OA11871A - Novel pharmaceutical. - Google Patents
Novel pharmaceutical. Download PDFInfo
- Publication number
- OA11871A OA11871A OA1200100275A OA1200100275A OA11871A OA 11871 A OA11871 A OA 11871A OA 1200100275 A OA1200100275 A OA 1200100275A OA 1200100275 A OA1200100275 A OA 1200100275A OA 11871 A OA11871 A OA 11871A
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- Prior art keywords
- polymorph
- provides
- compound
- polymorph according
- containing peaks
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims abstract description 34
- 238000000634 powder X-ray diffraction Methods 0.000 claims abstract description 15
- 239000000126 substance Substances 0.000 claims abstract description 8
- 238000001237 Raman spectrum Methods 0.000 claims abstract description 5
- 238000004519 manufacturing process Methods 0.000 claims abstract description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
- 239000003814 drug Substances 0.000 claims abstract description 3
- 238000002329 infrared spectrum Methods 0.000 claims abstract description 3
- 238000000279 solid-state nuclear magnetic resonance spectrum Methods 0.000 claims abstract 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 238000011282 treatment Methods 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 238000011321 prophylaxis Methods 0.000 claims description 7
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 5
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 5
- 239000011976 maleic acid Substances 0.000 claims description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 5
- 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 4
- 239000002002 slurry Substances 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 2
- 231100000252 nontoxic Toxicity 0.000 claims description 2
- 230000003000 nontoxic effect Effects 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 4
- 229940075894 denatured ethanol Drugs 0.000 claims 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims 1
- 206010010144 Completed suicide Diseases 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 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 claims 1
- 229920000642 polymer Polymers 0.000 claims 1
- 150000002688 maleic acid derivatives Chemical class 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 14
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- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
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- 239000000945 filler Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
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- 239000003826 tablet Substances 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 102000004877 Insulin Human genes 0.000 description 2
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- 208000008589 Obesity Diseases 0.000 description 2
- 238000001069 Raman spectroscopy Methods 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 239000003472 antidiabetic agent Substances 0.000 description 2
- 229940125708 antidiabetic agent Drugs 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- -1 colourants Substances 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000007884 disintegrant Substances 0.000 description 2
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- 239000007787 solid Substances 0.000 description 2
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- XUFXOAAUWZOOIT-SXARVLRPSA-N (2R,3R,4R,5S,6R)-5-[[(2R,3R,4R,5S,6R)-5-[[(2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-1-cyclohex-2-enyl]amino]-2-oxanyl]oxy]-3,4-dihydroxy-6-(hydroxymethyl)-2-oxanyl]oxy]-6-(hydroxymethyl)oxane-2,3,4-triol Chemical compound O([C@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O[C@H]1O[C@@H]([C@H]([C@H](O)[C@H]1O)N[C@@H]1[C@@H]([C@@H](O)[C@H](O)C(CO)=C1)O)C)[C@@H]1[C@@H](CO)O[C@@H](O)[C@H](O)[C@H]1O XUFXOAAUWZOOIT-SXARVLRPSA-N 0.000 description 1
- 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
- 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
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- 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
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- 239000004471 Glycine Substances 0.000 description 1
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- 206010060378 Hyperinsulinaemia Diseases 0.000 description 1
- 206010020710 Hyperphagia Diseases 0.000 description 1
- 229940122199 Insulin secretagogue Drugs 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
- 241000124008 Mammalia Species 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
- 229920002472 Starch Polymers 0.000 description 1
- 229940123464 Thiazolidinedione Drugs 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 229960002632 acarbose Drugs 0.000 description 1
- XUFXOAAUWZOOIT-UHFFFAOYSA-N acarviostatin I01 Natural products OC1C(O)C(NC2C(C(O)C(O)C(CO)=C2)O)C(C)OC1OC(C(C1O)O)C(CO)OC1OC1C(CO)OC(O)C(O)C1O XUFXOAAUWZOOIT-UHFFFAOYSA-N 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
- 239000003888 alpha glucosidase inhibitor 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
- 208000022531 anorexia Diseases 0.000 description 1
- 230000036528 appetite Effects 0.000 description 1
- 235000019789 appetite Nutrition 0.000 description 1
- 229940125388 beta agonist Drugs 0.000 description 1
- 150000004283 biguanides Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
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- 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
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- 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
- 238000001035 drying Methods 0.000 description 1
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- 239000003995 emulsifying agent Substances 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
- 239000003925 fat Substances 0.000 description 1
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- 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
- 239000011521 glass Substances 0.000 description 1
- 206010061989 glomerulosclerosis Diseases 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 230000000055 hyoplipidemic effect Effects 0.000 description 1
- 201000001421 hyperglycemia Diseases 0.000 description 1
- 230000035879 hyperinsulinaemia Effects 0.000 description 1
- 239000005555 hypertensive agent Substances 0.000 description 1
- 230000002218 hypoglycaemic effect Effects 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 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
- 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
- 238000002156 mixing Methods 0.000 description 1
- 239000002687 nonaqueous vehicle Substances 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
- 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
- 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
- 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
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- 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
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/427—Thiazoles not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Urology & Nephrology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Hematology (AREA)
- Child & Adolescent Psychology (AREA)
- Vascular Medicine (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Steroid Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Claims (13)
11 CLAIMS 118 7 1
1. A polymorphie form of 5-[4-[2-(N-methyl-N-(2- pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione, maleic acid sait (the "Polymorph") characterised in that it: (i) provides an infra red spectrum containing peaks at 1360, 1326, 1241, 714 and669 cm'l; and/or (ii) provides a Raman spectrum containing peaks at 1581, 768, 670, 271 and 226cm" 1; and/or (iii) provides a solid-state nuclear magnetic résonance spectrum containing peaksat Chemical shifts substantially as set out in Table I; and/or (iv) provides an X-ray powder diffraction (XRPD) pattern containing peakssubstantially as set out in Table IL
2. A Polymorph according to claim 1, which provides an infra red spectrumsubstantially in accordance with Figure I.
3. A Polymorph according to claim 1 or claim 2, which provides a Ramanspectrum substantially in accordance with Figure II.
4. A Polymorph according to any on of daims 1 to 3, which provides a solid-state nuclear magnetic résonance spectrum substantially in accordance with Figure III.
5. A Polymorph according to any one of daims 1 to 4, which provides an X-raypowder diffraction (XRPD) pattern substantially in accordance with Figure IV.
6. A Polymorph according to any one of daims 1 to 5, in isolated form.
7. A Polymorph according to any one of daims 1 to 6, in pure form.
8. A Polymorph according to any one of daims 1 to 7, in crystalline form.
9. A process for preparing a Polymorph according to daim 1, characterised inthat: (a) a slurry of 5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine- 2,4-dione, maleic acid sait (hereinafter also referred to as "Compound (1)" or the"Original Polymorph") in aqueous éthanol containing up to about 2.5% w/v water, is 12 118 7 1 heated for an extended period of time; after which time the Polymorph is recoveredfrom the denatured éthanol; or (b) Compound (I) is admixed with denatured éthanol, heated to an elevatedtempérature, over an extended period of time, after which time the Polymorph isrecovered from the solvent; or (c) Compound (I) in denatured éthanol containing up to 2.5% w/v water at 55°C isseeded with the Polymorph then cooled to a température in the range of from 20°C to25°C to provide the Polymorph; the Polymorph is then recovered from the solvent..
10. A pharmaceutical composition comprising an effective, non-toxic amount of aPolymorph according to claim 1 and a pharmaceutically acceptable carrier therefor.
11. A Polymorph according to claim 1, for use as an active therapeutic substance.
12. A Polymorph according to claim 1, for use in the treatment and/or prophylaxisof diabètes mellitus, conditions associated with diabètes mellitus and certaincomplications thereof.
13. The use of Polymorph for the manufacture of a médicament for the treatmentand/or prophylaxis of diabètes mellitus, conditions associated with diabètes mellitusand certain complications thereof.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9909472.4A GB9909472D0 (en) | 1999-04-23 | 1999-04-23 | Novel compounds |
| GBGB9912197.2A GB9912197D0 (en) | 1999-05-25 | 1999-05-25 | Novel pharmaceutical |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| OA11871A true OA11871A (en) | 2006-03-27 |
Family
ID=26315460
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| OA1200100275A OA11871A (en) | 1999-04-23 | 2000-04-19 | Novel pharmaceutical. |
Country Status (40)
| Country | Link |
|---|---|
| US (2) | US6815457B1 (fr) |
| EP (3) | EP1903043A1 (fr) |
| JP (1) | JP2002543075A (fr) |
| KR (1) | KR100744359B1 (fr) |
| CN (1) | CN1208335C (fr) |
| AP (1) | AP1495A (fr) |
| AR (2) | AR023568A1 (fr) |
| AT (2) | ATE382046T1 (fr) |
| AU (1) | AU765498B2 (fr) |
| BG (1) | BG65427B1 (fr) |
| BR (1) | BR0009934A (fr) |
| CA (1) | CA2370258A1 (fr) |
| CO (1) | CO5170424A1 (fr) |
| CY (1) | CY1107238T1 (fr) |
| CZ (1) | CZ20013799A3 (fr) |
| DE (2) | DE60037602T2 (fr) |
| DK (2) | DK1173434T3 (fr) |
| DZ (1) | DZ3155A1 (fr) |
| EA (1) | EA004534B1 (fr) |
| ES (2) | ES2298327T3 (fr) |
| HK (1) | HK1045154B (fr) |
| HR (1) | HRP20010773B1 (fr) |
| HU (1) | HUP0200929A3 (fr) |
| IL (1) | IL146110A0 (fr) |
| MA (1) | MA26785A1 (fr) |
| MX (1) | MXPA01010820A (fr) |
| MY (1) | MY128007A (fr) |
| NO (1) | NO320589B1 (fr) |
| NZ (1) | NZ515163A (fr) |
| OA (1) | OA11871A (fr) |
| PE (1) | PE20010040A1 (fr) |
| PL (1) | PL351686A1 (fr) |
| PT (2) | PT1284268E (fr) |
| RS (1) | RS50114B (fr) |
| SK (1) | SK286423B6 (fr) |
| TR (1) | TR200103061T2 (fr) |
| TW (1) | TW591027B (fr) |
| UA (1) | UA67843C2 (fr) |
| UY (1) | UY26120A1 (fr) |
| WO (1) | WO2000064892A2 (fr) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 |
| CN1167702C (zh) | 1999-04-23 | 2004-09-22 | 史密丝克莱恩比彻姆有限公司 | 5-[4-[2-n-甲基-n-(2-吡啶基)氨基]乙氧基]苄基]噻唑烷-2,4-二酮马来酸盐的多晶型物 |
| US20040248945A1 (en) | 1999-04-23 | 2004-12-09 | Smithkline Beecham P.L.C. | Thiazolidinedione derivative and its use as antidiabetic |
| RS50114B (sr) | 1999-04-23 | 2009-03-25 | Smithkline Beecham P.L.C., | Novi polimorfni oblik 5-/4-/2-(n-metil- n-(2-piridil)amino/ etoksi/benzil/ tiazolidin-2,4-dion, soli maleinske kiseline |
| GB0006133D0 (en) | 2000-03-14 | 2000-05-03 | Smithkline Beecham Plc | Novel pharmaceutical |
| US7241895B2 (en) * | 2000-09-26 | 2007-07-10 | Dr. Reddy's Laboratories Limited | Polymorphic forms of 5-[4-[2-[n-methyl-n-(2-pyridyl)amino[ethoxy]benzyl] thiazolidine-2,4-dione maleate and process for their preparation |
| AU9123201A (en) * | 2000-09-26 | 2002-04-08 | Reddy S Res Foundation | Novel polymorphic forms of 5-(4-(2-(N-methyl-N-(2-pyridyl)amino)ethoxy)benzyl) thiazolidine-2,4-dione maleate and process for their preparation |
| WO2003050116A1 (fr) * | 2001-12-13 | 2003-06-19 | Smithkline Beecham Plc | Sel d'acide 10-camphorsulphonique de 5(-4-(2-(n-methyl-n-(2-pyridil)amino)ethoxy)benzyl)thiazolidine-2,4-dione et son utilisation contre le diabete sucre |
| GB0130511D0 (en) * | 2001-12-20 | 2002-02-06 | Smithkline Beecham Plc | Novel pharmaceutical |
| WO2003053962A1 (fr) * | 2001-12-20 | 2003-07-03 | Smithkline Beecham Plc | Sel d'acide malique 5-(4-(2-(n-methyl-n-(2-pyridyl)amino)ethoxy) benzyl) thiazolidine-2, 4-dione et son utilisation contre le diabete sucre |
| GB0307259D0 (en) * | 2003-03-28 | 2003-05-07 | Glaxo Group Ltd | Process |
| EP1468997A3 (fr) * | 2003-04-18 | 2004-11-03 | CHEMI S.p.A. | Formes polymorphes de maléate de rosiglitatone |
| GB2405403A (en) * | 2003-08-29 | 2005-03-02 | Cipla Ltd | Rosiglitazone maleate of particular polymorphic forms and methods of preparing rosiglitazone free base |
| EP1709038A2 (fr) * | 2004-01-28 | 2006-10-11 | Usv Limited | Procede de preparation de maleate de 5- 4- 2- n-methyl-n-(2-pyridyl) amino¨ ethoxy¨ phenyl methyl¨ thiazolidine-2, 4-dione |
| ITMI20041537A1 (it) * | 2004-07-28 | 2004-10-28 | Chemi Spa | Nuova forma polimorfa del rosiglitazone maleato |
| CZ298424B6 (cs) * | 2005-05-24 | 2007-09-26 | Zentiva, A. S. | Zpusob krystalizace rosiglitazonu a jeho derivátuze smesných rozpouštedel |
| 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 |
| US20090076093A1 (en) * | 2007-09-14 | 2009-03-19 | Protia, Llc | Deuterium-enriched rosiglitazone |
| EP2184055A1 (fr) | 2008-11-07 | 2010-05-12 | LEK Pharmaceuticals d.d. | Procédé de préparation de formes galéniques solides de maléate de rosiglitazone |
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| EP0842925A1 (fr) | 1987-09-04 | 1998-05-20 | Beecham Group Plc | Thiazolidinédiones substituées |
| US6288095B1 (en) | 1987-09-04 | 2001-09-11 | Beecham Group P.L.C. | Compounds |
| GB9124513D0 (en) | 1991-11-19 | 1992-01-08 | Smithkline Beecham Plc | Novel process |
| GB9218830D0 (en) * | 1992-09-05 | 1992-10-21 | Smithkline Beecham Plc | Novel compounds |
| US5741803A (en) | 1992-09-05 | 1998-04-21 | Smithkline Beecham Plc | Substituted thiazolidinedionle derivatives |
| US5457109A (en) * | 1993-09-15 | 1995-10-10 | Warner-Lambert Company | Use of thiazolidinedione derivatives and related antihyperglycemic agents in the treatment of disease states at risk for progressing to noninsulin-dependent diabetes mellitus |
| DE4404198A1 (de) | 1994-02-10 | 1995-08-17 | Henkel Kgaa | 2-Fluor-6-nitroaniline |
| SG47100A1 (en) | 1994-02-10 | 1998-03-20 | Smithkline Beecham Plc | Use of insulin sensitisers for treating renal diseases |
| US20010044458A1 (en) * | 1994-02-10 | 2001-11-22 | Smithkline Beechamp P.L.C. | Use of insulin sensitisers for treating renal diseases |
| TWI238064B (en) * | 1995-06-20 | 2005-08-21 | Takeda Chemical Industries Ltd | A pharmaceutical composition for prophylaxis and treatment of diabetes |
| US6153632A (en) * | 1997-02-24 | 2000-11-28 | Rieveley; Robert B. | Method and composition for the treatment of diabetes |
| GB9711683D0 (en) | 1997-06-05 | 1997-08-06 | Smithkline Beecham Plc | Composition |
| GB9712866D0 (en) | 1997-06-18 | 1997-08-20 | Smithkline Beecham Plc | Novel method of treatment |
| US20020004515A1 (en) * | 1997-06-18 | 2002-01-10 | Smith Stephen Alistair | Treatment of diabetes with thiazolidinedione and metformin |
| CN1168451C (zh) | 1997-06-18 | 2004-09-29 | 史密丝克莱恩比彻姆有限公司 | 噻唑烷二酮和磺酰脲组合物在制备治疗糖尿病的药物中的用途 |
| CN1114404C (zh) | 1997-06-18 | 2003-07-16 | 史密丝克莱恩比彻姆有限公司 | 用噻唑烷二酮和二甲双胍治疗糖尿病 |
| US20020028768A1 (en) * | 1997-06-18 | 2002-03-07 | Smithkline Beecham P.L.C. | Treatment of diabetes with rosiglitazone and insulin |
| US20010049380A1 (en) * | 1997-06-18 | 2001-12-06 | Smith Stephen Alistair | Treatment of diabetes with thiazolidinedione and sulphonylurea |
| CA2294134A1 (fr) | 1997-06-18 | 1998-12-23 | Stephen Alistair Smith | Traitement du diabete a l'aide de thiazolidinedione et d'un inhibiteur des alpha-glucosidases |
| US20020045649A1 (en) * | 1997-07-18 | 2002-04-18 | Smithkline Beecham P.L.C. | Treatment of diabetes with thiazolidinedione and sulphonylurea |
| US20020016287A1 (en) * | 1997-07-18 | 2002-02-07 | Smithkline Beecham P.L.C. | Treatment of diabetes with thiazolidinedione, insulin secretagogue and diguanide |
| GB9726568D0 (en) | 1997-12-16 | 1998-02-11 | Smithkline Beecham Plc | Novel pharmaceutical |
| GB9726566D0 (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 |
| GB9726563D0 (en) | 1997-12-16 | 1998-02-11 | Smithkline Beecham Plc | Novel pharmaceutical |
| RS50114B (sr) | 1999-04-23 | 2009-03-25 | Smithkline Beecham P.L.C., | Novi polimorfni oblik 5-/4-/2-(n-metil- n-(2-piridil)amino/ etoksi/benzil/ tiazolidin-2,4-dion, soli maleinske kiseline |
| EA003031B1 (ru) | 1999-04-23 | 2002-12-26 | Смитклайн Бичам Плс | Новый фармацевтический препарат |
| CN1167702C (zh) | 1999-04-23 | 2004-09-22 | 史密丝克莱恩比彻姆有限公司 | 5-[4-[2-n-甲基-n-(2-吡啶基)氨基]乙氧基]苄基]噻唑烷-2,4-二酮马来酸盐的多晶型物 |
| AU9123201A (en) | 2000-09-26 | 2002-04-08 | Reddy S Res Foundation | Novel polymorphic forms of 5-(4-(2-(N-methyl-N-(2-pyridyl)amino)ethoxy)benzyl) thiazolidine-2,4-dione maleate and process for their preparation |
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2000
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- 2000-04-19 JP JP2000614244A patent/JP2002543075A/ja active Pending
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- 2000-04-19 HR HR20010773A patent/HRP20010773B1/xx not_active IP Right Cessation
- 2000-04-19 US US10/030,323 patent/US6815457B1/en not_active Expired - Fee Related
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- 2000-04-19 WO PCT/GB2000/001514 patent/WO2000064892A2/fr not_active Ceased
- 2000-04-19 DK DK00920889T patent/DK1173434T3/da active
- 2000-04-19 CA CA002370258A patent/CA2370258A1/fr not_active Abandoned
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- 2000-04-19 EP EP07150378A patent/EP1903043A1/fr not_active Withdrawn
- 2000-04-19 ES ES02080320T patent/ES2298327T3/es not_active Expired - Lifetime
- 2000-04-19 DE DE60037602T patent/DE60037602T2/de not_active Expired - Fee Related
- 2000-04-19 HU HU0200929A patent/HUP0200929A3/hu not_active IP Right Cessation
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2001
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