WO2022237710A1 - Forme cristalline d'un composé destiné au traitement de la grippe et son application - Google Patents
Forme cristalline d'un composé destiné au traitement de la grippe et son application Download PDFInfo
- Publication number
- WO2022237710A1 WO2022237710A1 PCT/CN2022/091605 CN2022091605W WO2022237710A1 WO 2022237710 A1 WO2022237710 A1 WO 2022237710A1 CN 2022091605 W CN2022091605 W CN 2022091605W WO 2022237710 A1 WO2022237710 A1 WO 2022237710A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- crystal form
- compound
- solvent
- xrpd
- xrpd characteristic
- Prior art date
Links
- 239000013078 crystal Substances 0.000 title claims abstract description 127
- 150000001875 compounds Chemical class 0.000 title claims abstract description 59
- 206010022000 influenza Diseases 0.000 title claims abstract description 17
- 238000000634 powder X-ray diffraction Methods 0.000 claims abstract description 67
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 50
- 229940126062 Compound A Drugs 0.000 claims description 45
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims description 45
- 239000002904 solvent Substances 0.000 claims description 44
- 238000000034 method Methods 0.000 claims description 35
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 32
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 29
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 24
- 241000712461 unidentified influenza virus Species 0.000 claims description 24
- 239000008194 pharmaceutical composition Substances 0.000 claims description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 17
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 17
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 14
- 238000002425 crystallisation Methods 0.000 claims description 14
- 230000008025 crystallization Effects 0.000 claims description 14
- 239000000243 solution Substances 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 239000012046 mixed solvent Substances 0.000 claims description 11
- 239000000047 product Substances 0.000 claims description 11
- 239000003814 drug Substances 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 10
- 230000000694 effects Effects 0.000 claims description 9
- 239000012043 crude product Substances 0.000 claims description 7
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 238000001816 cooling Methods 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 230000002401 inhibitory effect Effects 0.000 claims description 6
- 238000002844 melting Methods 0.000 claims description 6
- 230000008018 melting Effects 0.000 claims description 6
- 229940011051 isopropyl acetate Drugs 0.000 claims description 5
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 5
- 238000001953 recrystallisation Methods 0.000 claims description 5
- 238000010992 reflux Methods 0.000 claims description 5
- 238000000338 in vitro Methods 0.000 claims description 4
- 238000004821 distillation Methods 0.000 claims description 3
- 239000011259 mixed solution Substances 0.000 claims description 3
- 238000001228 spectrum Methods 0.000 claims description 3
- -1 n-heptyl alkanes Chemical class 0.000 claims 1
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 17
- 238000002474 experimental method Methods 0.000 description 15
- 238000011282 treatment Methods 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 208000024891 symptom Diseases 0.000 description 11
- FIDLLEYNNRGVFR-CTNGQTDRSA-N (3R)-2-[(11S)-7,8-difluoro-6,11-dihydrobenzo[c][1]benzothiepin-11-yl]-11-hydroxy-5-oxa-1,2,8-triazatricyclo[8.4.0.03,8]tetradeca-10,13-diene-9,12-dione Chemical compound OC1=C2N(C=CC1=O)N([C@@H]1COCCN1C2=O)[C@@H]1C2=C(SCC3=C1C=CC(F)=C3F)C=CC=C2 FIDLLEYNNRGVFR-CTNGQTDRSA-N 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- 241000282339 Mustela Species 0.000 description 9
- 239000003981 vehicle Substances 0.000 description 9
- 241000700605 Viruses Species 0.000 description 8
- 201000010099 disease Diseases 0.000 description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 8
- 238000004128 high performance liquid chromatography Methods 0.000 description 8
- 238000002411 thermogravimetry Methods 0.000 description 8
- 238000000113 differential scanning calorimetry Methods 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 241000282341 Mustela putorius furo Species 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 206010041232 sneezing Diseases 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 230000003247 decreasing effect Effects 0.000 description 5
- 238000001514 detection method Methods 0.000 description 5
- 239000012530 fluid Substances 0.000 description 5
- 210000003928 nasal cavity Anatomy 0.000 description 5
- 238000013341 scale-up Methods 0.000 description 5
- 230000028327 secretion Effects 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 229940123734 Endonuclease inhibitor Drugs 0.000 description 4
- 241000712431 Influenza A virus Species 0.000 description 4
- 206010024264 Lethargy Diseases 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 239000012296 anti-solvent Substances 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- 230000001419 dependent effect Effects 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 208000015181 infectious disease Diseases 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 230000009385 viral infection Effects 0.000 description 4
- 208000031648 Body Weight Changes Diseases 0.000 description 3
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 description 3
- 230000000840 anti-viral effect Effects 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- 230000004579 body weight change Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000000227 grinding Methods 0.000 description 3
- 208000037797 influenza A Diseases 0.000 description 3
- 208000037798 influenza B Diseases 0.000 description 3
- 230000000670 limiting effect Effects 0.000 description 3
- 238000000691 measurement method Methods 0.000 description 3
- 238000004806 packaging method and process Methods 0.000 description 3
- JLFNLZLINWHATN-UHFFFAOYSA-N pentaethylene glycol Chemical compound OCCOCCOCCOCCOCCO JLFNLZLINWHATN-UHFFFAOYSA-N 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 230000010076 replication Effects 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 229940124597 therapeutic agent Drugs 0.000 description 3
- 230000029812 viral genome replication Effects 0.000 description 3
- 239000005723 virus inoculator Substances 0.000 description 3
- 206010059866 Drug resistance Diseases 0.000 description 2
- 102100031780 Endonuclease Human genes 0.000 description 2
- 108010042407 Endonucleases Proteins 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- RZVPBGBYGMDSBG-GGAORHGYSA-N baloxavir marboxil Chemical compound COC(=O)OCOc1c2C(=O)N3CCOC[C@H]3N([C@H]3c4ccc(F)c(F)c4CSc4ccccc34)n2ccc1=O RZVPBGBYGMDSBG-GGAORHGYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 229940042406 direct acting antivirals neuraminidase inhibitors Drugs 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 208000037799 influenza C Diseases 0.000 description 2
- 229940126181 ion channel inhibitor Drugs 0.000 description 2
- 108020004999 messenger RNA Proteins 0.000 description 2
- 238000002953 preparative HPLC Methods 0.000 description 2
- 230000000069 prophylactic effect Effects 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000002911 sialidase inhibitor Substances 0.000 description 2
- 238000010583 slow cooling Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- 230000004584 weight gain Effects 0.000 description 2
- 235000019786 weight gain Nutrition 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- 108091032973 (ribonucleotides)n+m Proteins 0.000 description 1
- 102000040650 (ribonucleotides)n+m Human genes 0.000 description 1
- JVKUCNQGESRUCL-UHFFFAOYSA-N 2-Hydroxyethyl 12-hydroxyoctadecanoate Chemical compound CCCCCCC(O)CCCCCCCCCCC(=O)OCCO JVKUCNQGESRUCL-UHFFFAOYSA-N 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 206010061818 Disease progression Diseases 0.000 description 1
- 241000283086 Equidae Species 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 241000713297 Influenza C virus Species 0.000 description 1
- 241001500351 Influenzavirus A Species 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241000282338 Mustela putorius Species 0.000 description 1
- 241000712464 Orthomyxoviridae Species 0.000 description 1
- 108091005804 Peptidases Proteins 0.000 description 1
- 241000288906 Primates Species 0.000 description 1
- 239000004365 Protease Substances 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 description 1
- 206010039101 Rhinorrhoea Diseases 0.000 description 1
- 241000283984 Rodentia Species 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229920001304 Solutol HS 15 Polymers 0.000 description 1
- 108020000999 Viral RNA Proteins 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 238000004164 analytical calibration Methods 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000002924 anti-infective effect Effects 0.000 description 1
- 239000003443 antiviral agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229940008411 baloxavir marboxil Drugs 0.000 description 1
- 208000013404 behavioral symptom Diseases 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 230000034994 death Effects 0.000 description 1
- 231100000517 death Toxicity 0.000 description 1
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 1
- 230000005750 disease progression Effects 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000009459 flexible packaging Methods 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 238000003304 gavage Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229960003971 influenza vaccine Drugs 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 238000011201 multiple comparisons test Methods 0.000 description 1
- 208000010753 nasal discharge Diseases 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000001543 one-way ANOVA Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 230000001932 seasonal effect Effects 0.000 description 1
- 238000000373 single-crystal X-ray diffraction data Methods 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000008685 targeting Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
- 238000001757 thermogravimetry curve Methods 0.000 description 1
- 238000013518 transcription Methods 0.000 description 1
- 230000035897 transcription Effects 0.000 description 1
- 238000007492 two-way ANOVA Methods 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
Images
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
- A61K31/53—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with three nitrogens as the only ring hetero atoms, e.g. chlorazanil, melamine
-
- 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
- A61K31/5383—1,4-Oxazines, e.g. morpholine ortho- or peri-condensed with heterocyclic ring systems
-
- 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
- A61P31/16—Antivirals for RNA viruses for influenza or rhinoviruses
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Pulmonology (AREA)
- Molecular Biology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
L'invention concerne le domaine de la biomédecine et, plus précisément, la forme cristalline d'un composé et son application. Le composé est le composé tel que représenté dans la formule A, et la forme cristalline présente un pic caractéristique de diffraction des rayons X sur poudre avec 2θ correspondant à 10,7 ± 0,2, 13,1 ± 0,2, 15,6 ± 0,2, 16,0 ± 0,2, 17,5 ± 0,2, 20,1 ± 0,2, 21,9 ± 0,2, 24,1 ± 0,2, 26,5 ± 0,2 et 29,7 ± 0,2. La forme cristalline du composé fournie peut être utilisée pour traiter la grippe.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202280006852.4A CN116829153A (zh) | 2021-05-10 | 2022-05-09 | 治疗流感化合物的晶型及应用 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110507480.0 | 2021-05-10 | ||
| CN202110507480 | 2021-05-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2022237710A1 true WO2022237710A1 (fr) | 2022-11-17 |
Family
ID=84028828
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/CN2022/091605 WO2022237710A1 (fr) | 2021-05-10 | 2022-05-09 | Forme cristalline d'un composé destiné au traitement de la grippe et son application |
Country Status (3)
| Country | Link |
|---|---|
| CN (1) | CN116829153A (fr) |
| TW (1) | TW202308646A (fr) |
| WO (1) | WO2022237710A1 (fr) |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103228653A (zh) * | 2010-09-24 | 2013-07-31 | 盐野义制药株式会社 | 被取代的多环性氨基甲酰基吡啶酮衍生物的前药 |
| WO2018030463A1 (fr) * | 2016-08-10 | 2018-02-15 | 塩野義製薬株式会社 | Dérivé de pyridone polycyclique substitué et composition pharmaceutique contenant un promédicament de celui-ci |
| US20180118760A1 (en) * | 2015-04-28 | 2018-05-03 | Shionogi & Co., Ltd. | Substituted polycyclic pyridone derivatives and prodrugs thereof |
| CN108697715A (zh) * | 2015-12-15 | 2018-10-23 | 盐野义制药株式会社 | 包含帽依赖性核酸内切酶抑制剂及抗流感药的组合的流感治疗用药物 |
| CN109721615A (zh) * | 2017-09-18 | 2019-05-07 | 广东东阳光药业有限公司 | 流感病毒复制抑制剂及其用途 |
| WO2021007506A1 (fr) * | 2019-07-11 | 2021-01-14 | Nanjing Zhengxiang Pharmaceuticals Co., Ltd. | Composés s'utilisant pour traiter les infections causées par le virus de la grippe |
-
2022
- 2022-05-09 TW TW111117314A patent/TW202308646A/zh unknown
- 2022-05-09 CN CN202280006852.4A patent/CN116829153A/zh active Pending
- 2022-05-09 WO PCT/CN2022/091605 patent/WO2022237710A1/fr active Application Filing
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103228653A (zh) * | 2010-09-24 | 2013-07-31 | 盐野义制药株式会社 | 被取代的多环性氨基甲酰基吡啶酮衍生物的前药 |
| US20180118760A1 (en) * | 2015-04-28 | 2018-05-03 | Shionogi & Co., Ltd. | Substituted polycyclic pyridone derivatives and prodrugs thereof |
| CN108697715A (zh) * | 2015-12-15 | 2018-10-23 | 盐野义制药株式会社 | 包含帽依赖性核酸内切酶抑制剂及抗流感药的组合的流感治疗用药物 |
| WO2018030463A1 (fr) * | 2016-08-10 | 2018-02-15 | 塩野義製薬株式会社 | Dérivé de pyridone polycyclique substitué et composition pharmaceutique contenant un promédicament de celui-ci |
| CN109721615A (zh) * | 2017-09-18 | 2019-05-07 | 广东东阳光药业有限公司 | 流感病毒复制抑制剂及其用途 |
| WO2021007506A1 (fr) * | 2019-07-11 | 2021-01-14 | Nanjing Zhengxiang Pharmaceuticals Co., Ltd. | Composés s'utilisant pour traiter les infections causées par le virus de la grippe |
Also Published As
| Publication number | Publication date |
|---|---|
| CN116829153A (zh) | 2023-09-29 |
| TW202308646A (zh) | 2023-03-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP4846158B2 (ja) | Ｎ−［４−［２−（２−アミノ−４，７−ジヒドロ−４−オキソ−３Ｈ−ピロロ［２，３−ｄ］ピリミジン−５−イル）エチル］ベンゾイル］−Ｌ−グルタミン酸の新規結晶形およびその製造方法 | |
| US10155743B2 (en) | Glutarimide derivatives, use thereof, pharmaceutical composition based thereon and methods for producing glutarimide derivatives | |
| JP6026400B2 (ja) | （１ｓ，２ｓ，３ｓ，４ｒ）−３−［（１ｓ）−１−アセチルアミノ−２−エチル−ブチル］−４−グアニジノ−２−ヒドロキシ−シクロペンチル−１−カルボン酸水和物の製造方法 | |
| TW202320793A (zh) | 含有三嗪衍生物之醫藥組合物 | |
| US11154531B2 (en) | Compounds and pharmaceutical uses thereof | |
| AU2006315169A1 (en) | Compositions comprising lipoxygenase inhibitors and cyclodextrin | |
| WO2012011847A1 (fr) | Indoles substituées, composant antiviral actif, procédés de fabrication et d'utilisation | |
| KR102572035B1 (ko) | 무정형 형태의 빌란테롤 트리페나테이트 및 이의 제조방법 | |
| WO2022237710A1 (fr) | Forme cristalline d'un composé destiné au traitement de la grippe et son application | |
| EP3369816B1 (fr) | Composition contenant sous forme stable une molécule d'acide nucléique simple brin qui supprime l'expression du gène tgf-béta1 | |
| TW319765B (fr) | ||
| WO2023174400A1 (fr) | Sel de composé hétérocyclique nitrique à six chaînons amino substitué, forme cristalline de celui-ci, procédé de préparation correspondant et utilisation associée | |
| WO2019028689A1 (fr) | Forme cristalline d'odm-201, son procédé de préparation et composition pharmaceutique correspondante | |
| CN115626917B (zh) | 化合物的晶型及其组合物和用途 | |
| RU2780249C1 (ru) | Применение производного 1,3,5-триазин-2,4-диамина для ингибирования репликации бета-коронавирусов, включая sars-cov-2 | |
| US20230151034A1 (en) | Peptidomimetic n5-methyl-n2-(nonanoyl-l-leucyl)-l-glutaminate derivatives, triazaspiro[4.14]nonadecane derivatives and similar compounds as inhibitors of norovirus and coronavirus replication | |
| CN113980074A (zh) | N4-羟基胞苷的晶型a与制备方法和用途 | |
| JP2020519624A (ja) | Ｌ−オルニチンフェニルアセテートを製造する方法 | |
| JPH01156970A (ja) | イソプレニルアミン誘導体 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 22806675 Country of ref document: EP Kind code of ref document: A1 |
|
| WWE | Wipo information: entry into national phase |
Ref document number: 202280006852.4 Country of ref document: CN |
|
| NENP | Non-entry into the national phase |
Ref country code: DE |