CA2974180A1 - Crystalline forms of efinaconazole - Google Patents
Crystalline forms of efinaconazole Download PDFInfo
- Publication number
- CA2974180A1 CA2974180A1 CA2974180A CA2974180A CA2974180A1 CA 2974180 A1 CA2974180 A1 CA 2974180A1 CA 2974180 A CA2974180 A CA 2974180A CA 2974180 A CA2974180 A CA 2974180A CA 2974180 A1 CA2974180 A1 CA 2974180A1
- Authority
- CA
- Canada
- Prior art keywords
- efinaconazole
- crystalline
- theta
- degrees
- mixture
- 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
- NFEZZTICAUWDHU-RDTXWAMCSA-N efinaconazole Chemical compound N1([C@H](C)[C@](O)(CN2N=CN=C2)C=2C(=CC(F)=CC=2)F)CCC(=C)CC1 NFEZZTICAUWDHU-RDTXWAMCSA-N 0.000 title claims abstract description 111
- 229960003937 efinaconazole Drugs 0.000 title claims abstract description 60
- 238000002360 preparation method Methods 0.000 claims abstract description 17
- 239000000203 mixture Substances 0.000 claims description 28
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 25
- 238000002844 melting Methods 0.000 claims description 12
- 230000008018 melting Effects 0.000 claims description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 238000000034 method Methods 0.000 abstract description 19
- -1 efinaconazole p-toluenesulfonate salt Chemical class 0.000 abstract description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 39
- 239000013078 crystal Substances 0.000 description 34
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 238000001237 Raman spectrum Methods 0.000 description 11
- 238000001914 filtration Methods 0.000 description 10
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 9
- 238000001757 thermogravimetry curve Methods 0.000 description 9
- 239000012296 anti-solvent Substances 0.000 description 7
- 238000004090 dissolution Methods 0.000 description 7
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 238000002441 X-ray diffraction Methods 0.000 description 5
- 238000000113 differential scanning calorimetry Methods 0.000 description 5
- 238000001816 cooling Methods 0.000 description 4
- 229960004132 diethyl ether Drugs 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 208000010195 Onychomycosis Diseases 0.000 description 2
- 238000001069 Raman spectroscopy Methods 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 201000005882 tinea unguium Diseases 0.000 description 2
- 101100481019 Nicotiana tabacum TGA1A gene Proteins 0.000 description 1
- 101150092207 TGA1 gene Proteins 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 238000007416 differential thermogravimetric analysis Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 229940100613 topical solution Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/12—Carboxylic acids; Salts or anhydrides thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/08—Solutions
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Dermatology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562105390P | 2015-01-20 | 2015-01-20 | |
| US62/105,390 | 2015-01-20 | ||
| PCT/IL2015/051171 WO2016116919A1 (en) | 2015-01-20 | 2015-12-02 | Crystalline forms of efinaconazole |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2974180A1 true CA2974180A1 (en) | 2016-07-28 |
Family
ID=56416514
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2974180A Abandoned CA2974180A1 (en) | 2015-01-20 | 2015-12-02 | Crystalline forms of efinaconazole |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US20180002310A1 (enExample) |
| EP (1) | EP3247399A4 (enExample) |
| JP (1) | JP2018502165A (enExample) |
| CN (1) | CN107427585A (enExample) |
| AU (1) | AU2015379251A1 (enExample) |
| CA (1) | CA2974180A1 (enExample) |
| IL (1) | IL253479A0 (enExample) |
| WO (1) | WO2016116919A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106995434A (zh) * | 2016-01-25 | 2017-08-01 | 广东东阳光药业有限公司 | 一种三唑类抗真菌药的晶型及其制备方法 |
| TWI772425B (zh) * | 2017-05-19 | 2022-08-01 | 日商科研製藥股份有限公司 | 艾菲康唑（ｅｆｉｎａｃｏｎａｚｏｌｅ）之製造及純化方法 |
| CA3115742C (en) * | 2018-12-29 | 2023-10-03 | Viwit Pharmaceutical Co., Ltd. | Preparation method for efinaconazole |
| JP2021054781A (ja) * | 2019-09-26 | 2021-04-08 | デボン エルエス，リミテッド | 共結晶形エフィナコナゾール、及びその製造方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3437695B2 (ja) * | 1993-05-10 | 2003-08-18 | 科研製薬株式会社 | アゾリルアミン誘導体 |
| WO1994026734A1 (fr) * | 1993-05-10 | 1994-11-24 | Kaken Pharmaceutical Co., Ltd. | Derive d'azolylamine |
| DE60042453D1 (de) * | 1999-07-28 | 2009-08-06 | Kaken Pharma Co Ltd | Verfahren zum nachweis pathogener mikroorganismen und antimikrobieller mittel, verfahren zum nachweis der arzneimittelwirkung antimikrobieller mittel und antimikrobielle mittel |
| PT2116243E (pt) * | 2006-12-28 | 2010-10-26 | Kaken Pharma Co Ltd | Composição de gel para tratamento de micoses |
| WO2008124131A1 (en) * | 2007-04-05 | 2008-10-16 | The John Hopkins University | Antifungal agents as neuroprotectants |
| US20090175810A1 (en) * | 2008-01-03 | 2009-07-09 | Gareth Winckle | Compositions and methods for treating diseases of the nail |
| FR2938066B1 (fr) * | 2008-11-06 | 2010-12-17 | Centre Nat Rech Scient | Systeme et procede d'analyse quantitative de la composition elementaire de la matiere par spectroscopie du plasma induit par laser (libs) |
| ES2556782T3 (es) * | 2010-08-31 | 2016-01-20 | Kaken Pharmaceutical Co., Ltd. | Procedimiento para producir derivados de 1-triazol-2-butanol |
| CN104292214B (zh) * | 2014-09-24 | 2017-04-05 | 南京华威医药科技开发有限公司 | 艾氟康唑及其中间体的合成方法 |
| CN104327047B (zh) * | 2014-10-17 | 2016-04-06 | 苏州明锐医药科技有限公司 | 艾菲康唑的制备方法 |
| US10479776B2 (en) * | 2015-05-12 | 2019-11-19 | Lupin Limited | Process for the preparation of Efinaconazole |
| US10125115B2 (en) * | 2015-06-04 | 2018-11-13 | Glenmark Pharmaceuticals Limited | Process for the preparation of efinaconazole |
-
2015
- 2015-12-02 EP EP15878656.6A patent/EP3247399A4/en not_active Withdrawn
- 2015-12-02 WO PCT/IL2015/051171 patent/WO2016116919A1/en not_active Ceased
- 2015-12-02 JP JP2017555872A patent/JP2018502165A/ja active Pending
- 2015-12-02 CN CN201580073938.9A patent/CN107427585A/zh active Pending
- 2015-12-02 CA CA2974180A patent/CA2974180A1/en not_active Abandoned
- 2015-12-02 AU AU2015379251A patent/AU2015379251A1/en not_active Abandoned
- 2015-12-02 US US15/544,173 patent/US20180002310A1/en not_active Abandoned
-
2017
- 2017-07-13 IL IL253479A patent/IL253479A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US20180002310A1 (en) | 2018-01-04 |
| AU2015379251A1 (en) | 2017-07-27 |
| WO2016116919A1 (en) | 2016-07-28 |
| JP2018502165A (ja) | 2018-01-25 |
| EP3247399A4 (en) | 2018-09-05 |
| IL253479A0 (en) | 2017-09-28 |
| CN107427585A (zh) | 2017-12-01 |
| EP3247399A1 (en) | 2017-11-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20180130 |
|
| FZDE | Discontinued |
Effective date: 20200831 |