ES2646816T3 - Composiciones de dosificaciones orales de liberación retardada que contienen CDDO-Me amorfo - Google Patents
Composiciones de dosificaciones orales de liberación retardada que contienen CDDO-Me amorfo Download PDFInfo
- Publication number
- ES2646816T3 ES2646816T3 ES10704298.8T ES10704298T ES2646816T3 ES 2646816 T3 ES2646816 T3 ES 2646816T3 ES 10704298 T ES10704298 T ES 10704298T ES 2646816 T3 ES2646816 T3 ES 2646816T3
- Authority
- ES
- Spain
- Prior art keywords
- delayed
- compositions
- hpmc
- release oral
- containing amorphous
- 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.)
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- WPTTVJLTNAWYAO-KPOXMGGZSA-N Bardoxolone methyl Chemical compound C([C@@]12C)=C(C#N)C(=O)C(C)(C)[C@@H]1CC[C@]1(C)C2=CC(=O)[C@@H]2[C@@H]3CC(C)(C)CC[C@]3(C(=O)OC)CC[C@]21C WPTTVJLTNAWYAO-KPOXMGGZSA-N 0.000 title abstract description 9
- 239000000203 mixture Substances 0.000 title description 9
- 230000003111 delayed effect Effects 0.000 title 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 abstract description 14
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 abstract description 14
- 239000000546 pharmaceutical excipient Substances 0.000 abstract description 3
- 239000002245 particle Substances 0.000 abstract 2
- 238000007496 glass forming Methods 0.000 abstract 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 abstract 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 abstract 1
- 239000007909 solid dosage form Substances 0.000 abstract 1
- 238000009472 formulation Methods 0.000 description 7
- 239000002775 capsule Substances 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 101000945318 Homo sapiens Calponin-1 Proteins 0.000 description 2
- 101000652736 Homo sapiens Transgelin Proteins 0.000 description 2
- 102100031013 Transgelin Human genes 0.000 description 2
- 239000008186 active pharmaceutical agent Substances 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- JJAHTWIKCUJRDK-UHFFFAOYSA-N succinimidyl 4-(N-maleimidomethyl)cyclohexane-1-carboxylate Chemical compound C1CC(CN2C(C=CC2=O)=O)CCC1C(=O)ON1C(=O)CCC1=O JJAHTWIKCUJRDK-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-UHFFFAOYSA-N 2-(hydroxymethyl)-6-[4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxane-3,4,5-triol Chemical compound OCC1OC(OC2C(O)C(O)C(O)OC2CO)C(O)C(O)C1O GUBGYTABKSRVRQ-UHFFFAOYSA-N 0.000 description 1
- WSVLPVUVIUVCRA-KPKNDVKVSA-N Alpha-lactose monohydrate Chemical compound O.O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O WSVLPVUVIUVCRA-KPKNDVKVSA-N 0.000 description 1
- TXGZJQLMVSIZEI-UQMAOPSPSA-N Bardoxolone Chemical compound C1=C(C#N)C(=O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CCC(C)(C)C[C@H]5[C@H]4C(=O)C=C3[C@]21C TXGZJQLMVSIZEI-UQMAOPSPSA-N 0.000 description 1
- 241000282567 Macaca fascicularis Species 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 229950002483 bardoxolone Drugs 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 238000010241 blood sampling Methods 0.000 description 1
- 229940075614 colloidal silicon dioxide Drugs 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229920001531 copovidone Polymers 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000005414 inactive ingredient Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 229960001021 lactose monohydrate Drugs 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 210000002381 plasma Anatomy 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
Classifications
-
- 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
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
-
- 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
- A61K31/275—Nitriles; Isonitriles
- A61K31/277—Nitriles; Isonitriles having a ring, e.g. verapamil
-
- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
-
- 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
- A61K47/38—Cellulose; Derivatives thereof
-
- 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
- A61K47/50—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
-
- 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
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
-
- 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
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1629—Organic macromolecular compounds
- A61K9/1635—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
-
- 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
- A61K9/20—Pills, tablets, discs, rods
-
- 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
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/4841—Filling excipients; Inactive ingredients
- A61K9/4866—Organic macromolecular compounds
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
- C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Inorganic Chemistry (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Una forma de dosificación sólida que comprende partículas (A) que consisten en bardoxolona-metilo amorfo y un excipiente formador de vidrio mezclado con partículas (B) que consisten en hidroxipropilmetilcelulosa.
Description
corregido por la fracción de fármaco absorbido y calculado a partir de la fase terminal; TI/2, semivida farmacológica estimada del fármaco, AUC0-h, es el área estimada del fármaco bajo la curva desde el tiempo cero hasta 72 horas del muestreo sanguíneo; % de F, porcentaje de fármaco absorbido en relación con la administración intravenosa.
La Figura 1 muestra que el uso de HPMC en una SDD que contiene bardoxolona-metilo de la Forma B (denominada
5 "RTA 402") altera el perfil farmacocinético in vivo del fármaco. Por ejemplo, el incremento de las concentraciones de HPMC disminuye la concentración sanguínea media de RTA 402 alcanzada a partir de una dosis determinada. Por tanto, una concentración de HPMC de 20% peso/peso disminuyó la Cmax en >50%, en comparación con un control.
Sobre la base del rendimiento de la formulación de HPMC al 5%, descrita anteriormente, se llevaron a cabo estudios de disolución in vitro con formulaciones de la Forma B con 2,5%, 5,0%, o 7,5% de HPMC, como se muestra en la
10 tabla a continuación. Los resultados de estos estudios sugirieron que mayores porcentajes de HPMC se asociaron con velocidades más lentas de disolución.
- Componentes
- HPMC 2,5 HPMC 5,0 HPMC 7,5
- SDD de bardoxolona-metilo
- 12,50% 12,50% 12,50%
- Celulosa microcristalina
- 30,00% 30,00% 30,00%
- Monohidrato de lactosa
- 50,00% 47,50% 45,00%
- Copovidona XL
- 0,00% 0,00% 0,00%
- Laurilsulfato sódico
- 3,00% 3,00% 3,00%
- Dióxido de silicio coloidal
- 1,00% 1,00% 1,00%
- Estearato magnésico
- 1,00% 1,00% 1,00%
- HPMC
- 2,5% 5,00% 7,50%
- Total
- 100,00% 100,00% 100,00%
A la vista de estos resultados, las formulaciones de HPMC al 5,0% y 7,5% se seleccionaron para estudios farmacocinéticos comparativos en monos cynomolgus, con un control en forma de formulación de bardoxolona de la
15 Forma A, micronizada, cristalina, descrita en la Tabla 2. Cada una de las formulaciones de HPMC/Forma B se administró en cápsulas, mediante sonda oral, en dosis de 30 mg ó 10 mg. La formulación de control de la Forma A se administró a una dosis de 100 mg. En la Figura 2 se muestran los resultados (concentración en plasma sanguíneo de RTA 402 frente al tiempo).
También se preparó una formulación de HPMC que contenía bardoxolona-metilo de la Forma B para estudios
20 clínicos humanos. Se formularon cápsulas de bardoxolona-metilo con 15 mg de concentración. La Tabla 4 representa los componentes usados por cápsula. La Tabla 5 presenta la composición en porcentajes.
Como se ha descrito anteriormente, la SDD contenía 40% de ingrediente farmacéutico activo (API) de bardoxolonametilo. Como resultado, el uso de 37,5 mg de SDD por cápsula dio por resultado 15 mg de bardoxolona-metilo por cápsula.
25 En las Tablas 4 y 5, "SMCC" denota celulosa microcristalina silicificada, un excipiente co-procesado constituido por excipientes farmacopeicos. SMCC figura en la Guía de Ingredientes Inactivos de la FDA.
7
Claims (1)
-
imagen1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US15260809P | 2009-02-13 | 2009-02-13 | |
| US152608P | 2009-02-13 | ||
| PCT/US2010/024127 WO2010093944A2 (en) | 2009-02-13 | 2010-02-12 | Delayed release, oral dosage compositions that contain amorphous cddo-me |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2646816T3 true ES2646816T3 (es) | 2017-12-18 |
Family
ID=42335073
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES10704298.8T Active ES2646816T3 (es) | 2009-02-13 | 2010-02-12 | Composiciones de dosificaciones orales de liberación retardada que contienen CDDO-Me amorfo |
| ES17181174T Active ES2731601T3 (es) | 2009-02-13 | 2010-02-12 | Composiciones de dosificación oral de liberación retardada que contienen CDDO-Me amorfo |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES17181174T Active ES2731601T3 (es) | 2009-02-13 | 2010-02-12 | Composiciones de dosificación oral de liberación retardada que contienen CDDO-Me amorfo |
Country Status (30)
| Country | Link |
|---|---|
| US (2) | US8747901B2 (es) |
| EP (2) | EP2395979B1 (es) |
| JP (1) | JP5775464B2 (es) |
| KR (2) | KR20140016441A (es) |
| CN (2) | CN102387789A (es) |
| AU (1) | AU2010213594B2 (es) |
| BR (1) | BRPI1008023B8 (es) |
| CA (1) | CA2752048C (es) |
| CO (1) | CO6361904A2 (es) |
| CY (2) | CY1119595T1 (es) |
| DK (2) | DK2395979T3 (es) |
| EA (1) | EA023652B1 (es) |
| ES (2) | ES2646816T3 (es) |
| HK (1) | HK1220130A1 (es) |
| HR (2) | HRP20171639T1 (es) |
| HU (2) | HUE044005T2 (es) |
| IL (1) | IL214258A (es) |
| LT (2) | LT2395979T (es) |
| MX (1) | MX2011008344A (es) |
| MY (1) | MY173715A (es) |
| NO (1) | NO2395979T3 (es) |
| NZ (1) | NZ594488A (es) |
| PL (2) | PL2395979T3 (es) |
| PT (2) | PT3254675T (es) |
| SG (1) | SG173601A1 (es) |
| SI (2) | SI2395979T1 (es) |
| SM (2) | SMT201700527T1 (es) |
| TR (1) | TR201909743T4 (es) |
| WO (1) | WO2010093944A2 (es) |
| ZA (1) | ZA201105630B (es) |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6326507B1 (en) | 1998-06-19 | 2001-12-04 | Trustees Of Dartmouth College | Therapeutic compounds and methods of use |
| LT2252283T (lt) | 2008-01-11 | 2019-03-25 | Reata Pharmaceuticals, Inc. | Sintetiniai triterpenoidai ir jų panaudojimo būdai gydant ligą |
| KR101735807B1 (ko) | 2008-04-18 | 2017-05-15 | 리타 파마슈티컬스 잉크. | Ｃ-17에 아미노 및 기타 변형을 갖는 올레아놀산 유도체를 포함하는 항산화 염증 조절제 |
| CA2721665C (en) | 2008-04-18 | 2017-01-24 | Reata Pharmaceuticals, Inc. | Compounds including an anti-inflammatory pharmacore and methods of use |
| WO2009129545A1 (en) | 2008-04-18 | 2009-10-22 | Reata Pharmaceuticals, Inc. | Antioxidant inflammation modulators: oleanolic acid derivatives with saturation in the c-ring |
| HUE033288T2 (en) | 2008-04-18 | 2017-11-28 | Reata Pharmaceuticals Inc | Antioxidant inflammation modulators: C-17 homologated oleic acid derivatives |
| AU2009274037B2 (en) | 2008-07-22 | 2015-07-09 | Trustees Of Dartmouth College | Monocyclic cyanoenones and methods of use thereof |
| ES2646816T3 (es) | 2009-02-13 | 2017-12-18 | Reata Pharmaceuticals, Inc. | Composiciones de dosificaciones orales de liberación retardada que contienen CDDO-Me amorfo |
| MY163031A (en) | 2010-04-12 | 2017-07-31 | Reata Pharmaceuticals Inc | Method of treating obesity using antioxidant inflammation modulators |
| HUE038046T2 (hu) | 2010-12-17 | 2018-09-28 | Reata Pharmaceuticals Inc | Antioxidáns gyulladáscsökkentõ pirazolil és pirimidinil triciklusos enonok |
| CN103619866B (zh) | 2011-03-11 | 2016-06-22 | 里亚塔医药公司 | C4-一甲基三萜系化合物的衍生物及其使用方法 |
| CN103156861B (zh) * | 2011-12-08 | 2015-11-25 | 陈丽梅 | 齐敦果酸衍生物及其可药用盐在治疗糖尿病眼病中的应用 |
| US20130158077A1 (en) | 2011-12-19 | 2013-06-20 | Ares Trading S.A. | Pharmaceutical compositions |
| US9504679B2 (en) | 2011-12-19 | 2016-11-29 | Bjoern Colin Kahrs | Pharmaceutical compositions comprising glitazones and Nrf2 activators |
| ME02926B (me) | 2012-04-27 | 2018-04-20 | Reata Pharmaceuticals Inc | 2,2-difluoropropionamidni derivati bardoksolon metila, polimorfni oblici i postupci za njihovu upotrebu |
| US8981144B2 (en) | 2012-05-08 | 2015-03-17 | Trustees Of Dartmouth College | Method for synthesizing 2-cyano-3,12-dioxoolean-1, 9(11)-dien-28-oic acid methyl ester and derivatives thereof |
| US8921419B2 (en) | 2012-05-08 | 2014-12-30 | Trustees Of Dartmouth College | Triterpenoids and compositions containing the same |
| US9556222B2 (en) | 2012-06-15 | 2017-01-31 | Reata Pharmaceuticals, Inc. | A-ring epoxidized triterpenoid-based anti-inflammation modulators and methods of use thereof |
| US9512094B2 (en) | 2012-09-10 | 2016-12-06 | Reata Pharmaceuticals, Inc. | C17-heteroaryl derivatives of oleanolic acid and methods of use thereof |
| US9278912B2 (en) | 2012-09-10 | 2016-03-08 | Reata Pharmaceuticals, Inc. | C13-hydroxy derivatives of oleanolic acid and methods of use thereof |
| CR20150117A (es) | 2012-09-10 | 2016-10-10 | Reata Pharmaceuticals Inc | Derivados c17-alcandilo y alquendilo del ácido oleanólico y sus métodos de uso |
| UY39092A (es) | 2013-04-24 | 2021-03-26 | Abbvie Inc | Derivados de 2,2-difluoropropanamida y metil bardoxolona, formas polimórficas y métodos de uso |
| US20150080465A1 (en) | 2013-08-23 | 2015-03-19 | Reata Pharmaceuticals, Inc. | Methods of treating and preventing endothelial dysfunction using bardoxolone methyl or analogs thereof |
| WO2016070063A1 (en) | 2014-10-31 | 2016-05-06 | The Regents Of The University Of California | Compositions and methods for treating hiv-associated cognitive dysfunction |
| US11059792B2 (en) | 2015-02-12 | 2021-07-13 | Reata Pharmaceuticals, Inc. | Imidazolyl tricyclic enones as antioxidant inflammation modulators |
| EA201890767A1 (ru) | 2015-09-23 | 2019-09-30 | Рита Фармасьютикалз, Инк. | C4-модифицированные производные олеаноловой кислоты для ингибирования il-17 и других применений |
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| TWI831738B (zh) | 2016-12-16 | 2024-02-11 | 美商瑞塔醫藥有限責任公司 | 用於抑制ＲＯＲγ及其他用途的嘧啶三環烯酮衍生物 |
| WO2019014412A1 (en) | 2017-07-13 | 2019-01-17 | Pliva Hrvatska D.O.O. | NOVEL CRYSTALLINE POLYMORPHIC FORMS OF METHYL BARDOXOLONE |
| JP7244536B2 (ja) | 2018-04-06 | 2023-03-22 | キャプシュゲル・ベルジウム・エヌ・ヴィ | メタクリル酸メチル－メタクリル酸コポリマーからなる低アスペクト比の粒子のための噴霧乾燥方法 |
| BR112020025605A2 (pt) | 2018-06-15 | 2021-03-23 | Reata Pharmaceuticals, Inc. | compostos de pirazol e imidazol para inibição de il-17 e rorgama |
| EP3810141A1 (en) | 2018-06-20 | 2021-04-28 | Reata Pharmaceuticals, Inc. | Cysteine-dependent inverse agonists of nuclear receptors ror-gamma/ror-gamma-t and methods of treating diseases or disorders therewith |
| KR20210096162A (ko) | 2018-11-27 | 2021-08-04 | 쿄와 기린 가부시키가이샤 | 의약 조성물 |
| KR102891865B1 (ko) | 2019-07-19 | 2025-11-26 | 리아타 파마슈티컬즈, 아이엔씨. | C17 극성-치환된 헤테로방향족 합성 트리터페노이드 및 그의 사용 방법 |
| CN115803059A (zh) | 2020-05-09 | 2023-03-14 | 里亚塔医药控股有限责任公司 | 使用甲基巴多索隆或其类似物治疗covid-19的方法 |
| WO2022126129A1 (en) | 2020-12-11 | 2022-06-16 | Reata Pharmaceuticals, Inc. | Synthetic triterpenoids for use in therapy |
| CN114558019A (zh) * | 2022-03-26 | 2022-05-31 | 中国科学院昆明动物研究所 | 一种Rab13基因抑制剂及应用 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6326507B1 (en) | 1998-06-19 | 2001-12-04 | Trustees Of Dartmouth College | Therapeutic compounds and methods of use |
| US7435755B2 (en) * | 2000-11-28 | 2008-10-14 | The Trustees Of Dartmouth College | CDDO-compounds and combination therapies thereof |
| JP2008110962A (ja) * | 2006-08-02 | 2008-05-15 | Santen Pharmaceut Co Ltd | Ｎｒｆ２活性化物質を有効成分として含む角結膜障害の予防または治療剤 |
| JP4315182B2 (ja) * | 2006-10-30 | 2009-08-19 | ミツミ電機株式会社 | カメラモジュール |
| JP2008247898A (ja) * | 2007-03-08 | 2008-10-16 | Santen Pharmaceut Co Ltd | トリテルペノイドを有効成分として含有する酸化ストレスが関連する眼疾患の予防又は治療剤 |
| US8088824B2 (en) * | 2007-08-15 | 2012-01-03 | Reata Pharmaceuticals Inc. | Forms of CDDO methyl ester |
| LT2252283T (lt) | 2008-01-11 | 2019-03-25 | Reata Pharmaceuticals, Inc. | Sintetiniai triterpenoidai ir jų panaudojimo būdai gydant ligą |
| ES2646816T3 (es) | 2009-02-13 | 2017-12-18 | Reata Pharmaceuticals, Inc. | Composiciones de dosificaciones orales de liberación retardada que contienen CDDO-Me amorfo |
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