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 134
- -1 aralkoxyalkyl Chemical group 0.000 claims 111
- 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 49
- 125000001072 heteroaryl group Chemical group 0.000 claims 44
- 125000004475 heteroaralkyl 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
- 125000001589 carboacyl group Chemical group 0.000 claims 32
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 32
- 125000004183 alkoxy alkyl 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
- 229910052736 halogen Inorganic materials 0.000 claims 28
- 150000002367 halogens Chemical class 0.000 claims 28
- 125000001769 aryl amino group Chemical group 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
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical class NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims 25
- 150000001483 arginine derivatives Chemical class 0.000 claims 25
- 235000019417 choline salt Nutrition 0.000 claims 25
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical class OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims 25
- 150000002357 guanidines Chemical class 0.000 claims 25
- 150000003248 quinolines Chemical class 0.000 claims 25
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 claims 25
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 claims 24
- 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
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 16
- 125000004423 acyloxy group Chemical group 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 atom Chemical group C* 0.000 claims 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 14
- 238000000034 method Methods 0.000 claims 14
- 229910052760 oxygen Inorganic materials 0.000 claims 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 12
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 12
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 10
- 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 9
- 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 9
- 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
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 8
- 150000001735 carboxylic acids Chemical class 0.000 claims 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 8
- 239000001301 oxygen Substances 0.000 claims 8
- 229910052717 sulfur Inorganic materials 0.000 claims 8
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 7
- 150000003460 sulfonic acids Chemical class 0.000 claims 7
- 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
- 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
- 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
- 208000002705 Glucose Intolerance Diseases 0.000 claims 6
- 206010020772 Hypertension Diseases 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
- 201000010099 disease Diseases 0.000 claims 6
- 208000035475 disorder Diseases 0.000 claims 6
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 6
- 208000017169 kidney disease Diseases 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
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 201000010065 polycystic ovary syndrome Diseases 0.000 claims 6
- FKRCODPIKNYEAC-UHFFFAOYSA-N propionic acid ethyl ester Natural products CCOC(=O)CC FKRCODPIKNYEAC-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 5
- 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 5
- 239000003795 chemical substances by application Substances 0.000 claims 5
- 238000007796 conventional method Methods 0.000 claims 5
- 201000009104 prediabetes syndrome Diseases 0.000 claims 5
- 238000002360 preparation method Methods 0.000 claims 5
- 208000031226 Hyperlipidaemia Diseases 0.000 claims 4
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- 206010003210 Arteriosclerosis Diseases 0.000 claims 3
- 201000001320 Atherosclerosis Diseases 0.000 claims 3
- 208000024172 Cardiovascular disease Diseases 0.000 claims 3
- 206010012289 Dementia Diseases 0.000 claims 3
- 208000002249 Diabetes Complications Diseases 0.000 claims 3
- 206010012655 Diabetic complications Diseases 0.000 claims 3
- 208000032928 Dyslipidaemia Diseases 0.000 claims 3
- 206010018364 Glomerulonephritis Diseases 0.000 claims 3
- 208000035150 Hypercholesterolemia Diseases 0.000 claims 3
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 3
- 102000016267 Leptin Human genes 0.000 claims 3
- 108010092277 Leptin Proteins 0.000 claims 3
- 206010028980 Neoplasm Diseases 0.000 claims 3
- 206010029164 Nephrotic syndrome Diseases 0.000 claims 3
- 206010033645 Pancreatitis Diseases 0.000 claims 3
- 201000004681 Psoriasis Diseases 0.000 claims 3
- 208000017442 Retinal disease Diseases 0.000 claims 3
- 206010038923 Retinopathy Diseases 0.000 claims 3
- 206010048215 Xanthomatosis Diseases 0.000 claims 3
- 125000003282 alkyl amino group Chemical group 0.000 claims 3
- 208000011775 arteriosclerosis disease Diseases 0.000 claims 3
- 201000011510 cancer Diseases 0.000 claims 3
- 230000020411 cell activation Effects 0.000 claims 3
- 208000029078 coronary artery disease Diseases 0.000 claims 3
- 229940079593 drug Drugs 0.000 claims 3
- 210000002889 endothelial cell Anatomy 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
- 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
- 206010061989 glomerulosclerosis Diseases 0.000 claims 3
- 201000001421 hyperglycemia Diseases 0.000 claims 3
- 230000001631 hypertensive effect Effects 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
- 229940039781 leptin Drugs 0.000 claims 3
- 201000009925 nephrosclerosis Diseases 0.000 claims 3
- 230000008289 pathophysiological mechanism Effects 0.000 claims 3
- 208000011580 syndromic disease Diseases 0.000 claims 3
- 229920001268 Cholestyramine Polymers 0.000 claims 2
- 229920002911 Colestipol Polymers 0.000 claims 2
- 208000030814 Eating disease Diseases 0.000 claims 2
- 208000019454 Feeding and Eating disease Diseases 0.000 claims 2
- 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 2
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims 2
- 108010028554 LDL Cholesterol Proteins 0.000 claims 2
- 208000017170 Lipid metabolism disease Diseases 0.000 claims 2
- 206010068871 Myotonic dystrophy Diseases 0.000 claims 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 108010069201 VLDL Cholesterol Proteins 0.000 claims 2
- 206010048214 Xanthoma Diseases 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-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
- GMRWGQCZJGVHKL-UHFFFAOYSA-N colestipol Chemical compound ClCC1CO1.NCCNCCNCCNCCN GMRWGQCZJGVHKL-UHFFFAOYSA-N 0.000 claims 2
- 229960002604 colestipol Drugs 0.000 claims 2
- 235000014632 disordered eating Nutrition 0.000 claims 2
- 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 2
- 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 2
- 229940125753 fibrate Drugs 0.000 claims 2
- 235000021588 free fatty acids Nutrition 0.000 claims 2
- 239000008103 glucose Substances 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims 2
- 230000002757 inflammatory effect Effects 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
- 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
- 229960003912 probucol Drugs 0.000 claims 2
- 239000011593 sulfur Chemical group 0.000 claims 2
- 150000003626 triacylglycerols Chemical class 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 229940118148 Aldose reductase inhibitor Drugs 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 206010018429 Glucose tolerance impaired Diseases 0.000 claims 1
- 239000003288 aldose reductase inhibitor Substances 0.000 claims 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical class [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims 1
- 229910052782 aluminium Chemical class 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
- 230000003920 cognitive function Effects 0.000 claims 1
- 230000018044 dehydration 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
- MNQZXJOMYWMBOU-UHFFFAOYSA-N glyceraldehyde Chemical compound OCC(O)C=O MNQZXJOMYWMBOU-UHFFFAOYSA-N 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 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 atom Chemical group O* 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 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 (https=) | 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 (https=) |
| JP (1) | JP2004534733A (https=) |
| CA (1) | CA2436741A1 (https=) |
| WO (1) | WO2002062799A1 (https=) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7041691B1 (en) | 1999-06-30 | 2006-05-09 | Amgen Inc. | Compounds for the modulation of PPARγ activity |
| US20030171399A1 (en) | 2000-06-28 | 2003-09-11 | Tularik Inc. | Quinolinyl and benzothiazolyl modulators |
| HN2002000317A (es) * | 2001-11-02 | 2003-05-21 | Pfizer | Inhibidores de pde9 para tratamiento de trastornos cardiovasculares |
| US7223761B2 (en) | 2003-10-03 | 2007-05-29 | Amgen Inc. | Salts and polymorphs of a potent antidiabetic compound |
| US20080125403A1 (en) | 2004-04-02 | 2008-05-29 | Merck & Co., Inc. | Method of Treating Men with Metabolic and Anthropometric Disorders |
| AU2005282572A1 (en) * | 2004-09-06 | 2006-03-16 | Dr. Reddy's Laboratories Ltd | Fibrate compounds having PPAR agonist activity |
| US7674822B2 (en) | 2004-11-24 | 2010-03-09 | Wyeth | PTP1b inhibitors |
| EP2527360B1 (en) | 2007-06-04 | 2015-10-28 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
| 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 |
| EP2810951B1 (en) | 2008-06-04 | 2017-03-15 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
| EP3241839B1 (en) | 2008-07-16 | 2019-09-04 | Bausch Health Ireland Limited | Agonists of guanylate cyclase useful for the treatment of gastrointestinal, inflammation, cancer and other disorders |
| WO2010047982A1 (en) | 2008-10-22 | 2010-04-29 | Merck Sharp & Dohme Corp. | Novel cyclic benzimidazole derivatives useful anti-diabetic agents |
| JP5557845B2 (ja) | 2008-10-31 | 2014-07-23 | メルク・シャープ・アンド・ドーム・コーポレーション | 糖尿病用剤として有用な新規環状ベンゾイミダゾール誘導体 |
| US8895596B2 (en) | 2010-02-25 | 2014-11-25 | Merck Sharp & Dohme Corp | Cyclic benzimidazole derivatives useful as anti-diabetic agents |
| US20130156720A1 (en) | 2010-08-27 | 2013-06-20 | 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 |
| BR112013021236B1 (pt) | 2011-02-25 | 2021-05-25 | Merck Sharp & Dohme Corp | composto derivado de benzimidazol, e, composição |
| WO2013082106A1 (en) | 2011-12-02 | 2013-06-06 | The General Hospital Corporation | Differentiation into brown adipocytes |
| US9527875B2 (en) | 2012-08-02 | 2016-12-27 | Merck Sharp & Dohme Corp. | Antidiabetic tricyclic compounds |
| RU2015140066A (ru) | 2013-02-22 | 2017-03-30 | Мерк Шарп И Доум Корп. | Противодиабетические бициклические соединения |
| WO2014139388A1 (en) | 2013-03-14 | 2014-09-18 | Merck Sharp & Dohme Corp. | Novel 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 |
| CA2905438A1 (en) | 2013-03-15 | 2014-09-25 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase and their uses |
| SI3004138T1 (sl) | 2013-06-05 | 2024-07-31 | Bausch Health Ireland Limited | Ultra čisti agonisti gvanilat ciklaze C, postopek za njihovo pripravo in uporabo |
| WO2015051496A1 (en) | 2013-10-08 | 2015-04-16 | Merck Sharp & Dohme Corp. | Antidiabetic tricyclic compounds |
| US11072602B2 (en) | 2016-12-06 | 2021-07-27 | Merck Sharp & Dohme Corp. | Antidiabetic heterocyclic compounds |
| WO2018118670A1 (en) | 2016-12-20 | 2018-06-28 | 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 |
| ATE286032T1 (de) * | 1998-04-23 | 2005-01-15 | Reddys Lab Ltd Dr | Heterozyklische verbindungen,und deren verwendung in arzneimittel,verfahren zu deren herstellung und diese enthaltende pharmazeutische zusammenstellungen |
-
2002
- 2002-02-05 CA CA002436741A patent/CA2436741A1/en not_active Abandoned
- 2002-02-05 EP EP02711126A patent/EP1363914A1/en not_active Withdrawn
- 2002-02-05 WO PCT/IB2002/000342 patent/WO2002062799A1/en not_active Ceased
- 2002-02-05 JP JP2002563152A patent/JP2004534733A/ja active Pending
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