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WO2024033459A1 - Compositions pharmaceutiques comprenant du 5-éthyl-4-méthyl-n-[4-[(2s)morpholin-2-yl]phényl]-1h-pyrazole-3-carboxamide - Google Patents

Compositions pharmaceutiques comprenant du 5-éthyl-4-méthyl-n-[4-[(2s)morpholin-2-yl]phényl]-1h-pyrazole-3-carboxamide Download PDF

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Publication number
WO2024033459A1
WO2024033459A1 PCT/EP2023/072132 EP2023072132W WO2024033459A1 WO 2024033459 A1 WO2024033459 A1 WO 2024033459A1 EP 2023072132 W EP2023072132 W EP 2023072132W WO 2024033459 A1 WO2024033459 A1 WO 2024033459A1
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WO
WIPO (PCT)
Prior art keywords
kernel
filler
weight
iii
total weight
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
Application number
PCT/EP2023/072132
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English (en)
Inventor
Davide DE FRANCO
Andreas Ewert
Emmanuela GAVI
Reto Maurer
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.)
F Hoffmann La Roche AG
Hoffmann La Roche Inc
Original Assignee
F Hoffmann La Roche AG
Hoffmann La Roche Inc
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Filing date
Publication date
Application filed by F Hoffmann La Roche AG, Hoffmann La Roche Inc filed Critical F Hoffmann La Roche AG
Priority to AU2023323858A priority Critical patent/AU2023323858A1/en
Priority to CN202380057973.6A priority patent/CN119654138A/zh
Priority to KR1020257003446A priority patent/KR20250044870A/ko
Priority to JP2025507557A priority patent/JP2025526086A/ja
Publication of WO2024033459A1 publication Critical patent/WO2024033459A1/fr
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
    • 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
    • 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
    • A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • A61K31/5375—1,4-Oxazines, e.g. morpholine
    • A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
    • 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
    • A61K9/2095—Tabletting processes; Dosage units made by direct compression of powders or specially processed granules, by eliminating solvents, by melt-extrusion, by injection molding, by 3D printing
    • 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
    • A61K9/28—Dragees; Coated pills or tablets, e.g. with film or compression coating
    • A61K9/2806—Coating materials
    • A61K9/282—Organic compounds, e.g. fats
    • A61K9/2826—Sugars or sugar alcohols, e.g. sucrose; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/06—Antimigraine agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/08—Antiepileptics; Anticonvulsants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/22—Anxiolytics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/24—Antidepressants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/04—Anorexiants; Antiobesity agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/12—Antihypertensives

Definitions

  • the present invention relates to pharmaceutical compositions comprising 5-ethyl-4- methyl-7V-[4-[(25) morpholin-2-yl]phenyl]-lH-pyrazole-3-carboxamide (Formula I), to processes for their preparation and their use in medical treatment.
  • WO2017157873 discloses the TAAR1 agonist 5-ethyl-4-methyl-N-[4-[(2S) morpholin-2-yl]phenyl]-lH-pyrazole- 3-carboxamide (Formula I), which is useful for the treatment of certain diseases and disorders of the central nervous system.
  • the compound of Formula I is also known under the INN ralmitaront (WHO Drug Information, Vol. 33, No. 2, 2019, p. 323).
  • ralmitaront For some of the medical indications of ralmitaront, such as schizophrenia, small sized tablets are required to improve patient compliance. Small sized tablets require the provision of API-excipient blends with a high drug load, for example, a drug load of 30% wt/wt API.
  • WO2017157873 discloses tablet and capsule formulations with high loads of ralmitaront. However, it was found that ralmitaront is cohesive and API-excipient blends containing it, especially in high amounts, do not flow well, making tablet production challenging. Additionally, the compound includes a secondary amine and a manufacturing process under high humidity conditions, such as wet granulation disclosed in WO2017157873 would increase the risk of nitrosamine formation.
  • the present invention provides new formulation blends comprising a high load of ralmitaront that avoid the wet granulation described in WO2017157873. Some of the new blends are suitable for roller compaction, while others are suitable for continuous direct compression, in particular for continuous mini-batch direct compression. The present invention also provides new processes for manufacturing tablets comprising ralmitaront, as well as the use of said tablets in medical therapy.
  • Figure 1 depicts a flow chart of the continuous mini-batch direct compression process according to the invention described in Example 1.
  • Figure 2 depicts a flow chart of the roller compaction according to the invention described in Example 2.
  • Figure 3 depicts the effect of the formulations represented by examples 5, 6 and 7, on the tablet tensile strength and Srel% (standard relative deviation of tablet weight) during the compaction process in the rotary press.
  • Batch 1 refers to the formulation of Example 5
  • batch 2 refers to the formulation of Example 6
  • batch 3 refers to the formulation of Example 7.
  • the tag that accompanies the batch number indicates on what tablet sample the measurement of the variables was made: “Start” means the tablet sample was collected at the start of tableting, “Middle” means the tablet sample was collected during the middle of tableting, “End” means the tablet sample was collected during the end of tableting, “Mixed” the tablet sample is constituted by a mixture of tablets in the middle and end of tableting.
  • dose strength relates to the absolute amount of the compound of Formula I in its free base form contained in a tablet formulation according to the invention, expressed in milligrams (mg). Consequently, if the compound of formula I is used in the form of a pharmaceutically acceptable salt, the term “dose strength” relates to the respective free base equivalent.
  • ralmitaronf relates to 5-ethyl-4-methyl-A-[4-[(25) morpholin-2- yl]phenyl]-lH-pyrazole-3-carboxamide (Formula I), and pharmaceutically acceptable salts thereof, in particular the mono hydrochloric acid salt.
  • filler refers to a substance added to a pharmaceutical composition to increase the weight and/or size of the pharmaceutical composition.
  • Pharmaceutically acceptable fillers are described in Remington’s Pharmaceutical Sciences and listed in Handbook of Pharmaceutical Excipients, Sheskey et al., 2017.
  • Non-limiting examples of fillers are starch (e.g., pregelatinized starch), cellulose (e.g., microcrystalline cellulose) and lactose (e.g., lactose monohydrate).
  • Preferred, yet non-limiting examples of fillers are cellulose and lactose.
  • disintegrant refers to a substance added to a pharmaceutical composition to help break apart (disintegrate), e.g., after administration, and release the active ingredient, such as Form B described herein.
  • Pharmaceutically acceptable disintegrants are described in Remington’ s Pharmaceutical Sciences and listed in Handbook of Pharmaceutical Excipients, Sheskey et al., 2017. Non-limiting examples of disintegrants are low substituted hydroxypropyl cellulose and croscarmellose sodium. A preferred, yet non-limiting example of a disintegrant is croscarmellose sodium.
  • glidanf and “lubricant” are used herein interchangeably and refer to a substance added to a pharmaceutical composition to help reduce the adherence of a granule of powder to equipment surfaces.
  • Pharmaceutically acceptable glidants are described in Remington’s Pharmaceutical Sciences and listed in Handbook of Pharmaceutical Excipients, Sheskey et al., 2017. Non-limiting examples of glidants are sodium stearyl fumarate and magnesium stearate. A preferred, yet non-limiting example of a glidant is sodium stearyl fumarate.
  • flow agent refers to a substance added to a pharmaceutical composition to enhance product flow by reducing interparticulate friction.
  • Pharmaceutically acceptable flow agents are described in Remington’s Pharmaceutical Sciences and listed in Handbook of Pharmaceutical Excipients, Sheskey et al., 2017.
  • Non-limiting examples of flow agents include silicon dioxide (colloidal), polyethylene glycol PEG 6000, fumed silicon dioxide Aerosil® 200, talc and the like.
  • a preferred, yet non-limiting example is silica, colloidal anhydrous.
  • MicroceLac® refers to an excipient comprising 75% alpha-lactose monohydrate and 25 % microcrystalline cellulose, wherein said alpha-lactose monohydrate and microcrystalline cellulose have been co-processed by spray drying.
  • SCC90 refers to an excipient comprising 98% microcrystalline cellulose and 2% colloidal silicon dioxide, wherein said microcrystalline cellulose and colloidal silicon dioxide have been co-processed by spray drying.
  • Lupress® refers to an excipient comprising 93% lactose monohydrate, 3.5% povidone having a K- value of 30 (“Kollidon® 30”) and 3.5% crospovidone having a bulk density of 0.30 - 0.40 g/mL (“Kollidon® CL”).
  • HPMC refers to hydroxypropylmethylcellulose.
  • treating means an alleviation, in whole or in part, of a disorder, disease or condition, or one or more of the symptoms associated with a disorder, disease, or condition, or slowing or halting of further progression or worsening of those symptoms, or alleviating or eradicating the cause(s) of the disorder, disease, or condition itself.
  • the term “preventing” includes: preventing or delaying the appearance of clinical symptoms of the state, disorder or condition developing in a mammal and especially a human that may be afflicted with or predisposed to the state, disorder or condition but does not yet experience or display clinical or subclinical symptoms of the state, disorder or condition.
  • the term “patient” refers to a human.
  • the present invention provides a tablet comprising:
  • the tablet according to the invention comprises the compound of
  • the dose strength of the tablet according to the invention is 40 mg to 160 mg, preferably 45 mg to 150 mg, more preferably 45 mg or 150 mg.
  • the dose strength of the tablet according to the invention is In a preferred embodiment, the dose strength of the tablet according to the invention is 150 mg.
  • the coating of the tablet according to the invention comprises:
  • HPMC represents 34% ⁇ 1% of the total weight of the coating
  • lactose monohydrate represents 28% ⁇ 1% of the total weight of the coating
  • titanium dioxide represents 26% ⁇ 1% of the total weight of the coating
  • (iv) macrogol represents 12% ⁇ 1% of the total weight of the coating.
  • the coating of the tablet according to the invention is Opadry II White.
  • the kernel further comprises the following excipients:
  • said filler is selected from MicroceLac® 100 and SMCC90;
  • said disintegrant is croscarmellose sodium
  • said glidant is sodium stearyl fumarate.
  • said filler is MicroceLac® 100;
  • said disintegrant is croscarmellose sodium
  • said glidant is sodium stearyl fumarate.
  • said disintegrant is croscarmellose sodium
  • said glidant is sodium stearyl fumarate.
  • the weight of said filler represents 58% ⁇ 1% of the total weight of the kernel
  • the weight of said disintegrant represents 5% ⁇ 1% of the total weight of the kernel
  • the weight of said glidant represents 4% ⁇ 1% of the total weight of the kernel
  • the weight of said compound of Formula I, or a pharmaceutically acceptable salt thereof represents 33% ⁇ 1% of the total weight of the kernel.
  • the kernel further comprises the following excipients:
  • said first filler is Ludipress®
  • said second filler is microcrystalline cellulose
  • said lubricant is sodium stearyl fumarate.
  • the weight of said first filler represents 43% ⁇ 1% of the total weight of the kernel
  • the weight of said second filler represents 20% ⁇ 1% of the total weight of the kernel
  • the weight of said lubricant represents 4% ⁇ 1% of the total weight of the kernel
  • the weight of said compound of Formula I, or a pharmaceutically acceptable salt thereof represents 33% ⁇ 1% of the total weight of the kernel.
  • the present invention provides a continuous process for manufacturing a tablet based on Formulation A or B described herein, comprising: (i) feeding the API and components (i)-(iii) from four individual screw feeders into a blender;
  • step (ii) blending the mixture of step (i);
  • step (iv) spraying a film coating suspension onto the tablet kernels from step (iii).
  • the kernel further comprises the following excipients:
  • said first filler is microcrystalline cellulose
  • said second filler is lactose monohydrate
  • said disintegrant is croscarmellose sodium
  • said glidant is sodium stearyl fumarate
  • said flow agent is colloidal silicon dioxide.
  • the weight of said first filler represents 33% ⁇ 1% of the total weight of the kernel
  • the weight of said second filler represents 23% ⁇ 1% of the total weight of the kernel
  • the weight of said disintegrant represents 5% ⁇ 1% of the total weight of the kernel
  • the weight of said glidant represents 4% ⁇ 1% of the total weight of the kernel
  • the present invention provides a roller compaction process for manufacturing a tablet based on Formulation C described herein, comprising:
  • step (iii) screening a 1 st portion of the lubricant and adding it to the blend from step (ii);
  • step (iv) performing a roller compaction with the blend from step (iii) to form granules
  • step (v) screening a 2 nd portion of the lubricant and adding it to the granules from step (iv);
  • step (vi) compressing the blend from step (v) into tablet kernels
  • step (vii) spraying a film coating suspension onto the tablet kernels from step (vi).
  • the present invention provides a tablet as described herein, for use as a medicament.
  • the present invention provides a method for treating or preventing a TAAR1(4) mediated disease in a patient, comprising administering one or more tablets described herein to the patient.
  • the present invention provides a tablet described herein, for use in a method of treating or preventing a TAAR1(4) mediated disease in a patient.
  • the present invention provides the use of a tablet described herein in a method of treating or preventing a TAAR1(4) mediated disease in a patient.
  • said TAAR1(4) mediated disease is selected from depression, anxiety disorders, bipolar disorder, attention deficit hyperactivity disorder (ADHD), stress-related disorders, schizophrenia, Parkinson’s disease, Alzheimer’s disease, epilepsy, migraine, hypertension, substance abuse, addiction, eating disorders, diabetes, diabetic complications, obesity, dyslipidemia, disorders of energy consumption and assimilation, disorders and malfunction of body temperature homeostasis, disorders of sleep and circadian rhythm, and cardiovascular disorders.
  • ADHD attention deficit hyperactivity disorder
  • said TAAR1(4) mediated disease is selected from schizophrenia, substance abuse, and addiction. In a particularly preferred embodiment, said TAAR1(4) mediated disease is schizophrenia.
  • said TAAR1(4) mediated disease is substance abuse.
  • said TAAR1(4) mediated disease is addiction.
  • Example 1 Tablet Formation from a Continuous Mini-Batch Direct Compression Process Equipment
  • step 6. Prepare film coating suspension and spray film coat onto tablet cores obtained from step 4. Perform IPC on the average weight, thickness and disintegration time of film-coated tablets.
  • the API is ralmitaront mono hydrochloride
  • excipient (i) is a filler selected from MicroceLac® 100 and SMCC90
  • excipient (ii) is a disintegrant being croscarmellose sodium
  • excipient (iii) is a lubricant being sodium stearyl fumarate (see Examples 5, 7 and 9).
  • the API is ralmitaront mono hydrochloride
  • excipient (i) is a first filler being Ludipress®
  • excipient (ii) is a second filler being microcrystalline cellulose
  • excipient (iii) is a lubricant being sodium stearyl fumarate (see Example 6).
  • Example 2 Tablet Formation from a Roller Compaction Process
  • step 6. Perform tablet manufacturing with final blend obtained from step 5. Perform IPC on the individual tablet weight, hardness, thickness, friability and disintegration time for tablet cores.
  • step 7. Prepare film coating suspension and spray film coat onto tablet cores obtained from step 6. Perform IPC on the average weight, thickness and disintegration time of film-coated tablets.
  • MicroceLac® 100 is a commercially available excipient consisting of co-processed microcrystalline cellulose and alpha-lactose monohydrate. All excipients used in the formulation are compendial (Ph. Eur. and/or USP/NF) grade.
  • the tablets may be manufactured according to the continuous process described in Example 1.
  • Ludipress® is a commercially available excipient consisting of co-processed lactose monohydrate, povidone and crospovidone.
  • the tablets may be manufactured according to the continuous process described in Example 1.
  • SMCC90 is a commercially available excipient consisting of silicified microcrystalline cellulose.
  • All excipients used in the formulation are compendial (Ph. Eur. and/or USP/NF) grade.
  • the tablets may be manufactured according to the continuous process described in
  • the tablets may be manufactured according to the process described in Example 2.
  • MicroceLac® 100 is a commercially available excipient consisting of co-processed microcrystalline cellulose and alpha-lactose monohydrate.
  • All excipients used in the formulation are compendial (Ph. Eur. and/or USP/NF) grade.
  • the tablets may be manufactured according to the continuous process described in Example 1.
  • Ludipress® is a commercially available excipient consisting of co-processed lactose monohydrate, povidone and crospovidone.
  • All excipients used in the formulation are compendial (Ph. Eur. and/or USP/NF) grade.
  • the tablets may be manufactured according to the continuous process described in
  • SMCC90 is a commercially available excipient consisting of silicified microcrystalline cellulose.
  • All excipients used in the formulation are compendial (Ph. Eur. and/or USP/NF) grade.
  • the tablets may be manufactured according to the continuous process described in

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  • Diabetes (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
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  • Obesity (AREA)
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  • Pain & Pain Management (AREA)
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  • Child & Adolescent Psychology (AREA)
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Abstract

La présente invention concerne des compositions pharmaceutiques comprenant du 5-éthyl-4-méthyl-N-[4-[(2S)morpholin-2-yl]phényl]-1H-pyrazole-3-carboxamide (ralmitaront), des procédés pour leur préparation et leur utilisation pour un traitement médical.
PCT/EP2023/072132 2022-08-12 2023-08-10 Compositions pharmaceutiques comprenant du 5-éthyl-4-méthyl-n-[4-[(2s)morpholin-2-yl]phényl]-1h-pyrazole-3-carboxamide Ceased WO2024033459A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
AU2023323858A AU2023323858A1 (en) 2022-08-12 2023-08-10 Pharmaceutical compositions comprising 5-ethyl-4-methyl- n-[4-[(2 s) morpholin-2-yl]phenyl]-1h-pyrazole-3-carboxamide
CN202380057973.6A CN119654138A (zh) 2022-08-12 2023-08-10 包含5-乙基-4-甲基-n-[4-[(2s)吗啉-2-基]苯基]-1h-吡唑-3-甲酰胺的药物组合物
KR1020257003446A KR20250044870A (ko) 2022-08-12 2023-08-10 5-에틸-4-메틸-n-[4-[(2s) 모르폴린-2-일]페닐]-1h-피라졸-3-카르복스아미드를 포함하는 약제학적 조성물
JP2025507557A JP2025526086A (ja) 2022-08-12 2023-08-10 ５－エチル－４－メチル－ｎ－［４－［（２ｓ）モルホリン－２－イル］フェニル］－１ｈ－ピラゾール－３－カルボキサミドを含む医薬組成物

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP22190194 2022-08-12
EP22190194.5 2022-08-12

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WO2024033459A1 true WO2024033459A1 (fr) 2024-02-15

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JP (1) JP2025526086A (fr)
KR (1) KR20250044870A (fr)
CN (1) CN119654138A (fr)
AU (1) AU2023323858A1 (fr)
TW (1) TW202416999A (fr)
WO (1) WO2024033459A1 (fr)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012168260A1 (fr) * 2011-06-09 2012-12-13 F. Hoffmann-La Roche Ag Dérivés de pyrazole
WO2017157873A1 (fr) 2016-03-17 2017-09-21 F. Hoffmann-La Roche Ag Dérivé de 5-éthyl-4-méthyl-pyrazole-3-carboxamide ayant une activité en tant qu'agoniste de taar
WO2021185878A1 (fr) * 2020-03-19 2021-09-23 F. Hoffmann-La Roche Ag Sels et formes cristallines d'un agoniste de taar1

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012168260A1 (fr) * 2011-06-09 2012-12-13 F. Hoffmann-La Roche Ag Dérivés de pyrazole
WO2017157873A1 (fr) 2016-03-17 2017-09-21 F. Hoffmann-La Roche Ag Dérivé de 5-éthyl-4-méthyl-pyrazole-3-carboxamide ayant une activité en tant qu'agoniste de taar
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