WO2008147169A2 - Microemulsion containing pirfenidone - Google Patents
Microemulsion containing pirfenidone Download PDFInfo
- Publication number
- WO2008147169A2 WO2008147169A2 PCT/MX2008/000068 MX2008000068W WO2008147169A2 WO 2008147169 A2 WO2008147169 A2 WO 2008147169A2 MX 2008000068 W MX2008000068 W MX 2008000068W WO 2008147169 A2 WO2008147169 A2 WO 2008147169A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- composition
- weight
- unit dose
- pirfenidone
- soft gelatin
- 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.)
- Ceased
Links
Classifications
-
- 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
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4412—Non condensed pyridines; Hydrogenated derivatives thereof having oxo groups directly attached to the heterocyclic ring
-
- 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
- A61K9/0087—Galenical forms not covered by A61K9/02 - A61K9/7023
- A61K9/0095—Drinks; Beverages; Syrups; Compositions for reconstitution thereof, e.g. powders or tablets to be dispersed in a glass of water; Veterinary drenches
-
- 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
- A61K9/10—Dispersions; Emulsions
- A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
- A61K9/1075—Microemulsions or submicron emulsions; Preconcentrates or solids thereof; Micelles, e.g. made of phospholipids or block copolymers
Definitions
- the present invention relates to a formulation containing pirfenidone, which is prepared in a microemulsion that offers advantages over other oral administration pharmaceutical forms known in the state of the art, such as tablets, capsules, suspensions and solutions.
- Pirfenidone is itself a known compound and its pharmacological effects have been described in, for example, Japanese applications KOKAI Nos. 87677/1974 and 1284338/1976, as an anti ⁇ inflammatory agent that includes anti -Pyretic and analgesic, United States patents Nos. 3,839,346, published on October 1, 1974, 3,974,281, published on August 10, 1976, 4,042,699, published on August 16, 1977, and 4,052,509, published on October 4, 1911, describe methods for obtaining Pirfenidone, thus as its use as an anti ⁇ inflammatory agent.
- Mexican patent 182,266 describes the anti-fibrotic activity of 5-methyl-l-phenyl- (IH) -pyridone.
- Pirfenidone has demonstrated its effectiveness as an anti-fibrotic agent, in different pathologies and organs, as it has been shown in previous studies, where we have observed an effect on fibroblasts and collagen produced by them, both in experimental models and in clinical trials
- Soft gelatin capsules are used in the pharmaceutical, cosmetic, nutritional and veterinary industry. This diversity demonstrates the versatility of the soft gelatin capsule, the content within a soft gelatin capsule can be a liquid, semi-solid mixtures, non-aqueous solutions or suspensions, all this due to the water-soluble nature of the gelatin.
- Soft gelatin capsules are containers or unit packages, consisting of two soft gelatin films, which contain the active ingredient among them. The soft gelatin capsule can Prepare in various shapes and sizes depending on the design needs of the medication. The advantages offered by soft gelatin capsules over other oral administration pharmaceutical forms are:
- - can be used as a means of oral, rectal, vaginal and ophthalmic administration
- the accuracy of filling is 1 to 2.5% depending on the asset to be filled; - they have elegant, bright and striking appearance of the finished product;
- - can be manufactured in different colors and sizes, thus responding to the administration needs of the medicament or design, being able to be manufactured transparent or colorful, with solid colors, natural transparency, solid colors in combination of two tones, transparent in two tones, polished or matte finishes.
- microemulsions differ from the emulsions by the fact that the former spontaneously forms r whereby a minimum free energy state of a single phase corresponds to them.
- Emulsions require the addition of energy (mechanical and / or heat) for their formulation. It follows that the interfacial tension between the continuous and dispersed phases in the microemulsion is low.
- micro droplet emulsions also called mini emulsions
- Micro emulsions are always stable to these changes.
- the easiest way to differentiate between micro emulsions and emulsions with micro droplets is to use repeated cycles of freezing and heating in both systems.
- the micro emulsion will return to its original state of stability, - since its restoration is controlled by diffusion while the emulsion is separated into the original components that gave rise to it.
- Soft gelatin capsules are made from the following components: gelatin between 38% and 42% preferably between 39% and 40% and more preferably between 39.9 and 40% by weight of the composition, purified water between 38% and 42% preferably between 39% and 40% and more preferably between 39.9 and 40% by weight of the composition, glycerin between 18% and 22% preferably between 19% and 20% and more preferably between 19.5 and 20% in weight of the composition, at least one conservative between 0.15% and 0.20% preferably between 0.16% and 0.19% and more preferably between 17 and 18% by weight of the composition, titanium dioxide between 0.25% and 0.30% preferably between 0.27% and 0.29% and more preferably between 0.28 and 0.29% by weight of the composition and a dye ⁇ yellow color No. 10 FDC) between 0.0095% and 0.015% preferably between 0.0097 and 0.013% and more preferably between 0.0099 and 0.011% by weight of the composition .
- An example of bark composition of jelly is shown in table 1:
- a second composition can be prepared from the components shown in Table 2:
- compositions are shown by way of examples, but are not limited in any way to the scope of the description of the present invention.
- the microemulsifiable composition of Pirfenidone object of the present invention further comprises; alcohol absolute ethyl, dl-alpha tocophexol acetate, Pluracol E-400, Cremophor RH-40 and Amaranth Oil.
- pirfenidone is present in an amount between 8.58% and 10.38% by weight of the composition, absolute ethyl alcohol in an amount between 6.92% and 15.57%, di-alpha tocopherol acetate in an amount between 12.58% and 28.30%, pluracol E-400 in an amount between 9.43% and 21.23%, Cremophor RH-40 in an amount between 25.16% and 56.60% and Amaranth Oil in an amount between 6.29% and 14.15%.
- compositions are shown by way of examples but are not limited in any way to the scope of the description of the present invention.
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Dispersion Chemistry (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
MICROEMULSION CONTENIENDO PIRFENIDONA MICROEMULSION CONTAINING PYRFENIDONE
CAMPO DE LA INVENCIÓN.FIELD OF THE INVENTION
La presente invención se relaciona a una formulación que contiene pirfenidona, la cual es preparada en una microemulsión que ofrece ventajas sobre otras formas farmacéuticas de administración oral conocidas en el estado de la técnica, como son tabletas, cápsulas, suspensiones y soluciones.The present invention relates to a formulation containing pirfenidone, which is prepared in a microemulsion that offers advantages over other oral administration pharmaceutical forms known in the state of the art, such as tablets, capsules, suspensions and solutions.
ANTECEDENTES DE LA INVENCIÓN.BACKGROUND OF THE INVENTION
La 5-metil-l-fenil-(IH)-piridona, de fórmula;The 5-methyl-l-phenyl- (IH) -pyridone, of the formula;
es un fármaco que ha sido aplicado en la restauración de los tejidos con lesiones que cursan con fibrosis y para la prevención de lesiones fibróticas. Este compuesto, llamado Pirfenidona, es por si mismo un compuesto conocido y sus efectos farmacológicos han sido descritos en, por ejemplo, las solicitudes Japonesas KOKAI Nos. 87677/1974 y 1284338/1976, como un agente anti¬ inflamatorio que incluye los efectos anti-piréticos y analgésicos, las patentes de los Estados unidos Nos. 3,839,346, publicada el 1 de octubre de 1974, 3,974,281, publicada el 10 de agosto de 1976, 4,042,699, publicada el 16 de agosto de 1977, y 4,052,509, publicada el 4 de octubre de 1911, describen métodos para la obtención de Pirfenidona, asi como su uso como agente anti¬ inflamatorio. En la patente mexicana 182,266 se describe la actividad anti-fibrótica de la 5-metil-l-fenil- (IH) - piridona .It is a drug that has been applied in the restoration of tissues with lesions that occur with fibrosis and for the prevention of fibrotic lesions. This compound, called Pirfenidone, is itself a known compound and its pharmacological effects have been described in, for example, Japanese applications KOKAI Nos. 87677/1974 and 1284338/1976, as an anti ¬ inflammatory agent that includes anti -Pyretic and analgesic, United States patents Nos. 3,839,346, published on October 1, 1974, 3,974,281, published on August 10, 1976, 4,042,699, published on August 16, 1977, and 4,052,509, published on October 4, 1911, describe methods for obtaining Pirfenidone, thus as its use as an anti ¬ inflammatory agent. Mexican patent 182,266 describes the anti-fibrotic activity of 5-methyl-l-phenyl- (IH) -pyridone.
Se han empleado diferentes recursos y tratamientos sin que a la fecha ninguno de ellos se muestre realmente efectivo. La Pirfenidona ha demostrado su efectividad como agente anti-fibrótico, en diferentes patologías y órganos, tal como ha sido demostrado en trabajos previos, donde hemos observado un efecto sobre los fibroblastos y la colágena producida por los mismos, tanto en modelos experimentales, como en ensayos clínicos .Different resources and treatments have been used without any of them being really effective to date. Pirfenidone has demonstrated its effectiveness as an anti-fibrotic agent, in different pathologies and organs, as it has been shown in previous studies, where we have observed an effect on fibroblasts and collagen produced by them, both in experimental models and in clinical trials
Cápsulas de Gelatina Blanda.Soft gelatin capsules.
Las cápsulas de gelatina blanda son utilizadas en la industria farmacéutica, cosmética, nutricional y veterinaria. Esta diversidad demuestra la versatilidad de la cápsula de gelatina blanda, el contenido dentro de una cápsula de gelatina blanda puede ser un liquido, mezclas semisólidas, soluciones o suspensiones no acuosas, todo esto debido al carácter hidrosoluble de la gelatina. Las cápsulas de gelatina blandas son contenedores o paquetes unitarios, formadas por dos películas de gelatina blanda, que contienen entre ellas al ingrediente activo. La cápsula de gelatina blanda puede prepararse en formas y tamaños diversos dependiendo de las necesidades de diseño del medicamento. Las ventajas que ofrecen las cápsulas de gelatina blanda sobre otras formas farmacéuticas de administración oral, son:Soft gelatin capsules are used in the pharmaceutical, cosmetic, nutritional and veterinary industry. This diversity demonstrates the versatility of the soft gelatin capsule, the content within a soft gelatin capsule can be a liquid, semi-solid mixtures, non-aqueous solutions or suspensions, all this due to the water-soluble nature of the gelatin. Soft gelatin capsules are containers or unit packages, consisting of two soft gelatin films, which contain the active ingredient among them. The soft gelatin capsule can Prepare in various shapes and sizes depending on the design needs of the medication. The advantages offered by soft gelatin capsules over other oral administration pharmaceutical forms are:
- Dosificación unitaria, es decir, en una sola pieza; por su proceso de fabricación son compartimentos herméticamente sellados :- Unit dosage, that is, in one piece; Due to their manufacturing process they are hermetically sealed compartments:
- son fáciles de administrar; - permiten la diferenciación, del producto, a través de colores y formas;- they are easy to administer; - allow differentiation, of the product, through colors and shapes;
- se tiene uniformidad y precisión entre una dosis y otra;- there is uniformity and precision between one dose and another;
- son a prueba de adulteraciones, pues son selladas herméticamente de origen; - tienen mucho mejor estabilidad, que otros medios de administración oral;- they are proof of adulteration, since they are hermetically sealed of origin; - they have much better stability, than other means of oral administration;
- tienen alta biodisponibilidad y rápida absorción;- have high bioavailability and rapid absorption;
- cuentan con la preferencia del consumidor, debido a su seguridad, apariencia y asepsia; - ofrecen protección del activo contra la contaminación, la luz y la oxidación;- they have consumer preference, due to their safety, appearance and asepsis; - offer protection of the asset against pollution, light and oxidation;
- los olores y sabores desagradables se evitan al tomar los activos encapsulados de esta forma;- unpleasant odors and flavors are avoided by taking encapsulated assets in this way;
- son los medios de administración oral fácil de pasar por la garganta;- are the means of oral administration easy to pass through the throat;
- pueden ser utilizados como medio de administración oral, rectal, vaginal y oftálmica;- can be used as a means of oral, rectal, vaginal and ophthalmic administration;
- la exactitud de llenado es de 1 a 2.5% dependiendo del activo a llenar; - cuentan con apariencia elegante, brillante y llamativa del producto terminado;- the accuracy of filling is 1 to 2.5% depending on the asset to be filled; - they have elegant, bright and striking appearance of the finished product;
- pueden ser fabricadas en diversos colores y tamaños, respondiendo asi a las necesidades de administración del medicamento o de diseño, pudiendo ser fabricadas transparentes o coloridas, con colores sólidos, transparencia natural, colores sólidos en combinación de dos tonos, transparentes en dos tonos, abrillantados o acabados mate.- can be manufactured in different colors and sizes, thus responding to the administration needs of the medicament or design, being able to be manufactured transparent or colorful, with solid colors, natural transparency, solid colors in combination of two tones, transparent in two tones, polished or matte finishes.
MICROEMULSIONMICROEMULSION
Las microemulsiones se diferencian de las emulsiones por el hecho de que las primeras se forman espontáneamenter por lo cual les corresponde un estado de energía libre mínimo de una fase simple. Las emulsiones por el contrario requieren de Is adición de energía (mecánica y/o calor) para su formulación. De esto se desprende que la tensión interfacial entre las fases continua y dispersa en la microemulsión es baja. Cuando las emulsiones con micro gotículas {también llamadas mini emulsiones) son coaguladas por cambios de temperatura. Las micro emulsiones por el contrario siempre son estables a estos cambios. Así, la manera más sencilla de diferenciar entre micro emulsiones y emulsiones con micro gotículas es usar ciclos repetidos de congelamiento y calentamiento en ambos sistemas. La micro emulsión regresará a su estado original de estabilidad,- ya que su restauración esta controlada por difusión mientras que la emulsión se separa en los componentes originales que dieron lugar a la misma.The microemulsions differ from the emulsions by the fact that the former spontaneously forms r whereby a minimum free energy state of a single phase corresponds to them. Emulsions, on the other hand, require the addition of energy (mechanical and / or heat) for their formulation. It follows that the interfacial tension between the continuous and dispersed phases in the microemulsion is low. When micro droplet emulsions (also called mini emulsions) are coagulated by temperature changes. Micro emulsions on the other hand are always stable to these changes. Thus, the easiest way to differentiate between micro emulsions and emulsions with micro droplets is to use repeated cycles of freezing and heating in both systems. The micro emulsion will return to its original state of stability, - since its restoration is controlled by diffusion while the emulsion is separated into the original components that gave rise to it.
OBJETO DE LA INVENCIÓN Es objeto de la presente invención proporcionar una composición para su administración oral que comprende Pirfenidona. También, es objeto de la presente invención proporcionar una composición para la elaboración de una cápsula de gelatina blanda. Otro objeto de la presente invención es proporcionar una cápsula, de gelatina blanda que contenga una microemulsión cuyo principio activo es Pirfenidona. Entre otros objetos de la presente invención se encuentra el de proporcionar un medicamento en una cápsula de gelatina blanda para usarse como agente anti-fibrótico y anti-inflamatorio.OBJECT OF THE INVENTION It is an object of the present invention to provide a composition for oral administration comprising Pirfenidone. It is also the object of the present invention to provide a composition for the preparation of a soft gelatin capsule Another object of the present invention is to provide a soft gelatin capsule containing a microemulsion whose active ingredient is Pirfenidone. Among other objects of the present invention is that of providing a medicament in a soft gelatin capsule for use as an anti-fibrotic and anti-inflammatory agent.
ESPECIFICACIÓN DE LA INVENCIÓNSPECIFICATION OF THE INVENTION
COMPOSICIÓN DE LA CÁPSULACOMPOSITION OF THE CAPSULE
Las cápsulas de gelatina blanda se elabora a partir de los siguientes componentes: gelatina entre el 38% y 42% preferentemente entre 39% y 40% y con mayor preferencia entre 39.9 y 40% en peso de la composición, agua purificada entre el 38% y 42% preferentemente entre 39% y 40% y con mayor preferencia entre 39.9 y 40% en peso de la composición, glicerina entre el 18% y 22% preferentemente entre 19% y 20% y con mayor preferencia entre 19.5 y 20% en peso de la composición, al menos un conservador entre el 0.15% y 0.20% preferentemente entre 0.16% y 0.19% y con mayor preferencia entre 17 y 18% en peso de la composición, bióxido de titanio entre el 0.25% y 0.30% preferentemente entre 0.27% y 0.29% y con mayor preferencia entre 0.28 y 0.29% en peso de la composición y un colorante {color amarillo No. 10 FDC) entre el 0.0095% y 0.015% preferentemente entre 0.0097 y 0.013% y con mayor preferencia entre 0.0099 y 0.011% en peso de la composición.. Un ejemplo de composición de la corteza de gelatina se muestra en la tabla 1: Soft gelatin capsules are made from the following components: gelatin between 38% and 42% preferably between 39% and 40% and more preferably between 39.9 and 40% by weight of the composition, purified water between 38% and 42% preferably between 39% and 40% and more preferably between 39.9 and 40% by weight of the composition, glycerin between 18% and 22% preferably between 19% and 20% and more preferably between 19.5 and 20% in weight of the composition, at least one conservative between 0.15% and 0.20% preferably between 0.16% and 0.19% and more preferably between 17 and 18% by weight of the composition, titanium dioxide between 0.25% and 0.30% preferably between 0.27% and 0.29% and more preferably between 0.28 and 0.29% by weight of the composition and a dye {yellow color No. 10 FDC) between 0.0095% and 0.015% preferably between 0.0097 and 0.013% and more preferably between 0.0099 and 0.011% by weight of the composition .. An example of bark composition of jelly is shown in table 1:
Una segunda composición puede ser preparada a partir de los componentes gue se muestran en la Tabla 2:A second composition can be prepared from the components shown in Table 2:
Estas dos composiciones son mostradas a modo de ejemplos, más no son limitativos en grado alguno del alcance de la descripción de la presente invención.These two compositions are shown by way of examples, but are not limited in any way to the scope of the description of the present invention.
COMPOSICIÓN MICROEMDLSIONABLE DE PIRFENIDONAMICROEMDLSIONABLE COMPOSITION OF PYRFENIDONE
La composición microemulsionable de Pirfenidona objeto de la presente invención comprende además; alcohol etílico absoluto, acetato de dl-alfa tocofexol, Pluracol E-400, Cremophor RH-40 y Aceite de Amaranto. En donde el pirfenidone se encuentre presente en una cantidad entre el 8.58% y el 10.38 % en peso de la composición, el alcohol etílico absoluto en una cantidad entre el 6.92% y el 15.57%, el acetato de di-alfa tocoferol en una cantidad entre el 12.58% y el 28.30%, el pluracol E-400 en una cantidad entre el 9.43% y el 21.23%, el Cremophor RH-40 en una cantidad entre ei 25.16% y el 56.60% y el Aceite de amaranto en una cantidad entre el 6.29% y el 14.15%.The microemulsifiable composition of Pirfenidone object of the present invention further comprises; alcohol absolute ethyl, dl-alpha tocophexol acetate, Pluracol E-400, Cremophor RH-40 and Amaranth Oil. Where pirfenidone is present in an amount between 8.58% and 10.38% by weight of the composition, absolute ethyl alcohol in an amount between 6.92% and 15.57%, di-alpha tocopherol acetate in an amount between 12.58% and 28.30%, pluracol E-400 in an amount between 9.43% and 21.23%, Cremophor RH-40 in an amount between 25.16% and 56.60% and Amaranth Oil in an amount between 6.29% and 14.15%.
Un ejemplo de la composición microemulsionable de Pirfenidona se muestra a continuación:An example of the microemulsifiable composition of Pirfenidone is shown below:
Un segundo ejemplo para una composición microemulsionable de Pirfenidona se ejemplifica de la siguiente manera:A second example for a microemulsifiable composition of Pirfenidone is exemplified as follows:
Las composiciones son mostradas a modos de ejemplos más no son limitativos en grado alguno del alcance de la descripción de la presente invención. The compositions are shown by way of examples but are not limited in any way to the scope of the description of the present invention.
Claims
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| MXMX/A/2007/006348 | 2007-05-29 | ||
| MX2007006438 | 2007-05-29 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| WO2008147169A2 true WO2008147169A2 (en) | 2008-12-04 |
| WO2008147169A3 WO2008147169A3 (en) | 2009-01-22 |
| WO2008147169A8 WO2008147169A8 (en) | 2009-07-30 |
Family
ID=40075678
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/MX2008/000068 Ceased WO2008147169A2 (en) | 2007-05-29 | 2008-05-29 | Microemulsion containing pirfenidone |
Country Status (1)
| Country | Link |
|---|---|
| WO (1) | WO2008147169A2 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102846555A (en) * | 2012-04-09 | 2013-01-02 | 珠海亿邦制药股份有限公司 | Solid preparation comprising pirfenidone as active component and application thereof |
| US8969347B2 (en) | 2008-06-03 | 2015-03-03 | Intermune, Inc. | Compounds and methods for treating inflammatory and fibrotic disorders |
| US9675593B2 (en) | 2012-10-02 | 2017-06-13 | Intermune, Inc. | Anti-fibrotic pyridinones |
| US10233195B2 (en) | 2014-04-02 | 2019-03-19 | Intermune, Inc. | Anti-fibrotic pyridinones |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1113798B1 (en) * | 1998-09-18 | 2003-01-02 | Mepha AG | Topical formulation of alkyl-, phenyl-pyridone |
| CH696420A5 (en) * | 2002-09-13 | 2007-06-15 | Mepha Ag | New stable formulations of alkyl, phenyl-pyridones for topical use. |
| JP4542743B2 (en) * | 2002-12-26 | 2010-09-15 | Ｋｄｌ株式会社 | Solution pharmaceutical composition of pyridone derivatives |
| NZ591443A (en) * | 2005-09-22 | 2013-04-26 | Intermune Inc | Granule formation of pirfenidone and pharmaceutically acceptable excipients |
-
2008
- 2008-05-29 WO PCT/MX2008/000068 patent/WO2008147169A2/en not_active Ceased
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8969347B2 (en) | 2008-06-03 | 2015-03-03 | Intermune, Inc. | Compounds and methods for treating inflammatory and fibrotic disorders |
| US9290450B2 (en) | 2008-06-03 | 2016-03-22 | Intermune, Inc. | Compounds and methods for treating inflammatory and fibrotic disorders |
| USRE47142E1 (en) | 2008-06-03 | 2018-11-27 | Intermune, Inc. | Compounds and methods for treating inflammatory and fibrotic disorders |
| CN102846555A (en) * | 2012-04-09 | 2013-01-02 | 珠海亿邦制药股份有限公司 | Solid preparation comprising pirfenidone as active component and application thereof |
| US9675593B2 (en) | 2012-10-02 | 2017-06-13 | Intermune, Inc. | Anti-fibrotic pyridinones |
| US10376497B2 (en) | 2012-10-02 | 2019-08-13 | Intermune, Inc. | Anti-fibrotic pyridinones |
| US10898474B2 (en) | 2012-10-02 | 2021-01-26 | Intermune, Inc. | Anti-fibrotic pyridinones |
| US10233195B2 (en) | 2014-04-02 | 2019-03-19 | Intermune, Inc. | Anti-fibrotic pyridinones |
| US10544161B2 (en) | 2014-04-02 | 2020-01-28 | Intermune, Inc. | Anti-fibrotic pyridinones |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2008147169A3 (en) | 2009-01-22 |
| WO2008147169A8 (en) | 2009-07-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ES2592504T3 (en) | Controlled release preparations | |
| MXPA02003312A (en) | Compositions having improved stability. | |
| ES2383038T3 (en) | Foamable composition for oral care | |
| CN101795730B (en) | Controlled surface gelation of mucoadhesive polymers on the oral mucosa | |
| BRPI0708773A2 (en) | Method for solubilization, dispersion and stabilization of substances, products manufactured according to the method, and use thereof | |
| ES2880813T3 (en) | Pharmaceutical formulations of naproxen for soft gel encapsulation and combinations thereof | |
| AR017801A1 (en) | A COMPOSITION OF PRE-CONCENTRATED IN MICROEMULSION CONTAINING CYCLOSPORIN, AND A PHARMACEUTICAL FORMULATION THAT UNDERSTANDS | |
| CN105392473B (en) | Composition for external use producing foam state when used | |
| JP2018021002A (en) | Pharmaceutical preparation containing loxoprofen | |
| MXPA04011834A (en) | Oral care capsules. | |
| WO2008147169A2 (en) | Microemulsion containing pirfenidone | |
| JP2014214085A (en) | Olopatadine-containing aqueous composition | |
| CN1708301A (en) | Melatonin Daily Dosing Unit | |
| KR940021054A (en) | Capsule-type ubidecarenone oral preparation | |
| US20030091600A1 (en) | Process for making personal care compositions comprising titanium dioxide and personal care compositions made by the process | |
| JP2017137304A (en) | Pharmaceutical preparation containing loxoprofen | |
| ES2215101T3 (en) | PHARMACEUTICAL FORMULATIONS CONTAINING ANTI-INFLAMMATORY ACTIVE PRODUCTS, AND THEIR EMPLOYMENT. | |
| AU2021103957A4 (en) | A composition and application thereof | |
| US20140106002A1 (en) | Homeopathic composition and method for the treatment of skin irritations and other skin diseases | |
| BR102022018688A2 (en) | COSMETIC ARTICLE IN STICK FORM AND METHOD FOR PRODUCING IT | |
| CN103476398A (en) | Menthol liquids composition | |
| JP7629709B2 (en) | Oral Composition | |
| MX2007006348A (en) | Microemulsion containing pirfenidone. | |
| BR112017012809B1 (en) | COMPOSITION FOR ORAL HYGIENE AND USE OF A SOLUBLE ZINC POLYPHOSPHATE COMPLEX IN THE PREPARATION OF THE SAME | |
| ITMI20112221A1 (en) | STABLE FORMULATIONS IN JELLY CAPSULES SPRINGS OF PIASTRINICAL ANTI-AGGREGATES, OMEGA-3 FATTY ACIDS AND AMYLOSUS |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 08766683 Country of ref document: EP Kind code of ref document: A2 |
|
| DPE1 | Request for preliminary examination filed after expiration of 19th month from priority date (pct application filed from 20040101) | ||
| NENP | Non-entry into the national phase |
Ref country code: DE |
|
| 122 | Ep: pct application non-entry in european phase |
Ref document number: 08766683 Country of ref document: EP Kind code of ref document: A2 |