JP2010523583A5 - - Google Patents
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- Publication number
- JP2010523583A5 JP2010523583A5 JP2010502246A JP2010502246A JP2010523583A5 JP 2010523583 A5 JP2010523583 A5 JP 2010523583A5 JP 2010502246 A JP2010502246 A JP 2010502246A JP 2010502246 A JP2010502246 A JP 2010502246A JP 2010523583 A5 JP2010523583 A5 JP 2010523583A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- cycloalkyl
- chloro
- pyran
- phenyl
- 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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- 125000000753 cycloalkyl group Chemical group 0.000 claims 50
- -1 chloro, hydroxy Chemical group 0.000 claims 43
- 150000001875 compounds Chemical class 0.000 claims 28
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 28
- 229910052760 oxygen Inorganic materials 0.000 claims 27
- 239000001301 oxygen Substances 0.000 claims 27
- 125000000217 alkyl group Chemical group 0.000 claims 26
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 26
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 24
- 229910052717 sulfur Inorganic materials 0.000 claims 24
- 239000011593 sulfur Substances 0.000 claims 24
- 229910052736 halogen Inorganic materials 0.000 claims 21
- 150000002367 halogens Chemical class 0.000 claims 21
- 229910052739 hydrogen Inorganic materials 0.000 claims 21
- 239000001257 hydrogen Substances 0.000 claims 21
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 19
- 150000002431 hydrogen Chemical class 0.000 claims 18
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 17
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 17
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 17
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 16
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 16
- 125000003342 alkenyl group Chemical group 0.000 claims 10
- 239000003814 drug Substances 0.000 claims 10
- 125000001424 substituent group Chemical group 0.000 claims 10
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims 9
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 8
- 125000000304 alkynyl group Chemical group 0.000 claims 8
- 125000001072 heteroaryl group Chemical group 0.000 claims 8
- 239000003112 inhibitor Substances 0.000 claims 7
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 6
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 125000005129 aryl carbonyl group Chemical group 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 6
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims 6
- 239000003795 chemical substances by application Substances 0.000 claims 6
- 125000002993 cycloalkylene group Chemical group 0.000 claims 6
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 6
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims 5
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 5
- 125000004104 aryloxy group Chemical group 0.000 claims 5
- 229940079593 drug Drugs 0.000 claims 5
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims 5
- 229940124597 therapeutic agent Drugs 0.000 claims 5
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 4
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 4
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims 4
- 125000004465 cycloalkenyloxy group Chemical group 0.000 claims 4
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 4
- 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 4
- 229940044601 receptor agonist Drugs 0.000 claims 4
- 239000000018 receptor agonist Substances 0.000 claims 4
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 3
- XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 claims 3
- 229940123208 Biguanide Drugs 0.000 claims 3
- 125000005336 allyloxy group Chemical group 0.000 claims 3
- 239000000883 anti-obesity agent Substances 0.000 claims 3
- 229940125710 antiobesity agent Drugs 0.000 claims 3
- 125000005100 aryl amino carbonyl group Chemical group 0.000 claims 3
- 125000005724 cycloalkenylene group Chemical group 0.000 claims 3
- 125000006576 di-(C1-C3-alkyl)-aminocarbonyl group Chemical group 0.000 claims 3
- 229910052731 fluorine Inorganic materials 0.000 claims 3
- 239000011737 fluorine Substances 0.000 claims 3
- 125000001153 fluoro group Chemical group F* 0.000 claims 3
- 125000005222 heteroarylaminocarbonyl group Chemical group 0.000 claims 3
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 3
- 239000000126 substance Substances 0.000 claims 3
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 3
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims 2
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 2
- 125000004760 (C1-C4) alkylsulfonylamino group Chemical group 0.000 claims 2
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims 2
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 2
- ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 claims 2
- 201000001320 Atherosclerosis Diseases 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- 208000002249 Diabetes Complications Diseases 0.000 claims 2
- 206010012655 Diabetic complications Diseases 0.000 claims 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 2
- DTHNMHAUYICORS-KTKZVXAJSA-N Glucagon-like peptide 1 Chemical class 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 102000004877 Insulin Human genes 0.000 claims 2
- 108090001061 Insulin Proteins 0.000 claims 2
- 206010022489 Insulin Resistance Diseases 0.000 claims 2
- 108010041872 Islet Amyloid Polypeptide Chemical class 0.000 claims 2
- 102000036770 Islet Amyloid Polypeptide Human genes 0.000 claims 2
- 102100038831 Peroxisome proliferator-activated receptor alpha Human genes 0.000 claims 2
- YASAKCUCGLMORW-UHFFFAOYSA-N Rosiglitazone Chemical compound C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O YASAKCUCGLMORW-UHFFFAOYSA-N 0.000 claims 2
- 229940100389 Sulfonylurea Drugs 0.000 claims 2
- 229940123464 Thiazolidinedione Drugs 0.000 claims 2
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims 2
- 239000012190 activator Substances 0.000 claims 2
- 239000000048 adrenergic agonist Substances 0.000 claims 2
- 229940126157 adrenergic receptor agonist Drugs 0.000 claims 2
- 239000000556 agonist Substances 0.000 claims 2
- 125000004450 alkenylene group Chemical group 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 230000003178 anti-diabetic effect Effects 0.000 claims 2
- 229940125708 antidiabetic agent Drugs 0.000 claims 2
- 239000003472 antidiabetic agent Substances 0.000 claims 2
- 125000004658 aryl carbonyl amino group Chemical group 0.000 claims 2
- 125000005199 aryl carbonyloxy group Chemical group 0.000 claims 2
- 125000005163 aryl sulfanyl group Chemical group 0.000 claims 2
- 125000004657 aryl sulfonyl amino group Chemical group 0.000 claims 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 230000001684 chronic effect Effects 0.000 claims 2
- 125000005171 cycloalkylsulfanyl group Chemical group 0.000 claims 2
- 125000005144 cycloalkylsulfonyl group Chemical group 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 208000019622 heart disease Diseases 0.000 claims 2
- 125000005224 heteroarylcarbonylamino group Chemical group 0.000 claims 2
- 125000005150 heteroarylsulfinyl group Chemical group 0.000 claims 2
- 229940125396 insulin Drugs 0.000 claims 2
- NRYBAZVQPHGZNS-ZSOCWYAHSA-N leptin Chemical compound O=C([C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](N)CC(C)C)CCSC)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](CS)C(O)=O NRYBAZVQPHGZNS-ZSOCWYAHSA-N 0.000 claims 2
- 150000002632 lipids Chemical class 0.000 claims 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 2
- PKWDZWYVIHVNKS-UHFFFAOYSA-N netoglitazone Chemical compound FC1=CC=CC=C1COC1=CC=C(C=C(CC2C(NC(=O)S2)=O)C=C2)C2=C1 PKWDZWYVIHVNKS-UHFFFAOYSA-N 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 108091008725 peroxisome proliferator-activated receptors alpha Proteins 0.000 claims 2
- HYAFETHFCAUJAY-UHFFFAOYSA-N pioglitazone Chemical compound N1=CC(CC)=CC=C1CCOC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 HYAFETHFCAUJAY-UHFFFAOYSA-N 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 238000006467 substitution reaction Methods 0.000 claims 2
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 claims 2
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims 1
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 claims 1
- XUFXOAAUWZOOIT-SXARVLRPSA-N (2R,3R,4R,5S,6R)-5-[[(2R,3R,4R,5S,6R)-5-[[(2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-1-cyclohex-2-enyl]amino]-2-oxanyl]oxy]-3,4-dihydroxy-6-(hydroxymethyl)-2-oxanyl]oxy]-6-(hydroxymethyl)oxane-2,3,4-triol Chemical compound O([C@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O[C@H]1O[C@@H]([C@H]([C@H](O)[C@H]1O)N[C@@H]1[C@@H]([C@@H](O)[C@H](O)C(CO)=C1)O)C)[C@@H]1[C@@H](CO)O[C@@H](O)[C@H](O)[C@H]1O XUFXOAAUWZOOIT-SXARVLRPSA-N 0.000 claims 1
- ZXEIEKDGPVTZLD-NDEPHWFRSA-N (2s)-2-dodecylsulfanyl-n-(4-hydroxy-2,3,5-trimethylphenyl)-2-phenylacetamide Chemical compound O=C([C@@H](SCCCCCCCCCCCC)C=1C=CC=CC=1)NC1=CC(C)=C(O)C(C)=C1C ZXEIEKDGPVTZLD-NDEPHWFRSA-N 0.000 claims 1
- VMTQLXPABLZMOL-SEFGFODJSA-N (2s,3r,4r,5s,6r)-2-[2-(2-but-2-ynoxyethoxy)-4-chloro-5-[(4-ethylphenyl)methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C1=CC(CC)=CC=C1CC1=CC([C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)=C(OCCOCC#CC)C=C1Cl VMTQLXPABLZMOL-SEFGFODJSA-N 0.000 claims 1
- PPVMZZYRTYKVLS-RTJMFUJLSA-N (2s,3r,4r,5s,6r)-2-[2-(but-2-ynoxymethyl)-4-chloro-5-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C1=CC(OCC)=CC=C1CC1=CC([C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)=C(COCC#CC)C=C1Cl PPVMZZYRTYKVLS-RTJMFUJLSA-N 0.000 claims 1
- WIGXVRQAKNBIQK-RTJMFUJLSA-N (2s,3r,4r,5s,6r)-2-[2-(but-2-ynoxymethyl)-4-chloro-5-[(4-ethylphenyl)methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C1=CC(CC)=CC=C1CC1=CC([C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)=C(COCC#CC)C=C1Cl WIGXVRQAKNBIQK-RTJMFUJLSA-N 0.000 claims 1
- YJUVSHGSPXQZGE-SJSRKZJXSA-N (2s,3r,4r,5s,6r)-2-[2-(but-2-ynoxymethyl)-4-chloro-5-[(4-hydroxyphenyl)methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C1=C([C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)C(COCC#CC)=CC(Cl)=C1CC1=CC=C(O)C=C1 YJUVSHGSPXQZGE-SJSRKZJXSA-N 0.000 claims 1
- XPTKDTORPKCTNJ-RTJMFUJLSA-N (2s,3r,4r,5s,6r)-2-[2-(but-3-ynoxymethyl)-4-chloro-5-[(4-ethylphenyl)methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C1=CC(CC)=CC=C1CC1=CC([C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)=C(COCCC#C)C=C1Cl XPTKDTORPKCTNJ-RTJMFUJLSA-N 0.000 claims 1
- PUXBIQNREQEAEK-ZXGKGEBGSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-2-(2,2-difluoroethoxymethyl)-5-[(4-ethylphenyl)methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C1=CC(CC)=CC=C1CC1=CC([C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)=C(COCC(F)F)C=C1Cl PUXBIQNREQEAEK-ZXGKGEBGSA-N 0.000 claims 1
- DMZMZZPXFAVPED-HFBCXCLPSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-2-[2-(2,2-difluoroethoxy)ethyl]-5-[(4-ethylphenyl)methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C1=CC(CC)=CC=C1CC1=CC([C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)=C(CCOCC(F)F)C=C1Cl DMZMZZPXFAVPED-HFBCXCLPSA-N 0.000 claims 1
- LQMDPMOJRGTNTR-RTJMFUJLSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-5-[(4-ethoxyphenyl)methyl]-2-(2-prop-2-ynoxyethyl)phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C1=CC(OCC)=CC=C1CC1=CC([C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)=C(CCOCC#C)C=C1Cl LQMDPMOJRGTNTR-RTJMFUJLSA-N 0.000 claims 1
- DWOHGQCZUVZPOW-RXFVIIJJSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-5-[(4-ethoxyphenyl)methyl]-2-[2-(2-fluoroethoxy)ethyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C1=CC(OCC)=CC=C1CC1=CC([C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)=C(CCOCCF)C=C1Cl DWOHGQCZUVZPOW-RXFVIIJJSA-N 0.000 claims 1
- MAISLFRSPARSGN-GEMFNBEASA-N (2s,3r,4r,5s,6r)-2-[4-chloro-5-[(4-ethylphenyl)methyl]-2-(2-hydroxypropoxymethyl)phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C1=CC(CC)=CC=C1CC1=CC([C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)=C(COCC(C)O)C=C1Cl MAISLFRSPARSGN-GEMFNBEASA-N 0.000 claims 1
- JAAKCPJMYZNUIK-RXFVIIJJSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-5-[(4-ethylphenyl)methyl]-2-(2-methoxyethoxymethyl)phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C1=CC(CC)=CC=C1CC1=CC([C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)=C(COCCOC)C=C1Cl JAAKCPJMYZNUIK-RXFVIIJJSA-N 0.000 claims 1
- DMHDNNYWKKEIJY-RTJMFUJLSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-5-[(4-ethylphenyl)methyl]-2-(2-prop-2-ynoxyethyl)phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C1=CC(CC)=CC=C1CC1=CC([C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)=C(CCOCC#C)C=C1Cl DMHDNNYWKKEIJY-RTJMFUJLSA-N 0.000 claims 1
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- YCPICDNLSPCVHC-RXFVIIJJSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-5-[(4-ethylphenyl)methyl]-2-(prop-2-enoxymethyl)phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C1=CC(CC)=CC=C1CC1=CC([C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)=C(COCC=C)C=C1Cl YCPICDNLSPCVHC-RXFVIIJJSA-N 0.000 claims 1
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| DE10258007B4 (de) | 2002-12-12 | 2006-02-09 | Sanofi-Aventis Deutschland Gmbh | Aromatische Fluorglycosidderivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zur Herstellung dieser Arzneimittel |
| ES2567571T3 (es) * | 2003-03-14 | 2016-04-25 | Astellas Pharma Inc. | Derivados de C-glucósido y sales de los mismos |
| JP2004300102A (ja) | 2003-03-31 | 2004-10-28 | Kissei Pharmaceut Co Ltd | 縮合複素環誘導体、それを含有する医薬組成物およびその医薬用途 |
| JP2004359630A (ja) * | 2003-06-06 | 2004-12-24 | Yamanouchi Pharmaceut Co Ltd | ジフルオロジフェニルメタン誘導体及びその塩 |
| TW200524951A (en) | 2003-08-01 | 2005-08-01 | Janssen Pharmaceutica Nv | Substituted benzimidazole-, benztriazole-, and benzimidazolone-O-glucosides |
| CA2549015A1 (en) | 2003-08-01 | 2005-02-10 | Janssen Pharmaceutica N.V. | Substituted fused heterocyclic c-glycosides |
| EP2514756B1 (en) | 2003-08-01 | 2014-12-17 | Mitsubishi Tanabe Pharma Corporation | Novel compounds having inhibitory activity against sodium-dependant glucose transporter |
| US7371732B2 (en) | 2003-12-22 | 2008-05-13 | Boehringer Ingelheim International Gmbh | Glucopyranosyloxy-substituted aromatic compounds, medicaments containing such compounds, their use and process for their manufacture |
| EP1721904A4 (en) | 2004-03-04 | 2010-07-14 | Kissei Pharmaceutical | HETEROCYCLIC DERIVED FADE; MEDICAL COMPOSITION CONTAINING THE DERIVATIVE AND MEDICAL USE |
| PL1730131T3 (pl) | 2004-03-16 | 2012-10-31 | Boehringer Ingelheim Int | Glukopiranozylo-podstawione pochodne benzenu, środki lecznicze zawierające te związki, ich zastosowanie i sposób ich wytwarzania |
| DE102004012676A1 (de) * | 2004-03-16 | 2005-10-06 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Glucopyranosyl-substituierte Phenyle, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstellung |
| TW200606129A (en) | 2004-07-26 | 2006-02-16 | Chugai Pharmaceutical Co Ltd | Novel cyclohexane derivative, its prodrug, its salt and diabetic therapeutic agent containing the same |
| EP1828216B1 (en) * | 2004-12-16 | 2008-09-10 | Boehringer Ingelheim International GmbH | Glucopyranosyl-substituted benzene derivatives, medicaments containing such compounds, their use and process for their manufacture |
| TW200637839A (en) * | 2005-01-07 | 2006-11-01 | Taisho Pharmaceutical Co Ltd | 1-thio-d-glucitol derivatives |
| DE602006011453D1 (de) | 2005-04-15 | 2010-02-11 | Boehringer Ingelheim Pharma | Glucopyranosyl-substituierte (heteroaryloxy-benzyl)-benzen-derivate als sglt-inhibitoren |
-
2008
- 2008-04-01 AU AU2008232419A patent/AU2008232419B2/en not_active Ceased
- 2008-04-01 RU RU2009140298/04A patent/RU2492175C2/ru not_active IP Right Cessation
- 2008-04-01 DK DK08744883.3T patent/DK2064222T3/da active
- 2008-04-01 KR KR1020097022926A patent/KR101506935B1/ko not_active Expired - Fee Related
- 2008-04-01 JP JP2010502246A patent/JP5583003B2/ja not_active Expired - Fee Related
- 2008-04-01 CN CN201510041214.8A patent/CN104803957A/zh active Pending
- 2008-04-01 BR BRPI0809607-4A patent/BRPI0809607A2/pt not_active IP Right Cessation
- 2008-04-01 WO PCT/US2008/059047 patent/WO2008122014A1/en not_active Ceased
- 2008-04-01 US US12/060,767 patent/US7838498B2/en not_active Expired - Fee Related
- 2008-04-01 CN CN200880011535A patent/CN101652377A/zh active Pending
- 2008-04-01 CA CA2682202A patent/CA2682202C/en not_active Expired - Fee Related
- 2008-04-01 EP EP08744883.3A patent/EP2064222B1/en active Active
- 2008-04-01 AR ARP080101366A patent/AR065913A1/es not_active Application Discontinuation
- 2008-04-01 ES ES08744883.3T patent/ES2466672T3/es active Active
- 2008-04-02 TW TW097112029A patent/TWI405575B/zh not_active IP Right Cessation
-
2009
- 2009-09-21 IL IL201065A patent/IL201065A/en active IP Right Grant
-
2016
- 2016-01-29 HK HK16101045.5A patent/HK1212982A1/zh unknown
-
2018
- 2018-02-08 AR ARP180100299A patent/AR110968A2/es unknown
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