OA11900A - Substituted thiazolidinedione derivative, process for its preparation and its pharmaceutical use. - Google Patents

Substituted thiazolidinedione derivative, process for its preparation and its pharmaceutical use. Download PDF

Info

Publication number: OA11900A
Authority: OA; OAPI
Prior art keywords: hydrate; provides; hydrate according; daims; diabètes
Prior art date: 1997-12-16

Application number

OA00000177A

Other languages

English (en)

Inventor

Ian Robert Lynch

Barnadette Marie Choudary

Michael John Sasse

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.)

1997-12-16

Filing date

1998-12-14

Publication date

2006-04-10

1998-12-14 Application filed by Smithkline Beecham Plc filed Critical Smithkline Beecham Plc

2006-04-10 Publication of OA11900A publication Critical patent/OA11900A/en

Links

238000000034 method Methods 0.000 title claims abstract description 14
150000001467 thiazolidinediones Chemical class 0.000 title 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 33
150000001875 compounds Chemical class 0.000 claims abstract description 19
238000000634 powder X-ray diffraction Methods 0.000 claims abstract description 12
239000000126 substance Substances 0.000 claims abstract description 7
238000001237 Raman spectrum Methods 0.000 claims abstract description 5
238000002329 infrared spectrum Methods 0.000 claims abstract 3
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 9
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 9
238000011282 treatment Methods 0.000 claims description 8
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 7
239000011976 maleic acid Substances 0.000 claims description 7
238000011321 prophylaxis Methods 0.000 claims description 7
238000001228 spectrum Methods 0.000 claims description 6
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 5
239000007787 solid Substances 0.000 claims description 5
239000008194 pharmaceutical composition Substances 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
231100000252 nontoxic Toxicity 0.000 claims description 3
230000003000 nontoxic effect Effects 0.000 claims description 3
241000124008 Mammalia Species 0.000 claims description 2
230000001225 therapeutic effect Effects 0.000 claims description 2
229940098895 maleic acid Drugs 0.000 claims 2
239000000203 mixture Substances 0.000 abstract description 15
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract description 3
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 abstract description 3
239000003814 drug Substances 0.000 abstract description 2
150000002688 maleic acid derivatives Chemical class 0.000 abstract 1
238000000279 solid-state nuclear magnetic resonance spectrum Methods 0.000 abstract 1
239000002904 solvent Substances 0.000 description 11
239000003981 vehicle Substances 0.000 description 7
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
238000002425 crystallisation Methods 0.000 description 4
102000004877 Insulin Human genes 0.000 description 3
108090001061 Insulin Proteins 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
201000010099 disease Diseases 0.000 description 3
239000000945 filler Substances 0.000 description 3
229940125396 insulin Drugs 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000000843 powder Substances 0.000 description 3
239000003826 tablet Substances 0.000 description 3
239000000080 wetting agent Substances 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
208000008589 Obesity Diseases 0.000 description 2
235000011054 acetic acid Nutrition 0.000 description 2
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239000003795 chemical substances by application Substances 0.000 description 2
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238000010438 heat treatment Methods 0.000 description 2
239000000314 lubricant Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
235000020824 obesity Nutrition 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
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239000006188 syrup Substances 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-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
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 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
208000032841 Bulimia Diseases 0.000 description 1
206010006550 Bulimia nervosa Diseases 0.000 description 1
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 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
208000007342 Diabetic Nephropathies Diseases 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
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
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
206010020772 Hypertension Diseases 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
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
229930195725 Mannitol Natural products 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
238000001069 Raman spectroscopy Methods 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
229940123464 Thiazolidinedione Drugs 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
239000008168 almond oil Substances 0.000 description 1
239000004411 aluminium Substances 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
235000010210 aluminium Nutrition 0.000 description 1
239000003708 ampul Substances 0.000 description 1
230000003444 anaesthetic effect Effects 0.000 description 1
230000036528 appetite Effects 0.000 description 1
235000019789 appetite Nutrition 0.000 description 1
239000003125 aqueous solvent Substances 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000003139 buffering effect Effects 0.000 description 1
238000001875 carbon-13 cross-polarisation magic angle spinning nuclear magnetic resonance spectrum Methods 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
229920002678 cellulose Polymers 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000005388 cross polarization Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
208000033679 diabetic kidney disease Diseases 0.000 description 1
235000014632 disordered eating Nutrition 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000002934 diuretic Substances 0.000 description 1
229940030606 diuretics Drugs 0.000 description 1
MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 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
-1 esters of glycérine Chemical class 0.000 description 1
235000019441 ethanol Nutrition 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
239000012530 fluid Substances 0.000 description 1
239000012458 free base Substances 0.000 description 1
239000000499 gel Substances 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
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235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 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
238000000227 grinding Methods 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
239000005555 hypertensive agent Substances 0.000 description 1
230000002218 hypoglycaemic effect Effects 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000000787 lecithin Substances 0.000 description 1
235000010445 lecithin Nutrition 0.000 description 1
229940067606 lecithin Drugs 0.000 description 1
239000007937 lozenge Substances 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
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
238000002156 mixing Methods 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
239000002687 nonaqueous vehicle Substances 0.000 description 1
238000010899 nucleation Methods 0.000 description 1
239000003921 oil Substances 0.000 description 1
239000004533 oil dispersion 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
235000010603 pastilles Nutrition 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
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000007789 sealing Methods 0.000 description 1
229940080313 sodium starch Drugs 0.000 description 1
239000000243 solution 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
238000009987 spinning Methods 0.000 description 1
229940032147 starch Drugs 0.000 description 1
239000008107 starch Substances 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
239000000829 suppository Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 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

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
- 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

Landscapes

Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Diabetes (AREA)
Chemical Kinetics & Catalysis (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Veterinary Medicine (AREA)
Public Health (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)
General Health & Medical Sciences (AREA)
Hematology (AREA)
Obesity (AREA)
Endocrinology (AREA)
Emergency Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Thiazole And Isothizaole Compounds (AREA)
Medicines Containing Material From Animals Or Micro-Organisms (AREA)

OA00000177A 1997-12-16 1998-12-14 Substituted thiazolidinedione derivative, process for its preparation and its pharmaceutical use. OA11900A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GBGB9726563.1A GB9726563D0 (en)	1997-12-16	1997-12-16	Novel pharmaceutical

Publications (1)

Publication Number	Publication Date
OA11900A true OA11900A (en)	2006-04-10

Family

ID=10823691

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA00000177A OA11900A (en)	1997-12-16	1998-12-14	Substituted thiazolidinedione derivative, process for its preparation and its pharmaceutical use.

Country Status (37)

Country	Link
US (4)	US20020133016A1 (cs)
EP (1)	EP1042321A1 (cs)
JP (1)	JP2002508371A (cs)
KR (1)	KR100549141B1 (cs)
CN (3)	CN1285831A (cs)
AP (1)	AP1363A (cs)
AR (2)	AR016161A1 (cs)
AU (2)	AU2272299A (cs)
BG (1)	BG64850B1 (cs)
BR (1)	BR9813598A (cs)
CA (1)	CA2314967A1 (cs)
CO (1)	CO4990943A1 (cs)
CZ (1)	CZ300081B6 (cs)
DZ (1)	DZ2679A1 (cs)
EA (1)	EA002833B1 (cs)
EG (1)	EG22250A (cs)
GB (1)	GB9726563D0 (cs)
HR (1)	HRP20000404A2 (cs)
HU (1)	HUP0102292A3 (cs)
ID (1)	ID24714A (cs)
IL (2)	IL136425A (cs)
MA (1)	MA26581A1 (cs)
MY (1)	MY128573A (cs)
NO (1)	NO317255B1 (cs)
NZ (1)	NZ504703A (cs)
OA (1)	OA11900A (cs)
PE (1)	PE20000125A1 (cs)
PL (1)	PL341213A1 (cs)
RS (1)	RS50080B (cs)
SA (1)	SA99200200B1 (cs)
SK (1)	SK286422B6 (cs)
TR (2)	TR200001793T2 (cs)
TW (1)	TW487709B (cs)
UA (1)	UA66821C2 (cs)
UY (2)	UY25309A1 (cs)
WO (1)	WO1999031093A1 (cs)
ZA (1)	ZA9811504B (cs)

Families Citing this family (23)

* 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
US6664278B2 (en)	1997-12-16	2003-12-16	Smithkline Beecham P.L.C.	Hydrate of 5-[4-[2-(N-methyl-N-(2-pyridil)amino)ethoxy]benzyl]thiazolidine-2,4-dione maleic acid salt
GB9726568D0 (en) *	1997-12-16	1998-02-11	Smithkline Beecham Plc	Novel pharmaceutical
US20020137940A1 (en) *	1997-12-16	2002-09-26	Smithkline Beecham P.L.C.	5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2, 4-dione, maleic acid salt, hydrate as pharmaceutical
GB9909041D0 (en) *	1999-04-20	1999-06-16	Smithkline Beecham Plc	Novel pharmaceutical
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1997
- 1997-12-16 GB GBGB9726563.1A patent/GB9726563D0/en not_active Ceased
1998
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1999
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2000
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2003
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Also Published As

Publication number	Publication date
TR199802624A3 (tr)	1999-10-21
HUP0102292A3 (en)	2003-12-29
MY128573A (en)	2007-02-28
SK286422B6 (sk)	2008-09-05
AU770818B2 (en)	2004-03-04
EG22250A (en)	2002-11-30
EP1042321A1 (en)	2000-10-11
US7368574B2 (en)	2008-05-06
EA200000656A1 (ru)	2000-12-25
JP2002508371A (ja)	2002-03-19
US20020133016A1 (en)	2002-09-19
TR200001793T2 (tr)	2000-10-23
CZ20002206A3 (cs)	2000-12-13
HUP0102292A2 (hu)	2002-05-29
AU2272299A (en)	1999-07-05
UA66821C2 (uk)	2004-06-15
RS50080B (sr)	2009-01-22
UY25309A1 (es)	1999-07-19
NO20003070D0 (no)	2000-06-15
CZ300081B6 (cs)	2009-01-28
AU2753802A (en)	2002-05-16
BG104606A (en)	2001-02-28
KR100549141B1 (ko)	2006-02-03
IL160847A0 (en)	2004-08-31
HRP20000404A2 (en)	2000-12-31
AR016161A1 (es)	2001-06-20
NZ504703A (en)	2002-12-20
NO20003070L (no)	2000-06-15
NO317255B1 (no)	2004-09-27
IL136425A0 (en)	2001-06-14
TR199802624A2 (xx)	1999-10-21
TW487709B (en)	2002-05-21
MA26581A1 (fr)	2004-12-20
DZ2679A1 (fr)	2003-03-29
YU36400A (sh)	2003-12-31
SK9182000A3 (en)	2000-12-11
BR9813598A (pt)	2000-10-10
GB9726563D0 (en)	1998-02-11
AR017211A1 (es)	2001-08-22
US20050288513A1 (en)	2005-12-29
PE20000125A1 (es)	2000-03-03
ZA9811504B (en)	2000-06-15
AP2000001829A0 (en)	2000-06-30
US20070037859A1 (en)	2007-02-15
CA2314967A1 (en)	1999-06-24
ID24714A (id)	2000-08-03
PL341213A1 (en)	2001-03-26
US20030139604A1 (en)	2003-07-24
SA99200200B1 (ar)	2006-11-11
KR20010033140A (ko)	2001-04-25
EA002833B1 (ru)	2002-10-31
BG64850B1 (bg)	2006-06-30
WO1999031093A1 (en)	1999-06-24
AP1363A (en)	2005-01-21
CN101318957A (zh)	2008-12-10
CN1285831A (zh)	2001-02-28
IL136425A (en)	2004-08-31
UY25306A1 (es)	2000-12-29
CN101318956A (zh)	2008-12-10
CO4990943A1 (es)	2000-12-26

Publication	Publication Date	Title
US7368574B2 (en)	2008-05-06	Substituted thiazolidinedione derivative, process for its preparation and its pharmaceutical use
US20070203200A1 (en)	2007-08-30	5-[4-[2-(n-methyl-n-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione, maleic acid salt, hydrate as pharmaceutical
US6815457B1 (en)	2004-11-09	Thiazolidinedione derivative and its use as antidiabetic
EP1661895A1 (en)	2006-05-31	5-[4-[2-(n-methyl-n-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione,maleic acid salt,hydrate as pharmaceutical
US7045633B2 (en)	2006-05-16	Hydrate of 5-[4-[2-(N-methyl-N-(2-pyridil)amino)ethoxy]benzyl]thiazolidine-2,4-dione maleic acid salt
US6664278B2 (en)	2003-12-16	Hydrate of 5-[4-[2-(N-methyl-N-(2-pyridil)amino)ethoxy]benzyl]thiazolidine-2,4-dione maleic acid salt
US20040048899A1 (en)	2004-03-11	Tartrate salts of thiazollidnedione derivative
US20070185167A1 (en)	2007-08-09	Sodium salts of 5-[4-[2-(n-methyl-n-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione
US20040024027A1 (en)	2004-02-05	5(4-(2-(n-methyl-n-(2-pyridyl)amino)ethoxy)benzyl)thiazolidine-2,4-dione hydriodide as pharmaceutical
US20040038968A1 (en)	2004-02-26	Thiazolidinedione derivative and its use as antidiabetic
AU774613B2 (en)	2004-07-01	Hydrate of 5-(4-(2- (N-methyl-N- (2-pyridil)amino) ethoxy)benzyl) thiazolidine-2,4-dione maleic acid salt
AU770817B2 (en)	2004-03-04	5-(4-(2-(N-methyl-N-(2-pyridyl)amino)ethoxy)benzyl) thiazolidine-2,dione,maleic acid salt, hydrate as pharmaceutical
US20040087629A1 (en)	2004-05-06	Tartrate salts of thiazolidinedione derivative
WO2003050111A1 (en)	2003-06-19	Toluenesulfonate salts of a thiazolidinedione derivative
HK1092138A (en)	2007-02-02	5-[4-[2-(n-methyl-n-(2-pyridyl)amino)ethoxy]benzyl] thiazolidine-2, 4-dione, maleic acid salt, hydrate as pharmaceutical