002-12-12 | 2006-02-02 | Sanofi-Aventis Deutschland Gmbh | Heterocyclische Fluorglycosidderivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zur Herstellung dieser Arzneimittel |
| DE10258007B4 (de) | 2002-12-12 | 2006-02-09 | Sanofi-Aventis Deutschland Gmbh | Aromatische Fluorglycosidderivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zur Herstellung dieser Arzneimittel |
| EP1444890B1 (en) | 2003-02-05 | 2009-01-07 | Hermann Koepsell | RS1 deficient transgenic animal and uses thereof |
| PL1609785T3 (pl) * | 2003-03-14 | 2016-07-29 | Astellas Pharma Inc | Pochodne c-glikozydowe i ich sole |
| AU2003902263A0 (en) | 2003-05-12 | 2003-05-29 | Fujisawa Pharmaceutical Co., Ltd. | Monosaccharide compounds |
| RS20060320A (sr) | 2003-08-01 | 2008-08-07 | Janssen Pharmaceutica N.V., | Supstituisani indazol-o-glukozidi |
| WO2005012326A1 (en) | 2003-08-01 | 2005-02-10 | Tanabe Seiyaku Co., Ltd. | Novel compounds having inhibitory activity against sodium-dependant transporter |
| JP4520988B2 (ja) | 2003-08-26 | 2010-08-11 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | グルコピラノシルオキシ−ピラゾール、これらの化合物を含む医薬組成物、これらの使用及びこれらの調製方法 |
| CA2557269C (en) | 2004-03-04 | 2012-12-04 | Kissei Pharmaceutical Co., Ltd. | Fused heterocycle derivative, medicinal composition containing the same, and medicinal use thereof |
| NZ549219A (en) | 2004-03-04 | 2010-08-27 | Kissei Pharmaceutical | Fused heterocycle derivative, medicinal composition containing the same, and medicinal use thereof |
| DE102004028241B4 (de) | 2004-06-11 | 2007-09-13 | Sanofi-Aventis Deutschland Gmbh | Neue Fluorglykosidderivate von Pyrazolen, diese Verbindungen enthaltende Arzneimittel und Herstellung dieser Arzneimittel |
| US7393836B2 (en) | 2004-07-06 | 2008-07-01 | Boehringer Ingelheim International Gmbh | D-xylopyranosyl-substituted phenyl derivatives, medicaments containing such compounds, their use and process for their manufacture |
| DE102004034690A1 (de) | 2004-07-17 | 2006-02-02 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Methyliden-D-xylopyranosyl-und Oxo-D-xylopyranosyl-substituierte Phenyle, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstellung |
| WO2006010557A1 (de) | 2004-07-27 | 2006-02-02 | Boehringer Ingelheim International Gmbh | D-glucopyranosyl-phenyl-substituierte cyclen, diese verbindungen enthaltende arzneimittel, deren verwendung und verfahren zu ihrer herstellung |
| WO2006018150A1 (de) | 2004-08-11 | 2006-02-23 | Boehringer Ingelheim International Gmbh | D-xylopyranosyl-phenyl-substituierte cyclen, diese verbindungen enthaltende arzneimittel, deren verwendung und verfahren zu ihrer herstellung |
| CA2577632C (en) | 2004-09-22 | 2014-04-01 | Soraya Shirazi-Beechey | Intestinal epithelial glucose sensor |
| DE102004048388A1 (de) | 2004-10-01 | 2006-04-06 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | D-Pyranosyl-substituierte Phenyle, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstellung |
| EP1813611B1 (en) | 2004-11-18 | 2014-10-01 | Kissei Pharmaceutical Co., Ltd. | 1-substituted-3- beta-d-glycopyranosylated nitrogenous hetero- cyclic compounds and medicines containing the same |
| UA91546C2 (uk) | 2005-05-03 | 2010-08-10 | Бьорінгер Інгельхайм Інтернаціональ Гмбх | КРИСТАЛІЧНА ФОРМА 1-ХЛОР-4-(β-D-ГЛЮКОПІРАНОЗ-1-ИЛ)-2-[4-((S)-ТЕТРАГІДРОФУРАН-3-ІЛОКСИ)-БЕНЗИЛ]-БЕНЗОЛУ, СПОСІБ ЇЇ ОДЕРЖАННЯ ТА ЇЇ ЗАСТОСУВАННЯ ПРИ ПРИГОТУВАННІ ЛІКАРСЬКИХ ЗАСОБІВ |
| TWI370818B (en) * | 2006-04-05 | 2012-08-21 | Astellas Pharma Inc | Cocrystal of c-glycoside derivative and l-proline |
| US7803778B2 (en) | 2006-05-23 | 2010-09-28 | Theracos, Inc. | Glucose transport inhibitors and methods of use |
| US20080027014A1 (en) | 2006-07-28 | 2008-01-31 | Tanabe Seiyaku Co., Ltd. | Novel SGLT inhibitors |
| TW200817424A (en) | 2006-08-04 | 2008-04-16 | Daiichi Sankyo Co Ltd | Benzylphenyl glucopyranoside derivatives |
| WO2008115574A1 (en) | 2007-03-21 | 2008-09-25 | Reliant Pharmaceuticals, Inc. | Cb1 antagonist and a dyslipidemic agent and/or metabolic regulator, and methods of making and using same |
| TW200904454A (en) | 2007-03-22 | 2009-02-01 | Bristol Myers Squibb Co | Methods for treating obesity employing an SGLT2 inhibitor and compositions thereof |
| BRPI0810409A2 (pt) | 2007-04-18 | 2015-02-18 | Thethys Bioscience Inc | Biomarcadores relacionados ao diabetes e métodos de uso destes |
| WO2009026389A2 (en) | 2007-08-20 | 2009-02-26 | Mount Sinai School Of Medicine | Regulating glp-1 and sglt-1 in gastrointestinal cells |
| US7838499B2 (en) | 2007-08-23 | 2010-11-23 | Theracos, Inc. | Benzylbenzene derivatives and methods of use |
| CL2008003653A1 (es) | 2008-01-17 | 2010-03-05 | Mitsubishi Tanabe Pharma Corp | Uso de un inhibidor de sglt derivado de glucopiranosilo y un inhibidor de dppiv seleccionado para tratar la diabetes; y composicion farmaceutica. |
| EP2236137B1 (en) * | 2008-01-31 | 2015-06-24 | Astellas Pharma Inc. | Pharmaceutical composition for treatment of fatty liver diseases |
| JP5820269B2 (ja) | 2008-05-22 | 2015-11-24 | アストラゼネカ・アクチエボラーグＡｓｔｒａｚｅｎｅｃａ Ａｋｔｉｅｂｏｌａｇ | Ｓｇｌｔ２阻害剤を使用する高尿酸血症の治療方法およびｓｇｌｔ２阻害剤を含有する組成物 |
| US8603989B2 (en) | 2008-05-22 | 2013-12-10 | Bristol-Myers Squibb Company | Method for treating and preventing kidney stones employing an SGLT2 inhibitor and composition containing same |
| US8518895B2 (en) | 2008-05-22 | 2013-08-27 | Bristol-Myers Squibb Company | Method for treating hyponatremia employing an SGLT2 inhibitor and composition containing same |
| EA201100503A1 (ru) | 2008-09-19 | 2011-10-31 | Новартис Аг | Глюкозидные производные и их применения |
| WO2010031813A1 (en) | 2008-09-19 | 2010-03-25 | Novartis Ag | Glycoside derivatives and uses thereof |
| US9056850B2 (en) | 2008-10-17 | 2015-06-16 | Janssen Pharmaceutica N.V. | Process for the preparation of compounds useful as inhibitors of SGLT |
| WO2010045656A2 (en) | 2008-10-17 | 2010-04-22 | Nectid, Inc. | Novel sglt2 inhibitor dosage forms |
| WO2010048358A2 (en) | 2008-10-22 | 2010-04-29 | Auspex Pharmaceutical, Inc. | Ethoxyphenylmethyl inhibitors of sglt2 |
| WO2010074219A1 (ja) | 2008-12-26 | 2010-07-01 | アステラス製薬株式会社 | ベンゾチオフェン化合物 |
| US20120035105A1 (en) | 2009-01-09 | 2012-02-09 | Sdg, Inc. | Insulin Therapies for the Treatment of Diabetes, Diabetes Related Ailments, and/or Diseases or Conditions Other Than Diabetes or Diabetes Related Ailments |
| EP4684831A3 (en) | 2009-02-13 | 2026-03-11 | Boehringer Ingelheim International GmbH | Sglt2 inhibitor for improving glycemic control |
| HUE050287T2 (hu) | 2009-02-13 | 2020-11-30 | Boehringer Ingelheim Int | SGLT2-inhibitort, DPP-IV-inhibitort és adott esetben egy további antidiabetikus hatóanyagot tartalmazó gyógyászati készítmény és alkalmazásai |
| WO2010128152A1 (en) * | 2009-05-07 | 2010-11-11 | Novartis Ag | Fused heterocyclic c-glycosides for the treatment of diabetes |
| US8163704B2 (en) | 2009-10-20 | 2012-04-24 | Novartis Ag | Glycoside derivatives and uses thereof |
-
2010
- 2010-10-18 US US12/906,682 patent/US8163704B2/en active Active
- 2010-10-19 BR BR112012009053-4A patent/BR112012009053B1/pt not_active IP Right Cessation
- 2010-10-19 KR KR1020127012873A patent/KR101465308B1/ko not_active Expired - Fee Related
- 2010-10-19 CU CU2012000062A patent/CU24079B1/es active IP Right Grant
- 2010-10-19 JP JP2012534672A patent/JP5384744B2/ja not_active Expired - Fee Related
- 2010-10-19 TW TW105117771A patent/TWI594756B/zh not_active IP Right Cessation
- 2010-10-19 TW TW099135639A patent/TWI558723B/zh not_active IP Right Cessation
- 2010-10-19 CA CA2777812A patent/CA2777812C/en active Active
- 2010-10-19 HR HRP20160436TT patent/HRP20160436T1/hr unknown
- 2010-10-19 DK DK10768927.5T patent/DK2491029T3/en active
- 2010-10-19 RS RS20160112A patent/RS54563B1/sr unknown
- 2010-10-19 PL PL10768927T patent/PL2491029T3/pl unknown
- 2010-10-19 MX MX2012004700A patent/MX2012004700A/es active IP Right Grant
- 2010-10-19 SG SG2012016820A patent/SG179562A1/en unknown
- 2010-10-19 EA EA201200600A patent/EA023781B1/ru not_active IP Right Cessation
- 2010-10-19 PE PE2012000511A patent/PE20121281A1/es active IP Right Grant
- 2010-10-19 NZ NZ598717A patent/NZ598717A/en not_active IP Right Cessation
- 2010-10-19 ES ES10768927.5T patent/ES2564191T3/es active Active
- 2010-10-19 KR KR1020147008569A patent/KR20140054415A/ko not_active Withdrawn
- 2010-10-19 PH PH1/2012/500518A patent/PH12012500518A1/en unknown
- 2010-10-19 MY MYPI2012001056A patent/MY158326A/en unknown
- 2010-10-19 HU HUE10768927A patent/HUE027531T2/en unknown
- 2010-10-19 WO PCT/EP2010/065747 patent/WO2011048112A1/en not_active Ceased
- 2010-10-19 EP EP10768927.5A patent/EP2491029B1/en active Active
- 2010-10-19 CN CN201080044483.5A patent/CN102656165B/zh not_active Expired - Fee Related
- 2010-10-19 AU AU2010309833A patent/AU2010309833B2/en not_active Ceased
- 2010-10-19 SI SI201031162A patent/SI2491029T1/sl unknown
- 2010-10-20 UY UY0001032958A patent/UY32958A/es active IP Right Grant
- 2010-10-20 AR ARP100103826A patent/AR078685A1/es active IP Right Grant
- 2010-10-20 JO JOP/2010/0359A patent/JO3152B1/ar active
-
2012
- 2012-03-07 ZA ZA2012/01680A patent/ZA201201680B/en unknown
- 2012-03-09 TN TNP2012000109A patent/TN2012000109A1/en unknown
- 2012-03-21 US US13/425,888 patent/US8466114B2/en active Active
- 2012-04-12 CR CR20120176A patent/CR20120176A/es unknown
- 2012-04-19 HN HN2012000798A patent/HN2012000798A/es unknown
- 2012-04-19 CL CL2012000991A patent/CL2012000991A1/es unknown
- 2012-04-19 IL IL219309A patent/IL219309A/en active IP Right Grant
- 2012-04-20 GT GT201200117A patent/GT201200117A/es unknown
- 2012-04-26 CO CO12068967A patent/CO6531486A2/es active IP Right Grant
- 2012-05-11 MA MA34854A patent/MA33737B1/fr unknown
- 2012-05-17 EC ECSP12011909 patent/ECSP12011909A/es unknown
- 2012-09-13 US US13/614,534 patent/US8828951B2/en active Active
-
2013
- 2013-10-02 JP JP2013207478A patent/JP2014040451A/ja active Pending
-
2014
- 2014-05-30 US US14/291,268 patent/US20140274921A1/en not_active Abandoned
-
2015
- 2015-01-23 US US14/604,173 patent/US20150141354A1/en not_active Abandoned
-
2016
- 2016-04-19 CY CY20161100330T patent/CY1117409T1/el unknown
- 2016-04-20 US US15/134,016 patent/US9895389B2/en not_active Ceased
-
2020
- 2020-02-18 US US16/793,734 patent/USRE49080E1/en active Active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2013508335A5 (enExample) | ||
| CA2777812A1 (en) | Glycoside derivatives and uses thereof | |
| KR101686308B1 (ko) | 융합된 비시클릭 옥사졸리디논 cetp 억제제 | |
| US9751881B2 (en) | Inhibitors of the renal outer medullary potassium channel | |
| KR102284938B1 (ko) | 다이하이드로피리미딘 유도체 및 이의 중간산물의 제조 방법 | |
| US7528160B2 (en) | Fused heterocyclic derivatives as PPAR modulators | |
| JP6500010B2 (ja) | 新規ピリジン誘導体 | |
| JP2013544873A5 (enExample) | ||
| JP2010536882A5 (enExample) | ||
| HRP20030522A2 (en) | Heterocyclic compounds having antibacterial activity, process for their preparatoin and pharmaceutical compositions containing them | |
| BRPI0707491B1 (pt) | compostos úteis como agentes moduladores de receptores de mineralocorticóides, os referidos agentes compreendendo os mesmos e composições farmacêuticas | |
| JP2003518117A (ja) | スルホキシミン官能基を有するオキサゾリジノンおよび抗微生物剤としてのその使用 | |
| JP2017521399A (ja) | 腎髄質外層カリウムチャンネルの阻害剤 | |
| RU2011118497A (ru) | Оксазолидиниловые антибиотики | |
| US6642238B2 (en) | Oxazolidinone thioamides with piperazine amide substituents | |
| EP3083587B1 (en) | Oximino derivatives for the treatment of dyslipidemia | |
| KR20210038632A (ko) | 포유류 감염 치료를 위한 신규 화합물 | |
| CA2058254A1 (en) | Benzodioxole derivatives | |
| US8389508B2 (en) | Heterocyclic compounds | |
| WO2011134280A1 (en) | Compounds as agonists of s1p1 receptors | |
| JP2016504375A (ja) | 新規なベンゾジオキサン−ピペリジン誘導体および神経精神障害を治療するためのそれらの治療適用 | |
| RU2798336C2 (ru) | Новые соединения для лечения инфекций млекопитающих | |
| WO2024249252A1 (en) | Methods of using apol1 inhibitors | |
| HK40043248A (en) | Substituted oxazolidinones for the treatment of mammalian infections | |
| JP2000327663A (ja) | ２，３−ジヒドロ−１，４−ベンゾオキサジン化合物 |