CA2367903A1 - Nouveau procede de fabrication de mesylate de doxazosine lors d'une modification cristalline designee par la forme a - Google Patents
Nouveau procede de fabrication de mesylate de doxazosine lors d'une modification cristalline designee par la forme a Download PDFInfo
- Publication number
- CA2367903A1 CA2367903A1 CA002367903A CA2367903A CA2367903A1 CA 2367903 A1 CA2367903 A1 CA 2367903A1 CA 002367903 A CA002367903 A CA 002367903A CA 2367903 A CA2367903 A CA 2367903A CA 2367903 A1 CA2367903 A1 CA 2367903A1
- Authority
- CA
- Canada
- Prior art keywords
- doxazosin
- doxazosin mesylate
- mesylate
- methanol
- organic solvent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 229960000220 doxazosin mesylate Drugs 0.000 title claims abstract description 41
- VJECBOKJABCYMF-UHFFFAOYSA-N doxazosin mesylate Chemical compound [H+].CS([O-])(=O)=O.C1OC2=CC=CC=C2OC1C(=O)N(CC1)CCN1C1=NC(N)=C(C=C(C(OC)=C2)OC)C2=N1 VJECBOKJABCYMF-UHFFFAOYSA-N 0.000 title claims abstract description 41
- 230000004048 modification Effects 0.000 title claims abstract description 21
- 238000012986 modification Methods 0.000 title claims abstract description 21
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 57
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims abstract description 35
- RUZYUOTYCVRMRZ-UHFFFAOYSA-N doxazosin Chemical compound C1OC2=CC=CC=C2OC1C(=O)N(CC1)CCN1C1=NC(N)=C(C=C(C(OC)=C2)OC)C2=N1 RUZYUOTYCVRMRZ-UHFFFAOYSA-N 0.000 claims abstract description 25
- 229960001389 doxazosin Drugs 0.000 claims abstract description 24
- 239000013078 crystal Substances 0.000 claims abstract description 13
- 239000000203 mixture Substances 0.000 claims abstract description 11
- 239000003495 polar organic solvent Substances 0.000 claims abstract description 8
- 239000003960 organic solvent Substances 0.000 claims abstract description 5
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 17
- 238000001914 filtration Methods 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 7
- 238000001816 cooling Methods 0.000 claims description 6
- 238000010899 nucleation Methods 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 238000003756 stirring Methods 0.000 description 9
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 8
- 238000010992 reflux Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 238000005169 Debye-Scherrer Methods 0.000 description 1
- 125000005233 alkylalcohol group Chemical group 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- -1 methanol or ethanol Chemical compound 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000001757 thermogravimetry curve Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/517—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Epidemiology (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
Nouveau procédé de fabrication de mésylate de doxazosine selon la modification A, qui consiste à dissoudre de la doxazosine avec de l'acide méthane-sulfonique dans un mélange constitué d'un solvant organique polaire aprotique et de méthanol, éventuellement à supprimer la turbidité de la solution ainsi obtenue, à inoculer la solution claire éventuellement avec des cristaux de mésylate de doxazosine de forme A, à chauffer ladite solution, à isoler le produit formé, après refroidissement, puis à laver ledit produit avec un solvant organique et à le sécher.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19912063.3 | 1999-03-18 | ||
| DE19912063A DE19912063A1 (de) | 1999-03-18 | 1999-03-18 | Neues Verfahren zur Herstellung von Doxazosin-Mesylat in einer als Form A bezeichneten Kristallmodifikation |
| PCT/EP2000/001939 WO2000056731A1 (fr) | 1999-03-18 | 2000-03-06 | Nouveau procede de fabrication de mesylate de doxazosine lors d'une modification cristalline designee par la forme a |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2367903A1 true CA2367903A1 (fr) | 2000-09-28 |
Family
ID=7901411
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002367903A Abandoned CA2367903A1 (fr) | 1999-03-18 | 2000-03-06 | Nouveau procede de fabrication de mesylate de doxazosine lors d'une modification cristalline designee par la forme a |
Country Status (13)
| Country | Link |
|---|---|
| EP (1) | EP1165548A1 (fr) |
| JP (1) | JP2002540109A (fr) |
| KR (1) | KR20010113753A (fr) |
| CN (1) | CN1352643A (fr) |
| AU (1) | AU3960800A (fr) |
| CA (1) | CA2367903A1 (fr) |
| CZ (1) | CZ20013347A3 (fr) |
| DE (1) | DE19912063A1 (fr) |
| HU (1) | HUP0200663A2 (fr) |
| IL (1) | IL144944A0 (fr) |
| PL (1) | PL350088A1 (fr) |
| TR (1) | TR200102730T2 (fr) |
| WO (1) | WO2000056731A1 (fr) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19912573A1 (de) * | 1999-03-19 | 2000-09-21 | Knoll Ag | Arzneimittel, enthaltend Doxazosin-Mesylat der Kristallmodifikaton D |
| RU2186779C1 (ru) * | 2001-01-31 | 2002-08-10 | Федеральное государственное унитарное предприятие Государственный научный центр "Научно-исследовательский институт органических полупродуктов и красителей" | Способ получения метансульфоната доксазозина |
| AU2008339652B2 (en) * | 2007-12-24 | 2013-07-04 | Cipla Limited | Crystalline polymorph of doxazosin mesylate (form IV) and process for preparation thereof |
| CN109988158A (zh) * | 2018-01-03 | 2019-07-09 | 合肥立方制药股份有限公司 | X晶型、含有x晶型的多沙唑嗪甲磺酸盐及其制备方法和用途 |
| CN111303130B (zh) * | 2018-12-11 | 2021-09-14 | 合肥立方制药股份有限公司 | 一种多沙唑嗪甲磺酸盐晶型、其制备方法及用途 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1287588B1 (it) * | 1996-12-13 | 1998-08-06 | Alfa Chem Ital | Forma cristallina del doxazosin mesilato e processo per la sua produzione |
| EP0849266B8 (fr) * | 1996-12-20 | 2007-10-03 | Heumann PCS GmbH | Nouvelle forme polymorphique de mésylate de doxazosin (forme III) |
| DE19800214A1 (de) * | 1998-01-06 | 1999-07-15 | Knoll Ag | Verfahren zur Herstellung von Doxazosin-Mcsylat in einer als Form A bezeichneten Kristallmodifikation und ein Zwischenprodukt dafür |
-
1999
- 1999-03-18 DE DE19912063A patent/DE19912063A1/de not_active Withdrawn
-
2000
- 2000-03-06 CN CN00805209A patent/CN1352643A/zh active Pending
- 2000-03-06 EP EP00918763A patent/EP1165548A1/fr not_active Withdrawn
- 2000-03-06 WO PCT/EP2000/001939 patent/WO2000056731A1/fr not_active Ceased
- 2000-03-06 TR TR2001/02730T patent/TR200102730T2/xx unknown
- 2000-03-06 PL PL00350088A patent/PL350088A1/xx unknown
- 2000-03-06 AU AU39608/00A patent/AU3960800A/en not_active Abandoned
- 2000-03-06 CZ CZ20013347A patent/CZ20013347A3/cs unknown
- 2000-03-06 HU HU0200663A patent/HUP0200663A2/hu unknown
- 2000-03-06 KR KR1020017011780A patent/KR20010113753A/ko not_active Withdrawn
- 2000-03-06 CA CA002367903A patent/CA2367903A1/fr not_active Abandoned
- 2000-03-06 IL IL14494400A patent/IL144944A0/xx unknown
- 2000-03-06 JP JP2000606592A patent/JP2002540109A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JP2002540109A (ja) | 2002-11-26 |
| PL350088A1 (en) | 2002-11-04 |
| TR200102730T2 (tr) | 2002-06-21 |
| WO2000056731A1 (fr) | 2000-09-28 |
| CZ20013347A3 (cs) | 2002-01-16 |
| EP1165548A1 (fr) | 2002-01-02 |
| CN1352643A (zh) | 2002-06-05 |
| KR20010113753A (ko) | 2001-12-28 |
| IL144944A0 (en) | 2002-06-30 |
| DE19912063A1 (de) | 2000-09-21 |
| AU3960800A (en) | 2000-10-09 |
| HUP0200663A2 (en) | 2002-08-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |