HUP0400270A2 - Nagytisztaságú, meghatározott szemcseméretű butoconazol-nitrát és eljárás előállítására - Google Patents
Nagytisztaságú, meghatározott szemcseméretű butoconazol-nitrát és eljárás előállításáraInfo
- Publication number
- HUP0400270A2 HUP0400270A2 HU0400270A HUP0400270A HUP0400270A2 HU P0400270 A2 HUP0400270 A2 HU P0400270A2 HU 0400270 A HU0400270 A HU 0400270A HU P0400270 A HUP0400270 A HU P0400270A HU P0400270 A2 HUP0400270 A2 HU P0400270A2
- Authority
- HU
- Hungary
- Prior art keywords
- nitrate
- formula
- reaction
- compound
- butoconazole
- Prior art date
Links
- ZHPWRQIPPNZNML-UHFFFAOYSA-N butoconazole nitrate Chemical compound O[N+]([O-])=O.C1=CC(Cl)=CC=C1CCC(SC=1C(=CC=CC=1Cl)Cl)CN1C=NC=C1 ZHPWRQIPPNZNML-UHFFFAOYSA-N 0.000 title abstract 5
- 229960002120 butoconazole nitrate Drugs 0.000 title abstract 4
- 238000000034 method Methods 0.000 title abstract 3
- 239000002245 particle Substances 0.000 title abstract 3
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 5
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 abstract 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 abstract 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 abstract 2
- 239000000243 solution Substances 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- 239000000126 substance Substances 0.000 abstract 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 abstract 1
- VMGHYAYPTGFWEV-UHFFFAOYSA-N 1-chloro-4-(4-chlorophenyl)butan-2-ol Chemical compound ClCC(O)CCC1=CC=C(Cl)C=C1 VMGHYAYPTGFWEV-UHFFFAOYSA-N 0.000 abstract 1
- JBISHCXLCGVPGW-UHFFFAOYSA-N 2,6-dichlorobenzenethiol Chemical compound SC1=C(Cl)C=CC=C1Cl JBISHCXLCGVPGW-UHFFFAOYSA-N 0.000 abstract 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 abstract 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 229960005074 butoconazole Drugs 0.000 abstract 1
- SWLMUYACZKCSHZ-UHFFFAOYSA-N butoconazole Chemical compound C1=CC(Cl)=CC=C1CCC(SC=1C(=CC=CC=1Cl)Cl)CN1C=NC=C1 SWLMUYACZKCSHZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000012535 impurity Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 150000002823 nitrates Chemical class 0.000 abstract 1
- 229910017604 nitric acid Inorganic materials 0.000 abstract 1
- 239000000546 pharmaceutical excipient Substances 0.000 abstract 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- 239000003444 phase transfer catalyst Substances 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 239000011877 solvent mixture Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C07D233/60—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to ring nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Inorganic Compounds Of Heavy Metals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
A találmány célja nagytisztaságú (I) képletű butoconazol-nitrát(kémiai nevén: 1-[4-(4-klórfenil)-2-(2,6-diklórfeniltio)-n-butil]-imidazol-nitrát), amely legfeljebb 0,10 tömeg% kémiai szennyezésttartalmaz és az anyag szemcséinek legalább 95%-a 75 mm-nél, legalább99%-a pedig 250 mm-nél kisebb átmérőjű. A találmány célja továbbáeljárás a fenti vegyület előállítására 1-klór-4(4-klórfenil)-2-butanolból és imidazolból kiindulva, a kapott (IV) képletű vegyülettionilkloriddal végzett reakciója és a kapott (V) képletű vegyület2,6-diklór-tiofenollal végzett reakciója útján, olyan módon, hogy azeljárás első lépését vízzel nem elegyedő oldószer és alkáli-fémhidroxid vagy karbonát vizes oldatának elegyében, fázistranszferkatalizátor jelenlétében végzik, majd a második lépést 1,2-diklóretánoldószerben, dimetilformamid jelenlétében hajtják végre és a reaktánstionilkloridot 1-1,2 mólnyi mennyiségben alkalmazzák a (IV) képletűvegyületre vonatkoztatva, továbbá a harmadik lépésben végrehajtottreakció termékét nem izolálják, és az így nyert oldatban lévőbutoconazolt (VI) salétromsavval kezelve nitrát-só formában izolálják.A találmány további tárgya a fent jellemzett szemcseméretű vegyületelőállítása nyers butoconazol-nitrátból kiindulva, olyan módon, hogy akiindulási anyagot 1-1,5:1 térfogatarányú metanol és metil-izobutil-keton oldószerelegyben feloldják és az oldatot +5 - -15 °C-ra hűtöttmetil-izobutil-ketonhoz adagolják, majd a kapott terméket izolálják.Tárgya a találmánynak továbbá gyógyszerkészítmény, amely hatóanyagkéntnagytisztaságú, meghatározott szemcseméretű butoconazol-nitrátot,valamint önmagukban ismert segédanyagokat tartalmaz.
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU0400270A HUP0400270A3 (en) | 2004-01-27 | 2004-01-27 | High purity butoconazole nitrate having a predetermined particle size and process for the production of the same |
| EP05702171A EP1709005B1 (en) | 2004-01-27 | 2005-01-25 | High purity butoconazole nitrate with specified particle size and a process for preparation thereof |
| JP2006550311A JP4795973B2 (ja) | 2004-01-27 | 2005-01-25 | 特定の粒径を備えた高純度硝酸ブトコナゾール及びその製造方法 |
| UAA200609221A UA87674C2 (ru) | 2004-01-27 | 2005-01-25 | Способ получения нитрата бутоконазола |
| EA200601373A EA009238B1 (ru) | 2004-01-27 | 2005-01-25 | Нитрат бутоконазола высокой степени чистоты с частицами заданного размера и способ его получения |
| EP07023914A EP1903035A3 (en) | 2004-01-27 | 2005-01-25 | High purity butoconazole nitrate with specified particle size and a process for preparation of thereof |
| PCT/HU2005/000002 WO2005070897A1 (en) | 2004-01-27 | 2005-01-25 | High purity butoconazole nitrate with specified particle size and a process for preparation thereof |
| US10/584,662 US7625935B2 (en) | 2004-01-27 | 2005-01-25 | High purity butoconazole nitrate with specified particle size and a process for the preparation thereof |
| DE602005015417T DE602005015417D1 (de) | 2004-01-27 | 2005-01-25 | Hochreines butoconazolnitrat mit spezifischer teilchengrösse und verfahren zu dessen herstellung |
| NO20063805A NO20063805L (no) | 2004-01-27 | 2006-08-25 | Hoyrent butokonazolnitrat med spesifisert partikkelstorrelse og en fremgangsmate for fremstilling derav |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU0400270A HUP0400270A3 (en) | 2004-01-27 | 2004-01-27 | High purity butoconazole nitrate having a predetermined particle size and process for the production of the same |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| HU0400270D0 HU0400270D0 (en) | 2004-04-28 |
| HUP0400270A2 true HUP0400270A2 (hu) | 2005-12-28 |
| HUP0400270A3 HUP0400270A3 (en) | 2007-09-28 |
Family
ID=89981937
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU0400270A HUP0400270A3 (en) | 2004-01-27 | 2004-01-27 | High purity butoconazole nitrate having a predetermined particle size and process for the production of the same |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US7625935B2 (hu) |
| EP (2) | EP1903035A3 (hu) |
| JP (1) | JP4795973B2 (hu) |
| DE (1) | DE602005015417D1 (hu) |
| EA (1) | EA009238B1 (hu) |
| HU (1) | HUP0400270A3 (hu) |
| NO (1) | NO20063805L (hu) |
| UA (1) | UA87674C2 (hu) |
| WO (1) | WO2005070897A1 (hu) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102649796A (zh) * | 2011-02-24 | 2012-08-29 | 四川滇虹医药开发有限公司 | 一种硝酸布康唑中间体的制备方法 |
| CN105198816B (zh) * | 2015-10-09 | 2018-05-01 | 株洲千金药业股份有限公司 | 一种工业化生产硝酸布康唑的方法 |
| CN105198814B (zh) * | 2015-10-09 | 2018-03-20 | 株洲千金药业股份有限公司 | 一种工业化生产硝酸布康唑中间体的方法 |
| CN105175338B (zh) * | 2015-10-09 | 2018-03-23 | 株洲千金药业股份有限公司 | 一种工业化生产硝酸布康唑中间体的方法 |
| CN105218456B (zh) * | 2015-10-09 | 2018-07-03 | 株洲千金药业股份有限公司 | 一种工业化生产硝酸布康唑的方法 |
| CN105175341B (zh) * | 2015-10-09 | 2017-12-26 | 株洲千金药业股份有限公司 | 一种工业化合成硝酸布康唑中间体的方法 |
| CN105218455B (zh) * | 2015-10-09 | 2018-07-03 | 株洲千金药业股份有限公司 | 一种工业化连续生产硝酸布康唑的方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1567431A (en) * | 1977-01-10 | 1980-05-14 | Syntex Inc | 1-(2-(halophenylthio)-4-(p-chloro- or-flrorophenyl)-n-butyl) imidazoles |
-
2004
- 2004-01-27 HU HU0400270A patent/HUP0400270A3/hu unknown
-
2005
- 2005-01-25 EP EP07023914A patent/EP1903035A3/en not_active Withdrawn
- 2005-01-25 UA UAA200609221A patent/UA87674C2/ru unknown
- 2005-01-25 DE DE602005015417T patent/DE602005015417D1/de active Active
- 2005-01-25 EP EP05702171A patent/EP1709005B1/en active Active
- 2005-01-25 US US10/584,662 patent/US7625935B2/en not_active Expired - Fee Related
- 2005-01-25 JP JP2006550311A patent/JP4795973B2/ja not_active Expired - Fee Related
- 2005-01-25 WO PCT/HU2005/000002 patent/WO2005070897A1/en active Application Filing
- 2005-01-25 EA EA200601373A patent/EA009238B1/ru not_active IP Right Cessation
-
2006
- 2006-08-25 NO NO20063805A patent/NO20063805L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| UA87674C2 (ru) | 2009-08-10 |
| WO2005070897A1 (en) | 2005-08-04 |
| JP2007519699A (ja) | 2007-07-19 |
| EA009238B1 (ru) | 2007-12-28 |
| US20080221190A1 (en) | 2008-09-11 |
| EP1903035A2 (en) | 2008-03-26 |
| EA200601373A1 (ru) | 2006-12-29 |
| EP1709005B1 (en) | 2009-07-15 |
| EP1709005A1 (en) | 2006-10-11 |
| HUP0400270A3 (en) | 2007-09-28 |
| NO20063805L (no) | 2006-08-25 |
| EP1903035A3 (en) | 2009-01-07 |
| DE602005015417D1 (de) | 2009-08-27 |
| JP4795973B2 (ja) | 2011-10-19 |
| US7625935B2 (en) | 2009-12-01 |
| HU0400270D0 (en) | 2004-04-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HC9A | Change of name, address |
Owner name: RICHTER GEDEON NYRT., HU Free format text: FORMER OWNER(S): RICHTER GEDEON VEGYESZETI GYAR RT., HU |
|
| FA9A | Lapse of provisional patent protection due to relinquishment or protection considered relinquished |