CA2383946A1 - Pharmaceutical composition - Google Patents
Pharmaceutical composition Download PDFInfo
- Publication number
- CA2383946A1 CA2383946A1 CA002383946A CA2383946A CA2383946A1 CA 2383946 A1 CA2383946 A1 CA 2383946A1 CA 002383946 A CA002383946 A CA 002383946A CA 2383946 A CA2383946 A CA 2383946A CA 2383946 A1 CA2383946 A1 CA 2383946A1
- Authority
- CA
- Canada
- Prior art keywords
- group
- hydrogen atom
- lower alkyl
- formula
- 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.)
- Abandoned
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 72
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 506
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 372
- 150000001875 compounds Chemical class 0.000 claims abstract description 215
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 207
- 150000003839 salts Chemical class 0.000 claims abstract description 197
- 125000005843 halogen group Chemical group 0.000 claims abstract description 195
- 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 73
- 229940122355 Insulin sensitizer Drugs 0.000 claims abstract description 39
- 125000001041 indolyl group Chemical group 0.000 claims abstract description 16
- -1 phenylsulfonylamino group Chemical group 0.000 claims description 254
- 229910052717 sulfur Inorganic materials 0.000 claims description 200
- 229910052760 oxygen Inorganic materials 0.000 claims description 181
- 229910052757 nitrogen Inorganic materials 0.000 claims description 171
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 166
- 125000005842 heteroatom Chemical group 0.000 claims description 127
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 125
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 121
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 119
- 229910052736 halogen Inorganic materials 0.000 claims description 109
- 125000003277 amino group Chemical group 0.000 claims description 91
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 90
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 86
- 150000002367 halogens Chemical group 0.000 claims description 83
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 74
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 73
- 230000037396 body weight Effects 0.000 claims description 67
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 65
- 125000004432 carbon atom Chemical group C* 0.000 claims description 62
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 60
- 229910052799 carbon Inorganic materials 0.000 claims description 58
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 58
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 56
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 56
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 43
- 125000001624 naphthyl group Chemical group 0.000 claims description 33
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 31
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 30
- 125000003545 alkoxy group Chemical group 0.000 claims description 29
- HYAFETHFCAUJAY-UHFFFAOYSA-N pioglitazone Chemical compound N1=CC(CC)=CC=C1CCOC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 HYAFETHFCAUJAY-UHFFFAOYSA-N 0.000 claims description 29
- 125000002252 acyl group Chemical group 0.000 claims description 28
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 28
- 101100240522 Caenorhabditis elegans nhr-18 gene Proteins 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 27
- YASAKCUCGLMORW-UHFFFAOYSA-N Rosiglitazone Chemical compound C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O YASAKCUCGLMORW-UHFFFAOYSA-N 0.000 claims description 22
- 206010020772 Hypertension Diseases 0.000 claims description 21
- 125000001424 substituent group Chemical group 0.000 claims description 21
- 208000002249 Diabetes Complications Diseases 0.000 claims description 20
- 206010012655 Diabetic complications Diseases 0.000 claims description 20
- 208000008589 Obesity Diseases 0.000 claims description 20
- 235000020824 obesity Nutrition 0.000 claims description 20
- 208000011580 syndromic disease Diseases 0.000 claims description 20
- 125000001931 aliphatic group Chemical group 0.000 claims description 17
- 230000002401 inhibitory effect Effects 0.000 claims description 17
- 238000004519 manufacturing process Methods 0.000 claims description 15
- 239000000126 substance Substances 0.000 claims description 15
- WQUBEIMCFHCJCO-AWCRTANDSA-N 4-amino-n-{4-[2-(2,6-dimethyl-phenoxy)-acetylamino]-3-hydroxy-1-isobutyl-5-phenyl-pentyl}-benzamide Chemical compound C([C@@H]([C@@H](O)C[C@H](CC(C)C)NC(=O)C=1C=C(N)C=CC=1)NC(=O)COC=1C(=CC=CC=1C)C)C1=CC=CC=C1 WQUBEIMCFHCJCO-AWCRTANDSA-N 0.000 claims description 14
- 101100451196 Caenorhabditis elegans hizr-1 gene Proteins 0.000 claims description 14
- 208000002705 Glucose Intolerance Diseases 0.000 claims description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 14
- 208000031226 Hyperlipidaemia Diseases 0.000 claims description 14
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 14
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 14
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims description 14
- 125000004043 oxo group Chemical group O=* 0.000 claims description 14
- 229960005095 pioglitazone Drugs 0.000 claims description 14
- 201000009104 prediabetes syndrome Diseases 0.000 claims description 14
- 229910052705 radium Inorganic materials 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 12
- 210000001596 intra-abdominal fat Anatomy 0.000 claims description 11
- 229960004586 rosiglitazone Drugs 0.000 claims description 11
- 206010060378 Hyperinsulinaemia Diseases 0.000 claims description 10
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 10
- 230000003451 hyperinsulinaemic effect Effects 0.000 claims description 10
- 201000008980 hyperinsulinism Diseases 0.000 claims description 10
- 206010018364 Glomerulonephritis Diseases 0.000 claims description 9
- 241000282414 Homo sapiens Species 0.000 claims description 9
- 206010020710 Hyperphagia Diseases 0.000 claims description 9
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 9
- 241000124008 Mammalia Species 0.000 claims description 9
- 206010033645 Pancreatitis Diseases 0.000 claims description 9
- 208000004104 gestational diabetes Diseases 0.000 claims description 9
- 206010061989 glomerulosclerosis Diseases 0.000 claims description 9
- 230000001631 hypertensive effect Effects 0.000 claims description 9
- 208000010125 myocardial infarction Diseases 0.000 claims description 9
- 201000009925 nephrosclerosis Diseases 0.000 claims description 9
- 201000010065 polycystic ovary syndrome Diseases 0.000 claims description 9
- 238000002560 therapeutic procedure Methods 0.000 claims description 9
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 8
- 208000035473 Communicable disease Diseases 0.000 claims description 8
- 208000017442 Retinal disease Diseases 0.000 claims description 8
- 206010038923 Retinopathy Diseases 0.000 claims description 8
- 208000026106 cerebrovascular disease Diseases 0.000 claims description 8
- 208000015181 infectious disease Diseases 0.000 claims description 8
- 208000017169 kidney disease Diseases 0.000 claims description 8
- 201000001119 neuropathy Diseases 0.000 claims description 8
- 230000007823 neuropathy Effects 0.000 claims description 8
- 208000033808 peripheral neuropathy Diseases 0.000 claims description 8
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 8
- 206010002383 Angina Pectoris Diseases 0.000 claims description 7
- 206010012665 Diabetic gangrene Diseases 0.000 claims description 7
- 206010012669 Diabetic hyperosmolar coma Diseases 0.000 claims description 7
- 208000001132 Osteoporosis Diseases 0.000 claims description 7
- 208000005946 Xerostomia Diseases 0.000 claims description 7
- 206010013781 dry mouth Diseases 0.000 claims description 7
- 230000002093 peripheral effect Effects 0.000 claims description 7
- 230000000391 smoking effect Effects 0.000 claims description 7
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 7
- FHEYFIGWYQJVDR-ACJLOTCBSA-N 2-[[3-[(2r)-2-[[(2r)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1h-indol-7-yl]oxy]acetic acid Chemical compound C1([C@@H](O)CN[C@@H](CC=2C3=CC=CC(OCC(O)=O)=C3NC=2)C)=CC=CC(Cl)=C1 FHEYFIGWYQJVDR-ACJLOTCBSA-N 0.000 claims description 6
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 5
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 78
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 26
- MALIONKMKPITBV-UHFFFAOYSA-N 2-(3-chloro-4-hydroxyphenyl)-n-[2-(4-sulfamoylphenyl)ethyl]acetamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1CCNC(=O)CC1=CC=C(O)C(Cl)=C1 MALIONKMKPITBV-UHFFFAOYSA-N 0.000 claims 26
- RBIIKVXVYVANCQ-CUWPLCDZSA-N (2s,4s,5s)-5-amino-n-(3-amino-2,2-dimethyl-3-oxopropyl)-6-[4-(2-chlorophenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]-4-hydroxy-2-propan-2-ylhexanamide Chemical compound C1C(C)(C)N(C[C@H](N)[C@@H](O)C[C@@H](C(C)C)C(=O)NCC(C)(C)C(N)=O)CC(=O)N1C1=CC=CC=C1Cl RBIIKVXVYVANCQ-CUWPLCDZSA-N 0.000 claims 13
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 13
- RFEBDZANCVHDLP-UHFFFAOYSA-N 3-[(4-cyanophenyl)methylamino]-6-(trifluoromethyl)quinoxaline-2-carboxylic acid Chemical compound OC(=O)C1=NC2=CC=C(C(F)(F)F)C=C2N=C1NCC1=CC=C(C#N)C=C1 RFEBDZANCVHDLP-UHFFFAOYSA-N 0.000 claims 13
- 101100240528 Caenorhabditis elegans nhr-23 gene Proteins 0.000 claims 13
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 claims 13
- 239000003795 chemical substances by application Substances 0.000 abstract description 28
- 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 description 78
- 102000004877 Insulin Human genes 0.000 description 39
- 108090001061 Insulin Proteins 0.000 description 39
- 229940125396 insulin Drugs 0.000 description 39
- 239000004480 active ingredient Substances 0.000 description 27
- 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 description 26
- 239000008103 glucose Substances 0.000 description 26
- 238000002360 preparation method Methods 0.000 description 19
- 229940126062 Compound A Drugs 0.000 description 18
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 18
- 229940079593 drug Drugs 0.000 description 18
- 239000003814 drug Substances 0.000 description 18
- 210000002381 plasma Anatomy 0.000 description 17
- GHUUBYQTCDQWRA-UHFFFAOYSA-N Pioglitazone hydrochloride Chemical compound Cl.N1=CC(CC)=CC=C1CCOC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 GHUUBYQTCDQWRA-UHFFFAOYSA-N 0.000 description 16
- 229960002827 pioglitazone hydrochloride Drugs 0.000 description 16
- 230000000694 effects Effects 0.000 description 15
- 210000004369 blood Anatomy 0.000 description 14
- 239000008280 blood Substances 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
- 206010056997 Impaired fasting glucose Diseases 0.000 description 11
- 125000002723 alicyclic group Chemical group 0.000 description 11
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 11
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 10
- 241000700159 Rattus Species 0.000 description 10
- 239000003623 enhancer Substances 0.000 description 10
- 239000003112 inhibitor Substances 0.000 description 10
- 230000003914 insulin secretion Effects 0.000 description 10
- 229940123208 Biguanide Drugs 0.000 description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- 239000006186 oral dosage form Substances 0.000 description 9
- GXPHKUHSUJUWKP-UHFFFAOYSA-N troglitazone Chemical compound C1CC=2C(C)=C(O)C(C)=C(C)C=2OC1(C)COC(C=C1)=CC=C1CC1SC(=O)NC1=O GXPHKUHSUJUWKP-UHFFFAOYSA-N 0.000 description 9
- 229960001641 troglitazone Drugs 0.000 description 9
- GXPHKUHSUJUWKP-NTKDMRAZSA-N troglitazone Natural products C([C@@]1(OC=2C(C)=C(C(=C(C)C=2CC1)O)C)C)OC(C=C1)=CC=C1C[C@H]1SC(=O)NC1=O GXPHKUHSUJUWKP-NTKDMRAZSA-N 0.000 description 9
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 8
- 230000009471 action Effects 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 8
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 8
- 201000010099 disease Diseases 0.000 description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 8
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 description 7
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 7
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 description 7
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 7
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 7
- 238000007410 oral glucose tolerance test Methods 0.000 description 7
- 159000000000 sodium salts Chemical class 0.000 description 7
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 6
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- 229940100389 Sulfonylurea Drugs 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 6
- 125000000304 alkynyl group Chemical group 0.000 description 6
- 125000005110 aryl thio group Chemical group 0.000 description 6
- 229910052791 calcium Inorganic materials 0.000 description 6
- 239000011575 calcium Substances 0.000 description 6
- 229960005069 calcium Drugs 0.000 description 6
- OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 239000008101 lactose Substances 0.000 description 6
- 229920000609 methyl cellulose Polymers 0.000 description 6
- 239000001923 methylcellulose Substances 0.000 description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 5
- VJHCJDRQFCCTHL-UHFFFAOYSA-N acetic acid 2,3,4,5,6-pentahydroxyhexanal Chemical compound CC(O)=O.OCC(O)C(O)C(O)C(O)C=O VJHCJDRQFCCTHL-UHFFFAOYSA-N 0.000 description 5
- 125000004414 alkyl thio group Chemical group 0.000 description 5
- 150000004283 biguanides Chemical class 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 229950008138 carmellose Drugs 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 239000011737 fluorine Substances 0.000 description 5
- 125000002541 furyl group Chemical group 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 235000010355 mannitol Nutrition 0.000 description 5
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 description 5
- 229960003105 metformin Drugs 0.000 description 5
- 125000002971 oxazolyl group Chemical group 0.000 description 5
- 239000002504 physiological saline solution Substances 0.000 description 5
- 229940096701 plain lipid modifying drug hmg coa reductase inhibitors Drugs 0.000 description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
- 125000004076 pyridyl group Chemical group 0.000 description 5
- 125000000335 thiazolyl group Chemical group 0.000 description 5
- 125000001544 thienyl group Chemical group 0.000 description 5
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 4
- 108060003345 Adrenergic Receptor Proteins 0.000 description 4
- 102000017910 Adrenergic receptor Human genes 0.000 description 4
- XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 229920002472 Starch Polymers 0.000 description 4
- 229920001615 Tragacanth Polymers 0.000 description 4
- 125000004423 acyloxy group Chemical group 0.000 description 4
- 125000003302 alkenyloxy group Chemical group 0.000 description 4
- 239000007900 aqueous suspension Substances 0.000 description 4
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 4
- 125000004659 aryl alkyl thio group Chemical group 0.000 description 4
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 4
- 125000004104 aryloxy group Chemical group 0.000 description 4
- 239000000305 astragalus gummifer gum Substances 0.000 description 4
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- 125000001485 cycloalkadienyl group Chemical group 0.000 description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 description 4
- 125000000000 cycloalkoxy group Chemical group 0.000 description 4
- 206010061428 decreased appetite Diseases 0.000 description 4
- 239000002934 diuretic Substances 0.000 description 4
- 229940030606 diuretics Drugs 0.000 description 4
- 239000002552 dosage form Substances 0.000 description 4
- 230000001771 impaired effect Effects 0.000 description 4
- 208000027866 inflammatory disease Diseases 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 235000019359 magnesium stearate Nutrition 0.000 description 4
- 230000001404 mediated effect Effects 0.000 description 4
- 229960003365 mitiglinide Drugs 0.000 description 4
- OELFLUMRDSZNSF-BRWVUGGUSA-N nateglinide Chemical compound C1C[C@@H](C(C)C)CC[C@@H]1C(=O)N[C@@H](C(O)=O)CC1=CC=CC=C1 OELFLUMRDSZNSF-BRWVUGGUSA-N 0.000 description 4
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 229960004063 propylene glycol Drugs 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 241000894007 species Species 0.000 description 4
- 239000008107 starch Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
- A61K31/405—Indole-alkanecarboxylic acids; Derivatives thereof, e.g. tryptophan, indomethacin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
Landscapes
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Obesity (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11/250443 | 1999-09-03 | ||
| JP25044399 | 1999-09-03 | ||
| JP2000/56021 | 2000-02-28 | ||
| JP2000056021 | 2000-02-28 | ||
| PCT/JP2000/005951 WO2001017513A2 (en) | 1999-09-03 | 2000-09-01 | Pharmaceutical composition comprising an insulin sensitizer |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2383946A1 true CA2383946A1 (en) | 2001-03-15 |
Family
ID=26539777
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002383946A Abandoned CA2383946A1 (en) | 1999-09-03 | 2000-09-01 | Pharmaceutical composition |
Country Status (14)
| Country | Link |
|---|---|
| EP (1) | EP1212090A2 (ko) |
| KR (1) | KR20020063555A (ko) |
| CN (1) | CN1372476A (ko) |
| AR (1) | AR031674A1 (ko) |
| AU (1) | AU6868000A (ko) |
| CA (1) | CA2383946A1 (ko) |
| CO (1) | CO5180632A1 (ko) |
| HK (1) | HK1044711A1 (ko) |
| HU (1) | HUP0203285A3 (ko) |
| NO (1) | NO20021036L (ko) |
| PE (1) | PE20010580A1 (ko) |
| PL (1) | PL354295A1 (ko) |
| RU (1) | RU2002108346A (ko) |
| WO (1) | WO2001017513A2 (ko) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002051441A1 (fr) * | 2000-12-26 | 2002-07-04 | Sankyo Company, Limited | Compositions medicinales contenant un diuretique et un agent renforçant la resistance a l'insuline |
| WO2002080936A1 (en) | 2001-04-04 | 2002-10-17 | Ortho Mcneil Pharmaceutical, Inc. | Combination therapy comprising glucose reabsorption inhibitors and ppar modulators |
| DE60233655D1 (de) | 2001-04-04 | 2009-10-22 | Ortho Mcneil Janssen Pharm | R und retinoid x rezeptorenmodulatoren |
| FR2838968A1 (fr) * | 2002-04-30 | 2003-10-31 | Lipha | Association d'insuline et d'un derive de thiazolidinedione et son utilisation pour traiter le diabete |
| CA2488699A1 (en) * | 2002-06-12 | 2003-12-24 | Sumitomo Pharmaceuticals Co., Ltd. | Indole, indazole, and benzazole derivative |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04501722A (ja) * | 1988-11-14 | 1992-03-26 | ジ・アップジョン・カンパニー | 抗―糖尿病、抗―肥満症および抗―アテローム性動脈硬化症薬として有用なα―アミノ―インドール―３―酢酸 |
| AU651571B2 (en) * | 1990-02-09 | 1994-07-28 | Pharmacia & Upjohn Company | Use of insulin sensitizing agents to treat hypertension |
| DK0801059T3 (da) * | 1994-11-29 | 2001-09-24 | Dainippon Pharmaceutical Co | Indolderivat |
-
2000
- 2000-08-29 PE PE2000000887A patent/PE20010580A1/es not_active Application Discontinuation
- 2000-08-30 AR ARP000104514A patent/AR031674A1/es not_active Application Discontinuation
- 2000-09-01 PL PL00354295A patent/PL354295A1/xx not_active Application Discontinuation
- 2000-09-01 KR KR1020027002851A patent/KR20020063555A/ko not_active Application Discontinuation
- 2000-09-01 AU AU68680/00A patent/AU6868000A/en not_active Abandoned
- 2000-09-01 HU HU0203285A patent/HUP0203285A3/hu unknown
- 2000-09-01 RU RU2002108346/14A patent/RU2002108346A/ru not_active Application Discontinuation
- 2000-09-01 CO CO00065981A patent/CO5180632A1/es not_active Application Discontinuation
- 2000-09-01 CN CN00812420A patent/CN1372476A/zh active Pending
- 2000-09-01 WO PCT/JP2000/005951 patent/WO2001017513A2/en not_active Application Discontinuation
- 2000-09-01 CA CA002383946A patent/CA2383946A1/en not_active Abandoned
- 2000-09-01 EP EP00956872A patent/EP1212090A2/en not_active Withdrawn
-
2002
- 2002-03-01 NO NO20021036A patent/NO20021036L/no not_active Application Discontinuation
- 2002-08-15 HK HK02105969.4A patent/HK1044711A1/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO20021036D0 (no) | 2002-03-01 |
| KR20020063555A (ko) | 2002-08-03 |
| WO2001017513A3 (en) | 2001-09-20 |
| EP1212090A2 (en) | 2002-06-12 |
| AU6868000A (en) | 2001-04-10 |
| HK1044711A1 (zh) | 2002-11-01 |
| PE20010580A1 (es) | 2001-05-25 |
| WO2001017513A2 (en) | 2001-03-15 |
| AR031674A1 (es) | 2003-10-01 |
| NO20021036L (no) | 2002-04-26 |
| HUP0203285A3 (en) | 2003-02-28 |
| PL354295A1 (en) | 2004-01-12 |
| CO5180632A1 (es) | 2002-07-30 |
| RU2002108346A (ru) | 2003-11-20 |
| CN1372476A (zh) | 2002-10-02 |
| HUP0203285A2 (hu) | 2003-01-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |