JP2004534733A5 - - Google Patents
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- JP2004534733A5 JP2004534733A5 JP2002563152A JP2002563152A JP2004534733A5 JP 2004534733 A5 JP2004534733 A5 JP 2004534733A5 JP 2002563152 A JP2002563152 A JP 2002563152A JP 2002563152 A JP2002563152 A JP 2002563152A JP 2004534733 A5 JP2004534733 A5 JP 2004534733A5
- Authority
- JP
- Japan
- Prior art keywords
- salt
- ethoxy
- substituted
- pyrazolo
- dihydro
- 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.)
- Pending
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- 150000003839 salts Chemical class 0.000 claims 164
- 239000011780 sodium chloride Substances 0.000 claims 164
- -1 aralkoxyalkyl Chemical group 0.000 claims 114
- 125000000217 alkyl group Chemical group 0.000 claims 65
- 125000003710 aryl alkyl group Chemical group 0.000 claims 54
- 150000001875 compounds Chemical class 0.000 claims 54
- 229910052739 hydrogen Inorganic materials 0.000 claims 51
- 239000001257 hydrogen Substances 0.000 claims 51
- 150000003863 ammonium salts Chemical class 0.000 claims 50
- 125000003118 aryl group Chemical group 0.000 claims 49
- 125000000623 heterocyclic group Chemical group 0.000 claims 43
- 125000004475 heteroaralkyl group Chemical group 0.000 claims 38
- 125000001072 heteroaryl group Chemical group 0.000 claims 38
- 125000003545 alkoxy group Chemical group 0.000 claims 37
- 150000002431 hydrogen Chemical class 0.000 claims 35
- 125000004104 aryloxy group Chemical group 0.000 claims 33
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 33
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 31
- 125000001589 carboacyl group Chemical group 0.000 claims 31
- 125000000753 cycloalkyl group Chemical group 0.000 claims 30
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 29
- 125000003435 aroyl group Chemical group 0.000 claims 28
- 125000001769 aryl amino group Chemical group 0.000 claims 27
- 229910052736 halogen Inorganic materials 0.000 claims 27
- 150000002367 halogens Chemical class 0.000 claims 27
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 27
- 239000004381 Choline salt Substances 0.000 claims 25
- ZBCBWPMODOFKDW-UHFFFAOYSA-N Diethanolamine Chemical class OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims 25
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical class NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims 25
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminum Chemical class [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims 25
- 235000019417 choline salt Nutrition 0.000 claims 25
- 150000002357 guanidines Chemical class 0.000 claims 25
- JMHRGKDWGWORNU-UHFFFAOYSA-M sodium;2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetate Chemical compound [Na+].CC1=C(CC([O-])=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 JMHRGKDWGWORNU-UHFFFAOYSA-M 0.000 claims 25
- 125000004663 dialkyl amino group Chemical group 0.000 claims 24
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 22
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims 22
- 125000004103 aminoalkyl group Chemical group 0.000 claims 21
- 125000004001 thioalkyl group Chemical group 0.000 claims 21
- 125000004414 alkyl thio group Chemical group 0.000 claims 20
- 150000001483 arginine derivatives Chemical class 0.000 claims 19
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims 18
- 150000003248 quinolines Chemical class 0.000 claims 18
- 125000004423 acyloxy group Chemical group 0.000 claims 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 16
- 229910052757 nitrogen Inorganic materials 0.000 claims 16
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 15
- 229910052799 carbon Inorganic materials 0.000 claims 14
- 125000004432 carbon atoms Chemical group C* 0.000 claims 14
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims 14
- 229910052760 oxygen Inorganic materials 0.000 claims 14
- 201000010099 disease Diseases 0.000 claims 12
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 10
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 9
- 125000005100 aryl amino carbonyl group Chemical group 0.000 claims 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 9
- 239000012453 solvate Substances 0.000 claims 9
- 206010022489 Insulin resistance Diseases 0.000 claims 8
- 125000004442 acylamino group Chemical group 0.000 claims 8
- 150000001735 carboxylic acids Chemical class 0.000 claims 8
- 150000002829 nitrogen Chemical group 0.000 claims 8
- 239000001301 oxygen Substances 0.000 claims 8
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical group O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 8
- 229910052717 sulfur Inorganic materials 0.000 claims 8
- 229910052782 aluminium Chemical class 0.000 claims 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 7
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims 7
- 150000003460 sulfonic acids Chemical class 0.000 claims 7
- CFFUDUBKYHMHOF-UHFFFAOYSA-N 2-ethoxy-3-[4-[2-(1-methyl-7-oxo-3,5-dipropylpyrazolo[4,3-d]pyrimidin-6-yl)ethoxy]phenyl]propanoic acid Chemical compound CCCC1=NN(C)C(C2=O)=C1N=C(CCC)N2CCOC1=CC=C(CC(OCC)C(O)=O)C=C1 CFFUDUBKYHMHOF-UHFFFAOYSA-N 0.000 claims 6
- XAWRDWCILPXSAR-UHFFFAOYSA-N 2-ethoxy-3-[4-[2-(5-ethyl-1-methyl-7-oxo-3-propylpyrazolo[4,3-d]pyrimidin-6-yl)ethoxy]phenyl]propanoic acid Chemical compound CCCC1=NN(C)C(C2=O)=C1N=C(CC)N2CCOC1=CC=C(CC(OCC)C(O)=O)C=C1 XAWRDWCILPXSAR-UHFFFAOYSA-N 0.000 claims 6
- UAPQKLTXQPVJGQ-UHFFFAOYSA-N 3-[4-[2-(1,5-dimethyl-7-oxo-3-propylpyrazolo[4,3-d]pyrimidin-6-yl)ethoxy]phenyl]-2-ethoxypropanoic acid Chemical compound CCCC1=NN(C)C(C2=O)=C1N=C(C)N2CCOC1=CC=C(CC(OCC)C(O)=O)C=C1 UAPQKLTXQPVJGQ-UHFFFAOYSA-N 0.000 claims 6
- MEXINNDTWUQJLN-UHFFFAOYSA-N 3-[4-[2-(1,5-dimethyl-7-oxo-3-propylpyrazolo[4,3-d]pyrimidin-6-yl)ethoxy]phenyl]-2-phenoxypropanoic acid Chemical compound CCCC1=NN(C)C(C2=O)=C1N=C(C)N2CCOC(C=C1)=CC=C1CC(C(O)=O)OC1=CC=CC=C1 MEXINNDTWUQJLN-UHFFFAOYSA-N 0.000 claims 6
- IXVLDWMUCMXRBE-UHFFFAOYSA-N 3-[4-[2-(1-methyl-7-oxo-3,5-dipropylpyrazolo[4,3-d]pyrimidin-6-yl)ethoxy]phenyl]-2-phenoxypropanoic acid Chemical compound CCCC1=NN(C)C(C2=O)=C1N=C(CCC)N2CCOC(C=C1)=CC=C1CC(C(O)=O)OC1=CC=CC=C1 IXVLDWMUCMXRBE-UHFFFAOYSA-N 0.000 claims 6
- RUFUUNYWEHLOBL-UHFFFAOYSA-N 3-[4-[2-(5-benzyl-1-methyl-7-oxo-3-propylpyrazolo[4,3-d]pyrimidin-6-yl)ethoxy]phenyl]-2-ethoxypropanoic acid Chemical compound CCCC1=NN(C)C(C(N2CCOC=3C=CC(CC(OCC)C(O)=O)=CC=3)=O)=C1N=C2CC1=CC=CC=C1 RUFUUNYWEHLOBL-UHFFFAOYSA-N 0.000 claims 6
- HRWMHPWYDAFBNO-UHFFFAOYSA-N 3-[4-[2-(5-benzyl-1-methyl-7-oxo-3-propylpyrazolo[4,3-d]pyrimidin-6-yl)ethoxy]phenyl]-2-phenoxypropanoic acid Chemical compound CCCC1=NN(C)C(C(N2CCOC=3C=CC(CC(OC=4C=CC=CC=4)C(O)=O)=CC=3)=O)=C1N=C2CC1=CC=CC=C1 HRWMHPWYDAFBNO-UHFFFAOYSA-N 0.000 claims 6
- DRPVKFGJSHSDFA-UHFFFAOYSA-N 3-[4-[2-(5-ethyl-1-methyl-7-oxo-3-propylpyrazolo[4,3-d]pyrimidin-6-yl)ethoxy]phenyl]-2-phenoxypropanoic acid Chemical compound CCCC1=NN(C)C(C2=O)=C1N=C(CC)N2CCOC(C=C1)=CC=C1CC(C(O)=O)OC1=CC=CC=C1 DRPVKFGJSHSDFA-UHFFFAOYSA-N 0.000 claims 6
- 239000004475 Arginine Substances 0.000 claims 6
- 206010003210 Arteriosclerosis Diseases 0.000 claims 6
- 208000002705 Glucose Intolerance Diseases 0.000 claims 6
- 206010020772 Hypertension Diseases 0.000 claims 6
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims 6
- 239000004472 Lysine Substances 0.000 claims 6
- 208000008589 Obesity Diseases 0.000 claims 6
- 208000001132 Osteoporosis Diseases 0.000 claims 6
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims 6
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- 125000004122 cyclic group Chemical group 0.000 claims 6
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 6
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 6
- 235000020824 obesity Nutrition 0.000 claims 6
- 239000008194 pharmaceutical composition Substances 0.000 claims 6
- 201000010065 polycystic ovary syndrome Diseases 0.000 claims 6
- 208000001083 Kidney Disease Diseases 0.000 claims 5
- 239000003795 chemical substances by application Substances 0.000 claims 5
- 238000007796 conventional method Methods 0.000 claims 5
- 238000002360 preparation method Methods 0.000 claims 5
- 206010062060 Hyperlipidaemia Diseases 0.000 claims 4
- 210000002381 Plasma Anatomy 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- PVNIIMVLHYAWGP-UHFFFAOYSA-N nicotinic acid Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- 208000008787 Cardiovascular Disease Diseases 0.000 claims 3
- 206010012289 Dementia Diseases 0.000 claims 3
- 208000002249 Diabetes Complications Diseases 0.000 claims 3
- 206010012601 Diabetes mellitus Diseases 0.000 claims 3
- 206010012655 Diabetic complications Diseases 0.000 claims 3
- 206010058108 Dyslipidaemia Diseases 0.000 claims 3
- 210000002889 Endothelial Cells Anatomy 0.000 claims 3
- 206010018364 Glomerulonephritis Diseases 0.000 claims 3
- 206010061989 Glomerulosclerosis Diseases 0.000 claims 3
- 208000009576 Hypercholesterolemia Diseases 0.000 claims 3
- 206010021972 Inflammatory bowel disease Diseases 0.000 claims 3
- NRYBAZVQPHGZNS-ZSOCWYAHSA-N Leptin Chemical compound O=C([C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](N)CC(C)C)CCSC)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](CS)C(O)=O NRYBAZVQPHGZNS-ZSOCWYAHSA-N 0.000 claims 3
- 102000016267 Leptin Human genes 0.000 claims 3
- 108010092277 Leptin Proteins 0.000 claims 3
- 206010029149 Nephropathy Diseases 0.000 claims 3
- 206010029151 Nephropathy Diseases 0.000 claims 3
- 206010029164 Nephrotic syndrome Diseases 0.000 claims 3
- 108009000551 Nephrotic syndrome Proteins 0.000 claims 3
- 206010033645 Pancreatitis Diseases 0.000 claims 3
- 206010038932 Retinopathy Diseases 0.000 claims 3
- 206010038923 Retinopathy Diseases 0.000 claims 3
- 206010048214 Xanthoma Diseases 0.000 claims 3
- 125000003282 alkyl amino group Chemical group 0.000 claims 3
- 201000001320 atherosclerosis Diseases 0.000 claims 3
- 201000011510 cancer Diseases 0.000 claims 3
- 230000020411 cell activation Effects 0.000 claims 3
- 201000008739 coronary artery disease Diseases 0.000 claims 3
- 229940079593 drugs Drugs 0.000 claims 3
- ALSHATAKPJWDIL-UHFFFAOYSA-N ethyl 3-[4-[2-(1,5-dimethyl-7-oxo-3-propylpyrazolo[4,3-d]pyrimidin-6-yl)ethoxy]phenyl]-2-phenoxypropanoate Chemical compound CCCC1=NN(C)C(C2=O)=C1N=C(C)N2CCOC(C=C1)=CC=C1CC(C(=O)OCC)OC1=CC=CC=C1 ALSHATAKPJWDIL-UHFFFAOYSA-N 0.000 claims 3
- TZUGFLSWNARQAG-UHFFFAOYSA-N ethyl 3-[4-[2-(1-methyl-7-oxo-3,5-dipropylpyrazolo[4,3-d]pyrimidin-6-yl)ethoxy]phenyl]-2-phenoxypropanoate Chemical compound CCCC1=NN(C)C(C2=O)=C1N=C(CCC)N2CCOC(C=C1)=CC=C1CC(C(=O)OCC)OC1=CC=CC=C1 TZUGFLSWNARQAG-UHFFFAOYSA-N 0.000 claims 3
- VUDNLHWOTCGUON-UHFFFAOYSA-N ethyl 3-[4-[2-(5-benzyl-1-methyl-7-oxo-3-propylpyrazolo[4,3-d]pyrimidin-6-yl)ethoxy]phenyl]-2-phenoxypropanoate Chemical compound CCCC1=NN(C)C(C(N2CCOC=3C=CC(CC(OC=4C=CC=CC=4)C(=O)OCC)=CC=3)=O)=C1N=C2CC1=CC=CC=C1 VUDNLHWOTCGUON-UHFFFAOYSA-N 0.000 claims 3
- JBTCMKNCZRWNIH-UHFFFAOYSA-N ethyl 3-[4-[2-(5-ethyl-1-methyl-7-oxo-3-propylpyrazolo[4,3-d]pyrimidin-6-yl)ethoxy]phenyl]-2-phenoxypropanoate Chemical compound CCCC1=NN(C)C(C2=O)=C1N=C(CC)N2CCOC(C=C1)=CC=C1CC(C(=O)OCC)OC1=CC=CC=C1 JBTCMKNCZRWNIH-UHFFFAOYSA-N 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- 201000001421 hyperglycemia Diseases 0.000 claims 3
- 230000001631 hypertensive Effects 0.000 claims 3
- 229940039781 leptin Drugs 0.000 claims 3
- 201000009925 nephrosclerosis Diseases 0.000 claims 3
- 230000001991 pathophysiological Effects 0.000 claims 3
- 201000004681 psoriasis Diseases 0.000 claims 3
- 201000010874 syndrome Diseases 0.000 claims 3
- 229920001268 Cholestyramine Polymers 0.000 claims 2
- GMRWGQCZJGVHKL-UHFFFAOYSA-N Colestipol Chemical compound ClCC1CO1.NCCNCCNCCNCCN GMRWGQCZJGVHKL-UHFFFAOYSA-N 0.000 claims 2
- 229920002911 Colestipol Polymers 0.000 claims 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N D-Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims 2
- 241000229754 Iva xanthiifolia Species 0.000 claims 2
- 108010028554 LDL Cholesterol Proteins 0.000 claims 2
- 206010061227 Lipid metabolism disease Diseases 0.000 claims 2
- 206010068871 Myotonic dystrophy Diseases 0.000 claims 2
- FYPMFJGVHOHGLL-UHFFFAOYSA-N Probucol Chemical compound C=1C(C(C)(C)C)=C(O)C(C(C)(C)C)=CC=1SC(C)(C)SC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 FYPMFJGVHOHGLL-UHFFFAOYSA-N 0.000 claims 2
- 108010069201 VLDL Cholesterol Proteins 0.000 claims 2
- HGMSJMJPXGGEBP-UHFFFAOYSA-N [4-[3-(4-ethylphenyl)butyl]phenyl]-trimethylazanium Chemical compound C1=CC(CC)=CC=C1C(C)CCC1=CC=C([N+](C)(C)C)C=C1 HGMSJMJPXGGEBP-UHFFFAOYSA-N 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 2
- 229960002604 colestipol Drugs 0.000 claims 2
- 235000014113 dietary fatty acids Nutrition 0.000 claims 2
- 235000014632 disordered eating Nutrition 0.000 claims 2
- 201000006180 eating disease Diseases 0.000 claims 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 2
- 239000000194 fatty acid Substances 0.000 claims 2
- 150000004665 fatty acids Chemical class 0.000 claims 2
- 239000008103 glucose Substances 0.000 claims 2
- 125000005842 heteroatoms Chemical group 0.000 claims 2
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims 2
- 230000002757 inflammatory Effects 0.000 claims 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 2
- 229960003512 nicotinic acid Drugs 0.000 claims 2
- 235000001968 nicotinic acid Nutrition 0.000 claims 2
- 239000011664 nicotinic acid Substances 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 229960003912 probucol Drugs 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 239000011593 sulfur Chemical group 0.000 claims 2
- 150000003626 triacylglycerols Chemical class 0.000 claims 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N β-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 206010018429 Glucose tolerance impaired Diseases 0.000 claims 1
- MNQZXJOMYWMBOU-UHFFFAOYSA-N Glyceraldehyde Chemical compound OCC(O)C=O MNQZXJOMYWMBOU-UHFFFAOYSA-N 0.000 claims 1
- 206010038428 Renal disease Diseases 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 239000003288 aldose reductase inhibitor Substances 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 150000008064 anhydrides Chemical group 0.000 claims 1
- 125000005334 azaindolyl group Chemical group N1N=C(C2=CC=CC=C12)* 0.000 claims 1
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 239000002775 capsule Substances 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 230000003920 cognitive function Effects 0.000 claims 1
- 238000006297 dehydration reaction Methods 0.000 claims 1
- 125000004598 dihydrobenzofuryl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 125000004430 oxygen atoms Chemical group O* 0.000 claims 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 1
- 239000000843 powder Substances 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 claims 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 125000000542 sulfonic acid group Chemical group 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
- 239000006188 syrup Substances 0.000 claims 1
- 235000020357 syrup Nutrition 0.000 claims 1
- 239000003826 tablet Substances 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US26659501P | 2001-02-05 | 2001-02-05 | |
| IN569CH2001 | 2001-07-10 | ||
| PCT/IB2002/000342 WO2002062799A1 (en) | 2001-02-05 | 2002-02-05 | Aryl substituted alkylcarboxylic acids as hypocholesterolemic agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2004534733A JP2004534733A (ja) | 2004-11-18 |
| JP2004534733A5 true JP2004534733A5 (hu) | 2005-12-22 |
Family
ID=26324873
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002563152A Pending JP2004534733A (ja) | 2001-02-05 | 2002-02-05 | 血中コレステロール低下剤剤としてのアリール置換アルキルカルボン酸 |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP1363914A1 (hu) |
| JP (1) | JP2004534733A (hu) |
| CA (1) | CA2436741A1 (hu) |
| WO (1) | WO2002062799A1 (hu) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HN2002000317A (es) * | 2001-11-02 | 2003-05-21 | Pfizer | Inhibidores de pde9 para tratamiento de trastornos cardiovasculares |
| US20080125403A1 (en) | 2004-04-02 | 2008-05-29 | Merck & Co., Inc. | Method of Treating Men with Metabolic and Anthropometric Disorders |
| JP2008512384A (ja) * | 2004-09-06 | 2008-04-24 | ドクター レディズ ラボラトリーズ リミテッド | Ｐｐａｒアゴニスト活性を有するフィブラート化合物 |
| US7674822B2 (en) | 2004-11-24 | 2010-03-09 | Wyeth | PTP1b inhibitors |
| US8969514B2 (en) | 2007-06-04 | 2015-03-03 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia, atherosclerosis, coronary heart disease, gallstone, obesity and other cardiovascular diseases |
| ES2393885T7 (es) | 2007-06-04 | 2014-01-30 | Synergy Pharmaceuticals Inc. | Agonistas de la guanilato ciclasa útiles para el tratamiento de trastornos gastrointestinales, inflamación, cáncer y otros trastornos |
| ES2522968T3 (es) | 2008-06-04 | 2014-11-19 | Synergy Pharmaceuticals Inc. | Agonistas de guanilato ciclasa útiles para el tratamiento de trastornos gastrointestinales, inflamación, cáncer y otros trastornos |
| AU2009270833B2 (en) | 2008-07-16 | 2015-02-19 | Bausch Health Ireland Limited | Agonists of guanylate cyclase useful for the treatment of gastrointestinal, inflammation, cancer and other disorders |
| MX2011004258A (es) | 2008-10-22 | 2011-06-01 | Merck Sharp & Dohme | Derivados de bencimidazol ciclicos novedosos utiles como agentes anti-diabeticos. |
| CA2741672A1 (en) | 2008-10-31 | 2010-05-06 | Merck Sharp & Dohme Corp. | Novel cyclic benzimidazole derivatives useful anti-diabetic agents |
| CA2786314A1 (en) | 2010-02-25 | 2011-09-01 | Merck Sharp & Dohme Corp. | Novel cyclic benzimidazole derivatives useful anti-diabetic agents |
| WO2012027331A1 (en) | 2010-08-27 | 2012-03-01 | Ironwood Pharmaceuticals, Inc. | Compositions and methods for treating or preventing metabolic syndrome and related diseases and disorders |
| US9616097B2 (en) | 2010-09-15 | 2017-04-11 | Synergy Pharmaceuticals, Inc. | Formulations of guanylate cyclase C agonists and methods of use |
| KR101668514B1 (ko) | 2011-02-25 | 2016-10-21 | 머크 샤프 앤드 돔 코포레이션 | 항당뇨병제로서 유용한 신규 시클릭 아자벤즈이미다졸 유도체 |
| US20150004144A1 (en) | 2011-12-02 | 2015-01-01 | The General Hospital Corporation | Differentiation into brown adipocytes |
| JP2015525782A (ja) | 2012-08-02 | 2015-09-07 | メルク・シャープ・アンド・ドーム・コーポレーションＭｅｒｃｋ Ｓｈａｒｐ ＆ Ｄｏｈｍｅ Ｃｏｒｐ． | 抗糖尿病性三環式化合物 |
| RU2015140066A (ru) | 2013-02-22 | 2017-03-30 | Мерк Шарп И Доум Корп. | Противодиабетические бициклические соединения |
| US9650375B2 (en) | 2013-03-14 | 2017-05-16 | Merck Sharp & Dohme Corp. | Indole derivatives useful as anti-diabetic agents |
| CA2905435A1 (en) | 2013-03-15 | 2014-09-25 | Synergy Pharmaceuticals Inc. | Compositions useful for the treatment of gastrointestinal disorders |
| JP2016514671A (ja) | 2013-03-15 | 2016-05-23 | シナジー ファーマシューティカルズ インコーポレイテッド | グアニル酸シクラーゼのアゴニストおよびその使用 |
| US10011637B2 (en) | 2013-06-05 | 2018-07-03 | Synergy Pharmaceuticals, Inc. | Ultra-pure agonists of guanylate cyclase C, method of making and using same |
| WO2015051496A1 (en) | 2013-10-08 | 2015-04-16 | Merck Sharp & Dohme Corp. | Antidiabetic tricyclic compounds |
| WO2018106518A1 (en) | 2016-12-06 | 2018-06-14 | Merck Sharp & Dohme Corp. | Antidiabetic heterocyclic compounds |
| US10968232B2 (en) | 2016-12-20 | 2021-04-06 | Merck Sharp & Dohme Corp. | Antidiabetic spirochroman compounds |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0903343B1 (en) * | 1997-09-19 | 2003-05-28 | SSP Co., Ltd. | Alpha-Substituted phenylpropionic acid derivative and medicine containing the same |
| CN1208326C (zh) * | 1998-04-23 | 2005-06-29 | 雷迪实验室有限公司 | 杂环化合物及其在医药方面的应用、其制备方法及含有它们的药物组合物 |
-
2002
- 2002-02-05 CA CA002436741A patent/CA2436741A1/en not_active Abandoned
- 2002-02-05 JP JP2002563152A patent/JP2004534733A/ja active Pending
- 2002-02-05 WO PCT/IB2002/000342 patent/WO2002062799A1/en not_active Application Discontinuation
- 2002-02-05 EP EP02711126A patent/EP1363914A1/en not_active Withdrawn
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