JP2006524709A5 - - Google Patents
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- JP2006524709A5 JP2006524709A5 JP2006513366A JP2006513366A JP2006524709A5 JP 2006524709 A5 JP2006524709 A5 JP 2006524709A5 JP 2006513366 A JP2006513366 A JP 2006513366A JP 2006513366 A JP2006513366 A JP 2006513366A JP 2006524709 A5 JP2006524709 A5 JP 2006524709A5
- Authority
- JP
- Japan
- Prior art keywords
- optionally
- alkyl
- optionally substituted
- inhibitor
- alkoxy
- 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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- 150000001875 compounds Chemical class 0.000 claims 22
- 125000002837 carbocyclic group Chemical group 0.000 claims 17
- 125000005843 halogen group Chemical group 0.000 claims 17
- 125000005842 heteroatom Chemical group 0.000 claims 16
- 239000003112 inhibitor Substances 0.000 claims 14
- 229910052760 oxygen Inorganic materials 0.000 claims 14
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 12
- 229910052717 sulfur Inorganic materials 0.000 claims 11
- 229920006395 saturated elastomer Polymers 0.000 claims 10
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 9
- 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 9
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 8
- 229910052799 carbon Inorganic materials 0.000 claims 8
- 239000003795 chemical substances by application Substances 0.000 claims 8
- 206010012601 diabetes mellitus Diseases 0.000 claims 8
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 7
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 7
- 239000003814 drug Substances 0.000 claims 7
- HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 claims 6
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims 6
- 239000003613 bile acid Substances 0.000 claims 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 6
- 125000002619 bicyclic group Chemical group 0.000 claims 5
- 125000000623 heterocyclic group Chemical group 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- 125000002950 monocyclic group Chemical group 0.000 claims 5
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 4
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 4
- -1 C 1 -C 6 alkoxy Chemical group 0.000 claims 4
- 208000002705 Glucose Intolerance Diseases 0.000 claims 4
- 239000000883 anti-obesity agent Substances 0.000 claims 4
- 229940125710 antiobesity agent Drugs 0.000 claims 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 4
- 125000004122 cyclic group Chemical group 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 229940079593 drug Drugs 0.000 claims 4
- 150000002148 esters Chemical class 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 201000009104 prediabetes syndrome Diseases 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 238000011282 treatment Methods 0.000 claims 4
- 229940124681 11 beta HSD inhibitor Drugs 0.000 claims 3
- 239000005541 ACE inhibitor Substances 0.000 claims 3
- 229940077274 Alpha glucosidase inhibitor Drugs 0.000 claims 3
- 229940123208 Biguanide Drugs 0.000 claims 3
- 229940127291 Calcium channel antagonist Drugs 0.000 claims 3
- 102000016622 Dipeptidyl Peptidase 4 Human genes 0.000 claims 3
- 101100379081 Emericella variicolor andC gene Proteins 0.000 claims 3
- 101000930822 Giardia intestinalis Dipeptidyl-peptidase 4 Proteins 0.000 claims 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims 3
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims 3
- 102000004877 Insulin Human genes 0.000 claims 3
- 108090001061 Insulin Proteins 0.000 claims 3
- 229940122199 Insulin secretagogue Drugs 0.000 claims 3
- 229940122355 Insulin sensitizer Drugs 0.000 claims 3
- 102000003729 Neprilysin Human genes 0.000 claims 3
- 108090000028 Neprilysin Proteins 0.000 claims 3
- 102000002072 Non-Receptor Type 1 Protein Tyrosine Phosphatase Human genes 0.000 claims 3
- 108010015847 Non-Receptor Type 1 Protein Tyrosine Phosphatase Proteins 0.000 claims 3
- 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 claims 3
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 claims 3
- 229940100389 Sulfonylurea Drugs 0.000 claims 3
- 239000003888 alpha glucosidase inhibitor Substances 0.000 claims 3
- 239000002333 angiotensin II receptor antagonist Substances 0.000 claims 3
- 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 claims 3
- 239000003524 antilipemic agent Substances 0.000 claims 3
- 239000002876 beta blocker Substances 0.000 claims 3
- 229940097320 beta blocking agent Drugs 0.000 claims 3
- 150000004283 biguanides Chemical class 0.000 claims 3
- 239000000480 calcium channel blocker Substances 0.000 claims 3
- 239000002934 diuretic Substances 0.000 claims 3
- 239000008103 glucose Substances 0.000 claims 3
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims 3
- 229940125396 insulin Drugs 0.000 claims 3
- 239000003446 ligand Substances 0.000 claims 3
- 230000003228 microsomal effect Effects 0.000 claims 3
- 239000011664 nicotinic acid Substances 0.000 claims 3
- 229960003512 nicotinic acid Drugs 0.000 claims 3
- 235000001968 nicotinic acid Nutrition 0.000 claims 3
- 150000002823 nitrates Chemical class 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 239000002516 radical scavenger Substances 0.000 claims 3
- 230000009103 reabsorption Effects 0.000 claims 3
- 239000002464 receptor antagonist Substances 0.000 claims 3
- 229940044551 receptor antagonist Drugs 0.000 claims 3
- 239000002461 renin inhibitor Substances 0.000 claims 3
- 229940086526 renin-inhibitors Drugs 0.000 claims 3
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 claims 3
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims 3
- ILPUOPPYSQEBNJ-UHFFFAOYSA-N 2-methyl-2-phenoxypropanoic acid Chemical class OC(=O)C(C)(C)OC1=CC=CC=C1 ILPUOPPYSQEBNJ-UHFFFAOYSA-N 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- 229940097420 Diuretic Drugs 0.000 claims 2
- 208000001145 Metabolic Syndrome Diseases 0.000 claims 2
- 239000000400 angiotensin II type 1 receptor blocker Substances 0.000 claims 2
- 230000001363 autoimmune Effects 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 230000001882 diuretic effect Effects 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 229940125753 fibrate Drugs 0.000 claims 2
- 208000004104 gestational diabetes Diseases 0.000 claims 2
- 210000004185 liver Anatomy 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 238000011321 prophylaxis Methods 0.000 claims 2
- 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 2
- 239000000126 substance Substances 0.000 claims 2
- ODNZGJDBOJGCIF-LJQANCHMSA-N (2r)-2-[5-[3-[4-(4-ethoxy-5-methyl-1,3-thiazol-2-yl)-2-propylphenoxy]propoxy]indol-1-yl]propanoic acid Chemical compound C=1C=C(OCCCOC=2C=C3C=CN(C3=CC=2)[C@H](C)C(O)=O)C(CCC)=CC=1C1=NC(OCC)=C(C)S1 ODNZGJDBOJGCIF-LJQANCHMSA-N 0.000 claims 1
- NZHCHGSBOJVZMG-NRFANRHFSA-N (2s)-2-[3-methyl-5-[3-[2-propyl-4-(4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)phenoxy]propoxy]indol-1-yl]propanoic acid Chemical compound C1CCCC(S2)=C1N=C2C1=CC=C(OCCCOC=2C=C3C(C)=CN(C3=CC=2)[C@@H](C)C(O)=O)C(CCC)=C1 NZHCHGSBOJVZMG-NRFANRHFSA-N 0.000 claims 1
- ODNZGJDBOJGCIF-IBGZPJMESA-N (2s)-2-[5-[3-[4-(4-ethoxy-5-methyl-1,3-thiazol-2-yl)-2-propylphenoxy]propoxy]indol-1-yl]propanoic acid Chemical compound C=1C=C(OCCCOC=2C=C3C=CN(C3=CC=2)[C@@H](C)C(O)=O)C(CCC)=CC=1C1=NC(OCC)=C(C)S1 ODNZGJDBOJGCIF-IBGZPJMESA-N 0.000 claims 1
- AATUKXAMWPBQCI-UHFFFAOYSA-N 2-[3-ethyl-5-[3-[2-propyl-4-(4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)phenoxy]propoxy]indol-1-yl]acetic acid Chemical compound C1CCCC(S2)=C1N=C2C1=CC=C(OCCCOC=2C=C3C(CC)=CN(CC(O)=O)C3=CC=2)C(CCC)=C1 AATUKXAMWPBQCI-UHFFFAOYSA-N 0.000 claims 1
- DNOSAZIJZXQJPY-UHFFFAOYSA-N 2-[3-methyl-5-[3-[2-propyl-4-(4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)phenoxy]propoxy]-1h-indol-2-yl]acetic acid Chemical compound C1CCCC(S2)=C1N=C2C1=CC=C(OCCCOC=2C=C3C(C)=C(CC(O)=O)NC3=CC=2)C(CCC)=C1 DNOSAZIJZXQJPY-UHFFFAOYSA-N 0.000 claims 1
- HPENJUSOGRHJOD-UHFFFAOYSA-N 2-[3-methyl-5-[3-[2-propyl-4-(4,5,6,7-tetrahydro-1,3-benzoxazol-2-yl)phenoxy]propoxy]-1h-indol-2-yl]propanoic acid Chemical compound C1CCCC(O2)=C1N=C2C1=CC=C(OCCCOC=2C=C3C(C)=C(C(C)C(O)=O)NC3=CC=2)C(CCC)=C1 HPENJUSOGRHJOD-UHFFFAOYSA-N 0.000 claims 1
- ZDFMZJPKRSPQKY-UHFFFAOYSA-N 2-[5-[3-[2-methoxy-4-(4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)phenoxy]propoxy]-1h-indol-2-yl]acetic acid Chemical compound C1CCCC(S2)=C1N=C2C1=CC=C(OCCCOC=2C=C3C=C(CC(O)=O)NC3=CC=2)C(OC)=C1 ZDFMZJPKRSPQKY-UHFFFAOYSA-N 0.000 claims 1
- XIYFJXWZEKSXDD-UHFFFAOYSA-N 2-[5-[3-[2-propyl-4-(1,3-thiazol-2-yl)phenoxy]propoxy]-1h-indol-2-yl]acetic acid Chemical compound C=1C=C(OCCCOC=2C=C3C=C(CC(O)=O)NC3=CC=2)C(CCC)=CC=1C1=NC=CS1 XIYFJXWZEKSXDD-UHFFFAOYSA-N 0.000 claims 1
- YRMNKMPRDAQXDC-UHFFFAOYSA-N 2-[5-[3-[2-propyl-4-(4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)phenoxy]propoxy]-1h-indol-2-yl]acetic acid Chemical compound C1CCCC(S2)=C1N=C2C1=CC=C(OCCCOC=2C=C3C=C(CC(O)=O)NC3=CC=2)C(CCC)=C1 YRMNKMPRDAQXDC-UHFFFAOYSA-N 0.000 claims 1
- NNCMAOPUOZJPQR-UHFFFAOYSA-N 2-[5-[3-[2-propyl-4-(4,5,6,7-tetrahydro-1,3-benzoxazol-2-yl)phenoxy]propoxy]indol-1-yl]acetic acid Chemical compound C1CCCC(O2)=C1N=C2C1=CC=C(OCCCOC=2C=C3C=CN(CC(O)=O)C3=CC=2)C(CCC)=C1 NNCMAOPUOZJPQR-UHFFFAOYSA-N 0.000 claims 1
- ZHLAZEYLKZOMAG-UHFFFAOYSA-N 2-[5-[3-[4-(4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)phenoxy]propoxy]indol-1-yl]propanoic acid Chemical compound C1CCCC(S2)=C1N=C2C(C=C1)=CC=C1OCCCOC1=CC=C2N(C(C(O)=O)C)C=CC2=C1 ZHLAZEYLKZOMAG-UHFFFAOYSA-N 0.000 claims 1
- CWQWKEHJHNRXJT-UHFFFAOYSA-N 2-[5-[3-[4-(4,5,6,7-tetrahydro-1,3-benzoxazol-2-yl)phenoxy]propoxy]indol-1-yl]acetic acid Chemical compound C1CCCC(O2)=C1N=C2C(C=C1)=CC=C1OCCCOC1=CC=C2N(CC(=O)O)C=CC2=C1 CWQWKEHJHNRXJT-UHFFFAOYSA-N 0.000 claims 1
- SBACZFSBEXLNAO-UHFFFAOYSA-N 2-[5-[3-[4-(4-ethoxy-5-methyl-1,3-thiazol-2-yl)-2-propylphenoxy]propoxy]-1h-indol-2-yl]acetic acid Chemical compound C=1C=C(OCCCOC=2C=C3C=C(CC(O)=O)NC3=CC=2)C(CCC)=CC=1C1=NC(OCC)=C(C)S1 SBACZFSBEXLNAO-UHFFFAOYSA-N 0.000 claims 1
- ZQWMVCCGKMAIIC-UHFFFAOYSA-N 2-[5-[3-[4-(4-ethyl-1,3-oxazol-2-yl)-2-propylphenoxy]propoxy]-3-methyl-1h-indol-2-yl]acetic acid Chemical compound C=1C=C(OCCCOC=2C=C3C(C)=C(CC(O)=O)NC3=CC=2)C(CCC)=CC=1C1=NC(CC)=CO1 ZQWMVCCGKMAIIC-UHFFFAOYSA-N 0.000 claims 1
- IMDOFSUZTMLYHH-UHFFFAOYSA-N 2-[5-[3-[4-(4-ethyl-1,3-oxazol-2-yl)-2-propylphenoxy]propoxy]indol-1-yl]acetic acid Chemical compound C=1C=C(OCCCOC=2C=C3C=CN(CC(O)=O)C3=CC=2)C(CCC)=CC=1C1=NC(CC)=CO1 IMDOFSUZTMLYHH-UHFFFAOYSA-N 0.000 claims 1
- FBOPTUMPRDCVNM-UHFFFAOYSA-N 2-[5-[3-[4-(4-ethyl-1,3-thiazol-2-yl)-2-propylphenoxy]propoxy]indol-1-yl]acetic acid Chemical compound C=1C=C(OCCCOC=2C=C3C=CN(CC(O)=O)C3=CC=2)C(CCC)=CC=1C1=NC(CC)=CS1 FBOPTUMPRDCVNM-UHFFFAOYSA-N 0.000 claims 1
- LCZCQUCAQSAYAG-UHFFFAOYSA-N 2-[5-[3-[4-(4-tert-butyl-1,3-oxazol-2-yl)-2-propylphenoxy]propoxy]-3-methyl-1h-indol-2-yl]acetic acid Chemical compound C=1C=C(OCCCOC=2C=C3C(C)=C(CC(O)=O)NC3=CC=2)C(CCC)=CC=1C1=NC(C(C)(C)C)=CO1 LCZCQUCAQSAYAG-UHFFFAOYSA-N 0.000 claims 1
- LKLAYFOHAOUMQE-UHFFFAOYSA-N 2-[5-[3-[4-(6,7-dihydro-5h-pyrano[2,3-d][1,3]thiazol-2-yl)-2-propylphenoxy]propoxy]indol-1-yl]acetic acid Chemical compound O1CCCC(S2)=C1N=C2C1=CC=C(OCCCOC=2C=C3C=CN(CC(O)=O)C3=CC=2)C(CCC)=C1 LKLAYFOHAOUMQE-UHFFFAOYSA-N 0.000 claims 1
- KOTREZXUBKZABP-UHFFFAOYSA-N 2-[5-[3-[4-[5-(dimethylcarbamoyl)-4-methyl-1,3-thiazol-2-yl]-2-propylphenoxy]propoxy]-1h-indol-2-yl]acetic acid Chemical compound C=1C=C(OCCCOC=2C=C3C=C(CC(O)=O)NC3=CC=2)C(CCC)=CC=1C1=NC(C)=C(C(=O)N(C)C)S1 KOTREZXUBKZABP-UHFFFAOYSA-N 0.000 claims 1
- 229940124802 CB1 antagonist Drugs 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- 206010056997 Impaired fasting glucose Diseases 0.000 claims 1
- 229940086609 Lipase inhibitor Drugs 0.000 claims 1
- 108010025020 Nerve Growth Factor Proteins 0.000 claims 1
- 102000007072 Nerve Growth Factors Human genes 0.000 claims 1
- 108090000189 Neuropeptides Proteins 0.000 claims 1
- 102000003797 Neuropeptides Human genes 0.000 claims 1
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims 1
- 201000010390 abdominal obesity-metabolic syndrome 1 Diseases 0.000 claims 1
- 239000000556 agonist Substances 0.000 claims 1
- 239000002830 appetite depressant Substances 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 235000014113 dietary fatty acids Nutrition 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 229940030606 diuretics Drugs 0.000 claims 1
- 239000002552 dosage form Substances 0.000 claims 1
- 239000002792 enkephalinase inhibitor Substances 0.000 claims 1
- 229930195729 fatty acid Natural products 0.000 claims 1
- 239000000194 fatty acid Substances 0.000 claims 1
- 150000004665 fatty acids Chemical class 0.000 claims 1
- 230000009229 glucose formation Effects 0.000 claims 1
- 230000002440 hepatic effect Effects 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
- 239000004026 insulin derivative Substances 0.000 claims 1
- 230000000366 juvenile effect Effects 0.000 claims 1
- 150000002632 lipids Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 208000011661 metabolic syndrome X Diseases 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 239000003900 neurotrophic factor Substances 0.000 claims 1
- 239000000137 peptide hydrolase inhibitor Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 0 COc1ccc(c(C(*)C(O*)=O)c[n]2*)c2c1 Chemical compound COc1ccc(c(C(*)C(O*)=O)c[n]2*)c2c1 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US46614303P | 2003-04-28 | 2003-04-28 | |
| US60/466,143 | 2003-04-28 | ||
| PCT/US2004/012959 WO2004098498A2 (en) | 2003-04-28 | 2004-04-28 | Indole acetic acid derivatives and their use as pharmaceutical agents |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010261427A Division JP2011063613A (ja) | 2003-04-28 | 2010-11-24 | インドール酢酸誘導体および薬剤としてのそれらの使用 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2006524709A JP2006524709A (ja) | 2006-11-02 |
| JP2006524709A5 true JP2006524709A5 (https=) | 2007-06-14 |
| JP4828414B2 JP4828414B2 (ja) | 2011-11-30 |
Family
ID=33434943
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006513366A Expired - Fee Related JP4828414B2 (ja) | 2003-04-28 | 2004-04-28 | インドール酢酸誘導体および薬剤としてのそれらの使用 |
| JP2010261427A Pending JP2011063613A (ja) | 2003-04-28 | 2010-11-24 | インドール酢酸誘導体および薬剤としてのそれらの使用 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010261427A Pending JP2011063613A (ja) | 2003-04-28 | 2010-11-24 | インドール酢酸誘導体および薬剤としてのそれらの使用 |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US7592361B2 (https=) |
| EP (1) | EP1620088A4 (https=) |
| JP (2) | JP4828414B2 (https=) |
| CA (1) | CA2523245C (https=) |
| WO (1) | WO2004098498A2 (https=) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1630152A4 (en) * | 2003-05-30 | 2009-09-23 | Takeda Pharmaceutical | CONDENSED CYCLIC COMPOUND |
| JP4805552B2 (ja) * | 2003-05-30 | 2011-11-02 | 武田薬品工業株式会社 | 縮合環化合物 |
| JP4641942B2 (ja) | 2003-10-03 | 2011-03-02 | フェーイレン・ナムローゼ・フェンノートシャップ | ヒトおよび動物におけるｉｇｆ−１血清レベルの低下と関連した種々の疾患状態の治療用の治療用組成物の製造のための血清中ｉｇｆ−１レベルを増加できる化合物の使用 |
| US7622491B2 (en) * | 2004-08-13 | 2009-11-24 | Metabolex Inc. | Modulators of PPAR and methods of their preparation |
| CA2602336A1 (en) | 2005-03-31 | 2006-10-05 | Ucb Pharma S.A. | Compounds comprising an oxazole or thiazole moiety, processes for making them, and their uses |
| EP2759533B1 (en) | 2011-09-22 | 2017-08-02 | Takeda Pharmaceutical Company Limited | Condensed heterocyclic compound |
| KR101808196B1 (ko) * | 2016-01-08 | 2017-12-14 | 대한민국(농촌진흥청장) | 왕지네 유래 신규 화합물 및 이의 항혈전 용도 |
| CN106702003B (zh) * | 2017-02-28 | 2021-02-12 | 固安博健生物技术有限公司 | Hsdl1在诊治骨肉瘤中的应用 |
| CN117326903B (zh) * | 2023-09-27 | 2025-05-02 | 常州大学 | 一种高立体选择性合成n-烷基化吲哚衍生物的方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996014843A2 (en) * | 1994-11-10 | 1996-05-23 | Cor Therapeutics, Inc. | Pharmaceutical pyrazole compositions useful as inhibitors of protein kinases |
| CA2383983C (en) * | 1998-03-31 | 2009-09-29 | The Institutes For Pharmaceutical Discovery, Llc | Substituted indolealkanoic acids |
| GB9820113D0 (en) * | 1998-09-15 | 1998-11-11 | Merck Sharp & Dohme | Therapeutic agents |
| TNSN99224A1 (fr) * | 1998-12-01 | 2005-11-10 | Inst For Pharm Discovery Inc | Methodes de reduction des niveaux de glucose et triglyceride en serum et pour suppression de l'antigenese utilisant les acides la indolealkanoique |
| DE10006139A1 (de) * | 2000-02-11 | 2001-08-16 | Merck Patent Gmbh | Indol-3-yl-Derivate |
| MXPA03000488A (es) * | 2000-07-19 | 2003-06-24 | Procter & Gamble | Composiciones para el lavado automatico de trastes en forma de gel, metodos de preparacion y uso de las mismas. |
| US20020072518A1 (en) * | 2000-08-29 | 2002-06-13 | Khanna Ish Kumar | Bicyclic alphavbeta3 antagonists |
| NZ539682A (en) * | 2001-01-29 | 2006-03-31 | Dimensional Pharm Inc | Substituted indoles and their use as integrin antagonists |
| HRP20040164A2 (en) * | 2001-08-29 | 2004-10-31 | Warner Lambert Co | Oral antidiabetic agents |
| US20070208026A1 (en) * | 2003-04-07 | 2007-09-06 | Liu Kevin | N-Containing Heteroaromatic Compounds As Modulators Of Ppars And Methods Of Treating Metabolic Disorders |
-
2004
- 2004-04-28 US US10/555,024 patent/US7592361B2/en not_active Expired - Fee Related
- 2004-04-28 CA CA2523245A patent/CA2523245C/en not_active Expired - Fee Related
- 2004-04-28 JP JP2006513366A patent/JP4828414B2/ja not_active Expired - Fee Related
- 2004-04-28 WO PCT/US2004/012959 patent/WO2004098498A2/en not_active Ceased
- 2004-04-28 EP EP04750750A patent/EP1620088A4/en not_active Withdrawn
-
2009
- 2009-07-23 US US12/508,314 patent/US7964622B2/en not_active Expired - Fee Related
-
2010
- 2010-11-24 JP JP2010261427A patent/JP2011063613A/ja active Pending
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