WO2021188404A1 - Formes à l'état solide d'otéséconazole et leur procédé de préparation - Google Patents
Formes à l'état solide d'otéséconazole et leur procédé de préparation Download PDFInfo
- Publication number
- WO2021188404A1 WO2021188404A1 PCT/US2021/022284 US2021022284W WO2021188404A1 WO 2021188404 A1 WO2021188404 A1 WO 2021188404A1 US 2021022284 W US2021022284 W US 2021022284W WO 2021188404 A1 WO2021188404 A1 WO 2021188404A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- oteseconazole
- crystalline
- piperazine
- theta
- degrees
- Prior art date
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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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
Definitions
- the present disclosure includes processes for preparing the above mentioned pharmaceutical compositions.
- the processes include combining any one or a combination of the crystalline polymorph of Oteseconazole and/or crystalline Oteseconazole: Piperazine or the described solid state forms thereof with at least one pharmaceutically acceptable excipient.
- the crystalline polymorph of Oteseconazole and/or crystalline Oteseconazole Piperazine as defined herein and the pharmaceutical compositions or formulations of the crystalline polymorph of Oteseconazole and/or crystalline Oteseconazole: Piperazine may be used as medicaments, such as for the treatment of acute Vulvovaginal Candidiasis or Recurrent Vulvovaginal Candidiasis (RVVC) , or tinea pedis, onychomycosis, candidiasis, meningitis (e.g., cryptococcal meningitis), or mucormycosis.
- RVVC Recurrent Vulvovaginal Candidiasis
- the crystalline polymorph of Oteseconazole and crystalline Oteseconazole may have advantageous properties selected from at least one of the following: chemical purity, flowability, solubility, dissolution rate, morphology or crystal habit, stability, such as chemical stability as well as thermal and mechanical stability with respect to polymorphic conversion, stability towards dehydration and/or storage stability, low content of residual solvent, a lower degree of hygroscopicity, flowability, and advantageous processing and handling characteristics such as compressibility and bulk density.
- Crystalline Form 01 of Oteseconazole may be further characterized by an X-ray powder diffraction pattern having peaks at 11.0, 12.8, 17.3, 17.7 and 26.7 degrees 2-theta ⁇ 0.2 degrees 2-theta, and also having any one, two, three, four or five additional peaks selected from 14.9, 18.9, 21.5, 23.2 and 24.5 degrees 2-theta ⁇ 0.2 degrees 2-theta.
- crystalline Form 01 of Oteseconazole is isolated.
- the crystalline Oteseconazole Form 01 described herein may be substantially free of any other solid state forms of Oteseconazole.
- crystalline Oteseconazole Form 01 according to any aspect or embodiment of the present invention contains about 20% (w/w) or less, about 10% (w/w) or less, about 5% (w/w) or less, about 2% (w/w) or less, about 1% (w/w) or less, or about 0% (w/w) of any other forms of Oteseconazole as measured, for example, by XRPD.
- Oteseconazole Form 01 which comprises a sol vent/ anti solvent crystallization.
- Oteseconazole Form 01 may be prepared by a solvent/anti solvent crystallisation wherein the solvent may be an alcohol, or an ester, wherein the alcohol amyl alcohol, isobutanol or cyclohexanol.
- the ester is a C2-6 ester, more preferably ethyl formate, methyl formate, isobutyl acetate, or ethyl acetate.
- the antisolvent may be used in an amount of about 2 to about 30 vol, about 5 to about 20 vol, or about 10 vol.
- the alkane is cooled to a temperature of about 0°C to about 10°C, about 0 to about 5°C, or about 0°C to about 4°C, or about 2°C, optionally with stirring.
- Crystalline Form PCC1 of Oteseconazole Piperazine may be characterized by each of the above characteristics alone or by all possible combinations, e.g., an XRPD pattern having peaks at 9.2, 12.2, 18.5, 22.5 and 23.5 degrees 2-theta ⁇ 0.2 degrees 2-theta; an XRPD pattern as depicted in Figure 2, and combinations thereof.
- the present disclosure relates to crystalline Oteseconazole: Piperazine and a solid state form thereof.
- the present disclosure also relates to pharmaceutical compositions including the solid state form of Oteseconazole: Piperazine.
- the present disclosure provides the above described crystalline polymorphs of Oteseconazole and crystalline Oteseconazole: Piperazine for use in the preparation of pharmaceutical compositions comprising Oteseconazole and crystalline Oteseconazole: Piperazine and/or crystalline polymorphs thereof.
- the present disclosure also encompasses the use of crystalline polymorphs of Oteseconazole and crystalline Oteseconazole: Piperazine of the present disclosure for the preparation of pharmaceutical compositions of crystalline polymorph Oteseconazole, crystalline Oteseconazole: Piperazine and/or crystalline polymorphs thereof.
- the dissolution rate of a compacted solid pharmaceutical composition in the patient's stomach can be increased by the addition of a disintegrant to the composition.
- Disintegrants include alginic acid, carboxymethylcellulose calcium, carboxymethylcellulose sodium (e.g., Ac- Di-Sol®, Primellose®), colloidal silicon dioxide, croscarmellose sodium, crospovidone (e.g., Kollidon®, Polyplasdone®), guar gum, magnesium aluminum silicate, methyl cellulose, microcrystalline cellulose, polacrilin potassium, powdered cellulose, pregelatinized starch, sodium alginate, sodium starch glycolate (e.g., Explotab®), and starch.
- alginic acid include alginic acid, carboxymethylcellulose calcium, carboxymethylcellulose sodium (e.g., Ac- Di-Sol®, Primellose®), colloidal silicon dioxide, croscarmellose sodium, crospovidone (e.g., Kollidon®, Polyplas
- the solid compositions of the present disclosure include powders, granulates, aggregates, and compacted compositions.
- the dosages include dosages suitable for oral, buccal, rectal, parenteral (including subcutaneous, intramuscular, and intravenous), inhalant, and ophthalmic administration. Although the most suitable administration in any given case will depend on the nature and severity of the condition being treated, in embodiments the route of administration is oral.
- the dosages can be conveniently presented in unit dosage form and prepared by any of the methods well-known in the pharmaceutical arts.
- Scanning parameters range: 2-40 degrees two-theta; scan mode: continuous scan; step size:
- Oteseconazole can be prepared according to methods known from the literature, for example U.S. Patent No. 8,236,962.
- Example 7 Preparation of crystalline Oteseconazole:piperazine Form PCC1 [00127] Oteseconazole (1 gram, 1.89 mmol) was added to THF (3 ml, 3 V) at 40°C, under stirring to give clear solution. The obtained hot clear solution was mechanically filtrated upon filter disk. Then, piperazine (0.5 eq., 0.945 mmol) was added to the stirred solution upon 40°C. The reaction mixture was stirred at 40°C for additional 10 minutes followed by cooling spontaneously to room temperature. Next, the clear mixture was cooled to 4°C and continues stirring upon this temperature, followed by addition of cold n-heptane (15ml, 15 V) and kept with stirring for minimum 2 hours at 4°C to give precipitant.
- THF 3 ml, 3 V
- piperazine 0.5 eq., 0.945 mmol
Abstract
La présente divulgation porte sur l'otéséconazole et des formes à l'état solide d'otéséconazole : La pipérazine, dans des modes de réalisation sous formes polymorphes cristallines d'otéséconazole et de l'otéséconazole cristallin : La pipérazine, des procédés de préparation correspondants, et des compositions pharmaceutiques associées.
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
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US202062991635P | 2020-03-19 | 2020-03-19 | |
US62/991,635 | 2020-03-19 | ||
US202063010769P | 2020-04-16 | 2020-04-16 | |
US63/010,769 | 2020-04-16 |
Publications (1)
Publication Number | Publication Date |
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WO2021188404A1 true WO2021188404A1 (fr) | 2021-09-23 |
Family
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PCT/US2021/022284 WO2021188404A1 (fr) | 2020-03-19 | 2021-03-15 | Formes à l'état solide d'otéséconazole et leur procédé de préparation |
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Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8236962B2 (en) | 2010-04-24 | 2012-08-07 | Viamet Pharmaceuticals, Inc. | Metalloenzyme inhibitor compounds |
WO2015143180A1 (fr) * | 2014-03-19 | 2015-09-24 | Viamet Pharmaceuticals, Inc. | Procédé de préparation d'un composé antifongique |
WO2016149486A1 (fr) * | 2015-03-19 | 2016-09-22 | Viamet Pharmaceuticals, Inc. | Composés antifongiques et procédés de fabrication |
WO2017049080A1 (fr) * | 2015-09-18 | 2017-03-23 | Viamet Pharmaceuticals, Inc. | Procédé de préparation d'un composé antifongique |
-
2021
- 2021-03-15 WO PCT/US2021/022284 patent/WO2021188404A1/fr active Application Filing
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8236962B2 (en) | 2010-04-24 | 2012-08-07 | Viamet Pharmaceuticals, Inc. | Metalloenzyme inhibitor compounds |
WO2015143180A1 (fr) * | 2014-03-19 | 2015-09-24 | Viamet Pharmaceuticals, Inc. | Procédé de préparation d'un composé antifongique |
WO2016149486A1 (fr) * | 2015-03-19 | 2016-09-22 | Viamet Pharmaceuticals, Inc. | Composés antifongiques et procédés de fabrication |
US9840492B2 (en) | 2015-03-19 | 2017-12-12 | Viamet Pharmaceuticals, Inc. | Antifungal compounds and processes for making |
US10370353B2 (en) | 2015-03-19 | 2019-08-06 | Mycovia Pharmaceuticals, Inc. | Antifungal compounds and processes for making |
US10414751B2 (en) | 2015-03-19 | 2019-09-17 | Mycovia Pharmaceuticals, Inc. | Antifungal compounds and processes for making |
US10676459B2 (en) | 2015-03-19 | 2020-06-09 | Mycovia Pharmaceuticals, Inc. | Antifungal compounds and processes for making |
WO2017049080A1 (fr) * | 2015-09-18 | 2017-03-23 | Viamet Pharmaceuticals, Inc. | Procédé de préparation d'un composé antifongique |
Non-Patent Citations (3)
Title |
---|
ANSEL ET AL.: "Pharmaceutical Dosage Forms and Drug Delivery Systems" |
BRAND STEPHEN R. ET AL: "A phase 2, randomized, double-blind, placebo-controlled, dose-ranging study to evaluate the efficacy and safety of orally administered VT-1161 in the treatment of recurrent vulvovaginal candidiasis", AMERICAN JOURNAL OF OBSTETRICS & GYNECOLOGY, vol. 218, no. 6, 1 June 2018 (2018-06-01), US, pages 624.e1 - 624.e9, XP055803442, ISSN: 0002-9378, DOI: 10.1016/j.ajog.2018.03.001 * |
MINO R CAIRA ED - MONTCHAMP JEAN-LUC: "CRYSTALLINE POLYMORPHISM OF ORGANIC COMPOUNDS", TOPICS IN CURRENT CHEMISTRY; [TOPICS IN CURRENT CHEMISTRY], SPRINGER, BERLIN, DE, vol. 198, 1 January 1998 (1998-01-01), pages 163 - 208, XP001156954, ISSN: 0340-1022, [retrieved on 19990226], DOI: 10.1007/3-540-69178-2_5 * |
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