SK3792003A3 - A thiazolidinedione derivative and its use as antidiabetic - Google Patents

A thiazolidinedione derivative and its use as antidiabetic Download PDF

Info

Publication number: SK3792003A3
Authority: SK; Slovakia
Prior art keywords: pyridyl; ethoxy; methyl; dione; amino
Prior art date: 2000-09-29

Application number

SK379-2003A

Other languages

English (en)

Slovak (sk)

Inventor

Michael Millan

Original Assignee

Smithkline Beecham Plc

Priority date (The priority date 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 date listed.)

2000-09-29

Filing date

2001-09-28

Publication date

2004-04-06

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=9900427&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=SK3792003(A3) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

2001-09-28 Application filed by Smithkline Beecham Plc filed Critical Smithkline Beecham Plc

2004-04-06 Publication of SK3792003A3 publication Critical patent/SK3792003A3/sk

Links

239000003472 antidiabetic agent Substances 0.000 title claims description 12
150000001467 thiazolidinediones Chemical class 0.000 title description 2
230000003178 anti-diabetic effect Effects 0.000 title 1
239000012453 solvate Substances 0.000 claims abstract description 48
206010012601 diabetes mellitus Diseases 0.000 claims abstract description 28
238000011282 treatment Methods 0.000 claims abstract description 17
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 14
239000003814 drug Substances 0.000 claims abstract description 11
LZLOZFXJQSWMMB-UHFFFAOYSA-N 5-[[4-[2-[methyl(pyridin-2-yl)amino]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione;potassium Chemical compound [K].C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O LZLOZFXJQSWMMB-UHFFFAOYSA-N 0.000 claims abstract description 7
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 68
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 23
239000007787 solid Substances 0.000 claims description 20
238000000034 method Methods 0.000 claims description 16
238000000634 powder X-ray diffraction Methods 0.000 claims description 12
229940125708 antidiabetic agent Drugs 0.000 claims description 11
238000011321 prophylaxis Methods 0.000 claims description 11
150000003839 salts Chemical class 0.000 claims description 9
238000001237 Raman spectrum Methods 0.000 claims description 7
239000003937 drug carrier Substances 0.000 claims description 7
238000002329 infrared spectrum Methods 0.000 claims description 7
241000124008 Mammalia Species 0.000 claims description 6
238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 claims description 6
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 6
231100000252 nontoxic Toxicity 0.000 claims description 4
230000003000 nontoxic effect Effects 0.000 claims description 4
-1 N-methyl-N- (2-pyridyl) amino Chemical group 0.000 claims description 3
159000000001 potassium salts Chemical class 0.000 claims description 3
239000013543 active substance Substances 0.000 claims 1
150000001875 compounds Chemical class 0.000 abstract description 36
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 24
239000000203 mixture Substances 0.000 description 17
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
239000000243 solution Substances 0.000 description 11
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
239000002904 solvent Substances 0.000 description 9
239000000047 product Substances 0.000 description 8
239000000725 suspension Substances 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
239000004480 active ingredient Substances 0.000 description 7
239000011230 binding agent Substances 0.000 description 7
238000010992 reflux Methods 0.000 description 7
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 description 5
208000001072 type 2 diabetes mellitus Diseases 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
235000019441 ethanol Nutrition 0.000 description 4
239000007788 liquid Substances 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
206010022489 Insulin Resistance Diseases 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
229940079593 drug Drugs 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
239000000945 filler Substances 0.000 description 3
238000011049 filling Methods 0.000 description 3
238000004128 high performance liquid chromatography Methods 0.000 description 3
239000000463 material Substances 0.000 description 3
238000002156 mixing Methods 0.000 description 3
229910001414 potassium ion Inorganic materials 0.000 description 3
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
239000000843 powder Substances 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000012258 stirred mixture Substances 0.000 description 3
239000003826 tablet Substances 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
239000000080 wetting agent Substances 0.000 description 3
229940077274 Alpha glucosidase inhibitor Drugs 0.000 description 2
229940123208 Biguanide Drugs 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
206010020772 Hypertension Diseases 0.000 description 2
208000008589 Obesity Diseases 0.000 description 2
238000001069 Raman spectroscopy Methods 0.000 description 2
229940100389 Sulfonylurea Drugs 0.000 description 2
MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
239000000654 additive Substances 0.000 description 2
239000003888 alpha glucosidase inhibitor Substances 0.000 description 2
239000002775 capsule Substances 0.000 description 2
230000015556 catabolic process Effects 0.000 description 2
239000007810 chemical reaction solvent Substances 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
239000003086 colorant Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000006731 degradation reaction Methods 0.000 description 2
238000000113 differential scanning calorimetry Methods 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
239000007884 disintegrant Substances 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
238000000227 grinding Methods 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
208000017169 kidney disease Diseases 0.000 description 2
239000000314 lubricant Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
238000010899 nucleation Methods 0.000 description 2
235000020824 obesity Nutrition 0.000 description 2
238000007911 parenteral administration Methods 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
239000003755 preservative agent Substances 0.000 description 2
238000001228 spectrum Methods 0.000 description 2
239000006188 syrup Substances 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 description 1
IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
235000019489 Almond oil Nutrition 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
208000000103 Anorexia Nervosa Diseases 0.000 description 1
201000001320 Atherosclerosis Diseases 0.000 description 1
XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical group NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 description 1
208000032841 Bulimia Diseases 0.000 description 1
206010006550 Bulimia nervosa Diseases 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
208000024172 Cardiovascular disease Diseases 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
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 1
208000002249 Diabetes Complications Diseases 0.000 description 1
239000004097 EU approved flavor enhancer Substances 0.000 description 1
208000030814 Eating disease Diseases 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
238000005079 FT-Raman Methods 0.000 description 1
208000019454 Feeding and Eating disease Diseases 0.000 description 1
238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
206010018364 Glomerulonephritis Diseases 0.000 description 1
208000002705 Glucose Intolerance Diseases 0.000 description 1
239000004471 Glycine Substances 0.000 description 1
238000010268 HPLC based assay Methods 0.000 description 1
239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
206010060378 Hyperinsulinaemia Diseases 0.000 description 1
229920004459 Kel-F® PCTFE Polymers 0.000 description 1
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 1
235000010643 Leucaena leucocephala Nutrition 0.000 description 1
240000007472 Leucaena leucocephala Species 0.000 description 1
208000002720 Malnutrition Diseases 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
229920000881 Modified starch Polymers 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
206010029164 Nephrotic syndrome Diseases 0.000 description 1
206010036049 Polycystic ovaries Diseases 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
208000034189 Sclerosis Diseases 0.000 description 1
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical group [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
238000000862 absorption spectrum Methods 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
239000008168 almond oil Substances 0.000 description 1
CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical compound [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 description 1
229940063655 aluminum stearate Drugs 0.000 description 1
208000022531 anorexia Diseases 0.000 description 1
150000004283 biguanides Chemical class 0.000 description 1
239000006172 buffering agent Substances 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
150000007942 carboxylates Chemical group 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical compound FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 description 1
208000020832 chronic kidney disease Diseases 0.000 description 1
238000011260 co-administration Methods 0.000 description 1
239000003240 coconut oil Substances 0.000 description 1
235000019864 coconut oil Nutrition 0.000 description 1
239000002131 composite material Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000013256 coordination polymer Substances 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
206010061428 decreased appetite Diseases 0.000 description 1
239000007857 degradation product Substances 0.000 description 1
230000008021 deposition Effects 0.000 description 1
238000011161 development Methods 0.000 description 1
230000001079 digestive effect Effects 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
235000014632 disordered eating Nutrition 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000008157 edible vegetable oil Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
208000028208 end stage renal disease Diseases 0.000 description 1
201000000523 end stage renal failure Diseases 0.000 description 1
BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
230000005284 excitation Effects 0.000 description 1
239000003925 fat Substances 0.000 description 1
235000019197 fats Nutrition 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000019264 food flavour enhancer Nutrition 0.000 description 1
230000037406 food intake Effects 0.000 description 1
235000012631 food intake Nutrition 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000000499 gel Substances 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
208000004104 gestational diabetes Diseases 0.000 description 1
239000011521 glass Substances 0.000 description 1
150000002314 glycerols Chemical class 0.000 description 1
239000008187 granular material Substances 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
230000000055 hyoplipidemic effect Effects 0.000 description 1
201000001421 hyperglycemia Diseases 0.000 description 1
230000003451 hyperinsulinaemic effect Effects 0.000 description 1
201000008980 hyperinsulinism Diseases 0.000 description 1
230000001631 hypertensive effect Effects 0.000 description 1
230000002218 hypoglycaemic effect Effects 0.000 description 1
239000003978 infusion fluid Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
239000008101 lactose Substances 0.000 description 1
235000010445 lecithin Nutrition 0.000 description 1
239000000787 lecithin Substances 0.000 description 1
229940067606 lecithin Drugs 0.000 description 1
239000003589 local anesthetic agent Substances 0.000 description 1
229960005015 local anesthetics Drugs 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
238000000449 magic angle spinning nuclear magnetic resonance spectrum Methods 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
230000001071 malnutrition Effects 0.000 description 1
235000000824 malnutrition Nutrition 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
238000003801 milling Methods 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
235000019426 modified starch Nutrition 0.000 description 1
238000012544 monitoring process Methods 0.000 description 1
WSMQHVVQUCUUBN-NIRMZGPJSA-N n-(4-aminophenyl)sulfonyl-n-(3,4-dimethyl-1,2-oxazol-5-yl)acetamide;4-o-[(2r,3s,4r,6s)-4-(dimethylamino)-2-[[(3r,4s,5s,6r,7r,9r,11r,12r,13s,14r)-14-ethyl-7,12,13-trihydroxy-4-[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,7,9,11,13-hexam Chemical compound C=1C=C(N)C=CC=1S(=O)(=O)N(C(=O)C)C=1ON=C(C)C=1C.O1[C@@H](C)C[C@@H](N(C)C)[C@H](OC(=O)CCC(=O)OCC)[C@H]1O[C@H]1[C@@](O)(C)C[C@@H](C)C(=O)[C@H](C)[C@@H](O)[C@](C)(O)[C@@H](CC)OC(=O)[C@H](C)[C@@H](O[C@@H]2O[C@@H](C)[C@H](O)[C@](C)(OC)C2)[C@@H]1C WSMQHVVQUCUUBN-NIRMZGPJSA-N 0.000 description 1
201000009925 nephrosclerosis Diseases 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
208000015380 nutritional deficiency disease Diseases 0.000 description 1
239000003182 parenteral nutrition solution Substances 0.000 description 1
239000008024 pharmaceutical diluent Substances 0.000 description 1
201000010065 polycystic ovary syndrome Diseases 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
LTUDISCZKZHRMJ-UHFFFAOYSA-N potassium;hydrate Chemical class O.[K] LTUDISCZKZHRMJ-UHFFFAOYSA-N 0.000 description 1
201000009104 prediabetes syndrome Diseases 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
238000012545 processing Methods 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000003893 regulation of appetite Effects 0.000 description 1
YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
238000007789 sealing Methods 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
229920003109 sodium starch glycolate Polymers 0.000 description 1
239000008109 sodium starch glycolate Substances 0.000 description 1
229940079832 sodium starch glycolate Drugs 0.000 description 1
239000007909 solid dosage form Substances 0.000 description 1
239000012265 solid product Substances 0.000 description 1
238000000371 solid-state nuclear magnetic resonance spectroscopy Methods 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
239000001593 sorbitan monooleate Substances 0.000 description 1
235000011069 sorbitan monooleate Nutrition 0.000 description 1
229940035049 sorbitan monooleate Drugs 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
235000010356 sorbitol Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
229940032147 starch Drugs 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
150000003431 steroids Chemical class 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000003860 storage Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
238000012360 testing method Methods 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000002076 thermal analysis method Methods 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
230000002110 toxicologic effect Effects 0.000 description 1
231100000027 toxicology Toxicity 0.000 description 1
238000001622 two pulse phase modulation pulse sequence Methods 0.000 description 1
238000009827 uniform distribution Methods 0.000 description 1
230000000007 visual effect Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- 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
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Diabetes (AREA)
Public Health (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Obesity (AREA)
Hematology (AREA)
Endocrinology (AREA)
Emergency Medicine (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

SK379-2003A 2000-09-29 2001-09-28 A thiazolidinedione derivative and its use as antidiabetic SK3792003A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GBGB0023970.7A GB0023970D0 (en)	2000-09-29	2000-09-29	Novel pharmaceutical
PCT/GB2001/004346 WO2002026736A1 (en)	2000-09-29	2001-09-28	A thiazolidinedione derivative and its use as antidiabetic

Publications (1)

Publication Number	Publication Date
SK3792003A3 true SK3792003A3 (en)	2004-04-06

Family

ID=9900427

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK379-2003A SK3792003A3 (en)	2000-09-29	2001-09-28	A thiazolidinedione derivative and its use as antidiabetic

Country Status (33)

Country	Link
US (1)	US20040038968A1 (de)
EP (2)	EP1325000B1 (de)
JP (1)	JP2004509960A (de)
KR (2)	KR100822135B1 (de)
CN (2)	CN1620453B (de)
AP (1)	AP1841A (de)
AT (1)	ATE368038T1 (de)
AU (2)	AU9203401A (de)
BG (1)	BG107678A (de)
BR (1)	BR0114364A (de)
CA (1)	CA2423978A1 (de)
CY (1)	CY1107767T1 (de)
CZ (1)	CZ2003849A3 (de)
DE (1)	DE60129576T2 (de)
DK (1)	DK1325000T3 (de)
DZ (1)	DZ3481A1 (de)
EA (1)	EA005110B1 (de)
EC (1)	ECSP034529A (de)
ES (1)	ES2290169T3 (de)
GB (1)	GB0023970D0 (de)
HU (1)	HUP0301199A3 (de)
IL (2)	IL155140A0 (de)
MA (1)	MA25913A1 (de)
MX (1)	MXPA03002867A (de)
NO (2)	NO324970B1 (de)
NZ (1)	NZ524932A (de)
OA (1)	OA12400A (de)
PL (1)	PL361157A1 (de)
PT (1)	PT1325000E (de)
SK (1)	SK3792003A3 (de)
UA (1)	UA76121C2 (de)
WO (1)	WO2002026736A1 (de)
ZA (1)	ZA200302438B (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HU225919B1 (en) *	1999-12-18	2007-12-28	Richter Gedeon Nyrt	Thiazolidine-derivatives, process for their preparation pharmaceutical and intermediates
HUP0800755A2 (en)	2008-12-11	2010-09-28	Richter Gedeon Nyrt	Crystalline forms of rosiglitazone

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0842925A1 (de) *	1987-09-04	1998-05-20	Beecham Group Plc	Substituierte Thiazolidindionderivate
US5646169A (en) *	1987-09-04	1997-07-08	Beecham Group P.L.C.	Compounds for treating eating disorders in which blood glucose levels are raised
GB9124513D0 (en) *	1991-11-19	1992-01-08	Smithkline Beecham Plc	Novel process
GB9308487D0 (en) *	1993-04-23	1993-06-09	Smithkline Beecham Plc	Novel compounds
GB9712866D0 (en) *	1997-06-18	1997-08-20	Smithkline Beecham Plc	Novel method of treatment
GB9723295D0 (en) *	1997-11-04	1998-01-07	Smithkline Beecham Plc	Novel process
CN1183130C (zh) *	1999-09-24	2005-01-05	中国人民解放军军事医学科学院毒物药物研究所	噻唑烷类衍生物及其医药用途
HU225919B1 (en) *	1999-12-18	2007-12-28	Richter Gedeon Nyrt	Thiazolidine-derivatives, process for their preparation pharmaceutical and intermediates

2000
- 2000-09-29 GB GBGB0023970.7A patent/GB0023970D0/en not_active Ceased
2001
- 2001-09-28 DZ DZ013481A patent/DZ3481A1/fr active
- 2001-09-28 EA EA200300423A patent/EA005110B1/ru not_active IP Right Cessation
- 2001-09-28 EP EP01972254A patent/EP1325000B1/de not_active Revoked
- 2001-09-28 JP JP2002531120A patent/JP2004509960A/ja active Pending
- 2001-09-28 BR BR0114364-6A patent/BR0114364A/pt not_active Application Discontinuation
- 2001-09-28 MX MXPA03002867A patent/MXPA03002867A/es active IP Right Grant
- 2001-09-28 CA CA002423978A patent/CA2423978A1/en not_active Abandoned
- 2001-09-28 AT AT01972254T patent/ATE368038T1/de active
- 2001-09-28 KR KR1020037004496A patent/KR100822135B1/ko not_active Expired - Fee Related
- 2001-09-28 AP APAP/P/2003/002766A patent/AP1841A/en active
- 2001-09-28 AU AU9203401A patent/AU9203401A/xx active Pending
- 2001-09-28 CN CN01816563XA patent/CN1620453B/zh not_active Expired - Fee Related
- 2001-09-28 EP EP07105370A patent/EP1795531A1/de not_active Withdrawn
- 2001-09-28 HU HU0301199A patent/HUP0301199A3/hu unknown
- 2001-09-28 IL IL15514001A patent/IL155140A0/xx unknown
- 2001-09-28 WO PCT/GB2001/004346 patent/WO2002026736A1/en not_active Ceased
- 2001-09-28 KR KR1020077018614A patent/KR20070089258A/ko not_active Ceased
- 2001-09-28 AU AU2001292034A patent/AU2001292034B2/en not_active Ceased
- 2001-09-28 ES ES01972254T patent/ES2290169T3/es not_active Expired - Lifetime
- 2001-09-28 DE DE60129576T patent/DE60129576T2/de not_active Expired - Lifetime
- 2001-09-28 PL PL36115701A patent/PL361157A1/xx not_active Application Discontinuation
- 2001-09-28 UA UA2003032736A patent/UA76121C2/uk unknown
- 2001-09-28 CN CN2010100046806A patent/CN101961333A/zh active Pending
- 2001-09-28 CZ CZ2003849A patent/CZ2003849A3/cs unknown
- 2001-09-28 NZ NZ524932A patent/NZ524932A/en unknown
- 2001-09-28 PT PT01972254T patent/PT1325000E/pt unknown
- 2001-09-28 OA OA1200300091A patent/OA12400A/en unknown
- 2001-09-28 US US10/381,497 patent/US20040038968A1/en not_active Abandoned
- 2001-09-28 DK DK01972254T patent/DK1325000T3/da active
- 2001-09-28 SK SK379-2003A patent/SK3792003A3/sk not_active Application Discontinuation
2003
- 2003-03-26 BG BG107678A patent/BG107678A/bg unknown
- 2003-03-27 IL IL155140A patent/IL155140A/en not_active IP Right Cessation
- 2003-03-28 MA MA27077A patent/MA25913A1/fr unknown
- 2003-03-28 NO NO20031434A patent/NO324970B1/no not_active IP Right Cessation
- 2003-03-28 ZA ZA200302438A patent/ZA200302438B/en unknown
- 2003-03-28 EC EC2003004529A patent/ECSP034529A/es unknown
2007
- 2007-10-16 CY CY20071101336T patent/CY1107767T1/el unknown
- 2007-10-31 NO NO20075507A patent/NO20075507L/no unknown

Also Published As

Publication number	Publication date
CN1620453B (zh)	2010-12-08
JP2004509960A (ja)	2004-04-02
EP1325000B1 (de)	2007-07-25
BR0114364A (pt)	2003-12-09
PT1325000E (pt)	2007-10-25
CN1620453A (zh)	2005-05-25
US20040038968A1 (en)	2004-02-26
KR100822135B1 (ko)	2008-04-15
DE60129576T2 (de)	2008-04-17
IL155140A0 (en)	2003-10-31
CA2423978A1 (en)	2002-04-04
ZA200302438B (en)	2004-04-28
NO20031434L (no)	2003-05-27
ATE368038T1 (de)	2007-08-15
DZ3481A1 (fr)	2002-04-04
AP2003002766A0 (en)	2003-03-31
DK1325000T3 (da)	2007-11-12
PL361157A1 (en)	2004-09-20
UA76121C2 (en)	2006-07-17
EP1795531A1 (de)	2007-06-13
EP1325000A1 (de)	2003-07-09
AP1841A (en)	2008-04-30
OA12400A (en)	2004-09-06
MXPA03002867A (es)	2004-12-06
BG107678A (bg)	2003-11-28
AU9203401A (en)	2002-04-08
HUP0301199A2 (hu)	2003-11-28
AU2001292034B2 (en)	2005-04-21
CY1107767T1 (el)	2013-04-18
EA005110B1 (ru)	2004-10-28
IL155140A (en)	2010-06-30
KR20030032058A (ko)	2003-04-23
HUP0301199A3 (en)	2005-04-28
EA200300423A1 (ru)	2003-08-28
ECSP034529A (es)	2003-05-26
GB0023970D0 (en)	2000-11-15
CZ2003849A3 (cs)	2004-03-17
ES2290169T3 (es)	2008-02-16
MA25913A1 (fr)	2003-10-01
NO20075507L (no)	2003-05-27
WO2002026736A1 (en)	2002-04-04
KR20070089258A (ko)	2007-08-30
DE60129576D1 (de)	2007-09-06
HK1058192A1 (en)	2004-05-07
NO324970B1 (no)	2008-01-14
NO20031434D0 (no)	2003-03-28
NZ524932A (en)	2005-06-24
CN101961333A (zh)	2011-02-02

Legal Events

Date	Code	Title	Description
2011-07-06	FC9A	Refused patent application

Publication	Publication Date	Title
SK286399B6 (sk)	2008-09-05	V podstate nehydratovaná a nehygroskopická alebo iba mierne hygroskopická hydrochloridová soľ 5-[4-[2-(N-metyl-N-(2- pyridyl)amino)etoxy]benzyl]tiazolidín-2,4-diónu, spôsob jej prípravy, farmaceutický prostriedok s jej obsahom a jej použitie
KR100744359B1 (ko)	2007-07-30	티아졸리딘디온 유도체 및 항당뇨병제로서 그의 용도
KR20010110797A (ko)	2001-12-13	5-[4-[2-(ｎ-메틸-ｎ-(2-피리딜)아미노)에톡시]벤질]티아졸리딘-2,4-디온 말레산염의 다형체
CA2314107A1 (en)	1999-06-24	5-[4-[2- (n-methyl-n- (2-pyridyl)amino) ethoxy]benzyl] thiazolidine-2, 4-dione, maleic acid salt, hydrate as pharmaceutical
CZ300934B6 (cs)	2009-09-16	Monohydrát 5-{4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl}thiazolidin-2,4-dion-hydrochloridu, zpusob jeho výroby, farmaceutický prostredek s jeho obsahem a použití
SK1442003A3 (en)	2004-05-04	Tartrate salts of thiazolidinedione derivative
SK2632003A3 (en)	2003-12-02	The hydrochloride salt of 5-[4-[2-(N-methyl-N-(2- pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione
SK3792003A3 (en)	2004-04-06	A thiazolidinedione derivative and its use as antidiabetic
US20070185167A1 (en)	2007-08-09	Sodium salts of 5-[4-[2-(n-methyl-n-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione
EP1305311B1 (de)	2008-01-16	Tartratsalze eines thiazolidinedione derivats
SK17142002A3 (sk)	2003-10-07	Soľ tiazolidindiónu na liečenie diabetes mellitus
BG107605A (bg)	2003-09-30	Тартаратни соли на тиазолидиндионово производно
SK17152002A3 (sk)	2003-05-02	Hydrojodid 5-[4-[2-(N-metyl-N-(2-pyridyl)amíno)etoxy]- benzyl]tiazolidín-2,4-diónu ako liečivo
SK287243B6 (sk)	2010-04-07	Soľ 5-[4-[2-(N-metyl-N-(2-pyridyl)amino)etoxy]benzyl]thiazolidín- 2,4-diónu a kyseliny L (+) vínnej, spôsob jej prípravy a použitie, farmaceutická kompozícia s jej obsahom
WO2003050112A1 (en)	2003-06-19	Toluenesulfonate hydrates of a thiazolidinedione derivative
WO2003050116A1 (en)	2003-06-19	A 5(-4-(2-(n-methyl-n-(2-pyridil)amino)ethoxy)benzyl)thiazolidine-2,4-dione (i) 10-camphorsulphonic acid salt and use against diabetes mellitus
WO2003053964A1 (en)	2003-07-03	5- (4- (2- (n-methyl-n- (2-pyridil) amino) ethoxy) benzyl) thiazolidine-2, 4-dione nephtalenesulfonate salt and use against diabetes mellitus
WO2003053963A1 (en)	2003-07-03	Novel pharmaceutical
HK1106226A (en)	2008-03-07	Sodium salts of 5-[4-[2-(n-methyl-n-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione