WO2023184282A1 - X842 formulation - Google Patents

X842 formulation Download PDF

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Publication number
WO2023184282A1
WO2023184282A1 PCT/CN2022/084214 CN2022084214W WO2023184282A1 WO 2023184282 A1 WO2023184282 A1 WO 2023184282A1 CN 2022084214 W CN2022084214 W CN 2022084214W WO 2023184282 A1 WO2023184282 A1 WO 2023184282A1
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WO
WIPO (PCT)
Prior art keywords
solid dispersion
pharmaceutical formulation
carrier
tablet
spray drying
Prior art date
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Ceased
Application number
PCT/CN2022/084214
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English (en)
French (fr)
Inventor
Jianxin Wang
Jiangang YANG
Pingsheng HU
Ming Lu
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Guizhou Sinorda Biomedicine Co Ltd
Original Assignee
Guizhou Sinorda Biomedicine Co Ltd
Priority date (The priority date 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 date listed.)
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Publication date
Application filed by Guizhou Sinorda Biomedicine Co Ltd filed Critical Guizhou Sinorda Biomedicine Co Ltd
Priority to PCT/CN2022/084214 priority Critical patent/WO2023184282A1/en
Priority to AU2023247528A priority patent/AU2023247528A1/en
Priority to PCT/CN2023/083375 priority patent/WO2023185624A1/en
Priority to CN202411410163.7A priority patent/CN119139298A/zh
Priority to CN202380010889.9A priority patent/CN117157059B/zh
Priority to JP2024557950A priority patent/JP2025511145A/ja
Priority to KR1020247035992A priority patent/KR20240165457A/ko
Priority to EP23719627.4A priority patent/EP4499046A1/en
Publication of WO2023184282A1 publication Critical patent/WO2023184282A1/en
Priority to MX2024011716A priority patent/MX2024011716A/es
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—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
    • A61K31/4353—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 ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/437—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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
    • 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
    • A61K47/32—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers, poly(meth)acrylates, or polyvinyl pyrrolidone
    • 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
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
    • 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
    • A61K9/141—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers
    • A61K9/146—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers with organic macromolecular 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
    • A61K9/14—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
    • 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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants

Definitions

  • the present disclosure relates to the field of treatment of a gastrointestinal inflammatory disease or a gastric acid related disease and in particular a solid dispersion of X842 developed for this purpose.
  • WO 2010/063876 discloses that the compound 5- ⁇ 2- [ ( ⁇ 8- [ (2, 6-dimethylbenzyl) amino] -2, 3-dimethylimidazo [1, 2-a] pyridine-6-yl ⁇ carbonyl) -amino] ethoxy ⁇ -5-oxopentanoic acid, which is often referred to as X842, is an effective inhibitor of gastric secretion.
  • X842 has the following formula:
  • US2022002297 discloses two crystalline forms of X842 and states that for use in pharmaceutical preparations, it is desirable that the active pharmaceutical ingredient (API) is in a highly crystalline form.
  • a pharmaceutical formulation for oral administration comprising a solid dispersion comprising amorphous X842 and a water-soluble, amphiphilic carrier.
  • the organic solvent is any solvent that is suitable for spray drying X842, and is preferably absolute ethanol, methanol, acetone, tetrahydrofuran, dimethyl sulfoxide and chloroform.
  • a solid dispersion comprising amorphous X842 and a water-soluble, amphiphilic carrier, wherein said solid dispersion is obtainable by spray drying a solution of X842 and the cartier.
  • the organic solvent is any solvent that is suitable for spray drying X842, and is preferably absolute ethanol, methanol, acetone, tetrahydrofuran, dimethyl sulfoxide and chloroform.
  • a tablet comprising the pharmaceutical formulation of any one of items 1-13 or the solid dispersion of any one of items 14-18.
  • the tablet of item 19 further comprising a disintegrant, such as polyvinylpolypyrrolidone.
  • a cellulosic excipient such as microcrystalline cellulose (MCC) .
  • Fig. 1 shows the solubility of X842 in mixtures or solid dispersions (formed by the solvent method) with different carriers in different mass ratios (see Example 1 below) .
  • Fig. 2 shows X842 solubility measurement results for different solid dispersions and physical mixtures. “Sol” means Soluplus.
  • Fig. 3 shows PXRD diffractograms for three different solid dispersions (one prepared by spray drying, one prepared by hot melt extrusion and one prepared by the solvent method) , a physical mixture, Soluplus and X842.
  • Fig. 4 shows PXRD diffractograms for Samples 3.1-3.8 (the preparations of these samples are described in the Examples section below) .
  • Fig. 5 shows PXRD diffractograms for Samples 3.9-3.12 (the preparations of these samples are described in the Examples section below) .
  • Fig. 6 shows X842 solubility measurement results for Sample 3.1, 3.2 and 3.10 (solid dispersions formed by spray drying) and Sample 3.12 (physical mixture) .
  • Fig. 7 shows the X842 dissolution from tablets formed from Compositions 1-4 (the preparations of these tablets is described in the Examples section below) and from a reference capsule.
  • a pharmaceutical formulation for oral administration comprises a solid dispersion comprising amorphous X842 and a water-soluble, amphiphilic carrier. This formulation facilitates quick dissolution of X842 and may thus be referred to as an immediate release pharmaceutical formulation.
  • the carrier is typically polymeric.
  • the polymeric carrier comprises vinylcaprolactam and/or vinyl acetate.
  • the polymeric carrier comprises vinylcaprolactam and vinyl acetate.
  • the average molecular weight (as determined by gel permeation chromatography) of the polymeric carrier is preferably in the range of 40,000 -250,000 g/mol, more preferably in the range of 80,000 -150,000 g/mol.
  • polymeric carrier that comprises vinylcaprolactam and vinyl acetate and has an average molecular weight (as determined by gel permeation chromatography) in the range of 80,000 -150,000 g/mol is Soluplus from BASF.
  • the dry weight ratio of X842 to the carrier is preferably between 2 ⁇ 1 and 1 ⁇ 20, preferably between 1 ⁇ 1 and 1 ⁇ 10, more preferably between 1 ⁇ 1 and 1 ⁇ 10, more preferably between 1 ⁇ 2 and 1 ⁇ 7, more preferably between 1 ⁇ 3 and 1 ⁇ 7, most preferably between 1 ⁇ 3 and 1 ⁇ 5.
  • the solid dispersion is formed by spray drying.
  • the solid dispersion is obtained by spray drying a solution of X842 and the carrier.
  • the solution may for example be an ethanol solution. Further embodiments of the spray drying are discussed below in connection to the third aspect.
  • the pharmaceutical formulation of the first aspect may for example be in the form of a unit dose.
  • the amount of amorphous X842 may be 10-100 mg, such as 10-60 mg, such as 10-40 mg, such as 10-25 mg, such as 10-24 mg.
  • the efficient dissolution of X842 means that the amount of X842 may be relatively low.
  • the pharmaceutical formulation of the first aspect is provided for use in a method of treatment of a gastrointestinal inflammatory disease or a gastric acid related disease, such as erosive gastroesophageal reflux disease (eGERD) .
  • a gastric acid related disease such as erosive gastroesophageal reflux disease (eGERD)
  • eGERD erosive gastroesophageal reflux disease
  • the pharmaceutical formulation is intended to be administrated orally.
  • a solid dispersion comprising amorphous X842 and a water-soluble, amphiphilic carrier, wherein said solid dispersion is obtainable by spray drying a solution, such as an ethanol solution, of X842 and the carrier.
  • the nozzle temperature may for example be in the range of 55-99 °C, such as in the range of 65-95 °C, such as in the range of 70-85 °C during said spray drying. Further, the temperature of the solution being fed to the nozzle during said spray drying may be in the range of 55-99 °C, such as in the range of 65-95 °C, such as in the range of 70-85 °C.
  • the nozzle temperature and the temperature of the solution being fed to the nozzle are preferably in the range of 65-78 °C, more preferably in the range of 65-75 °C.
  • the solid dispersion of the third aspect is provided for use in a method of treatment of a gastrointestinal inflammatory disease or a gastric acid related disease, such as eGERD.
  • the solid dispersion is intended to be administrated orally.
  • a tablet comprising the pharmaceutical formulation of the first aspect or the solid dispersion of the third aspect.
  • the tablet may further comprise a disintegrant, such as a non-cellulosic disintegrant.
  • a disintegrant such as a non-cellulosic disintegrant.
  • a preferred example of a non-cellulosic disintegrant is polyvinylpolypyrrolidone.
  • the dry weight ratio of disintegrant to X842 is typically at least 1.1 ⁇ 1, such as at least 1.4 ⁇ 1, preferably at least 1.7 ⁇ 1, such as at least 2 ⁇ 1, such as at least 2.8 ⁇ 1, . An upper limit for this dry weight ratio may be 4 ⁇ 1.
  • the tablet further comprises a cellulosic excipient and/or lactose.
  • the cellulosic excipient may for example be MCC.
  • the amount of amorphous X842 in the tablet may be 10-100 mg, such as 10-60 mg, such as 10-40 mg, such as 10-25 mg, such as 10-24 mg.
  • the tablet of the fifth aspect is provided for use in a method of treatment of a gastrointestinal inflammatory disease or a gastric acid related disease, such as eGERD.
  • the tablet is intended to be administrated orally.
  • the subject of the therapeutic methods discussed above is preferably a human.
  • a seventh aspect of the present disclosure there is provided use of the pharmaceutical formulation of first aspect or the solid dispersion of the third aspect or the tablet of the fifth aspect for preparation of the medicament for treating a gastrointestinal inflammatory disease or a gastric acid related disease, such as erosive gastroesophageal reflux disease (eGERD) .
  • eGERD erosive gastroesophageal reflux disease
  • Solid dispersions of X842 and different carriers were prepared by the solvent method, and their solubility in pH 6.8 was determined.
  • API API
  • carrier was added to a 250 ml beaker and about 150 ml of anhydrous ethanol was then added.
  • the amount of API was about 70 mg and the API to carrier dry weight ratio was 1 ⁇ 3, 1 ⁇ 5 or 1 ⁇ 10.
  • the solution was added to porcelain dish and placed in an 80°C water bath to evaporate the solvent.
  • the solid residue was then placed in a vacuum drying oven at 40°C for 24h.
  • the dried residue was ground finely through a 50-mesh sieve
  • table 1 shows that the Soluplus carrier is ineffective in physical mixture with the API (also in comparison to most of the other carriers) , but outperforms all the other carriers in a solid dispersion independent of the ratio (see also Fig. 1) .
  • a solid dispersion was prepared from X842 (17 wt. %) and Soluplus (83 wt. %) according to the following:
  • the solid dispersion was analyzed using powder X-ray diffraction (PXRD) . Further, the X842 solubility of the solid dispersion was tested. This is described below.
  • a solid dispersion was prepared from X842 (17 wt. %) and Soluplus (83 wt. %) according to the following:
  • the X842 solubility of the solid dispersion was tested. This is described below.
  • a solid dispersion was prepared from X842 (17 wt. %) , polymer carrier polyvinyl alcohol (66 wt. %) and sorbitol (17 wt. %) according to the following:
  • the X842 solubility of the solid dispersion was tested. This is described below.
  • a solid dispersion was prepared from X842 (17 wt. %) , polymer carrier polyvinyl alcohol (41.5 wt. %) and sorbitol (41.5 wt. %) according to the following:
  • the X842 solubility of the solid dispersion was tested. This is described below.
  • a solid dispersion was prepared from X842 (17 wt. %) and Soluplus (83 wt. %) using spray drying according to the following:
  • the solid dispersion was analyzed using powder X-ray diffraction (PXRD) . Further, the X842 solubility of the solid dispersion was tested. This is described below.
  • Example 2 which has superior X842 solubility
  • Example 2.1 prepared by hot melt extrusion at 160°C
  • PXRD was carried out on a X842/Soluplus solid dispersion formed by the solvent method (1 ⁇ 5 dry weight ratio, see Example 1) , a X842/Soluplus physical mixture (1 ⁇ 5 dry weight ratio) , Soluplus alone and X842 alone were also analyzed to provide further references.
  • Fig. 3 shows that the crystallinity of X842 is retained in the solid dispersions formed by hot melt extrusion and the solvent method and in the physical mixture.
  • Fig. 2 shows that these forms have inferior X842 solubility compared to the solid dispersion formed by spray drying (Example 5.2) .
  • Fig. 3 shows that X842 is amorphous in the solid dispersion formed by spray drying. Figs. 2 and 3 thus show that a solid dispersion in which X842 is amorphous is key to X842's solubility.
  • Fig. 5 The resulting PXRD diffractograms are presented in Fig. 5, which again shows that spray drying of a X842/Soluplus solution produce a solid dispersion comprising amorphous X842, not only in a 1 ⁇ 5 ratio, but also in 1 ⁇ 3 and 1 ⁇ 1 ratios.
  • Fig. 6 shows that the solid dispersions comprising amorphous X842 have drastically improved X842 solubility compared to a physical mixture comprising crystalline X842.
  • Fig. 6 further shows that an X842 to Soluplus ratio of 1 ⁇ 5 or 1 ⁇ 3 is more effective than a X842 to Soluplus ratio of 1 ⁇ 1 and that out of the ratios tested, 1 ⁇ 5 is the most effective.
  • Tablets were prepared from compositions comprising various solid dispersions of X842 and Soluplus prepared by spray drying or hot-melt extrusion. The weight of each tablet was 350 mg and the amount of X842 in each tablet was 25 mg.
  • dissolution degree determination method Choinese Pharmacopoeia 2020 edition of the four general principles 0931 second method paddle method
  • two tablets corresponding to about 50 mg of X842 for each composition were placed in a cup and 900 ml of pH 6.8 phosphate buffer (dissolution medium) was added to the cup to prepare a suspension.
  • a 5 ml suspension sample was taken (while supplementing the same volume of media) and filtered through a 0.22 ⁇ m microporous membrane.
  • the filtrate was diluted two times with methanol and then filtered again and injected into HPLC to determine the solubility by measuring the peak area.
  • capsules containing a composition comprising crystalline X842 was suspended and analyzed in the same way.
  • Fig. 7 shows that the tablets comprising a solid dispersion of amorphous X842 (i.e. the tablets formed from compositions 1, 3 and 4) outperformed the tablet comprising a solid dispersion of crystalline X842 (composition 2) and the capsule reference (also comprising crystalline X842) .

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Epidemiology (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Inorganic Chemistry (AREA)
  • Nutrition Science (AREA)
  • Physiology (AREA)
  • Medicinal Preparation (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
PCT/CN2022/084214 2022-03-30 2022-03-30 X842 formulation Ceased WO2023184282A1 (en)

Priority Applications (9)

Application Number Priority Date Filing Date Title
PCT/CN2022/084214 WO2023184282A1 (en) 2022-03-30 2022-03-30 X842 formulation
JP2024557950A JP2025511145A (ja) 2022-03-30 2023-03-23 Ｘ８４２製剤
PCT/CN2023/083375 WO2023185624A1 (en) 2022-03-30 2023-03-23 X842 formulation
CN202411410163.7A CN119139298A (zh) 2022-03-30 2023-03-23 X842制剂
CN202380010889.9A CN117157059B (zh) 2022-03-30 2023-03-23 X842制剂
AU2023247528A AU2023247528A1 (en) 2022-03-30 2023-03-23 X842 formulation
KR1020247035992A KR20240165457A (ko) 2022-03-30 2023-03-23 X842 제제
EP23719627.4A EP4499046A1 (en) 2022-03-30 2023-03-23 X842 formulation
MX2024011716A MX2024011716A (es) 2022-03-30 2024-09-24 Formulacion de x842

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/CN2022/084214 WO2023184282A1 (en) 2022-03-30 2022-03-30 X842 formulation

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WO2023184282A1 true WO2023184282A1 (en) 2023-10-05

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PCT/CN2022/084214 Ceased WO2023184282A1 (en) 2022-03-30 2022-03-30 X842 formulation
PCT/CN2023/083375 Ceased WO2023185624A1 (en) 2022-03-30 2023-03-23 X842 formulation

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PCT/CN2023/083375 Ceased WO2023185624A1 (en) 2022-03-30 2023-03-23 X842 formulation

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EP (1) EP4499046A1 (https=)
JP (1) JP2025511145A (https=)
KR (1) KR20240165457A (https=)
CN (2) CN119139298A (https=)
AU (1) AU2023247528A1 (https=)
MX (1) MX2024011716A (https=)
WO (2) WO2023184282A1 (https=)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2024230943A1 (en) * 2023-05-08 2024-11-14 Cinclus Pharma Holding AB (publ) Linaprazan glurate for treating gastroesophageal reflux disease (gerd)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2026032974A1 (en) 2024-08-05 2026-02-12 Cinclus Pharma Holding AB (publ) Formulation of linaprazan glurate

Citations (3)

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Publication number Priority date Publication date Assignee Title
WO2010063876A1 (en) 2008-12-03 2010-06-10 Dahlstroem Mikael Imidazopyridine derivatives which inhibit the secretion of gastric acid
WO2021089580A1 (en) * 2019-11-04 2021-05-14 Cinclus Pharma Ag Oral formulation of x842
US20220002297A1 (en) 2020-07-02 2022-01-06 Cinclus Pharma Ag Polymorphs of x842

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JP2004518709A (ja) * 2001-02-13 2004-06-24 アストラゼネカ・アクチエボラーグ 新規放出修飾製剤
US20050249799A1 (en) * 2004-03-03 2005-11-10 Spherics, Inc. Polymeric drug delivery system for hydrophobic drugs
CN101513403A (zh) * 2008-02-21 2009-08-26 上海慧德医药科技有限公司 含有苯并咪唑类化合物的药物制剂
CN103301066B (zh) * 2012-03-15 2018-12-07 苏州泽璟生物制药有限公司 一种改善吸收性能的固体分散体及其制备
CN106279151A (zh) * 2015-06-26 2017-01-04 江苏太瑞生诺生物医药科技有限公司 5-(2-(8-((2,6-二甲基苄基)氨基)-2,3-二甲基咪唑并[1,2-a]吡啶-6-甲酰胺基)乙氧基)-5-氧代戊酸的固体形式及其制备方法
WO2018026764A1 (en) * 2016-08-01 2018-02-08 University Of Rochester Nanoparticles for controlled release of anti-biofilm agents and methods of use
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Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010063876A1 (en) 2008-12-03 2010-06-10 Dahlstroem Mikael Imidazopyridine derivatives which inhibit the secretion of gastric acid
WO2021089580A1 (en) * 2019-11-04 2021-05-14 Cinclus Pharma Ag Oral formulation of x842
US20220002297A1 (en) 2020-07-02 2022-01-06 Cinclus Pharma Ag Polymorphs of x842

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2024230943A1 (en) * 2023-05-08 2024-11-14 Cinclus Pharma Holding AB (publ) Linaprazan glurate for treating gastroesophageal reflux disease (gerd)

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JP2025511145A (ja) 2025-04-15
AU2023247528A1 (en) 2024-09-26
CN119139298A (zh) 2024-12-17
EP4499046A1 (en) 2025-02-05
CN117157059B (zh) 2024-09-13
WO2023185624A1 (en) 2023-10-05
MX2024011716A (es) 2024-11-08
KR20240165457A (ko) 2024-11-22
CN117157059A (zh) 2023-12-01

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