ES2765513A1 - COMPOSITION TO INCREASE THE SOLUBILITY OF COMPOUNDS (Machine-translation by Google Translate, not legally binding) - Google Patents
COMPOSITION TO INCREASE THE SOLUBILITY OF COMPOUNDS (Machine-translation by Google Translate, not legally binding) Download PDFInfo
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- ES2765513A1 ES2765513A1 ES201930415A ES201930415A ES2765513A1 ES 2765513 A1 ES2765513 A1 ES 2765513A1 ES 201930415 A ES201930415 A ES 201930415A ES 201930415 A ES201930415 A ES 201930415A ES 2765513 A1 ES2765513 A1 ES 2765513A1
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- cyclodextrin
- composition
- present
- solubility
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- 239000000203 mixture Substances 0.000 title claims abstract description 45
- 150000001875 compounds Chemical class 0.000 title description 4
- 229920000858 Cyclodextrin Polymers 0.000 claims abstract description 32
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000000034 method Methods 0.000 claims abstract description 10
- 235000010241 potassium sorbate Nutrition 0.000 claims abstract description 10
- 239000004302 potassium sorbate Substances 0.000 claims abstract description 10
- 229940069338 potassium sorbate Drugs 0.000 claims abstract description 10
- 235000010234 sodium benzoate Nutrition 0.000 claims abstract description 10
- 239000004299 sodium benzoate Substances 0.000 claims abstract description 10
- CHHHXKFHOYLYRE-UHFFFAOYSA-M 2,4-Hexadienoic acid, potassium salt (1:1), (2E,4E)- Chemical compound [K+].CC=CC=CC([O-])=O CHHHXKFHOYLYRE-UHFFFAOYSA-M 0.000 claims abstract description 8
- 239000000546 pharmaceutical excipient Substances 0.000 claims abstract description 8
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 claims abstract description 8
- 238000002360 preparation method Methods 0.000 claims abstract description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
- ZFMITUMMTDLWHR-UHFFFAOYSA-N Minoxidil Chemical compound NC1=[N+]([O-])C(N)=CC(N2CCCCC2)=N1 ZFMITUMMTDLWHR-UHFFFAOYSA-N 0.000 claims description 11
- JWJOTENAMICLJG-QWBYCMEYSA-N dutasteride Chemical compound O=C([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)N[C@@H]4CC3)C)CC[C@@]21C)NC1=CC(C(F)(F)F)=CC=C1C(F)(F)F JWJOTENAMICLJG-QWBYCMEYSA-N 0.000 claims description 11
- 229960004199 dutasteride Drugs 0.000 claims description 11
- 229960003632 minoxidil Drugs 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 239000002537 cosmetic Substances 0.000 claims description 5
- 239000002202 Polyethylene glycol Substances 0.000 claims description 4
- 229920001223 polyethylene glycol Polymers 0.000 claims description 4
- HFHDHCJBZVLPGP-RWMJIURBSA-N alpha-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO HFHDHCJBZVLPGP-RWMJIURBSA-N 0.000 claims description 2
- BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical compound [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 description 4
- 238000010587 phase diagram Methods 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 238000010668 complexation reaction Methods 0.000 description 2
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 229940097362 cyclodextrins Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000007614 solvation Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
Classifications
-
- 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
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
- A61K47/40—Cyclodextrins; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q7/00—Preparations for affecting hair growth
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Dermatology (AREA)
- Birds (AREA)
- Medicinal Preparation (AREA)
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
DESCRIPCIÓNDESCRIPTION
COMPOSICIÓN PARA AUMENTAR LA SOLUBILIDAD DE COMPUESTOSCOMPOSITION TO INCREASE THE SOLUBILITY OF COMPOUNDS
Campo de la invenciónField of the Invention
La presente invención se encuadra en el campo general de la galénica y en particular, se refiere a una composición para aumentar la solubilidad de compuestos activos.The present invention falls within the general field of galenics and in particular, relates to a composition for increasing the solubility of active compounds.
Estado de la técnicaState of the art
Existen diversos principios activos o moléculas que, debido a su composición química, presentan una baja solubilidad en medio acuoso, de tal forma que para que estas moléculas ejerzan su función en el target específico, necesitan ser mezcladas con excipientes que aumenten la solvatación. Una solución a este problema es utilizar excipientes hidroalcohólicos, sin embargo, si el principio activo en cuestión es para uso tópico, este excipiente puede provocar irritaciones o alergias.There are various active ingredients or molecules that, due to their chemical composition, have a low solubility in an aqueous medium, so that in order for these molecules to perform their function on the specific target, they need to be mixed with excipients that increase solvation. A solution to this problem is to use hydroalcoholic excipients, however, if the active ingredient in question is for topical use, this excipient can cause irritations or allergies.
Existe la necesidad de encontrar excipientes que aumenten la solubilidad de moléculas o principios activos, y que puedan ser utilizados de forma tópica sin que produzcan efectos secundarios en el usuario.There is a need to find excipients that increase the solubility of molecules or active ingredients, and that can be used topically without causing side effects in the user.
Breve descripción de la invenciónBrief description of the invention
La presente invención soluciona los problemas descritos en el estado de la técnica puesto que proporciona una composición que aumenta la solubilidad acuosa de distintos compuestos activos.The present invention solves the problems described in the state of the art since it provides a composition that increases the aqueous solubility of different active compounds.
Así pues, en un primer aspecto, la presente invención se refiere a una composición (de aquí en adelante composición de la presente invención) que comprende:Thus, in a first aspect, the present invention refers to a composition (hereinafter composition of the present invention) comprising:
- al menos una ciclodextrina,- at least one cyclodextrin,
- benzoato sódico, y- sodium benzoate, and
- sorbato potásico.- potassium sorbate.
En una realización particular, la composición de la presente invención comprende:In a particular embodiment, the composition of the present invention comprises:
- 0.1 - 6 % en peso de al menos una ciclodextrina,- 0.1 - 6% by weight of at least one cyclodextrin,
- 0.1 - 0.3 % en peso de benzoato sódico, y - 0.1 - 0.3% by weight sodium benzoate, and
- 0.1 - 0.3 % en peso de sorbato potásico- 0.1 - 0.3% by weight of potassium sorbate
En una realización particular, la ciclodextrina es seleccionada de entre a-ciclodextrina, pciclodextrina, Y-ciclodextrina y mezclas de las mismas. Preferentemente, la ciclodextrina es una hidroxipropil-ciclodextrina. Más preferentemente, la composición de la presente invención comprende hidroxipropil-p-ciclodextrina, e hidroxypropil-Y-ciclodextrina.In a particular embodiment, the cyclodextrin is selected from a-cyclodextrin, pccyclodextrin, Y-cyclodextrin, and mixtures thereof. Cyclodextrin is preferably a hydroxypropyl-cyclodextrin. More preferably, the composition of the present invention comprises hydroxypropyl-p-cyclodextrin, and hydroxypropyl-Y-cyclodextrin.
En una realización preferente, la composición de la presente invención comprende hidroxipropilp-ciclodextrina, e hidroxypropil-Y-ciclodextrina, benzoato sódico y sorbato potásico.In a preferred embodiment, the composition of the present invention comprises hydroxypropyl-cyclodextrin, and hydroxypropyl-Y-cyclodextrin, sodium benzoate, and potassium sorbate.
En otra realización particular, la composición de la presente invención comprende agua.In another particular embodiment, the composition of the present invention comprises water.
En otra realización particular, la composición de la presente invención comprende al menos un alcohol. Más en particular, el alcohol es seleccionado de entre etanol, polietilenglicol y mezclas de los mismos. Preferentemente, la composición de la presente invención comprende etanol y polietilenglicol.In another particular embodiment, the composition of the present invention comprises at least one alcohol. More particularly, alcohol is selected from ethanol, polyethylene glycol, and mixtures thereof. Preferably, the composition of the present invention comprises ethanol and polyethylene glycol.
En otra realización preferente, la composición de la presente invención comprende hidroxipropilp-ciclodextrina, e hidroxypropil-Y-ciclodextrina, benzoato sódico y sorbato potásico, etanol y polietilenglicol.In another preferred embodiment, the composition of the present invention comprises hydroxypropyl-cyclodextrin, and hydroxypropyl-Y-cyclodextrin, sodium benzoate and potassium sorbate, ethanol, and polyethylene glycol.
En otro aspecto, la presente invención se refiere a una composición cosmética (de aquí en adelante, composición cosmética de la presente invención) que comprende la composición de la presente invención junto con minoxidilo y/o dutasteride.In another aspect, the present invention relates to a cosmetic composition (hereinafter, cosmetic composition of the present invention) comprising the composition of the present invention together with minoxidil and / or dutasteride.
En otro aspecto, la presente invención se refiere al uso de la composición de la presente invención como excipiente. Más en particular, la presente invención se refiere al uso de la composición de la presente invención como excipiente para aumentar la solubilidad acuosa de principios activos.In another aspect, the present invention relates to the use of the composition of the present invention as an excipient. More particularly, the present invention relates to the use of the composition of the present invention as an excipient to increase the aqueous solubility of active ingredients.
En otro aspecto, la presente invención se refiere a un procedimiento para la preparación la composición de la presente invención (de aquí en adelante, procedimiento de la presente invención), que comprende las siguientes etapas:In another aspect, the present invention relates to a process for preparing the composition of the present invention (hereinafter, the process of the present invention), which comprises the following steps:
a) mezclar al menos una ciclodextrina con benzoato sódico y sorbato potásicoa) mix at least one cyclodextrin with sodium benzoate and potassium sorbate
b) disolver la mezcla obtenida en la etapa a) con aguab) dissolve the mixture obtained in step a) with water
En una realización particular, el procedimiento de la presente invención comprende una etapa adicional de adición de al menos un alcohol, más en particular, la etapa de adición de al menos un alcohol se da después de la etapa a), en otra realización particular, la etapa de adición de al menos un alcohol se da después de la etapa b).In a particular embodiment, the process of the present invention comprises an additional step of adding at least one alcohol, more in particular, the step of adding at least an alcohol is given after step a), in another particular embodiment, the step of adding at least one alcohol is given after step b).
En otro aspecto, la presente invención se refiere a un procedimiento para la preparación de la composición cosmética de la presente invención, que comprende el procedimiento de la presente invención y una etapa de adición de dutasteride y/o minoxidilo.In another aspect, the present invention relates to a process for the preparation of the cosmetic composition of the present invention, which comprises the process of the present invention and a step of adding dutasteride and / or minoxidil.
Descripción de las figurasDescription of the figures
Figura 1: muestra el diagrama de fases para dutasteride con Y-ciclodextrina.Figure 1: shows the phase diagram for dutasteride with Y-cyclodextrin.
Figura 2: muestra el diagrama de fases para dutasteride con hidroxypropil-Y-ciclodextrina.Figure 2: shows the phase diagram for dutasteride with hydroxypropyl-Y-cyclodextrin.
Figura 3: muestra el diagrama de fases para minoxidilo con p-ciclodextrina.Figure 3: shows the phase diagram for minoxidil with p-cyclodextrin.
Figura 4: muestra el diagrama de fases para minoxidilo con hidroxipropil-p-ciclodextrina.Figure 4: shows the phase diagram for minoxidil with hydroxypropyl-p-cyclodextrin.
Descripción detallada de la invenciónDetailed description of the invention
Todas las composiciones de la presente invención fueron preparadas de la misma forma, cambiando las cantidades de cada componente y siguiendo el siguiente procedimiento:All the compositions of the present invention were prepared in the same way, changing the amounts of each component and following the following procedure:
En primer lugar, se procedió con la mezcla de la cada hidroxipropil-ciclodextrina con el benzoato sódico y sorbato potásico. A continuación, se añadió el etanol y el propilenglicol y se disolvieron en agua, y se añadió el dutasteride, o el minoxidilo o ambos, dependiendo de la composición que se preparara y finalmente se añadió agua hasta alcanzar un 100% en peso.First, each hydroxypropyl-cyclodextrin was mixed with sodium benzoate and potassium sorbate. Next, ethanol and propylene glycol were added and dissolved in water, and dutasteride, or minoxidil, or both were added, depending on the composition that was prepared, and finally, water was added until reaching 100% by weight.
Agua hasta alcanzar el 100% en pesoWater up to 100% by weight
Se procedió a comprobar la complejación de lo dutasteride con la y-cidodextrina nativa y la hidroxipropil-y-cidodextrina y se comprobó que la solubilidad acuosa se incrementó en más de 300 veces. Por lo tanto, dutasteride tendrá más de 300 veces más de disponibilidad para penetrar en la célula, sin necesidad de utilizar una solución hidroalcohólica.The complexation of the dutasteride with the native y-cidodextrin and hydroxypropyl-y-cidodextrin was verified and it was found that the aqueous solubility was increased by more than 300 times. Therefore, dutasteride will have more than 300 times more availability to penetrate the cell, without the need to use a hydroalcoholic solution.
En un rango de y-ciclodextrina de 0-20 mM, el dutasteride se solubilizó hasta 0.08 mM (incremento solubilidad 42 veces) (figura 1)In a 0-20 mM y-cyclodextrin range, dutasteride solubilized to 0.08 mM (42-fold solubility increase) (Figure 1)
En un rango de hidroxipropil-y-ciclodextrina de 0-100 mM, el dutasteride se solubilizó hasta 0.6 mM (incremento solubilidad 317 veces) (Figura 2).In a hydroxypropyl-and-cyclodextrin range of 0-100 mM, dutasteride solubilized to 0.6 mM (317-fold increase in solubility) (Figure 2).
En el caso de minoxidilo, su complejación en ciclodextrinas permitió incrementar su solubilidad acuosa unas 10 veces. Por lo tanto, minoxidilo tuvo 10 veces más disponibilidad para penetrar en la célula, sin necesidad de utilizar una solución hidroalcohólica.In the case of minoxidil, its complexation in cyclodextrins allowed it to increase its aqueous solubility by about 10 times. Therefore, minoxidil had 10 times more availability to penetrate the cell, without using a hydroalcoholic solution.
En un rango de p-ciclodextrina de 0-13 mM, minoxidilo se solubilizó hasta 23 mM (incremento solubilidad 2 veces) (Figura 3).In a p-cyclodextrin range of 0-13 mM, minoxidil was solubilized up to 23 mM (2-fold solubility increase) (Figure 3).
En un rango de hidroxipropil-p-ciclodextrina de 0-100 mM, el minoxidilo se solubilizó hasta 110 mM (incremento solubilidad casi 10 veces) (Figura 4). In a hydroxypropyl-p-cyclodextrin range of 0-100 mM, minoxidil was solubilized to 110 mM (almost 10-fold increase in solubility) (Figure 4).
Claims (12)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES201930415A ES2765513A1 (en) | 2019-05-10 | 2019-05-10 | COMPOSITION TO INCREASE THE SOLUBILITY OF COMPOUNDS (Machine-translation by Google Translate, not legally binding) |
| PCT/ES2020/070343 WO2020229720A1 (en) | 2019-05-10 | 2020-05-26 | Composition for increasing the solubility of compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES201930415A ES2765513A1 (en) | 2019-05-10 | 2019-05-10 | COMPOSITION TO INCREASE THE SOLUBILITY OF COMPOUNDS (Machine-translation by Google Translate, not legally binding) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2765513A1 true ES2765513A1 (en) | 2020-06-09 |
Family
ID=70970048
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES201930415A Pending ES2765513A1 (en) | 2019-05-10 | 2019-05-10 | COMPOSITION TO INCREASE THE SOLUBILITY OF COMPOUNDS (Machine-translation by Google Translate, not legally binding) |
Country Status (2)
| Country | Link |
|---|---|
| ES (1) | ES2765513A1 (en) |
| WO (1) | WO2020229720A1 (en) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2138197T3 (en) * | 1994-03-22 | 2000-01-01 | Fabre Pierre Dermo Cosmetique | HAIR LOTION BASED ON MINOXIDIL. |
| US20110112125A1 (en) * | 2009-11-09 | 2011-05-12 | Tritech Biopharmaceuticals Co., Ltd. | Novel hair growth composition |
| US20130251644A1 (en) * | 2012-03-22 | 2013-09-26 | Precision Dermatology, Inc. | Cyclodextrin-Based Microemulsions, and Dermatological Uses Thereof |
| US20150025082A1 (en) * | 2013-07-19 | 2015-01-22 | Boehringer Ingelheim Vetmedica Gmbh | Preserved etherified cyclodextrin derivatives containing liquid aqueous pharmaceutical composition |
-
2019
- 2019-05-10 ES ES201930415A patent/ES2765513A1/en active Pending
-
2020
- 2020-05-26 WO PCT/ES2020/070343 patent/WO2020229720A1/en active Application Filing
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2138197T3 (en) * | 1994-03-22 | 2000-01-01 | Fabre Pierre Dermo Cosmetique | HAIR LOTION BASED ON MINOXIDIL. |
| US20110112125A1 (en) * | 2009-11-09 | 2011-05-12 | Tritech Biopharmaceuticals Co., Ltd. | Novel hair growth composition |
| US20130251644A1 (en) * | 2012-03-22 | 2013-09-26 | Precision Dermatology, Inc. | Cyclodextrin-Based Microemulsions, and Dermatological Uses Thereof |
| US20150025082A1 (en) * | 2013-07-19 | 2015-01-22 | Boehringer Ingelheim Vetmedica Gmbh | Preserved etherified cyclodextrin derivatives containing liquid aqueous pharmaceutical composition |
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| Publication number | Publication date |
|---|---|
| WO2020229720A1 (en) | 2020-11-19 |
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