ZA200301809B - The hydrochloride salt of 5-[4[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione. - Google Patents

The hydrochloride salt of 5-[4[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione. Download PDF

Info

Publication number: ZA200301809B
Authority: ZA; South Africa
Prior art keywords: hydrochloride; accordance; methyl; pyridyl; ethoxy
Prior art date: 2000-09-06

Application number

ZA200301809A

Other languages

English (en)

Inventor

Craig Andrew Simon

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.)

2000-09-06

Filing date

2003-03-05

Publication date

2004-04-19

2003-03-05 Application filed by Smithkline Beecham Plc filed Critical Smithkline Beecham Plc

2004-04-19 Publication of ZA200301809B publication Critical patent/ZA200301809B/en

Links

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 title claims description 9
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 title claims description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 60
150000001875 compounds Chemical class 0.000 claims description 34
206010012601 diabetes mellitus Diseases 0.000 claims description 18
239000007787 solid Substances 0.000 claims description 15
238000000634 powder X-ray diffraction Methods 0.000 claims description 9
238000011282 treatment Methods 0.000 claims description 9
238000002844 melting Methods 0.000 claims description 8
230000008018 melting Effects 0.000 claims description 8
150000003839 salts Chemical class 0.000 claims description 8
238000011321 prophylaxis Methods 0.000 claims description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 5
238000001237 Raman spectrum Methods 0.000 claims description 5
238000002329 infrared spectrum Methods 0.000 claims description 5
239000008194 pharmaceutical composition Substances 0.000 claims description 5
239000002904 solvent Substances 0.000 claims description 5
238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 claims description 4
239000003814 drug Substances 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
239000000126 substance Substances 0.000 claims description 3
230000001225 therapeutic effect Effects 0.000 claims description 3
239000007909 solid dosage form Substances 0.000 claims description 2
239000000203 mixture Substances 0.000 description 20
239000000047 product Substances 0.000 description 14
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 13
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
239000000243 solution Substances 0.000 description 11
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
-1 acetone Chemical class 0.000 description 8
238000000034 method Methods 0.000 description 8
238000002425 crystallisation Methods 0.000 description 7
239000003981 vehicle Substances 0.000 description 7
XRSCTTPDKURIIJ-UHFFFAOYSA-N 5-[[4-[2-[methyl(pyridin-2-yl)amino]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione;hydrochloride Chemical compound Cl.C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O XRSCTTPDKURIIJ-UHFFFAOYSA-N 0.000 description 6
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
229910000041 hydrogen chloride Inorganic materials 0.000 description 6
238000002360 preparation method Methods 0.000 description 6
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 5
238000001914 filtration Methods 0.000 description 5
208000001072 type 2 diabetes mellitus Diseases 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
238000001816 cooling Methods 0.000 description 4
239000000463 material Substances 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
238000010268 HPLC based assay Methods 0.000 description 3
206010022489 Insulin Resistance Diseases 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
239000008186 active pharmaceutical agent Substances 0.000 description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 3
229940088679 drug related substance 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
239000007788 liquid Substances 0.000 description 3
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 3
239000000843 powder Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
239000003826 tablet Substances 0.000 description 3
239000000080 wetting agent Substances 0.000 description 3
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 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
MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 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
239000003795 chemical substances by application Substances 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
238000006731 degradation reaction Methods 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
239000007884 disintegrant Substances 0.000 description 2
208000035475 disorder Diseases 0.000 description 2
235000019441 ethanol Nutrition 0.000 description 2
239000000796 flavoring agent Substances 0.000 description 2
239000011521 glass Substances 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
238000002156 mixing Methods 0.000 description 2
150000002825 nitriles Chemical class 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
239000003755 preservative agent Substances 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000011084 recovery Methods 0.000 description 2
238000010992 reflux Methods 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
230000007704 transition Effects 0.000 description 2
ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-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
238000005160 1H NMR spectroscopy Methods 0.000 description 1
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical class [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 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
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
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-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
208000007342 Diabetic Nephropathies Diseases 0.000 description 1
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 1
239000004150 EU approved colour 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
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
239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
206010060378 Hyperinsulinaemia Diseases 0.000 description 1
206010020710 Hyperphagia 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
229930195725 Mannitol Natural products 0.000 description 1
229920000881 Modified starch Polymers 0.000 description 1
206010029164 Nephrotic syndrome Diseases 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
206010036049 Polycystic ovaries Diseases 0.000 description 1
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
239000004141 Sodium laurylsulphate Substances 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
238000000862 absorption spectrum Methods 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000013543 active substance Substances 0.000 description 1
239000000654 additive Substances 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
230000002411 adverse Effects 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
150000001412 amines Chemical class 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
239000003708 ampul Substances 0.000 description 1
230000003444 anaesthetic effect Effects 0.000 description 1
208000022531 anorexia Diseases 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000011230 binding agent Substances 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
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
235000010980 cellulose Nutrition 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 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
239000003240 coconut oil Substances 0.000 description 1
235000019864 coconut oil Nutrition 0.000 description 1
239000002131 composite material Substances 0.000 description 1
239000013256 coordination polymer 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
208000033679 diabetic kidney disease Diseases 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
238000000113 differential scanning calorimetry Methods 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
229940079593 drug Drugs 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
239000012530 fluid Substances 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
206010061989 glomerulosclerosis Diseases 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
239000008187 granular material Substances 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
238000004128 high performance liquid chromatography Methods 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
230000035879 hyperinsulinaemia Effects 0.000 description 1
230000001631 hypertensive effect Effects 0.000 description 1
230000002218 hypoglycaemic effect Effects 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
150000002576 ketones 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
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
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
FJQXCDYVZAHXNS-UHFFFAOYSA-N methadone hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(CC(C)N(C)C)(C(=O)CC)C1=CC=CC=C1 FJQXCDYVZAHXNS-UHFFFAOYSA-N 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 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
OZJSJUKQPIGBBO-UHFFFAOYSA-N n-methyl-n-[2-[4-(1,3-thiazolidin-5-ylmethyl)phenoxy]ethyl]pyridin-2-amine Chemical compound C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1CNCS1 OZJSJUKQPIGBBO-UHFFFAOYSA-N 0.000 description 1
201000009925 nephrosclerosis Diseases 0.000 description 1
239000002687 nonaqueous vehicle Substances 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
238000010899 nucleation Methods 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
229940006093 opthalmologic coloring agent diagnostic Drugs 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000020830 overeating Nutrition 0.000 description 1
239000003182 parenteral nutrition solution Substances 0.000 description 1
235000010603 pastilles Nutrition 0.000 description 1
239000008024 pharmaceutical diluent Substances 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
229910052698 phosphorus Inorganic materials 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
238000001556 precipitation Methods 0.000 description 1
201000009104 prediabetes syndrome Diseases 0.000 description 1
239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
235000013772 propylene glycol Nutrition 0.000 description 1
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
230000003893 regulation of appetite Effects 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
238000000646 scanning calorimetry Methods 0.000 description 1
238000007789 sealing Methods 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
229940080313 sodium starch Drugs 0.000 description 1
239000012265 solid product Substances 0.000 description 1
238000000371 solid-state nuclear magnetic resonance spectroscopy Methods 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
235000010199 sorbic acid Nutrition 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
239000000829 suppository Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
238000002076 thermal analysis method Methods 0.000 description 1
150000001467 thiazolidinediones Chemical class 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
230000002110 toxicologic effect Effects 0.000 description 1
231100000759 toxicological effect Toxicity 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
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- 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
- A61P3/04—Anorexiants; Antiobesity agents
- 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
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
- A61P5/50—Drugs for disorders of the endocrine system of the pancreatic hormones for increasing or potentiating the activity of insulin
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives

Landscapes

Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
General Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Diabetes (AREA)
Hematology (AREA)
Obesity (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Endocrinology (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Nutrition Science (AREA)
Emergency Medicine (AREA)
Child & Adolescent Psychology (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

ZA200301809A 2000-09-06 2003-03-05 The hydrochloride salt of 5-[4[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione. ZA200301809B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GBGB0021865.1A GB0021865D0 (en)	2000-09-06	2000-09-06	Novel pharmaceutical

Publications (1)

Publication Number	Publication Date
ZA200301809B true ZA200301809B (en)	2004-04-19

Family

ID=9898953

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ZA200301809A ZA200301809B (en)	2000-09-06	2003-03-05	The hydrochloride salt of 5-[4[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione.

Country Status (35)

Country	Link
US (3)	US20040034066A1 (hu)
EP (1)	EP1315723B1 (hu)
JP (1)	JP2004508369A (hu)
KR (1)	KR100770513B1 (hu)
CN (1)	CN100558717C (hu)
AP (1)	AP1715A (hu)
AT (1)	ATE300538T1 (hu)
AU (2)	AU2001284284B2 (hu)
BG (1)	BG107607A (hu)
BR (1)	BR0113713A (hu)
CA (1)	CA2421213A1 (hu)
CY (1)	CY1105252T1 (hu)
CZ (1)	CZ302125B6 (hu)
DE (1)	DE60112310T2 (hu)
DK (1)	DK1315723T3 (hu)
DZ (1)	DZ3475A1 (hu)
EA (1)	EA004296B1 (hu)
EC (1)	ECSP034505A (hu)
ES (1)	ES2244647T3 (hu)
GB (1)	GB0021865D0 (hu)
HK (1)	HK1057749A1 (hu)
HU (1)	HUP0300938A3 (hu)
IL (2)	IL154724A0 (hu)
MA (1)	MA25908A1 (hu)
MX (1)	MXPA03001956A (hu)
NO (1)	NO324020B1 (hu)
NZ (1)	NZ524548A (hu)
OA (1)	OA12375A (hu)
PL (1)	PL360578A1 (hu)
PT (1)	PT1315723E (hu)
SI (1)	SI1315723T1 (hu)
SK (1)	SK2632003A3 (hu)
UA (1)	UA74003C2 (hu)
WO (1)	WO2002020519A1 (hu)
ZA (1)	ZA200301809B (hu)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
USRE39384E1 (en)	1993-09-01	2006-11-07	Smithkline Beecham P.L.C.	Substituted thiazolidinedione derivatives
GB0006133D0 (en)	2000-03-14	2000-05-03	Smithkline Beecham Plc	Novel pharmaceutical
DE102005034406A1 (de) *	2005-07-22	2007-02-01	Ratiopharm Gmbh	Neue Salze von Rosiglitazon
US7435741B2 (en) *	2006-05-09	2008-10-14	Teva Pharmaceutical Industries, Ltd.	2-N{5-[[4-[2-(methyl-2-pyridinylamino) ethoxy] phenyl]methyl]-2,4-thiazolidinedione} butanedioic acid, methods of preparation and compositions with rosiglitazone maleate
JP5063714B2 (ja) *	2010-01-29	2012-10-31	シャープ株式会社	画像読取装置及び画像形成装置
EP2508525A1 (en)	2011-04-05	2012-10-10	Bayer Pharma Aktiengesellschaft	Substituted 2,3-dihydroimidazo[1,2-c]quinazoline salts
RU2487132C1 (ru) *	2012-07-23	2013-07-10	Общество с ограниченной ответственностью "Метаген"	Производные циклических 5-нитропиридин-2-ил-тиоалкенил-4-дитиокарбаматов, обладающие противогрибковой активностью, и их применение

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SG59988A1 (en) *	1987-09-04	1999-02-22	Beecham Group Plc	Substituted thiazolidinedione derivatives
US6288095B1 (en) *	1987-09-04	2001-09-11	Beecham Group P.L.C.	Compounds
GB9124513D0 (en) *	1991-11-19	1992-01-08	Smithkline Beecham Plc	Novel process
GB9218830D0 (en) *	1992-09-05	1992-10-21	Smithkline Beecham Plc	Novel compounds
US5741803A (en) *	1992-09-05	1998-04-21	Smithkline Beecham Plc	Substituted thiazolidinedionle derivatives
US5874454A (en) *	1993-09-15	1999-02-23	Warner-Lambert Company	Use of thiazolidinedione derivatives in the treatment of polycystic ovary syndrome, gestational diabetes and disease states at risk for progressing to noninsulin-dependent diabetes mellitus
DE69711862T2 (de) *	1997-07-17	2002-11-14	Interlemo Holding S.A., Saint-Sulpice	Steckverbindungssystem
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
GB0006133D0 (en) *	2000-03-14	2000-05-03	Smithkline Beecham Plc	Novel pharmaceutical
US6627646B2 (en) *	2001-07-17	2003-09-30	Sepracor Inc.	Norastemizole polymorphs

2000
- 2000-09-06 GB GBGB0021865.1A patent/GB0021865D0/en not_active Ceased
2001
- 2001-05-09 UA UA2003032020A patent/UA74003C2/uk unknown
- 2001-09-05 DZ DZ013475A patent/DZ3475A1/fr active
- 2001-09-05 CZ CZ20030615A patent/CZ302125B6/cs not_active IP Right Cessation
- 2001-09-05 HU HU0300938A patent/HUP0300938A3/hu unknown
- 2001-09-05 CA CA002421213A patent/CA2421213A1/en not_active Abandoned
- 2001-09-05 KR KR1020037003343A patent/KR100770513B1/ko not_active IP Right Cessation
- 2001-09-05 CN CNB018010784A patent/CN100558717C/zh not_active Expired - Fee Related
- 2001-09-05 PT PT01963254T patent/PT1315723E/pt unknown
- 2001-09-05 PL PL36057801A patent/PL360578A1/xx not_active Application Discontinuation
- 2001-09-05 AT AT01963254T patent/ATE300538T1/de active
- 2001-09-05 OA OA1200300068A patent/OA12375A/en unknown
- 2001-09-05 EA EA200300345A patent/EA004296B1/ru not_active IP Right Cessation
- 2001-09-05 US US10/363,608 patent/US20040034066A1/en not_active Abandoned
- 2001-09-05 AU AU2001284284A patent/AU2001284284B2/en not_active Ceased
- 2001-09-05 MX MXPA03001956A patent/MXPA03001956A/es active IP Right Grant
- 2001-09-05 BR BR0113713-1A patent/BR0113713A/pt not_active Application Discontinuation
- 2001-09-05 AU AU8428401A patent/AU8428401A/xx active Pending
- 2001-09-05 ES ES01963254T patent/ES2244647T3/es not_active Expired - Lifetime
- 2001-09-05 WO PCT/GB2001/003991 patent/WO2002020519A1/en active IP Right Grant
- 2001-09-05 IL IL15472401A patent/IL154724A0/xx unknown
- 2001-09-05 SI SI200130386T patent/SI1315723T1/xx unknown
- 2001-09-05 JP JP2002525140A patent/JP2004508369A/ja active Pending
- 2001-09-05 SK SK263-2003A patent/SK2632003A3/sk unknown
- 2001-09-05 DK DK01963254T patent/DK1315723T3/da active
- 2001-09-05 AP APAP/P/2003/002758A patent/AP1715A/en active
- 2001-09-05 NZ NZ524548A patent/NZ524548A/en unknown
- 2001-09-05 DE DE60112310T patent/DE60112310T2/de not_active Expired - Lifetime
- 2001-09-05 EP EP01963254A patent/EP1315723B1/en not_active Expired - Lifetime
2003
- 2003-02-28 BG BG107607A patent/BG107607A/bg unknown
- 2003-03-03 IL IL154724A patent/IL154724A/en not_active IP Right Cessation
- 2003-03-05 ZA ZA200301809A patent/ZA200301809B/en unknown
- 2003-03-05 NO NO20031020A patent/NO324020B1/no not_active IP Right Cessation
- 2003-03-06 MA MA27065A patent/MA25908A1/fr unknown
- 2003-03-06 EC EC2003004505A patent/ECSP034505A/es unknown
- 2003-11-25 HK HK03108589A patent/HK1057749A1/xx not_active IP Right Cessation
2005
- 2005-08-04 US US11/197,108 patent/US20050282867A1/en not_active Abandoned
- 2005-09-13 CY CY20051101110T patent/CY1105252T1/el unknown
2007
- 2007-04-24 US US11/739,132 patent/US20070191435A1/en not_active Abandoned

Also Published As

Publication number	Publication date
DZ3475A1 (fr)	2002-03-14
HK1057749A1 (en)	2004-04-16
IL154724A (en)	2009-07-20
CA2421213A1 (en)	2002-03-14
EA200300345A1 (ru)	2003-08-28
DE60112310T2 (de)	2006-02-09
NO324020B1 (no)	2007-07-30
US20070191435A1 (en)	2007-08-16
AU8428401A (en)	2002-03-22
CZ302125B6 (cs)	2010-11-03
DE60112310D1 (de)	2005-09-01
GB0021865D0 (en)	2000-10-18
AP2003002758A0 (en)	2003-06-30
ATE300538T1 (de)	2005-08-15
ECSP034505A (es)	2003-06-25
PT1315723E (pt)	2005-11-30
US20050282867A1 (en)	2005-12-22
PL360578A1 (en)	2004-09-06
CN100558717C (zh)	2009-11-11
BR0113713A (pt)	2004-07-06
CZ2003615A3 (cs)	2003-11-12
SK2632003A3 (en)	2003-12-02
EP1315723B1 (en)	2005-07-27
JP2004508369A (ja)	2004-03-18
KR20030027118A (ko)	2003-04-03
SI1315723T1 (en)	2005-10-31
US20040034066A1 (en)	2004-02-19
NO20031020D0 (no)	2003-03-05
IL154724A0 (en)	2003-10-31
EP1315723A1 (en)	2003-06-04
CY1105252T1 (el)	2010-03-03
BG107607A (bg)	2003-12-31
NO20031020L (no)	2003-05-06
AP1715A (en)	2007-02-28
MA25908A1 (fr)	2003-10-01
KR100770513B1 (ko)	2007-10-25
EA004296B1 (ru)	2004-02-26
NZ524548A (en)	2004-10-29
CN1366520A (zh)	2002-08-28
HUP0300938A3 (en)	2005-04-28
UA74003C2 (en)	2005-10-17
MXPA03001956A (es)	2003-06-24
AU2001284284B2 (en)	2005-08-04
ES2244647T3 (es)	2005-12-16
HUP0300938A2 (hu)	2003-11-28
WO2002020519A1 (en)	2002-03-14
OA12375A (en)	2004-03-19
DK1315723T3 (da)	2005-10-24

Publication	Publication Date	Title
US20070191435A1 (en)	2007-08-16	Hydrochloride salt of 5-[4-[2-(n-methyl-n-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione
US20040082620A1 (en)	2004-04-29	5'-4-'2-(n-methyl-n-(2-pyridyl)amino)ethoxy!benzyl!thiazolidine-2, 4-dione mesylate salt
AU2001284284A1 (en)	2002-06-13	The hydrochloride salt of 5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl] thiazolidine-2,4-dione
EP1446404B1 (en)	2006-06-14	Rosiglitazone edisylates and their use as antidiabetics
EP1315724B1 (en)	2005-11-16	A thiazolidinedione derivative and its use as antidiabetic
AU2001276509A1 (en)	2002-02-18	Tartrate salts of thiazolidinedione derivative
US20040014791A1 (en)	2004-01-22	Thiazolidinedione derivative and its use as antidiabetic
US20040014790A1 (en)	2004-01-22	Tartrate salt of thiazolidinedione derivative
AU2001292034B2 (en)	2005-04-21	A thiazolidinedione derivative and its use as antidiabetic
US20040029926A1 (en)	2004-02-12	Thiazolidinone nitrate salt
US20040087629A1 (en)	2004-05-06	Tartrate salts of thiazolidinedione derivative
AU2001292034A1 (en)	2002-06-20	A thiazolidinedione derivative and its use as antidiabetic
WO2003050111A1 (en)	2003-06-19	Toluenesulfonate salts of a thiazolidinedione derivative
EP1448559A1 (en)	2004-08-25	5-[4-[2-(n-methyl-n-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione benzenesulfonate; process for its preparation; polymorphs i, ii and iii thereof; and its use as pharmaceutical active ingredient
AU2005229687A1 (en)	2005-11-24	Tartrate salts of thiazolidinedione derivative