ES2493940T3 - Una forma amorfa y una forma cristalina de hemitartrato de genz 112638 como inhibidor de glucosilceramida sintasa - Google Patents
Una forma amorfa y una forma cristalina de hemitartrato de genz 112638 como inhibidor de glucosilceramida sintasa Download PDFInfo
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- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/4025—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil not condensed and containing further heterocyclic rings, e.g. cromakalim
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- 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
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/357—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having two or more oxygen atoms in the same ring, e.g. crown ethers, guanadrel
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- C07C59/235—Saturated compounds containing more than one carboxyl group
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- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
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- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D319/18—Ethylenedioxybenzenes, not substituted on the hetero ring
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- 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
- C07D405/06—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 carbon chain containing only aliphatic carbon atoms
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Abstract
Una composición farmacéutica que comprende la sal de hemitartrato de un compuesto representado mediante la siguiente fórmula estructural:**Fórmula** y un vehículo o diluyente farmacéuticamente aceptable.
Description
E10785289
19-08-2014
Preparación de Hemitartrato de Fórmula (I) en agua al 1% en acetona.
Se disolvió Base Libre de Formula (I) (10 g/24,7 mmoles) en agua al 1%/acetona 120 ml o 240 ml a temperatura ambiente. Se disolvió ácido L-tartárico, 1,85 g/12,3 mmoles, en agua al 1%/acetona 60 ml o 120 ml (N o 2N) mediante calentamiento hasta 40-45ºC, y esta disolución se añadió a la primera disolución. Después de 1 hora sin 5 precipitación, se añadió 1 mg de Hemitartrato de Formula (I) como un cristal de siembra. La precipitación se produjo después de 5 minutos, y la reacción se continuó agitando durante 30 minutos. La reacción se calentó entonces a reflujo durante 5 minutos (el precipitado no era completamente soluble) y después se enfrió hasta la temperatura ambiente en un baño de agua a 20-22ºC. Se formó un precipitado, y la reacción se continuó agitando durante 3 horas. El producto final se recogió mediante filtración y se lavó con acetona, 2 x 40 ml, y después se secó en el
10 horno de vacío a 55-60ºC durante 16 horas. El peso del producto fue 8,62 g 73% de rendimiento.
Recristalización de Hemitartrato de Fórmula (I) en metanol al 5% en acetona.
Se disolvió Hemitartrato de Fórmula (I) (3,06 g) en 116 ml de metanol al 5% en acetona a reflujo. La disolución se enfrió hasta la temperatura ambiente y se agitó a temperatura ambiente durante 2 h. El precipitado blanco se filtró y se lavó con 10 ml de metanol al 5% en acetona y después acetona (15 ml). Después de secar a vacío durante 18 h a
15 55-60ºC, se recibieron 2,38 g de Hemitartrato de Fórmula (I) (78% de recuperación).
Recristalización of Hemitartrato de Fórmula (I) en H2O al 1% en acetona.
Se disolvió Hemitartrato de Fórmula (I) (3,05 g) en 125 ml de H2O al 1% en acetona a reflujo. La disolución se enfrió hasta la temperatura ambiente y se agitó a temperatura ambiente durante 2 h. El precipitado blanco se filtró y se lavó con 10 ml de H2O al 1% en acetona y después acetona (15 ml). Después de secar a vacío toda la noche a 55-60ºC,
20 se obtuvieron 2,35 g de Hemitartrato de Fórmula (I) (77% de recuperación).
Ejemplo 2: Preparación de Hemitartrato de Formula (I) cristalino
Hemitartrato de Formula (I) se cristalizó mediante varios métodos. El Lote 1 se preparó usando disolventes de acetato de etilo/acetona, y se secó a temperatura ambiente. El Lote 3 se preparó usando disolventes de acetato de etilo/acetona, y se recristalizó en acetato de etilo. El Lote 4 se recristalizó en acetona usando material del Lote 1. El
25 Lote 5 se recristalizó en isopropanol. El Lote 7 se preparó usando un disolvente de acetato de etilo/acetona similar al Lote 1, pero en una escala mayor; el Lote 8 se preparó usando acetona solamente, sin cristalización posterior. El Lote 9 se preparó usando acetona solamente con un breve reflujo, y nuevamente sin recristalización posterior.
Tabla 1: Sumario de la identificación de polimorfismos de los Lotes 1-9 de Hemitartrato de Formula (I)
- Lote nº
- Método de realización Punto de fusión mediante DSC (ºC) Entalpía (J/g) Microscopio TGA
- 1
- Precipitación en acetona/acetato de etilo* 162 -81,4 Cristal 99,91% a 100ºC 98,73% a 175ºC
- 2
- Precipitación en acetona/acetato de etilosecado a temperatura ambiente * 164 -95,6 Cristal N/A
- 3
- Precipitación en acetona/acetato de etilosecado a 55-60ºC 166 -97,8 Cristal 100,0% a 100ºC 99,98% a 153ºC
- 4
- Recristallización en acetona 166 -107,2 Cristal 100,2% a 100ºC 100,2% a 153ºC
- 5
- Recristalización en isopropanol 166 -102,6 Cristal 100,0% a 100ºC 100,0% a 153ºC
- 7
- Precipitación en acetona/acetato de etilo 166 -99,4 Cristal** 100,1% a 100ºC 99,91% a 153ºC
- 8
- Precipitación en acetona 165 -100,7 Cristal** 100,0% a 100ºC 100,0% a 153ºC
14
E10785289
19-08-2014
**: las partículas tuvieron forma de placas y de varillas
Método de enfriamiento lento/rápido. Se disolvió Hemitartrato de Formula (I) en un disolvente de ensayo a 50-60ºC. La disolución resultante se dejó entonces enfriar hasta la temperatura ambiente (enfriamiento lento). Si no se formó ningún sólido después de un día, los viales se colocaron en un refrigerador. Para experimentos de enfriamiento rápido, la disolución resultante se dejó entonces enfriar en un refrigerador. Los sólidos se recogieron mediante filtración y se secaron al aire.
Tabla 4: Sumario de polimorfismo usando el enfoque de enfriamiento lento.
- Disolvente orgánico
- Forma sólida generada a partir de enfriamiento lento Punto de fusión mediante DSC (ºC) Entalpía (J/g) Microscopio TGA
- Etanol
- Sí 167 -106,2 Cristal** 100,1% a 100ºC 100,1% a 150ºC
- **: las partículas tuvieron forma de placas y de varillas
Tabla 5: Sumario de polimorfismo usando el enfoque de enfriamiento rápido.
- Disolvente orgánico
- Forma sólida generada a partir de enfriamiento rápido Punto de fusión mediante DSC (ºC) Entalpía (J/g) Microscopio TGA
- Etanol
- Sí 167 -106,2 Cristal** 100,0% a 100ºC 100,0% a 150ºC
- **: las partículas tuvieron forma de placas y de varillas
Método con antidisolventes. El Hemitartrato de Formula (I) se disolvió en un disolvente. Se añadió un antidisolvente a la disolución. Los sólidos que se formaron se recogieron mediante filtración y se secaron al aire.
Tabla 6: Sumario de identificación de polimorfismos usando el enfoque de antidisolventes
- Disolvente orgánico
- Forma sólida generada a partir de enfoque con antidisolventes Punto de fusión mediante DSC (ºC) Entalpía (J/g) Microscopio TGA
- Metanol/acetato de etilo
- Sí 167 -99,5 Cristal* 100,1% a 100ºC 100,1% a 150ºC
- Metanol/acetona
- Sí 167 -106,2 Cristal* 100,3% a 100ºC 100,2% a 150ºC
- Metanol/acetonitrilo
- No N/A N/A N/A N/A
- Metanol/tolueno
- No N/A N/A N/A N/A
- Metanol/THF
- No N/A N/A N/A N/A
- Metanol/TBME
- Sí 167 -102,0 Cristal* 100,2% a 100°C 100,1% a 150ºC
- Metanol/p-dioxano
- No N/A N/A N/A N/A
16
E10785289
19-08-2014
- Disolvente orgánico
- Forma sólida generada a partir de enfoque con antidisolventes Punto de fusión mediante DSC (ºC) Entalpía (J/g) Microscopio TGA
- Agua/THF
- No N/A N/A N/A N/A
- Agua/TMBE
- No N/A N/A N/A N/A
- Agua/isopropanol
- No N/A N/A N/A N/A
- Agua/acetonitrilo
- No N/A N/A N/A N/A
- Agua/acetona
- No N/A N/A N/A N/A
- Dicolorometano/heptano
- Sí 165 -89,2 Cristal** 100,0% a 100ºC 99,99% a 150ºC
- Dicolorometano/acetato de etilo
- Sí 167 -97,8 Cristal* 100,2% a 100ºC 100,1% a 150ºC
- Dicolorometano/tolueno
- Sí 164 -89,8 Cristal* 99,95% a 100ºC 99,86% a 150ºC
- Dicolorometano/TBME
- Sí 167 -98,6 Cristal** 100,0°C a 100ºC 99,91% a 150ºC
- Dicolorometano/pdioxano
- Sí (poca) N/A N/A N/A N/A
- Dicolorometano/isopropanol
- No N/A N/A N/A N/A
- *: Las partículas tenían forma de placa y de varilla. **: Las partículas individuales tuvieron más de un color de birrefringente. ***: Las partículas tuvieron forma de agujas y de varillas.
Ejemplo 3: Propiedades físicas de Hemitartrato de Formula (I)
Calorimetría de barrido diferencial (DSC). Los datos de DSC se recogieron en un instrumento TA Q100 utilizando nitrógeno como el gas de purga. Se pesaron exactamente aproximadamente 2-5 mg de muestra en una bandeja de 5 DSC de aluminio. La bandeja se cubrió con una tapa y se perforó con un fórceps. La celda de muestra se equilibró a 30ºC y se calentó a una velocidad de 10ºC por minuto hasta una temperatura final de 220ºC.
Microscopía de platina caliente. La microscopía de platina caliente se llevó a cabo usando una platina caliente Linkam (modelo FTIR 600) montada sobre un microscopio Leica DM LP equipado con una cámara Sony DXC970MD 3CCD para la recogida de imágenes. Se usó un objetivo 40x con luz polarizada para visualizar las muestras.
10 Cada una de las muestras se colocó entre dos cubreobjetos. Cada muestra se observó visualmente a medida que se calentaba la platina. Las imágenes se capturaron usando Links version 2.27 (Linkam). La platina caliente se calibró usando patrones de punto de fusión USP.
Se confirmó que la transición endotérmica observada en el perfil de DSC es una transición de fusión a una temperatura entre 160-163ºC mediante microscopía de platina caliente.
15 Ejemplo 4: Difracción de rayos X de polvo de Hemitartrato de Formula (I)
Todos los análisis de difracción de rayos X de polvo (XRPD) se realizaron en SSCI, Inc. (West Lafayette, IN 47906). Los análisis de XPRD se llevaron a cabo usando un difractómetro de rayos X de polvo Shimadzu XRD-6000, usando radiación CuK. El instrumento está equipado con un tubo de rayos X de foco fino. El voltaje y amperaje del tubo se ajustaron a 40 kV y 40 mA, respectivamente. Las ranuras de divergencia y de dispersión se ajustaron a 1º, y la 20 ranura receptora se ajustó a 0,15 mm. La radiación difractada se detectó mediante un detector de centelleo de NaI. Se usó el barrido continuo de theta dos theta a 3º/min. (0,4 s/0,02º etapa) de 2,5 a 40º 2. Se analizó un patrón de
17
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US26474809P | 2009-11-27 | 2009-11-27 | |
| US264748P | 2009-11-27 | ||
| PCT/US2010/057952 WO2011066352A1 (en) | 2009-11-27 | 2010-11-24 | An amorphous and a crystalline form of genz 112638 hemitartrat as inhibitor of glucosylceramide synthase |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ES2493940T3 true ES2493940T3 (es) | 2014-09-12 |
| ES2493940T5 ES2493940T5 (es) | 2021-11-23 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES16175117T Active ES2754398T3 (es) | 2009-11-27 | 2010-11-24 | Eliglustat (Genz 112638) como inhibidor de glucosilceramida-sintasa para uso en un método de tratamiento de la enfermedad de fabry o de gaucher, comprendiendo el método ajustar la dosis terapéutica individual al metabolismo P-450 del paciente |
| ES19182732T Active ES2875382T3 (es) | 2009-11-27 | 2010-11-24 | Composición farmacéutica del inhibidor de glucosilceramida sintasa Eliglustat para el tratamiento de la enfermedad de Gaucher, que comprende ajustar la dosis terapéutica individual al metabolismo de P450 del paciente |
| ES14164650.5T Active ES2586947T3 (es) | 2009-11-27 | 2010-11-24 | Genz 112638 para tratar la enfermedad de Gaucher o de Fabry en terapia de combinación |
| ES10785289T Active ES2493940T5 (es) | 2009-11-27 | 2010-11-24 | Una forma amorfa y una forma cristalina de hemitartrato de genz 112638 como inhibidor de glucosilceramida sintasa |
Family Applications Before (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES16175117T Active ES2754398T3 (es) | 2009-11-27 | 2010-11-24 | Eliglustat (Genz 112638) como inhibidor de glucosilceramida-sintasa para uso en un método de tratamiento de la enfermedad de fabry o de gaucher, comprendiendo el método ajustar la dosis terapéutica individual al metabolismo P-450 del paciente |
| ES19182732T Active ES2875382T3 (es) | 2009-11-27 | 2010-11-24 | Composición farmacéutica del inhibidor de glucosilceramida sintasa Eliglustat para el tratamiento de la enfermedad de Gaucher, que comprende ajustar la dosis terapéutica individual al metabolismo de P450 del paciente |
| ES14164650.5T Active ES2586947T3 (es) | 2009-11-27 | 2010-11-24 | Genz 112638 para tratar la enfermedad de Gaucher o de Fabry en terapia de combinación |
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| Country | Link |
|---|---|
| US (6) | US11458119B2 (es) |
| EP (5) | EP2796457B1 (es) |
| JP (6) | JP2013512252A (es) |
| KR (6) | KR102073207B1 (es) |
| CN (5) | CN112521367B (es) |
| AR (3) | AR079152A1 (es) |
| AU (3) | AU2010324810B2 (es) |
| BR (1) | BR112012012947B8 (es) |
| CA (3) | CA2781676C (es) |
| CL (2) | CL2012001348A1 (es) |
| CR (1) | CR20120277A (es) |
| CY (3) | CY1115880T1 (es) |
| DK (3) | DK2796457T3 (es) |
| DO (2) | DOP2012000141A (es) |
| EA (3) | EA023923B1 (es) |
| EC (2) | ECSP12011926A (es) |
| ES (4) | ES2754398T3 (es) |
| GT (1) | GT201200161A (es) |
| HR (3) | HRP20140780T4 (es) |
| HU (2) | HUE029371T2 (es) |
| IL (4) | IL310635A (es) |
| LT (2) | LT3133070T (es) |
| MA (1) | MA33838B1 (es) |
| ME (1) | ME02477B (es) |
| MX (2) | MX358345B (es) |
| MY (2) | MY192644A (es) |
| NI (1) | NI201200096A (es) |
| NZ (3) | NZ625712A (es) |
| PE (2) | PE20121337A1 (es) |
| PH (2) | PH12012501048A1 (es) |
| PL (4) | PL2504332T5 (es) |
| PT (4) | PT2504332E (es) |
| RS (3) | RS54978B1 (es) |
| SG (2) | SG10201407881WA (es) |
| SI (3) | SI2796457T1 (es) |
| SM (1) | SMT201600273B (es) |
| TN (1) | TN2012000237A1 (es) |
| TW (3) | TWI656873B (es) |
| UA (1) | UA113491C2 (es) |
| WO (1) | WO2011066352A1 (es) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006007560A2 (en) | 2004-07-01 | 2006-01-19 | University Of Pennsylvania | Targeted protein replacement for the treatment of lysosomal storage disorders |
| NZ625712A (en) | 2009-11-27 | 2016-02-26 | Genzyme Corp | An amorphous and a crystalline form of genz 112638 hemitartrate as inhibitor of glucosylceramide synthase |
| EP2721151B1 (en) * | 2011-06-20 | 2017-12-06 | Mount Sinai School Of Medicine | Anti-tnf-therapy for the mucopolysaccharidoses and other lysosomal disorders |
| SI2753346T1 (sl) | 2011-09-07 | 2020-09-30 | Mount Sinai School Of Medicine | Ceramidaza in diferenciacija celic |
| WO2013078413A1 (en) * | 2011-11-22 | 2013-05-30 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Modulators of lipid storage |
| HUE051020T2 (hu) | 2012-06-01 | 2021-01-28 | Icahn School Med Mount Sinai | A ceramid szintjei a fertõzések kezelésében és megelõzésében |
| WO2014160390A1 (en) | 2013-03-14 | 2014-10-02 | Icahn School Of Medicine At Mount Sinai | Therapeutic acid ceramidase compositions and methods of making and using them |
| US10227323B2 (en) * | 2013-09-20 | 2019-03-12 | Biomarin Pharmaceutical Inc. | Glucosylceramide synthase inhibitors for the treatment of diseases |
| EP3164128A4 (en) * | 2014-07-03 | 2018-02-28 | Dr. Reddy's Laboratories Ltd. | Amorphous form of eliglustat hemitartarate |
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