HRP20020819A2 - Novel processes for preparing torsemide intermediate - Google Patents
Novel processes for preparing torsemide intermediate Download PDFInfo
- Publication number
- HRP20020819A2 HRP20020819A2 HRP20020819A HRP20020819A2 HR P20020819 A2 HRP20020819 A2 HR P20020819A2 HR P20020819 A HRP20020819 A HR P20020819A HR P20020819 A2 HRP20020819 A2 HR P20020819A2
- Authority
- HR
- Croatia
- Prior art keywords
- ammonia
- pyridine
- chloro
- added
- sulfonamide
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 52
- 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 25
- 229960005461 torasemide Drugs 0.000 title claims description 24
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 79
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 51
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 48
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 40
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 39
- 229910021529 ammonia Inorganic materials 0.000 claims description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 21
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 17
- 239000003960 organic solvent Substances 0.000 claims description 17
- 239000000243 solution Substances 0.000 claims description 16
- 238000002360 preparation method Methods 0.000 claims description 15
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical group COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 13
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- 239000007864 aqueous solution Substances 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 7
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 7
- GSLTVFIVJMCNBH-UHFFFAOYSA-N 2-isocyanatopropane Chemical compound CC(C)N=C=O GSLTVFIVJMCNBH-UHFFFAOYSA-N 0.000 claims description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 6
- 239000008096 xylene Substances 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 3
- 238000002955 isolation Methods 0.000 claims description 2
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 229940086542 triethylamine Drugs 0.000 claims 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 14
- 239000000908 ammonium hydroxide Substances 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 8
- 150000003927 aminopyridines Chemical class 0.000 description 7
- 239000000543 intermediate Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 238000012769 bulk production Methods 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 206010030113 Oedema Diseases 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- -1 25 V Substances 0.000 description 1
- FDWIUWCUNDLRSE-UHFFFAOYSA-N 3-(3-methylphenyl)pyridin-2-amine Chemical compound CC1=CC=CC(C=2C(=NC=CC=2)N)=C1 FDWIUWCUNDLRSE-UHFFFAOYSA-N 0.000 description 1
- AZRCSTMIVMQIPR-UHFFFAOYSA-N 4-oxo-1h-pyridine-3-sulfonic acid Chemical compound OC1=CC=[NH+]C=C1S([O-])(=O)=O AZRCSTMIVMQIPR-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 206010007559 Cardiac failure congestive Diseases 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 208000020832 chronic kidney disease Diseases 0.000 description 1
- 208000022831 chronic renal failure syndrome Diseases 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 208000017169 kidney disease Diseases 0.000 description 1
- 208000019423 liver disease Diseases 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- OMQYPTWMALFUKY-UHFFFAOYSA-N n-(3-methylphenyl)pyridin-2-amine Chemical compound CC1=CC=CC(NC=2N=CC=CC=2)=C1 OMQYPTWMALFUKY-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
- C07D213/71—Sulfur atoms to which a second hetero atom is attached
-
- 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
- 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- 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
- C07D213/61—Halogen atoms or nitro radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Cardiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Hematology (AREA)
- Hospice & Palliative Care (AREA)
- Diabetes (AREA)
- Epidemiology (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US19065000P | 2000-03-20 | 2000-03-20 | |
US21151000P | 2000-06-14 | 2000-06-14 | |
PCT/US2001/008866 WO2001070226A1 (en) | 2000-03-20 | 2001-03-20 | Novel processes for preparing torsemide intermediate |
Publications (1)
Publication Number | Publication Date |
---|---|
HRP20020819A2 true HRP20020819A2 (en) | 2004-12-31 |
Family
ID=26886305
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HRP20020819 HRP20020819A2 (en) | 2000-03-20 | 2002-10-14 | Novel processes for preparing torsemide intermediate |
Country Status (15)
Country | Link |
---|---|
US (2) | US6635765B2 (cs) |
EP (1) | EP1284733A4 (cs) |
JP (1) | JP2003527425A (cs) |
KR (1) | KR20020081482A (cs) |
CN (2) | CN1203059C (cs) |
AU (2) | AU4759201A (cs) |
CA (1) | CA2403382A1 (cs) |
CZ (1) | CZ20023395A3 (cs) |
HR (1) | HRP20020819A2 (cs) |
HU (1) | HUP0300241A3 (cs) |
IL (1) | IL151837A0 (cs) |
NZ (1) | NZ521852A (cs) |
PL (1) | PL370039A1 (cs) |
SK (1) | SK14802002A3 (cs) |
WO (1) | WO2001070226A1 (cs) |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20020025217A (ko) * | 1999-08-11 | 2002-04-03 | 추후보정 | 토르세미드 동질이상 |
IL149771A0 (en) * | 2002-05-21 | 2002-11-10 | Fintech Lab Ltd | Process for preparation of torsemide |
ITMI20022749A1 (it) * | 2002-12-23 | 2004-06-24 | Cosma S P A | Nuovo procedimento per la sintesi della tosemide, in particolare della forma ii pura e stabile. |
US7378527B2 (en) * | 2004-03-16 | 2008-05-27 | Daqing Che | Process for the preparation of torsemide and related intermediates |
DE102009005095A1 (de) * | 2009-01-19 | 2010-07-22 | MAX-PLANCK-Gesellschaft zur Förderung der Wissenschaften e.V. | Verfahren zur Herstellung von Carbonitriden über Polykondensations- bzw. Sol-Gel-Verfahren unter Verwendung Wasserstoff-freier Isocyanate |
CN102432532B (zh) * | 2011-11-10 | 2014-06-18 | 天津市汉康医药生物技术有限公司 | 高纯度托拉塞米化合物 |
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 |
JP6817952B2 (ja) * | 2015-10-29 | 2021-01-20 | あすか製薬株式会社 | ピリミジン誘導体 |
CN110054647B (zh) * | 2019-05-23 | 2021-06-15 | 上海勋和医药科技有限公司 | 托拉塞米磷酸酯类前药、其制备方法及组合物 |
GB202102575D0 (en) | 2021-02-23 | 2021-04-07 | Teva Pharmaceutical Industries Ltd | Fixed-dose pharmaceutical compositions |
CN115010659A (zh) * | 2022-06-22 | 2022-09-06 | 南京正科医药股份有限公司 | 一种托拉塞米新杂质对照品及其制备方法 |
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 (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2516025A (en) | 1947-03-27 | 1950-07-18 | Westinghouse Electric Corp | Ground-relay transmission-line protection |
BE758749A (fr) | 1969-11-12 | 1971-05-10 | Ciba Geigy | Procede de preparation de nouveaux acides pyridine-sulfoniques |
US3787573A (en) * | 1970-03-18 | 1974-01-22 | R Mizzoni | Pyridine sulfonic acids as diuretics |
US3674794A (en) * | 1970-03-18 | 1972-07-04 | Ciba Geigy Corp | Certain-3-pyridine-sulfonamide derivatives |
US3824241A (en) * | 1970-08-26 | 1974-07-16 | Ciba Geigy Corp | Pyridinesulfonic acids |
GB1368948A (en) | 1970-11-11 | 1974-10-02 | Manuf Prod Pharma | Pyridine derivatives |
US3904636A (en) | 1971-11-09 | 1975-09-09 | Christiaens Sa A | 3-sulfonamido-4-phenyl aminopyridines and derivatives |
ES436109A1 (es) * | 1974-04-04 | 1977-01-01 | Christiaens Sa A | Procedimiento para la preparacion de nuevos derivados de pi-ridina. |
US4055650A (en) | 1974-04-17 | 1977-10-25 | A. Christiaens Societe Anonyme | Certain 4-phenoxy(or phenylthio)-3-n-acylated-sulfonamido-pyridines |
GB1477664A (en) * | 1974-04-17 | 1977-06-22 | Christiaens Sa A | Pyridine derivatives |
US4042693A (en) | 1975-04-14 | 1977-08-16 | A. Christiaens Societe Anonyme | Derivatives of 1,2,4-thiadiazine |
GB1593609A (en) | 1978-01-31 | 1981-07-22 | Christiaens Sa A | Pyridine sulfonamides |
DE3529529A1 (de) | 1985-08-17 | 1987-02-19 | Boehringer Mannheim Gmbh | Verfahren zur herstellung einer stabilen modifikation von torasemid |
DE3623620A1 (de) | 1986-07-12 | 1988-01-21 | Boehringer Mannheim Gmbh | Spritzfertige, waessrige, alkalische injektionsloesungen von torasemid und verfahren zu ihrer herstellung |
FR2703051B1 (fr) | 1993-03-26 | 1995-04-28 | Adir | Nouvelles pyridothiadiazines, leurs procédés de préparation, et les compositions pharmaceutiques qui les contiennent. |
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 |
-
2001
- 2001-03-20 PL PL01370039A patent/PL370039A1/xx not_active Application Discontinuation
- 2001-03-20 US US09/812,762 patent/US6635765B2/en not_active Expired - Fee Related
- 2001-03-20 AU AU4759201A patent/AU4759201A/xx active Pending
- 2001-03-20 CA CA002403382A patent/CA2403382A1/en not_active Abandoned
- 2001-03-20 CN CNB018068340A patent/CN1203059C/zh not_active Expired - Fee Related
- 2001-03-20 EP EP01920556A patent/EP1284733A4/en not_active Withdrawn
- 2001-03-20 CN CNA2004100787386A patent/CN1623987A/zh active Pending
- 2001-03-20 IL IL15183701A patent/IL151837A0/xx unknown
- 2001-03-20 NZ NZ521852A patent/NZ521852A/en unknown
- 2001-03-20 WO PCT/US2001/008866 patent/WO2001070226A1/en active IP Right Grant
- 2001-03-20 CZ CZ20023395A patent/CZ20023395A3/cs unknown
- 2001-03-20 JP JP2001568424A patent/JP2003527425A/ja not_active Withdrawn
- 2001-03-20 SK SK1480-2002A patent/SK14802002A3/sk unknown
- 2001-03-20 HU HU0300241A patent/HUP0300241A3/hu unknown
- 2001-03-20 AU AU2001247592A patent/AU2001247592B2/en not_active Ceased
- 2001-03-20 KR KR1020027012490A patent/KR20020081482A/ko not_active Application Discontinuation
-
2002
- 2002-10-14 HR HRP20020819 patent/HRP20020819A2/hr not_active Application Discontinuation
-
2003
- 2003-05-02 US US10/428,463 patent/US6670478B2/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
AU2001247592B2 (en) | 2005-08-18 |
EP1284733A1 (en) | 2003-02-26 |
US20020019537A1 (en) | 2002-02-14 |
HUP0300241A2 (hu) | 2003-06-28 |
US20030212277A1 (en) | 2003-11-13 |
IL151837A0 (en) | 2003-04-10 |
CZ20023395A3 (cs) | 2003-04-16 |
WO2001070226A1 (en) | 2001-09-27 |
JP2003527425A (ja) | 2003-09-16 |
CA2403382A1 (en) | 2001-09-27 |
CN1423558A (zh) | 2003-06-11 |
KR20020081482A (ko) | 2002-10-26 |
NZ521852A (en) | 2004-10-29 |
PL370039A1 (en) | 2005-05-16 |
AU4759201A (en) | 2001-10-03 |
US6635765B2 (en) | 2003-10-21 |
HUP0300241A3 (en) | 2005-11-28 |
CN1623987A (zh) | 2005-06-08 |
EP1284733A4 (en) | 2003-07-16 |
US6670478B2 (en) | 2003-12-30 |
SK14802002A3 (sk) | 2003-05-02 |
CN1203059C (zh) | 2005-05-25 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
HRP20020819A2 (en) | Novel processes for preparing torsemide intermediate | |
CA2220094C (en) | Process for producing guanidine derivatives, intermediates therefor and their production | |
AU2001247592A1 (en) | Novel processes for preparing torsemide intermediate | |
HRP20010747A2 (en) | Novel synthesis and crystallization of piperazine ring-containing compounds | |
US6545149B2 (en) | Synthesis and crystallization of piperazine ring-containing compounds | |
US7378527B2 (en) | Process for the preparation of torsemide and related intermediates | |
EP1741429A2 (en) | Processes for preparing torsemide | |
DK171253B1 (da) | Fremgangsmåde til fremstilling af 5-Q-[3,4-bipyri din]-6(1H)-on | |
AU2005203389A1 (en) | Novel processes for preparing torsemide intermediate | |
JPS5822107B2 (ja) | α↓−アミノメチレン↓−β↓−ホルミルアミノプロピオニトリル及びその製法 | |
CN108341771B (zh) | 一种3-氰基-2,6-二羟基吡啶钠水合物的制备方法 | |
JP3292933B2 (ja) | 2−アミノ−3−ニトロピリジン類の製造方法 | |
US20030135043A1 (en) | Novel synthesis and crystallization of piperazine ring-containing compounds | |
WO2014126954A1 (en) | Regioselective synthesis of substituted pyrimidines | |
WO2022206742A1 (zh) | 一种一步法合成乙内酰硫脲衍生物的方法 | |
CA2183869A1 (en) | Method of preparing 6-aryloxymethyl-1-hydroxy-4-methyl-2-pyridones | |
JPS62267267A (ja) | ピラゾ−ル誘導体およびその製造法 | |
JPH06199809A (ja) | 2,5−ジブロモピリミジンの製造法 | |
ZA200506290B (en) | MEthod for the production of telmisartan | |
SI8712448A8 (en) | Process for preparing 1-ethyl-6-flouro-4-oxo-7-(4-methyl-1-piperazinyl)-1,4-dihydroquiniline -3-carboxylic acids | |
JPH06172319A (ja) | 2−アルキル−4−ハロゲノ−5−ホルミルイミダゾールの精製方法 | |
JPS6144874A (ja) | 2,4−ジアミノ−5−ホルミルピリミジンの製法 | |
CA2460432A1 (en) | Process for the preparation of torsemide and related intermediates |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A1OB | Publication of a patent application | ||
AIPI | Request for the grant of a patent on the basis of a substantive examination of a patent application | ||
ODRP | Renewal fee for the maintenance of a patent |
Payment date: 20060227 Year of fee payment: 6 |
|
OBST | Application withdrawn |