WO2019138346A1 - Composition pharmaceutique d'osimertinib - Google Patents
Composition pharmaceutique d'osimertinib Download PDFInfo
- Publication number
- WO2019138346A1 WO2019138346A1 PCT/IB2019/050176 IB2019050176W WO2019138346A1 WO 2019138346 A1 WO2019138346 A1 WO 2019138346A1 IB 2019050176 W IB2019050176 W IB 2019050176W WO 2019138346 A1 WO2019138346 A1 WO 2019138346A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- pharmaceutical composition
- pharmaceutical
- osimertinib
- diluent
- composition
- Prior art date
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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
-
- 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
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2009—Inorganic compounds
-
- 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
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2013—Organic compounds, e.g. phospholipids, fats
- A61K9/2018—Sugars, or sugar alcohols, e.g. lactose, mannitol; Derivatives thereof, e.g. polysorbates
-
- 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
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/2027—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
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
- A61K9/2054—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
-
- 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
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
- A61K9/2059—Starch, including chemically or physically modified derivatives; Amylose; Amylopectin; Dextrin
-
- 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
- A61K9/2072—Pills, tablets, discs, rods characterised by shape, structure or size; Tablets with holes, special break lines or identification marks; Partially coated tablets; Disintegrating flat shaped forms
- A61K9/2077—Tablets comprising drug-containing microparticles in a substantial amount of supporting matrix; Multiparticulate tablets
Definitions
- the present invention relates to a pharmaceutical composition
- a pharmaceutical composition comprising osimertinib or a pharmaceutically acceptable salt thereof and at least one diluent.
- the process to prepare such a pharmaceutical composition is also disclosed.
- Osimertinib (AZD9291) is a third-generation epidermal growth factor receptor (EGFR) tyrosine kinase inhibitor (TKI). It is developed by AstraZeneca for mutated EGFR cancers.
- Osimertinib mesylate is also known by the chemical name: N-(2- ⁇ 2-dimethylaminoethyl-methylamino ⁇ -4-methoxy-5- ⁇ [4-(l- methylindol-3-yl) pyrimidin-2-yl] amino ⁇ phenyl) prop-2-enamide mesylate salt and is reported to have the following chemical structure:
- Osimertinib mesylate in the form of 40 mg and 80 mg film coated tablet is approved in US under the brand name Tagrisso ® .
- Tagrisso ® is administered orally, once daily, with or without food for the treatment of patients with metastatic epidermal growth factor receptor (EGFR) T790M mutation-positive non-small cell lung cancer (NSCLC), as detected by an FDA-approved test, whose disease has progressed on or after EGFR TKI therapy.
- EGFR epidermal growth factor receptor
- NSCLC non-small cell lung cancer
- Osimertinib mesylate exhibits high solubility and higher than moderate permeability. It is highly soluble in stomach and upper gastrointestinal tract; moreover it has high solubility over a wide pH range.
- United States Patent No 8,946,235 discloses osimertinib and its mesylate salt. It further discloses pharmaceutical composition of osimertinib or its pharmaceutically acceptable salt thereof with pharmaceutically acceptable carrier. It also discloses method of treating non-small cell lung cancer in a warm blooded animal by administering to osimertinib mesylate. It further discloses polymorphic form A and form B of osimertinib mesylate.
- US20160324854 discloses an oral pharmaceutical composition of osimertinib mesylate, wherein, osimertinib mesylate is present in an amount from 2 to 70 parts by weight, two or more pharmaceutical diluents in an amount from 5 to 96 parts by weight, wherein one of the two diluent is microcrystalline cellulose (MCC) in an amount from 7 to 30 weight% of the two diluents.
- MMC microcrystalline cellulose
- US’ 854 publication discloses pharmaceutical compositions containing at least two diluents including microcrystalline cellulose as one of the diluent. There is a need in the art for alternative pharmaceutical compositions.
- the present invention relates to a solid oral pharmaceutical composition
- a solid oral pharmaceutical composition comprising osimertinib mesylate as an active ingredient and at least one diluent.
- the composition may further comprise other pharmaceutically acceptable excipients.
- the present invention relates to a solid oral pharmaceutical composition
- a solid oral pharmaceutical composition comprising osimertinib mesylate as an active ingredient and at least two diluents, wherein in none of the two diluent is microcrystalline cellulose or wherein one of the two diluent is microcrystalline cellulose in an amount greater than 30 % by weight of two or more diluents.
- the present invention relates to a solid oral pharmaceutical composition
- a solid oral pharmaceutical composition comprising osimertinib mesylate as an active ingredient and at least two diluents, wherein one of the two diluent is microcrystalline cellulose in an amount greater than 30% by weight of two or more diluents.
- the object of the present invention is to provide a pharmaceutical composition comprising osimertinib or a pharmaceutically acceptable thereof and at least one diluent.
- An aspect of the present invention provides a pharmaceutical composition comprising,
- An aspect of the present invention provides a pharmaceutical composition comprising,
- Another aspect of the present invention provides a pharmaceutical composition
- a pharmaceutical composition comprising,
- Another aspect of the present invention provides a pharmaceutical composition
- a pharmaceutical composition comprising,
- Another aspect of the present invention provides a pharmaceutical composition
- a pharmaceutical composition comprising,
- Another aspect of the present invention provides a pharmaceutical composition
- a pharmaceutical composition comprising,
- Another aspect of the present invention provides a pharmaceutical composition
- a pharmaceutical composition comprising,
- Another aspect of the present invention provides a pharmaceutical composition
- a pharmaceutical composition comprising,
- Another aspect of the present invention provides a pharmaceutical composition
- a pharmaceutical composition comprising
- composition comprising
- the present invention relates to a solid oral pharmaceutical composition
- a solid oral pharmaceutical composition comprising osimertinib mesylate as an active ingredient, at least one diluent, and other pharmaceutically acceptable excipients.
- present invention relates to a solid oral pharmaceutical composition
- a solid oral pharmaceutical composition comprising osimertinib mesylate as an active ingredient and one diluent, wherein the one diluent is microcrystalline cellulose or one diluent is other than microcrystalline cellulose, which can be selected from, but not limited to, mannitol, lactose, dicalcium phosphate and pregelatinized starch.
- present invention relates to a solid oral pharmaceutical composition
- a solid oral pharmaceutical composition comprising osimertinib mesylate as an active ingredient and at least two diluent, wherein optionally one diluent is microcrystalline cellulose in an amount greater than 30% by weight of two or more diluents, or none of the two diluents is microcrystalline cellulose and the diluents can be selected from, but not limited to, mannitol, lactose, dicalcium phosphate and pregelatinized starch.
- pharmaceutical composition may comprise osimertinib in the‘free base form’ or as a pharmaceutically acceptable salt, or as any mixture thereof.
- osimertinib present in pharmaceutical composition is in free base form.
- osimertinib present in pharmaceutical composition is in the form of acceptable salt of osimertinib.
- osimertinib present in pharmaceutical composition is in the form of mesylate salt of osimertinib.
- osimertinib mesylate is in crystalline form.
- the osimertinib mesylate crystalline form is polymorphic Form B (wherein polymorphic Form B of the mesylate salt of osimertinib may be defined in any of the ways described in international patent application number PCT/GB2012/05 l783/publication number WO2013/014448).
- the osimertinib mesylate crystalline form is Form A of the mesylate salt of osimertinib (wherein polymorphic Form A of the mesylate salt of osimertinib may be defined in any of the ways described in international patent application number PCT/GB20l2/05l783/publication number WO2013/014448).
- D90 of osimertinib mesylate is from about 5 mih to about 25 mih or from about 25 mih to about 45 mih or from about 45 mih to about 100 mih.
- An aspect of the present invention provides a pharmaceutical composition comprising,
- An aspect of the present invention provides a pharmaceutical composition comprising,
- Suitable diluent can be selected form the group of, but not limited to sugar and sugar alcohol such as mannitol, lactose, fructose, isomalt, lactitol, maltitol, sorbitol, erythritol, erythritol, maltose, polydextrose, sucrose, trehalose and xylitol; calcium carbonate; dicalcium phosphate; pregelatinized starch; calcium sulfate; cellulose acetate; ethylcellulose; inulin; magnesium carbonate; magnesium oxide; maltodextrin; sodium bicarbonate; sodium carbonate; sodium chloride and microcrystalline cellulose.
- sugar and sugar alcohol such as mannitol, lactose, fructose, isomalt, lactitol, maltitol, sorbitol, erythritol, erythritol, maltose, polydextrose, sucrose
- Another aspect of the present invention provides a pharmaceutical composition
- a pharmaceutical composition comprising
- Another aspect of the present invention provides a pharmaceutical composition
- a pharmaceutical composition comprising
- Another aspect of the present invention provides a pharmaceutical composition
- a pharmaceutical composition comprising
- Another aspect of the present invention provides a pharmaceutical composition
- a pharmaceutical composition comprising
- the only one diluent which is other than microcrystalline cellulose can be selected from sugar and sugar alcohol such as mannitol, lactose, fructose, isomalt, lactitol, maltitol, sorbitol, erythritol, erythritol, maltose, polydextrose, sucrose, trehalose and xylitol; calcium carbonate; dicalcium phosphate; pregelatinized starch; calcium sulfate; cellulose acetate; ethylcellulose; inulin; magnesium carbonate; magnesium oxide; maltodextrin; sodium bicarbonate; sodium carbonate; sodium chloride.
- sugar and sugar alcohol such as mannitol, lactose, fructose, isomalt, lactitol, maltitol, sorbitol, erythritol, erythritol, maltose, polydextrose, sucrose, treha
- Another aspect of the present invention provides a pharmaceutical composition
- a pharmaceutical composition comprising
- Another aspect of the present invention provides a pharmaceutical composition
- a pharmaceutical composition comprising
- the two diluents can be selected from sugar and sugar alcohol such as mannitol, lactose, fructose, isomalt, lactitol, maltitol, sorbitol, erythritol, erythritol, maltose, polydextrose, sucrose, trehalose and xylitol; calcium carbonate; dicalcium phosphate; pregelatinized starch; calcium sulfate; cellulose acetate; ethylcellulose; inulin; magnesium carbonate; magnesium oxide; maltodextrin; sodium bicarbonate; sodium carbonate; sodium chloride; more preferably mannitol and lactose.
- sugar alcohol such as mannitol, lactose, fructose, isomalt, lactitol, maltitol, sorbitol, erythritol, erythritol, maltose, polydextrose, sucrose
- Another aspect of the present invention provides a pharmaceutical composition comprising (a) Osimertinib mesylate,
- Another aspect of the present invention provides a pharmaceutical composition
- a pharmaceutical composition comprising
- the two diluents can be selected from sugar and sugar alcohol such as mannitol, lactose, fructose, isomalt, lactitol, maltitol, sorbitol, erythritol, erythritol, maltose, polydextrose, sucrose, trehalose and xylitol; calcium carbonate; dicalcium phosphate; pregelatinized starch; calcium sulfate; cellulose acetate; ethylcellulose; inulin; magnesium carbonate; magnesium oxide; maltodextrin; sodium bicarbonate; sodium carbonate; sodium chloride and microcrystalline cellulose; wherein the microcrystalline cellulose is in an amount greater than 30 % by weight of two or more diluents.
- sugar and sugar alcohol such as mannitol, lactose, fructose, isomalt, lactitol, maltitol, sorbitol, erythrito
- the pharmaceutical composition as defined herein may have from 5 to 70 % of the amount of the Osimertinib mesylate (a).
- the pharmaceutical composition of the present invention comprises Osimertinib mesylate and (ii) one or more of the following excipients:
- composition of the present invention comprises Osimertinib mesylate and (ii) one or more of the following excipients:
- An aspect of the present invention provides a pharmaceutical composition comprising,
- the two pharmaceutically acceptable diluents are selected from mannitol, lactose, dicalcium phosphate and pregelatinized starch, wherein microcrystalline cellulose in not a preferred diluent.
- Suitable disintegrants according to the present invention can be selected form but not limited to croscarmellose sodium, alginic acid, sodium alginate, carboxymethylcellulose calcium, chitosan, crospovidone, glycine, guar gum, hydroxypropyl cellulose, low-substituted hydroxypropyl cellulose, magnesium aluminum silicate, methylcellulose, povidone, sodium carboxymethylcellulose, sodium starch glycolate and starch.
- the one or more disintegrant comprise croscarmellose sodium, crospovidone, or a mixture thereof.
- the one or more disintegrant comprises croscarmellose sodium, low-substituted hydroxypropyl cellulose and crospovidone.
- Suitable pharmaceutical lubricant can be selected form but not limited to magnesium stearate, aluminium stearate , zinc stearate, calcium stearate, glyceryl behenate, glyceryl dibehenate, glyceryl monostearate, glyceryl palmitostearate, a mixture of benenate esters of glycerine (e.g. a mixture of glyceryl bihenehate, tribehenin and glyceryl behenate), myristic acid, palmitic acid, stearic acid, talc, tribehenin.
- the one or more pharmaceutical lubricants comprise magnesium stearate, stearic acid or a mixture thereof.
- the one or more pharmaceutical lubricants comprises magnesium stearate and sodium stearyl fumarate.
- glidant and“glidants” are intended to be interpreted in the context of pharmaceutical formulation science.
- Suitable glidants according to the present invention can be selected from but not limited to magnesium oxide, colloidal silicon dioxide, pyrogenic silica, hydrated sodium silioaluminate, magnesium stearate, stearic acid, calcium phosphate, magnesium carbonate, starch, corn starch and talc.
- the one or more pharmaceutical glidants comprise colloidal silicon dioxide, talc and starch.
- a pharmaceutical tablet comprising the pharmaceutical composition as defined herein.
- a pharmaceutical tablet comprising a tablet core wherein the tablet core comprises the pharmaceutical composition as defined herein and wherein the tablet core has a coating.
- the coating is a film coating.
- the film coating may be applied using conventional methods.
- a coating can be used to provide protection against, for example, moisture ingress or degradation by light, to colour the formulation, or to modify or control the release of the osimertinib mesylate from the formulation.
- the pharmaceutical composition is a pharmaceutical tablet composition (for oral administration).
- the pharmaceutical composition of the present invention is a pharmaceutical tablet composition suitable for oral administration to a human.
- the pharmaceutical composition of the present invention is a pharmaceutical tablet composition suitable for oral administration to a human who has cancer [particularly lung cancer, more particularly non-small cell lung cancer (NSCLC), for example EGFRM+NSCLC] .
- cancer particularly lung cancer, more particularly non-small cell lung cancer (NSCLC), for example EGFRM+NSCLC.
- NSCLC non-small cell lung cancer
- the pharmaceutical composition of the present invention is a pharmaceutical tablet composition suitable for oral administration to a human who has EGFRM+ and T790M+ non-small cell lung cancer.
- the pharmaceutical tablet comprising 40 mg and 80 mg osimertinib free base, equivalent to 47.7 mg and 95.4 mg of osimertinib mesylate respectively.
- a pharmaceutical composition as defined herein, for the manufacture of a medicament for the treatment of cancer.
- composition for use as a medicament.
- a pharmaceutical tablet as defined herein, for use as a medicament.
- composition for use in the treatment of cancer.
- a pharmaceutical tablet as defined herein, for use in the treatment of cancer.
- a method of treating cancer in a patient in need thereof comprises the oral administration of an effective amount of the pharmaceutical composition, as defined herein, to the patient.
- the patient is an adult human patient.
- a method of treating cancer in a patient in need thereof comprises the oral administration of an effective number of the pharmaceutical tablet(s), as defined herein, to the patient.
- cancer in any aspect, embodiment or claim where “cancer” is mentioned in this specification, the cancer may be further defined according to the embodiments listed below, unless such a definition would be inappropriate in a particular context.
- the cancer is non-small cell lung cancer.
- the cancer is EGFR-mutation positive non-small cell lung cancer.
- the cancer is T790M+ non-small cell lung cancer.
- the process for preparation of osimertinib mesylate tablet can be selected form, but not limited to wet granulation process, dry granulation process and direct compression process.
- the Osimertinib mesylate tablets were prepared using dry granulation method. Osimertinib mesylate with all intragranular excipients were sifted through the suitable mesh. Then the material was loaded in blender and after blending, compacted using roll compactor. The compacts were milled using suitable mill and screen. The milled granules were passed through suitable mesh. The extragranular excipients and lubricants were sifted through suitable mesh and were blended with milled granules. The blend was then compressed into tablets using suitable punches and then coated to a target build-up.
- the dissolution described herein were performed according to the general procedure of the United States Pharmacopoeia using Apparatus II (Paddle), at 50 rpm with 900 ml of OGD media (0.2% Nacl solution in water, adjust to pH 1.3) at a temperature of 37° C. The samples were withdrawn at 5, 10, 15, 20, 30 and 45 minutes.
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Abstract
La présente invention concerne une composition pharmaceutique comprenant de l'osimertinib ou un sel pharmaceutiquement acceptable de celui-ci et au moins un diluant. L'invention concerne également le procédé de préparation d'une telle composition pharmaceutique.
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
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IN201821001174 | 2018-01-10 | ||
ININ201821001174 | 2018-01-10 | ||
ININ201821022379 | 2018-06-14 | ||
IN201821022379 | 2018-06-14 |
Publications (1)
Publication Number | Publication Date |
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WO2019138346A1 true WO2019138346A1 (fr) | 2019-07-18 |
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ID=67218950
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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PCT/IB2019/050176 WO2019138346A1 (fr) | 2018-01-10 | 2019-01-10 | Composition pharmaceutique d'osimertinib |
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WO (1) | WO2019138346A1 (fr) |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2015101791A1 (fr) * | 2014-01-02 | 2015-07-09 | Astrazeneca Ab | Compositions pharmaceutiques comprenant azd9291 |
-
2019
- 2019-01-10 WO PCT/IB2019/050176 patent/WO2019138346A1/fr active Application Filing
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2015101791A1 (fr) * | 2014-01-02 | 2015-07-09 | Astrazeneca Ab | Compositions pharmaceutiques comprenant azd9291 |
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