USRE34672E - Pharmaceutical composition containing a stable modification of torasemide - Google Patents
Pharmaceutical composition containing a stable modification of torasemide Download PDFInfo
- Publication number
- USRE34672E USRE34672E US08/043,631 US4363193A USRE34672E US RE34672 E USRE34672 E US RE34672E US 4363193 A US4363193 A US 4363193A US RE34672 E USRE34672 E US RE34672E
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- United States
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- modification
- torasemide
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- melting point
- iaddend
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- 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
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- 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)
- Saccharide Compounds (AREA)
- Compounds Of Unknown Constitution (AREA)
- Enzymes And Modification Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Abstract
The present invention provides a process for the preparation of cystalline torasemide in the pure modification I (monoclinic, space group P21 /c, melting point 162° C.) from torasemide of modification II (monoclinic, space group P2/n, melting point 169° C.), wherein a suspension of torasemide of modification II is stirred in water with the addition of a catalytic amount of modification I until the rearrangement is complete.
The present invention also provides pharmaceutical compositions containing torasemide of modification I.
Description
.[.This is a Divisional of Ser. No. 895,355, filed Aug. 11, 1986 now U.S. Pat. No. 4,243,693..].
This application is a continuation of Ser. No. 07/691,340, filed Apr. 18, 1991 (now abandoned), which is a REISSUE of Ser. No. 07/111,439, filed Oct. 20, 1987, (U.S. Pat. No. 4,822,807), which is a divisional of Ser. No. 06/895,355, filed Aug. 11, 1986 (U.S. Pat. No. 4,793,693). .Iaddend.
The present invention is concerned with a process for the preparation of a stable modification of torasemide.
Torasemide (1-isopropyl-3-[(4-m-toluidino-3-pyridyl)-sulphonyl]-urea) is a compound with interesting pharamacological properties which is described in Example 71 of U.S. Pat. No. Re 30,633 as 3-isopropylcarbamyl sulfonamide-4-(3'-methyl)-phenylaminopyridine. In particular, this compound has a strong diuretic action in the case of which water and sodium ions are excreted relatively more strongly than potassium ions. The compound is, therefore, of great interest as a diuretic agent.
In the preparation of this compound, a purification is normally included in which the compound in question is dissolved in an aqueous or aqueous alcoholic solution of sodium hydrogen carbonate and, after filtering off from impurities, the torasemide is again precipitated out with acetic acid or carbon dioxide. In the case of this process, the product is obtained in the form of white crystals with a melting point of 163°-164° C.
From Acta Cryst. 1978, pp. 2659-2662 and Acta Cryst., 1978, pp. 1304-1310, it is known that torasemide can occur in two modifications which differ X-ray crystallographically. Both modifications are simultaneously present when a solution of torasemide in petroleum ether/ethanol is slowly evaporated. The crystals, which are characterised not only as prisms with a melting point of 169° C. but also as leaflets with a melting point of 162° C., are, however, only described in these literature references with regard to their X-ray crystallographic properties. The modification with the melting point of 169° C., which is hereinafter referred to as modification I, crystallises monoclonically in the space group P21 /c, and the modification with the melting point of 162° C., which is hereinafter referred to as modification II, crystallises monoclinically in the space group P2/n.
The modification obtained in the case of the preparation and normal purification by precipitating the torasemide with carbon dioxide is modification II which usually also results in the case of recrystallisations from other solvents. Since this form, in the case of storage of the pure active material, does not change and, in the case of all purification experiments, forms the predominant form, it was assumed that this modification II is also stable. Surprisingly, we have now ascertained that torasemide of modification II, when it is present in very finely divided form in pharmaceutical tablets, rearranges more or less quickly into modification I, whereby the crystal size and speed of dissolving of the active material upon introducing the tablets into water can be significantly changed. Since, on the other hand, as is known, the speed of dissolving represents one of the important characteristics of a pharmaceutical form of administration and thus, in order to be able to dose reproducibly, must not differ from one tablet to another, the problem exists of finding a form of administration of torasemide which does not change its speed of dissolving during storage. Since the uncontrollable change of the speed of dissolving depends upon the rearrangement of modification II into modification I of the torasemide, it was obvious ab initio to use modification I from which, from our investigations, it followed that it is also stable in tablets and did not rearrange again back into modification II.
Therefore, the present invention provides oral forms of administration which contain torasemide of modification I as active material.
The process, which is sufficient for X-ray crystallography, of allowing both modifications to crystallise out together from the same solvent mixture and to separate them according to their macroscopic crystal form is, of course, useless for a large-scale preparation since such a separation of the crystals would not be feasible. Furthermore, it was known that torasemide, upon heating in most solvents, cyclises irreversibly with the anilino nitrogen atom. Therefore, a recrystallisation from most solvents is not suitable for the preparation of modification I. Consequently, there was the further problem of finding a process for the preparation of the pure modification I of torasemide which can be carried out simply and economically and without decomposition of the torasemide.
Surprisingly, we have now found that torasemide of modification II can be rearranged into modification I when a suspension thereof in water is seeded with very finely divided crystal nuclei of modification I and this suspension is stirred until the whole amount thereof has undergone rearrangement into modification I.
At ambient temperature, this rearrangement takes place relatively slowly so that a period of 10 to 14 days is necessary. However, the suspension can also be heated to temperatures of 70° to 90° C., in which case the reaction proceeds to completion within 3 to 6 hours. Whereas in the case of heating torasemide in solvents such as ethanol, ethyl acetate, methylene chloride and chloroform, decomposition products are formed in considerable amounts, torasemide can, surprisingly, be heated in water for several days to 90° C. without noticeable decomposition. Furthermore, it was surprising that even the addition of small amounts (up to 1%) bring about a rearrangement since torasemide of modification I has, in any case, a solubility of 1.9 g./liter at 90° C. Purely on the basis of the solubility, it was to have been expected that these small amounts of torasemide would dissolve in the aqueous suspension medium.
Since the rearrangement itself proceeds even in pure water, this process has the further advantage that no additional impurities, such as solvents, catalytically-acting acids or bases, etc. are entrained into the product. On the contrary, due to the recrystallisation procedure, impurities present in the original modification II pass into the water.
Oral forms of administration containing torasemide of modification I are produced in the usual way with the use of pharmacologically acceptable adjuvants, for example sugar, starch, starch derivatives, cellulose, cellulose derivatives, mould separation agents and anti-adhesion agents, as well as possibly flow regulation agents. In particular, in the case of the use of torasemide of modification I, aqueous process steps, for example granulation, can be carried out.
For the desired quality-determining parameter of the form of administration according to the present invention, it is especially advantageous when the active material torasemide of modification I is used with the following particle size distribution:
at least 90%≦96 μm. and,
at least 50%≦48 μm.
In comparison with pharmaceutical formulations with the active material torasemide of modification II, the formulations according to the present invention have a rapid in vitro rate of dissolving which remains unchanged even after comparatively long storage at temperatures higher than ambient temperature and at a comparatively high atmospheric humidity.
The rapidly commencing pharmacological action of these compositions is ensured by the rapid rate of dissolving of the active material from the form of administration. Thus, for example, after 15 minutes more than 60% has gone into solution and after 30 minutes more than 80%, the test method used being the paddle test USP XXI.
The following Examples are given for the purpose of illustrating the present invention:
10 kg. Torasemide, which has been prepared according to U.S. Pat. No. Re 30,633 and has been purified by reprecipitation from sodium bicarbonate solution with carbon dioxide, are suspended in the 10 fold amount of water and 100 g. of torasemide of modification I from a previous batch are added thereto. The suspension is heated to 90° C., stirred at this temperature for 6 hours, cooled to ambient temperature and again stirred for 30 minutes. Thereafter, the crystals are filtered off with suction, washed with 40 litres of water and dried in a vacuum drying cabinet at 50° C., 9.91 kg. of torasemide of modification I being obtained.
The X-ray diffraction diagram corresponds to that of the pure modification I and a testing for purity with HPLC corresponds to the pure starting material.
Crystal nuclei of modification I can possibly also be obtained according to the process described in Acta Cryst., 1978, p. 1304.
900 g. Torasemide of modification II are suspended in 10 litres of water and stirred at ambient temperature in the presence of 10 g. torasemide of modification I. After 8 days, a sample no longer contains any trace of modification II. The product is filtered off and dried in a vacuum drying cabinet at 50° C., 875 g. of torasemide of modification I thereby being obtained. The purity corresponds to that of the starting material and the X-ray crystallographic spectrum corresponds to that of the pure modification I.
For comparison, the same batch but without the addition of modification I was stirred at ambient temperature for 10 days without a rearrangement into modification I taking place.
10 kg. Crude torasemide, which has been prepared according to the procedure of U.S. Pat. No. Re 30,633, is suspended in 100 litres of water and mixed with 30 litres of 1N aqueous sodium hydroxide solution. After treatment with 500 g. of active charcoal and filtration, there is obtained a clear yellowish solution from which, by the addition of 1N sulphuric acid at ambient temperature up to the achievement of a pH value of 7.5, the torasemide is again precipitated out (consumption about 29 litres). 100 g. of torasemide of modification I are added to this suspension and the solution is heated from 6 hours to 90° C. During this time, the modification rearrangement takes place. The suspension is cooled to ambient temperature and the crystallisate is centrifuged off. The crystallisate is washed with 50 litres of water and finally dried at 50° C. in a vacuum drying cabinet, 9.82 g. of pure torasemide of modification I being obtained.
This Example shows that the rearrangement according to the present invention can also be carried out in the presence of foreign salts such as are present in the case of the normal precipitation of torasemide.
Torasemide of modification I is mixed in the usual way with lactose monohydrate and maize starch, granulated with water, dried and sieved (granulate 1). Highly dispersed silicon dioxide and magnesium stearate are mixed, sieved and admixed with granulate 1. This mixture is then tabletted in conventional manner. Production formulation for 100,000 tablets:
______________________________________
torasemide 0.25 kg.
lactose monohydrate 6.05 kg.
maize starch 1.60 kg.
silicon dioxide, highly dispersed
60.00 g.
magnesium stearate 40.00 g.
water, purified 1.20 kg.
______________________________________
Torasemide of modification I is mixed with lactose monohydrate, maize starch and a part of the magnesium stearate. The mixture is compacted and sieved to the desired gain size and grain size distribution (granulate 1). Highly dispersed silicon dioxide and magnesium stearate are mixed and sieved and admixed with granulate 1. The mixture is then tabletted in conventional manner.
Production formulation for 100,000 tablets:
______________________________________
torasemide 10.0 kg.
lactose monohydrate 2.0 kg.
maize starch 7.7 kg.
silicon dioxide, highly dispersed
0.2 kg.
magnesium stearate 0.1 kg.
______________________________________
It will be understood that the specification and examples are illustrative but not limitative of the present invention and that other embodiments within the spirit and scope of the invention will suggest themselves to those skilled in the art.
Claims (4)
1. A diuretic pharmaceutical composition comprising an effective amount of rapidly dissolving .Iadd.stable .Iaddend.crystalline torasemide of pure modification I (monoclinic, space group P21 /c, melting point .Badd..[.169° C..]..Baddend. .Iadd.of about 159° C. to about 161.5° C., in prism form.Iaddend.) substantially free of crystalline torasemide of modification II (monoclinic, space group P2/n, melting point .Badd..[.162° C..]..Baddend. .Iadd.of about 157.5° C. to about 160° C., in leaflet form.Iaddend.) and a pharmacologically acceptable carrier, said torasemide of modification I .Iadd.being storage stable in tablet form and .Iaddend.having solubility characteristics such that at least 60% is dissolved in water after 15 minutes, and at least 80% is dissolved in water after 30 minutes.
2. The composition of claim 1 comprising, by weight, approximately:
100 parts of the torasemide of modification I and, as the carrier,
20 parts lactose monohydrate,
77 parts maize starch,
2parts silicon dioxide and,
1 part magnesium stearate.
3. The composition of claim 1 comprising, by weight, approximately:
25parts of the torasemide of modification I and, as the carrier,
605 parts lactose monohydrate,
160 parts maize starch,
6 parts silicon dioxide and
4 parts magnesium stearate. .Iadd.
4. A method of producing a diuretic effect in a patient, said method comprising orally administering to the patient at least one storage-stable table consisting essentially of torasemide of pure modification I (monoclinic, space group P21 /c, melting point of about 159° to about 161.5° C., in prism form) and being substantially free of crystalline torasemide of modification II (monoclinic, space group P2/n, melting point of about 157.5° C. to about 160° C., in leaflet form). .Iaddend.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/043,631 USRE34672E (en) | 1985-08-17 | 1993-04-08 | Pharmaceutical composition containing a stable modification of torasemide |
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19853529529 DE3529529A1 (en) | 1985-08-17 | 1985-08-17 | METHOD FOR PRODUCING A STABLE MODIFICATION OF TORASEMIDE |
| DE3529529 | 1985-08-17 | ||
| US06/895,355 US4743693A (en) | 1985-08-17 | 1986-08-11 | Process for the preparation of a stable modification of torasemide |
| US07/111,439 US4822807A (en) | 1985-08-17 | 1987-10-20 | Pharmaceutical composition containing a stable modification of torasemide |
| US69134091A | 1991-04-18 | 1991-04-18 | |
| US08/043,631 USRE34672E (en) | 1985-08-17 | 1993-04-08 | Pharmaceutical composition containing a stable modification of torasemide |
Related Parent Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US07/111,439 Reissue US4822807A (en) | 1985-08-17 | 1987-10-20 | Pharmaceutical composition containing a stable modification of torasemide |
| US69134091A Continuation | 1985-08-17 | 1991-04-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| USRE34672E true USRE34672E (en) | 1994-07-26 |
Family
ID=6278766
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US06/895,355 Ceased US4743693A (en) | 1985-08-17 | 1986-08-11 | Process for the preparation of a stable modification of torasemide |
| US07/111,439 Ceased US4822807A (en) | 1985-08-17 | 1987-10-20 | Pharmaceutical composition containing a stable modification of torasemide |
| US07/985,053 Expired - Lifetime USRE34580E (en) | 1985-08-17 | 1992-12-03 | Process for the preparation of a stable modification of torasemide |
| US08/043,631 Expired - Lifetime USRE34672E (en) | 1985-08-17 | 1993-04-08 | Pharmaceutical composition containing a stable modification of torasemide |
Family Applications Before (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US06/895,355 Ceased US4743693A (en) | 1985-08-17 | 1986-08-11 | Process for the preparation of a stable modification of torasemide |
| US07/111,439 Ceased US4822807A (en) | 1985-08-17 | 1987-10-20 | Pharmaceutical composition containing a stable modification of torasemide |
| US07/985,053 Expired - Lifetime USRE34580E (en) | 1985-08-17 | 1992-12-03 | Process for the preparation of a stable modification of torasemide |
Country Status (25)
| Country | Link |
|---|---|
| US (4) | US4743693A (en) |
| EP (1) | EP0212537B1 (en) |
| JP (2) | JPS6245576A (en) |
| KR (1) | KR930009818B1 (en) |
| AU (1) | AU573454B2 (en) |
| CA (1) | CA1307277C (en) |
| CS (2) | CS259891B2 (en) |
| DD (1) | DD259858A5 (en) |
| DE (2) | DE3529529A1 (en) |
| DK (1) | DK162518C (en) |
| ES (1) | ES2001522A6 (en) |
| FI (1) | FI82189C (en) |
| GR (1) | GR862139B (en) |
| HK (1) | HK59994A (en) |
| HU (1) | HU195778B (en) |
| IE (1) | IE59237B1 (en) |
| IL (1) | IL79672A (en) |
| LT (1) | LT3596B (en) |
| NO (1) | NO170079C (en) |
| NZ (1) | NZ217172A (en) |
| PL (1) | PL146086B1 (en) |
| PT (1) | PT83186B (en) |
| SU (1) | SU1480766A3 (en) |
| UA (1) | UA7080A1 (en) |
| ZA (1) | ZA866151B (en) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US6166045A (en) | 1998-06-02 | 2000-12-26 | Roche Diagnostics Gmbh | Torasemide of modification III |
| US6399637B1 (en) * | 1998-02-10 | 2002-06-04 | Pliva, Farmaceutska, Kemijska, Prehrambena I Kozmeticka Industrija, Dionicko Drustvo | Crystal modification of torasemide |
| WO2002067935A1 (en) * | 2000-02-17 | 2002-09-06 | Teva Pharmaceutical Industries Ltd. | A stable pharmaceutical formulation comprising torsemide modification ii |
| US6465496B1 (en) | 1999-08-11 | 2002-10-15 | Teva Pharmaceutical Industries, Ltd. | Torsemide polymorphs |
| US20030022921A1 (en) * | 2001-02-21 | 2003-01-30 | Minutza Leibovici | Stable pharmaceutical formulation comprising torsemide modification II |
| US20030026835A1 (en) * | 1999-02-15 | 2003-02-06 | Sumitomo Pharmaceuticals Company Limited | Tablets disintegrating rapidly in the oral cavity |
| US6635765B2 (en) | 2000-03-20 | 2003-10-21 | Teva Pharmaceutical Industries, Ltd. | Processes for preparing torsemide intermediate |
| US20060100439A1 (en) * | 2002-07-19 | 2006-05-11 | Pliva Hrvatska D.O.O. | Process for the preparation of modification I of n-(1-methylethylaminocarbonyl)-4-(3-methylphenylamino)-3-pyridinesulfonamide |
| EP2266590A2 (en) | 2002-02-22 | 2010-12-29 | Shire LLC | Active agent delivery sytems and methods for protecting and administering active agents |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3623620A1 (en) * | 1986-07-12 | 1988-01-21 | Boehringer Mannheim Gmbh | MOLDABLE, AQUEOUS, ALKALINE INJECTION SOLUTIONS FROM TORASEMID AND METHOD FOR THE PRODUCTION THEREOF |
| US5166162A (en) * | 1990-03-02 | 1992-11-24 | Adir Et Compagnie | Pyridylsulfonylurea and pyridylsulfonylthiourea compounds |
| JP3586471B2 (en) * | 1991-06-25 | 2004-11-10 | 三菱ウェルファーマ株式会社 | Torasemide-containing pharmaceutical composition |
| 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 |
| IN192178B (en) * | 2001-08-03 | 2004-03-06 | Ranbaxy Lab | |
| ITMI20020639A1 (en) * | 2002-03-27 | 2003-09-29 | Cosma S P A | PHARMACEUTICAL COMPOSITIONS INCLUDING AS ACTIVE INGREDIENT 1-ISOPROPIL-3 ° (4-M-TOLUIDINO-3-PRIDIL) SULFONIL! -UREA |
| AU2003294405A1 (en) * | 2002-11-18 | 2004-06-15 | Teva Pharmaceutical Industries Ltd. | Stable lansoprazole containing more than 500 ppm, up to about 3,000 ppm water and more than 200 ppm, up to about 5,000 ppm alcohol |
| WO2004072061A1 (en) * | 2003-02-05 | 2004-08-26 | Teva Pharmaceutical Industries Ltd. | Method of stabilizing lansoprazole |
| ES2244324B1 (en) * | 2004-03-25 | 2006-11-16 | Ferrer Internacional, S.A. | DIURETIC COMPOSITIONS OF PROLONGED RELEASE. |
| AT500576B1 (en) * | 2004-07-28 | 2006-11-15 | Sanochemia Pharmazeutika Ag | PROCESS FOR REPRESENTING CRYSTAL FORMS OF TORSEMID |
| US10178893B1 (en) * | 2013-06-14 | 2019-01-15 | Scott Bradley Baker | Shoe |
| FR3018688A1 (en) * | 2014-03-19 | 2015-09-25 | Virbac | USE OF LOW-DOSE TORASEMIDE IN A VETERINARY COMPOSITION |
| 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 (en) * | 2015-11-27 | 2019-02-28 | Accupharma Spolka Z Ograniczona Odpowiedzialnoscia | Pharmaceutical combination preparation of ace inhibitor and loop diuretic |
| CN115417810B (en) * | 2022-09-22 | 2023-10-10 | 南京正科医药股份有限公司 | Refining method of torsemide crystal form I |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4018929A (en) * | 1974-04-17 | 1977-04-19 | A. Christiaens Societe Anonyme | 3-Loweralkylcarbamylsulfonamido-4-phenylaminopyridine-N-oxides, derivatives thereof and pharmaceutical compositions containing same |
| EP0003383A2 (en) * | 1978-01-31 | 1979-08-08 | A. Christiaens Societe Anonyme | 4-Amino-3-sulfonamido pyridine derivatives |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US30633A (en) * | 1860-11-13 | Improvement in fire-escapes | ||
| LU85193A1 (en) * | 1984-01-31 | 1985-09-12 | Christiaens Sa A | NOVEL 4-PHENYLAMINOPYRIDINE DERIVATIVES, THEIR USE AND THEIR PREPARATION |
-
1985
- 1985-08-17 DE DE19853529529 patent/DE3529529A1/en active Granted
-
1986
- 1986-08-10 IL IL79672A patent/IL79672A/en not_active IP Right Cessation
- 1986-08-11 CS CS865945A patent/CS259891B2/en not_active IP Right Cessation
- 1986-08-11 US US06/895,355 patent/US4743693A/en not_active Ceased
- 1986-08-11 CA CA000515676A patent/CA1307277C/en not_active Expired - Lifetime
- 1986-08-11 AU AU61055/86A patent/AU573454B2/en not_active Expired
- 1986-08-12 NZ NZ217172A patent/NZ217172A/en unknown
- 1986-08-12 PT PT83186A patent/PT83186B/en unknown
- 1986-08-12 EP EP86111118A patent/EP0212537B1/en not_active Expired - Lifetime
- 1986-08-12 DE DE8686111118T patent/DE3667970D1/en not_active Expired - Lifetime
- 1986-08-13 IE IE217986A patent/IE59237B1/en not_active IP Right Cessation
- 1986-08-13 DK DK385586A patent/DK162518C/en not_active IP Right Cessation
- 1986-08-14 KR KR1019860006689A patent/KR930009818B1/en not_active IP Right Cessation
- 1986-08-14 DD DD86293655A patent/DD259858A5/en not_active IP Right Cessation
- 1986-08-14 ES ES8601131A patent/ES2001522A6/en not_active Expired
- 1986-08-14 GR GR862139A patent/GR862139B/en unknown
- 1986-08-15 HU HU863598A patent/HU195778B/en unknown
- 1986-08-15 NO NO863305A patent/NO170079C/en not_active IP Right Cessation
- 1986-08-15 PL PL1986261052A patent/PL146086B1/en unknown
- 1986-08-15 UA UA4027953A patent/UA7080A1/en unknown
- 1986-08-15 ZA ZA866151A patent/ZA866151B/en unknown
- 1986-08-15 SU SU864027953A patent/SU1480766A3/en active
- 1986-08-15 FI FI863305A patent/FI82189C/en not_active IP Right Cessation
- 1986-08-18 JP JP61191789A patent/JPS6245576A/en active Granted
-
1987
- 1987-10-20 US US07/111,439 patent/US4822807A/en not_active Ceased
-
1989
- 1989-10-27 JP JP1278800A patent/JPH0643400B2/en not_active Expired - Lifetime
-
1991
- 1991-12-31 CS CS914199A patent/CS419991A3/en 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/en not_active IP Right Cessation
-
1994
- 1994-06-23 HK HK59994A patent/HK59994A/en not_active IP Right Cessation
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| US4018929A (en) * | 1974-04-17 | 1977-04-19 | A. Christiaens Societe Anonyme | 3-Loweralkylcarbamylsulfonamido-4-phenylaminopyridine-N-oxides, derivatives thereof and pharmaceutical compositions containing same |
| USRE30633E (en) * | 1974-04-17 | 1981-06-02 | A. Christiaens Societe Anonyme | 3-Lower alkylcarbamylsulfonamido-4-phenylaminopyridines, n-oxides, derivatives thereof and pharmaceutical compositions containing same |
| EP0003383A2 (en) * | 1978-01-31 | 1979-08-08 | A. Christiaens Societe Anonyme | 4-Amino-3-sulfonamido pyridine derivatives |
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| Dupont et al., Structure Cristalline et Mol culaire d n Divetigue . . . Acta Cryst. 13 34, 1304 1310, (1978). * |
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| US6399637B1 (en) * | 1998-02-10 | 2002-06-04 | Pliva, Farmaceutska, Kemijska, Prehrambena I Kozmeticka Industrija, Dionicko Drustvo | Crystal modification of torasemide |
| 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 |
| US20040229919A1 (en) * | 1998-10-02 | 2004-11-18 | Pliva Hrvatska D.O.O. | Crystal modification of torasemide |
| US20060205951A1 (en) * | 1998-10-02 | 2006-09-14 | Pliva Hrvatska D.O.O. | New crystal modification of torasemide |
| US6833379B2 (en) | 1998-10-02 | 2004-12-21 | Pliva Hrvatska D.O.O. | Crystal modification of torasemide |
| US20030026835A1 (en) * | 1999-02-15 | 2003-02-06 | Sumitomo Pharmaceuticals Company Limited | Tablets disintegrating rapidly in the oral cavity |
| US6465496B1 (en) | 1999-08-11 | 2002-10-15 | Teva Pharmaceutical Industries, Ltd. | Torsemide polymorphs |
| WO2002067935A1 (en) * | 2000-02-17 | 2002-09-06 | Teva Pharmaceutical Industries Ltd. | A stable pharmaceutical formulation comprising torsemide modification ii |
| US6482417B2 (en) | 2000-02-17 | 2002-11-19 | Teva Pharmaceutical Industries Ltd. | Stable pharmaceutical formulation comprising torsemide modification II |
| US6635765B2 (en) | 2000-03-20 | 2003-10-21 | Teva Pharmaceutical Industries, Ltd. | Processes for preparing torsemide intermediate |
| US6670478B2 (en) | 2000-03-20 | 2003-12-30 | Teva Pharmaceutical Industries, Ltd. | Process for preparing torsemide intermediate |
| US20030022921A1 (en) * | 2001-02-21 | 2003-01-30 | Minutza Leibovici | Stable pharmaceutical formulation comprising torsemide modification II |
| EP2266590A2 (en) | 2002-02-22 | 2010-12-29 | Shire LLC | Active agent delivery sytems and methods for protecting and administering active agents |
| EP2316468A1 (en) | 2002-02-22 | 2011-05-04 | Shire LLC | Delivery system and methods for protecting and administering dextroamphetamine |
| EP2316469A1 (en) | 2002-02-22 | 2011-05-04 | Shire LLC | Delivery system and methods for protecting and administering dextroamphetamine |
| US20060100439A1 (en) * | 2002-07-19 | 2006-05-11 | Pliva Hrvatska D.O.O. | Process for the preparation of modification I of n-(1-methylethylaminocarbonyl)-4-(3-methylphenylamino)-3-pyridinesulfonamide |
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