ZA200208309B - Amorphous torasemide modification. - Google Patents
Amorphous torasemide modification. Download PDFInfo
- Publication number
- ZA200208309B ZA200208309B ZA200208309A ZA200208309A ZA200208309B ZA 200208309 B ZA200208309 B ZA 200208309B ZA 200208309 A ZA200208309 A ZA 200208309A ZA 200208309 A ZA200208309 A ZA 200208309A ZA 200208309 B ZA200208309 B ZA 200208309B
- Authority
- ZA
- South Africa
- Prior art keywords
- amorphous
- torasemide
- modification
- torasemide modification
- preparation
- Prior art date
Links
- 230000004048 modification Effects 0.000 title claims description 98
- 238000012986 modification Methods 0.000 title claims description 98
- 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 description 97
- 229960005461 torasemide Drugs 0.000 title claims description 94
- 239000000243 solution Substances 0.000 claims description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 37
- 238000000034 method Methods 0.000 claims description 32
- 230000008569 process Effects 0.000 claims description 29
- 238000002360 preparation method Methods 0.000 claims description 22
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 20
- 239000013078 crystal Substances 0.000 claims description 20
- 238000004108 freeze drying Methods 0.000 claims description 19
- 239000000843 powder Substances 0.000 claims description 11
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 8
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 8
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- 208000028867 ischemia Diseases 0.000 claims description 8
- 206010006451 bronchitis Diseases 0.000 claims description 7
- 239000002934 diuretic Substances 0.000 claims description 7
- 230000001882 diuretic effect Effects 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 206010002383 Angina Pectoris Diseases 0.000 claims description 4
- 208000012904 Bartter disease Diseases 0.000 claims description 4
- 208000010062 Bartter syndrome Diseases 0.000 claims description 4
- 206010048962 Brain oedema Diseases 0.000 claims description 4
- 206010010254 Concussion Diseases 0.000 claims description 4
- 208000016998 Conn syndrome Diseases 0.000 claims description 4
- 208000010412 Glaucoma Diseases 0.000 claims description 4
- 206010020772 Hypertension Diseases 0.000 claims description 4
- 206010027476 Metastases Diseases 0.000 claims description 4
- 206010028980 Neoplasm Diseases 0.000 claims description 4
- 206010037423 Pulmonary oedema Diseases 0.000 claims description 4
- 206010039808 Secondary aldosteronism Diseases 0.000 claims description 4
- 208000007536 Thrombosis Diseases 0.000 claims description 4
- 230000005856 abnormality Effects 0.000 claims description 4
- 230000001154 acute effect Effects 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 4
- 239000013566 allergen Substances 0.000 claims description 4
- 208000006673 asthma Diseases 0.000 claims description 4
- 210000004556 brain Anatomy 0.000 claims description 4
- 208000006752 brain edema Diseases 0.000 claims description 4
- 229920002678 cellulose Polymers 0.000 claims description 4
- 239000001913 cellulose Substances 0.000 claims description 4
- 235000010980 cellulose Nutrition 0.000 claims description 4
- 230000009514 concussion Effects 0.000 claims description 4
- 230000003247 decreasing effect Effects 0.000 claims description 4
- 230000001037 epileptic effect Effects 0.000 claims description 4
- 210000005003 heart tissue Anatomy 0.000 claims description 4
- 208000015181 infectious disease Diseases 0.000 claims description 4
- 208000014674 injury Diseases 0.000 claims description 4
- 230000002503 metabolic effect Effects 0.000 claims description 4
- 208000013846 primary aldosteronism Diseases 0.000 claims description 4
- 208000005333 pulmonary edema Diseases 0.000 claims description 4
- 230000000451 tissue damage Effects 0.000 claims description 4
- 231100000827 tissue damage Toxicity 0.000 claims description 4
- 230000008733 trauma Effects 0.000 claims description 4
- 206010006458 Bronchitis chronic Diseases 0.000 claims description 3
- 238000010521 absorption reaction Methods 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 208000007451 chronic bronchitis Diseases 0.000 claims description 3
- 230000004410 intraocular pressure Effects 0.000 claims description 3
- 229920000881 Modified starch Polymers 0.000 claims description 2
- 229920002472 Starch Polymers 0.000 claims description 2
- 230000000181 anti-adherent effect Effects 0.000 claims description 2
- 239000002775 capsule Substances 0.000 claims description 2
- 238000002347 injection Methods 0.000 claims description 2
- 239000007924 injection Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 235000019426 modified starch Nutrition 0.000 claims description 2
- 239000002994 raw material Substances 0.000 claims description 2
- 235000019698 starch Nutrition 0.000 claims description 2
- 239000008107 starch Substances 0.000 claims description 2
- 235000000346 sugar Nutrition 0.000 claims description 2
- 230000000996 additive effect Effects 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- 238000002844 melting Methods 0.000 description 23
- 230000008018 melting Effects 0.000 description 23
- 238000002329 infrared spectrum Methods 0.000 description 21
- 238000000354 decomposition reaction Methods 0.000 description 11
- 238000002955 isolation Methods 0.000 description 9
- 238000004090 dissolution Methods 0.000 description 8
- 229910021529 ammonia Inorganic materials 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- 238000000113 differential scanning calorimetry Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 230000009471 action Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000004566 IR spectroscopy Methods 0.000 description 2
- 238000002441 X-ray diffraction Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 229910016523 CuKa Inorganic materials 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 241000257303 Hymenoptera Species 0.000 description 1
- UJEWTUDSLQGTOA-UHFFFAOYSA-N Piretanide Chemical compound C=1C=CC=CC=1OC=1C(S(=O)(=O)N)=CC(C(O)=O)=CC=1N1CCCC1 UJEWTUDSLQGTOA-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- YAXMCEWRTZAGIM-DSTWUDMISA-N [(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-26-[(E)-(4-cyclopentylpiperazin-1-yl)iminomethyl]-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1(29),2,4,9,19,21,25,27-octaen-13-yl] acetate hydrochloride Chemical compound Cl.CO[C@H]1\C=C\O[C@@]2(C)Oc3c(C2=O)c2c(O)c(\C=N\N4CCN(CC4)C4CCCC4)c(NC(=O)\C(C)=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@@H]1C)c(O)c2c(O)c3C YAXMCEWRTZAGIM-DSTWUDMISA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- 230000003178 anti-diabetic effect Effects 0.000 description 1
- 239000003472 antidiabetic agent Substances 0.000 description 1
- IIOPLILENRZKRV-UHFFFAOYSA-N azosemide Chemical compound C=1C=CSC=1CNC=1C=C(Cl)C(S(=O)(=O)N)=CC=1C1=NN=N[N]1 IIOPLILENRZKRV-UHFFFAOYSA-N 0.000 description 1
- 229960004988 azosemide Drugs 0.000 description 1
- 229940125717 barbiturate Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 229960004064 bumetanide Drugs 0.000 description 1
- MAEIEVLCKWDQJH-UHFFFAOYSA-N bumetanide Chemical compound CCCCNC1=CC(C(O)=O)=CC(S(N)(=O)=O)=C1OC1=CC=CC=C1 MAEIEVLCKWDQJH-UHFFFAOYSA-N 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000012822 chemical development Methods 0.000 description 1
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 1
- 229940030606 diuretics Drugs 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 229960003883 furosemide Drugs 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000009878 intermolecular interaction Effects 0.000 description 1
- 230000008863 intramolecular interaction Effects 0.000 description 1
- 239000002171 loop diuretic Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229960001085 piretanide Drugs 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000013341 scale-up Methods 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000001757 thermogravimetry curve Methods 0.000 description 1
- GXPHKUHSUJUWKP-UHFFFAOYSA-N troglitazone Chemical compound C1CC=2C(C)=C(O)C(C)=C(C)C=2OC1(C)COC(C=C1)=CC=C1CC1SC(=O)NC1=O GXPHKUHSUJUWKP-UHFFFAOYSA-N 0.000 description 1
- 229960001641 troglitazone Drugs 0.000 description 1
- GXPHKUHSUJUWKP-NTKDMRAZSA-N troglitazone Natural products C([C@@]1(OC=2C(C)=C(C(=C(C)C=2CC1)O)C)C)OC(C=C1)=CC=C1C[C@H]1SC(=O)NC1=O GXPHKUHSUJUWKP-NTKDMRAZSA-N 0.000 description 1
- 238000002211 ultraviolet spectrum 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
-
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
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- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/38—Drugs for disorders of the endocrine system of the suprarenal hormones
- A61P5/42—Drugs for disorders of the endocrine system of the suprarenal hormones for decreasing, blocking or antagonising the activity of mineralocorticosteroids
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
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- A—HUMAN NECESSITIES
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- A61P7/10—Antioedematous agents; Diuretics
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- A—HUMAN NECESSITIES
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- 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
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
- C07D213/71—Sulfur atoms to which a second hetero atom is attached
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Diabetes (AREA)
- Ophthalmology & Optometry (AREA)
- Hematology (AREA)
- Urology & Nephrology (AREA)
- Biomedical Technology (AREA)
- Oncology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Vascular Medicine (AREA)
- Communicable Diseases (AREA)
- Endocrinology (AREA)
- Pain & Pain Management (AREA)
- Obesity (AREA)
- Otolaryngology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pyridine Compounds (AREA)
- Materials For Medical Uses (AREA)
- Enzymes And Modification Thereof (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
HR20000162A HRP20000162B1 (en) | 2000-03-20 | 2000-03-20 | Amorphous torasemide modification |
Publications (1)
Publication Number | Publication Date |
---|---|
ZA200208309B true ZA200208309B (en) | 2003-10-15 |
Family
ID=10947070
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ZA200208309A ZA200208309B (en) | 2000-03-20 | 2002-10-15 | Amorphous torasemide modification. |
Country Status (29)
Country | Link |
---|---|
US (1) | US6767917B1 (fr) |
EP (1) | EP1272470B1 (fr) |
JP (1) | JP2003528083A (fr) |
KR (1) | KR20020093847A (fr) |
CN (1) | CN1211368C (fr) |
AR (1) | AR023788A1 (fr) |
AT (1) | ATE256662T1 (fr) |
AU (1) | AU2000241348A1 (fr) |
BG (1) | BG107208A (fr) |
BR (1) | BR0017175A (fr) |
CA (1) | CA2401908A1 (fr) |
CZ (1) | CZ20023436A3 (fr) |
DE (1) | DE60007360T2 (fr) |
EA (1) | EA004950B1 (fr) |
EE (1) | EE200200534A (fr) |
ES (1) | ES2213006T3 (fr) |
GE (1) | GEP20043300B (fr) |
HR (1) | HRP20000162B1 (fr) |
HU (1) | HUP0300596A3 (fr) |
IL (1) | IL151801A0 (fr) |
IS (1) | IS6551A (fr) |
MX (1) | MXPA02009210A (fr) |
NO (1) | NO20024464L (fr) |
PL (1) | PL357154A1 (fr) |
PT (1) | PT1272470E (fr) |
SK (1) | SK15092002A3 (fr) |
WO (1) | WO2001070694A1 (fr) |
YU (1) | YU70502A (fr) |
ZA (1) | ZA200208309B (fr) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6465496B1 (en) * | 1999-08-11 | 2002-10-15 | Teva Pharmaceutical Industries, Ltd. | Torsemide polymorphs |
IN192178B (fr) | 2001-08-03 | 2004-03-06 | Ranbaxy Lab | |
US7282519B2 (en) | 2003-08-28 | 2007-10-16 | Nitromed, Inc. | Nitrosated and nitrosylated diuretic compounds, compositions and methods of use |
WO2006091716A2 (fr) | 2005-02-24 | 2006-08-31 | Nitromed, Inc. | Compositions et composes diuretiques renforçateurs d'oxyde nitrique, et leurs procedes d'utilisation |
CN100421662C (zh) * | 2005-11-08 | 2008-10-01 | 周卓和 | 托拉塞米分散片及其制备方法和应用 |
CN104370805B (zh) * | 2013-08-13 | 2016-09-07 | 天津汉瑞药业有限公司 | 托拉塞米化合物 |
CN105949115A (zh) * | 2016-05-26 | 2016-09-21 | 南京正科医药股份有限公司 | 一种新晶型托拉塞米 |
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 (8)
Publication number | Priority date | Publication date | Assignee | Title |
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GB1477664A (en) | 1974-04-17 | 1977-06-22 | Christiaens Sa A | Pyridine derivatives |
DE3529529A1 (de) * | 1985-08-17 | 1987-02-19 | Boehringer Mannheim Gmbh | Verfahren zur herstellung einer stabilen modifikation von torasemid |
GB8816620D0 (en) | 1988-07-13 | 1988-08-17 | Lepetit Spa | Rifapentine hydrohalides |
DK0812320T3 (da) | 1995-02-22 | 2003-04-14 | Aventis Pharma Ltd | Amorft piretanid, polymorfe former deraf, fremgangsmåde til fremstilling deraf og deres anvendelse |
IN182496B (fr) | 1996-02-20 | 1999-04-17 | Reddy Research Foundation | |
HRP980532B1 (en) * | 1998-10-02 | 2005-06-30 | Pliva | Novel crystalline torasemide modification |
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 |
US6465496B1 (en) | 1999-08-11 | 2002-10-15 | Teva Pharmaceutical Industries, Ltd. | Torsemide polymorphs |
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