EA010176B1 - Соль фосфорной кислоты и 5-[4-[2-(n-метил-n-(2-пиридил)амино)этокси]бензил]тиазолидин-2,4-диона и способ её получения - Google Patents
Соль фосфорной кислоты и 5-[4-[2-(n-метил-n-(2-пиридил)амино)этокси]бензил]тиазолидин-2,4-диона и способ её получения Download PDFInfo
- Publication number
- EA010176B1 EA010176B1 EA200700003A EA200700003A EA010176B1 EA 010176 B1 EA010176 B1 EA 010176B1 EA 200700003 A EA200700003 A EA 200700003A EA 200700003 A EA200700003 A EA 200700003A EA 010176 B1 EA010176 B1 EA 010176B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- salt
- phosphoric acid
- dione
- ethoxy
- benzyl
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims abstract description 86
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 title claims abstract description 68
- 229910000147 aluminium phosphate Inorganic materials 0.000 title claims abstract description 32
- 238000000034 method Methods 0.000 title claims description 21
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 title 1
- 239000012453 solvate Substances 0.000 claims abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 31
- 239000000243 solution Substances 0.000 claims description 25
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 18
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 13
- 239000002245 particle Substances 0.000 claims description 13
- 229910019142 PO4 Inorganic materials 0.000 claims description 12
- 238000002844 melting Methods 0.000 claims description 11
- 230000008018 melting Effects 0.000 claims description 11
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 11
- 239000010452 phosphate Substances 0.000 claims description 11
- ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 claims description 10
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 239000007787 solid Substances 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 238000001228 spectrum Methods 0.000 claims description 6
- 238000000113 differential scanning calorimetry Methods 0.000 claims description 5
- 238000002441 X-ray diffraction Methods 0.000 claims description 4
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 4
- 230000002058 anti-hyperglycaemic effect Effects 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 239000012535 impurity Substances 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 238000001394 phosphorus-31 nuclear magnetic resonance spectrum Methods 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- 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 abstract description 115
- 229960004586 rosiglitazone Drugs 0.000 description 43
- 235000011007 phosphoric acid Nutrition 0.000 description 30
- 239000000126 substance Substances 0.000 description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- 239000012458 free base Substances 0.000 description 11
- 235000021317 phosphate Nutrition 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 238000009835 boiling Methods 0.000 description 8
- 238000003756 stirring Methods 0.000 description 7
- 238000001035 drying Methods 0.000 description 6
- 239000012065 filter cake Substances 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 238000009826 distribution Methods 0.000 description 5
- KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 description 4
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 4
- 230000003993 interaction Effects 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000005388 cross polarization Methods 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- SUFUKZSWUHZXAV-BTJKTKAUSA-N rosiglitazone maleate Chemical compound [H+].[H+].[O-]C(=O)\C=C/C([O-])=O.C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O SUFUKZSWUHZXAV-BTJKTKAUSA-N 0.000 description 3
- 229960003271 rosiglitazone maleate Drugs 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000013256 coordination polymer Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- -1 ethyl acetate) Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 238000000634 powder X-ray diffraction Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 239000004254 Ammonium phosphate Substances 0.000 description 1
- 240000006890 Erythroxylum coca Species 0.000 description 1
- 101150117096 GSG1 gene Proteins 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 238000005004 MAS NMR spectroscopy Methods 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- 101100020663 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) ppm-1 gene Proteins 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910000148 ammonium phosphate Inorganic materials 0.000 description 1
- 235000019289 ammonium phosphates Nutrition 0.000 description 1
- 239000003472 antidiabetic agent Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 235000008957 cocaer Nutrition 0.000 description 1
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical group [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 210000002249 digestive system Anatomy 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 201000001421 hyperglycemia Diseases 0.000 description 1
- 238000002329 infrared spectrum Methods 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
- 239000000463 material Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 1
- 238000005303 weighing 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
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Emergency Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Endocrinology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CZ20040712A CZ296468B6 (cs) | 2004-06-10 | 2004-06-10 | Sul kyseliny fosforecné s 5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidin-2,4-dionema zpusob její prípravy |
| PCT/CZ2005/000040 WO2005121136A1 (en) | 2004-06-10 | 2005-05-25 | Salt of phosphoric acid with 5-[4-[2-(n-methyl-n-(2-pyridyl)amino)-ethoxy] benzy] thiazolidin-2,4-dione and a method of its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA200700003A1 EA200700003A1 (ru) | 2007-04-27 |
| EA010176B1 true EA010176B1 (ru) | 2008-06-30 |
Family
ID=34981408
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA200700003A EA010176B1 (ru) | 2004-06-10 | 2005-05-25 | Соль фосфорной кислоты и 5-[4-[2-(n-метил-n-(2-пиридил)амино)этокси]бензил]тиазолидин-2,4-диона и способ её получения |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP1756100A1 (cs) |
| CZ (1) | CZ296468B6 (cs) |
| EA (1) | EA010176B1 (cs) |
| UA (1) | UA87855C2 (cs) |
| WO (1) | WO2005121136A1 (cs) |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0306228A1 (en) * | 1987-09-04 | 1989-03-08 | Beecham Group Plc | Substituted thiazolidinedione derivatives |
| WO1994005659A1 (en) * | 1992-09-05 | 1994-03-17 | Smithkline Beecham Plc | Substituted thiazolidinedione derivatives |
| WO2000063205A2 (en) * | 1999-04-20 | 2000-10-26 | Smithkline Beecham P.L.C. | Thiazolidinedione derivative and its use as antidiabetic |
| WO2003050113A1 (en) * | 2001-12-13 | 2003-06-19 | Smithkline Beecham Plc | Hydrogensulfate salt of 5-'4-'2-(n-methyl-n-(2-pyridyl)amino)ethoxy!benzyl!thia zolidine-2,4-dione |
| WO2005023803A1 (en) * | 2003-09-10 | 2005-03-17 | Biocon Limited | Phosphoric acid salt of 5-[[4-[2-(methyl-2-pyridinylamino) ethoxy] phenyl] methyl]- 2,4-thiazolidinedione |
| GB2410948A (en) * | 2004-02-13 | 2005-08-17 | Sandoz Ag | Novel phosphoric acid salt of rosiglitazone |
-
2004
- 2004-06-10 CZ CZ20040712A patent/CZ296468B6/cs not_active IP Right Cessation
-
2005
- 2005-05-25 EA EA200700003A patent/EA010176B1/ru not_active IP Right Cessation
- 2005-05-25 UA UAA200700258A patent/UA87855C2/ru unknown
- 2005-05-25 WO PCT/CZ2005/000040 patent/WO2005121136A1/en active Application Filing
- 2005-05-25 EP EP05741667A patent/EP1756100A1/en not_active Withdrawn
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0306228A1 (en) * | 1987-09-04 | 1989-03-08 | Beecham Group Plc | Substituted thiazolidinedione derivatives |
| WO1994005659A1 (en) * | 1992-09-05 | 1994-03-17 | Smithkline Beecham Plc | Substituted thiazolidinedione derivatives |
| WO2000063205A2 (en) * | 1999-04-20 | 2000-10-26 | Smithkline Beecham P.L.C. | Thiazolidinedione derivative and its use as antidiabetic |
| WO2003050113A1 (en) * | 2001-12-13 | 2003-06-19 | Smithkline Beecham Plc | Hydrogensulfate salt of 5-'4-'2-(n-methyl-n-(2-pyridyl)amino)ethoxy!benzyl!thia zolidine-2,4-dione |
| WO2005023803A1 (en) * | 2003-09-10 | 2005-03-17 | Biocon Limited | Phosphoric acid salt of 5-[[4-[2-(methyl-2-pyridinylamino) ethoxy] phenyl] methyl]- 2,4-thiazolidinedione |
| GB2410948A (en) * | 2004-02-13 | 2005-08-17 | Sandoz Ag | Novel phosphoric acid salt of rosiglitazone |
Non-Patent Citations (1)
| Title |
|---|
| SORBERA L.A. ET AL.: "ROSIGLITAZONE MALEATE" DRUGS OF THE FUTURE, BARCELONA, ES, vol. 23, no. 9, 1998, pages 977-985, XP000856586 ISSN: 0377-8282 the whole document * |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2005121136A1 (en) | 2005-12-22 |
| EA200700003A1 (ru) | 2007-04-27 |
| UA87855C2 (en) | 2009-08-25 |
| CZ2004712A3 (cs) | 2006-01-11 |
| EP1756100A1 (en) | 2007-02-28 |
| CZ296468B6 (cs) | 2006-03-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Lapse of a eurasian patent due to non-payment of renewal fees within the time limit in the following designated state(s) |
Designated state(s): AM AZ KG MD TJ TM |
|
| MM4A | Lapse of a eurasian patent due to non-payment of renewal fees within the time limit in the following designated state(s) |
Designated state(s): BY KZ RU |