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WO2025190151A1 - Composés benzosélénazoles ainsi que leur procédé de préparation et leur utilisation - Google Patents

Composés benzosélénazoles ainsi que leur procédé de préparation et leur utilisation

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Publication number
WO2025190151A1
WO2025190151A1 PCT/CN2025/081112 CN2025081112W WO2025190151A1 WO 2025190151 A1 WO2025190151 A1 WO 2025190151A1 CN 2025081112 W CN2025081112 W CN 2025081112W WO 2025190151 A1 WO2025190151 A1 WO 2025190151A1
Authority
WO
WIPO (PCT)
Prior art keywords
compound
acid
formula
alkyl
benzoselenazepine
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.)
Pending
Application number
PCT/CN2025/081112
Other languages
English (en)
Chinese (zh)
Inventor
黄金文
李中原
刘运立
金慧泽
沈孝坤
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.)
Convalife Shanghai Co Ltd
Zhejiang Convalife Pharmaceutical Co Ltd
Original Assignee
Convalife Shanghai Co Ltd
Zhejiang Convalife Pharmaceutical 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.)
Filing date
Publication date
Application filed by Convalife Shanghai Co Ltd, Zhejiang Convalife Pharmaceutical Co Ltd filed Critical Convalife Shanghai Co Ltd
Publication of WO2025190151A1 publication Critical patent/WO2025190151A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

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
    • A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
    • C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
    • C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D281/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one sulfur atom as the only ring hetero atoms
    • C07D281/02—Seven-membered rings
    • C07D281/04—Seven-membered rings having the hetero atoms in positions 1 and 4
    • C07D281/08—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
    • C07D281/10—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
    • C07D305/02—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D305/04—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D305/08—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D517/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having selenium, tellurium, or halogen atoms as ring hetero atoms

Definitions

  • the present invention relates to a benzoselenazepine Compounds and their preparation methods and uses.
  • Respiratory syncytial virus is one of the most contagious human respiratory viruses. It's aptly named because RSV-infected cells fuse together, forming large cell structures resembling syncytia. It infects 3-10% of the world's population annually and is the most common cause of acute lower respiratory tract illness in infants and young children. It is also the leading cause of hospitalization for lower respiratory tract infections, bronchiolitis, and even death in children under five years of age. Globally, it causes approximately 34 million cases of lower respiratory tract infections each year, including up to 200,000 deaths in children under five. RSV can also cause severe lung infections and death in the elderly.
  • RSV is an enveloped virus belonging to the family Streptococcus pneumoniae.
  • the RSV genome consists of 10 genes encoding 11 proteins: nonstructural proteins 1 and 2 (NS1 and NS2), nucleoprotein (N), phosphoprotein (P), matrix protein (M), small hydrophobic protein (SH), fusion protein (F), attachment glycoprotein (G), human RNA-dependent RNA polymerase (L), and transcription antibody terminator protein (M2-1) and M2-2 proteins.
  • RSV is a major cause of acute lower respiratory tract illness and hospitalization in young children. Globally, RSV causes 33.8 million children under the age of 5 years old each year, of which 3.4 million children require hospitalization for acute lower respiratory tract illness (Ramagopal G., et al, Journal of Clinical and Diagnostic Research, 2016, 10(8): SC05-SC08).
  • RSV virus particle inactivators RSV virus particle inactivators
  • RSV replication/protein synthesis inhibitors RSV cell binding inhibitors
  • RSV cell invasion inhibitors RSV cell invasion inhibitors
  • host cell regulators of apoptosis only a few have entered Phase I or II clinical trials.
  • Arrow Therapeutics completed a 5-year Phase II clinical trial of the nucleocapsid (N) protein inhibitor RSV-604 in stem cell transplant patients in February 2010 (www.clinicaltriaIs.gov), but has not yet announced the final results. Most other small molecules have suspended their trials for various reasons.
  • N nucleocapsid
  • RSV-F respiratory syncytial virus fusion protein
  • RNAi therapeutics against RSV are also currently under investigation.
  • ALN-RSV01 AInyIam Pharmaceuticals, MA, LSA
  • ALN-RSV01 is a siRNA targeting the RSV gene.
  • Administration of ALN-RSV01 as a nasal spray 2 days before and 3 days after RSV inoculation reduced infection rates in adult volunteers (DeVincenzo J. et al., Proc Natl Acad Sci U S A. 2010 May 11;107(19):8800-5).
  • results were insufficient to conclude on antiviral efficacy, although some product efficacy was observed (Zamora MR et al., Am T Respir Crit Care Med. 2011 Feb 15;183(4):531-8).
  • Alios's nucleic acid analog ALS-8176 can terminate RNA chain synthesis, inhibit L protein polymerization, and reduce respiratory syncytial virus load in more than 85% of volunteers: Gilead's RSV fusion inhibitor GS-5806 oral treatment can reduce viral load, mucus quality, and symptom scores, etc.
  • the technical problem to be solved by the present invention is to overcome the problems of single structure and poor pharmacokinetic properties of RSV inhibitors in the prior art, and to provide a benzoselenazepine Compounds and their preparation methods and uses. These compounds have good RSV inhibitory activity and good in vitro and in vivo pharmacokinetic properties.
  • the present invention provides a benzoselenazepine as shown in formula I a compound or a pharmaceutically acceptable salt thereof,
  • R 1 , R 2 , R 3 and R 4 are independently hydrogen or deuterium
  • R 5 is hydrogen, halogen, C 1-6 alkyl, or C 1-6 alkyl substituted by one or more Ra ;
  • R a is independently deuterium, halogen or hydroxy
  • R 6 is hydrogen, —C( ⁇ O)C 1-6 alkyl, —C( ⁇ O)OC 1-6 alkyl, —C( ⁇ O)C 1-6 alkyl substituted by 1 to 3 halogens, or —C( ⁇ O)OC 1-6 alkyl substituted by 1 to 3 halogens.
  • the halogen is independently fluorine, chlorine, bromine or iodine, such as fluorine.
  • the C 1-6 alkyl group and the C 1-6 alkyl group substituted by one or more Ra are independently C 1-4 alkyl groups, such as methyl.
  • the halogen in the -C( ⁇ O)C 1-6 alkyl substituted by 1 to 3 halogens and the -C( ⁇ O)OC 1-6 alkyl substituted by 1 to 3 halogens is independently fluorine, chlorine, bromine or iodine, such as fluorine.
  • R 1 , R 2 , R 3 and R 4 are independently hydrogen.
  • R 5 is C 1-6 alkyl.
  • R 6 is hydrogen, —C( ⁇ O)OC 1-6 alkyl, or —C ( ⁇ O)C 1-6 alkyl substituted by 1 to 3 halogens.
  • R 5 is hydrogen, halogen, methyl, difluoromethyl, trifluoromethyl, hydroxymethyl, or methyl substituted with 1 to 3 deuteriums.
  • R5 is methyl, -CD3 , -F, -Cl, -Br, -I, -CF3 , -CF2H , or -CH2OH .
  • R 5 is methyl
  • the benzoselenazepine shown in Formula I is any of the following compounds:
  • the present invention provides a pharmaceutical composition
  • a pharmaceutical composition comprising the benzoselenazepine as shown in formula I as described above.
  • the selection of the pharmaceutical excipients varies depending on the route of administration and the characteristics of the action, and can generally be fillers, diluents, binders, wetting agents, disintegrants, lubricants, emulsifiers, suspending agents, etc. conventional in the art.
  • the pharmaceutical composition is prepared by adding the benzoselenazepine of formula I
  • the compounds are prepared with one or more pharmaceutical excipients into dosage forms suitable for human or animal use, such as tablets, coated tablets, dragees, suppositories, hard and soft gelatin capsules, solutions, emulsions or suspensions.
  • the benzoselenazepine shown in Formula I is administered to the subject by an enteral or parenteral route, such as oral administration, intravenous injection, intramuscular injection, subcutaneous injection or rectal administration.
  • the present invention also provides a benzoselenazepine as shown in formula I Use of a compound or a pharmaceutically acceptable salt thereof, or the pharmaceutical composition as described above, in the preparation of a drug for treating or preventing RSV infection.
  • the present invention also provides a benzoselenazepine as shown in formula I as described above.
  • the preparation method of the compound comprises the following steps: in an organic solvent, in the presence of an acidic reagent, subjecting a compound as shown in Formula II to a substitution reaction as shown below with a benzopyrimidine compound as shown in Formula III to obtain the benzoselenazepine compound as shown in Formula I.
  • R 6 is hydrogen, -C( ⁇ O)C 1-6 alkyl, -C( ⁇ O)OC 1-6 alkyl, -C( ⁇ O)C 1-6 alkyl substituted by 1 to 3 halogens, or -C( ⁇ O)OC 1-6 alkyl substituted by 1 to 3 halogens; and R 1 , R 2 , R 3 , R 4 and R 5 are as defined above.
  • the operations and conditions in the method 1 can be conventional operations and conditions in this type of reaction in the art. Specifically, they are as follows:
  • the substitution reaction can be carried out under gas protection, which can be nitrogen and/or argon.
  • the organic solvent may be an alcohol solvent, such as ethanol, isopropanol or n-butanol, for example ethanol.
  • the acidic reagent may be ammonium chloride.
  • the molar ratio of the benzopyrimidine compound represented by Formula III to the compound represented by Formula II may be 1:(1-2), for example, 1:1.2 or 1:1.3.
  • the molar ratio of the acidic reagent to the benzopyrimidine compound represented by Formula III may be (0.02-1):1, for example, 0.05:1 or 0.1:1.
  • the reaction temperature of the substitution reaction may be 50-100°C, for example 80°C.
  • the progress of the substitution reaction can be monitored by conventional monitoring methods in the art (eg, TLC, HPLC, or NMR).
  • the reaction endpoint is generally taken as the disappearance or no-reaction of the compound III, for example, 12-16 hours.
  • the present invention provides a compound as shown in Formula II,
  • R 1 , R 2 , R 3 and R 4 are as defined above.
  • the present invention provides a method for preparing a compound represented by Formula IIa, comprising the following steps:
  • Step 1 substitution reaction: In the presence of a base and a catalyst, phenylselenol undergoes a nucleophilic substitution reaction with (2-bromoethyl)benzylcarbamate to produce intermediate II-1;
  • Step 2 (cyclization reaction): In the presence of an acid, intermediate II-1 undergoes a cyclization reaction with paraformaldehyde to obtain intermediate II-2;
  • Step 3 (Cbz protection removal): Intermediate II-2 is hydrolyzed with acid or subjected to reductive hydrogenation to remove the Cbz protecting group to obtain benzoselenazepine Intermediate IIa.
  • step 1, step 2 and step 3 may be conventional operations and conditions for such reactions in the art.
  • the base is sodium hydroxide, potassium hydroxide, potassium tert-butoxide, sodium hydride, sodium carbonate, potassium carbonate, cesium carbonate, etc., preferably potassium carbonate.
  • the catalyst in step 1, is sodium iodide, potassium iodide, tetrabutylammonium iodide, tetrabutylammonium bromide, triethylammonium benzyl bromide or a crown ether (such as 18-crown-6), etc., preferably sodium iodide.
  • the acid in step 2, is a hydrohalic acid (such as hydrochloric acid), sulfuric acid, phosphoric acid, trifluoroacetic acid, methanesulfonic acid, trifluoromethanesulfonic acid, perfluorosulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, etc., preferably p-toluenesulfonic acid.
  • hydrohalic acid such as hydrochloric acid
  • sulfuric acid sulfuric acid
  • phosphoric acid trifluoroacetic acid
  • methanesulfonic acid trifluoromethanesulfonic acid
  • perfluorosulfonic acid perfluorosulfonic acid
  • benzenesulfonic acid p-toluenesulfonic acid, etc., preferably p-toluenesulfonic acid.
  • the acid in step 3, is a hydrohalic acid, preferably a hydrobromic acid-acetic acid solution.
  • the catalyst in step 3, when reductive hydrogenation is used to remove the Cbz protecting group, is palladium carbon, palladium hydroxide, platinum carbon or Raney nickel, and preferably 1-5% palladium carbon.
  • the present invention also provides the following compounds:
  • pharmaceutically acceptable means that salts, solvents, excipients, etc. are generally non-toxic, safe, and suitable for use by patients.
  • the "patient” is preferably a mammal, more preferably a human.
  • pharmaceutically acceptable salt refers to a salt prepared from a compound of the present invention with a relatively non-toxic, pharmaceutically acceptable acid or base.
  • a base addition salt can be obtained by contacting the prototype of such compound with a sufficient amount of a pharmaceutically acceptable base in a suitable inert solvent.
  • Pharmaceutically acceptable base addition salts include, but are not limited to, lithium salts, sodium salts, potassium salts, calcium salts, aluminum salts, magnesium salts, zinc salts, bismuth salts, ammonium salts, and diethanolamine salts.
  • an acid addition salt can be obtained by contacting the prototype of such compound with a sufficient amount of a pharmaceutically acceptable acid in a suitable inert solvent.
  • the pharmaceutically acceptable acid includes inorganic acids, including, but not limited to, hydrochloric acid, hydrobromic acid, hydroiodic acid, nitric acid, carbonic acid, phosphoric acid, phosphorous acid, sulfuric acid, and the like.
  • the pharmaceutically acceptable acid includes organic acids, including but not limited to acetic acid, propionic acid, oxalic acid, isobutyric acid, maleic acid, malonic acid, benzoic acid, succinic acid, suberic acid, fumaric acid, lactic acid, mandelic acid, phthalic acid, benzenesulfonic acid, p-toluenesulfonic acid, citric acid, salicylic acid, tartaric acid, methanesulfonic acid, isonicotinic acid, acid citric acid, oleic acid, tannic acid, pantothenic acid, bitartrate, ascorbic acid, gentisic acid, fumaric acid, gluconic acid, sugar acid, formic acid, ethanesulfonic acid, pamoic acid (i.e., 4,4'-methylene-bis(3-hydroxy-2-naphthoic acid)), amino acids (e.g., glutamic acid, arginine), etc
  • the compounds of the present invention When the compounds of the present invention contain relatively acidic and relatively basic functional groups, they can be converted into base addition salts or acid addition salts.
  • base addition salts For details, see Berge et al., "Pharmaceutical Salts", Journal of Pharmaceutical Science 66:1-19 (1977), or Handbook of Pha rmaceutical Salts: Properties, Selection, and Use (P. Heinrich Stahl and Camille G. Wermuth, ed., Wiley-VCH, 2002).
  • treatment refers to therapeutic treatment.
  • treatment means: (1) alleviating the disease or one or more biological manifestations of the condition, (2) interfering with one or more points in the biological cascade that leads to or causes the condition, or one or more biological manifestations of the condition, (3) ameliorating one or more symptoms, effects, or side effects associated with the condition, or one or more symptoms, effects, or side effects associated with the condition or its treatment, or (4) slowing the progression of the condition or one or more biological manifestations of the condition.
  • terapéuticaally effective amount refers to an amount of a compound that, when administered to a patient, is sufficient to effectively treat a disease or condition described herein.
  • the “therapeutically effective amount” will vary depending on the compound, the condition and its severity, and the age of the patient to be treated, and can be adjusted as needed by those skilled in the art.
  • the reagents and raw materials used in the present invention are commercially available.
  • the positive progress of the present invention is that compared with the clinically investigated RSV inhibitor ziresovir, the compound of the present invention has stronger inhibitory activity against respiratory syncytial virus (RSV) and better in vitro and in vivo pharmacokinetic properties. Therefore, the present invention has very good prospects for preparing drugs for treating diseases related to respiratory syncytial virus (RSV) infection.
  • RSV respiratory syncytial virus
  • II-2 (20 g, 57.75 mmol) obtained in the previous step and 5% palladium on carbon (6.2 g, 2.89 mmol) were dissolved in tetrahydrofuran (150 mL) and reacted at room temperature under a hydrogen atmosphere for 5 hours. After completion, the reaction was filtered and the filtrate was concentrated under reduced pressure to yield the title compound IIa (11.5 g).
  • Example 6 N-((3-aminooxetan-3-yl)methyl)-2-(2,3-dihydrobenzo[f][1,4]selenazepine -4(5H)-yl)-6-methylquinazoline-4-amino (I-2) and 4-(((2-(2,3-dihydrobenzo[f][1,4]selenazepine Synthesis of 4-(5H)-6-methylquinazolin-4-yl)amino)methyl)-4-(hydroxymethyl)oxazolin-2-one (I-3)
  • 96-well plates were seeded at a density of 6 ⁇ 10 3 cells per well in Dulbecco's modified Eagle's medium (DMEM) containing 10% fetal bovine serum (FBS). The next day, cells were infected with sufficient RSV LongStrain (ATCC) to produce approximately 80-90% cytopathic effects after 6 days in the presence of serial half-log dilutions of the compounds in a total volume of 200 ⁇ L per well. After 6 days, cell viability was determined using a Cell Counting Kit-8. The absorbance at 450 nm and the reference value at 630 nm were measured to determine the 50% effective concentration (EC 50 ).
  • DMEM Dulbecco's modified Eagle's medium
  • FBS fetal bovine serum
  • Raw material Human liver microsomes (supplier: Corning, Cat No. 452117, containing approximately 45 mg of liver microsome protein per gram of liver)
  • each plate was centrifuged at 4000 rpm and 4°C for 20 minutes.
  • Caco-2 cells source American type culture collection (ATCC).
  • the transport buffer used in this study was HBSS containing 10.0 mM HEPES, pH 7.40 ⁇ 0.05. Bidirectional transport experiments were performed at a concentration of 2.00 ⁇ M for the test compound, with duplicates per group. Digoxin was tested at a concentration of 10.0 ⁇ M for bidirectional transport, with duplicates per group. Both propranolol and metoprolol were tested at a concentration of 2.00 ⁇ M in the A-to-B direction. The final DMSO concentration was controlled to less than 1%. The samples were incubated for 2 hours in a CO2 incubator at 37.0°C, 5% CO2 , and high humidity (no shaking).
  • test compound and control compound in the starting, donor, and receiver solutions were determined by LC-MS/MS, and quantification was performed using the peak area ratio of the test compound to the internal standard. After the transport experiment, the integrity of the Caco-2 cell monolayer was assessed using a lucifer yellow exclusion assay.
  • dCr /dt represents the cumulative concentration change rate of the receiving side over time
  • Vr is the volume of the solution in the receiving chamber (0.0750 mL for the apical side and 0.250 mL for the basolateral side)
  • A is the surface area of transmission (the monolayer cell area is 0.143 cm2 );
  • C0 is the initial concentration on the administration side.
  • % Solution Recovery 100 ⁇ [(V r ⁇ C r ) + (V d ⁇ C d )] / (V d ⁇ C 0 );
  • Vd represents the volume of the solution in the dosing chamber (0.0750 mL on the apical side and 0.250 mL on the basal side);
  • Cd and Cr are the concentrations of the compound in the donating chamber (donor) and the receiving chamber (receiver) at the end of the experiment, respectively.
  • 0.2 ml of blood was collected from the rat jugular vein at 0.033 h, 0.25 h, 0.5 h, 1 h, 2 h, 4 h, 8 h and 24 h after administration, anticoagulated with EDTA-K2, and placed on ice.
  • 0.2 ml of blood was collected from the rat jugular vein at 0.25 h, 0.5 h, 1 h, 2 h, 4 h, 6 h, 8 h and 24 h after administration, anticoagulated with EDTA-K2, and placed on ice after collection.
  • the pharmacokinetic parameters were calculated using the non-compartmental model using Phoenix WinNonlin 7.0 software using the plasma drug concentration data at different time points, providing parameters such as AUC 0-int , C max , T max , T 1/2 , and oral bioavailability (F%). The results are shown in Table 9 below.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Virology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

La présente invention concerne des composés benzosélénazoles, leur procédé de préparation et leur utilisation. Plus particulièrement, la présente invention concerne des composés benzosélénazoles représentés par la formule I ou des sels pharmaceutiquement acceptables de ceux-ci. Les composés benzosélénazoles ont une bonne activité inhibitrice du VRS et de bonnes propriétés pharmacocinétiques in vivo et in vivo.
PCT/CN2025/081112 2024-03-13 2025-03-06 Composés benzosélénazoles ainsi que leur procédé de préparation et leur utilisation Pending WO2025190151A1 (fr)

Applications Claiming Priority (2)

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CN202410287668 2024-03-13
CN202410287668.2 2024-03-13

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WO2025190151A1 true WO2025190151A1 (fr) 2025-09-18

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