HRP20210501T1 - 4,6-SUPSTITUIRANI PIRAZOLO[1,5-a]PIRAZINI KAO INHIBITORI JANUS KINAZE - Google Patents
4,6-SUPSTITUIRANI PIRAZOLO[1,5-a]PIRAZINI KAO INHIBITORI JANUS KINAZE Download PDFInfo
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- HRP20210501T1 HRP20210501T1 HRP20210501TT HRP20210501T HRP20210501T1 HR P20210501 T1 HRP20210501 T1 HR P20210501T1 HR P20210501T T HRP20210501T T HR P20210501TT HR P20210501 T HRP20210501 T HR P20210501T HR P20210501 T1 HRP20210501 T1 HR P20210501T1
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- 229940122245 Janus kinase inhibitor Drugs 0.000 title 1
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims 127
- 150000001875 compounds Chemical class 0.000 claims 62
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 29
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 21
- 125000003545 alkoxy group Chemical group 0.000 claims 19
- 150000003839 salts Chemical class 0.000 claims 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims 15
- 238000006243 chemical reaction Methods 0.000 claims 13
- 125000001424 substituent group Chemical group 0.000 claims 13
- 229910052736 halogen Inorganic materials 0.000 claims 12
- 239000000825 pharmaceutical preparation Substances 0.000 claims 12
- 150000002367 halogens Chemical class 0.000 claims 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 7
- 125000000623 heterocyclic group Chemical group 0.000 claims 7
- 239000012453 solvate Substances 0.000 claims 6
- 208000035475 disorder Diseases 0.000 claims 5
- 125000005843 halogen group Chemical group 0.000 claims 5
- 125000005842 heteroatom Chemical group 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 4
- 125000005227 alkyl sulfonate group Chemical group 0.000 claims 4
- 125000005228 aryl sulfonate group Chemical group 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 206010025135 lupus erythematosus Diseases 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 4
- 239000003153 chemical reaction reagent Substances 0.000 claims 3
- -1 deoxyspergvaline Chemical compound 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 125000001153 fluoro group Chemical group F* 0.000 claims 3
- 239000003112 inhibitor Substances 0.000 claims 3
- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 229940124597 therapeutic agent Drugs 0.000 claims 3
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims 3
- MAUMSNABMVEOGP-UHFFFAOYSA-N (methyl-$l^{2}-azanyl)methane Chemical compound C[N]C MAUMSNABMVEOGP-UHFFFAOYSA-N 0.000 claims 2
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 claims 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 2
- 206010061218 Inflammation Diseases 0.000 claims 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 2
- 206010003246 arthritis Diseases 0.000 claims 2
- 125000002393 azetidinyl group Chemical group 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims 2
- 230000004054 inflammatory process Effects 0.000 claims 2
- 230000000968 intestinal effect Effects 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- HPNSFSBZBAHARI-UHFFFAOYSA-N micophenolic acid Natural products OC1=C(CC=C(C)CCC(O)=O)C(OC)=C(C)C2=C1C(=O)OC2 HPNSFSBZBAHARI-UHFFFAOYSA-N 0.000 claims 2
- HPNSFSBZBAHARI-RUDMXATFSA-N mycophenolic acid Chemical compound OC1=C(C\C=C(/C)CCC(O)=O)C(OC)=C(C)C2=C1C(=O)OC2 HPNSFSBZBAHARI-RUDMXATFSA-N 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 208000017520 skin disease Diseases 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 125000004434 sulfur atom Chemical group 0.000 claims 2
- 108020004491 Antisense DNA Proteins 0.000 claims 1
- 108020005544 Antisense RNA Proteins 0.000 claims 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- 229940123587 Cell cycle inhibitor Drugs 0.000 claims 1
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 claims 1
- 229930105110 Cyclosporin A Natural products 0.000 claims 1
- PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 claims 1
- 108010036949 Cyclosporine Proteins 0.000 claims 1
- 208000002633 Febrile Neutropenia Diseases 0.000 claims 1
- 206010016654 Fibrosis Diseases 0.000 claims 1
- 201000005569 Gout Diseases 0.000 claims 1
- 208000002250 Hematologic Neoplasms Diseases 0.000 claims 1
- 206010020751 Hypersensitivity Diseases 0.000 claims 1
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 claims 1
- 102000014150 Interferons Human genes 0.000 claims 1
- 108010050904 Interferons Proteins 0.000 claims 1
- FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 claims 1
- 208000001145 Metabolic Syndrome Diseases 0.000 claims 1
- CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 229940079156 Proteasome inhibitor Drugs 0.000 claims 1
- 206010040047 Sepsis Diseases 0.000 claims 1
- 208000006045 Spondylarthropathies Diseases 0.000 claims 1
- 206010051379 Systemic Inflammatory Response Syndrome Diseases 0.000 claims 1
- QJJXYPPXXYFBGM-LFZNUXCKSA-N Tacrolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1\C=C(/C)[C@@H]1[C@H](C)[C@@H](O)CC(=O)[C@H](CC=C)/C=C(C)/C[C@H](C)C[C@H](OC)[C@H]([C@H](C[C@H]2C)OC)O[C@@]2(O)C(=O)C(=O)N2CCCC[C@H]2C(=O)O1 QJJXYPPXXYFBGM-LFZNUXCKSA-N 0.000 claims 1
- 206010052779 Transplant rejections Diseases 0.000 claims 1
- 229960003697 abatacept Drugs 0.000 claims 1
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims 1
- 229960001138 acetylsalicylic acid Drugs 0.000 claims 1
- 230000004913 activation Effects 0.000 claims 1
- 238000011374 additional therapy Methods 0.000 claims 1
- 125000005907 alkyl ester group Chemical group 0.000 claims 1
- 239000002168 alkylating agent Substances 0.000 claims 1
- 229940100198 alkylating agent Drugs 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 239000004037 angiogenesis inhibitor Substances 0.000 claims 1
- 229940121369 angiogenesis inhibitor Drugs 0.000 claims 1
- 230000002280 anti-androgenic effect Effects 0.000 claims 1
- 230000003388 anti-hormonal effect Effects 0.000 claims 1
- 230000003110 anti-inflammatory effect Effects 0.000 claims 1
- 230000000340 anti-metabolite Effects 0.000 claims 1
- 239000000051 antiandrogen Substances 0.000 claims 1
- 229940030495 antiandrogen sex hormone and modulator of the genital system Drugs 0.000 claims 1
- 239000002256 antimetabolite Substances 0.000 claims 1
- 229940100197 antimetabolite Drugs 0.000 claims 1
- 239000003816 antisense DNA Substances 0.000 claims 1
- 229940092117 atgam Drugs 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 239000002775 capsule Substances 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 239000003184 complementary RNA Substances 0.000 claims 1
- 229960004397 cyclophosphamide Drugs 0.000 claims 1
- 239000000824 cytostatic agent Substances 0.000 claims 1
- 229960002806 daclizumab Drugs 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003534 dna topoisomerase inhibitor Substances 0.000 claims 1
- 239000002532 enzyme inhibitor Substances 0.000 claims 1
- 208000030533 eye disease Diseases 0.000 claims 1
- 230000004761 fibrosis Effects 0.000 claims 1
- 239000003102 growth factor Substances 0.000 claims 1
- 208000014951 hematologic disease Diseases 0.000 claims 1
- 229960004171 hydroxychloroquine Drugs 0.000 claims 1
- XXSMGPRMXLTPCZ-UHFFFAOYSA-N hydroxychloroquine Chemical compound ClC1=CC=C2C(NC(C)CCCN(CCO)CC)=CC=NC2=C1 XXSMGPRMXLTPCZ-UHFFFAOYSA-N 0.000 claims 1
- 229960001680 ibuprofen Drugs 0.000 claims 1
- 239000000367 immunologic factor Substances 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 239000012444 intercalating antibiotic Substances 0.000 claims 1
- 229940079322 interferon Drugs 0.000 claims 1
- 229960000681 leflunomide Drugs 0.000 claims 1
- VHOGYURTWQBHIL-UHFFFAOYSA-N leflunomide Chemical compound O1N=CC(C(=O)NC=2C=CC(=CC=2)C(F)(F)F)=C1C VHOGYURTWQBHIL-UHFFFAOYSA-N 0.000 claims 1
- 239000003446 ligand Substances 0.000 claims 1
- 230000036210 malignancy Effects 0.000 claims 1
- 229960003105 metformin Drugs 0.000 claims 1
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 229960000485 methotrexate Drugs 0.000 claims 1
- 230000011278 mitosis Effects 0.000 claims 1
- 229940014456 mycophenolate Drugs 0.000 claims 1
- 229960000951 mycophenolic acid Drugs 0.000 claims 1
- 229960002009 naproxen Drugs 0.000 claims 1
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 210000000056 organ Anatomy 0.000 claims 1
- 239000007800 oxidant agent Substances 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- 229960005489 paracetamol Drugs 0.000 claims 1
- 229960002702 piroxicam Drugs 0.000 claims 1
- QYSPLQLAKJAUJT-UHFFFAOYSA-N piroxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 QYSPLQLAKJAUJT-UHFFFAOYSA-N 0.000 claims 1
- 229940096701 plain lipid modifying drug hmg coa reductase inhibitors Drugs 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 239000003207 proteasome inhibitor Substances 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- ZAHRKKWIAAJSAO-UHFFFAOYSA-N rapamycin Natural products COCC(O)C(=C/C(C)C(=O)CC(OC(=O)C1CCCCN1C(=O)C(=O)C2(O)OC(CC(OC)C(=CC=CC=CC(C)CC(C)C(=O)C)C)CCC2C)C(C)CC3CCC(O)C(C3)OC)C ZAHRKKWIAAJSAO-UHFFFAOYSA-N 0.000 claims 1
- 208000023504 respiratory system disease Diseases 0.000 claims 1
- 102000027483 retinoid hormone receptors Human genes 0.000 claims 1
- 108091008679 retinoid hormone receptors Proteins 0.000 claims 1
- 230000008054 signal transmission Effects 0.000 claims 1
- 229960002930 sirolimus Drugs 0.000 claims 1
- QFJCIRLUMZQUOT-HPLJOQBZSA-N sirolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 QFJCIRLUMZQUOT-HPLJOQBZSA-N 0.000 claims 1
- 201000005671 spondyloarthropathy Diseases 0.000 claims 1
- 150000003431 steroids Chemical class 0.000 claims 1
- 229960001967 tacrolimus Drugs 0.000 claims 1
- QJJXYPPXXYFBGM-SHYZHZOCSA-N tacrolimus Natural products CO[C@H]1C[C@H](CC[C@@H]1O)C=C(C)[C@H]2OC(=O)[C@H]3CCCCN3C(=O)C(=O)[C@@]4(O)O[C@@H]([C@H](C[C@H]4C)OC)[C@@H](C[C@H](C)CC(=C[C@@H](CC=C)C(=O)C[C@H](O)[C@H]2C)C)OC QJJXYPPXXYFBGM-SHYZHZOCSA-N 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
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- 239000003558 transferase inhibitor Substances 0.000 claims 1
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 claims 1
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 claims 1
- 239000002451 tumor necrosis factor inhibitor Substances 0.000 claims 1
Classifications
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- 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
- A61K31/4985—Pyrazines or piperazines ortho- or peri-condensed with heterocyclic ring systems
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- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
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Claims (33)
1. Spoj opće Formule I:
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ili stereoizomer, ili njegova farmaceutski prihvatljiva sol ili solvat, naznačen time što:
R1 je hidroksi(1-6C)alkil, HOCH2(ciklopropilidin)CH2-, (1-4C alkoksi)(1-6C)hidroksialkil, (hidroksi)trifluor(1-6C)alkil, dihidroksi(2-6C)alkil, H2N(3-6C)hidroksialkil, (1-3C alkil)NH(3-6C)hidroksialkil, (1-3C alkil)2N(3-6C)hidroksialkil, H2N(1-4C alkoksi)(3-6C)alkil, Cyc1(CH2)m-, hetCyc1, hetCyc2CH2-, RaRbNC(=O)CH2-, hetCyc3a(1-3C)alkil, hetCyc3b(2-3C)hidroksialkil, RcRdN(2-3C)alkil, (1-3C alkil)2NSO2(2-3C)alkil, hetCyc4, (1-6C)alkil ili CH3SO2(1-6C)alkil;
Cyc1 je 4-6-eročlani cikloalkil supstituiran s 1-2 supstituenta koje se neovisno bira iz skupine koju čine HO, HOCH2-, (1-3C)alkil, H2NHC(=O)-, (1-3C alkil)2NC(=O)-, te HOCH2CH2NHC(=O)-;
m je 0 ili 1;
hetCyc1 je 4-6-eročlani heterociklički prsten koji ima heteroatom u prstenu kojeg se bira između N, O i S, gdje S može biti oksidiran do SO2, gdje navedeni heterociklički prsten može biti supstituiran sa supstituentom kojeg se bira iz skupine koju čine OH, (1-3C alkil)C(=O)-, (1-3C alkil)SO2-, (1-3C alkil)NHC(=O)- i NH2CH2C(=O)-;
hetCyc2 je 4-6-eročlani heterociklički prsten koji ima prsten S atom, gdje je S oksidiran do SO2;
Ra i Rb su neovisno H ili (1-3C)alkil; ili
Ra i Rb zajedno s atomom dušika na koje su vezani tvore 4-6-eročlani prsten koji može imati atom kisika u prstenu;
hetCyc3a i hetCyc3b su neovisno 4-6-eročlani heterociklički prsten koji ima 1-2 heteroatoma u prstenu koje se neovisno bira između N i O, gdje navedeni heterociklički prsten može biti supstituiran s 1-2 supstituenta koje se neovisno bira iz skupine koju čine halogen, OH, (1-4C)alkoksi, HOCH2-, (1-3C alkil)C(=O)- i okso;
Rc je H ili (1-3C)alkil;
Rd je (1-3C)alkil, (1-3C alkil)SO2-, hetCyca ili (3-6C)cikloalkil koji može biti supstituiran s HOCH2-;
hetCyca je 5-6-eročlani azaciklički prsten koji može biti supstituiran s 1-2 supstituenta koje se neovisno bira između okso i (1-3C)alkil;
hetCyc4 je azetidinil supstituiran s ((CH3)2N)2P(=O)- ili Y-C(=O)-;
Y je ReRfN(CH2)n-, hetCycbCH2-, Cyc2, hidroksi(1-3C)alkil, (1-3C alkil)2NC(=O)-, (1-3C)alkilSO2- ili (1-3C)alkil;
n je 0 ili 1;
Re i Rf su neovisno H ili (1-3C)alkil;
hetCycb je 4-5-eročlani azaciklički prsten koji može biti supstituiran s OH;
Cyc2 je (3-6C)cikloalkil koji može biti supstituiran s OH;
R2 je (1-6C)alkil, trifluor(1-6C)alkil, difluor(1-6C)alkil, fluor(1-6C)alkil, hidroksi(1-6C)alkil, (1-6C)alkoksi, (3-6C)cikloalkil (koji može biti supstituiran s jednim ili dva halogena), (3-6C)cikloalkilCH2-, HOC(=O)- ili fenil; i
R3 je (1-6C)alkil ili (3-6C)cikloalkil; ili
R2 i R3 zajedno s atomom ugljika na kojeg su vezani tvore 3-7-eročlani cikloalkilni prsten koji može biti supstituiran s jednim ili dva supstituenta koje se neovisno bira između OH, (1-6C)alkila i hidroksi(1-6C)alkila; ili
R2 i R3 zajedno s atomom ugljika na kojeg su vezani tvore 4-eročlani zasićeni azaciklički prsten supstituiran s SO2CF3; i
R4 je vodik ili (1-6C)alkil.
2. Spoj u skladu s patentnim zahtjevom 1, naznačen time što:
R1 je hidroksi(1-6C)alkil, HOCH2(ciklopropilidin)CH2-, (1-4C alkoksi)(1-6C)hidroksialkil, (hidroksi)trifluor(1-6C)alkil, dihidroksi(2-6C)alkil, H2N(3-6C)hidroksialkil, (1-3C alkil)NH(3-6C)hidroksialkil, (1-3C alkil)2N(3-6C)hidroksialkil, H2N(1-4C alkoksi)(3-6C)alkil, Cyc1(CH2)m-, hetCyc1, hetCyc2CH2-, RaRbNC(=O)CH2-, hetCyc3a(1-3C alkil)-, hetCyc3b(2-3C)hidroksialkil, RcRdN(2-3C)alkil, (1-3C alkil)2NSO2(2-3C)alkil ili hetCyc4;
Cyc1 je 4-6-eročlani cikloalkil supstituiran s 1-2 supstituenta koje se neovisno bira iz skupine koju čine HO, HOCH2-, (1-3C)alkil, H2NHC(=O)-, (1-3C alkil)2NC(=O)-, te HOCH2CH2NHC(=O)-;
m je 0 ili 1;
hetCyc1 je 4-6-eročlani heterociklički prsten koji ima heteroatom u prstenu kojeg se bira između N, O i S, gdje S može biti oksidiran do SO2, gdje navedeni heterociklički prsten je supstituiran sa supstituentom kojeg se bira iz skupine koju čine OH, (1-3C alkil)C(=O)-, (1-3C alkil)SO2-, (1-3C alkil)NHC(=O)- i H2NCH2C(=O)-;
hetCyc2 je 4-6-eročlani heterociklički prsten koji ima prsten S atom, gdje je S oksidiran do SO2;
Ra i Rb su neovisno H ili (1-3C)alkil; ili
Ra i Rb zajedno s atomom dušika na koje su vezani tvore 4-6-eročlani prsten koji može imati atom kisika u prstenu;
hetCyc3a je 4-6-eročlani heterociklički prsten koji ima 1-2 heteroatoma u prstenu koje se neovisno bira između N i O, gdje navedeni heterociklički prsten je supstituiran s 1-2 supstituenta koje se neovisno bira iz skupine koju čine halogen, OH, (1-4C)alkoksi, HOCH2-, (1-3C alkil)C(=O)- i okso;
hetCyc3b je 4-6-eročlani heterociklički prsten koji ima 1-2 heteroatoma u prstenu koje se neovisno bira između N i O, gdje navedeni heterociklički prsten može biti supstituiran s 1-2 supstituenta koje se neovisno bira iz skupine koju čine halogen, OH, (1-4C)alkoksi, HOCH2-, (1-3C alkil)C(=O)- i okso;
Rc je H ili (1-3C)alkil;
Rd je (1-3C)alkil, (1-3C alkil)SO2-, hetCyca ili (3-6C)cikloalkil koji može biti supstituiran s HOCH2-;
hetCyca je 5-6-eročlani azaciklički prsten koji može biti supstituiran s 1-2 supstituenta koje se neovisno bira između okso i (1-3C)alkil;
hetCyc4 je azetidinil supstituiran s ((CH3)2N)2P(=O)- ili Y-C(=O)-;
Y je ReRfN(CH2)n-, hetCycbCH2-, Cyc2, hidroksi(1-3C)alkil ili (1-3C alkil)2NC(=O)-;
n je 0 ili 1;
Re i Rf su neovisno H ili (1-3C)alkil;
hetCycb je 4-5-eročlani azaciklički prsten koji može biti supstituiran s OH;
Cyc2 je (3-6C)cikloalkil koji može biti supstituiran s OH; i
R2 je (1-6C)alkil, trifluor(1-6C)alkil, difluor(1-6C)alkil, fluor(1-6C)alkil, hidroksi(1-6C)alkil, (1-6C)alkoksi, (3-6C)cikloalkil (koji može biti supstituiran s jednim ili dva halogena), (3-6C)cikloalkilCH2-, HOC(=O)- ili fenil.
3. Spoj u skladu s patentnim zahtjevom 1, naznačen time što je R1 hidroksi(1-6C)alkil, HOCH2(ciklopropilidin)CH2-, (1-4C alkoksi)(1-6C)hidroksialkil, (hidroksi)trifluor(1-6C)alkil, dihidroksi(2-6C)alkil, H2N(3-6C)hidroksialkil, (1-3C alkil)NH(3-6C)hidroksialkil, (1-3C alkil)2N(3-6C)hidroksialkil, H2N(1-4C alkoksi)(3-6C)alkil, Cyc1(CH2)m-, hetCyc1, hetCyc2CH2-, RaRbNC(=O)CH2-, hetCyc3a(1-3C)alkil, hetCyc3b(2-3C)hidroksialkil, RcRdN(2-3C alkil)-, (1-3C alkil)2NSO2(2-3C alkil)- ili hetCyc4.
4. Spoj u skladu s patentnim zahtjevom 1, naznačen time što je R1 hidroksi(1-6C)alkil, HOCH2(ciklopropilidin)CH2-, (1-4C alkoksi)(1-6C)hidroksialkil, (hidroksi)trifluor(1-6C)alkil, dihidroksi(2-6C)alkil, H2N(3-6C)hidroksialkil, (1-3C alkil)NH(3-6C)hidroksialkil, (1-3C alkil)2N(3-6C)hidroksialkil ili H2N(1-4C alkoksi)(3-6C)alkil.
5. Spoj u skladu s patentnim zahtjevom 1, naznačen time što je R1 dihidroksi(2-6C)alkil, H2N(3-6C)hidroksialkil, (1-3C alkil)NH(3-6C)hidroksialkil ili (1-3C alkil)2N(3-6C)hidroksialkil.
6. Spoj u skladu s patentnim zahtjevom 1, naznačen time što je R1 dihidroksi(2-6C)alkil.
7. Spoj u skladu s patentnim zahtjevom 1, naznačen time što je R1 H2N(3-6C)hidroksialkil, (1-3C alkil)NH(3-6C)hidroksialkil ili (1-3C alkil)2N(3-6C)hidroksialkil.
8. Spoj u skladu s bilo kojim od patentnih zahtjeva 1-7, naznačen time što:
R2 je (1-6C)alkil, trifluor(1-6C)alkil, difluor(1-6C)alkil, fluor(1-6C)alkil, hidroksi(1-6C)alkil, (1-6C)alkoksi, (3-6C)cikloalkil (koji može biti supstituiran s jednim ili dva halogena), (3-6C)cikloalkilCH2-, HOC(=O)- ili fenil;
R3 je (1-6C)alkil ili (3-6C)cikloalkil; i
R4 je vodik ili (1-6C)alkil.
9. Spoj u skladu s patentnim zahtjevom 8, naznačen time što:
R2 je (1-6C)alkil;
R3 je (1-6C)alkil; i
R4 je vodik.
10. Spoj u skladu s bilo kojim od patentnih zahtjeva 1-7, naznačen time što:
R2 i R3 zajedno s atomom ugljika na kojeg su vezani tvore 3-7-eročlani cikloalkilni prsten koji može biti supstituiran s jednom ili dvije skupine koje se neovisno bira između OH, (1-6C)alkila i hidroksi(1-6C)alkila; i
R4 je vodik ili (1-6C)alkil.
11. Spoj u skladu s bilo kojim od patentnih zahtjeva 1-7, naznačen time što:
R2 i R3 zajedno s atomom ugljika na kojeg su vezani tvore 4-eročlani zasićeni azaciklički prsten supstituiran s SO2CF3; i
R4 je vodik ili (1-6C)alkil.
12. Spoj u skladu s patentnim zahtjevom 1, naznačen time što ga se bira između:
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i njihovih farmaceutski prihvatljivih soli.
13. Spoj u skladu s patentnim zahtjevom 12, naznačen time što ga se bira između:
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i njihovih farmaceutski prihvatljivih soli.
14. Spoj u skladu s patentnim zahtjevom 12, naznačen time što ga se bira između:
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i njihovih farmaceutski prihvatljivih soli.
15. Spoj u skladu s patentnim zahtjevom 12, naznačen time što ga se bira između:
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i njihovih farmaceutski prihvatljivih soli.
16. Spoj u skladu s patentnim zahtjevom 12, naznačen time što ga se bira između:
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i njihovih farmaceutski prihvatljivih soli.
17. Spoj u skladu s patentnim zahtjevom 12, naznačen time što ga se bira između:
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i njihovih farmaceutski prihvatljivih soli.
18. Spoj u skladu s patentnim zahtjevom 12, naznačen time što ga se bira između:
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i njihovih farmaceutski prihvatljivih soli.
19. Spoj u skladu s patentnim zahtjevom 12, naznačen time što ga se bira između:
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i njihovih farmaceutski prihvatljivih soli.
20. Spoj u skladu s patentnim zahtjevom 12, naznačen time što je spoj sol trifluoroctene kiseline ili sol klorovodične kiseline.
21. Farmaceutski pripravak, , naznačen time što sadrži spoj Formule I u skladu s bilo kojim od patentnih zahtjeva 1 do 20, ili njegovu farmaceutski prihvatljivu sol ili solvat, kao i farmaceutski prihvatljivi razrjeđivač ili nosač.
22. Spoj Formule I u skladu s bilo kojim od patentnih zahtjeva 1 do 20, ili njegova farmaceutski prihvatljiva sol ili solvat, ili farmaceutski pripravak u skladu s patentnim zahtjevom 21, naznačeni time što su namijenjeni upotrebi u terapiji.
23. Spoj Formule I u skladu s bilo kojim od patentnih zahtjeva 1 do 20, ili njegova farmaceutski prihvatljiva sol ili solvat, ili farmaceutski pripravak u skladu s patentnim zahtjevom 21, naznačeni time što su namijenjeni upotrebi u liječenju autoimune bolesti ili upalne bolesti.
24. Spoj ili farmaceutski pripravak namijenjeni upotrebi u skladu s patentnim zahtjevom 23, naznačeni time što se bolest ili poremećaj bira između:
(i) artritisa;
(ii) crijevnih upala;
(iii) bolesti dišnih puteva;
(iv) alergijskih reakcija;
(v) očnih bolesti, poremećaja ili stanja;
(vi) kožnih bolesti, stanja ili poremećaja;
(vii) sepse, sindroma sistemnog upalnog odgovora, te neutropenične groznice;
(viii) fibroze;
(ix) gihta;
(x) lupusa i manifestacija lupusa;
(xi) neurodegenerativnih bolesti;
(xii) dijabetesa i komplikacija dijabetesa, metaboličkog sindroma i pretilosti;
(xiii) aksijalne spondiloartorpatije (aksijalne SpA); i
(xiv) poremećaja aktivacije interferona tipa 1.
25. Spoj ili farmaceutski pripravak namijenjeni upotrebi u skladu s patentnim zahtjevom 24, naznačeni time što se bolest ili poremećaj bira između:
(i) artritisa;
(ii) crijevnih upala;
(vi) kožnih bolesti; i
(x) lupusa i manifestacija lupusa.
26. Spoj Formule I u skladu s bilo kojim od patentnih zahtjeva 1 do 20, ili njegova farmaceutski prihvatljiva sol ili solvat, ili farmaceutski pripravak u skladu s patentnim zahtjevom 21, naznačeni time što su namijenjeni upotrebi u liječenju odbacivanja presatka organa, tkiva ili stanica.
27. Spoj Formule I u skladu s bilo kojim od patentnih zahtjeva 1 do 20, ili njegova farmaceutski prihvatljiva sol ili solvat, ili farmaceutski pripravak u skladu s patentnim zahtjevom 21, naznačeni time što su namijenjeni upotrebi u liječenju hematoloških poremećaja i malignoma.
28. Spoj ili farmaceutski pripravak namijenjeni upotrebi u skladu s bilo kojim od patentnih zahtjeva 22-27, naznačeni time što je navedeni spoj Formule I formuliran za oralnu primjenu.
29. Spoj ili farmaceutski pripravak namijenjeni upotrebi u skladu s patentnim zahtjevom 28, naznačeni time što je navedeni spoj Formule I formuliran u obliku tablete ili kapsule.
30. Spoj ili farmaceutski pripravak namijenjeni upotrebi u skladu s bilo kojim od patentnih zahtjeva 22-29, naznačeni time što dodatno uključuju primjenu dodatne terapije ili terapijskog sredstva.
31. Spoj ili farmaceutski pripravak namijenjeni upotrebi u skladu s patentnim zahtjevom 30, naznačeni time što se dodatno terapijsko sredstvo bira iz skupine koju čine ciklosporin A, rapamicin, takrolimus, leflunomid, deoksispergvalin, mikofenolat, daklizumab, OKT3, AtGam, aspirin, acetaminofen, ibuprofen, naproksen, piroksikam, protuupalni steroidi, metotreksat, statini, sredstva prodiv TNF, abatacept, ciklofosfamid, mikofenolna kiselina, hidroksiklorokin, te metformin.
32. Spoj ili farmaceutski pripravak namijenjeni upotrebi u skladu s patentnim zahtjevom 30, naznačeni time što se dodatno terapijsko sredstvo bira iz skupine koju čine inhibitori mitoze, alklirajuća sredstva, antimetaboliti, protusmislena DNA ili RNA, interkalirajući antibiotici, inhibitori čimbenika rasta, inhibitori prijenosa signala, inhibitori staničnog ciklusa, inhibitori enzima, modulatori retinoidnog receptora, inhibitori proteasoma, inhibitori topoizomeraze, modifikatori biološkog odgovora, antihormoni, inhibitori angiogeneze, citostatska sredstva, antiandrogeni, ciljana protutijela, inhibitori HMG-CoA-reduktaze, te inhibitori prenil-proteinske transferaze.
33. Postupak priprave spoja Formule I, ili njegove farmaceutski prihvatljive soli, u skladu s patentnim zahtjevom 1, naznačen time što se sastoji u:
(a) reakciji odgovarajućeg spoja formule II:
[image]
,
gdje su R2, R3 i R4 kao što je definirano za Formulu I, a Rt i Ru su H ili (1-6C)alkil, ili Rt i Ru zajedno s atomima na koje su vezani tvore 5-6-eročlani prsten koji može biti supstituiran s 1-4 supstituenta koje se bira između (1-3C alkila), s odgovarajućim spojem formule III:
[image]
,
gdje je R1 kao što je definirano za Formulu I, ai L1 je halogen, alkilsulfonatna skupina, arilsulfonatna skupina ili triflatna skupina, u prisutnosti paladijskog katalizatora i baze i izborno u prisutnosti liganda; ili
(b) za spoj Formule I, gdje je R1 (1-6C)alkil, hidroksi(1-6C)alkil, hetCyc1, hetCyc2CH2-, RaRbNC(=O)CH2-, hetCyc3a(1-3C alkil)-, RcRdN(2-3C alkil)-, (1-3C alkil)2NSO2(2-3C alkil)- ili CH3SO2(1-6C)alkil, reakciji odgovarajućeg spoja formule IV:
[image]
,
gdje su R2, R3 i R4 kao što je definirano za Formulu I, s (1-6C)alkil-L2, hidroksi(1-6C)alkil-L2, hetCyc1-L2, hetCyc2CH2-L2, RaRbNC(=O)CH2-L2, hetCyc3a(1-3C alkil)-L2, RcRdN(2-3C alkil)-L2, (1-3C alkil)2NSO2(2-3C alkil)-L2 ili CH3SO2(1-6C)alkil-L2, a L2 je halogen, alkilsulfonatna skupina ili arilsulfonatna skupina, u prisutnosti baze, gdje su hetCyc1, Ra, Rb, hetCyc3a, Rc, te Rd kao što je definirano za Formulu I; ili
(c) za spoj Formule I, gdje je R1 dihidroksi(2-6C)alkil, reakciji odgovarajućeg spoja formule IV:
[image]
,
gdje su R2, R3 i R4 kao što je definirano za Formulu I, sa spojem formule V, VI ili VII:
[image]
[image]
[image]
gdje je svaki R’ metil, Rv, Rw i Rx su neovisno H ili metil, a L3 je atom halogena, alkilsulfonatna skupina ili arilsulfonatna skupina, u prisutnosti baze, uz naknadnu obradu klorovodičnom kiselinom; ili
(d) za spoj Formule I, gdje je R1 H2NCH2CH(OH)CH2-, reakciji odgovarajućeg spoja formule VIII:
[image]
,
gdje su R2, R3 i R4 kao što je definirano za Formulu I, s bazom; ili
(e) za spoj Formule I, gdje je R1 (1-3C alkil)NH(3-6C)hidroksialkil, (1-3C alkil)2N(3-6C)hidroksialkil, ili hetCyc3b(2-3C)hidroksialkil-, gdje je hetCyc3b 4-6-eročlani heterociklički prsten koji ima atom dušika u prstenu, gdje navedeni heterociklički prsten može biti supstituiran s 1-2 supstituenta koje se neovisno bira iz skupine koju čine halogen ili (1-4C)alkoksi, reakciji odgovarajućeg spoja formule IX:
[image]
,
gdje su R2, R3 i R4 kao što je definirano za Formulu I, s reagensom formule (1-3C alkil)NH2, (1-3C alkil)2NH ili
[image]
,
gdje se Ry i Rz neovisno bira iz skupine koju čine halogen ili (1-4C)alkoksi, a hetCyc3b je 4-6-eročlani heterociklički prsten koji ima atom dušika u prstenu, gdje navedeni heterociklički prsten može biti supstituiran s 1-2 supstituenta koje se neovisno bira iz skupine koju čine halogen ili (1-4C)alkoksi; ili
(f) za spoj Formule I, gdje je R1 hidroksi(1-6C)alkil, (hidroksi)trifluor(1-6C)alkil ili (1-4C alkoksi)(1-6C)hidroksialkil, reakciji odgovarajućeg spoja formule X:
[image]
,
gdje su R2, R3 i R4 kao što je definirano za Formulu I, s reagensom formule
[image]
,
gdje G je (1-4C)alkil, trifluor(1-4C)alkil ili (1-4C alkoksi)(1-4C)alkil; ili
(g) za spoj Formule I, gdje je R1
[image]
ili
[image]
,
reakciji odgovarajućeg spoja formule XI:
[image]
,
gdje su R2, R3 i R4 kao što je definirano za Formulu I, odnosno R1a je
[image]
ili
[image]
,
s reducensom; ili
(h) za spoj Formule I, gdje je R1 hidroksi(1-6C)alkil, reakciji odgovarajućeg spoja gdje je hidroksi(1-6C)alkil zaštićen kao alkilni ester s bazom; ili
(i) za spoj Formule I, gdje je R1 RcRdN(CH2CH2)- ili hetCyc3a(CH2CH2)-, gdje su Rc, Rd, te hetCyc3a kao što je definirano za Formulu I, reakciji odgovarajućeg spoja formule XII:
[image]
,
gdje su R2, R3 i R4 kao što je definirano za Formulu I, a L4 je halogen, alkilsulfonatna skupina ili arilsulfonatna skupina, s reagensom formule RcRdNH2 ili
[image]
,
gdje je hetCyc3a kao što je definirano za Formulu I; ili
(j) za spoj Formule I, gdje je R1 H2NCH2CH(OCH3)CH2-, reakciji odgovarajućeg spoja formule XIII:
[image]
,
gdje su R2, R3 i R4 kao što je definirano za Formulu I, s hidrazinom; ili
(k) za spoj Formule I, gdje je R1
[image]
,
reakciji odgovarajućeg spoja formule XIV:
[image]
,
gdje su R2, R3 i R4 kao što je definirano za Formulu I, s oksidansom; ili
(l) za spoj Formule I, gdje je R1 Cyc1(CH2)m-, Cyc1 je 4-6-eročlani cikloalkil supstituiran s H2NHC(=O)- ili (1-3C alkil)2NC(=O)-, a m je 0, reakciji odgovarajućeg spoja Formule I, gdje je R1 Cyc1CH2)m-, Cyc1 je 4-6-eročlani cikloalkil supstituiran s CH3C(=O)O-, a m je 0 s amonijakom ili (1-3C alkil)NH-; ili
(m) za spoj Formule I, gdje R2 i R3 tvore 4-eročlani azaciklički prsten supstituiran s SO2CF3, a R1 i R4 su kao što je definirano za Formulu I, reakciji spoja formule XIV:
[image]
,
gdje su R1 i R4 kao što je definirano za Formulu I, s anhidridom trifluormetansulfonske kiseline u prisutnosti baze; uz
izborno uklanjanje svih zaštitnih skupina i izbornu pripravu njegove farmaceutski prihvatljive soli.
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| EP15819933.1A EP3227297B1 (en) | 2014-12-05 | 2015-12-04 | 4,6-substituted-pyrazolo[1,5-a]pyrazines as janus kinase inhibitors |
| PCT/US2015/064062 WO2016090285A1 (en) | 2014-12-05 | 2015-12-04 | 4,6-SUBSTITUTED-PYRAZOLO[1,5-a]PYRAZINES AS JANUS KINASE INHIBITORS |
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| CR20170309A (es) | 2014-12-05 | 2018-02-02 | Celgene Corp | Pirazolo [1,5-a] pirazinas 4,6-sustituidas como inhibidores de janus cinasas |
| UA119835C2 (uk) | 2016-02-24 | 2019-08-12 | Пфайзер Інк. | ПОХІДНІ ПІРАЗОЛО[1,5-а]ПІРАЗИН-4-ІЛУ ЯК JAK-ІНГІБІТОРИ |
| US11028080B2 (en) | 2016-03-11 | 2021-06-08 | Denali Therapeutics Inc. | Substituted pyrimidines as LRKK2 inhibitors |
| BR112018075569A2 (pt) | 2016-06-16 | 2019-03-19 | Denali Therapeutics Inc. | pirimidin-2-ilamino-1h-pirazóis como inibidores de lrrk2 para uso no tratamento de distúrbios neurodegenerativos |
| GB201617758D0 (en) * | 2016-10-20 | 2016-12-07 | Almac Discovery Limited | Pharmaceutical compounds |
| EP3571203B1 (en) | 2017-01-18 | 2023-06-07 | Array BioPharma Inc. | Substituted pyrazolo[1,5-a]pyrazine compounds as ret kinase inhibitors |
| US20200157081A1 (en) * | 2017-05-24 | 2020-05-21 | Denali Therapeutics Inc. | Compounds, compositions and methods |
| EP3668858A1 (en) | 2017-08-14 | 2020-06-24 | Pfizer Inc | Pyrazolo[1,5-a]pyrazin-4-yl and related derivatives |
| CN111615514B (zh) | 2018-01-18 | 2022-10-11 | 奥瑞生物药品公司 | 作为ret激酶抑制剂的取代的吡唑并[4,3-c]吡啶化合物 |
| CA3087578C (en) | 2018-01-18 | 2023-08-08 | Array Biopharma Inc. | Substituted pyrazolo[3,4-d]pyrimidine compounds as ret kinase inhibitors |
| TWI802635B (zh) | 2018-01-18 | 2023-05-21 | 美商亞雷生物製藥股份有限公司 | 作為ｒｅｔ激酶抑制劑之經取代吡咯并[2,3-d]嘧啶化合物 |
| ES2922314T3 (es) | 2018-09-10 | 2022-09-13 | Array Biopharma Inc | Compuestos heterocíclicos condensados como inhibidores de cinasa RET |
| CA3136468A1 (en) * | 2019-04-12 | 2020-10-15 | Primegene (Beijing) Co., Ltd. | Pyrazolopyrazine derived compounds and pharmaceutical compositions used as jak inhibitors |
| JOP20210298A1 (ar) | 2019-05-14 | 2023-01-30 | Provention Bio Inc | طرق وتركيبات للوقاية من مرض السكري من النوع الأول |
| CN113150012B (zh) * | 2020-01-22 | 2023-03-24 | 浙江海正药业股份有限公司 | 吡唑并[1,5-a]吡嗪类衍生物及其制备方法和用途 |
| CN115715194A (zh) | 2020-04-04 | 2023-02-24 | 辉瑞公司 | 治疗冠状病毒疾病2019的方法 |
| CA3237632A1 (en) * | 2021-11-12 | 2023-05-19 | Changqing WEI | Pyrazolo fused ring compound and use thereof |
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| IL141434A0 (en) | 1998-08-21 | 2002-03-10 | Parker Hughes Inst | Quinazoline derivatives |
| DE102007032349A1 (de) * | 2007-07-11 | 2009-01-15 | Bayer Healthcare Ag | Imidazo-, Pyrazolopyrazine und Imidazotriazine und ihre Verwendung |
| EA021568B1 (ru) * | 2009-12-23 | 2015-07-30 | Такеда Фармасьютикал Компани Лимитед | Конденсированные гетероароматические пирролидиноны как ингибиторы syk |
| ES2627703T3 (es) * | 2010-01-22 | 2017-07-31 | Fundación Centro Nacional De Investigaciones Oncológicas Carlos Iii | Inhibidores de PI3·quinasa |
| UY33213A (es) | 2010-02-18 | 2011-09-30 | Almirall Sa | Derivados de pirazol como inhibidores de jak |
| US20110241987A1 (en) * | 2010-04-01 | 2011-10-06 | Smart Technologies Ulc | Interactive input system and information input method therefor |
| SG184870A1 (en) | 2010-04-14 | 2012-11-29 | Array Biopharma Inc | 5, 7-substituted-imidazo [1, 2-c] pyrimidines as inhibitors of jak kinases |
| US20140228349A1 (en) * | 2011-10-12 | 2014-08-14 | Array Biopharma Inc. | 5,7-substituted-imidazo[1,2-c]pyrimidines |
| UA112795C2 (uk) * | 2012-03-28 | 2016-10-25 | Мерк Патент Гмбх | Біциклічні піразинонові похідні |
| CR20170309A (es) | 2014-12-05 | 2018-02-02 | Celgene Corp | Pirazolo [1,5-a] pirazinas 4,6-sustituidas como inhibidores de janus cinasas |
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