HRP20231564T1 - Spojevi za ublažavanje boli - Google Patents

Spojevi za ublažavanje boli Download PDF

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HRP20231564T1
HRP20231564T1 HRP20231564TT HRP20231564T HRP20231564T1 HR P20231564 T1 HRP20231564 T1 HR P20231564T1 HR P20231564T T HRP20231564T T HR P20231564TT HR P20231564 T HRP20231564 T HR P20231564T HR P20231564 T1 HRP20231564 T1 HR P20231564T1
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chemical structure
following chemical
pain
compound
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HRP20231564TT
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Nicolas Bazan
Hernan Bazan
Julio Alvarez-Builla
Dennis Paul
Carolina BURGOS
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The Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical College
University Of Alcala De Henares
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Publication of HRP20231564T1 publication Critical patent/HRP20231564T1/hr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
    • C07C311/19—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
    • C07C311/51—Y being a hydrogen or a carbon atom
    • 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
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A61K31/18—Sulfonamides
    • 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
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • 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
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • 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
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4402—Non condensed pyridines; Hydrogenated derivatives thereof only substituted in position 2, e.g. pheniramine, bisacodyl
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P23/00—Anaesthetics
    • 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
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
    • C07D213/40—Acylated substituent nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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 carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
    • C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/192—Radicals derived from carboxylic acids from aromatic carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Anesthesiology (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Medicinal Preparation (AREA)
  • Medicines Containing Material From Animals Or Micro-Organisms (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pyridine Compounds (AREA)

Claims (13)

1. Analgetski spoj formule (I): [image] gdje R sadrži NH2, N(CH3)2, NHCH3, N(CH2CH3)2, N(CH2CH2)2NCH2C6H5, NH(CH2)2C6H5, NHCH2C6H5, N(CH2CH2)2O, NHCH2CH2CH2CH3, NHCH2C6H4CH3, NHCH2C6H3Cl2, NHCH2C6H5CH3, NHCH2C6H5Cl, NHCH2C6H5NO2, NHC5H9, NHCH2C(CH3)2, NHC(CH3)2, NHCH2CH2C6H3(OH)2, NHCH2C6H4N, NHCH2C6H3NCH3, NHCH2CH2C4H4N, N(CH3)CH2CH2OH, NHCH2CH(OH)CH2NH2; ili njihova farmaceutski prihvatljiva sol.
2. Analgetski spoj formule (II): [image] gdje je R1 H, OH, alkilna skupina, haloalkilna skupina, halobenzilna skupina, fenilna skupina, -O-(alkil), -O-(haloalkil), -O-(halobenzil), -O-(fenil), alkil fenil, haloalkil-fenil, alkil-halobenzen, alkil-nitrobenzen, -O-(alkil fenil), -O-(haloalkil)-fenil, cikloalkanska skupina, i gdje je R2 odabran iz skupine koja se sastoji od H i alkilne skupine; ili njegova farmaceutski prihvatljiva sol.
3. Analgetski spoj formule (II): [image] gdje R1 sadrži H, CH3, (CH2)2C6H5, CH2C6H5, CH2CH2CH2CH3, CH2C6H3Cl2, CH2C6H5CH3, CH2C6H5Cl, CH2C6H5NO2, C5H9, CH2C(CH3)2, C(CH3)2, CH2CH2C6H3(OH)2, CH2C6H4N, CH2C6H3NCH3,CH2CH2C4H4N, CH2CH2OH, ili CH2CH(OH)CH2NH2; i gdje je R2 odabran iz skupine koju čine H i CH3; ili njegova farmaceutski prihvatljiva sol.
4. Analgetski spoj sukladno patentnom zahtjevu 2, naznačen time, da alkil sadrži CNH2N-1, i po izboru, gdje je N 1-10.
5. Analgetski spoj sukladno patentnom zahtjevu 1, 2 ili 3, koji ima sljedeću kemijsku strukturu: [image] ili ima sljedeću kemijsku strukturu: [image] ili ima sljedeću kemijsku strukturu: [image] ili ima sljedeću kemijsku strukturu: [image] ili ima sljedeću kemijsku strukturu: [image] ili ima sljedeću kemijsku strukturu: [image] ili ima sljedeću kemijsku strukturu: [image] ili ima sljedeću kemijsku strukturu: [image] ili ima sljedeću kemijsku strukturu: [image] ili ima sljedeću kemijsku strukturu: [image] ili ima sljedeću kemijsku strukturu: [image] ili ima sljedeću kemijsku strukturu: [image] ili ima sljedeću kemijsku strukturu: [image] ili ima sljedeću kemijsku strukturu: [image] ili ima sljedeću kemijsku strukturu: [image] ili ima sljedeću kemijsku strukturu: [image] ili ima sljedeću kemijsku strukturu: [image] ili ima sljedeću kemijsku strukturu: [image] ili ima sljedeću kemijsku strukturu: [image] ili ima sljedeću kemijsku strukturu: [image] ili ima sljedeću kemijsku strukturu: [image] ili ima sljedeću kemijsku strukturu: [image] ili ima sljedeću kemijsku strukturu: [image]
6. Analgetski spoj sukladno bilo kojem od zahtjeva 1 do 5, naznačen time, da se koristi za ublažavanje boli, prevenciju boli, ublažavanje boli, smanjenje učestalosti boli, odgađanje razvoja boli, sprječavanje razvoja boli ili ublažavanje boli kod subjekta.
7. Analgetski spoj za upotrebu sukladno zahtjevu 6, naznačen time što bol uključuje neuropatsku bol, nociceptivnu bol ili njihovu kombinaciju, i izborno pri čemu neuropatska bol uključuje post-kiruršku bol, neuropatsku bol, zubnu bol, oftalmološku bol, artritičnu bol, post- i/ili traumatska bol, ili njihova kombinacija.
8. Analgetski spoj za upotrebu sukladno zahtjevu 6, naznačen time što je spoj namijenjen da se daje u terapeutski učinkovitoj količini i pri čemu terapeutski učinkovita količina sadrži dozu od oko 10 uM do oko 10 mM; i izborno gdje terapeutski učinkovita količina sadrži dozu od oko 50 uM do oko 1 uM.
9. Analgetski spoj za upotrebu sukladno zahtjevu 6, naznačen time, da se spoj daje u jednoj dozi; ili pri čemu spoj se daje u intervalima od oko 4 sata, 12 sati ili 24 sata.
10. Analgetski spoj za upotrebu sukladno zahtjevu 6, naznačen time, da se spoj primjenjuje oralno, parenteralno, transdermalno ili nazalno; ili gdje se pripravak primjenjuje u obliku pilule, kapsule, kreme, spreja, losiona ili vodene otopine.
11. Analgetski spoj za upotrebu sukladno zahtjevu 6, naznačen time, da je namjera da se primjenjuje opioid i/ili NSAID istodobno ili nakon subjekta.
12. Analgetski spoj za upotrebu sukladno zahtjevu 6, naznačen time, da se spoj ne metabolizira u NAPQI.
13. Medicinski pribor za liječenje boli, komplet koji sadrži: tiskane upute za davanje spoja subjektu koji pati od boli; i analgetski spoj prema bilo kojem od zahtjeva 1-5.
HRP20231564TT 2017-08-25 2018-03-12 Spojevi za ublažavanje boli HRP20231564T1 (hr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201762550137P 2017-08-25 2017-08-25
EP18847873.9A EP3672938B1 (en) 2017-08-25 2018-03-12 Compounds for ameliorating pain
PCT/US2018/022029 WO2019040122A1 (en) 2017-08-25 2018-03-12 COMPOSITIONS AND METHODS FOR ALLEVIATING PAIN

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JP (1) JP7116792B2 (hr)
KR (1) KR102584483B1 (hr)
CN (1) CN111278805B (hr)
AU (1) AU2018319549C1 (hr)
BR (1) BR112020003705B1 (hr)
CA (1) CA3073801C (hr)
ES (1) ES2965542T3 (hr)
HR (1) HRP20231564T1 (hr)
MX (1) MX2020002147A (hr)
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HRP20231564T1 (hr) * 2017-08-25 2024-03-29 The Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical College Spojevi za ublažavanje boli
WO2021211681A1 (en) * 2020-04-15 2021-10-21 Neumentum, Inc. Compositions and methods for treating pain and/or inflammation

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HRP20231564T1 (hr) * 2017-08-25 2024-03-29 The Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical College Spojevi za ublažavanje boli
CN108299255B (zh) * 2018-02-11 2020-05-19 山东大学 组蛋白去乙酰化酶8选择性抑制剂及其制备方法和应用

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US20200230087A1 (en) 2020-07-23
EP3672938B1 (en) 2023-11-01
EP3672938A1 (en) 2020-07-01
RU2020110222A3 (hr) 2021-09-27
AU2018319549B2 (en) 2023-03-16
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US11529355B2 (en) 2022-12-20
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EP3672938C0 (en) 2023-11-01
KR20200058385A (ko) 2020-05-27
US11458142B2 (en) 2022-10-04
US20200179393A1 (en) 2020-06-11
CN111278805B (zh) 2023-04-18
RU2020110222A (ru) 2021-09-27
US20210379075A1 (en) 2021-12-09
EP3672938A4 (en) 2021-04-21
BR112020003705A2 (pt) 2020-11-17
RS65171B1 (sr) 2024-03-29
WO2019040122A1 (en) 2019-02-28
CN111278805A (zh) 2020-06-12
US11007199B2 (en) 2021-05-18
AU2018319549C1 (en) 2023-06-15
BR112020003705B1 (pt) 2023-02-28
ES2965542T3 (es) 2024-04-15
KR102584483B1 (ko) 2023-10-05
JP2020533402A (ja) 2020-11-19
CA3073801A1 (en) 2019-02-28

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