JP2005523300A5 - - Google Patents
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- Publication number
- JP2005523300A5 JP2005523300A5 JP2003576430A JP2003576430A JP2005523300A5 JP 2005523300 A5 JP2005523300 A5 JP 2005523300A5 JP 2003576430 A JP2003576430 A JP 2003576430A JP 2003576430 A JP2003576430 A JP 2003576430A JP 2005523300 A5 JP2005523300 A5 JP 2005523300A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- dihydroquinazolin
- thiazolidine
- oxo
- methoxy
- 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
Links
- 239000000203 mixture Substances 0.000 claims 26
- 238000000034 method Methods 0.000 claims 17
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 9
- WIMXIELKVIGBNM-UHFFFAOYSA-N 5-[[4-[(3-methyl-4-oxoquinazolin-2-yl)methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione;potassium Chemical compound [K].N=1C2=CC=CC=C2C(=O)N(C)C=1COC(C=C1)=CC=C1CC1SC(=O)NC1=O WIMXIELKVIGBNM-UHFFFAOYSA-N 0.000 claims 8
- 239000008194 pharmaceutical composition Substances 0.000 claims 8
- 239000000243 solution Substances 0.000 claims 8
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 8
- 206010022489 Insulin Resistance Diseases 0.000 claims 6
- 208000035475 disorder Diseases 0.000 claims 6
- 239000003960 organic solvent Substances 0.000 claims 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 5
- IETKPTYAGKZLKY-UHFFFAOYSA-N 5-[[4-[(3-methyl-4-oxoquinazolin-2-yl)methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound N=1C2=CC=CC=C2C(=O)N(C)C=1COC(C=C1)=CC=C1CC1SC(=O)NC1=O IETKPTYAGKZLKY-UHFFFAOYSA-N 0.000 claims 4
- 201000001320 Atherosclerosis Diseases 0.000 claims 4
- 208000002705 Glucose Intolerance Diseases 0.000 claims 4
- 208000031226 Hyperlipidaemia Diseases 0.000 claims 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 4
- 208000008589 Obesity Diseases 0.000 claims 4
- 208000001132 Osteoporosis Diseases 0.000 claims 4
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims 4
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims 4
- 235000020824 obesity Nutrition 0.000 claims 4
- 201000010065 polycystic ovary syndrome Diseases 0.000 claims 4
- 238000002360 preparation method Methods 0.000 claims 4
- 230000002265 prevention Effects 0.000 claims 4
- 239000011541 reaction mixture Substances 0.000 claims 4
- 238000003756 stirring Methods 0.000 claims 4
- 239000008096 xylene Substances 0.000 claims 4
- ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 claims 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- 206010020772 Hypertension Diseases 0.000 claims 3
- 102000016267 Leptin Human genes 0.000 claims 3
- 108010092277 Leptin Proteins 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 229940079593 drug Drugs 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 238000001914 filtration Methods 0.000 claims 3
- 208000017169 kidney 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
- 229940039781 leptin Drugs 0.000 claims 3
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims 3
- NIGXDLPSDCSMNR-UHFFFAOYSA-N potassium;1,3-thiazolidine-2,4-dione Chemical compound [K].O=C1CSC(=O)N1 NIGXDLPSDCSMNR-UHFFFAOYSA-N 0.000 claims 3
- 201000009104 prediabetes syndrome Diseases 0.000 claims 3
- 239000013049 sediment Substances 0.000 claims 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 2
- 206010003210 Arteriosclerosis Diseases 0.000 claims 2
- 229940123208 Biguanide Drugs 0.000 claims 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims 2
- 206010012289 Dementia Diseases 0.000 claims 2
- 208000002249 Diabetes Complications Diseases 0.000 claims 2
- 206010012655 Diabetic complications Diseases 0.000 claims 2
- 208000032928 Dyslipidaemia Diseases 0.000 claims 2
- 206010018364 Glomerulonephritis 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
- 208000035150 Hypercholesterolemia Diseases 0.000 claims 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 2
- 102000004877 Insulin Human genes 0.000 claims 2
- 108090001061 Insulin Proteins 0.000 claims 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- 208000017170 Lipid metabolism disease Diseases 0.000 claims 2
- 102000004895 Lipoproteins Human genes 0.000 claims 2
- 108090001030 Lipoproteins Proteins 0.000 claims 2
- 206010068871 Myotonic dystrophy Diseases 0.000 claims 2
- 206010029164 Nephrotic syndrome Diseases 0.000 claims 2
- 206010033645 Pancreatitis Diseases 0.000 claims 2
- 201000004681 Psoriasis Diseases 0.000 claims 2
- 208000017442 Retinal disease Diseases 0.000 claims 2
- 206010038923 Retinopathy Diseases 0.000 claims 2
- 229940100389 Sulfonylurea Drugs 0.000 claims 2
- 229940123464 Thiazolidinedione Drugs 0.000 claims 2
- 206010048214 Xanthoma Diseases 0.000 claims 2
- 206010048215 Xanthomatosis Diseases 0.000 claims 2
- 239000003472 antidiabetic agent Substances 0.000 claims 2
- 208000011775 arteriosclerosis disease Diseases 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
- 230000037396 body weight Effects 0.000 claims 2
- 230000020411 cell activation Effects 0.000 claims 2
- 235000012000 cholesterol Nutrition 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 208000029078 coronary artery disease Diseases 0.000 claims 2
- 239000013078 crystal Substances 0.000 claims 2
- 210000002889 endothelial cell Anatomy 0.000 claims 2
- 229940125753 fibrate Drugs 0.000 claims 2
- 235000021588 free fatty acids Nutrition 0.000 claims 2
- 206010061989 glomerulosclerosis Diseases 0.000 claims 2
- 239000008103 glucose Substances 0.000 claims 2
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims 2
- 201000001421 hyperglycemia Diseases 0.000 claims 2
- 229940125396 insulin Drugs 0.000 claims 2
- 230000008289 pathophysiological mechanism Effects 0.000 claims 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 claims 2
- 238000000634 powder X-ray diffraction Methods 0.000 claims 2
- 239000002244 precipitate Substances 0.000 claims 2
- 208000011580 syndromic disease Diseases 0.000 claims 2
- 230000002194 synthesizing effect Effects 0.000 claims 2
- 150000003626 triacylglycerols Chemical class 0.000 claims 2
- XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 claims 1
- 241001640117 Callaeum Species 0.000 claims 1
- 229940122502 Cholesterol absorption inhibitor Drugs 0.000 claims 1
- 206010018429 Glucose tolerance impaired Diseases 0.000 claims 1
- 206010055171 Hypertensive nephropathy Diseases 0.000 claims 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims 1
- 101150014691 PPARA gene Proteins 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 239000000556 agonist Substances 0.000 claims 1
- 230000003579 anti-obesity Effects 0.000 claims 1
- 239000000883 anti-obesity agent Substances 0.000 claims 1
- 229940125710 antiobesity agent Drugs 0.000 claims 1
- 150000004283 biguanides Chemical class 0.000 claims 1
- 239000002775 capsule Substances 0.000 claims 1
- 230000001906 cholesterol absorption Effects 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 229940125542 dual agonist Drugs 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 230000001631 hypertensive effect Effects 0.000 claims 1
- 229940126904 hypoglycaemic agent Drugs 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 210000003734 kidney Anatomy 0.000 claims 1
- 201000009925 nephrosclerosis Diseases 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 229940096701 plain lipid modifying drug hmg coa reductase inhibitors Drugs 0.000 claims 1
- 239000000843 powder Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
- 230000002195 synergetic effect Effects 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
- 150000001467 thiazolidinediones Chemical class 0.000 claims 1
- IETKPTYAGKZLKY-UHFFFAOYSA-M CN(C(COc1ccc(CC(C([N-]2)=O)SC2=O)cc1)=Nc1ccccc11)C1=O Chemical compound CN(C(COc1ccc(CC(C([N-]2)=O)SC2=O)cc1)=Nc1ccccc11)C1=O IETKPTYAGKZLKY-UHFFFAOYSA-M 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN180MA2002 | 2002-03-15 | ||
| PCT/IB2003/000935 WO2003078425A1 (en) | 2002-03-15 | 2003-03-14 | Novel crystalline form of 5-[4-[[3-methyl-4-oxo-3,4-dihydroquinazolin-2-yl]methoxy]benzyl]thiazolidine-2,4-dione potassium salt |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010171223A Division JP2010248246A (ja) | 2002-03-15 | 2010-07-29 | ５−［４−［［３−メチル−４−オキソ−３，４−ジヒドロキナゾリン−２−イル］メトキシ］ベンジル］チアゾリジン−２，４−ジオンカリウム塩の新規な結晶形 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005523300A JP2005523300A (ja) | 2005-08-04 |
| JP2005523300A5 true JP2005523300A5 (enExample) | 2006-04-20 |
| JP4634716B2 JP4634716B2 (ja) | 2011-02-16 |
Family
ID=33397665
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003576430A Expired - Fee Related JP4634716B2 (ja) | 2002-03-15 | 2003-03-14 | ５−［４−［［３−メチル−４−オキソ−３，４−ジヒドロキナゾリン−２−イル］メトキシ］ベンジル］チアゾリジン−２，４−ジオンカリウム塩の新規な結晶形 |
| JP2010171223A Withdrawn JP2010248246A (ja) | 2002-03-15 | 2010-07-29 | ５−［４−［［３−メチル−４−オキソ−３，４−ジヒドロキナゾリン−２−イル］メトキシ］ベンジル］チアゾリジン−２，４−ジオンカリウム塩の新規な結晶形 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010171223A Withdrawn JP2010248246A (ja) | 2002-03-15 | 2010-07-29 | ５−［４−［［３−メチル−４−オキソ−３，４−ジヒドロキナゾリン−２−イル］メトキシ］ベンジル］チアゾリジン−２，４−ジオンカリウム塩の新規な結晶形 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US8377950B2 (enExample) |
| EP (2) | EP1623984B1 (enExample) |
| JP (2) | JP4634716B2 (enExample) |
| AT (1) | ATE531713T1 (enExample) |
| AU (1) | AU2003209562A1 (enExample) |
| ES (1) | ES2373446T3 (enExample) |
| WO (1) | WO2003078425A1 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UY30755A1 (es) | 2006-12-04 | 2008-07-31 | Bayer Schering Pharma Ag | Sal de potasio cristalina de analogos de lipoxina a4 |
| US7985859B2 (en) * | 2007-05-30 | 2011-07-26 | Wockhardt Ltd. | Processes for the preparation of clopidogrel |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HUP0301101A3 (en) * | 1996-12-31 | 2009-03-30 | Reddy S Res Foundation | Novel heterocyclic compounds process for their preparation and pharmaceutical compositions containing them and their use in the treatment of diabetes and related diseases |
| IN187716B (enExample) * | 1998-09-14 | 2002-06-15 | Reddy Research Foundation |
-
2003
- 2003-03-14 AT AT05077388T patent/ATE531713T1/de active
- 2003-03-14 JP JP2003576430A patent/JP4634716B2/ja not_active Expired - Fee Related
- 2003-03-14 US US10/507,399 patent/US8377950B2/en not_active Expired - Fee Related
- 2003-03-14 ES ES05077388T patent/ES2373446T3/es not_active Expired - Lifetime
- 2003-03-14 EP EP05077388A patent/EP1623984B1/en not_active Expired - Lifetime
- 2003-03-14 EP EP03744465A patent/EP1487830A1/en not_active Ceased
- 2003-03-14 WO PCT/IB2003/000935 patent/WO2003078425A1/en not_active Ceased
- 2003-03-14 AU AU2003209562A patent/AU2003209562A1/en not_active Abandoned
-
2010
- 2010-07-29 JP JP2010171223A patent/JP2010248246A/ja not_active Withdrawn
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