HRP20240122T1 - Irak inhibitor i metoda njegove pripreme i upotrebe - Google Patents
Irak inhibitor i metoda njegove pripreme i upotrebe Download PDFInfo
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- HRP20240122T1 HRP20240122T1 HRP20240122TT HRP20240122T HRP20240122T1 HR P20240122 T1 HRP20240122 T1 HR P20240122T1 HR P20240122T T HRP20240122T T HR P20240122TT HR P20240122 T HRP20240122 T HR P20240122T HR P20240122 T1 HRP20240122 T1 HR P20240122T1
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- racemate
- tautomer
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- 238000002360 preparation method Methods 0.000 title claims 6
- 239000003112 inhibitor Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 22
- -1 1-ethylethenyl Chemical group 0.000 claims 19
- 150000003839 salts Chemical class 0.000 claims 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 8
- 125000001931 aliphatic group Chemical group 0.000 claims 6
- 238000006243 chemical reaction Methods 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- 239000003638 chemical reducing agent Substances 0.000 claims 5
- 125000006708 (C5-C14) heteroaryl group Chemical group 0.000 claims 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- 239000002253 acid Substances 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 229910003827 NRaRb Inorganic materials 0.000 claims 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
- 239000012279 sodium borohydride Substances 0.000 claims 2
- 229910000033 sodium borohydride Inorganic materials 0.000 claims 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims 1
- 125000006711 (C2-C12) alkynyl group Chemical group 0.000 claims 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 claims 1
- 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 claims 1
- 125000006039 1-hexenyl group Chemical group 0.000 claims 1
- 125000006021 1-methyl-2-propenyl group Chemical group 0.000 claims 1
- 125000006018 1-methyl-ethenyl group Chemical group 0.000 claims 1
- 125000006023 1-pentenyl group Chemical group 0.000 claims 1
- 125000006017 1-propenyl group Chemical group 0.000 claims 1
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 claims 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 claims 1
- 125000006020 2-methyl-1-propenyl group Chemical group 0.000 claims 1
- 125000006022 2-methyl-2-propenyl group Chemical group 0.000 claims 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims 1
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 claims 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 claims 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- 201000005569 Gout Diseases 0.000 claims 1
- 206010020751 Hypersensitivity Diseases 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- 208000001145 Metabolic Syndrome Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 206010040047 Sepsis Diseases 0.000 claims 1
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims 1
- 208000026935 allergic disease Diseases 0.000 claims 1
- 230000007815 allergy Effects 0.000 claims 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 208000010125 myocardial infarction Diseases 0.000 claims 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 239000000651 prodrug Substances 0.000 claims 1
- 229940002612 prodrug Drugs 0.000 claims 1
- 125000006233 propoxy propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000006225 propoxyethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- 125000005767 propoxymethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])[#8]C([H])([H])* 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000003554 tetrahydropyrrolyl group Chemical group 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- 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]
-
- 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
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
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- 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
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- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
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- Health & Medical Sciences (AREA)
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- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
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- Physical Education & Sports Medicine (AREA)
- Epidemiology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pulmonology (AREA)
- Pain & Pain Management (AREA)
- Immunology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Claims (10)
1. Spoj formule I ili njegov stereoizomer, racemat, tautomer, izotopski obilježeni spoj ili farmaceutski prihvatljiva sol,
[image]
pri čemu,
prsten A je 5-14 člani heteroaril ili 5-12 heterociklil koji sadrži najmanje jedan N;
R1, R2 i R3 su svaki neovisno odabrani između vodika, halogena, CN, OH i sljedećih skupina izborno supstituiranih s jednim, dva ili više R: (C1-C12)alifatski hidrokarbil, (C1-C12)alifatski hidrokarbil koji izborno sadrži jedan, dva ili više heteroatoma, C3-12 cikloalkil, 3-12 člani heterociklil, C6-20 aril ili 5-14 člani heteroaril, i -NRaRb;
W je odabran između O, S, NH i jednostruka je veza;
Ra i Rb su svaki neovisno odabrani između Hand (C1-C12)alifatskog hidrokarbila;
svaki R je neovisno odabran između halogena, CN, OH, SH, NRaRb i sljedećih grupa izborno supstituiranih s jednim, dva ili više R’: (C1-C12)alifatski hidrokarbil, (C1-C12)alifatski hidrokarbil koji izborno sadrži jedan, dva ili više heteroatoma, C3-12 cikloalkil, 3-12 člani heterociklil i C6-20 aril ili 5-14 člani heteroaril;
svaki R' je neovisno odabran između halogena, CN, OH, SH i NRaRb; i
n je odabran između 1, 2 i 3; i m je odabran između 1, 2, 3, 4, 5 i 6.
2. Spoj formule I ili njegov stereoizomer, racemat, tautomer, izotopski obilježeni spoj, ili farmaceutski prihvatljiva sol prema patentnom zahtjevu 1, pri čemu "(C1-C12)alifatski hidrokarbil koji izborno sadrži jedan, dva ili više heteroatoma" može se odabrati između (C1-C12)alifatski hidrokarbiloksi, (C1-C12)alifatski hidrokarbiltio, (C1-C6)alifatski hidrokarbiloksi(C1-C6)alifatski hidrokarbil, (C1-C6)alifatski hidrokarbiltio(C1-C6)alifatski hidrokarbil, N-(C1-C3)alifatski hidrokarbilamino(C1-C6)alifatski hidrokarbil, i N,N-di-(C1-C3)alifatski hidrokarbilamino(C1-C6)alifatski hidrokarbil;
"5-14 člani heteroaril ili 5-12 člani heterociklil koji sadrži najmanje jedan N" je odabran između piridina, pirola, piperidina i tetrahidropirola;
(C1-C12)alifatski hidrokarbil može biti odabran između (C1-C12)alkila, (C2-C12)alkenila i (C2-C12)alkinila, i poželjno, (C1-C12)alifatski hidrokarbil može biti odabran između (C1-C6)alkila, (C2-C6)alkenila i (C2-C6)alkinila;
"halogen" je odabran između F, Cl, Br i I; i
"C3-C12 cikloalkil" može biti odabran između ciklopropila, ciklobutila, ciklopentila i cikloheksila.
3. Spoj formule I ili njegov stereoizomer, racemat, tautomer, izotopski obilježeni spoj ili farmaceutski prihvatljiva sol prema patentnom zahtjevu 1 ili 2, pri čemu
svaki od R1, R2 i R3 može biti neovisno odabran iz sljedećih skupina izborno supstituiranih s jednim, dva ili više R: metil, etil, n-propil, izopropil, n-butil, izobutil, tert-butil, n-pentil, izopentil, neopentil, n-heksil, etenil, 1-propenil, 2-propenil, 1-metiletenil, 1-butenil, 1-etiletenil, 1-metil-2-propenil, 2-butenil, 3-butenil, 2-metil-1-propenil, 2-metil-2-propenil, 1-pentenil, 1-heksenil, etinil, 1-propinil, 2-propinil, 1-butinil, 1-metil-2-propinil, 3-butinil, 1-pentinil, 1-heksinil, ciklopropil, ciklobutil, ciklopentil, cikloheksil, metoksi, etoksil, propoksi, butoksi, pentiloksi, metoksimetil, etoksilmetil, propoksimetil, metoksietil, etoksiletil, propoksietil, metoksipropil, etoksilpropil, propoksipropil, N-metilaminometil, N-metilaminoetil, N-etilaminoetil, N,N-dimetilaminometil, N,N-dimetilaminoetil, N,N-dietilaminoetil, amino, N,N-dimetilamino, N,N-dietilamino, tetrahidropirolil, piperidinil, piridil, pirazinil, pirolil, imidazolil, pirazolil, oksazolil, izoksazolil,
[image]
I
"I" označava mjesto povezivanja skupine.
4. Spoj formule I ili njegov stereoizomer, racemat, tautomer, izotopski obilježeni spoj ili farmaceutski prihvatljiva sol prema patentnim zahtjevima 1-3, pri čemu
u spoju formule I ili njegovom stereoizomeru, racematu, tautomeru, izotopski obilježenom spoju, predlijeku ili farmaceutski prihvatljivoj soli, spoj formule I može biti odabran između sljedećih struktura formule Ia, formule Ib, formule Ic, formule Id i formule Ie:
[image]
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u formuli Ia, formuli Ib, formuli Ic, formuli Id i formuli Ie, R1, R2, R3, m, n i W su definirani kao u formuli I.
5. Spoj formule I ili njegov stereoizomer, racemat, tautomer, izotopski obilježeni spoj ili farmaceutski prihvatljiva sol prema patentnim zahtjevima 1-4, pri čemu spoj formule I može biti odabran između sljedećih struktura:
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6. Metoda pripreme za spoj formule I ili njegov stereoizomer, racemat, tautomer, izotopski označeni spoj ili farmaceutski prihvatljivu sol prema patentnim zahtjevima 1-5, pri čemu se metoda pripreme sastoji od:
[image]
(a1) reakcije M-1 i M-2 da se dobije M-3, pri čemu se reakcija može izvesti u prisutnosti EDCl.HCl i piridina; i
(a2) reakcije M-3 i RxL1, pri čemu je Rx odabran između R1 i skupine od R1 koja ima hidroksil s hidroksilom supstituiranim s
[image]
kad je Rxskupina od R1 koja ima hidroksil s hidroksilom supstituiranim s
[image]
reakcija se mora izvesti u prisutnosti kiseline i reduktora da se dobije formula I, pri čemu kiselina može biti HCl, a reduktor može biti natrijev borhidrid;
R1, R2, R3, m i W u gornjim koracima su definirani u formuli I, L1 je izlazna skupina i može biti odabrana između halogena i -OTs.
7. Metoda pripreme za spoj formule I ili njegov stereoizomer, racemat, tautomer, izotopski označeni spoj ili farmaceutski prihvatljivu sol prema patentnim zahtjevima 1-5, pri čemu se metoda pripreme sastoji od:
[image]
(b1) reakcije N-1 i RxL1, pri čemu je Rx odabran između R1 i skupine od R1 koja ima hidroksil s hidroksilom supstituiranim s
[image]
kad je Rx skupina od R1 koja ima hidroksil s hidroksilom supstituiranim s
[image]
reakcija se mora izvesti u prisutnosti kiseline i reduktora da bi se dobio N-2, pri čemu kiselina može biti HCl, a reduktor može biti natrijev borhidrid;
(b2) redukcije N-2 dobivenog u gornjem koraku da se dobije N-3, pri čemu reduktor može biti Pd/C; i
(b3) reakcije N-3 i M-2 da se dobije formula I.
R1, R2, R3, m i W u gornjim koracima su definirani u formuli I, L1 je izlazna skupina i može biti odabrana između halogena i -OTs.
8. Farmaceutski pripravak koji sadrži spoj formule I ili njegov stereoizomer, racemat, tautomer, izotopski obilježeni spoj ili farmaceutski prihvatljivu sol prema patentnim zahtjevima 1-5.
9. Upotreba spoja formule I ili njegovog stereoizomera, racemata, tautomera, izotopski obilježenog spoja ili farmaceutski prihvatljive soli prema patentnim zahtjevima 1-5 ili farmaceutskog pripravka prema patentnom zahtjevu 8 u pripravi lijeka za prevenciju i/ili liječenje bolesti ili poremećaja posredovanih IRAK-om.
10. Upotreba prema patentnom zahtjevu 9, pri čemu su bolesti ili poremećaji odabrani između tumora, gihta, sistemskog lupusa eritematozusa, multiple skleroze, metaboličkog sindroma, ateroskleroze, infarkat miokarda, sepse, upalne bolesti crijeva, astme, reumatoidnog artritisa, alergije i slično.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201910906833 | 2019-09-24 | ||
| PCT/CN2020/117093 WO2021057785A1 (zh) | 2019-09-24 | 2020-09-23 | 一种irak抑制剂及其制备方法和用途 |
| EP20869953.8A EP4015513B1 (en) | 2019-09-24 | 2020-09-23 | Irak inhibitor and preparation method therefor and use thereof |
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| HRP20240122T1 true HRP20240122T1 (hr) | 2024-04-12 |
| HRP20240122T8 HRP20240122T8 (hr) | 2024-05-24 |
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| US (1) | US20220298139A1 (hr) |
| EP (1) | EP4015513B1 (hr) |
| JP (1) | JP7353474B2 (hr) |
| KR (1) | KR20220035450A (hr) |
| CN (1) | CN114391013B (hr) |
| AU (1) | AU2020352311B2 (hr) |
| BR (1) | BR112022001568A2 (hr) |
| CA (1) | CA3152167C (hr) |
| CL (1) | CL2022000725A1 (hr) |
| CO (1) | CO2022004978A2 (hr) |
| DO (1) | DOP2022000054A (hr) |
| EC (1) | ECSP22032016A (hr) |
| ES (1) | ES2967642T3 (hr) |
| HR (1) | HRP20240122T8 (hr) |
| IL (1) | IL291158A (hr) |
| LT (1) | LT4015513T (hr) |
| MX (1) | MX2022003504A (hr) |
| PE (1) | PE20220944A1 (hr) |
| PT (1) | PT4015513T (hr) |
| TW (1) | TWI832010B (hr) |
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| EP4155302A4 (en) * | 2020-06-23 | 2023-11-22 | Shanghai Meiyue Biotech Development Co., Ltd. | METHOD FOR PREPARING A CONDENSED PYRAZOLE-TYPE COMPOUND |
| JP2024510651A (ja) * | 2021-03-19 | 2024-03-08 | 上海美悦生物科技発展有限公司 | 化合物の多形体及びその製造方法と使用 |
| CN114404415A (zh) * | 2022-02-25 | 2022-04-29 | 上海美悦生物科技发展有限公司 | 吲唑类化合物用于治疗银屑病的用途 |
| CN115252609B (zh) * | 2022-08-01 | 2023-05-26 | 上海美悦生物科技发展有限公司 | 一种irak4抑制剂的组合物及其制备方法、用途 |
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| JP2599665B2 (ja) * | 1991-05-01 | 1997-04-09 | 大塚製薬株式会社 | ピラジン誘導体 |
| JP6215338B2 (ja) * | 2012-11-08 | 2017-10-18 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | キナーゼモジュレーターとして有用な二環式ヘテロ環置換ピリジル化合物 |
| TWI667233B (zh) * | 2013-12-19 | 2019-08-01 | 德商拜耳製藥公司 | 新穎吲唑羧醯胺，其製備方法、含彼等之醫藥製劑及其製造醫藥之用途 |
| JO3705B1 (ar) * | 2014-11-26 | 2021-01-31 | Bayer Pharma AG | إندازولات مستبدلة جديدة، عمليات لتحضيرها، مستحضرات دوائية تحتوي عليها واستخدامها في إنتاج أدوية |
| WO2016174183A1 (en) * | 2015-04-30 | 2016-11-03 | Bayer Pharma Aktiengesellschaft | Combinations of inhibitors of irak4 with inhibitors of btk |
| WO2017108744A1 (de) * | 2015-12-22 | 2017-06-29 | Bayer Pharma Aktiengesellschaft | Neue substituierte indazole, verfahren zu ihrer herstellung, pharmazeutische präparate die diese enthalten, sowie deren verwendung zur herstellung von arzneimitteln |
| CA3016364A1 (en) * | 2016-03-03 | 2017-09-08 | Bayer Pharma Aktiengesellschaft | New 2-substituted indazoles, methods for producing same, pharmaceutical preparations that contain same, and use of same to produce drugs |
| WO2017207385A1 (de) * | 2016-05-31 | 2017-12-07 | Bayer Pharma Aktiengesellschaft | Substituierte 3-methylindazole, verfahren zu ihrer herstellung, pharmazeutische präparate, die diese enthalten, sowie deren verwendung zur herstellung von arzneimitteln |
| KR102547834B1 (ko) * | 2016-06-01 | 2023-06-26 | 바이엘 애니멀 헬스 게엠베하 | 동물에서의 알레르기성 및/또는 염증성 질환의 치료 및 예방에 유용한 치환된 인다졸 |
| FI3704108T3 (fi) * | 2017-10-31 | 2024-05-23 | Curis Inc | Irak4-estäjä yhdistelmässä bcl-2-estäjän kanssa käytettäväksi syövän hoitoon |
| JP2021508703A (ja) * | 2017-12-26 | 2021-03-11 | カイメラ セラピューティクス， インコーポレイテッド | Ｉｒａｋ分解剤およびそれらの使用 |
| US20220204473A1 (en) * | 2018-12-25 | 2022-06-30 | Shanghai Meiyue Biotech Development Co., Ltd. | Compound as irak inhibitor |
| CN111499612B (zh) * | 2019-01-30 | 2022-12-30 | 上海美悦生物科技发展有限公司 | 一种作为irak抑制剂的化合物及其制备方法和用途 |
| EP4155302A4 (en) * | 2020-06-23 | 2023-11-22 | Shanghai Meiyue Biotech Development Co., Ltd. | METHOD FOR PREPARING A CONDENSED PYRAZOLE-TYPE COMPOUND |
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| Publication number | Publication date |
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| PT4015513T (pt) | 2023-12-19 |
| CA3152167A1 (en) | 2021-04-01 |
| CL2022000725A1 (es) | 2022-11-18 |
| TW202115015A (zh) | 2021-04-16 |
| CO2022004978A2 (es) | 2022-04-29 |
| TWI832010B (zh) | 2024-02-11 |
| ES2967642T3 (es) | 2024-05-03 |
| ZA202204441B (en) | 2022-11-30 |
| CA3152167C (en) | 2023-12-19 |
| WO2021057785A1 (zh) | 2021-04-01 |
| EP4015513A1 (en) | 2022-06-22 |
| JP2022549870A (ja) | 2022-11-29 |
| EP4015513B1 (en) | 2023-11-01 |
| EP4015513A4 (en) | 2022-09-14 |
| CN114391013B (zh) | 2024-01-26 |
| PE20220944A1 (es) | 2022-05-31 |
| AU2020352311B2 (en) | 2023-11-09 |
| MX2022003504A (es) | 2022-07-19 |
| HRP20240122T8 (hr) | 2024-05-24 |
| KR20220035450A (ko) | 2022-03-22 |
| JP7353474B2 (ja) | 2023-09-29 |
| AU2020352311A1 (en) | 2022-04-14 |
| ECSP22032016A (es) | 2022-05-31 |
| DOP2022000054A (es) | 2022-07-15 |
| IL291158A (en) | 2022-05-01 |
| CN114391013A (zh) | 2022-04-22 |
| US20220298139A1 (en) | 2022-09-22 |
| BR112022001568A2 (pt) | 2022-03-22 |
| LT4015513T (lt) | 2023-12-11 |
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