JP2009535378A5 - - Google Patents
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- Publication number
- JP2009535378A5 JP2009535378A5 JP2009508336A JP2009508336A JP2009535378A5 JP 2009535378 A5 JP2009535378 A5 JP 2009535378A5 JP 2009508336 A JP2009508336 A JP 2009508336A JP 2009508336 A JP2009508336 A JP 2009508336A JP 2009535378 A5 JP2009535378 A5 JP 2009535378A5
- Authority
- JP
- Japan
- Prior art keywords
- benzonitrile
- benzyl
- glucopyranos
- group
- alkyl
- 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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- -1 1-hydroxy-cyclopropyl Chemical group 0.000 claims 15
- 150000003839 salts Chemical class 0.000 claims 15
- 150000001875 compounds Chemical class 0.000 claims 13
- 239000008194 pharmaceutical composition Substances 0.000 claims 13
- 239000013543 active substance Substances 0.000 claims 7
- 125000003118 aryl group Chemical group 0.000 claims 7
- 239000003085 diluting agent Substances 0.000 claims 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 5
- 239000000969 carrier Substances 0.000 claims 5
- 239000003112 inhibitor Substances 0.000 claims 5
- 238000002360 preparation method Methods 0.000 claims 5
- 150000008359 benzonitriles Chemical class 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims 3
- 230000002265 prevention Effects 0.000 claims 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
- FZSFTEGBVMGDPN-XNBWIAOKSA-N 2-[(4-propylphenyl)methyl]-4-[(2R,3R,4S,5S,6R)-2,3,4,5-tetrahydroxy-6-(hydroxymethyl)oxan-2-yl]benzonitrile Chemical compound CCCc1ccc(Cc2cc(ccc2C#N)[C@@]2(O)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)cc1 FZSFTEGBVMGDPN-XNBWIAOKSA-N 0.000 claims 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 2
- 201000001320 Atherosclerosis Diseases 0.000 claims 2
- 210000002237 B-cell of pancreatic islet Anatomy 0.000 claims 2
- 206010007556 Cardiac failure acute Diseases 0.000 claims 2
- 239000005977 Ethylene Substances 0.000 claims 2
- DTHNMHAUYICORS-KTKZVXAJSA-N Glucagon-like peptide 1 Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(N)=O)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC=1N=CNC=1)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=CC=C1 DTHNMHAUYICORS-KTKZVXAJSA-N 0.000 claims 2
- 206010020772 Hypertension Diseases 0.000 claims 2
- 208000008589 Obesity Diseases 0.000 claims 2
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 claims 2
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 claims 2
- 125000004036 acetal group Chemical group 0.000 claims 2
- 239000005557 antagonist Substances 0.000 claims 2
- 125000005129 aryl carbonyl group Chemical group 0.000 claims 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 239000003925 fat Substances 0.000 claims 2
- 238000009472 formulation Methods 0.000 claims 2
- 150000002367 halogens Chemical group 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 210000004185 liver Anatomy 0.000 claims 2
- 208000030159 metabolic disease Diseases 0.000 claims 2
- 235000020824 obesity Nutrition 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- RMMXLENWKUUMAY-UHFFFAOYSA-N telmisartan Chemical compound CCCC1=NC2=C(C)C=C(C=3N(C4=CC=CC=C4N=3)C)C=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C(O)=O RMMXLENWKUUMAY-UHFFFAOYSA-N 0.000 claims 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 2
- 229940116269 uric acid Drugs 0.000 claims 2
- HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 claims 1
- ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 claims 1
- 101710175516 14 kDa zinc-binding protein Proteins 0.000 claims 1
- YWTAGPKLVGWYRA-OUUBHVDSSA-N 2-[(4-bromophenyl)methyl]-4-[(2R,3R,4S,5S,6R)-2,3,4,5-tetrahydroxy-6-(hydroxymethyl)oxan-2-yl]benzonitrile Chemical compound OC[C@H]1O[C@@](O)([C@H](O)[C@@H](O)[C@@H]1O)c1ccc(C#N)c(Cc2ccc(Br)cc2)c1 YWTAGPKLVGWYRA-OUUBHVDSSA-N 0.000 claims 1
- VUXOCCIUXRLWEO-OUUBHVDSSA-N 2-[(4-chlorophenyl)methyl]-4-[(2R,3R,4S,5S,6R)-2,3,4,5-tetrahydroxy-6-(hydroxymethyl)oxan-2-yl]benzonitrile Chemical compound ClC1=CC=C(CC2=C(C#N)C=CC(=C2)[C@]2(O)[C@H](O)[C@@H](O)[C@H](O)[C@H](O2)CO)C=C1 VUXOCCIUXRLWEO-OUUBHVDSSA-N 0.000 claims 1
- UIKYJAIFPMVNPX-YMQHIKHWSA-N 2-[(4-cyanophenyl)methyl]-4-[(2R,3R,4S,5S,6R)-2,3,4,5-tetrahydroxy-6-(hydroxymethyl)oxan-2-yl]benzonitrile Chemical compound C(#N)C1=CC=C(CC2=C(C#N)C=CC(=C2)[C@]2(O)[C@H](O)[C@@H](O)[C@H](O)[C@H](O2)CO)C=C1 UIKYJAIFPMVNPX-YMQHIKHWSA-N 0.000 claims 1
- NQPYBJPDHKCNLR-GNADVCDUSA-N 2-[(4-cyclobutylphenyl)methyl]-4-[(2R,3R,4S,5S,6R)-2,3,4,5-tetrahydroxy-6-(hydroxymethyl)oxan-2-yl]benzonitrile Chemical compound OC[C@H]1O[C@@](O)([C@H](O)[C@@H](O)[C@@H]1O)c1ccc(C#N)c(Cc2ccc(cc2)C2CCC2)c1 NQPYBJPDHKCNLR-GNADVCDUSA-N 0.000 claims 1
- PESZPPAQWQMZAM-XNBWIAOKSA-N 2-[(4-cyclopropylphenyl)methyl]-4-[(2r,3r,4s,5s,6r)-2,3,4,5-tetrahydroxy-6-(hydroxymethyl)oxan-2-yl]benzonitrile Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@]1(O)C1=CC=C(C#N)C(CC=2C=CC(=CC=2)C2CC2)=C1 PESZPPAQWQMZAM-XNBWIAOKSA-N 0.000 claims 1
- ONUREMLYTYVMSI-QMCAAQAGSA-N 2-[(4-ethylphenyl)methyl]-4-[(2R,3R,4S,5S,6R)-2,3,4,5-tetrahydroxy-6-(hydroxymethyl)oxan-2-yl]benzonitrile Chemical compound CCc1ccc(Cc2cc(ccc2C#N)[C@@]2(O)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)cc1 ONUREMLYTYVMSI-QMCAAQAGSA-N 0.000 claims 1
- MMEAQBZZICUZSQ-OUUBHVDSSA-N 2-[(4-fluorophenyl)methyl]-4-[(2R,3R,4S,5S,6R)-2,3,4,5-tetrahydroxy-6-(hydroxymethyl)oxan-2-yl]benzonitrile Chemical compound FC1=CC=C(CC2=C(C#N)C=CC(=C2)[C@]2(O)[C@H](O)[C@@H](O)[C@H](O)[C@H](O2)CO)C=C1 MMEAQBZZICUZSQ-OUUBHVDSSA-N 0.000 claims 1
- PZUDLXSTHUCFBN-OUUBHVDSSA-N 2-[(4-hydroxyphenyl)methyl]-4-[(2r,3r,4s,5s,6r)-2,3,4,5-tetrahydroxy-6-(hydroxymethyl)oxan-2-yl]benzonitrile Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@]1(O)C1=CC=C(C#N)C(CC=2C=CC(O)=CC=2)=C1 PZUDLXSTHUCFBN-OUUBHVDSSA-N 0.000 claims 1
- STUHXPQBQNKENW-OUUBHVDSSA-N 2-[(4-iodophenyl)methyl]-4-[(2r,3r,4s,5s,6r)-2,3,4,5-tetrahydroxy-6-(hydroxymethyl)oxan-2-yl]benzonitrile Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@]1(O)C1=CC=C(C#N)C(CC=2C=CC(I)=CC=2)=C1 STUHXPQBQNKENW-OUUBHVDSSA-N 0.000 claims 1
- LAFRQCUAGNTVNI-YMQHIKHWSA-N 2-[(4-methylphenyl)methyl]-4-[(2R,3R,4S,5S,6R)-2,3,4,5-tetrahydroxy-6-(hydroxymethyl)oxan-2-yl]benzonitrile Chemical compound Cc1ccc(Cc2cc(ccc2C#N)[C@@]2(O)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)cc1 LAFRQCUAGNTVNI-YMQHIKHWSA-N 0.000 claims 1
- VDSXGGJBIBYTFY-YMQHIKHWSA-N 2-[(4-methylsulfanylphenyl)methyl]-4-[(2r,3r,4s,5s,6r)-2,3,4,5-tetrahydroxy-6-(hydroxymethyl)oxan-2-yl]benzonitrile Chemical compound C1=CC(SC)=CC=C1CC1=CC([C@]2(O)[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)=CC=C1C#N VDSXGGJBIBYTFY-YMQHIKHWSA-N 0.000 claims 1
- IAVPOKMOINUNHO-AVBUBTBZSA-N 2-[(4-methylsulfinylphenyl)methyl]-4-[(2r,3r,4s,5s,6r)-2,3,4,5-tetrahydroxy-6-(hydroxymethyl)oxan-2-yl]benzonitrile Chemical compound C1=CC(S(=O)C)=CC=C1CC1=CC([C@]2(O)[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)=CC=C1C#N IAVPOKMOINUNHO-AVBUBTBZSA-N 0.000 claims 1
- VLXOYODPXLFUMT-YMQHIKHWSA-N 2-[(4-methylsulfonylphenyl)methyl]-4-[(2R,3R,4S,5S,6R)-2,3,4,5-tetrahydroxy-6-(hydroxymethyl)oxan-2-yl]benzonitrile Chemical compound O[C@]1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)C1=CC(=C(C#N)C=C1)CC1=CC=C(C=C1)S(=O)(=O)C VLXOYODPXLFUMT-YMQHIKHWSA-N 0.000 claims 1
- FPFHQONEECSLSA-XNBWIAOKSA-N 2-[(4-propan-2-ylphenyl)methyl]-4-[(2R,3R,4S,5S,6R)-2,3,4,5-tetrahydroxy-6-(hydroxymethyl)oxan-2-yl]benzonitrile Chemical compound CC(C)c1ccc(Cc2cc(ccc2C#N)[C@@]2(O)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)cc1 FPFHQONEECSLSA-XNBWIAOKSA-N 0.000 claims 1
- IDLWWORNYZYXGU-WKKMNAASSA-N 2-[(4-tert-butylphenyl)methyl]-4-[(2R,3R,4S,5S,6R)-2,3,4,5-tetrahydroxy-6-(hydroxymethyl)oxan-2-yl]benzonitrile Chemical compound O[C@]1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)C1=CC(=C(C#N)C=C1)CC1=CC=C(C=C1)C(C)(C)C IDLWWORNYZYXGU-WKKMNAASSA-N 0.000 claims 1
- SLPBHXGYJHBBAP-OUUBHVDSSA-N 2-[[4-(1,1,2,2,2-pentafluoroethyl)phenyl]methyl]-4-[(2r,3r,4s,5s,6r)-2,3,4,5-tetrahydroxy-6-(hydroxymethyl)oxan-2-yl]benzonitrile Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@]1(O)C1=CC=C(C#N)C(CC=2C=CC(=CC=2)C(F)(F)C(F)(F)F)=C1 SLPBHXGYJHBBAP-OUUBHVDSSA-N 0.000 claims 1
- UIFQEKUBCSTTGD-ZFVIQDPVSA-N 2-[[4-(1-hydroxycyclopropyl)phenyl]methyl]-4-[(2R,3R,4S,5S,6R)-2,3,4,5-tetrahydroxy-6-(hydroxymethyl)oxan-2-yl]benzonitrile Chemical compound O[C@]1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)C1=CC(=C(C#N)C=C1)CC1=CC=C(C=C1)C1(CC1)O UIFQEKUBCSTTGD-ZFVIQDPVSA-N 0.000 claims 1
- MVHQZLSXEHNLPX-XNBWIAOKSA-N 2-[[4-(2-methoxyethoxy)phenyl]methyl]-4-[(2R,3R,4S,5S,6R)-2,3,4,5-tetrahydroxy-6-(hydroxymethyl)oxan-2-yl]benzonitrile Chemical compound COCCOc1ccc(Cc2cc(ccc2C#N)[C@@]2(O)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)cc1 MVHQZLSXEHNLPX-XNBWIAOKSA-N 0.000 claims 1
- XJJOUHFFENFZSG-NHTNDUFYSA-N 2-[[4-(3-methylbutyl)phenyl]methyl]-4-[(2R,3R,4S,5S,6R)-2,3,4,5-tetrahydroxy-6-(hydroxymethyl)oxan-2-yl]benzonitrile Chemical compound CC(C)CCc1ccc(Cc2cc(ccc2C#N)[C@@]2(O)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)cc1 XJJOUHFFENFZSG-NHTNDUFYSA-N 0.000 claims 1
- MPFSBSMACSMPLK-GQUPQBGVSA-N 2-[[4-(difluoromethoxy)phenyl]methyl]-4-[(2R,3R,4S,5S,6R)-2,3,4,5-tetrahydroxy-6-(hydroxymethyl)oxan-2-yl]benzonitrile Chemical compound OC[C@H]1O[C@@](O)([C@H](O)[C@@H](O)[C@@H]1O)c1ccc(C#N)c(Cc2ccc(OC(F)F)cc2)c1 MPFSBSMACSMPLK-GQUPQBGVSA-N 0.000 claims 1
- OWPRWLBXMXEAEI-GQUPQBGVSA-N 2-[[4-(difluoromethyl)phenyl]methyl]-4-[(2R,3R,4S,5S,6R)-2,3,4,5-tetrahydroxy-6-(hydroxymethyl)oxan-2-yl]benzonitrile Chemical compound OC[C@H]1O[C@@](O)([C@H](O)[C@@H](O)[C@@H]1O)c1ccc(C#N)c(Cc2ccc(cc2)C(F)F)c1 OWPRWLBXMXEAEI-GQUPQBGVSA-N 0.000 claims 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims 1
- 239000003148 4 aminobutyric acid receptor blocking agent Substances 0.000 claims 1
- LLZCTNXNCKCGCH-OUUBHVDSSA-N 4-[(2R,3R,4S,5S,6R)-2,3,4,5-tetrahydroxy-6-(hydroxymethyl)oxan-2-yl]-2-[[4-(trifluoromethyl)phenyl]methyl]benzonitrile Chemical compound OC[C@H]1O[C@@](O)([C@H](O)[C@@H](O)[C@@H]1O)c1ccc(C#N)c(Cc2ccc(cc2)C(F)(F)F)c1 LLZCTNXNCKCGCH-OUUBHVDSSA-N 0.000 claims 1
- RGRLJNQPNXJYTB-XNBWIAOKSA-N 4-[(2r,3r,4s,5s,6r)-2,3,4,5-tetrahydroxy-6-(hydroxymethyl)oxan-2-yl]-2-[(4-trimethylsilylphenyl)methyl]benzonitrile Chemical compound C1=CC([Si](C)(C)C)=CC=C1CC1=CC([C@]2(O)[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)=CC=C1C#N RGRLJNQPNXJYTB-XNBWIAOKSA-N 0.000 claims 1
- IVGXPPTYGVYLON-OUUBHVDSSA-N 4-[(2r,3r,4s,5s,6r)-2,3,4,5-tetrahydroxy-6-(hydroxymethyl)oxan-2-yl]-2-[[4-(trifluoromethoxy)phenyl]methyl]benzonitrile Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@]1(O)C1=CC=C(C#N)C(CC=2C=CC(OC(F)(F)F)=CC=2)=C1 IVGXPPTYGVYLON-OUUBHVDSSA-N 0.000 claims 1
- IMVDZFOSXJSXFP-UHFFFAOYSA-N 5-chloro-2-propyl-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]phenyl]methyl]imidazole-4-carbaldehyde Chemical compound CCCC1=NC(Cl)=C(C=O)N1CC1=CC=C(C=2C(=CC=CC=2)C2=NNN=N2)C=C1 IMVDZFOSXJSXFP-UHFFFAOYSA-N 0.000 claims 1
- 208000010444 Acidosis Diseases 0.000 claims 1
- 101710152627 Aldose reductase A Proteins 0.000 claims 1
- 229940077274 Alpha glucosidase inhibitor Drugs 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 239000002083 C09CA01 - Losartan Substances 0.000 claims 1
- 239000004072 C09CA03 - Valsartan Substances 0.000 claims 1
- 239000002947 C09CA04 - Irbesartan Substances 0.000 claims 1
- 239000002081 C09CA05 - Tasosartan Substances 0.000 claims 1
- 239000005537 C09CA07 - Telmisartan Substances 0.000 claims 1
- GHOSNRCGJFBJIB-UHFFFAOYSA-N Candesartan cilexetil Chemical group C=12N(CC=3C=CC(=CC=3)C=3C(=CC=CC=3)C3=NNN=N3)C(OCC)=NC2=CC=CC=1C(=O)OC(C)OC(=O)OC1CCCCC1 GHOSNRCGJFBJIB-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 208000002249 Diabetes Complications Diseases 0.000 claims 1
- 206010012655 Diabetic complications Diseases 0.000 claims 1
- 102100025012 Dipeptidyl peptidase 4 Human genes 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 229940098788 GABA receptor antagonist Drugs 0.000 claims 1
- 102100025101 GATA-type zinc finger protein 1 Human genes 0.000 claims 1
- 101710198884 GATA-type zinc finger protein 1 Proteins 0.000 claims 1
- FAEKWTJYAYMJKF-QHCPKHFHSA-N GlucoNorm Chemical compound C1=C(C(O)=O)C(OCC)=CC(CC(=O)N[C@@H](CC(C)C)C=2C(=CC=CC=2)N2CCCCC2)=C1 FAEKWTJYAYMJKF-QHCPKHFHSA-N 0.000 claims 1
- 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 1
- 101000684208 Homo sapiens Prolyl endopeptidase FAP Proteins 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 206010060378 Hyperinsulinaemia Diseases 0.000 claims 1
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| PCT/EP2007/054248 WO2007128749A1 (en) | 2006-05-03 | 2007-05-02 | Glucopyranosyl-substituted benzonitrile derivatives, pharmaceutical compositions containing such compounds, their use and process for their manufacture |
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| US8980894B2 (en) | 2004-03-25 | 2015-03-17 | Boehringer Ingelheim Vetmedica Gmbh | Use of PDE III inhibitors for the treatment of asymptomatic (occult) heart failure |
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