DD259858A5 - Verfahren zur herstellung von kristallinem torasemid der modifikation i - Google Patents
Verfahren zur herstellung von kristallinem torasemid der modifikation i Download PDFInfo
- Publication number
- DD259858A5 DD259858A5 DD86293655A DD29365586A DD259858A5 DD 259858 A5 DD259858 A5 DD 259858A5 DD 86293655 A DD86293655 A DD 86293655A DD 29365586 A DD29365586 A DD 29365586A DD 259858 A5 DD259858 A5 DD 259858A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- modification
- torasemide
- rearrangement
- water
- melting point
- Prior art date
Links
- 230000004048 modification Effects 0.000 title claims abstract description 57
- 238000012986 modification Methods 0.000 title claims abstract description 57
- NGBFQHCMQULJNZ-UHFFFAOYSA-N Torsemide Chemical compound CC(C)NC(=O)NS(=O)(=O)C1=CN=CC=C1NC1=CC=CC(C)=C1 NGBFQHCMQULJNZ-UHFFFAOYSA-N 0.000 title claims abstract description 48
- 229960005461 torasemide Drugs 0.000 title claims abstract description 47
- 238000004519 manufacturing process Methods 0.000 title description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000000034 method Methods 0.000 claims abstract description 12
- 230000008707 rearrangement Effects 0.000 claims abstract description 11
- 238000002360 preparation method Methods 0.000 claims abstract description 10
- 230000008569 process Effects 0.000 claims abstract description 8
- 239000000725 suspension Substances 0.000 claims abstract description 8
- 230000003197 catalytic effect Effects 0.000 claims abstract 2
- 238000003756 stirring Methods 0.000 claims abstract 2
- 238000002844 melting Methods 0.000 claims description 8
- 230000008018 melting Effects 0.000 claims description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims 1
- 239000012670 alkaline solution Substances 0.000 claims 1
- 230000007935 neutral effect Effects 0.000 claims 1
- 230000001376 precipitating effect Effects 0.000 claims 1
- 239000011780 sodium chloride Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 10
- 239000013078 crystal Substances 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 238000004090 dissolution Methods 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 235000019359 magnesium stearate Nutrition 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 229920002261 Corn starch Polymers 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000008120 corn starch Substances 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-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
- 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 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000013459 approach Methods 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 230000001882 diuretic effect Effects 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 235000010980 cellulose Nutrition 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000002934 diuretic Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 238000001226 reprecipitation Methods 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229920000881 Modified starch Polymers 0.000 description 1
- 208000004880 Polyuria Diseases 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 235000019426 modified starch Nutrition 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000013094 purity test Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000002424 x-ray crystallography Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Hematology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Saccharide Compounds (AREA)
- Compounds Of Unknown Constitution (AREA)
- Enzymes And Modification Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19853529529 DE3529529A1 (de) | 1985-08-17 | 1985-08-17 | Verfahren zur herstellung einer stabilen modifikation von torasemid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD259858A5 true DD259858A5 (de) | 1988-09-07 |
Family
ID=6278766
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD86293655A DD259858A5 (de) | 1985-08-17 | 1986-08-14 | Verfahren zur herstellung von kristallinem torasemid der modifikation i |
Country Status (25)
| Country | Link |
|---|---|
| US (4) | US4743693A (en:Method) |
| EP (1) | EP0212537B1 (en:Method) |
| JP (2) | JPS6245576A (en:Method) |
| KR (1) | KR930009818B1 (en:Method) |
| AU (1) | AU573454B2 (en:Method) |
| CA (1) | CA1307277C (en:Method) |
| CS (2) | CS259891B2 (en:Method) |
| DD (1) | DD259858A5 (en:Method) |
| DE (2) | DE3529529A1 (en:Method) |
| DK (1) | DK162518C (en:Method) |
| ES (1) | ES2001522A6 (en:Method) |
| FI (1) | FI82189C (en:Method) |
| GR (1) | GR862139B (en:Method) |
| HK (1) | HK59994A (en:Method) |
| HU (1) | HU195778B (en:Method) |
| IE (1) | IE59237B1 (en:Method) |
| IL (1) | IL79672A (en:Method) |
| LT (1) | LT3596B (en:Method) |
| NO (1) | NO170079C (en:Method) |
| NZ (1) | NZ217172A (en:Method) |
| PL (1) | PL146086B1 (en:Method) |
| PT (1) | PT83186B (en:Method) |
| SU (1) | SU1480766A3 (en:Method) |
| UA (1) | UA7080A1 (en:Method) |
| ZA (1) | ZA866151B (en:Method) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3623620A1 (de) * | 1986-07-12 | 1988-01-21 | Boehringer Mannheim Gmbh | Spritzfertige, waessrige, alkalische injektionsloesungen von torasemid und verfahren zu ihrer herstellung |
| US5166162A (en) * | 1990-03-02 | 1992-11-24 | Adir Et Compagnie | Pyridylsulfonylurea and pyridylsulfonylthiourea compounds |
| JP3586471B2 (ja) * | 1991-06-25 | 2004-11-10 | 三菱ウェルファーマ株式会社 | トラセミド含有医薬組成物 |
| TW257757B (en:Method) * | 1993-03-03 | 1995-09-21 | Boehringer Mannheim Gmbh | |
| HRP980532B1 (en) | 1998-10-02 | 2005-06-30 | Pliva | Novel crystalline torasemide modification |
| US6166045A (en) | 1998-06-02 | 2000-12-26 | Roche Diagnostics Gmbh | Torasemide of modification III |
| US5914336A (en) | 1998-06-02 | 1999-06-22 | Boehringer Mannheim Gmbh | Method of controlling the serum solubility of orally administered torasemide and composition relating thereto |
| US20030026835A1 (en) * | 1999-02-15 | 2003-02-06 | Sumitomo Pharmaceuticals Company Limited | Tablets disintegrating rapidly in the oral cavity |
| HRP20020120A2 (en) | 1999-08-11 | 2003-10-31 | Teva Pharma | Torsemide polymorphs |
| EP1292303B1 (en) * | 2000-02-17 | 2004-05-12 | Teva Pharmaceutical Industries Ltd. | A stable pharmaceutical formulation comprising torsemide modification ii |
| NZ521852A (en) | 2000-03-20 | 2004-10-29 | Teva Pharma | Novel processes for preparing torsemide intermediate |
| HRP20000162B1 (en) * | 2000-03-20 | 2004-06-30 | Pliva D D | Amorphous torasemide modification |
| HRP20000765A2 (en) * | 2000-11-10 | 2002-06-30 | Pliva D D | Compositions of n-(1-methylethylaminocarbonyl)-4-(3-methylphenylamino)-3-pyridylsulfonamide and cyclic oligosaccharides with increased release |
| US20030022921A1 (en) * | 2001-02-21 | 2003-01-30 | Minutza Leibovici | Stable pharmaceutical formulation comprising torsemide modification II |
| IN192178B (en:Method) * | 2001-08-03 | 2004-03-06 | Ranbaxy Lab | |
| JP4625637B2 (ja) | 2002-02-22 | 2011-02-02 | シャイア エルエルシー | 活性物質送達系及び活性物質を保護し投与する方法 |
| ITMI20020639A1 (it) * | 2002-03-27 | 2003-09-29 | Cosma S P A | Composizioni farmaceutiche comprendenti come principio attivo 1-isopropil-3°(4-m-toluidino-3-pridil)sulfonil!-urea |
| HRP20020603B1 (en) * | 2002-07-19 | 2008-11-30 | Pliva D.D. | New process for the preparation of modification i n-(1-methylethylaminocarbonyl)-4-(3-methylphenylamino)-3-pyridinesulfonamide |
| DE60312953T2 (de) * | 2002-11-18 | 2007-12-13 | Teva Pharmaceutical Industries Ltd. | Stabiles lansoprazol, enthaltend mehr als 500 ppm bis zu 3000 ppm wasser und mehr als 200 ppm bis zu 5000 ppm alkohol |
| CA2515130A1 (en) * | 2003-02-05 | 2004-08-26 | Teva Pharmaceutical Industries Ltd. | Method of stabilizing lansoprazole |
| ES2244324B1 (es) * | 2004-03-25 | 2006-11-16 | Ferrer Internacional, S.A. | Composiciones diureticas de liberacion prolongada. |
| AT500576B1 (de) * | 2004-07-28 | 2006-11-15 | Sanochemia Pharmazeutika Ag | Verfahren zur reindarstellung von kristallformen von torsemid |
| US10178893B1 (en) * | 2013-06-14 | 2019-01-15 | Scott Bradley Baker | Shoe |
| FR3018688A1 (fr) * | 2014-03-19 | 2015-09-25 | Virbac | Utilisation de torasemide a faible dose dans une composition veterinaire |
| US12048677B2 (en) | 2014-12-12 | 2024-07-30 | Ceva Sante Animale | Compositions and uses thereof for the treatment of heart failure in domestic animals |
| EP3031471A1 (en) * | 2014-12-12 | 2016-06-15 | Ceva Sante Animale | Veterinary composition for the treatment of pulmonary edema associated with heart failure in domestic animals |
| SI3173075T1 (sl) * | 2015-11-27 | 2019-02-28 | Accupharma Spolka Z Ograniczona Odpowiedzialnoscia | Farmacevtski kombinacijski pripravek inhibitorja ACE in diuretika zanke |
| CN115417810B (zh) * | 2022-09-22 | 2023-10-10 | 南京正科医药股份有限公司 | 一种托拉塞米晶型ⅰ的精制方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US30633A (en) * | 1860-11-13 | Improvement in fire-escapes | ||
| GB1477664A (en) * | 1974-04-17 | 1977-06-22 | Christiaens Sa A | Pyridine derivatives |
| GB1593609A (en) * | 1978-01-31 | 1981-07-22 | Christiaens Sa A | Pyridine sulfonamides |
| LU85193A1 (fr) * | 1984-01-31 | 1985-09-12 | Christiaens Sa A | Nouveaux derives de la 4-phenylaminopyridine,leur utilisation et leur preparation |
-
1985
- 1985-08-17 DE DE19853529529 patent/DE3529529A1/de active Granted
-
1986
- 1986-08-10 IL IL79672A patent/IL79672A/xx not_active IP Right Cessation
- 1986-08-11 CS CS865945A patent/CS259891B2/cs not_active IP Right Cessation
- 1986-08-11 CA CA000515676A patent/CA1307277C/en not_active Expired - Lifetime
- 1986-08-11 US US06/895,355 patent/US4743693A/en not_active Ceased
- 1986-08-11 AU AU61055/86A patent/AU573454B2/en not_active Expired
- 1986-08-12 EP EP86111118A patent/EP0212537B1/de not_active Expired - Lifetime
- 1986-08-12 NZ NZ217172A patent/NZ217172A/xx unknown
- 1986-08-12 DE DE8686111118T patent/DE3667970D1/de not_active Expired - Lifetime
- 1986-08-12 PT PT83186A patent/PT83186B/pt unknown
- 1986-08-13 IE IE217986A patent/IE59237B1/en not_active IP Right Cessation
- 1986-08-13 DK DK385586A patent/DK162518C/da not_active IP Right Cessation
- 1986-08-14 DD DD86293655A patent/DD259858A5/de not_active IP Right Cessation
- 1986-08-14 KR KR1019860006689A patent/KR930009818B1/ko not_active Expired - Lifetime
- 1986-08-14 ES ES8601131A patent/ES2001522A6/es not_active Expired
- 1986-08-14 GR GR862139A patent/GR862139B/el unknown
- 1986-08-15 HU HU863598A patent/HU195778B/hu unknown
- 1986-08-15 PL PL1986261052A patent/PL146086B1/pl unknown
- 1986-08-15 SU SU864027953A patent/SU1480766A3/ru active
- 1986-08-15 NO NO863305A patent/NO170079C/no not_active IP Right Cessation
- 1986-08-15 ZA ZA866151A patent/ZA866151B/xx unknown
- 1986-08-15 UA UA4027953A patent/UA7080A1/uk unknown
- 1986-08-15 FI FI863305A patent/FI82189C/fi not_active IP Right Cessation
- 1986-08-18 JP JP61191789A patent/JPS6245576A/ja active Granted
-
1987
- 1987-10-20 US US07/111,439 patent/US4822807A/en not_active Ceased
-
1989
- 1989-10-27 JP JP1278800A patent/JPH0643400B2/ja not_active Expired - Lifetime
-
1991
- 1991-12-31 CS CS914199A patent/CS419991A3/cs unknown
-
1992
- 1992-12-03 US US07/985,053 patent/USRE34580E/en not_active Expired - Lifetime
-
1993
- 1993-04-08 US US08/043,631 patent/USRE34672E/en not_active Expired - Lifetime
- 1993-08-27 LT LTIP898A patent/LT3596B/lt not_active IP Right Cessation
-
1994
- 1994-06-23 HK HK59994A patent/HK59994A/xx not_active IP Right Cessation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ENJ | Ceased due to non-payment of renewal fee |