JP2009537524A5 - - Google Patents
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- Publication number
- JP2009537524A5 JP2009537524A5 JP2009510986A JP2009510986A JP2009537524A5 JP 2009537524 A5 JP2009537524 A5 JP 2009537524A5 JP 2009510986 A JP2009510986 A JP 2009510986A JP 2009510986 A JP2009510986 A JP 2009510986A JP 2009537524 A5 JP2009537524 A5 JP 2009537524A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- group
- substituted
- independently selected
- halogen
- 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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- 125000000217 alkyl group Chemical group 0.000 claims 99
- 229910052736 halogen Inorganic materials 0.000 claims 54
- 150000002367 halogens Chemical class 0.000 claims 52
- 229910052739 hydrogen Inorganic materials 0.000 claims 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 17
- 150000001875 compounds Chemical class 0.000 claims 16
- 150000003839 salts Chemical class 0.000 claims 15
- 229910052760 oxygen Inorganic materials 0.000 claims 11
- 229910052717 sulfur Inorganic materials 0.000 claims 11
- 229910052799 carbon Inorganic materials 0.000 claims 10
- 125000005842 heteroatom Chemical group 0.000 claims 10
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 8
- -1 phenoxy, benzyl Chemical group 0.000 claims 8
- 125000001424 substituent group Chemical group 0.000 claims 8
- 150000004292 cyclic ethers Chemical class 0.000 claims 7
- 125000003118 aryl group Chemical group 0.000 claims 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims 5
- 125000000623 heterocyclic group Chemical group 0.000 claims 5
- 239000003112 inhibitor Substances 0.000 claims 5
- 125000001624 naphthyl group Chemical group 0.000 claims 5
- 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
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 4
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 3
- 239000003937 drug carrier Substances 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- 125000001766 1,2,4-oxadiazol-3-yl group Chemical group [H]C1=NC(*)=NO1 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- 102000016622 Dipeptidyl Peptidase 4 Human genes 0.000 claims 2
- 101000930822 Giardia intestinalis Dipeptidyl-peptidase 4 Proteins 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
- 102000004877 Insulin Human genes 0.000 claims 2
- 108090001061 Insulin Proteins 0.000 claims 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims 2
- 102000002072 Non-Receptor Type 1 Protein Tyrosine Phosphatase Human genes 0.000 claims 2
- 108010015847 Non-Receptor Type 1 Protein Tyrosine Phosphatase Proteins 0.000 claims 2
- 102000023984 PPAR alpha Human genes 0.000 claims 2
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims 2
- 239000000556 agonist Substances 0.000 claims 2
- 210000000941 bile Anatomy 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 229940125396 insulin Drugs 0.000 claims 2
- 125000002950 monocyclic group Chemical group 0.000 claims 2
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 claims 2
- 108091008725 peroxisome proliferator-activated receptors alpha Proteins 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 2
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims 1
- 229940077274 Alpha glucosidase inhibitor Drugs 0.000 claims 1
- 229940123208 Biguanide Drugs 0.000 claims 1
- XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 claims 1
- 101001078593 Caenorhabditis elegans 3beta-hydroxysteroid dehydrogenase/Delta(5)-Delta(4) isomerase 1 Proteins 0.000 claims 1
- 108010078791 Carrier Proteins Proteins 0.000 claims 1
- 229940122502 Cholesterol absorption inhibitor Drugs 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 101710198884 GATA-type zinc finger protein 1 Proteins 0.000 claims 1
- 229940123232 Glucagon receptor agonist Drugs 0.000 claims 1
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims 1
- 101000618112 Homo sapiens Sperm-associated antigen 8 Proteins 0.000 claims 1
- 108010016731 PPAR gamma Proteins 0.000 claims 1
- 102000000536 PPAR gamma Human genes 0.000 claims 1
- 229940122054 Peroxisome proliferator-activated receptor delta agonist Drugs 0.000 claims 1
- 102100040918 Pro-glucagon Human genes 0.000 claims 1
- 102100021913 Sperm-associated antigen 8 Human genes 0.000 claims 1
- 102000001494 Sterol O-Acyltransferase Human genes 0.000 claims 1
- 108010054082 Sterol O-acyltransferase Proteins 0.000 claims 1
- 229940100389 Sulfonylurea Drugs 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 239000003888 alpha glucosidase inhibitor Substances 0.000 claims 1
- 239000002260 anti-inflammatory agent Substances 0.000 claims 1
- 229940121363 anti-inflammatory agent Drugs 0.000 claims 1
- 230000003579 anti-obesity Effects 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000003354 cholesterol ester transfer protein inhibitor Substances 0.000 claims 1
- 229940125881 cholesteryl ester transfer protein inhibitor Drugs 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229940125542 dual agonist Drugs 0.000 claims 1
- 150000002170 ethers Chemical group 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims 1
- 150000002632 lipids Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229960002715 nicotine Drugs 0.000 claims 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims 1
- 229960003512 nicotinic acid Drugs 0.000 claims 1
- 235000001968 nicotinic acid Nutrition 0.000 claims 1
- 239000011664 nicotinic acid Substances 0.000 claims 1
- 239000004031 partial agonist Substances 0.000 claims 1
- 239000002530 phenolic antioxidant Substances 0.000 claims 1
- 125000005493 quinolyl group Chemical group 0.000 claims 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 claims 1
- 0 C*c1ccc(C2(*)C(*)(*3)C2(*)*)c3c1 Chemical compound C*c1ccc(C2(*)C(*)(*3)C2(*)*)c3c1 0.000 description 18
- QYKBWEDDHYYSKJ-BZUAXINKSA-N COc(cc(C(F)(F)F)cc1)c1Oc1ccc([C@H]([C@H]2C(O)=O)[C@H]2O2)c2c1 Chemical compound COc(cc(C(F)(F)F)cc1)c1Oc1ccc([C@H]([C@H]2C(O)=O)[C@H]2O2)c2c1 QYKBWEDDHYYSKJ-BZUAXINKSA-N 0.000 description 2
- YPJVPNXMYDTNAI-UHFFFAOYSA-N Cc(cc(C(F)(F)F)cc1)c1Oc1cc(OC2C3C2C(O)=O)c3cc1 Chemical compound Cc(cc(C(F)(F)F)cc1)c1Oc1cc(OC2C3C2C(O)=O)c3cc1 YPJVPNXMYDTNAI-UHFFFAOYSA-N 0.000 description 2
- CELNRZMSPVXGBI-BRWVUGGUSA-N Cc(cc(cc1)C#N)c1Oc1ccc([C@H]([C@H]2C(O)=O)[C@H]2O2)c2c1 Chemical compound Cc(cc(cc1)C#N)c1Oc1ccc([C@H]([C@H]2C(O)=O)[C@H]2O2)c2c1 CELNRZMSPVXGBI-BRWVUGGUSA-N 0.000 description 2
- LUOBBBRZVISPTB-RBSFLKMASA-N OC([C@H]1[C@@H]2Oc3cc(Oc(ccc(C(F)(F)F)c4)c4Cl)ccc3[C@H]12)=O Chemical compound OC([C@H]1[C@@H]2Oc3cc(Oc(ccc(C(F)(F)F)c4)c4Cl)ccc3[C@H]12)=O LUOBBBRZVISPTB-RBSFLKMASA-N 0.000 description 2
- GZQUHARXXKGXOU-GUDVDZBRSA-N OC([C@H]1[C@@H]2Oc3cc(Oc4c(cccc5)c5c(C(F)(F)F)cc4)ccc3[C@H]12)=O Chemical compound OC([C@H]1[C@@H]2Oc3cc(Oc4c(cccc5)c5c(C(F)(F)F)cc4)ccc3[C@H]12)=O GZQUHARXXKGXOU-GUDVDZBRSA-N 0.000 description 2
- QWYXACFTAOUEKR-MUAWNBEISA-N CC(C(C(C)=C1)c2cc(COc3ccc([C@H]([C@H]4C(O)=O)[C@H]4O4)c4c3)ccc2)C=C1OC1OCCCC1 Chemical compound CC(C(C(C)=C1)c2cc(COc3ccc([C@H]([C@H]4C(O)=O)[C@H]4O4)c4c3)ccc2)C=C1OC1OCCCC1 QWYXACFTAOUEKR-MUAWNBEISA-N 0.000 description 1
- MPIBQZHTDRBCBF-OMSMZCRRSA-N CC(c1cc(C(F)(F)F)ccc1)Oc1ccc([C@H]([C@H]2C(O)=O)[C@H]2O2)c2c1 Chemical compound CC(c1cc(C(F)(F)F)ccc1)Oc1ccc([C@H]([C@H]2C(O)=O)[C@H]2O2)c2c1 MPIBQZHTDRBCBF-OMSMZCRRSA-N 0.000 description 1
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2007
- 2007-05-11 AU AU2007254325A patent/AU2007254325B2/en not_active Ceased
- 2007-05-11 WO PCT/US2007/011369 patent/WO2007136572A2/en not_active Ceased
- 2007-05-11 WO PCT/US2007/011372 patent/WO2007136573A2/en not_active Ceased
- 2007-05-11 PE PE2007000575A patent/PE20080069A1/es not_active Application Discontinuation
- 2007-05-11 CA CA2651153A patent/CA2651153C/en not_active Expired - Fee Related
- 2007-05-11 US US11/801,841 patent/US7442808B2/en active Active
- 2007-05-11 JP JP2009510986A patent/JP5271895B2/ja not_active Expired - Fee Related
- 2007-05-11 AT AT07794762T patent/ATE552245T1/de active
- 2007-05-11 EP EP07794762A patent/EP2021327B1/en active Active
- 2007-05-14 AR ARP070102069A patent/AR060916A1/es not_active Application Discontinuation
- 2007-05-14 DO DO2007000099A patent/DOP2007000099A/es unknown
- 2007-05-14 TW TW096117055A patent/TW200812992A/zh unknown
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