JP2015525782A5 - - Google Patents

Info

Publication number

JP2015525782A5

JP2015525782A5 JP2015525549A JP2015525549A JP2015525782A5 JP 2015525782 A5 JP2015525782 A5 JP 2015525782A5 JP 2015525549 A JP2015525549 A JP 2015525549A JP 2015525549 A JP2015525549 A JP 2015525549A JP 2015525782 A5 JP2015525782 A5 JP 2015525782A5

Authority

JP

Japan

Prior art keywords

alkyl

group

pharmaceutically acceptable

halogen

unsubstituted

Prior art date

2013-07-31

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.)

Withdrawn

Links

• Espacenet
• Global Dossier
• Discuss

• 125000000217 alkyl group Chemical group 0.000 claims 64
• 150000001875 compounds Chemical class 0.000 claims 21
• 150000003839 salts Chemical class 0.000 claims 20
• 229910052736 halogen Inorganic materials 0.000 claims 19
• 150000002367 halogens Chemical class 0.000 claims 19
• 125000001424 substituent group Chemical group 0.000 claims 17
• 125000004093 cyano group Chemical group *C#N 0.000 claims 13
• 229910052739 hydrogen Inorganic materials 0.000 claims 7
• 239000001257 hydrogen Substances 0.000 claims 7
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 6
• 239000008194 pharmaceutical composition Substances 0.000 claims 6
• 125000003118 aryl group Chemical group 0.000 claims 5
• 125000001072 heteroaryl group Chemical group 0.000 claims 5
• 239000003112 inhibitor Substances 0.000 claims 5
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 4
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 4
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
• 239000003814 drug Substances 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
• 229910052760 oxygen Inorganic materials 0.000 claims 4
• 239000001301 oxygen Substances 0.000 claims 4
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 3
• 102000016622 Dipeptidyl Peptidase 4 Human genes 0.000 claims 2
• 102100026148 Free fatty acid receptor 1 Human genes 0.000 claims 2
• 101710142060 Free fatty acid receptor 1 Proteins 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
• 230000008484 agonism Effects 0.000 claims 2
• IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims 2
• 201000010099 disease Diseases 0.000 claims 2
• 229940079593 drug Drugs 0.000 claims 2
• 239000003937 drug carrier Substances 0.000 claims 2
• 229940125396 insulin Drugs 0.000 claims 2
• 108091008725 peroxisome proliferator-activated receptors alpha Proteins 0.000 claims 2
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 2
• KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 claims 1
• BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims 1
• HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims 1
• MVQVNTPHUGQQHK-UHFFFAOYSA-N 3-pyridinemethanol Chemical compound OCC1=CC=CN=C1 MVQVNTPHUGQQHK-UHFFFAOYSA-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
• 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 1
• 101001078593 Caenorhabditis elegans 3beta-hydroxysteroid dehydrogenase/Delta(5)-Delta(4) isomerase 1 Proteins 0.000 claims 1
• 229940122502 Cholesterol absorption inhibitor Drugs 0.000 claims 1
• 101710198884 GATA-type zinc finger protein 1 Proteins 0.000 claims 1
• 229940122904 Glucagon receptor antagonist 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
• 241000124008 Mammalia Species 0.000 claims 1
• 229940110346 PPAR gamma partial agonist Drugs 0.000 claims 1
• 229940122054 Peroxisome proliferator-activated receptor delta agonist Drugs 0.000 claims 1
• 229940080774 Peroxisome proliferator-activated receptor gamma agonist Drugs 0.000 claims 1
• 102100040918 Pro-glucagon Human genes 0.000 claims 1
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 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 claims 1
• 108091006277 SLC5A1 Proteins 0.000 claims 1
• 102000058090 Sodium-Glucose Transporter 1 Human genes 0.000 claims 1
• 229940123518 Sodium/glucose cotransporter 2 inhibitor Drugs 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
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 1
• 125000002252 acyl group Chemical group 0.000 claims 1
• 239000000556 agonist Substances 0.000 claims 1
• 125000003342 alkenyl 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
• 229940124599 anti-inflammatory drug Drugs 0.000 claims 1
• 230000003579 anti-obesity Effects 0.000 claims 1
• 125000004429 atom Chemical group 0.000 claims 1
• 229920000080 bile acid sequestrant Polymers 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
• 229940125542 dual agonist Drugs 0.000 claims 1
• OLNTVTPDXPETLC-XPWALMASSA-N ezetimibe Chemical compound N1([C@@H]([C@H](C1=O)CC[C@H](O)C=1C=CC(F)=CC=1)C=1C=CC(O)=CC=1)C1=CC=C(F)C=C1 OLNTVTPDXPETLC-XPWALMASSA-N 0.000 claims 1
• 229960000815 ezetimibe Drugs 0.000 claims 1
• 235000019000 fluorine Nutrition 0.000 claims 1
• 125000001153 fluoro group Chemical group F* 0.000 claims 1
• 125000005842 heteroatom Chemical group 0.000 claims 1
• 150000002431 hydrogen Chemical class 0.000 claims 1
• 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims 1
• 229940121380 ileal bile acid transporter inhibitor Drugs 0.000 claims 1
• 150000002632 lipids Chemical class 0.000 claims 1
• 238000004519 manufacturing process Methods 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
• 229960004738 nicotinyl alcohol Drugs 0.000 claims 1
• 239000004031 partial agonist Substances 0.000 claims 1
• 239000002530 phenolic antioxidant Substances 0.000 claims 1
• 230000002265 prevention Effects 0.000 claims 1
• 229960002855 simvastatin Drugs 0.000 claims 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 claims 1
• MFFMDFFZMYYVKS-SECBINFHSA-N sitagliptin Chemical compound C([C@H](CC(=O)N1CC=2N(C(=NN=2)C(F)(F)F)CC1)N)C1=CC(F)=C(F)C=C1F MFFMDFFZMYYVKS-SECBINFHSA-N 0.000 claims 1
• 229960004034 sitagliptin Drugs 0.000 claims 1
• YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 claims 1
• 229910052717 sulfur Inorganic materials 0.000 claims 1
• 239000011593 sulfur Chemical group 0.000 claims 1
• 238000002560 therapeutic procedure Methods 0.000 claims 1