UA73974C2 - Hydrochloride 5-[4-[2-(n-methyl-n-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione, a process of preparing thereof and a pharmaceutical composition based thereon - Google Patents

Hydrochloride 5-[4-[2-(n-methyl-n-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione, a process of preparing thereof and a pharmaceutical composition based thereon Download PDF

Info

Publication number: UA73974C2
Authority: UA; Ukraine
Prior art keywords: hydrochloride; compound; pyridyl; methyl; amino
Prior art date: 2000-03-14

Application number

UA2002097390A

Other languages

English (en)

Ukrainian (uk)

Inventor

Andrew Simon Craig

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.)

2000-03-14

Filing date

2001-03-14

Publication date

2005-10-17

2001-03-14 Application filed by Smithkline Beecham Plc filed Critical Smithkline Beecham Plc

2005-10-17 Publication of UA73974C2 publication Critical patent/UA73974C2/uk

Links

238000000034 method Methods 0.000 title claims abstract description 11
239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 title claims description 57
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 abstract 2
150000001875 compounds Chemical class 0.000 claims abstract description 33
206010012601 diabetes mellitus Diseases 0.000 claims description 19
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 10
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
150000003839 salts Chemical class 0.000 claims description 7
238000002329 infrared spectrum Methods 0.000 claims description 6
239000000843 powder Substances 0.000 claims description 6
230000002265 prevention Effects 0.000 claims description 6
238000001228 spectrum Methods 0.000 claims description 6
238000002441 X-ray diffraction Methods 0.000 claims description 5
229910000041 hydrogen chloride Inorganic materials 0.000 claims description 5
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 5
239000002904 solvent Substances 0.000 claims description 5
238000001069 Raman spectroscopy Methods 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 4
239000000126 substance Substances 0.000 claims description 3
230000001225 therapeutic effect Effects 0.000 claims description 2
230000003993 interaction Effects 0.000 claims 1
150000003840 hydrochlorides Chemical class 0.000 abstract description 2
239000000243 solution Substances 0.000 description 15
239000000203 mixture Substances 0.000 description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
-1 acetone Chemical class 0.000 description 6
239000000725 suspension Substances 0.000 description 6
238000002360 preparation method Methods 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
238000002425 crystallisation Methods 0.000 description 4
230000008025 crystallization Effects 0.000 description 4
239000007788 liquid Substances 0.000 description 4
238000007911 parenteral administration Methods 0.000 description 4
239000000047 product Substances 0.000 description 4
239000007787 solid Substances 0.000 description 4
208000001072 type 2 diabetes mellitus Diseases 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 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
238000011049 filling Methods 0.000 description 3
238000001914 filtration Methods 0.000 description 3
238000002156 mixing Methods 0.000 description 3
239000000546 pharmaceutical excipient Substances 0.000 description 3
239000000825 pharmaceutical preparation Substances 0.000 description 3
239000000080 wetting agent Substances 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
208000030814 Eating disease Diseases 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
208000019454 Feeding and Eating disease Diseases 0.000 description 2
206010020772 Hypertension Diseases 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
239000013543 active substance Substances 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
239000002775 capsule Substances 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
239000003085 diluting agent Substances 0.000 description 2
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
239000007884 disintegrant Substances 0.000 description 2
235000014632 disordered eating Nutrition 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
239000003814 drug Substances 0.000 description 2
239000000945 filler Substances 0.000 description 2
239000000796 flavoring agent 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
238000004519 manufacturing process Methods 0.000 description 2
235000020824 obesity Nutrition 0.000 description 2
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
238000000634 powder X-ray diffraction Methods 0.000 description 2
239000003755 preservative agent Substances 0.000 description 2
238000004062 sedimentation Methods 0.000 description 2
239000012265 solid product Substances 0.000 description 2
239000006188 syrup Substances 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
238000012360 testing method Methods 0.000 description 2
ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
SLYRGJDSFOCAAI-UHFFFAOYSA-N 1,3-thiazolidin-2-one Chemical class O=C1NCCS1 SLYRGJDSFOCAAI-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
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
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
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 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
239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
206010060378 Hyperinsulinaemia 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
240000007472 Leucaena leucocephala Species 0.000 description 1
235000010643 Leucaena leucocephala Nutrition 0.000 description 1
208000002720 Malnutrition Diseases 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
229920000881 Modified starch Polymers 0.000 description 1
206010029164 Nephrotic syndrome Diseases 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
238000001237 Raman spectrum Methods 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
239000004480 active ingredient 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
229940063655 aluminum stearate Drugs 0.000 description 1
239000003708 ampul Substances 0.000 description 1
208000022531 anorexia Diseases 0.000 description 1
235000021229 appetite regulation Nutrition 0.000 description 1
239000008365 aqueous carrier 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
229920002678 cellulose Polymers 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 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
229940125904 compound 1 Drugs 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
206010061428 decreased appetite Diseases 0.000 description 1
238000011161 development Methods 0.000 description 1
208000033679 diabetic kidney disease Diseases 0.000 description 1
238000000113 differential scanning calorimetry Methods 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000008157 edible vegetable oil Substances 0.000 description 1
238000000921 elemental analysis Methods 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
150000002148 esters 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
238000002474 experimental method Methods 0.000 description 1
238000000605 extraction Methods 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
150000002314 glycerols Chemical class 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
230000000055 hyoplipidemic effect Effects 0.000 description 1
201000001421 hyperglycemia Diseases 0.000 description 1
230000003451 hyperinsulinaemic effect Effects 0.000 description 1
201000008980 hyperinsulinism Diseases 0.000 description 1
230000001631 hypertensive effect Effects 0.000 description 1
230000002218 hypoglycaemic effect Effects 0.000 description 1
238000001802 infusion Methods 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
230000000977 initiatory effect Effects 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
239000008101 lactose Substances 0.000 description 1
238000011031 large-scale manufacturing process Methods 0.000 description 1
229940057995 liquid paraffin Drugs 0.000 description 1
239000003589 local anesthetic agent Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
230000001071 malnutrition Effects 0.000 description 1
235000000824 malnutrition Nutrition 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 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
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
239000011259 mixed solution Substances 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
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012299 nitrogen atmosphere 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
208000015380 nutritional deficiency disease Diseases 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
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
239000004405 propyl p-hydroxybenzoate Substances 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
239000011541 reaction mixture Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000007789 sealing Methods 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
229920003109 sodium starch glycolate Polymers 0.000 description 1
239000008109 sodium starch glycolate Substances 0.000 description 1
229940079832 sodium starch glycolate Drugs 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
239000001593 sorbitan monooleate Substances 0.000 description 1
235000011069 sorbitan monooleate Nutrition 0.000 description 1
229940035049 sorbitan monooleate Drugs 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
235000010356 sorbitol Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
229940032147 starch Drugs 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
238000004659 sterilization and disinfection Methods 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
229940124597 therapeutic agent Drugs 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
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
238000009827 uniform distribution Methods 0.000 description 1
239000003981 vehicle Substances 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
- 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

Landscapes

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

UA2002097390A 2000-03-14 2001-03-14 Hydrochloride 5-[4-[2-(n-methyl-n-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione, a process of preparing thereof and a pharmaceutical composition based thereon UA73974C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GBGB0006133.3A GB0006133D0 (en)	2000-03-14	2000-03-14	Novel pharmaceutical
PCT/GB2001/001131 WO2001068646A1 (en)	2000-03-14	2001-03-14	Hydrochloride salts of 5-[4-[2-(n-methyl-n-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione

Publications (1)

Publication Number	Publication Date
UA73974C2 true UA73974C2 (en)	2005-10-17

Family

ID=9887600

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UA2002097390A UA73974C2 (en)	2000-03-14	2001-03-14	Hydrochloride 5-[4-[2-(n-methyl-n-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione, a process of preparing thereof and a pharmaceutical composition based thereon

Country Status (30)

Country	Link
US (2)	US7074811B2 (cs)
EP (1)	EP1265893B1 (cs)
JP (1)	JP2003527393A (cs)
KR (1)	KR100746813B1 (cs)
CN (1)	CN100516062C (cs)
AP (1)	AP1545A (cs)
AT (1)	ATE302202T1 (cs)
AU (1)	AU777987B2 (cs)
BG (1)	BG65924B1 (cs)
BR (1)	BR0108870A (cs)
CA (1)	CA2403109A1 (cs)
CZ (1)	CZ20023074A3 (cs)
DE (1)	DE60112729T2 (cs)
DK (1)	DK1265893T3 (cs)
DZ (1)	DZ3316A1 (cs)
EA (1)	EA005115B1 (cs)
ES (1)	ES2243458T3 (cs)
GB (1)	GB0006133D0 (cs)
HU (1)	HUP0300158A3 (cs)
IL (2)	IL151425A0 (cs)
MA (1)	MA25658A1 (cs)
MX (1)	MXPA02008972A (cs)
NO (1)	NO323448B1 (cs)
NZ (1)	NZ520910A (cs)
OA (1)	OA12229A (cs)
PL (1)	PL357283A1 (cs)
SK (1)	SK286399B6 (cs)
UA (1)	UA73974C2 (cs)
WO (1)	WO2001068646A1 (cs)
ZA (1)	ZA200207292B (cs)

Families Citing this family (34)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB0021865D0 (en) *	2000-09-06	2000-10-18	Smithkline Beecham Plc	Novel pharmaceutical
GB0023971D0 (en) *	2000-09-29	2000-11-15	Smithkline Beecham Plc	Novel pharmaceutical
WO2003045946A1 (en) *	2001-11-21	2003-06-05	Smithkline Beecham P.L.C.	5-(4-(2-(n-methyl-n-(2-pyridil) 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
GB0129876D0 (en) *	2001-12-13	2002-02-06	Smithkline Beecham Plc	Novel pharmaceutical
WO2003050112A1 (en) *	2001-12-13	2003-06-19	Smithkline Beecham Plc	Toluenesulfonate hydrates of a thiazolidinedione derivative
US7407955B2 (en)	2002-08-21	2008-08-05	Boehringer Ingelheim Pharma Gmbh & Co., Kg	8-[3-amino-piperidin-1-yl]-xanthines, the preparation thereof and their use as pharmaceutical compositions
US7501426B2 (en)	2004-02-18	2009-03-10	Boehringer Ingelheim International Gmbh	8-[3-amino-piperidin-1-yl]-xanthines, their preparation and their use as pharmaceutical compositions
WO2006018853A2 (en)	2004-08-19	2006-02-23	Hetero Drugs Limited	Novel polymorphs of efavirenz
DE102004054054A1 (de)	2004-11-05	2006-05-11	Boehringer Ingelheim Pharma Gmbh & Co. Kg	Verfahren zur Herstellung chiraler 8-(3-Amino-piperidin-1-yl)-xanthine
DE102005035891A1 (de)	2005-07-30	2007-02-08	Boehringer Ingelheim Pharma Gmbh & Co. Kg	8-(3-Amino-piperidin-1-yl)-xanthine, deren Herstellung und deren Verwendung als Arzneimittel
PE20080251A1 (es)	2006-05-04	2008-04-25	Boehringer Ingelheim Int	Usos de inhibidores de dpp iv
EP1852108A1 (en)	2006-05-04	2007-11-07	Boehringer Ingelheim Pharma GmbH & Co.KG	DPP IV inhibitor formulations
BRPI0711558A2 (pt)	2006-05-04	2011-11-08	Boeringer Ingelheim Internat Gmbh	polimorfos
US20090076093A1 (en) *	2007-09-14	2009-03-19	Protia, Llc	Deuterium-enriched rosiglitazone
PE20140960A1 (es)	2008-04-03	2014-08-15	Boehringer Ingelheim Int	Formulaciones que comprenden un inhibidor de dpp4
UY32030A (es)	2008-08-06	2010-03-26	Boehringer Ingelheim Int	"tratamiento para diabetes en pacientes inapropiados para terapia con metformina"
BRPI0916997A2 (pt)	2008-08-06	2020-12-15	Boehringer Ingelheim International Gmbh	Inibidor de dpp-4 e seu uso
AU2009290911A1 (en)	2008-09-10	2010-03-18	Boehringer Ingelheim International Gmbh	Combination therapy for the treatment of diabetes and related conditions
US20200155558A1 (en)	2018-11-20	2020-05-21	Boehringer Ingelheim International Gmbh	Treatment for diabetes in patients with insufficient glycemic control despite therapy with an oral antidiabetic drug
US20100158821A1 (en) *	2008-12-22	2010-06-24	Eastman Chemical Company	Antimicrobial agents, compositions and products containing the same, and methods of using the compositions and products
EP2382216A1 (en)	2008-12-23	2011-11-02	Boehringer Ingelheim International GmbH	Salt forms of organic compound
AR074990A1 (es)	2009-01-07	2011-03-02	Boehringer Ingelheim Int	Tratamiento de diabetes en pacientes con un control glucemico inadecuado a pesar de la terapia con metformina
US8106111B2 (en) *	2009-05-15	2012-01-31	Eastman Chemical Company	Antimicrobial effect of cycloaliphatic diol antimicrobial agents in coating compositions
EA034869B1 (ru)	2009-11-27	2020-03-31	Бёрингер Ингельхайм Интернациональ Гмбх	Лечение генотипированных пациентов с диабетом ингибиторами дпп-4, такими как линаглиптин
MX341025B (es)	2010-05-05	2016-08-04	Boehringer Ingelheim Int Gmbh *	Terapia de combinacion.
PH12012502524A1 (en)	2010-06-24	2014-02-10	Boehringer Ingelheim Int	Diabetes therapy
US9034883B2 (en)	2010-11-15	2015-05-19	Boehringer Ingelheim International Gmbh	Vasoprotective and cardioprotective antidiabetic therapy
EP3517539B1 (en)	2011-07-15	2022-12-14	Boehringer Ingelheim International GmbH	Substituted dimeric quinazoline derivative, its preparation and its use in pharmaceutical compositions for the treatment of type i and ii diabetes
US9555001B2 (en)	2012-03-07	2017-01-31	Boehringer Ingelheim International Gmbh	Pharmaceutical composition and uses thereof
US20130303554A1 (en)	2012-05-14	2013-11-14	Boehringer Ingelheim International Gmbh	Use of a dpp-4 inhibitor in sirs and/or sepsis
JP6224084B2 (ja)	2012-05-14	2017-11-01	ベーリンガーインゲルハイムインターナショナルゲゼルシャフトミットベシュレンクテルハフツング	糸球体上皮細胞関連障害及び／又はネフローゼ症候群の治療に用いるｄｐｐ−４阻害薬としてのキサンチン誘導体
WO2013174767A1 (en)	2012-05-24	2013-11-28	Boehringer Ingelheim International Gmbh	A xanthine derivative as dpp -4 inhibitor for use in modifying food intake and regulating food preference
US9526728B2 (en)	2014-02-28	2016-12-27	Boehringer Ingelheim International Gmbh	Medical use of a DPP-4 inhibitor
CN109310697A (zh)	2016-06-10	2019-02-05	勃林格殷格翰国际有限公司	利格列汀和二甲双胍的组合

Family Cites Families (20)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US137940A (en) *		1873-04-15		Improvement in elevators
US120078A (en) *		1871-10-17		Improvement in revolving flower-stands
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
GB9413975D0 (en) *	1994-07-11	1994-08-31	Fujisawa Pharmaceutical Co	New heterobicyclic derivatives
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
US5708012A (en) *	1995-04-28	1998-01-13	Sankyo Company, Limited	Use of thiazolidinedione derivatives and related antihyperglycemic agents in the treatment of insulin resistant subjects with normal glucose tolerance in order to prevent or delay the onset of noninsulin-dependent mellitus
TR199903057T2 (xx)	1997-06-18	2000-04-21	Smithkline Beecham Plc	Diabetin tiazolidinedion ve metformin ile tedavisi.
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
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
GB9909041D0 (en)	1999-04-20	1999-06-16	Smithkline Beecham Plc	Novel pharmaceutical
GB9909075D0 (en)	1999-04-20	1999-06-16	Smithkline Beecham Plc	Novel pharmaceutical
AR023561A1 (es)	1999-04-23	2002-09-04	Smithkline Beecham Corp	Una forma polimorfica del acido maleico de un derivado de tiazolidin-2, 4 diona, una composicion farmaceutica y el uso de dicho polimorfo para lafabricacion de un medicamento
CZ20013801A3 (cs)	1999-04-23	2002-07-17	Smithkline Beecham Plc	Nový léčivý přípravek
HRP20010773B1 (en)	1999-04-23	2005-06-30	Smithkline Beecham P.L.C.	Thiazolidinedione derivative and its use as antidiabetic
HU225919B1 (en)	1999-12-18	2007-12-28	Richter Gedeon Nyrt	Thiazolidine-derivatives, process for their preparation pharmaceutical and intermediates
CN1277965A (zh)	2000-06-14	2000-12-27	中国医药研究开发中心	盐酸罗格列酮及其应用
GB0021865D0 (en)	2000-09-06	2000-10-18	Smithkline Beecham Plc	Novel pharmaceutical

2000
- 2000-03-14 GB GBGB0006133.3A patent/GB0006133D0/en not_active Ceased
2001
- 2001-03-14 ES ES01911921T patent/ES2243458T3/es not_active Expired - Lifetime
- 2001-03-14 MX MXPA02008972A patent/MXPA02008972A/es active IP Right Grant
- 2001-03-14 PL PL01357283A patent/PL357283A1/xx not_active Application Discontinuation
- 2001-03-14 AP APAP/P/2002/002600A patent/AP1545A/en active
- 2001-03-14 JP JP2001567737A patent/JP2003527393A/ja active Pending
- 2001-03-14 CZ CZ20023074A patent/CZ20023074A3/cs unknown
- 2001-03-14 OA OA1200200285A patent/OA12229A/en unknown
- 2001-03-14 US US10/221,686 patent/US7074811B2/en not_active Expired - Fee Related
- 2001-03-14 BR BR0108870-0A patent/BR0108870A/pt not_active IP Right Cessation
- 2001-03-14 SK SK1330-2002A patent/SK286399B6/sk not_active IP Right Cessation
- 2001-03-14 EP EP01911921A patent/EP1265893B1/en not_active Expired - Lifetime
- 2001-03-14 DZ DZ013316A patent/DZ3316A1/fr active
- 2001-03-14 CN CNB018000010A patent/CN100516062C/zh not_active Expired - Fee Related
- 2001-03-14 AU AU40843/01A patent/AU777987B2/en not_active Ceased
- 2001-03-14 UA UA2002097390A patent/UA73974C2/uk unknown
- 2001-03-14 IL IL15142501A patent/IL151425A0/xx unknown
- 2001-03-14 EA EA200200975A patent/EA005115B1/ru not_active IP Right Cessation
- 2001-03-14 KR KR1020027011997A patent/KR100746813B1/ko not_active Expired - Fee Related
- 2001-03-14 NZ NZ520910A patent/NZ520910A/en not_active IP Right Cessation
- 2001-03-14 DK DK01911921T patent/DK1265893T3/da active
- 2001-03-14 HU HU0300158A patent/HUP0300158A3/hu unknown
- 2001-03-14 AT AT01911921T patent/ATE302202T1/de active
- 2001-03-14 DE DE60112729T patent/DE60112729T2/de not_active Expired - Lifetime
- 2001-03-14 WO PCT/GB2001/001131 patent/WO2001068646A1/en not_active Ceased
- 2001-03-14 CA CA002403109A patent/CA2403109A1/en not_active Abandoned
2002
- 2002-08-20 BG BG107012A patent/BG65924B1/bg unknown
- 2002-08-22 IL IL151425A patent/IL151425A/en not_active IP Right Cessation
- 2002-09-09 NO NO20024307A patent/NO323448B1/no not_active IP Right Cessation
- 2002-09-11 ZA ZA200207292A patent/ZA200207292B/en unknown
- 2002-09-12 MA MA26814A patent/MA25658A1/fr unknown
2005
- 2005-07-18 US US11/183,353 patent/US20050267162A1/en not_active Abandoned

Also Published As

Publication number	Publication date
IL151425A0 (en)	2003-04-10
AP1545A (en)	2006-01-12
US20040152901A1 (en)	2004-08-05
HUP0300158A3 (en)	2005-04-28
DZ3316A1 (fr)	2001-09-20
CN100516062C (zh)	2009-07-22
ZA200207292B (en)	2003-05-06
US20050267162A1 (en)	2005-12-01
NO323448B1 (no)	2007-05-07
EA200200975A1 (ru)	2003-02-27
KR100746813B1 (ko)	2007-08-06
NO20024307D0 (no)	2002-09-09
KR20020079998A (ko)	2002-10-21
WO2001068646A1 (en)	2001-09-20
EP1265893B1 (en)	2005-08-17
AU4084301A (en)	2001-09-24
CA2403109A1 (en)	2001-09-20
MXPA02008972A (es)	2003-02-10
BG107012A (bg)	2003-04-30
EA005115B1 (ru)	2004-10-28
SK13302002A3 (sk)	2003-02-04
BG65924B1 (bg)	2010-05-31
BR0108870A (pt)	2002-12-17
MA25658A1 (fr)	2002-12-31
DE60112729T2 (de)	2006-06-08
HK1052502A1 (en)	2003-09-19
NO20024307L (no)	2002-09-09
ES2243458T3 (es)	2005-12-01
HUP0300158A2 (en)	2003-05-28
DE60112729D1 (de)	2005-09-22
DK1265893T3 (da)	2005-11-14
CN1358184A (zh)	2002-07-10
JP2003527393A (ja)	2003-09-16
PL357283A1 (en)	2004-07-26
AU777987B2 (en)	2004-11-11
CZ20023074A3 (cs)	2003-02-12
GB0006133D0 (en)	2000-05-03
US7074811B2 (en)	2006-07-11
IL151425A (en)	2009-08-03
AP2002002600A0 (en)	2002-09-30
SK286399B6 (sk)	2008-09-05
OA12229A (en)	2003-11-07
EP1265893A1 (en)	2002-12-18
ATE302202T1 (de)	2005-09-15
NZ520910A (en)	2004-06-25

Publication	Publication Date	Title
EA005115B1 (ru)	2004-10-28	Гидрохлорид 5-[4-[2-(n-метил-n-(2-пиридил)амино)этокси]бензил]тиазолидин-2,4-диона
EA004260B1 (ru)	2004-02-26	Гидрат соли малеиновой кислоты 5-[4-[2-(n-метил-n-(2-пиридил)амино) этокси]бензил]тиазолидин-2,4-диона в качестве фармацевтического препарата
UA63980C2 (en)	2004-02-16	A hydrate of 5-[4-[2-(n-methyl-n-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione, maleic acid salts
KR100755173B1 (ko)	2007-09-03	티아졸리딘디온 유도체의 타르트레이트 염
KR20010112446A (ko)	2001-12-20	티아졸리딘디온 유도체 및 그의 당뇨병약으로서의 용도
UA74003C2 (en)	2005-10-17	Hydrochloride salt of 5-[4-[2-(n-methyl-n-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione, a process for preparing thereof and a pharmaceutical composition
KR20040062965A (ko)	2004-07-09	로시글리타존 에디실레이트 및 항당뇨제로서의 그의 용도
KR100769008B1 (ko)	2007-10-22	티아졸리딘디온 유도체 및 항당뇨병제로서 그의 용도
EA005408B1 (ru)	2005-02-24	Тартратная соль производного тиазолидиндиона
JP2004508367A (ja)	2004-03-18	チアゾリジンジオン誘導体および抗糖尿病薬としてのその使用
KR100754701B1 (ko)	2007-09-03	티아졸리딘디온 유도체의 타르타르산염
KR20030022356A (ko)	2003-03-15	티아졸리딘디온 유도체의 타르타르산염
KR100822135B1 (ko)	2008-04-15	티아졸리딘디온 유도체 및 항당뇨제로서의 그의 용도
EA004298B1 (ru)	2004-02-26	Гидроиодид 5-[4-[2-(n-метил-n-(2-пиридил)амино)этокси]бензил]тиазолидин-2,4-диона в качестве фармацевтического препарата