JP2004500416A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2004500416A5 JP2004500416A5 JP2001572523A JP2001572523A JP2004500416A5 JP 2004500416 A5 JP2004500416 A5 JP 2004500416A5 JP 2001572523 A JP2001572523 A JP 2001572523A JP 2001572523 A JP2001572523 A JP 2001572523A JP 2004500416 A5 JP2004500416 A5 JP 2004500416A5
- Authority
- JP
- Japan
- Prior art keywords
- inhibitor
- compound according
- hydrogen
- formula
- 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
Links
- 150000001875 compounds Chemical class 0.000 description 18
- 125000000217 alkyl group Chemical group 0.000 description 10
- 229910052739 hydrogen Inorganic materials 0.000 description 10
- 239000001257 hydrogen Substances 0.000 description 10
- 0 CC1(C(**)=C(*)C(*)=C(*)*1)O[C@@]([C@]([C@@]1O)O)O[C@](CO)[C@]1O Chemical compound CC1(C(**)=C(*)C(*)=C(*)*1)O[C@@]([C@]([C@@]1O)O)O[C@](CO)[C@]1O 0.000 description 9
- -1 CF 3 Chemical group 0.000 description 9
- 239000003112 inhibitor Substances 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 229910052717 sulfur Inorganic materials 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 229940125708 antidiabetic agent Drugs 0.000 description 5
- 239000003472 antidiabetic agent Substances 0.000 description 5
- 150000002431 hydrogen Chemical class 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Cc1ccccc1 Chemical compound Cc1ccccc1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- 229940123518 Sodium/glucose cotransporter 2 inhibitor Drugs 0.000 description 4
- 239000003524 antilipemic agent Substances 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 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 description 4
- 239000000883 anti-obesity agent Substances 0.000 description 3
- 229940125710 antiobesity agent Drugs 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 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 description 2
- 102000004877 Insulin Human genes 0.000 description 2
- 108090001061 Insulin Proteins 0.000 description 2
- 102100040918 Pro-glucagon Human genes 0.000 description 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 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 2
- 125000001072 heteroaryl group Chemical group 0.000 description 2
- 229940125396 insulin Drugs 0.000 description 2
- DHHVAGZRUROJKS-UHFFFAOYSA-N phentermine Chemical compound CC(C)(N)CC1=CC=CC=C1 DHHVAGZRUROJKS-UHFFFAOYSA-N 0.000 description 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 description 2
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 2
- 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 description 1
- ZGGHKIMDNBDHJB-NRFPMOEYSA-M (3R,5S)-fluvastatin sodium Chemical compound [Na+].C12=CC=CC=C2N(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C1C1=CC=C(F)C=C1 ZGGHKIMDNBDHJB-NRFPMOEYSA-M 0.000 description 1
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 1
- YKYIFUROKBDHCY-ONEGZZNKSA-N (e)-4-ethoxy-1,1,1-trifluorobut-3-en-2-one Chemical group CCO\C=C\C(=O)C(F)(F)F YKYIFUROKBDHCY-ONEGZZNKSA-N 0.000 description 1
- BOVGTQGAOIONJV-BETUJISGSA-N 1-[(3ar,6as)-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-2-yl]-3-(4-methylphenyl)sulfonylurea Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NN1C[C@H]2CCC[C@H]2C1 BOVGTQGAOIONJV-BETUJISGSA-N 0.000 description 1
- ILPUOPPYSQEBNJ-UHFFFAOYSA-N 2-methyl-2-phenoxypropanoic acid Chemical class OC(=O)C(C)(C)OC1=CC=CC=C1 ILPUOPPYSQEBNJ-UHFFFAOYSA-N 0.000 description 1
- SWLAMJPTOQZTAE-UHFFFAOYSA-N 4-[2-[(5-chloro-2-methoxybenzoyl)amino]ethyl]benzoic acid Chemical compound COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(C(O)=O)C=C1 SWLAMJPTOQZTAE-UHFFFAOYSA-N 0.000 description 1
- QBQLYIISSRXYKL-UHFFFAOYSA-N 4-[[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]methyl]-1,2-oxazolidine-3,5-dione Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC1C(=O)NOC1=O QBQLYIISSRXYKL-UHFFFAOYSA-N 0.000 description 1
- PTQXTEKSNBVPQJ-UHFFFAOYSA-N Avasimibe Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1CC(=O)NS(=O)(=O)OC1=C(C(C)C)C=CC=C1C(C)C PTQXTEKSNBVPQJ-UHFFFAOYSA-N 0.000 description 1
- 229940123208 Biguanide Drugs 0.000 description 1
- RQVCVOSPASWLDD-YMQHIKHWSA-N CCc1ccc(Cc2ccccc2O[C@@H]([C@@H]([C@H]2O)O)O[C@H](CO)[C@H]2O)cc1 Chemical compound CCc1ccc(Cc2ccccc2O[C@@H]([C@@H]([C@H]2O)O)O[C@H](CO)[C@H]2O)cc1 RQVCVOSPASWLDD-YMQHIKHWSA-N 0.000 description 1
- TYLMEYDOPQBMCY-UJWQCDCRSA-N Cc(cc1)ccc1Oc1ccccc1O[C@@H]([C@@H]([C@H]1O)O)O[C@H](CO)[C@H]1O Chemical compound Cc(cc1)ccc1Oc1ccccc1O[C@@H]([C@@H]([C@H]1O)O)O[C@H](CO)[C@H]1O TYLMEYDOPQBMCY-UJWQCDCRSA-N 0.000 description 1
- QOJMGTFKCKUFFN-IQZDNPOKSA-N Cc(cc1)ccc1Sc1ccccc1O[C@@H]([C@@H]([C@H]1O)O)O[C@H](CO)[C@H]1O Chemical compound Cc(cc1)ccc1Sc1ccccc1O[C@@H]([C@@H]([C@H]1O)O)O[C@H](CO)[C@H]1O QOJMGTFKCKUFFN-IQZDNPOKSA-N 0.000 description 1
- PJFAFCHMHLNMSX-OUUBHVDSSA-N Cc1ccc(Cc(cccc2)c2O[C@@H]([C@@H]([C@H]2O)O)O[C@H](CO)[C@H]2O)cc1 Chemical compound Cc1ccc(Cc(cccc2)c2O[C@@H]([C@@H]([C@H]2O)O)O[C@H](CO)[C@H]2O)cc1 PJFAFCHMHLNMSX-OUUBHVDSSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RKWGIWYCVPQPMF-UHFFFAOYSA-N Chloropropamide Chemical compound CCCNC(=O)NS(=O)(=O)C1=CC=C(Cl)C=C1 RKWGIWYCVPQPMF-UHFFFAOYSA-N 0.000 description 1
- 101710198884 GATA-type zinc finger protein 1 Proteins 0.000 description 1
- HEMJJKBWTPKOJG-UHFFFAOYSA-N Gemfibrozil Chemical compound CC1=CC=C(C)C(OCCCC(C)(C)C(O)=O)=C1 HEMJJKBWTPKOJG-UHFFFAOYSA-N 0.000 description 1
- 101800000224 Glucagon-like peptide 1 Proteins 0.000 description 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 description 1
- 102000004366 Glucosidases Human genes 0.000 description 1
- 108010056771 Glucosidases Proteins 0.000 description 1
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 description 1
- 229940122355 Insulin sensitizer Drugs 0.000 description 1
- 102000000853 LDL receptors Human genes 0.000 description 1
- 108010001831 LDL receptors Proteins 0.000 description 1
- 229940086609 Lipase inhibitor Drugs 0.000 description 1
- 239000000867 Lipoxygenase Inhibitor Substances 0.000 description 1
- 229940122142 Lipoxygenase inhibitor Drugs 0.000 description 1
- IBAQFPQHRJAVAV-ULAWRXDQSA-N Miglitol Chemical compound OCCN1C[C@H](O)[C@@H](O)[C@H](O)[C@H]1CO IBAQFPQHRJAVAV-ULAWRXDQSA-N 0.000 description 1
- PCZOHLXUXFIOCF-UHFFFAOYSA-N Monacolin X Natural products C12C(OC(=O)C(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 PCZOHLXUXFIOCF-UHFFFAOYSA-N 0.000 description 1
- QKSXOGUJWVSOIM-OGJJZOIMSA-N OC[C@H]([C@H]([C@@H]([C@H]1O)O)O)O[C@H]1Oc1ccccc1-c1nc(cccc2)c2[o]1 Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O)O[C@H]1Oc1ccccc1-c1nc(cccc2)c2[o]1 QKSXOGUJWVSOIM-OGJJZOIMSA-N 0.000 description 1
- IBAJJTKEICOOTO-NQNKBUKLSA-N OC[C@H]([C@H]([C@@H]([C@H]1O)O)O)O[C@H]1Oc1ccccc1Cc1c[s]cc1 Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O)O[C@H]1Oc1ccccc1Cc1c[s]cc1 IBAJJTKEICOOTO-NQNKBUKLSA-N 0.000 description 1
- 102000023984 PPAR alpha Human genes 0.000 description 1
- 229940080774 Peroxisome proliferator-activated receptor gamma agonist Drugs 0.000 description 1
- TUZYXOIXSAXUGO-UHFFFAOYSA-N Pravastatin Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(O)C=C21 TUZYXOIXSAXUGO-UHFFFAOYSA-N 0.000 description 1
- RYMZZMVNJRMUDD-UHFFFAOYSA-N SJ000286063 Natural products C12C(OC(=O)C(C)(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 RYMZZMVNJRMUDD-UHFFFAOYSA-N 0.000 description 1
- 229940123495 Squalene synthetase inhibitor Drugs 0.000 description 1
- 229940100389 Sulfonylurea Drugs 0.000 description 1
- KJADKKWYZYXHBB-XBWDGYHZSA-N Topiramic acid Chemical compound C1O[C@@]2(COS(N)(=O)=O)OC(C)(C)O[C@H]2[C@@H]2OC(C)(C)O[C@@H]21 KJADKKWYZYXHBB-XBWDGYHZSA-N 0.000 description 1
- 102100038129 Transcription factor Dp family member 3 Human genes 0.000 description 1
- 229960002632 acarbose Drugs 0.000 description 1
- XUFXOAAUWZOOIT-UHFFFAOYSA-N acarviostatin I01 Natural products OC1C(O)C(NC2C(C(O)C(O)C(CO)=C2)O)C(C)OC1OC(C(C1O)O)C(CO)OC1OC1C(CO)OC(O)C(O)C1O XUFXOAAUWZOOIT-UHFFFAOYSA-N 0.000 description 1
- 239000000048 adrenergic agonist Substances 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 239000002830 appetite depressant Substances 0.000 description 1
- 125000005018 aryl alkenyl group Chemical group 0.000 description 1
- 229950010046 avasimibe Drugs 0.000 description 1
- 150000004283 biguanides Chemical group 0.000 description 1
- 229960005110 cerivastatin Drugs 0.000 description 1
- SEERZIQQUAZTOL-ANMDKAQQSA-N cerivastatin Chemical compound COCC1=C(C(C)C)N=C(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC(O)=O)=C1C1=CC=C(F)C=C1 SEERZIQQUAZTOL-ANMDKAQQSA-N 0.000 description 1
- MVCQKIKWYUURMU-UHFFFAOYSA-N cetilistat Chemical compound C1=C(C)C=C2C(=O)OC(OCCCCCCCCCCCCCCCC)=NC2=C1 MVCQKIKWYUURMU-UHFFFAOYSA-N 0.000 description 1
- 229950002397 cetilistat Drugs 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229960001761 chlorpropamide Drugs 0.000 description 1
- 229960001214 clofibrate Drugs 0.000 description 1
- KNHUKKLJHYUCFP-UHFFFAOYSA-N clofibrate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 KNHUKKLJHYUCFP-UHFFFAOYSA-N 0.000 description 1
- DLNKOYKMWOXYQA-UHFFFAOYSA-N dl-pseudophenylpropanolamine Natural products CC(N)C(O)C1=CC=CC=C1 DLNKOYKMWOXYQA-UHFFFAOYSA-N 0.000 description 1
- 229960003638 dopamine Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229960002297 fenofibrate Drugs 0.000 description 1
- YMTINGFKWWXKFG-UHFFFAOYSA-N fenofibrate Chemical compound C1=CC(OC(C)(C)C(=O)OC(C)C)=CC=C1C(=O)C1=CC=C(Cl)C=C1 YMTINGFKWWXKFG-UHFFFAOYSA-N 0.000 description 1
- 229940125753 fibrate Drugs 0.000 description 1
- 229960003765 fluvastatin Drugs 0.000 description 1
- 229960003627 gemfibrozil Drugs 0.000 description 1
- 229960004580 glibenclamide Drugs 0.000 description 1
- 229960000346 gliclazide Drugs 0.000 description 1
- 229960004346 glimepiride Drugs 0.000 description 1
- WIGIZIANZCJQQY-RUCARUNLSA-N glimepiride Chemical compound O=C1C(CC)=C(C)CN1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)N[C@@H]2CC[C@@H](C)CC2)C=C1 WIGIZIANZCJQQY-RUCARUNLSA-N 0.000 description 1
- ZJJXGWJIGJFDTL-UHFFFAOYSA-N glipizide Chemical compound C1=NC(C)=CN=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCCC2)C=C1 ZJJXGWJIGJFDTL-UHFFFAOYSA-N 0.000 description 1
- 229960001381 glipizide Drugs 0.000 description 1
- ZNNLBTZKUZBEKO-UHFFFAOYSA-N glyburide Chemical compound COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCCC2)C=C1 ZNNLBTZKUZBEKO-UHFFFAOYSA-N 0.000 description 1
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 description 1
- 229960004844 lovastatin Drugs 0.000 description 1
- PCZOHLXUXFIOCF-BXMDZJJMSA-N lovastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 PCZOHLXUXFIOCF-BXMDZJJMSA-N 0.000 description 1
- QLJODMDSTUBWDW-UHFFFAOYSA-N lovastatin hydroxy acid Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(C)C=C21 QLJODMDSTUBWDW-UHFFFAOYSA-N 0.000 description 1
- 229950004994 meglitinide Drugs 0.000 description 1
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 description 1
- 229960003105 metformin Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229960001110 miglitol Drugs 0.000 description 1
- 229960000698 nateglinide Drugs 0.000 description 1
- OELFLUMRDSZNSF-BRWVUGGUSA-N nateglinide Chemical compound C1C[C@@H](C(C)C)CC[C@@H]1C(=O)N[C@@H](C(O)=O)CC1=CC=CC=C1 OELFLUMRDSZNSF-BRWVUGGUSA-N 0.000 description 1
- 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 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- AHLBNYSZXLDEJQ-FWEHEUNISA-N orlistat Chemical group CCCCCCCCCCC[C@H](OC(=O)[C@H](CC(C)C)NC=O)C[C@@H]1OC(=O)[C@H]1CCCCCC AHLBNYSZXLDEJQ-FWEHEUNISA-N 0.000 description 1
- 229960001243 orlistat Drugs 0.000 description 1
- 108091008725 peroxisome proliferator-activated receptors alpha Proteins 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 229960003562 phentermine Drugs 0.000 description 1
- DLNKOYKMWOXYQA-APPZFPTMSA-N phenylpropanolamine Chemical compound C[C@@H](N)[C@H](O)C1=CC=CC=C1 DLNKOYKMWOXYQA-APPZFPTMSA-N 0.000 description 1
- 229960000395 phenylpropanolamine Drugs 0.000 description 1
- 229960005095 pioglitazone Drugs 0.000 description 1
- 229960002797 pitavastatin Drugs 0.000 description 1
- RHGYHLPFVJEAOC-FFNUKLMVSA-L pitavastatin calcium Chemical compound [Ca+2].[O-]C(=O)C[C@H](O)C[C@H](O)\C=C\C1=C(C2CC2)N=C2C=CC=CC2=C1C1=CC=C(F)C=C1.[O-]C(=O)C[C@H](O)C[C@H](O)\C=C\C1=C(C2CC2)N=C2C=CC=CC2=C1C1=CC=C(F)C=C1 RHGYHLPFVJEAOC-FFNUKLMVSA-L 0.000 description 1
- 229960002965 pravastatin Drugs 0.000 description 1
- TUZYXOIXSAXUGO-PZAWKZKUSA-N pravastatin Chemical compound C1=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC(O)=O)[C@H]2[C@@H](OC(=O)[C@@H](C)CC)C[C@H](O)C=C21 TUZYXOIXSAXUGO-PZAWKZKUSA-N 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 229960002354 repaglinide Drugs 0.000 description 1
- 229960004586 rosiglitazone Drugs 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 229960004425 sibutramine Drugs 0.000 description 1
- UNAANXDKBXWMLN-UHFFFAOYSA-N sibutramine Chemical compound C=1C=C(Cl)C=CC=1C1(C(N(C)C)CC(C)C)CCC1 UNAANXDKBXWMLN-UHFFFAOYSA-N 0.000 description 1
- 229960002855 simvastatin Drugs 0.000 description 1
- RYMZZMVNJRMUDD-HGQWONQESA-N simvastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)C(C)(C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 RYMZZMVNJRMUDD-HGQWONQESA-N 0.000 description 1
- 239000004059 squalene synthase inhibitor Substances 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- 102000004217 thyroid hormone receptors Human genes 0.000 description 1
- 108090000721 thyroid hormone receptors Proteins 0.000 description 1
- 229960004394 topiramate Drugs 0.000 description 1
- GXPHKUHSUJUWKP-UHFFFAOYSA-N troglitazone Chemical compound C1CC=2C(C)=C(O)C(C)=C(C)C=2OC1(C)COC(C=C1)=CC=C1CC1SC(=O)NC1=O GXPHKUHSUJUWKP-UHFFFAOYSA-N 0.000 description 1
- 229960001641 troglitazone Drugs 0.000 description 1
- GXPHKUHSUJUWKP-NTKDMRAZSA-N troglitazone Natural products C([C@@]1(OC=2C(C)=C(C(=C(C)C=2CC1)O)C)C)OC(C=C1)=CC=C1C[C@H]1SC(=O)NC1=O GXPHKUHSUJUWKP-NTKDMRAZSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US19309400P | 2000-03-30 | 2000-03-30 | |
| US60/193,094 | 2000-03-30 | ||
| PCT/US2001/010092 WO2001074834A1 (en) | 2000-03-30 | 2001-03-29 | O-aryl glucoside sglt2 inhibitors and method |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2004500416A JP2004500416A (ja) | 2004-01-08 |
| JP2004500416A5 true JP2004500416A5 (OSRAM) | 2008-05-22 |
| JP4986202B2 JP4986202B2 (ja) | 2012-07-25 |
Family
ID=22712264
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001572523A Expired - Fee Related JP4986202B2 (ja) | 2000-03-30 | 2001-03-29 | Ｏ−アリールグルコシドｓｇｌｔ２抑制剤および方法 |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US6683056B2 (OSRAM) |
| EP (1) | EP1268502B1 (OSRAM) |
| JP (1) | JP4986202B2 (OSRAM) |
| KR (1) | KR100798203B1 (OSRAM) |
| CN (1) | CN1275977C (OSRAM) |
| AT (1) | ATE316976T1 (OSRAM) |
| AU (2) | AU4959801A (OSRAM) |
| BR (1) | BR0109326A (OSRAM) |
| CA (1) | CA2404373A1 (OSRAM) |
| DE (1) | DE60117012T2 (OSRAM) |
| ES (1) | ES2258079T3 (OSRAM) |
| HU (1) | HUP0301513A3 (OSRAM) |
| IL (1) | IL151473A0 (OSRAM) |
| MX (1) | MXPA02009522A (OSRAM) |
| NO (1) | NO20024642L (OSRAM) |
| NZ (1) | NZ520822A (OSRAM) |
| PL (1) | PL365176A1 (OSRAM) |
| RU (1) | RU2269540C2 (OSRAM) |
| WO (1) | WO2001074834A1 (OSRAM) |
| ZA (1) | ZA200207030B (OSRAM) |
Families Citing this family (165)
| 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 |
| US6515117B2 (en) * | 1999-10-12 | 2003-02-04 | Bristol-Myers Squibb Company | C-aryl glucoside SGLT2 inhibitors and method |
| BR0109323A (pt) * | 2000-03-17 | 2002-12-24 | Kissei Pharmaceutical | Derivados de gluco piranosiloxi benzil benzeno, composições medicinais contendo os mesmos e intermediários para a preparação dos derivados |
| CN1293087C (zh) * | 2000-09-29 | 2007-01-03 | 橘生药品工业株式会社 | 吡喃葡糖氧基苄基苯衍生物及其药物组合物 |
| US7053060B2 (en) * | 2000-11-30 | 2006-05-30 | Kissei Pharmaceutical Co., Ltd. | Glucopyranosyloxybenzylbenzene derivatives, medicinal compositions containing the same and intermediates in the production thereof |
| RU2317302C2 (ru) | 2000-12-28 | 2008-02-20 | Киссеи Фармасьютикал Ко., Лтд. | Производные глюкопиранозилоксипиразола и их применение в лекарственных средствах |
| TWI255817B (en) * | 2001-02-14 | 2006-06-01 | Kissei Pharmaceutical | Glucopyranosyloxybenzylbenzene derivatives and medicinal use thereof |
| ATE442148T1 (de) * | 2001-04-04 | 2009-09-15 | Ortho Mcneil Janssen Pharm | Kombinationstherapie durch glukoseresorptionshemmer und retinoid x rezeptorenmodulatoren |
| ES2321815T3 (es) | 2001-04-04 | 2009-06-12 | Ortho-Mcneil-Janssen Pharmaceuticals, Inc. | Combinacion terapeutica que comprende inhibidores de reabsorcion e glucosa y moduladores ppar. |
| KR100882179B1 (ko) * | 2001-06-20 | 2009-02-06 | 깃세이 야쿠힌 고교 가부시키가이샤 | 함질소 복소환 유도체, 그것을 함유하는 의약 조성물, 그의약 용도 및 그 제조 중간체 |
| WO2003011880A1 (fr) * | 2001-07-31 | 2003-02-13 | Kissei Pharmaceutical Co., Ltd. | Derive de glucopyranosyloxybenzylbenzene, composition medicinale contenant ce derive, usage medicinal de cette composition et produit intermediaire pour produire cette composition |
| MXPA04009229A (es) * | 2002-03-22 | 2004-11-26 | Kissei Pharmaceutical | Cristales derivados de glucopiranosiloxibencil benceno. |
| US7956041B2 (en) * | 2002-04-26 | 2011-06-07 | Ajinomoto Co., Inc. | Prophylactic and therapeutic agent of diabetes mellitus |
| CA2494179C (en) * | 2002-08-08 | 2012-04-24 | Kissei Pharmaceutical Co., Ltd. | Pyrazole derivative, medicinal composition containing the same, medicinal use thereof, and intermediate for production thereof |
| RU2322449C2 (ru) * | 2002-08-09 | 2008-04-20 | Тайсо Фармасьютикал Ко., Лтд. | ПРОИЗВОДНЫЕ АРИЛ 5-ТИО-β-D-ГЛЮКОПИРАНОЗИДА И ТЕРАПЕВТИЧЕСКИЕ СРЕДСТВА ПРИ ДИАБЕТЕ, СОДЕРЖАЩИЕ ИХ |
| JP4651934B2 (ja) * | 2002-12-04 | 2011-03-16 | キッセイ薬品工業株式会社 | ベンジルフェノール誘導体、それを含有する医薬組成物およびその医薬用途 |
| 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 |
| JP4679155B2 (ja) * | 2002-12-25 | 2011-04-27 | キッセイ薬品工業株式会社 | 含窒素複素環誘導体、それを含有する医薬組成物およびその医薬用途 |
| 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 |
| CN1761676A (zh) * | 2003-04-01 | 2006-04-19 | 大正制药株式会社 | 杂芳基5－硫代－β－D－吡喃葡糖苷衍生物及含有该衍生物的糖尿病治疗药 |
| US8785403B2 (en) | 2003-08-01 | 2014-07-22 | Mitsubishi Tanabe Pharma Corporation | Glucopyranoside compound |
| WO2005012243A2 (en) * | 2003-08-01 | 2005-02-10 | Janssen Pharmaceutica N.V. | Substituted indole-o-glucosides |
| RS53365B (sr) * | 2003-08-01 | 2014-10-31 | Mitsubishi Tanabe Pharma Corporation | Nova jedinjenja koja imaju inhibitorno dejstvo na transporter glukoze zavisan od natrijuma |
| RS20060320A (sr) * | 2003-08-01 | 2008-08-07 | Janssen Pharmaceutica N.V., | Supstituisani indazol-o-glukozidi |
| WO2005012242A2 (en) * | 2003-08-01 | 2005-02-10 | Janssen Pharmaceutica Nv | Substituted benzimidazole-, benztriazole-, and benzimidazolone-o-glucosides |
| US7094763B2 (en) * | 2003-08-01 | 2006-08-22 | Janssen Pharaceutica, N.V. | Substituted fused heterocyclic C-glycosides |
| UA86042C2 (en) | 2003-08-01 | 2009-03-25 | Янссен Фармацевтика Н.В. | Substituted indazole-o-glucosides |
| JP4568488B2 (ja) * | 2003-09-05 | 2010-10-27 | 花王株式会社 | イソプロピルメチルフェノール配糖体 |
| EP1516665A1 (en) | 2003-09-18 | 2005-03-23 | Sony International (Europe) GmbH | A method of immobilizing and stretching a nucleic acid on a substrate |
| DE10361133A1 (de) * | 2003-12-22 | 2005-07-21 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Glucopyranosyloxy-substituierte Aromaten, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstellung |
| 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 |
| AU2005219779B2 (en) * | 2004-03-04 | 2011-04-14 | Kissei Pharmaceutical Co., Ltd. | Fused heterocycle derivative, medicinal composition containing the same, and medicinal use thereof |
| CN103467423B (zh) | 2004-03-16 | 2016-03-16 | 贝林格尔.英格海姆国际有限公司 | 吡喃葡萄糖基取代的苯基衍生物、含该化合物的药物、其用途及其制造方法 |
| WO2005095373A1 (ja) * | 2004-03-31 | 2005-10-13 | Kissei Pharmaceutical Co., Ltd. | ナフタレン誘導体、それを含有する医薬組成物およびその医薬用途 |
| WO2005095372A1 (ja) * | 2004-03-31 | 2005-10-13 | Kissei Pharmaceutical Co., Ltd. | ナフタレン誘導体、それを含有する医薬組成物及びその医薬用途 |
| US20070185197A1 (en) * | 2004-03-31 | 2007-08-09 | Hideki Fujikura | Phenol derivative, medicinal composition containing the same, and medicinal use thereof |
| US20050261292A1 (en) * | 2004-05-19 | 2005-11-24 | Solvay Pharmaceuticals Gmbh | Pharmaceutical composition containing N-sulfamoyl-N'-arylpiperazines for the treatment or inhibition of obesity and related conditions |
| 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 |
| JP5046370B2 (ja) * | 2004-09-29 | 2012-10-10 | キッセイ薬品工業株式会社 | １−（β−Ｄ−グリコピラノシル）−３−置換含窒素ヘテロ環化合物、それを含有する医薬組成物及びその医薬用途 |
| DE102004058449A1 (de) * | 2004-12-03 | 2006-06-14 | Merck Patent Gmbh | Tetrahydropyranderivate |
| 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 |
| TW200637869A (en) | 2005-01-28 | 2006-11-01 | Chugai Pharmaceutical Co Ltd | The spiroketal derivatives and the use as therapeutical agent for diabetes of the same |
| TWI365186B (en) * | 2005-01-31 | 2012-06-01 | Mitsubishi Tanabe Pharma Corp | Indole derivatives |
| JP5073948B2 (ja) * | 2005-01-31 | 2012-11-14 | 田辺三菱製薬株式会社 | 医薬組成物 |
| AR053329A1 (es) * | 2005-01-31 | 2007-05-02 | Tanabe Seiyaku Co | Derivados de indol utiles como inhibidores de los transportadores de glucosa dependientes del sodio (sglt) |
| WO2006089872A1 (en) | 2005-02-23 | 2006-08-31 | Boehringer Ingelheim International Gmbh | Glucopyranosyl-substituted ( (hetero)arylethynyl-benzyd-benzene derivatives and use thereof as sodium-dependent glucose cotransporter 2 (sglt2) inhibitors |
| EP1874787B1 (en) | 2005-04-15 | 2009-12-30 | Boehringer Ingelheim International GmbH | Glucopyranosyl-substituted (heteroaryloxy-benzyl)-benzene derivatives as sglt inhibitors |
| US7723309B2 (en) | 2005-05-03 | 2010-05-25 | Boehringer Ingelheim International Gmbh | Crystalline forms of 1-chloro-4-(β-D-glucopyranos-1-yl)-2-[4-((R)-tetrahydrofuran-3-yloxy)-benzyl]-benzene, a method for its preparation and the use thereof for preparing medicaments |
| 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 |
| US7772191B2 (en) | 2005-05-10 | 2010-08-10 | Boehringer Ingelheim International Gmbh | Processes for preparing of glucopyranosyl-substituted benzyl-benzene derivatives and intermediates therein |
| WO2007014894A2 (en) | 2005-07-27 | 2007-02-08 | Boehringer Ingelheim International Gmbh | Glucopyranosyl-substituted ( (hetero) cycloalyklethynyl-benzyl) -benzene derivatives and use thereof as sodium-dependent glucose cotransporter (sglt) inhibitors |
| UY29694A1 (es) * | 2005-07-28 | 2007-02-28 | Boehringer Ingelheim Int | Metodos para prevenir y tratar trastornos metabolicos y nuevos derivados de pirazol-o-glucosido |
| JP5175191B2 (ja) | 2005-08-30 | 2013-04-03 | 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 | グリコピラノシル置換ベンジルベンゼン誘導体、該化合物を含有する医薬品及びその使用と製造方法 |
| WO2007028814A1 (en) | 2005-09-08 | 2007-03-15 | Boehringer Ingelheim International Gmbh | CRYSTALLINE FORMS OF 1-CHLORO-4-(ß-D-GLUCOPYRANOS-1-YL)-2-(4-ETHYNYL-BENZYL)-BENZENE, METHODS FOR ITS PREPARATION AND THE USE THEREOF FOR PREPARING MEDICAMENTS |
| AR056195A1 (es) | 2005-09-15 | 2007-09-26 | Boehringer Ingelheim Int | Procedimientos para preparar derivados de (etinil-bencil)-benceno sustituidos de glucopiranosilo y compuestos intermedios de los mismos |
| ATE517099T1 (de) | 2006-02-15 | 2011-08-15 | Boehringer Ingelheim Int | Glucopyranosyl-substituierte benzonitril-derivate,pharmazeutische zusammensetzungen mit derartigen verbindungen, ihre verwendung und herstellungsverfahren dafür |
| TWI370818B (en) * | 2006-04-05 | 2012-08-21 | Astellas Pharma Inc | Cocrystal of c-glycoside derivative and l-proline |
| EP1854806A1 (en) * | 2006-05-02 | 2007-11-14 | MPG Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V. | Thioglycosides as pharmaceutically active agents |
| PE20080697A1 (es) | 2006-05-03 | 2008-08-05 | Boehringer Ingelheim Int | Derivados de benzonitrilo sustituidos con glucopiranosilo, composiciones farmaceuticas que contienen compuestos de este tipo, su uso y procedimiento para su fabricacion |
| PE20110235A1 (es) | 2006-05-04 | 2011-04-14 | Boehringer Ingelheim Int | Combinaciones farmaceuticas que comprenden linagliptina y metmorfina |
| JP5067644B2 (ja) * | 2006-05-19 | 2012-11-07 | 大正製薬株式会社 | Ｃ−フェニルグリシト−ル化合物 |
| US7803778B2 (en) * | 2006-05-23 | 2010-09-28 | Theracos, Inc. | Glucose transport inhibitors and methods of use |
| WO2007143052A1 (en) * | 2006-06-01 | 2007-12-13 | Glycomimetics, Inc. | Galactosides and thiodigalactosides as inhibitors of pa-il lectin from pseudomonas |
| DE102006028862A1 (de) | 2006-06-23 | 2007-12-27 | Merck Patent Gmbh | 3-Amino-imidazo[1,2-a]pyridinderivate |
| US7919598B2 (en) | 2006-06-28 | 2011-04-05 | Bristol-Myers Squibb Company | Crystal structures of SGLT2 inhibitors and processes for preparing same |
| TWI418556B (zh) * | 2006-07-27 | 2013-12-11 | Mitsubishi Tanabe Pharma Corp | 吲哚衍生物 |
| TW200817424A (en) * | 2006-08-04 | 2008-04-16 | Daiichi Sankyo Co Ltd | Benzylphenyl glucopyranoside derivatives |
| TWI499414B (zh) | 2006-09-29 | 2015-09-11 | Lexicon Pharmaceuticals Inc | 鈉與葡萄糖第２型共同運輸體（ｃｏ-ｔｒａｎｓｐｏｒｔｅｒ ２）的抑制物與其應用方法 |
| CN101611032B (zh) * | 2006-12-04 | 2012-07-18 | 詹森药业有限公司 | 作为抗糖尿病药的含噻吩基的吡喃葡糖基衍生物 |
| UY30730A1 (es) * | 2006-12-04 | 2008-07-03 | Mitsubishi Tanabe Pharma Corp | Forma cristalina del hemihidrato de 1-(b (beta)-d-glucopiranosil) -4-metil-3-[5-(4-fluorofenil) -2-tienilmetil]benceno |
| BRPI0719941A2 (pt) | 2006-12-06 | 2014-04-22 | Smithkline Beecham Corp | Composto, uso de um composto, método para o tratamento de distúrbios ou condições metabólicos, composição farmacêutica, e, processo para a preparação de uma composição farmacêutica |
| US7795228B2 (en) * | 2006-12-28 | 2010-09-14 | Theracos, Inc. | Spiroheterocyclic glycosides and methods of use |
| DE102007008420A1 (de) | 2007-02-21 | 2008-08-28 | Merck Patent Gmbh | Benzimidazolderivate |
| WO2008109591A1 (en) * | 2007-03-08 | 2008-09-12 | Lexicon Pharmaceuticals, Inc. | Phlorizin analogs as inhibitors of sodium glucose co-transporter 2 |
| AU2008232419B2 (en) | 2007-04-02 | 2013-06-20 | Theracos, Inc. | Benzylic glycoside derivatives and methods of use |
| UA107175C2 (uk) * | 2007-07-26 | 2014-12-10 | Спосіб і сполука, призначені для одержання інгібіторів контранспортера натрій-глюкози 2 типу, варіанти | |
| CL2008002427A1 (es) | 2007-08-16 | 2009-09-11 | Boehringer Ingelheim Int | Composicion farmaceutica que comprende 1-cloro-4-(b-d-glucopiranos-1-il)-2-[4-((s)-tetrahidrofurano-3-iloxi)bencil]-benceno combinado con 1-[(4-metilquinazolin-2-il)metil]-3-metil-7-(2-butin-1-il)-8-(3-(r)-aminopiperidin-1-il)xantina; y su uso para tratar diabetes mellitus tipo 2. |
| UA99924C2 (en) | 2007-08-23 | 2012-10-25 | Теракос, Инк. | Benzylbenzol derivatives and using thereof |
| NO2200606T3 (OSRAM) | 2007-09-10 | 2018-03-24 | ||
| DE102007048716A1 (de) | 2007-10-11 | 2009-04-23 | Merck Patent Gmbh | Imidazo[1,2-a]pyrimidinderivate |
| US8252751B2 (en) * | 2007-11-30 | 2012-08-28 | Novartis Ag | Organic compounds |
| UA101004C2 (en) | 2007-12-13 | 2013-02-25 | Теракос, Инк. | Derivatives of benzylphenylcyclohexane and use thereof |
| 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. |
| WO2009096503A1 (ja) * | 2008-01-31 | 2009-08-06 | Daiichi Sankyo Company, Limited | ベンジルフェニルグルコピラノシド誘導体 |
| FR2929615B1 (fr) * | 2008-04-02 | 2010-12-17 | Tfchem | Composes c-aryl glycosides pour le traitement du diabete et de l'obesite. |
| DE102008017590A1 (de) | 2008-04-07 | 2009-10-08 | Merck Patent Gmbh | Glucopyranosidderivate |
| US8791077B2 (en) | 2008-05-22 | 2014-07-29 | Astrazeneca Ab | Method for treating hyperuricemia employing an SGLT2 inhibitor and composition containing same |
| TWI523652B (zh) | 2008-07-15 | 2016-03-01 | 泰瑞克公司 | 氘化苄基苯衍生物及使用方法 |
| SMT201600475T1 (it) | 2008-08-22 | 2017-03-08 | Theracos Sub Llc | Procedimenti per la preparazione di inibitori di sglt2. |
| WO2010023594A1 (en) * | 2008-08-28 | 2010-03-04 | Pfizer Inc. | Dioxa-bicyclo[3.2.1.]octane-2,3,4-triol derivatives |
| US9056850B2 (en) * | 2008-10-17 | 2015-06-16 | Janssen Pharmaceutica N.V. | Process for the preparation of compounds useful as inhibitors of SGLT |
| CN101445527B (zh) * | 2008-12-25 | 2011-09-14 | 天津药物研究院 | 五元芳杂环甲苯基葡萄糖苷、其制备方法和用途 |
| SG173619A1 (en) | 2009-02-13 | 2011-09-29 | Boehringer Ingelheim Int | Pharmaceutical composition comprising a sglt2 inhibitor, a dpp-iv inhibitor and optionally a further antidiabetic agent and uses thereof |
| US20110009347A1 (en) | 2009-07-08 | 2011-01-13 | Yin Liang | Combination therapy for the treatment of diabetes |
| JP5658751B2 (ja) | 2009-07-10 | 2015-01-28 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプＪａｎｓｓｅｎ Ｐｈａｒｍａｃｅｕｔｉｃａ Ｎａａｍｌｏｚｅ Ｖｅｎｎｏｏｔｓｃｈａｐ | １−（β−Ｄ−グルコピラノシル）−４−メチル−３−［５−（４−フルオロフェニル）−２−チエニルメチル］ベンゼンのための結晶化方法 |
| WO2011039108A2 (en) | 2009-09-30 | 2011-04-07 | Boehringer Ingelheim International Gmbh | Processes for preparing of glucopyranosyl-substituted benzyl-benzene derivatives |
| EA020798B1 (ru) | 2009-09-30 | 2015-01-30 | Бёрингер Ингельхайм Интернациональ Гмбх | СПОСОБ ПОЛУЧЕНИЯ КРИСТАЛЛИЧЕСКОЙ ФОРМЫ 1-ХЛОР-4-(β-D-ГЛЮКОПИРАНОЗ-1-ИЛ)-2-[4-((S)-ТЕТРАГИДРОФУРАН-3-ИЛОКСИ)БЕНЗИЛ]БЕНЗОЛА |
| US10610489B2 (en) | 2009-10-02 | 2020-04-07 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition, pharmaceutical dosage form, process for their preparation, methods for treating and uses thereof |
| PL2488515T3 (pl) * | 2009-10-14 | 2017-07-31 | Janssen Pharmaceutica Nv | Sposób wytwarzania związków użytecznych jako inhibitory sglt2 |
| US8163704B2 (en) | 2009-10-20 | 2012-04-24 | Novartis Ag | Glycoside derivatives and uses thereof |
| BR112012008924A2 (pt) | 2009-10-20 | 2019-09-24 | Novartis Ag | derivado de glicosídeo e usos do mesmo |
| EA021983B1 (ru) | 2009-11-02 | 2015-10-30 | Пфайзер Инк. | Производные диоксабицикло[3.2.1]октан-2,3,4-триола |
| WO2011070592A2 (en) | 2009-12-09 | 2011-06-16 | Panacea Biotec Ltd. | Novel sugar derivatives |
| WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| LT2568988T (lt) | 2010-05-11 | 2016-09-12 | Janssen Pharmaceutica, N.V. | Farmacinės kompozicijos, apimančios 1-(beta-d-gliukopiranozil)-2-tienilmetilbenzeno darinius kaip sglt inhibitorius |
| WO2011153712A1 (en) | 2010-06-12 | 2011-12-15 | Theracos, Inc. | Crystalline form of benzylbenzene sglt2 inhibitor |
| KR101466838B1 (ko) | 2010-06-18 | 2014-11-28 | 주식회사 녹십자 | Sglt2 억제제로서의 티아졸 유도체 및 이를 포함하는 약학 조성물 |
| WO2012025857A1 (en) | 2010-08-23 | 2012-03-01 | Hetero Research Foundation | Cycloalkyl methoxybenzyl phenyl pyran derivatives as sodium dependent glucose co transporter (sglt2) inhibitors |
| US8921328B2 (en) | 2010-09-14 | 2014-12-30 | Glycomimetics, Inc. | E-selectin antagonists |
| UY33937A (es) | 2011-03-07 | 2012-09-28 | Boehringer Ingelheim Int | Composiciones farmacéuticas que contienen inhibidores de dpp-4 y/o sglt-2 y metformina |
| KR101913587B1 (ko) | 2011-04-13 | 2018-10-31 | 얀센 파마슈티카 엔.브이. | Sglt2의 억제제로서 유용한 화합물의 제조 방법 |
| WO2012140596A1 (en) | 2011-04-14 | 2012-10-18 | Novartis Ag | Glycoside derivatives and uses thereof |
| US8614195B2 (en) | 2011-04-14 | 2013-12-24 | Novartis Ag | Glycoside derivatives and uses thereof |
| TWI542596B (zh) | 2011-05-09 | 2016-07-21 | 健生藥品公司 | （２ｓ,３ｒ,４ｒ,５ｓ,６ｒ）－２－（３－（（５－（４－氟苯基）噻吩－２－基）甲基）－４－甲基苯基）－６－（羥甲基）四氫－２ｈ－哌喃－３,４,５－三醇之ｌ－脯胺酸及檸檬酸共晶體 |
| ES2655443T7 (es) | 2011-12-22 | 2021-03-22 | Glycomimetics Inc | Compuestos antagonistas de E-selectina |
| US9555001B2 (en) | 2012-03-07 | 2017-01-31 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition and uses thereof |
| US9192617B2 (en) | 2012-03-20 | 2015-11-24 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition, methods for treating and uses thereof |
| US9193751B2 (en) | 2012-04-10 | 2015-11-24 | Theracos, Inc. | Process for the preparation of benzylbenzene SGLT2 inhibitors |
| LT2928476T (lt) | 2012-12-07 | 2018-05-25 | Glycomimetics, Inc. | Junginiai, kompozicijos ir būdai, naudojant e-selektino antagonistus, hemopoetinių ląstelių mobilizacijai |
| EP2774619B1 (de) | 2013-03-04 | 2016-05-18 | BioActive Food GmbH | Zusammensetzung zur Behandlung von hyperglykämischen Erkrankungen |
| CN103127513A (zh) * | 2013-03-11 | 2013-06-05 | 乔文龙 | 一种治疗糖尿病及并发症的α-糖苷酶抑制剂和羟甲基戊二酰辅酶A还原酶抑制剂组合物 |
| US8652527B1 (en) | 2013-03-13 | 2014-02-18 | Upsher-Smith Laboratories, Inc | Extended-release topiramate capsules |
| ES2969245T3 (es) | 2013-03-14 | 2024-05-17 | Msd Int Gmbh | Formas cristalinas y métodos para preparar inhibidores de SGLT2 |
| US9101545B2 (en) | 2013-03-15 | 2015-08-11 | Upsher-Smith Laboratories, Inc. | Extended-release topiramate capsules |
| US11813275B2 (en) | 2013-04-05 | 2023-11-14 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition, methods for treating and uses thereof |
| CA2812519A1 (en) | 2013-04-05 | 2014-10-05 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition, methods for treating and uses thereof |
| PT2981271T (pt) | 2013-04-05 | 2019-02-19 | Boehringer Ingelheim Int | Utilizações terapêuticas de empagliflozina |
| HK1213818A1 (zh) | 2013-04-05 | 2016-07-15 | 勃林格殷格翰国际有限公司 | 依帕列净的治疗用途 |
| SI2986304T1 (sl) | 2013-04-18 | 2022-04-29 | Boehringer Ingelheim International Gmbh | Farmacevtski sestavek, postopki za zdravljenje in njegove uporabe |
| CN105611920B (zh) | 2013-10-12 | 2021-07-16 | 泰拉科斯萨普有限责任公司 | 羟基-二苯甲烷衍生物的制备 |
| EA201891406A1 (ru) | 2014-01-23 | 2018-12-28 | Бёрингер Ингельхайм Ветмедика Гмбх | Лечение метаболических расстройств у представителей собачьих |
| CN105001213B (zh) * | 2014-04-14 | 2020-08-28 | 上海迪诺医药科技有限公司 | C-芳基糖苷衍生物、其药物组合物、制备方法及应用 |
| EP2944311A1 (de) | 2014-05-16 | 2015-11-18 | BioActive Food GmbH | Kombination von biologisch aktiven Substanzen zur Behandlung von hyperglykämischen Erkrankungen |
| ES2754549T3 (es) | 2014-12-03 | 2020-04-20 | Glycomimetics Inc | Inhibidores heterobifuncionales de E-selectinas y receptores de quimioquinas CXCR4 |
| CN104478967A (zh) * | 2015-01-14 | 2015-04-01 | 佛山市赛维斯医药科技有限公司 | 含腈基苯噻唑基的o-半乳糖苷衍生物、其制备方法和用途 |
| CN104497068A (zh) * | 2015-01-15 | 2015-04-08 | 佛山市赛维斯医药科技有限公司 | 一种含三氟甲氧基苯s-葡萄糖苷结构的化合物及其用途 |
| CN104497073A (zh) * | 2015-01-15 | 2015-04-08 | 佛山市赛维斯医药科技有限公司 | 含丙烯腈和烷氧苯基o-葡萄糖苷结构的衍生物和用途 |
| CN104497074A (zh) * | 2015-01-15 | 2015-04-08 | 佛山市赛维斯医药科技有限公司 | 一种含丙烯腈基和硝基苯o-葡萄糖苷结构化合物及用途 |
| CN104497072A (zh) * | 2015-01-15 | 2015-04-08 | 佛山市赛维斯医药科技有限公司 | 含丙烯腈和卤代苯o-葡萄糖苷结构衍生物、其制备方法和用途 |
| CN104497069A (zh) * | 2015-01-15 | 2015-04-08 | 佛山市赛维斯医药科技有限公司 | 一类胺基苯基s-葡萄糖苷衍生物、其制备方法和用途 |
| CN104478961A (zh) * | 2015-01-15 | 2015-04-01 | 佛山市赛维斯医药科技有限公司 | 含丙烯腈和胺基苯o-葡萄糖苷结构衍生物、其制备方法和用途 |
| CN104497071A (zh) * | 2015-01-15 | 2015-04-08 | 佛山市赛维斯医药科技有限公司 | 一种含丙烯腈基和腈基苯o-葡萄糖苷结构化合物及用途 |
| US20170071970A1 (en) | 2015-09-15 | 2017-03-16 | Janssen Pharmaceutica Nv | Co-therapy comprising canagliflozin and phentermine for the treatment of obesity and obesity related disorders |
| US11045485B2 (en) | 2016-01-22 | 2021-06-29 | Glycomimetics, Inc. | Glycomimetic inhibitors of PA-IL and PA-IIL lectins |
| WO2017151708A1 (en) | 2016-03-02 | 2017-09-08 | Glycomimetics, Inc. | Methods for the treatment and/or prevention of cardiovescular disease by inhibition of e-selectin |
| WO2018031445A1 (en) | 2016-08-08 | 2018-02-15 | Glycomimetics, Inc. | Combination of t-cell checkpoint inhibitors with inhibitors of e-selectin or cxcr4, or with heterobifunctional inhibitors of both e-selectin and cxcr4 |
| KR20240046288A (ko) | 2016-10-07 | 2024-04-08 | 글리코미메틱스, 인크. | 매우 강력한 다량체성 e-셀렉틴 길항물질 |
| CN109922813A (zh) | 2016-11-10 | 2019-06-21 | 勃林格殷格翰国际有限公司 | 药物组合物、治疗方法及其用途 |
| US11197877B2 (en) | 2017-03-15 | 2021-12-14 | Glycomimetics. Inc. | Galactopyranosyl-cyclohexyl derivauves as E-selectin antagonists |
| US11712446B2 (en) | 2017-11-30 | 2023-08-01 | Glycomimetics, Inc. | Methods of mobilizing marrow infiltrating lymphocytes and uses thereof |
| US11548908B2 (en) | 2017-12-29 | 2023-01-10 | Glycomimetics, Inc. | Heterobifunctional inhibitors of E-selectin and galectin-3 |
| BR112020018184A2 (pt) | 2018-03-05 | 2021-02-02 | Glycomimetics, Inc. | usos de compostos |
| US11495339B2 (en) * | 2018-06-14 | 2022-11-08 | Astrazeneca Uk Limited | Methods for lowering blood sugar with a gliflozin sodium-glucose cotransport 2 inhibitor pharmaceutical composition |
| MA53175A (fr) | 2018-07-19 | 2021-05-26 | Astrazeneca Ab | Méthodes de traitement de hfpef au moyen de dapagliflozine et compositions comprenant celle-ci |
| CN109456370A (zh) * | 2018-12-24 | 2019-03-12 | 重庆理工大学 | 一种钠-葡萄糖协同转运蛋白2抑制剂及其应用 |
| US11845771B2 (en) | 2018-12-27 | 2023-12-19 | Glycomimetics, Inc. | Heterobifunctional inhibitors of E-selectin and galectin-3 |
| CN113801179B (zh) * | 2020-06-11 | 2025-10-31 | 华东理工大学 | 一类β-半乳糖苷酶荧光探针、制备方法及其应用 |
| PT4188389T (pt) | 2020-07-27 | 2025-10-07 | Astrazeneca Ab | Dapagliflozina para utilização em métodos de tratamento de doença renal crónica |
| EP4315350A1 (en) | 2021-04-01 | 2024-02-07 | AstraZeneca UK Limited | Systems and methods for managing prediabetes with a gliflozin sodium-glucose cotransport 2 inhibitor pharmaceutical composition |
| CN113980071B (zh) * | 2021-11-26 | 2023-08-22 | 重庆大学 | 红景天苷衍生物及其应用 |
| EP4469038A1 (en) | 2022-01-26 | 2024-12-04 | Astrazeneca AB | Dapagliflozin for use in the treatment of prediabetes or reducing the risk of developing type 2 diabetes |
| CN114933619B (zh) * | 2022-05-18 | 2024-03-01 | 上海科利生物医药有限公司 | 一类硫代糖苷列净类似物及其制备方法和应用 |
| WO2024033288A1 (en) * | 2022-08-12 | 2024-02-15 | Société des Produits Nestlé S.A. | Salicin derivatives as inhibitors of sglt2 |
| WO2025125513A1 (en) | 2023-12-15 | 2025-06-19 | AstraZeneca Ireland Limited | Sglt2 inhibitors and baxdrostat for treating chronic kidney disease and hypertension |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61233621A (ja) * | 1985-04-10 | 1986-10-17 | Agency Of Ind Science & Technol | 肥満細胞脱顆粒抑制剤 |
| EP0524439A1 (en) * | 1991-07-24 | 1993-01-27 | F.Hoffmann-La Roche & Co. Aktiengesellschaft | Novel cyclohexane and tetrahydropyran derivatives and antifungal compositions containing these derivatives |
| CA2102591C (en) | 1992-11-12 | 2000-12-26 | Kenji Tsujihara | Hypoglycemic agent |
| US5444050A (en) * | 1994-04-29 | 1995-08-22 | Texas Biotechnology Corporation | Binding of E-selectin or P-selectin to sialyl Lewisx or sialyl-Lewisa |
| US5830873A (en) | 1994-05-11 | 1998-11-03 | Tanabe Seiyaku Co., Ltd. | Propiophenone derivative and a process for preparing the same |
| JP2814950B2 (ja) | 1994-05-11 | 1998-10-27 | 田辺製薬株式会社 | 血糖降下剤 |
| FI974618L (fi) | 1995-06-29 | 1997-12-23 | Texas Biotechnology Corp | Kahden- ja kolmenarvoiset pienimolekyyliset selektiininestäjät |
| JP3034192B2 (ja) | 1995-11-07 | 2000-04-17 | 田辺製薬株式会社 | プロピオフェノン誘導体およびその製法 |
| JP3059088B2 (ja) | 1995-11-07 | 2000-07-04 | 田辺製薬株式会社 | プロピオフェノン誘導体およびその製法 |
| JP3006513B2 (ja) | 1995-11-07 | 2000-02-07 | 田辺製薬株式会社 | 医薬組成物 |
| JP3065235B2 (ja) | 1995-11-07 | 2000-07-17 | 田辺製薬株式会社 | プロピオフェノン誘導体およびその製法 |
| DE19615576A1 (de) * | 1996-04-19 | 1997-10-23 | Beiersdorf Ag | Verfahren zur Herstellung von Mono- und/oder Diglucosiden des Glabridins und deren Verwendung als antiirritativer Wirkstoff in kosmetischen und topischen dermatologischen Zubereitungen |
| PT850948E (pt) | 1996-12-26 | 2002-08-30 | Tanabe Seiyaku Co | Derivados propiofenona e processo para a preparacao dos mesmos |
| WO1998031697A1 (en) | 1997-01-15 | 1998-07-23 | Sankyo Company, Limited | Aryl c-glycoside compounds and sulfated esters thereof |
| JPH10245391A (ja) | 1997-03-03 | 1998-09-14 | Dainippon Ink & Chem Inc | ７−グリコシロキシベンゾピラン誘導体を有効成分とする糖尿病治療剤 |
| WO1999031036A2 (en) | 1997-12-12 | 1999-06-24 | Ciba Specialty Chemicals Holding Inc. | O-derivatives of halogenated diphenyl ether compounds |
| US6486299B1 (en) | 1998-09-28 | 2002-11-26 | Curagen Corporation | Genes and proteins predictive and therapeutic for stroke, hypertension, diabetes and obesity |
| US6069238A (en) | 1998-09-30 | 2000-05-30 | Eli Lilly And Company | Spirocyclic C-glycosides |
| BR0109323A (pt) * | 2000-03-17 | 2002-12-24 | Kissei Pharmaceutical | Derivados de gluco piranosiloxi benzil benzeno, composições medicinais contendo os mesmos e intermediários para a preparação dos derivados |
-
2001
- 2001-02-23 US US09/791,512 patent/US6683056B2/en not_active Expired - Lifetime
- 2001-03-29 CA CA002404373A patent/CA2404373A1/en not_active Abandoned
- 2001-03-29 MX MXPA02009522A patent/MXPA02009522A/es active IP Right Grant
- 2001-03-29 WO PCT/US2001/010092 patent/WO2001074834A1/en not_active Ceased
- 2001-03-29 AT AT01922840T patent/ATE316976T1/de active
- 2001-03-29 RU RU2002126586/04A patent/RU2269540C2/ru not_active IP Right Cessation
- 2001-03-29 BR BR0109326-6A patent/BR0109326A/pt not_active IP Right Cessation
- 2001-03-29 ES ES01922840T patent/ES2258079T3/es not_active Expired - Lifetime
- 2001-03-29 CN CNB01807538XA patent/CN1275977C/zh not_active Expired - Fee Related
- 2001-03-29 IL IL15147301A patent/IL151473A0/xx unknown
- 2001-03-29 JP JP2001572523A patent/JP4986202B2/ja not_active Expired - Fee Related
- 2001-03-29 AU AU4959801A patent/AU4959801A/xx active Pending
- 2001-03-29 PL PL01365176A patent/PL365176A1/xx unknown
- 2001-03-29 AU AU2001249598A patent/AU2001249598B2/en not_active Ceased
- 2001-03-29 EP EP01922840A patent/EP1268502B1/en not_active Expired - Lifetime
- 2001-03-29 HU HU0301513A patent/HUP0301513A3/hu unknown
- 2001-03-29 DE DE60117012T patent/DE60117012T2/de not_active Expired - Lifetime
- 2001-03-29 KR KR1020027012976A patent/KR100798203B1/ko not_active Expired - Fee Related
- 2001-03-29 NZ NZ520822A patent/NZ520822A/en unknown
-
2002
- 2002-09-02 ZA ZA200207030A patent/ZA200207030B/en unknown
- 2002-09-27 NO NO20024642A patent/NO20024642L/no unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2004500416A5 (OSRAM) | ||
| RU2002126586A (ru) | О-арилглюкозидные ингибиторы sglt2 и способ их применения | |
| CA2402894A1 (en) | Cyclopropyl-fused pyrrolidine-based inhibitors of dipeptidyl peptidase iv and method | |
| ME00091B (me) | C-aril glukozid sglt2 inhibitori i postupak za njihovu upotrebu | |
| JP5435841B2 (ja) | 複素環式ボロン酸化合物 | |
| RU2002109477A (ru) | С-арилглюкозидные ингибиторы SGTL2 | |
| CN100540001C (zh) | 包含止泻药和埃坡霉素或埃坡霉素衍生物的组合 | |
| RU2291858C2 (ru) | Замещенные амидом карбоновой кислоты производные фенилмочевины и их применение в качестве лекарственных средств | |
| JP2010077163A5 (OSRAM) | ||
| CA2366871A1 (en) | Heterocyclic containing biphenyl ap2 inhibitors and method | |
| EP2078015B1 (en) | Modulators of glucocorticoid receptor, ap-1 and/or nf-kappab activity and use thereof | |
| JP2006501187A5 (OSRAM) | ||
| CA2024572A1 (en) | N-substituted-4-pyrimidinamines and-pyrimidinediamines, a process for their preparation and their use as medicaments | |
| JP2007512254A5 (OSRAM) | ||
| CA2471262A1 (en) | Pyrido(2,1-a)isoquinoline derivatives as dpp-iv inhibitors | |
| CA2410237A1 (en) | Adenosine a2a receptor antagonists | |
| JP2004536115A5 (OSRAM) | ||
| JP2008517921A5 (OSRAM) | ||
| JP2007501231A5 (OSRAM) | ||
| JP2004523561A5 (OSRAM) | ||
| RU2002111867A (ru) | Гетероциклические ингибиторы натрий/протонового обмена | |
| JP2004536070A5 (OSRAM) | ||
| ES2214168T1 (es) | Derivados de acidos de azol sustituidos utiles como agentes antidiabeticos y contra la obesidad y procedimiento. | |
| WO2010107809A2 (en) | Methods for preparing dpp-iv inhibitor compounds | |
| CN1894261B (zh) | 杂环硼酸化合物 |