SK1442003A3 - Tartrate salts of thiazolidinedione derivative - Google Patents

Tartrate salts of thiazolidinedione derivative Download PDF

Info

Publication number: SK1442003A3
Authority: SK; Slovakia
Prior art keywords: tartrate; solvate; compound; dione; pyridyl
Prior art date: 2000-08-04

Application number

SK144-2003A

Other languages

English (en)

Slovak (sk)

Inventor

Bernadette Marie Choudary

Andrew Simon Craig

Tim Chien Ting Ho

Donald Colin Mackenzie

Deirdre O'keeffe

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.)

2000-08-04

Filing date

2001-08-03

Publication date

2004-05-04

2001-08-03 Application filed by Smithkline Beecham Plc filed Critical Smithkline Beecham Plc

2004-05-04 Publication of SK1442003A3 publication Critical patent/SK1442003A3/sk

Links

150000003892 tartrate salts Chemical class 0.000 title description 2
150000001467 thiazolidinediones Chemical class 0.000 title description 2
FEWJPZIEWOKRBE-LWMBPPNESA-L D-tartrate(2-) Chemical compound [O-]C(=O)[C@@H](O)[C@H](O)C([O-])=O FEWJPZIEWOKRBE-LWMBPPNESA-L 0.000 claims abstract description 63
150000001875 compounds Chemical class 0.000 claims abstract description 38
239000012453 solvate Substances 0.000 claims abstract description 31
239000003814 drug Substances 0.000 claims abstract description 10
ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 claims abstract description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 4
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims abstract description 4
238000004519 manufacturing process Methods 0.000 claims abstract description 4
206010012601 diabetes mellitus Diseases 0.000 claims description 20
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 19
238000000034 method Methods 0.000 claims description 13
239000007787 solid Substances 0.000 claims description 12
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 11
150000003839 salts Chemical class 0.000 claims description 11
201000010099 disease Diseases 0.000 claims description 10
238000011282 treatment Methods 0.000 claims description 9
238000002360 preparation method Methods 0.000 claims description 8
239000000843 powder Substances 0.000 claims description 7
238000011321 prophylaxis Methods 0.000 claims description 7
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
238000000634 powder X-ray diffraction Methods 0.000 claims description 5
FEWJPZIEWOKRBE-JCYAYHJZSA-L L-tartrate(2-) Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-L 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 4
229940095064 tartrate Drugs 0.000 claims description 4
238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 claims description 3
238000003801 milling Methods 0.000 claims description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
239000007909 solid dosage form Substances 0.000 claims description 2
229940124597 therapeutic agent Drugs 0.000 claims description 2
125000004076 pyridyl group Chemical group 0.000 claims 1
239000000203 mixture Substances 0.000 abstract description 19
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
239000000243 solution Substances 0.000 description 13
239000000047 product Substances 0.000 description 12
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 10
AUONNNVJUCSETH-UHFFFAOYSA-N icosanoyl icosanoate Chemical compound CCCCCCCCCCCCCCCCCCCC(=O)OC(=O)CCCCCCCCCCCCCCCCCCC AUONNNVJUCSETH-UHFFFAOYSA-N 0.000 description 10
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
238000010992 reflux Methods 0.000 description 8
239000002904 solvent Substances 0.000 description 7
239000003981 vehicle Substances 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
-1 acetone Chemical class 0.000 description 6
235000019441 ethanol Nutrition 0.000 description 6
238000009472 formulation Methods 0.000 description 6
239000000725 suspension Substances 0.000 description 6
238000001914 filtration Methods 0.000 description 5
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
239000000126 substance Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
150000002500 ions Chemical class 0.000 description 4
239000007788 liquid Substances 0.000 description 4
208000001072 type 2 diabetes mellitus Diseases 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
208000030814 Eating disease Diseases 0.000 description 3
208000019454 Feeding and Eating disease Diseases 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
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
229940075894 denatured ethanol Drugs 0.000 description 3
235000014632 disordered eating Nutrition 0.000 description 3
239000002552 dosage form Substances 0.000 description 3
239000000945 filler Substances 0.000 description 3
238000011049 filling Methods 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
238000001228 spectrum Methods 0.000 description 3
239000003826 tablet Substances 0.000 description 3
239000000080 wetting agent Substances 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
238000010268 HPLC based assay Methods 0.000 description 2
206010020772 Hypertension Diseases 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
208000008589 Obesity Diseases 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
239000008186 active pharmaceutical agent Substances 0.000 description 2
229910001413 alkali metal ion Inorganic materials 0.000 description 2
239000013590 bulk material 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
239000003795 chemical substances by application Substances 0.000 description 2
239000003086 colorant Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000013078 crystal Substances 0.000 description 2
238000006731 degradation reaction Methods 0.000 description 2
238000000113 differential scanning calorimetry Methods 0.000 description 2
239000007884 disintegrant Substances 0.000 description 2
229940088679 drug related substance Drugs 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
239000000796 flavoring agent Substances 0.000 description 2
208000017169 kidney disease Diseases 0.000 description 2
239000007937 lozenge Substances 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
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
239000007790 solid phase Substances 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
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
238000004922 13C solid-state nuclear magnetic resonance spectroscopy Methods 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
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
IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 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
108010010803 Gelatin Proteins 0.000 description 1
206010018364 Glomerulonephritis Diseases 0.000 description 1
208000002705 Glucose Intolerance Diseases 0.000 description 1
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical class OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 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
241001490312 Lithops pseudotruncatella Species 0.000 description 1
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
239000004472 Lysine Substances 0.000 description 1
241000124008 Mammalia 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
241000042032 Petrocephalus catostoma Species 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
229920002472 Starch Polymers 0.000 description 1
QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
238000000862 absorption spectrum Methods 0.000 description 1
239000002253 acid 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
150000001447 alkali salts Chemical class 0.000 description 1
239000008168 almond oil Substances 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
235000010210 aluminium Nutrition 0.000 description 1
208000022531 anorexia Diseases 0.000 description 1
NGPGDYLVALNKEG-UHFFFAOYSA-N azanium;azane;2,3,4-trihydroxy-4-oxobutanoate Chemical compound [NH4+].[NH4+].[O-]C(=O)C(O)C(O)C([O-])=O NGPGDYLVALNKEG-UHFFFAOYSA-N 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
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
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
238000005388 cross polarization Methods 0.000 description 1
206010061428 decreased appetite Diseases 0.000 description 1
239000007857 degradation product Substances 0.000 description 1
239000008367 deionised water Substances 0.000 description 1
229910021641 deionized water Inorganic materials 0.000 description 1
238000013461 design Methods 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000006185 dispersion 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
238000001704 evaporation Methods 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
235000013355 food flavoring agent Nutrition 0.000 description 1
230000037406 food intake Effects 0.000 description 1
235000012631 food intake Nutrition 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
206010061989 glomerulosclerosis Diseases 0.000 description 1
239000008187 granular material Substances 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
238000003306 harvesting Methods 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 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
238000001802 infusion Methods 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
210000003734 kidney Anatomy 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
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
229910021645 metal ion Inorganic materials 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
201000009925 nephrosclerosis Diseases 0.000 description 1
150000002825 nitriles Chemical class 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
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000003182 parenteral nutrition solution Substances 0.000 description 1
239000008024 pharmaceutical diluent Substances 0.000 description 1
230000010363 phase shift Effects 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
238000012545 processing Methods 0.000 description 1
239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
235000010232 propyl p-hydroxybenzoate 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
238000011084 recovery Methods 0.000 description 1
230000003893 regulation of appetite Effects 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
239000011877 solvent mixture Substances 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
238000010561 standard procedure Methods 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
239000012258 stirred mixture Substances 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
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
231100000759 toxicological effect 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
229910052726 zirconium Inorganic materials 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
- A61P3/06—Antihyperlipidemics
- 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
- 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)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Diabetes (AREA)
General Chemical & Material Sciences (AREA)
General Health & Medical Sciences (AREA)
Hematology (AREA)
Obesity (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Bioinformatics & Cheminformatics (AREA)
Emergency Medicine (AREA)
Endocrinology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Cosmetics (AREA)

SK144-2003A 2000-08-04 2001-08-03 Tartrate salts of thiazolidinedione derivative SK1442003A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GBGB0019228.6A GB0019228D0 (en)	2000-08-04	2000-08-04	Novel pharmaceutical
PCT/GB2001/003515 WO2002012234A1 (en)	2000-08-04	2001-08-03	Tartrate salts of thiazolidinedione derivative

Publications (1)

Publication Number	Publication Date
SK1442003A3 true SK1442003A3 (en)	2004-05-04

Family

ID=9897030

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK144-2003A SK1442003A3 (en)	2000-08-04	2001-08-03	Tartrate salts of thiazolidinedione derivative

Country Status (35)

Country	Link
US (1)	US20040048899A1 (de)
EP (1)	EP1305312B1 (de)
JP (1)	JP2004505972A (de)
KR (1)	KR100755173B1 (de)
CN (1)	CN1458931A (de)
AP (1)	AP1814A (de)
AT (1)	ATE393153T1 (de)
AU (1)	AU2001276509A1 (de)
BG (1)	BG107606A (de)
BR (1)	BR0112981A (de)
CA (1)	CA2417829A1 (de)
CZ (1)	CZ2003316A3 (de)
DE (1)	DE60133746T2 (de)
DK (1)	DK1305312T3 (de)
DZ (1)	DZ3467A1 (de)
EA (1)	EA004764B1 (de)
EC (1)	ECSP034469A (de)
ES (1)	ES2302506T3 (de)
GB (1)	GB0019228D0 (de)
HR (1)	HRP20030070A2 (de)
HU (1)	HUP0300777A3 (de)
IL (2)	IL154278A0 (de)
MA (1)	MA25898A1 (de)
MX (1)	MXPA03001087A (de)
NO (1)	NO324595B1 (de)
NZ (1)	NZ524032A (de)
OA (1)	OA12352A (de)
PL (1)	PL360703A1 (de)
PT (1)	PT1305312E (de)
SI (1)	SI1305312T1 (de)
SK (1)	SK1442003A3 (de)
UA (1)	UA76721C2 (de)
WO (1)	WO2002012234A1 (de)
YU (1)	YU16303A (de)
ZA (1)	ZA200300963B (de)

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
MY144177A (en) *	2004-02-04	2011-08-15	Novartis Ag	Salt forms of 4-(4-methylpiperazin-1-ylmethyl)-n-[4-methyl-3-(4-pyridin-3-yl)pyrimidin-2-ylamino)phenyl]-benzamide.
CN1984903A (zh) *	2004-06-30	2007-06-20	伊莱利利公司	1－(吲哚－6－羰基－d－苯基甘氨酰基)－4－(1－甲基哌啶－4－基)哌嗪d－酒石酸盐
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
GB0616574D0 (en) *	2006-08-21	2006-09-27	Glaxo Group Ltd	Compounds
DE102009053562A1 (de)	2009-11-18	2011-05-19	Alfred E. Tiefenbacher (Gmbh & Co. Kg)	Rosiglitazonsuccinat enthaltende pharmazeutische Zusammensetzung
CN102532122B (zh) *	2010-12-29	2015-12-02	开封制药(集团)有限公司	酒石酸罗格列酮的制备方法

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6288095B1 (en) *	1987-09-04	2001-09-11	Beecham Group P.L.C.	Compounds
ATE186724T1 (de) *	1987-09-04	1999-12-15	Beecham Group Plc	Substituierte thiazolidindionderivate
US5741803A (en) *	1992-09-05	1998-04-21	Smithkline Beecham Plc	Substituted thiazolidinedionle derivatives
GB9218830D0 (en) *	1992-09-05	1992-10-21	Smithkline Beecham Plc	Novel compounds

2000
- 2000-08-04 GB GBGB0019228.6A patent/GB0019228D0/en not_active Ceased
2001
- 2001-03-08 UA UA2003020940A patent/UA76721C2/uk unknown
- 2001-08-03 AT AT01954162T patent/ATE393153T1/de not_active IP Right Cessation
- 2001-08-03 DE DE60133746T patent/DE60133746T2/de not_active Expired - Fee Related
- 2001-08-03 SK SK144-2003A patent/SK1442003A3/sk unknown
- 2001-08-03 DZ DZ013467A patent/DZ3467A1/fr active
- 2001-08-03 MX MXPA03001087A patent/MXPA03001087A/es active IP Right Grant
- 2001-08-03 CN CN01815685A patent/CN1458931A/zh active Pending
- 2001-08-03 ES ES01954162T patent/ES2302506T3/es not_active Expired - Lifetime
- 2001-08-03 OA OA1200300026A patent/OA12352A/en unknown
- 2001-08-03 US US10/343,866 patent/US20040048899A1/en not_active Abandoned
- 2001-08-03 JP JP2002518209A patent/JP2004505972A/ja not_active Withdrawn
- 2001-08-03 EP EP01954162A patent/EP1305312B1/de not_active Expired - Lifetime
- 2001-08-03 BR BR0112981-3A patent/BR0112981A/pt not_active IP Right Cessation
- 2001-08-03 AP APAP/P/2003/002738A patent/AP1814A/en active
- 2001-08-03 PL PL36070301A patent/PL360703A1/xx not_active Application Discontinuation
- 2001-08-03 EA EA200300234A patent/EA004764B1/ru not_active IP Right Cessation
- 2001-08-03 WO PCT/GB2001/003515 patent/WO2002012234A1/en not_active Ceased
- 2001-08-03 KR KR1020037001606A patent/KR100755173B1/ko not_active Expired - Fee Related
- 2001-08-03 HU HU0300777A patent/HUP0300777A3/hu unknown
- 2001-08-03 CA CA002417829A patent/CA2417829A1/en not_active Abandoned
- 2001-08-03 PT PT01954162T patent/PT1305312E/pt unknown
- 2001-08-03 AU AU2001276509A patent/AU2001276509A1/en not_active Abandoned
- 2001-08-03 SI SI200130830T patent/SI1305312T1/sl unknown
- 2001-08-03 HR HR20030070A patent/HRP20030070A2/hr not_active Application Discontinuation
- 2001-08-03 CZ CZ2003316A patent/CZ2003316A3/cs unknown
- 2001-08-03 NZ NZ524032A patent/NZ524032A/en unknown
- 2001-08-03 YU YU16303A patent/YU16303A/sh unknown
- 2001-08-03 IL IL15427801A patent/IL154278A0/xx active IP Right Grant
- 2001-08-03 DK DK01954162T patent/DK1305312T3/da active
2003
- 2003-01-31 NO NO20030507A patent/NO324595B1/no not_active IP Right Cessation
- 2003-02-03 MA MA27021A patent/MA25898A1/fr unknown
- 2003-02-03 IL IL154278A patent/IL154278A/en not_active IP Right Cessation
- 2003-02-04 EC EC2003004469A patent/ECSP034469A/es unknown
- 2003-02-28 BG BG107606A patent/BG107606A/bg unknown
- 2003-03-04 ZA ZA200300963A patent/ZA200300963B/en unknown

Also Published As

Publication number	Publication date
DE60133746D1 (de)	2008-06-05
HUP0300777A3 (en)	2005-04-28
GB0019228D0 (en)	2000-09-27
DK1305312T3 (da)	2008-07-28
MXPA03001087A (es)	2003-05-27
AP2003002738A0 (en)	2003-03-31
EA200300234A1 (ru)	2003-06-26
UA76721C2 (uk)	2006-09-15
IL154278A0 (en)	2003-09-17
KR20030022357A (ko)	2003-03-15
BR0112981A (pt)	2003-08-26
CZ2003316A3 (en)	2004-03-17
DZ3467A1 (fr)	2002-02-14
ATE393153T1 (de)	2008-05-15
EA004764B1 (ru)	2004-08-26
US20040048899A1 (en)	2004-03-11
OA12352A (en)	2006-05-16
ZA200300963B (en)	2004-04-19
HUP0300777A2 (hu)	2003-11-28
NO324595B1 (no)	2007-11-26
NO20030507D0 (no)	2003-01-31
WO2002012234A1 (en)	2002-02-14
AU2001276509A1 (en)	2002-02-18
ECSP034469A (es)	2003-06-25
ES2302506T3 (es)	2008-07-16
PT1305312E (pt)	2008-06-19
YU16303A (sh)	2006-01-16
KR100755173B1 (ko)	2007-09-03
JP2004505972A (ja)	2004-02-26
EP1305312A1 (de)	2003-05-02
DE60133746T2 (de)	2009-05-14
BG107606A (bg)	2003-09-30
CN1458931A (zh)	2003-11-26
SI1305312T1 (sl)	2008-08-31
EP1305312B1 (de)	2008-04-23
HK1057359A1 (en)	2004-04-02
CA2417829A1 (en)	2002-02-14
NO20030507L (no)	2003-03-26
IL154278A (en)	2009-02-11
AP1814A (en)	2008-01-04
PL360703A1 (en)	2004-09-20
NZ524032A (en)	2004-07-30
HRP20030070A2 (en)	2005-02-28
MA25898A1 (fr)	2003-10-01

Legal Events

Date	Code	Title	Description
2010-08-09	FB9A	Suspension of patent application procedure

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
CZ20002206A3 (cs)	2000-12-13	Substituovaný derivát thiazolidindionu, způsob jeho přípravy a jeho farmaceutické použití
CZ2003316A3 (en)	2004-03-17	Tartrate salts of thiazolidinedione derivative
BG107607A (bg)	2003-12-31	Хидрохлоридна сол на 5-[4-[2-(n-метил-n-(2-пиридил)амино)етокси]бензил]тиазолидин-2,4-дион
SK1452003A3 (en)	2004-05-04	Tartrate salts of thiazolidinedione derivative
EP1305311B1 (de)	2008-01-16	Tartratsalze eines thiazolidinedione derivats
SK1432003A3 (en)	2004-03-02	Tartrate salts of thiazolidinedione derivative
SK17142002A3 (sk)	2003-10-07	Soľ tiazolidindiónu na liečenie diabetes mellitus
CN1620453B (zh)	2010-12-08	噻唑烷二酮衍生物及其作为抗糖尿病药的用途
US20040014752A1 (en)	2004-01-22	Sodium salts of 5-[4-]2-(n-methyl-N-(2-pyridyl) ethoxy]benzyl]thiazolidine-2,4-dione
SK17152002A3 (sk)	2003-05-02	Hydrojodid 5-[4-[2-(N-metyl-N-(2-pyridyl)amíno)etoxy]- benzyl]tiazolidín-2,4-diónu ako liečivo
US20040102485A1 (en)	2004-05-27	Tartrate salt of thiazolidinedione derivative
HK1057358B (en)	2008-05-30	Tartrate salt of thiazolidinedione derivative