EA020461B1 - ИМИДАЗОПИРАЗИНОВЫЕ ИНГИБИТОРЫ Syk - Google Patents
ИМИДАЗОПИРАЗИНОВЫЕ ИНГИБИТОРЫ Syk Download PDFInfo
- Publication number
- EA020461B1 EA020461B1 EA201190042A EA201190042A EA020461B1 EA 020461 B1 EA020461 B1 EA 020461B1 EA 201190042 A EA201190042 A EA 201190042A EA 201190042 A EA201190042 A EA 201190042A EA 020461 B1 EA020461 B1 EA 020461B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- imidazo
- pyrazin
- phenyl
- amino
- amine
- Prior art date
Links
- 239000003112 inhibitor Substances 0.000 title description 3
- ZKAMEFMDQNTDFK-UHFFFAOYSA-N 1h-imidazo[4,5-b]pyrazine Chemical compound C1=CN=C2NC=NC2=N1 ZKAMEFMDQNTDFK-UHFFFAOYSA-N 0.000 title 1
- 230000000694 effects Effects 0.000 claims abstract description 75
- 238000000034 method Methods 0.000 claims abstract description 65
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 44
- 201000010099 disease Diseases 0.000 claims abstract description 40
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 181
- 210000004027 cell Anatomy 0.000 claims description 55
- 210000003719 b-lymphocyte Anatomy 0.000 claims description 46
- 108091000080 Phosphotransferase Proteins 0.000 claims description 36
- 102000020233 phosphotransferase Human genes 0.000 claims description 36
- 150000003839 salts Chemical class 0.000 claims description 32
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims description 25
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims description 25
- 102000001253 Protein Kinase Human genes 0.000 claims description 24
- 108060006633 protein kinase Proteins 0.000 claims description 24
- 230000001629 suppression Effects 0.000 claims description 23
- 206010028980 Neoplasm Diseases 0.000 claims description 19
- 208000027866 inflammatory disease Diseases 0.000 claims description 19
- 208000026935 allergic disease Diseases 0.000 claims description 18
- 201000011510 cancer Diseases 0.000 claims description 17
- 208000023275 Autoimmune disease Diseases 0.000 claims description 16
- 206010061218 Inflammation Diseases 0.000 claims description 12
- 230000004054 inflammatory process Effects 0.000 claims description 12
- 230000003993 interaction Effects 0.000 claims description 12
- 230000001154 acute effect Effects 0.000 claims description 11
- 208000003950 B-cell lymphoma Diseases 0.000 claims description 6
- 230000007062 hydrolysis Effects 0.000 claims description 6
- 238000006460 hydrolysis reaction Methods 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 206010020751 Hypersensitivity Diseases 0.000 claims description 4
- 206010039085 Rhinitis allergic Diseases 0.000 claims description 4
- 201000010105 allergic rhinitis Diseases 0.000 claims description 4
- 208000032839 leukemia Diseases 0.000 claims description 3
- 208000030761 polycystic kidney disease Diseases 0.000 claims description 3
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
- 208000024893 Acute lymphoblastic leukemia Diseases 0.000 claims description 2
- 208000014697 Acute lymphocytic leukaemia Diseases 0.000 claims description 2
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims description 2
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 2
- 208000004736 B-Cell Leukemia Diseases 0.000 claims description 2
- 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 claims description 2
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims description 2
- 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims description 2
- 208000017604 Hodgkin disease Diseases 0.000 claims description 2
- 208000021519 Hodgkin lymphoma Diseases 0.000 claims description 2
- 208000010747 Hodgkins lymphoma Diseases 0.000 claims description 2
- 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 claims description 2
- 208000034578 Multiple myelomas Diseases 0.000 claims description 2
- 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims description 2
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims description 2
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims description 2
- 206010035226 Plasma cell myeloma Diseases 0.000 claims description 2
- 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 claims description 2
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims description 2
- 239000002671 adjuvant Substances 0.000 claims description 2
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims description 2
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims description 2
- 230000007815 allergy Effects 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 208000032852 chronic lymphocytic leukemia Diseases 0.000 claims description 2
- 201000006417 multiple sclerosis Diseases 0.000 claims description 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 238000007918 intramuscular administration Methods 0.000 claims 1
- 238000001990 intravenous administration Methods 0.000 claims 1
- 238000007911 parenteral administration Methods 0.000 claims 1
- 208000024891 symptom Diseases 0.000 abstract description 15
- 230000005764 inhibitory process Effects 0.000 abstract description 7
- 208000035475 disorder Diseases 0.000 abstract description 4
- 102000000551 Syk Kinase Human genes 0.000 abstract description 3
- 108010016672 Syk Kinase Proteins 0.000 abstract description 3
- 150000005235 imidazopyrazines Chemical class 0.000 abstract description 2
- 150000005829 chemical entities Chemical class 0.000 abstract 1
- 208000037765 diseases and disorders Diseases 0.000 abstract 1
- -1 hydroxy, carboxy Chemical group 0.000 description 811
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 399
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 382
- 125000001424 substituent group Chemical group 0.000 description 228
- 125000000217 alkyl group Chemical group 0.000 description 195
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 138
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 104
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 100
- RZLXZEJRGRNLQR-UHFFFAOYSA-N imidazo[1,2-a]pyrazin-8-amine Chemical compound NC1=NC=CN2C=CN=C12 RZLXZEJRGRNLQR-UHFFFAOYSA-N 0.000 description 100
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 92
- 125000003545 alkoxy group Chemical group 0.000 description 86
- 229910052739 hydrogen Inorganic materials 0.000 description 86
- 239000001257 hydrogen Substances 0.000 description 85
- 125000001072 heteroaryl group Chemical group 0.000 description 75
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 69
- 125000003118 aryl group Chemical group 0.000 description 51
- 229910052736 halogen Inorganic materials 0.000 description 48
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 46
- 150000002367 halogens Chemical class 0.000 description 45
- 125000000753 cycloalkyl group Chemical group 0.000 description 38
- 125000003107 substituted aryl group Chemical group 0.000 description 38
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 32
- 150000002431 hydrogen Chemical class 0.000 description 31
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 28
- 125000004432 carbon atom Chemical group C* 0.000 description 27
- 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 description 26
- 125000004429 atom Chemical group 0.000 description 26
- 229910052757 nitrogen Inorganic materials 0.000 description 24
- 125000004043 oxo group Chemical group O=* 0.000 description 23
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 22
- 239000000203 mixture Substances 0.000 description 22
- 125000000547 substituted alkyl group Chemical group 0.000 description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- SDBQITCBKYNDMG-UHFFFAOYSA-N O1CCN(CC1)C1=CC=C(C=C1)C=1N=C2N(C=CN=C2N)C=1 Chemical compound O1CCN(CC1)C1=CC=C(C=C1)C=1N=C2N(C=CN=C2N)C=1 SDBQITCBKYNDMG-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 17
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 17
- 230000001363 autoimmune Effects 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 238000001994 activation Methods 0.000 description 14
- 125000004433 nitrogen atom Chemical group N* 0.000 description 14
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 13
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 13
- 230000004913 activation Effects 0.000 description 13
- 125000004076 pyridyl group Chemical group 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 13
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000002246 antineoplastic agent Substances 0.000 description 12
- 210000003630 histaminocyte Anatomy 0.000 description 12
- JHHZLHWJQPUNKB-UHFFFAOYSA-N pyrrolidin-3-ol Chemical compound OC1CCNC1 JHHZLHWJQPUNKB-UHFFFAOYSA-N 0.000 description 12
- 125000005605 benzo group Chemical group 0.000 description 11
- 125000005842 heteroatom Chemical group 0.000 description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 11
- 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 description 11
- 239000002244 precipitate Substances 0.000 description 11
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 11
- 108060003951 Immunoglobulin Proteins 0.000 description 10
- 210000001744 T-lymphocyte Anatomy 0.000 description 10
- 239000013543 active substance Substances 0.000 description 10
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 10
- 125000004093 cyano group Chemical group *C#N 0.000 description 10
- 102000018358 immunoglobulin Human genes 0.000 description 10
- 229910052760 oxygen Inorganic materials 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 208000006673 asthma Diseases 0.000 description 9
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 125000005553 heteroaryloxy group Chemical group 0.000 description 9
- 229940072221 immunoglobulins Drugs 0.000 description 9
- 239000001301 oxygen Substances 0.000 description 9
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- COXVTLYNGOIATD-HVMBLDELSA-N CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O Chemical compound CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O COXVTLYNGOIATD-HVMBLDELSA-N 0.000 description 8
- 102000004190 Enzymes Human genes 0.000 description 8
- 108090000790 Enzymes Proteins 0.000 description 8
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 8
- 125000002252 acyl group Chemical group 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 8
- 239000000427 antigen Substances 0.000 description 8
- 102000036639 antigens Human genes 0.000 description 8
- 108091007433 antigens Proteins 0.000 description 8
- GMWFCJXSQQHBPI-UHFFFAOYSA-N azetidin-3-ol Chemical compound OC1CNC1 GMWFCJXSQQHBPI-UHFFFAOYSA-N 0.000 description 8
- 239000001045 blue dye Substances 0.000 description 8
- 229940127089 cytotoxic agent Drugs 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 229960003699 evans blue Drugs 0.000 description 8
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 8
- 125000004193 piperazinyl group Chemical group 0.000 description 8
- BIWOSRSKDCZIFM-UHFFFAOYSA-N piperidin-3-ol Chemical compound OC1CCCNC1 BIWOSRSKDCZIFM-UHFFFAOYSA-N 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 230000008569 process Effects 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 7
- DRVWEZAUAUVZHY-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)imidazo[1,2-a]pyrazin-8-amine Chemical compound COC=1C=C(C=CC=1OC)C=1N=C2N(C=CN=C2N)C=1 DRVWEZAUAUVZHY-UHFFFAOYSA-N 0.000 description 7
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 7
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 230000000875 corresponding effect Effects 0.000 description 7
- 238000011161 development Methods 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 239000003814 drug Substances 0.000 description 7
- 125000002541 furyl group Chemical group 0.000 description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 7
- 230000035755 proliferation Effects 0.000 description 7
- 235000018102 proteins Nutrition 0.000 description 7
- 102000004169 proteins and genes Human genes 0.000 description 7
- 108090000623 proteins and genes Proteins 0.000 description 7
- 239000011780 sodium chloride Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 239000012453 solvate Substances 0.000 description 7
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 6
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 229940121363 anti-inflammatory agent Drugs 0.000 description 6
- 239000002260 anti-inflammatory agent Substances 0.000 description 6
- 238000003556 assay Methods 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 125000000068 chlorophenyl group Chemical group 0.000 description 6
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 6
- 230000001404 mediated effect Effects 0.000 description 6
- 239000013642 negative control Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- 102000005962 receptors Human genes 0.000 description 6
- 108020003175 receptors Proteins 0.000 description 6
- 230000035945 sensitivity Effects 0.000 description 6
- GPZCWXNACJWRDP-UHFFFAOYSA-N 2-(3-methoxy-4-morpholin-4-ylphenyl)imidazo[1,2-a]pyrazin-8-amine Chemical compound COC1=CC(C=2N=C3C(N)=NC=CN3C=2)=CC=C1N1CCOCC1 GPZCWXNACJWRDP-UHFFFAOYSA-N 0.000 description 5
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 5
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 5
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 5
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 5
- GXWNSJYVSIJRLS-UHFFFAOYSA-N 6-bromo-8-methylimidazo[1,2-a]pyrazine Chemical compound CC1=NC(Br)=CN2C=CN=C12 GXWNSJYVSIJRLS-UHFFFAOYSA-N 0.000 description 5
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- 241000699670 Mus sp. Species 0.000 description 5
- 206010070834 Sensitisation Diseases 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 5
- 230000007503 antigenic stimulation Effects 0.000 description 5
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 5
- 230000027455 binding Effects 0.000 description 5
- 210000004369 blood Anatomy 0.000 description 5
- 239000008280 blood Substances 0.000 description 5
- 239000011575 calcium Substances 0.000 description 5
- 125000002837 carbocyclic group Chemical group 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 125000004430 oxygen atom Chemical group O* 0.000 description 5
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 5
- 239000000651 prodrug Substances 0.000 description 5
- 229940002612 prodrug Drugs 0.000 description 5
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 5
- 125000000714 pyrimidinyl group Chemical group 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 230000008313 sensitization Effects 0.000 description 5
- 230000011664 signaling Effects 0.000 description 5
- 210000000952 spleen Anatomy 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 4
- UFBJCMHMOXMLKC-UHFFFAOYSA-N 2,4-dinitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O UFBJCMHMOXMLKC-UHFFFAOYSA-N 0.000 description 4
- KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical group COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 description 4
- XKMIZJKOZNOWBI-UHFFFAOYSA-N 2-(4-ethoxy-3-methoxyphenyl)imidazo[1,2-a]pyrazin-8-amine Chemical compound C(C)OC1=C(C=C(C=C1)C=1N=C2N(C=CN=C2N)C=1)OC XKMIZJKOZNOWBI-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 102000004127 Cytokines Human genes 0.000 description 4
- 108090000695 Cytokines Proteins 0.000 description 4
- 206010021245 Idiopathic thrombocytopenic purpura Diseases 0.000 description 4
- 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 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- 241000699666 Mus <mouse, genus> Species 0.000 description 4
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 4
- 102100038280 Prostaglandin G/H synthase 2 Human genes 0.000 description 4
- 108050003267 Prostaglandin G/H synthase 2 Proteins 0.000 description 4
- 208000031981 Thrombocytopenic Idiopathic Purpura Diseases 0.000 description 4
- IQFYYKKMVGJFEH-XLPZGREQSA-N Thymidine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 IQFYYKKMVGJFEH-XLPZGREQSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 4
- 125000004104 aryloxy group Chemical group 0.000 description 4
- 208000010668 atopic eczema Diseases 0.000 description 4
- 201000003710 autoimmune thrombocytopenic purpura Diseases 0.000 description 4
- 230000004663 cell proliferation Effects 0.000 description 4
- 238000002512 chemotherapy Methods 0.000 description 4
- 230000001684 chronic effect Effects 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 4
- 210000003979 eosinophil Anatomy 0.000 description 4
- 239000012634 fragment Substances 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 4
- MBVAHHOKMIRXLP-UHFFFAOYSA-N imidazo[1,2-a]pyrazine Chemical compound C1=CN=CC2=NC=CN21 MBVAHHOKMIRXLP-UHFFFAOYSA-N 0.000 description 4
- 125000000336 imidazol-5-yl group Chemical group [H]N1C([H])=NC([H])=C1[*] 0.000 description 4
- 238000011534 incubation Methods 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 102000006240 membrane receptors Human genes 0.000 description 4
- 108020004084 membrane receptors Proteins 0.000 description 4
- 229960000485 methotrexate Drugs 0.000 description 4
- 125000004572 morpholin-3-yl group Chemical group N1C(COCC1)* 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- 230000001717 pathogenic effect Effects 0.000 description 4
- RLZZZVKAURTHCP-UHFFFAOYSA-N phenanthrene-3,4-diol Chemical compound C1=CC=C2C3=C(O)C(O)=CC=C3C=CC2=C1 RLZZZVKAURTHCP-UHFFFAOYSA-N 0.000 description 4
- HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 4
- 230000004044 response Effects 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229940124597 therapeutic agent Drugs 0.000 description 4
- 125000001544 thienyl group Chemical group 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 3
- ZZLCFHIKESPLTH-UHFFFAOYSA-N 4-Methylbiphenyl Chemical compound C1=CC(C)=CC=C1C1=CC=CC=C1 ZZLCFHIKESPLTH-UHFFFAOYSA-N 0.000 description 3
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 description 3
- 102000019260 B-Cell Antigen Receptors Human genes 0.000 description 3
- 108010012919 B-Cell Antigen Receptors Proteins 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- 201000004624 Dermatitis Diseases 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 241000124008 Mammalia Species 0.000 description 3
- 102100036314 Mitochondrial cardiolipin hydrolase Human genes 0.000 description 3
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 3
- 229930012538 Paclitaxel Natural products 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- 239000000370 acceptor Substances 0.000 description 3
- 230000000172 allergic effect Effects 0.000 description 3
- 230000006907 apoptotic process Effects 0.000 description 3
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 3
- 210000001185 bone marrow Anatomy 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 239000003246 corticosteroid Substances 0.000 description 3
- 125000000000 cycloalkoxy group Chemical group 0.000 description 3
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 3
- 230000007812 deficiency Effects 0.000 description 3
- 125000005434 dihydrobenzoxazinyl group Chemical group O1N(CCC2=C1C=CC=C2)* 0.000 description 3
- 125000001070 dihydroindolyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 125000005805 dimethoxy phenyl group Chemical group 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 150000004677 hydrates Chemical class 0.000 description 3
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 3
- 230000001965 increasing effect Effects 0.000 description 3
- 102000006495 integrins Human genes 0.000 description 3
- 108010044426 integrins Proteins 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 229940043355 kinase inhibitor Drugs 0.000 description 3
- 210000001616 monocyte Anatomy 0.000 description 3
- 125000002757 morpholinyl group Chemical group 0.000 description 3
- 206010028417 myasthenia gravis Diseases 0.000 description 3
- 210000000440 neutrophil Anatomy 0.000 description 3
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 3
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 3
- 229960001592 paclitaxel Drugs 0.000 description 3
- 239000003757 phosphotransferase inhibitor Substances 0.000 description 3
- 238000002264 polyacrylamide gel electrophoresis Methods 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 3
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 125000006413 ring segment Chemical group 0.000 description 3
- 230000019491 signal transduction Effects 0.000 description 3
- 230000008054 signal transmission Effects 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 230000009870 specific binding Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 3
- 125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 description 3
- 229940104230 thymidine Drugs 0.000 description 3
- 210000001685 thyroid gland Anatomy 0.000 description 3
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 2
- MZOFCQQQCNRIBI-VMXHOPILSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[(1s)-1-carboxy-2-hydroxyethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-[[2-[[(2s)-2,6-diaminohexanoyl]amino]acetyl]amino]-4-oxobutanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)CCCCN MZOFCQQQCNRIBI-VMXHOPILSA-N 0.000 description 2
- 125000001401 1,2,4-triazol-4-yl group Chemical group N=1N=C([H])N([*])C=1[H] 0.000 description 2
- XXBQLHATYQHJQC-UHFFFAOYSA-N 1,2-dihydroquinoxaline Chemical compound C1=CC=C2N=CCNC2=C1 XXBQLHATYQHJQC-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- ZKHSBXSSIOGSQW-UHFFFAOYSA-N 1-[2-ethoxy-4-[[6-(1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenoxy]-2-methylpropan-2-ol Chemical compound C1=C(OCC(C)(C)O)C(OCC)=CC(NC=2C3=NC=CN3C=C(N=2)C=2C=C3NN=CC3=CC=2)=C1 ZKHSBXSSIOGSQW-UHFFFAOYSA-N 0.000 description 2
- XBNXYCGXBGBNCA-UHFFFAOYSA-N 1-[4-[[6-(1,3-benzothiazol-5-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenoxy]-2-methylpropan-2-ol Chemical compound C1=CC(OCC(C)(O)C)=CC=C1NC1=NC(C=2C=C3N=CSC3=CC=2)=CN2C1=NC=C2 XBNXYCGXBGBNCA-UHFFFAOYSA-N 0.000 description 2
- MZIHFSKRFQAHEQ-UHFFFAOYSA-N 1-[4-[[6-(1h-indazol-6-yl)-5-methylimidazo[1,2-a]pyrazin-8-yl]amino]phenyl]-4-methylpiperidin-4-ol Chemical compound C12=NC=CN2C(C)=C(C=2C=C3NN=CC3=CC=2)N=C1NC(C=C1)=CC=C1N1CCC(C)(O)CC1 MZIHFSKRFQAHEQ-UHFFFAOYSA-N 0.000 description 2
- JCRTTZHMBRJNGH-UHFFFAOYSA-N 1-[4-[[6-(1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]-3-methylazetidin-3-ol Chemical compound C1C(C)(O)CN1C(C=C1)=CC=C1NC1=NC(C=2C=C3NN=CC3=CC=2)=CN2C1=NC=C2 JCRTTZHMBRJNGH-UHFFFAOYSA-N 0.000 description 2
- QWMSRWRZVGCILT-UHFFFAOYSA-N 1-[4-[[6-(3,4-dihydro-2h-1,4-benzoxazin-7-yl)imidazo[1,2-a]pyrazin-8-yl]amino]-2-methoxyphenyl]-3-methylazetidin-3-ol Chemical compound COC1=CC(NC=2C3=NC=CN3C=C(N=2)C=2C=C3OCCNC3=CC=2)=CC=C1N1CC(C)(O)C1 QWMSRWRZVGCILT-UHFFFAOYSA-N 0.000 description 2
- HNEGJTWNOOWEMH-UHFFFAOYSA-N 1-fluoropropane Chemical group [CH2]CCF HNEGJTWNOOWEMH-UHFFFAOYSA-N 0.000 description 2
- HGYGQEMTQPHXFF-UHFFFAOYSA-N 2-[4-[[6-(1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]-2-methylpropan-1-ol Chemical compound C1=CC(C(C)(CO)C)=CC=C1NC1=NC(C=2C=C3NN=CC3=CC=2)=CN2C1=NC=C2 HGYGQEMTQPHXFF-UHFFFAOYSA-N 0.000 description 2
- CLMBDIYJGRLLPX-UHFFFAOYSA-N 2-[4-[[6-(1h-indol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]-2-methylpropan-1-ol Chemical compound C1=CC(C(C)(CO)C)=CC=C1NC1=NC(C=2C=C3NC=CC3=CC=2)=CN2C1=NC=C2 CLMBDIYJGRLLPX-UHFFFAOYSA-N 0.000 description 2
- KYMOHMAWUMTVOD-UHFFFAOYSA-N 2-[4-[[6-(2-aminoquinazolin-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]propan-2-ol Chemical compound C1=CC(C(C)(O)C)=CC=C1NC1=NC(C=2C=C3C=NC(N)=NC3=CC=2)=CN2C1=NC=C2 KYMOHMAWUMTVOD-UHFFFAOYSA-N 0.000 description 2
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 2
- KYSXEQIDERDCJO-UHFFFAOYSA-N 4-[[6-(1H-indazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]-2-methoxyphenol Chemical compound C1=C(O)C(OC)=CC(NC=2C3=NC=CN3C=C(N=2)C=2C=C3NN=CC3=CC=2)=C1 KYSXEQIDERDCJO-UHFFFAOYSA-N 0.000 description 2
- ILXLGLZNYYVJRC-UHFFFAOYSA-N 4-[[6-(1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]-2-methoxybenzoic acid Chemical compound C1=C(C(O)=O)C(OC)=CC(NC=2C3=NC=CN3C=C(N=2)C=2C=C3NN=CC3=CC=2)=C1 ILXLGLZNYYVJRC-UHFFFAOYSA-N 0.000 description 2
- 125000001054 5 membered carbocyclic group Chemical group 0.000 description 2
- 125000004008 6 membered carbocyclic group Chemical group 0.000 description 2
- LGYUOCBUROULQE-UHFFFAOYSA-N 6-[8-(3,4-dimethoxyanilino)imidazo[1,2-a]pyrazin-6-yl]quinazolin-2-amine Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC(C=2C=C3C=NC(N)=NC3=CC=2)=CN2C1=NC=C2 LGYUOCBUROULQE-UHFFFAOYSA-N 0.000 description 2
- CEOTZOPACDVNIN-UHFFFAOYSA-N 7-[8-(3,4-dimethoxyanilino)imidazo[1,2-a]pyrazin-6-yl]-1h-quinolin-2-one Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC(C=2C=C3N=C(O)C=CC3=CC=2)=CN2C1=NC=C2 CEOTZOPACDVNIN-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- 208000035285 Allergic Seasonal Rhinitis Diseases 0.000 description 2
- 206010002198 Anaphylactic reaction Diseases 0.000 description 2
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 2
- 206010003645 Atopy Diseases 0.000 description 2
- 108091008875 B cell receptors Proteins 0.000 description 2
- ZDPNBWXLCUTVDK-UHFFFAOYSA-N CC(CN1CCOCC1)(C)C1=CC=C(C=C1)C=1N=C2N(C=CN=C2N)C=1 Chemical compound CC(CN1CCOCC1)(C)C1=CC=C(C=C1)C=1N=C2N(C=CN=C2N)C=1 ZDPNBWXLCUTVDK-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 206010012434 Dermatitis allergic Diseases 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical group COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 208000004262 Food Hypersensitivity Diseases 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 206010018364 Glomerulonephritis Diseases 0.000 description 2
- DHCLVCXQIBBOPH-UHFFFAOYSA-N Glycerol 2-phosphate Chemical compound OCC(CO)OP(O)(O)=O DHCLVCXQIBBOPH-UHFFFAOYSA-N 0.000 description 2
- 102000002268 Hexosaminidases Human genes 0.000 description 2
- 108010000540 Hexosaminidases Proteins 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- 108010002386 Interleukin-3 Proteins 0.000 description 2
- 206010025323 Lymphomas Diseases 0.000 description 2
- NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 NWIBSHFKIJFRCO-WUDYKRTCSA-N 0.000 description 2
- OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 description 2
- 108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 description 2
- 101100192365 Rattus norvegicus Ptpn5 gene Proteins 0.000 description 2
- 208000036071 Rhinorrhea Diseases 0.000 description 2
- 206010039101 Rhinorrhoea Diseases 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 230000006052 T cell proliferation Effects 0.000 description 2
- 229920004890 Triton X-100 Polymers 0.000 description 2
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 2
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 description 2
- 208000024780 Urticaria Diseases 0.000 description 2
- 206010047115 Vasculitis Diseases 0.000 description 2
- SOUUDKBBZKQRRJ-UHFFFAOYSA-N [1-[4-[[6-(3,4-dihydro-2h-1,4-benzoxazin-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]piperidin-4-yl]methanol Chemical compound C1CC(CO)CCN1C(C=C1)=CC=C1NC1=NC(C=2C=C3NCCOC3=CC=2)=CN2C1=NC=C2 SOUUDKBBZKQRRJ-UHFFFAOYSA-N 0.000 description 2
- 229960001138 acetylsalicylic acid Drugs 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 102000035181 adaptor proteins Human genes 0.000 description 2
- 108091005764 adaptor proteins Proteins 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 230000036783 anaphylactic response Effects 0.000 description 2
- 208000003455 anaphylaxis Diseases 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 2
- 125000002393 azetidinyl group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 2
- 238000012742 biochemical analysis Methods 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 108091006004 biotinylated proteins Proteins 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000005018 casein Substances 0.000 description 2
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 2
- 235000021240 caseins Nutrition 0.000 description 2
- 230000005754 cellular signaling Effects 0.000 description 2
- 229940044683 chemotherapy drug Drugs 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 230000000295 complement effect Effects 0.000 description 2
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 2
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical group P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 2
- 231100000673 dose–response relationship Toxicity 0.000 description 2
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 2
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 2
- VJJPUSNTGOMMGY-MRVIYFEKSA-N etoposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 VJJPUSNTGOMMGY-MRVIYFEKSA-N 0.000 description 2
- 229960005420 etoposide Drugs 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 235000020932 food allergy Nutrition 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 description 2
- 150000002344 gold compounds Chemical class 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 2
- 230000028993 immune response Effects 0.000 description 2
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 2
- 125000002249 indol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([*])=C([H])C2=C1[H] 0.000 description 2
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 description 2
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 2
- 125000001041 indolyl group Chemical group 0.000 description 2
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 2
- 208000030603 inherited susceptibility to asthma Diseases 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 2
- 238000010253 intravenous injection Methods 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Substances CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- 229960000681 leflunomide Drugs 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 239000003550 marker Substances 0.000 description 2
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- SCJZROUUYWNPLH-UHFFFAOYSA-N n-(oxetan-3-yl)benzamide Chemical compound C=1C=CC=CC=1C(=O)NC1COC1 SCJZROUUYWNPLH-UHFFFAOYSA-N 0.000 description 2
- SBFGJTSNMVBWKL-UHFFFAOYSA-N n-[4-(1,1-dioxo-1,4-thiazinan-4-yl)phenyl]-6-(1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-amine Chemical compound C1CS(=O)(=O)CCN1C(C=C1)=CC=C1NC1=NC(C=2C=C3NN=CC3=CC=2)=CN2C1=NC=C2 SBFGJTSNMVBWKL-UHFFFAOYSA-N 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000021766 negative regulation of B cell proliferation Effects 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 210000002997 osteoclast Anatomy 0.000 description 2
- 125000002971 oxazolyl group Chemical group 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 230000008506 pathogenesis Effects 0.000 description 2
- 230000001575 pathological effect Effects 0.000 description 2
- 239000002953 phosphate buffered saline Substances 0.000 description 2
- 230000026731 phosphorylation Effects 0.000 description 2
- 238000006366 phosphorylation reaction Methods 0.000 description 2
- IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical compound O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 description 2
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 235000011056 potassium acetate Nutrition 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- LWQAKQPNRUCBMO-UHFFFAOYSA-N pyrido[2,3-b][1,4]oxazin-2-one Chemical compound C1=CC=C2[N]C(=O)COC2=N1 LWQAKQPNRUCBMO-UHFFFAOYSA-N 0.000 description 2
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 108091008598 receptor tyrosine kinases Proteins 0.000 description 2
- 102000027426 receptor tyrosine kinases Human genes 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 229960004641 rituximab Drugs 0.000 description 2
- 229960001860 salicylate Drugs 0.000 description 2
- 150000003873 salicylate salts Chemical group 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- 239000012679 serum free medium Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000010802 sludge Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 210000004988 splenocyte Anatomy 0.000 description 2
- 238000010186 staining Methods 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- 230000004936 stimulating effect Effects 0.000 description 2
- 230000000638 stimulation Effects 0.000 description 2
- 125000005415 substituted alkoxy group Chemical group 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Chemical group 0.000 description 2
- 230000004083 survival effect Effects 0.000 description 2
- 201000000596 systemic lupus erythematosus Diseases 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 208000000143 urethritis Diseases 0.000 description 2
- 210000002700 urine Anatomy 0.000 description 2
- 210000003462 vein Anatomy 0.000 description 2
- 229910052727 yttrium Inorganic materials 0.000 description 2
- IDGGWNBYMFCJGL-UHFFFAOYSA-N (3-hydroxy-3-methylazetidin-1-yl)-[4-[[6-(1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]methanone Chemical compound C1C(C)(O)CN1C(=O)C(C=C1)=CC=C1NC1=NC(C=2C=C3NN=CC3=CC=2)=CN2C1=NC=C2 IDGGWNBYMFCJGL-UHFFFAOYSA-N 0.000 description 1
- ZADABHKHWLAKSZ-UHFFFAOYSA-N (3-hydroxyazetidin-1-yl)-[4-[[6-(1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]methanone Chemical compound C1C(O)CN1C(=O)C(C=C1)=CC=C1NC1=NC(C=2C=C3NN=CC3=CC=2)=CN2C1=NC=C2 ZADABHKHWLAKSZ-UHFFFAOYSA-N 0.000 description 1
- CJXKGNBICCKMMI-OEAKJJBVSA-N (3e)-6-[8-(4-morpholin-4-ylanilino)imidazo[1,2-a]pyrazin-6-yl]-3-(1,3-thiazol-4-ylmethylidene)-1h-indol-2-one Chemical compound O=C1NC2=CC(C=3N=C(NC=4C=CC(=CC=4)N4CCOCC4)C4=NC=CN4C=3)=CC=C2\C1=C/C1=CSC=N1 CJXKGNBICCKMMI-OEAKJJBVSA-N 0.000 description 1
- ABRYGPBWCWUDPJ-UHFFFAOYSA-N (4-hydroxy-4-methylpiperidin-1-yl)-[4-[[6-(1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]methanone Chemical compound C1CC(C)(O)CCN1C(=O)C(C=C1)=CC=C1NC1=NC(C=2C=C3NN=CC3=CC=2)=CN2C1=NC=C2 ABRYGPBWCWUDPJ-UHFFFAOYSA-N 0.000 description 1
- ZHZKCUHKDCSTSX-UHFFFAOYSA-N (4-hydroxypiperidin-1-yl)-[4-[[6-(1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]methanone Chemical compound C1CC(O)CCN1C(=O)C(C=C1)=CC=C1NC1=NC(C=2C=C3NN=CC3=CC=2)=CN2C1=NC=C2 ZHZKCUHKDCSTSX-UHFFFAOYSA-N 0.000 description 1
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 description 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
- NKXDGSARPYXHJN-UHFFFAOYSA-N 1,1,1-trifluoro-2-[4-[[6-(1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]propan-2-ol Chemical compound C1=CC(C(O)(C)C(F)(F)F)=CC=C1NC1=NC(C=2C=C3NN=CC3=CC=2)=CN2C1=NC=C2 NKXDGSARPYXHJN-UHFFFAOYSA-N 0.000 description 1
- BVVHNDKLDKPYCI-UHFFFAOYSA-N 1,2-dimethylpiperidin-4-amine Chemical compound CC1CC(N)CCN1C BVVHNDKLDKPYCI-UHFFFAOYSA-N 0.000 description 1
- ZYOWASBWJCTGLE-UHFFFAOYSA-N 1,3-dimethyl-5-[8-(4-morpholin-4-ylanilino)imidazo[1,2-a]pyrazin-6-yl]benzimidazol-2-one Chemical compound C1=C2N(C)C(=O)N(C)C2=CC=C1C(N=1)=CN2C=CN=C2C=1NC(C=C1)=CC=C1N1CCOCC1 ZYOWASBWJCTGLE-UHFFFAOYSA-N 0.000 description 1
- MENHXVNCWVKFRA-UHFFFAOYSA-N 1,4-oxazin-2-one Chemical compound O=C1C=NC=CO1 MENHXVNCWVKFRA-UHFFFAOYSA-N 0.000 description 1
- APGYUIAOXXIZSP-UHFFFAOYSA-N 1-[2-ethoxy-4-[[6-(1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]-3-methylazetidin-3-ol Chemical compound CCOC1=CC(NC=2C3=NC=CN3C=C(N=2)C=2C=C3NN=CC3=CC=2)=CC=C1N1CC(C)(O)C1 APGYUIAOXXIZSP-UHFFFAOYSA-N 0.000 description 1
- WGJBVRJUESXACC-UHFFFAOYSA-N 1-[2-ethoxy-4-[[6-(1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]-4-methylpiperidin-4-ol Chemical compound CCOC1=CC(NC=2C3=NC=CN3C=C(N=2)C=2C=C3NN=CC3=CC=2)=CC=C1N1CCC(C)(O)CC1 WGJBVRJUESXACC-UHFFFAOYSA-N 0.000 description 1
- BXSVMISGDZHJJQ-UHFFFAOYSA-N 1-[2-ethoxy-4-[[6-(1h-pyrrolo[3,2-b]pyridin-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]-3-methylazetidin-3-ol Chemical compound CCOC1=CC(NC=2C3=NC=CN3C=C(N=2)C=2C=C3NC=CC3=NC=2)=CC=C1N1CC(C)(O)C1 BXSVMISGDZHJJQ-UHFFFAOYSA-N 0.000 description 1
- UFMQDCIJRPWZII-UHFFFAOYSA-N 1-[2-methoxy-4-[[6-(1h-pyrrolo[3,2-b]pyridin-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]-3-methylazetidin-3-ol Chemical compound COC1=CC(NC=2C3=NC=CN3C=C(N=2)C=2C=C3NC=CC3=NC=2)=CC=C1N1CC(C)(O)C1 UFMQDCIJRPWZII-UHFFFAOYSA-N 0.000 description 1
- SMKRPVCOKHYANK-UHFFFAOYSA-N 1-[4-[4-[[6-(1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC(C=2C=C3NN=CC3=CC=2)=CN2C1=NC=C2 SMKRPVCOKHYANK-UHFFFAOYSA-N 0.000 description 1
- VYTKPTQGZOXZRU-UHFFFAOYSA-N 1-[4-[4-[[6-(1h-pyrrolo[3,2-b]pyridin-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC(C=2C=C3NC=CC3=NC=2)=CN2C1=NC=C2 VYTKPTQGZOXZRU-UHFFFAOYSA-N 0.000 description 1
- WRVZYHUHBLXLRY-UHFFFAOYSA-N 1-[4-[[3-[8-(3,4-dimethoxyanilino)imidazo[1,2-a]pyrazin-6-yl]phenyl]methyl]piperazin-1-yl]ethanone Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC(C=2C=C(CN3CCN(CC3)C(C)=O)C=CC=2)=CN2C1=NC=C2 WRVZYHUHBLXLRY-UHFFFAOYSA-N 0.000 description 1
- JACYZNJJRPLUMM-UHFFFAOYSA-N 1-[4-[[6-(1,3-benzothiazol-5-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]-3-methylazetidin-3-ol Chemical compound C1C(C)(O)CN1C(C=C1)=CC=C1NC1=NC(C=2C=C3N=CSC3=CC=2)=CN2C1=NC=C2 JACYZNJJRPLUMM-UHFFFAOYSA-N 0.000 description 1
- FIHTVCLYXUFXGQ-UHFFFAOYSA-N 1-[4-[[6-(1,3-benzothiazol-5-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]ethanol Chemical compound C1=CC(C(O)C)=CC=C1NC1=NC(C=2C=C3N=CSC3=CC=2)=CN2C1=NC=C2 FIHTVCLYXUFXGQ-UHFFFAOYSA-N 0.000 description 1
- GUSYTZBPDRXDSN-UHFFFAOYSA-N 1-[4-[[6-(1-methylbenzimidazol-5-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]azetidin-3-ol Chemical compound C=1C=C2N(C)C=NC2=CC=1C(N=1)=CN2C=CN=C2C=1NC(C=C1)=CC=C1N1CC(O)C1 GUSYTZBPDRXDSN-UHFFFAOYSA-N 0.000 description 1
- BSMPRAJJJFWHNJ-UHFFFAOYSA-N 1-[4-[[6-(1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]-2-methoxyphenyl]-2-methylpropan-2-ol Chemical compound C1=C(CC(C)(C)O)C(OC)=CC(NC=2C3=NC=CN3C=C(N=2)C=2C=C3NN=CC3=CC=2)=C1 BSMPRAJJJFWHNJ-UHFFFAOYSA-N 0.000 description 1
- DGCDZUQEXTWYIJ-UHFFFAOYSA-N 1-[4-[[6-(1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]-2-methoxyphenyl]-3-methylpiperidin-3-ol Chemical compound COC1=CC(NC=2C3=NC=CN3C=C(N=2)C=2C=C3NN=CC3=CC=2)=CC=C1N1CCCC(C)(O)C1 DGCDZUQEXTWYIJ-UHFFFAOYSA-N 0.000 description 1
- CHFHZJRVDQBYRH-UHFFFAOYSA-N 1-[4-[[6-(1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]-2-methoxyphenyl]piperidin-4-ol Chemical compound COC1=CC(NC=2C3=NC=CN3C=C(N=2)C=2C=C3NN=CC3=CC=2)=CC=C1N1CCC(O)CC1 CHFHZJRVDQBYRH-UHFFFAOYSA-N 0.000 description 1
- TVAJOTQMKIVNEK-UHFFFAOYSA-N 1-[4-[[6-(1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]-2-methoxyphenyl]pyrrolidin-3-ol Chemical compound COC1=CC(NC=2C3=NC=CN3C=C(N=2)C=2C=C3NN=CC3=CC=2)=CC=C1N1CCC(O)C1 TVAJOTQMKIVNEK-UHFFFAOYSA-N 0.000 description 1
- NKSWLLOMMDUYDD-UHFFFAOYSA-N 1-[4-[[6-(1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenoxy]-2-methylpropan-2-ol Chemical compound C1=CC(OCC(C)(O)C)=CC=C1NC1=NC(C=2C=C3NN=CC3=CC=2)=CN2C1=NC=C2 NKSWLLOMMDUYDD-UHFFFAOYSA-N 0.000 description 1
- BSCJQUPPRHKLPH-UHFFFAOYSA-N 1-[4-[[6-(1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]-2-methylpropan-2-ol Chemical compound C1=CC(CC(C)(O)C)=CC=C1NC1=NC(C=2C=C3NN=CC3=CC=2)=CN2C1=NC=C2 BSCJQUPPRHKLPH-UHFFFAOYSA-N 0.000 description 1
- PRFXFFBSCJDVDB-UHFFFAOYSA-N 1-[4-[[6-(1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]azetidin-3-ol Chemical compound C1C(O)CN1C(C=C1)=CC=C1NC1=NC(C=2C=C3NN=CC3=CC=2)=CN2C1=NC=C2 PRFXFFBSCJDVDB-UHFFFAOYSA-N 0.000 description 1
- OSULUCASRSCHKW-UHFFFAOYSA-N 1-[4-[[6-(1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]ethanol Chemical compound C1=CC(C(O)C)=CC=C1NC1=NC(C=2C=C3NN=CC3=CC=2)=CN2C1=NC=C2 OSULUCASRSCHKW-UHFFFAOYSA-N 0.000 description 1
- WHCBWMLTXCJSPT-UHFFFAOYSA-N 1-[4-[[6-(1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]piperidin-3-ol Chemical compound C1C(O)CCCN1C(C=C1)=CC=C1NC1=NC(C=2C=C3NN=CC3=CC=2)=CN2C1=NC=C2 WHCBWMLTXCJSPT-UHFFFAOYSA-N 0.000 description 1
- MVFUKEDXDPGCIO-UHFFFAOYSA-N 1-[4-[[6-(1h-indol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]-4-methylpiperidin-4-ol Chemical compound C1CC(C)(O)CCN1C(C=C1)=CC=C1NC1=NC(C=2C=C3NC=CC3=CC=2)=CN2C1=NC=C2 MVFUKEDXDPGCIO-UHFFFAOYSA-N 0.000 description 1
- XIIXLFMNNDWBRS-UHFFFAOYSA-N 1-[4-[[6-(3,4-dihydro-2h-1,4-benzoxazin-6-yl)-5-methylimidazo[1,2-a]pyrazin-8-yl]amino]phenyl]-4-methylpiperidin-4-ol Chemical compound C12=NC=CN2C(C)=C(C=2C=C3NCCOC3=CC=2)N=C1NC(C=C1)=CC=C1N1CCC(C)(O)CC1 XIIXLFMNNDWBRS-UHFFFAOYSA-N 0.000 description 1
- QXVKEXJEXLDUPP-UHFFFAOYSA-N 1-[4-[[6-(3,4-dihydro-2h-1,4-benzoxazin-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]-2-methylpropan-2-ol Chemical compound C1=CC(CC(C)(O)C)=CC=C1NC1=NC(C=2C=C3NCCOC3=CC=2)=CN2C1=NC=C2 QXVKEXJEXLDUPP-UHFFFAOYSA-N 0.000 description 1
- AZZFKFRWYBQPLP-UHFFFAOYSA-N 1-[4-[[6-(3,4-dihydro-2h-1,4-benzoxazin-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]-3-methylazetidin-3-ol Chemical compound C1C(C)(O)CN1C(C=C1)=CC=C1NC1=NC(C=2C=C3NCCOC3=CC=2)=CN2C1=NC=C2 AZZFKFRWYBQPLP-UHFFFAOYSA-N 0.000 description 1
- RZOOBTFHCRDUGI-UHFFFAOYSA-N 1-[4-[[6-(3,4-dihydro-2h-1,4-benzoxazin-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]-4-methylpiperidin-4-ol Chemical compound C1CC(C)(O)CCN1C(C=C1)=CC=C1NC1=NC(C=2C=C3NCCOC3=CC=2)=CN2C1=NC=C2 RZOOBTFHCRDUGI-UHFFFAOYSA-N 0.000 description 1
- QBZKVMCYVVKEQH-UHFFFAOYSA-N 1-[4-[[6-(3,4-dihydro-2h-1,4-benzoxazin-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]azetidin-3-ol Chemical compound C1C(O)CN1C(C=C1)=CC=C1NC1=NC(C=2C=C3NCCOC3=CC=2)=CN2C1=NC=C2 QBZKVMCYVVKEQH-UHFFFAOYSA-N 0.000 description 1
- WRACEHXZRGIWCG-UHFFFAOYSA-N 1-[4-[[6-(3,4-dihydro-2h-1,4-benzoxazin-7-yl)imidazo[1,2-a]pyrazin-8-yl]amino]-2-methoxyphenyl]-4-methylpiperidin-4-ol Chemical compound COC1=CC(NC=2C3=NC=CN3C=C(N=2)C=2C=C3OCCNC3=CC=2)=CC=C1N1CCC(C)(O)CC1 WRACEHXZRGIWCG-UHFFFAOYSA-N 0.000 description 1
- NWOJAFPWGLJBOH-UHFFFAOYSA-N 1-[4-[[6-(3,4-dihydro-2h-1,4-benzoxazin-7-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]azetidin-3-ol Chemical compound C1C(O)CN1C(C=C1)=CC=C1NC1=NC(C=2C=C3OCCNC3=CC=2)=CN2C1=NC=C2 NWOJAFPWGLJBOH-UHFFFAOYSA-N 0.000 description 1
- WMDJRIJNPQMOCL-UHFFFAOYSA-N 1-[4-[[6-(3-amino-1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]ethanol Chemical compound C1=CC(C(O)C)=CC=C1NC1=NC(C=2C=C3NN=C(N)C3=CC=2)=CN2C1=NC=C2 WMDJRIJNPQMOCL-UHFFFAOYSA-N 0.000 description 1
- SLMYNHAFSHHFIZ-UHFFFAOYSA-N 1-[4-[[6-(3-methylbenzimidazol-5-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]azetidin-3-ol Chemical compound C1=C2N(C)C=NC2=CC=C1C(N=1)=CN2C=CN=C2C=1NC(C=C1)=CC=C1N1CC(O)C1 SLMYNHAFSHHFIZ-UHFFFAOYSA-N 0.000 description 1
- KHFDTLAJZJVICQ-UHFFFAOYSA-N 1-[4-[[6-(3h-benzimidazol-5-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]-2-methylpropan-2-ol Chemical compound C1=CC(CC(C)(O)C)=CC=C1NC1=NC(C=2C=C3NC=NC3=CC=2)=CN2C1=NC=C2 KHFDTLAJZJVICQ-UHFFFAOYSA-N 0.000 description 1
- OLTOGSZPGWXVDV-UHFFFAOYSA-N 1-[4-[[6-(3h-benzimidazol-5-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]-4-methylpiperidin-4-ol Chemical compound C1CC(C)(O)CCN1C(C=C1)=CC=C1NC1=NC(C=2C=C3NC=NC3=CC=2)=CN2C1=NC=C2 OLTOGSZPGWXVDV-UHFFFAOYSA-N 0.000 description 1
- DEZNQRKQIIYXQG-UHFFFAOYSA-N 1-[4-[[6-(4-fluoro-1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]-3-methylazetidin-3-ol Chemical compound C1C(C)(O)CN1C(C=C1)=CC=C1NC1=NC(C=2C=C3NN=CC3=C(F)C=2)=CN2C1=NC=C2 DEZNQRKQIIYXQG-UHFFFAOYSA-N 0.000 description 1
- AJWKCIPIMZGCHN-UHFFFAOYSA-N 1-[4-[[6-(4-fluoro-1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]-4-methylpiperidin-4-ol Chemical compound C1CC(C)(O)CCN1C(C=C1)=CC=C1NC1=NC(C=2C=C3NN=CC3=C(F)C=2)=CN2C1=NC=C2 AJWKCIPIMZGCHN-UHFFFAOYSA-N 0.000 description 1
- ZTBOPNOFTLVYOK-UHFFFAOYSA-N 1-[4-[[6-[3-(2-hydroxyethyl)-2h-indazol-6-yl]imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]-3-methylazetidin-3-ol Chemical compound C1C(C)(O)CN1C(C=C1)=CC=C1NC1=NC(C=2C=C3NN=C(CCO)C3=CC=2)=CN2C1=NC=C2 ZTBOPNOFTLVYOK-UHFFFAOYSA-N 0.000 description 1
- URQPWBFOJSDULV-UHFFFAOYSA-N 1-[6-(1,3-benzothiazol-5-yl)imidazo[1,2-a]pyridin-8-yl]-3-ethylurea Chemical compound C1=C2SC=NC2=CC(C=2C=C(C3=NC=CN3C=2)NC(=O)NCC)=C1 URQPWBFOJSDULV-UHFFFAOYSA-N 0.000 description 1
- OOKYPWPVOLMIEP-UHFFFAOYSA-N 1-[6-(1,3-benzothiazol-5-yl)imidazo[1,2-a]pyridin-8-yl]-3-methylurea Chemical compound C1=C2SC=NC2=CC(C=2C=C(C3=NC=CN3C=2)NC(=O)NC)=C1 OOKYPWPVOLMIEP-UHFFFAOYSA-N 0.000 description 1
- KAPSPWKHLGXXNW-UHFFFAOYSA-N 1-[6-[8-(4-morpholin-4-ylanilino)imidazo[1,2-a]pyrazin-6-yl]-2h-indazol-3-yl]ethanol Chemical compound C=1C=C2C(C(O)C)=NNC2=CC=1C(N=1)=CN2C=CN=C2C=1NC(C=C1)=CC=C1N1CCOCC1 KAPSPWKHLGXXNW-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- VPUAYOJTHRDUTK-UHFFFAOYSA-N 1-ethylpyrrole Chemical compound CCN1C=CC=C1 VPUAYOJTHRDUTK-UHFFFAOYSA-N 0.000 description 1
- 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 description 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- FUFLCEKSBBHCMO-UHFFFAOYSA-N 11-dehydrocorticosterone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 FUFLCEKSBBHCMO-UHFFFAOYSA-N 0.000 description 1
- DITBWPUMEUDVLU-UHFFFAOYSA-N 1h-indazole-3-carboxamide Chemical compound C1=CC=C2C(C(=O)N)=NNC2=C1 DITBWPUMEUDVLU-UHFFFAOYSA-N 0.000 description 1
- LSGKMZLPZFPAIN-UHFFFAOYSA-N 1h-indole-3-carboxamide Chemical compound C1=CC=C2C(C(=O)N)=CNC2=C1 LSGKMZLPZFPAIN-UHFFFAOYSA-N 0.000 description 1
- PSXWKKPUOHRJLO-UHFFFAOYSA-N 2,2,2-trifluoro-1-[4-[[6-(1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]ethanol Chemical compound C1=CC(C(O)C(F)(F)F)=CC=C1NC1=NC(C=2C=C3NN=CC3=CC=2)=CN2C1=NC=C2 PSXWKKPUOHRJLO-UHFFFAOYSA-N 0.000 description 1
- LFEXGBPVZBXATF-UHFFFAOYSA-N 2,3-dimethylbenzenesulfonamide Chemical compound CC1=CC=CC(S(N)(=O)=O)=C1C LFEXGBPVZBXATF-UHFFFAOYSA-N 0.000 description 1
- CFMBMZPRXSWWIY-UHFFFAOYSA-N 2-(4-methoxyphenyl)imidazo[1,2-a]pyrazin-8-amine Chemical compound COc1ccc(cc1)c2cn3ccnc(N)c3n2 CFMBMZPRXSWWIY-UHFFFAOYSA-N 0.000 description 1
- ZEZIRBUTVZWDNZ-UHFFFAOYSA-N 2-[1-[4-[[6-(1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]piperidin-4-yl]ethanol Chemical compound C1CC(CCO)CCN1C(C=C1)=CC=C1NC1=NC(C=2C=C3NN=CC3=CC=2)=CN2C1=NC=C2 ZEZIRBUTVZWDNZ-UHFFFAOYSA-N 0.000 description 1
- RLWUFLMAXSLNQD-UHFFFAOYSA-N 2-[1-[4-[[6-(1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]piperidin-4-yl]propan-2-ol Chemical compound C1CC(C(C)(O)C)CCN1C(C=C1)=CC=C1NC1=NC(C=2C=C3NN=CC3=CC=2)=CN2C1=NC=C2 RLWUFLMAXSLNQD-UHFFFAOYSA-N 0.000 description 1
- YYWNZPVESZBNCP-UHFFFAOYSA-N 2-[1-[4-[[6-(1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]pyrrolidin-3-yl]ethanol Chemical compound C1C(CCO)CCN1C(C=C1)=CC=C1NC1=NC(C=2C=C3NN=CC3=CC=2)=CN2C1=NC=C2 YYWNZPVESZBNCP-UHFFFAOYSA-N 0.000 description 1
- HGBBGARATRRTGH-UHFFFAOYSA-N 2-[1-[4-[[6-(1h-pyrrolo[3,2-b]pyridin-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]piperidin-4-yl]ethanol Chemical compound C1CC(CCO)CCN1C(C=C1)=CC=C1NC1=NC(C=2C=C3NC=CC3=NC=2)=CN2C1=NC=C2 HGBBGARATRRTGH-UHFFFAOYSA-N 0.000 description 1
- DKLMACBVVUXAQB-UHFFFAOYSA-N 2-[1-[4-[[6-(3,4-dihydro-2h-1,4-benzoxazin-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]piperidin-4-yl]ethanol Chemical compound C1CC(CCO)CCN1C(C=C1)=CC=C1NC1=NC(C=2C=C3NCCOC3=CC=2)=CN2C1=NC=C2 DKLMACBVVUXAQB-UHFFFAOYSA-N 0.000 description 1
- NEZDGLBYSFHDCD-UHFFFAOYSA-N 2-[2-ethoxy-4-[[6-(1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]-n-methylanilino]ethanol Chemical compound C1=C(N(C)CCO)C(OCC)=CC(NC=2C3=NC=CN3C=C(N=2)C=2C=C3NN=CC3=CC=2)=C1 NEZDGLBYSFHDCD-UHFFFAOYSA-N 0.000 description 1
- PSDSUCBGSUANHG-UHFFFAOYSA-N 2-[2-morpholin-4-yl-5-[[6-(1h-pyrrolo[3,2-b]pyridin-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenoxy]ethanol Chemical compound OCCOC1=CC(NC=2C3=NC=CN3C=C(N=2)C=2C=C3NC=CC3=NC=2)=CC=C1N1CCOCC1 PSDSUCBGSUANHG-UHFFFAOYSA-N 0.000 description 1
- LDTIGVNRVKGRGE-UHFFFAOYSA-N 2-[4-[2-methoxy-4-[[6-(1h-pyrrolo[3,2-b]pyridin-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]piperazin-1-yl]ethanol Chemical compound COC1=CC(NC=2C3=NC=CN3C=C(N=2)C=2C=C3NC=CC3=NC=2)=CC=C1N1CCN(CCO)CC1 LDTIGVNRVKGRGE-UHFFFAOYSA-N 0.000 description 1
- AIYHFERBBAMTOF-UHFFFAOYSA-N 2-[4-[4-[[6-(1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]piperazin-1-yl]ethanol Chemical compound C1CN(CCO)CCN1C(C=C1)=CC=C1NC1=NC(C=2C=C3NN=CC3=CC=2)=CN2C1=NC=C2 AIYHFERBBAMTOF-UHFFFAOYSA-N 0.000 description 1
- KXLYJXVAURHVHI-UHFFFAOYSA-N 2-[4-[[6-(1,3-benzothiazol-5-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]propan-2-ol Chemical compound C1=CC(C(C)(O)C)=CC=C1NC1=NC(C=2C=C3N=CSC3=CC=2)=CN2C1=NC=C2 KXLYJXVAURHVHI-UHFFFAOYSA-N 0.000 description 1
- HQOWHYORRCMCOS-UHFFFAOYSA-N 2-[4-[[6-(1,4-dimethyl-2,3-dihydroquinoxalin-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]propan-2-ol Chemical compound C=1C=C2N(C)CCN(C)C2=CC=1C(N=1)=CN2C=CN=C2C=1NC1=CC=C(C(C)(C)O)C=C1 HQOWHYORRCMCOS-UHFFFAOYSA-N 0.000 description 1
- YKUOLQADMZPWLL-UHFFFAOYSA-N 2-[4-[[6-(1-methylbenzimidazol-5-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]propan-2-ol Chemical compound C=1C=C2N(C)C=NC2=CC=1C(N=1)=CN2C=CN=C2C=1NC1=CC=C(C(C)(C)O)C=C1 YKUOLQADMZPWLL-UHFFFAOYSA-N 0.000 description 1
- VGTMBHPNGANXBY-UHFFFAOYSA-N 2-[4-[[6-(1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]-2-methoxy-n-methylanilino]ethanol Chemical compound C1=C(N(C)CCO)C(OC)=CC(NC=2C3=NC=CN3C=C(N=2)C=2C=C3NN=CC3=CC=2)=C1 VGTMBHPNGANXBY-UHFFFAOYSA-N 0.000 description 1
- ZSSHHWNMBCTZSS-UHFFFAOYSA-N 2-[4-[[6-(1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]-n-methylanilino]ethanol Chemical compound C1=CC(N(CCO)C)=CC=C1NC1=NC(C=2C=C3NN=CC3=CC=2)=CN2C1=NC=C2 ZSSHHWNMBCTZSS-UHFFFAOYSA-N 0.000 description 1
- YWTBJPRZMXIMJZ-UHFFFAOYSA-N 2-[4-[[6-(1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenoxy]acetic acid Chemical compound C1=CC(OCC(=O)O)=CC=C1NC1=NC(C=2C=C3NN=CC3=CC=2)=CN2C1=NC=C2 YWTBJPRZMXIMJZ-UHFFFAOYSA-N 0.000 description 1
- OBKZVHYLQTXERY-UHFFFAOYSA-N 2-[4-[[6-(1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenoxy]ethanol Chemical compound C1=CC(OCCO)=CC=C1NC1=NC(C=2C=C3NN=CC3=CC=2)=CN2C1=NC=C2 OBKZVHYLQTXERY-UHFFFAOYSA-N 0.000 description 1
- LQGJWIMHSQVHER-UHFFFAOYSA-N 2-[4-[[6-(1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]propan-2-ol Chemical compound C1=CC(C(C)(O)C)=CC=C1NC1=NC(C=2C=C3NN=CC3=CC=2)=CN2C1=NC=C2 LQGJWIMHSQVHER-UHFFFAOYSA-N 0.000 description 1
- FNQKLXIZGXDHEX-UHFFFAOYSA-N 2-[4-[[6-(1h-indol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]propan-2-ol Chemical compound C1=CC(C(C)(O)C)=CC=C1NC1=NC(C=2C=C3NC=CC3=CC=2)=CN2C1=NC=C2 FNQKLXIZGXDHEX-UHFFFAOYSA-N 0.000 description 1
- CTGHRPSEDDGKHI-UHFFFAOYSA-N 2-[4-[[6-(2,3-dihydro-1h-indol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]propan-2-ol Chemical compound C1=CC(C(C)(O)C)=CC=C1NC1=NC(C=2C=C3NCCC3=CC=2)=CN2C1=NC=C2 CTGHRPSEDDGKHI-UHFFFAOYSA-N 0.000 description 1
- FDKRCLVTKJWFQX-UHFFFAOYSA-N 2-[4-[[6-(2,3-dimethylindazol-5-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]propan-2-ol Chemical compound C=1C2=C(C)N(C)N=C2C=CC=1C(N=1)=CN2C=CN=C2C=1NC1=CC=C(C(C)(C)O)C=C1 FDKRCLVTKJWFQX-UHFFFAOYSA-N 0.000 description 1
- TUKIBVPQMFWARR-UHFFFAOYSA-N 2-[4-[[6-(3,4-dihydro-2h-1,4-benzoxazin-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]propan-2-ol Chemical compound C1=CC(C(C)(O)C)=CC=C1NC1=NC(C=2C=C3NCCOC3=CC=2)=CN2C1=NC=C2 TUKIBVPQMFWARR-UHFFFAOYSA-N 0.000 description 1
- WSNQXCIRHUKPDJ-UHFFFAOYSA-N 2-[4-[[6-(3,4-dihydro-2h-1,4-benzoxazin-7-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]propan-2-ol Chemical compound C1=CC(C(C)(O)C)=CC=C1NC1=NC(C=2C=C3OCCNC3=CC=2)=CN2C1=NC=C2 WSNQXCIRHUKPDJ-UHFFFAOYSA-N 0.000 description 1
- GXGLUFIEWHHVGF-UHFFFAOYSA-N 2-[4-[[6-(3-amino-1h-indazol-5-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]-2-methylpropan-1-ol Chemical compound C1=CC(C(C)(CO)C)=CC=C1NC1=NC(C=2C=C3C(N)=NNC3=CC=2)=CN2C1=NC=C2 GXGLUFIEWHHVGF-UHFFFAOYSA-N 0.000 description 1
- GLGLKQCVKHOIBR-UHFFFAOYSA-N 2-[4-[[6-(3-amino-1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]-2-methylpropan-1-ol Chemical compound C1=CC(C(C)(CO)C)=CC=C1NC1=NC(C=2C=C3NN=C(N)C3=CC=2)=CN2C1=NC=C2 GLGLKQCVKHOIBR-UHFFFAOYSA-N 0.000 description 1
- RSSPVENMNXRZAW-UHFFFAOYSA-N 2-[4-[[6-(3-methyl-2h-indazol-5-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]propan-2-ol Chemical compound C1=C2C(C)=NNC2=CC=C1C(N=1)=CN2C=CN=C2C=1NC1=CC=C(C(C)(C)O)C=C1 RSSPVENMNXRZAW-UHFFFAOYSA-N 0.000 description 1
- VKKBMXFKDVGDIT-UHFFFAOYSA-N 2-[4-[[6-(3-methylbenzimidazol-5-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]propan-2-ol Chemical compound C1=C2N(C)C=NC2=CC=C1C(N=1)=CN2C=CN=C2C=1NC1=CC=C(C(C)(C)O)C=C1 VKKBMXFKDVGDIT-UHFFFAOYSA-N 0.000 description 1
- BKKCNCSMGHFWLI-UHFFFAOYSA-N 2-[4-[[6-(3h-benzimidazol-5-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]-2-methylpropan-1-ol Chemical compound C1=CC(C(C)(CO)C)=CC=C1NC1=NC(C=2C=C3NC=NC3=CC=2)=CN2C1=NC=C2 BKKCNCSMGHFWLI-UHFFFAOYSA-N 0.000 description 1
- UTOQIMCZEGMDFK-UHFFFAOYSA-N 2-[4-[[6-(4-fluoro-1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]-2-methylpropan-1-ol Chemical compound C1=CC(C(C)(CO)C)=CC=C1NC1=NC(C=2C=C3NN=CC3=C(F)C=2)=CN2C1=NC=C2 UTOQIMCZEGMDFK-UHFFFAOYSA-N 0.000 description 1
- OGEQXPUNFZNNHK-UHFFFAOYSA-N 2-[4-[[6-(4-methyl-2,3-dihydro-1,4-benzoxazin-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]propan-2-ol Chemical compound C1=C2N(C)CCOC2=CC=C1C(N=1)=CN2C=CN=C2C=1NC1=CC=C(C(C)(C)O)C=C1 OGEQXPUNFZNNHK-UHFFFAOYSA-N 0.000 description 1
- DSILTPNCZPQEFC-UHFFFAOYSA-N 2-[4-[[6-(4-methyl-2,3-dihydro-1,4-benzoxazin-7-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]propan-2-ol Chemical compound C=1C=C2N(C)CCOC2=CC=1C(N=1)=CN2C=CN=C2C=1NC1=CC=C(C(C)(C)O)C=C1 DSILTPNCZPQEFC-UHFFFAOYSA-N 0.000 description 1
- NTXOWAXCGUIKIR-UHFFFAOYSA-N 2-[6-[5-methyl-8-(4-morpholin-4-ylanilino)imidazo[1,2-a]pyrazin-6-yl]-2h-indazol-3-yl]ethanol Chemical compound C12=NC=CN2C(C)=C(C=2C=C3NN=C(CCO)C3=CC=2)N=C1NC(C=C1)=CC=C1N1CCOCC1 NTXOWAXCGUIKIR-UHFFFAOYSA-N 0.000 description 1
- MJGKSGKJUOBKOV-UHFFFAOYSA-N 2-[6-[8-(3-methoxy-4-morpholin-4-ylanilino)imidazo[1,2-a]pyrazin-6-yl]-1h-indol-3-yl]ethanol Chemical compound COC1=CC(NC=2C3=NC=CN3C=C(N=2)C=2C=C3NC=C(CCO)C3=CC=2)=CC=C1N1CCOCC1 MJGKSGKJUOBKOV-UHFFFAOYSA-N 0.000 description 1
- KGKIJIOHFSFQCD-UHFFFAOYSA-N 2-[6-[8-(3-methoxy-4-morpholin-4-ylanilino)imidazo[1,2-a]pyrazin-6-yl]-2h-indazol-3-yl]ethanol Chemical compound COC1=CC(NC=2C3=NC=CN3C=C(N=2)C=2C=C3NN=C(CCO)C3=CC=2)=CC=C1N1CCOCC1 KGKIJIOHFSFQCD-UHFFFAOYSA-N 0.000 description 1
- LFCQUJKNBNXYIS-UHFFFAOYSA-N 2-[6-[8-(4-morpholin-4-ylanilino)imidazo[1,2-a]pyrazin-6-yl]-1h-indol-3-yl]ethanol Chemical compound C=1C=C2C(CCO)=CNC2=CC=1C(N=1)=CN2C=CN=C2C=1NC(C=C1)=CC=C1N1CCOCC1 LFCQUJKNBNXYIS-UHFFFAOYSA-N 0.000 description 1
- HXCXVRLOGOLLIW-UHFFFAOYSA-N 2-[6-[8-(4-morpholin-4-ylanilino)imidazo[1,2-a]pyrazin-6-yl]-2,3-dihydro-1,4-benzoxazin-4-yl]ethanol Chemical compound C1=C2N(CCO)CCOC2=CC=C1C(N=1)=CN2C=CN=C2C=1NC(C=C1)=CC=C1N1CCOCC1 HXCXVRLOGOLLIW-UHFFFAOYSA-N 0.000 description 1
- PHQQNKPDYODSIX-UHFFFAOYSA-N 2-[6-[8-(4-morpholin-4-ylanilino)imidazo[1,2-a]pyrazin-6-yl]-2h-indazol-3-yl]propan-2-ol Chemical compound C=1C=C2C(C(C)(O)C)=NNC2=CC=1C(N=1)=CN2C=CN=C2C=1NC(C=C1)=CC=C1N1CCOCC1 PHQQNKPDYODSIX-UHFFFAOYSA-N 0.000 description 1
- KLLLSNIHZOUPIF-UHFFFAOYSA-N 2-[6-[8-(4-morpholin-4-ylanilino)imidazo[1,2-a]pyrazin-6-yl]indazol-1-yl]ethanol Chemical compound C1=C2N(CCO)N=CC2=CC=C1C(N=1)=CN2C=CN=C2C=1NC(C=C1)=CC=C1N1CCOCC1 KLLLSNIHZOUPIF-UHFFFAOYSA-N 0.000 description 1
- GPHBVGCYOMHHRB-UHFFFAOYSA-N 2-[6-[8-(4-morpholin-4-ylanilino)imidazo[1,2-a]pyrazin-6-yl]indazol-2-yl]ethanol Chemical compound C=1C2=NN(CCO)C=C2C=CC=1C(N=1)=CN2C=CN=C2C=1NC(C=C1)=CC=C1N1CCOCC1 GPHBVGCYOMHHRB-UHFFFAOYSA-N 0.000 description 1
- SJUSCLJOLPZYAT-UHFFFAOYSA-N 2-[[5-[8-(4-morpholin-4-ylanilino)imidazo[1,2-a]pyrazin-6-yl]pyridin-3-yl]amino]ethanol Chemical compound OCCNC1=CN=CC(C=2N=C(NC=3C=CC(=CC=3)N3CCOCC3)C3=NC=CN3C=2)=C1 SJUSCLJOLPZYAT-UHFFFAOYSA-N 0.000 description 1
- FJMSIYXQWGOZNF-UHFFFAOYSA-N 2-[n-ethyl-4-[[6-(1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]anilino]ethanol Chemical compound C1=CC(N(CCO)CC)=CC=C1NC1=NC(C=2C=C3NN=CC3=CC=2)=CN2C1=NC=C2 FJMSIYXQWGOZNF-UHFFFAOYSA-N 0.000 description 1
- SSGWJJSJYRPJBA-UHFFFAOYSA-N 2-[n-ethyl-4-[[6-(4-fluoro-1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]anilino]ethanol Chemical compound C1=CC(N(CCO)CC)=CC=C1NC1=NC(C=2C=C3NN=CC3=C(F)C=2)=CN2C1=NC=C2 SSGWJJSJYRPJBA-UHFFFAOYSA-N 0.000 description 1
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 1
- LILXDMFJXYAKMK-UHFFFAOYSA-N 2-bromo-1,1-diethoxyethane Chemical compound CCOC(CBr)OCC LILXDMFJXYAKMK-UHFFFAOYSA-N 0.000 description 1
- IVHKZCSZELZKSJ-UHFFFAOYSA-N 2-hydroxyethyl sulfonate Chemical compound OCCOS(=O)=O IVHKZCSZELZKSJ-UHFFFAOYSA-N 0.000 description 1
- QALYSWHERHZVFA-UHFFFAOYSA-N 2-methyl-1-[4-[[6-(1h-pyrrolo[3,2-b]pyridin-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]propan-2-ol Chemical compound C1=CC(CC(C)(O)C)=CC=C1NC1=NC(C=2C=C3NC=CC3=NC=2)=CN2C1=NC=C2 QALYSWHERHZVFA-UHFFFAOYSA-N 0.000 description 1
- OWRGVQDEHAHMIX-UHFFFAOYSA-N 2-methyl-1-[4-[[6-(3-methylbenzimidazol-5-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenoxy]propan-2-ol Chemical compound C1=C2N(C)C=NC2=CC=C1C(N=1)=CN2C=CN=C2C=1NC1=CC=C(OCC(C)(C)O)C=C1 OWRGVQDEHAHMIX-UHFFFAOYSA-N 0.000 description 1
- FODRZNTUTZJQEW-UHFFFAOYSA-N 2-methyl-2-[4-[[6-(1-methylbenzimidazol-5-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]propan-1-ol Chemical compound C=1C=C2N(C)C=NC2=CC=1C(N=1)=CN2C=CN=C2C=1NC1=CC=C(C(C)(C)CO)C=C1 FODRZNTUTZJQEW-UHFFFAOYSA-N 0.000 description 1
- ZENQFWDUAPXOBK-UHFFFAOYSA-N 2-methyl-2-[4-[[6-(1-methylindazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]propan-1-ol Chemical compound C1=C2N(C)N=CC2=CC=C1C(N=1)=CN2C=CN=C2C=1NC1=CC=C(C(C)(C)CO)C=C1 ZENQFWDUAPXOBK-UHFFFAOYSA-N 0.000 description 1
- WYMFVWNRSOORJO-UHFFFAOYSA-N 2-methyl-2-[4-[[6-(1h-pyrrolo[3,2-b]pyridin-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]propan-1-ol Chemical compound C1=CC(C(C)(CO)C)=CC=C1NC1=NC(C=2C=C3NC=CC3=NC=2)=CN2C1=NC=C2 WYMFVWNRSOORJO-UHFFFAOYSA-N 0.000 description 1
- MRBYVPXFWKLPQZ-UHFFFAOYSA-N 2-methyl-2-[4-[[6-(3-methylbenzimidazol-5-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]propan-1-ol Chemical compound C1=C2N(C)C=NC2=CC=C1C(N=1)=CN2C=CN=C2C=1NC1=CC=C(C(C)(C)CO)C=C1 MRBYVPXFWKLPQZ-UHFFFAOYSA-N 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- YHWMFDLNZGIJSD-UHFFFAOYSA-N 2h-1,4-oxazine Chemical compound C1OC=CN=C1 YHWMFDLNZGIJSD-UHFFFAOYSA-N 0.000 description 1
- DTLBKXRFWUERQN-UHFFFAOYSA-N 3,5-dibromopyrazin-2-amine Chemical compound NC1=NC=C(Br)N=C1Br DTLBKXRFWUERQN-UHFFFAOYSA-N 0.000 description 1
- QXCXVUOOEBGKGR-UHFFFAOYSA-N 3-[2-ethoxy-4-[[6-(1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenoxy]-2,2-dimethylpropan-1-ol Chemical compound C1=C(OCC(C)(C)CO)C(OCC)=CC(NC=2C3=NC=CN3C=C(N=2)C=2C=C3NN=CC3=CC=2)=C1 QXCXVUOOEBGKGR-UHFFFAOYSA-N 0.000 description 1
- ZPCWEQPEPBEWGW-UHFFFAOYSA-N 3-[4-[[6-(1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]-2-methoxyphenoxy]-2,2-dimethylpropan-1-ol Chemical compound C1=C(OCC(C)(C)CO)C(OC)=CC(NC=2C3=NC=CN3C=C(N=2)C=2C=C3NN=CC3=CC=2)=C1 ZPCWEQPEPBEWGW-UHFFFAOYSA-N 0.000 description 1
- JLVZHLGJDMRWEX-UHFFFAOYSA-N 3-[4-[[6-(1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]-2-methoxyphenoxy]propan-1-ol Chemical compound C1=C(OCCCO)C(OC)=CC(NC=2C3=NC=CN3C=C(N=2)C=2C=C3NN=CC3=CC=2)=C1 JLVZHLGJDMRWEX-UHFFFAOYSA-N 0.000 description 1
- PGILGFGFGNDYLT-UHFFFAOYSA-N 3-[4-[[6-(1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenoxy]-2,2-dimethylpropan-1-ol Chemical compound C1=CC(OCC(C)(CO)C)=CC=C1NC1=NC(C=2C=C3NN=CC3=CC=2)=CN2C1=NC=C2 PGILGFGFGNDYLT-UHFFFAOYSA-N 0.000 description 1
- CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- WQOZCZLVJDVCRT-UHFFFAOYSA-N 3-ethyl-1-[4-[[6-(1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]azetidin-3-ol Chemical compound C1C(CC)(O)CN1C(C=C1)=CC=C1NC1=NC(C=2C=C3NN=CC3=CC=2)=CN2C1=NC=C2 WQOZCZLVJDVCRT-UHFFFAOYSA-N 0.000 description 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 1
- BBCFEHIUDRXJMQ-UHFFFAOYSA-N 3-methyl-1-[4-[[6-(1-methylindazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]azetidin-3-ol Chemical compound C1=C2N(C)N=CC2=CC=C1C(N=1)=CN2C=CN=C2C=1NC(C=C1)=CC=C1N1CC(C)(O)C1 BBCFEHIUDRXJMQ-UHFFFAOYSA-N 0.000 description 1
- KMKUDEUYFFZSMU-UHFFFAOYSA-N 3-methyl-1-[4-[[6-(1h-pyrrolo[3,2-b]pyridin-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]azetidin-3-ol Chemical compound C1C(C)(O)CN1C(C=C1)=CC=C1NC1=NC(C=2C=C3NC=CC3=NC=2)=CN2C1=NC=C2 KMKUDEUYFFZSMU-UHFFFAOYSA-N 0.000 description 1
- LDLAEUFQUOXALI-UHFFFAOYSA-N 3-methylazetidin-3-ol Chemical compound CC1(O)CNC1 LDLAEUFQUOXALI-UHFFFAOYSA-N 0.000 description 1
- 125000005917 3-methylpentyl group Chemical group 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- WEDKTMOIKOKBSH-UHFFFAOYSA-N 4,5-dihydrothiadiazole Chemical compound C1CN=NS1 WEDKTMOIKOKBSH-UHFFFAOYSA-N 0.000 description 1
- YGFIHABVIBLLMV-UHFFFAOYSA-N 4-[4-[[6-(1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenoxy]cyclohexan-1-ol Chemical compound C1CC(O)CCC1OC(C=C1)=CC=C1NC1=NC(C=2C=C3NN=CC3=CC=2)=CN2C1=NC=C2 YGFIHABVIBLLMV-UHFFFAOYSA-N 0.000 description 1
- RCXGPWKWIZHSMJ-UHFFFAOYSA-N 4-[8-(3,4-dimethoxyanilino)imidazo[1,2-a]pyrazin-6-yl]benzonitrile Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC(C=2C=CC(=CC=2)C#N)=CN2C1=NC=C2 RCXGPWKWIZHSMJ-UHFFFAOYSA-N 0.000 description 1
- BAWFBURWLTWOJG-UHFFFAOYSA-N 4-[[6-(1H-indazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenol Chemical compound C1=CC(O)=CC=C1NC1=NC(C=2C=C3NN=CC3=CC=2)=CN2C1=NC=C2 BAWFBURWLTWOJG-UHFFFAOYSA-N 0.000 description 1
- SWZMBOLYTLXYDC-UHFFFAOYSA-N 4-[[6-(1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC1=NC(C=2C=C3NN=CC3=CC=2)=CN2C1=NC=C2 SWZMBOLYTLXYDC-UHFFFAOYSA-N 0.000 description 1
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- BGRQAMHIZILGNC-UHFFFAOYSA-N 4-methyl-1-[4-[[6-(1-methylbenzimidazol-5-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]piperidin-4-ol Chemical compound C=1C=C2N(C)C=NC2=CC=1C(N=1)=CN2C=CN=C2C=1NC(C=C1)=CC=C1N1CCC(C)(O)CC1 BGRQAMHIZILGNC-UHFFFAOYSA-N 0.000 description 1
- FUYKMUOQNGZSLK-UHFFFAOYSA-N 4-methyl-1-[4-[[6-(1h-pyrrolo[3,2-b]pyridin-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]piperidin-4-ol Chemical compound C1CC(C)(O)CCN1C(C=C1)=CC=C1NC1=NC(C=2C=C3NC=CC3=NC=2)=CN2C1=NC=C2 FUYKMUOQNGZSLK-UHFFFAOYSA-N 0.000 description 1
- XLJKIZVPYGGDLG-UHFFFAOYSA-N 4-methyl-1-[4-[[6-(3-methylbenzimidazol-5-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]piperidin-4-ol Chemical compound C1=C2N(C)C=NC2=CC=C1C(N=1)=CN2C=CN=C2C=1NC(C=C1)=CC=C1N1CCC(C)(O)CC1 XLJKIZVPYGGDLG-UHFFFAOYSA-N 0.000 description 1
- QRAOZQGIUIDZQZ-UHFFFAOYSA-N 4-methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1,4-benzoxazine Chemical compound C=1C=C2N(C)CCOC2=CC=1B1OC(C)(C)C(C)(C)O1 QRAOZQGIUIDZQZ-UHFFFAOYSA-N 0.000 description 1
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- QRCGFTXRXYMJOS-UHFFFAOYSA-N 4h-1,4-benzoxazin-3-one Chemical compound C1=CC=C2NC(=O)COC2=C1 QRCGFTXRXYMJOS-UHFFFAOYSA-N 0.000 description 1
- XISPDFMAOWZEQG-UHFFFAOYSA-N 4h-1,4-oxazin-3-one Chemical compound O=C1COC=CN1 XISPDFMAOWZEQG-UHFFFAOYSA-N 0.000 description 1
- PTOFYXIDOXXXHA-UHFFFAOYSA-N 5-[5-methyl-8-(4-morpholin-4-ylanilino)imidazo[1,2-a]pyrazin-6-yl]-1,3-dihydrobenzimidazol-2-one Chemical compound C12=NC=CN2C(C)=C(C=2C=C3NC(=O)NC3=CC=2)N=C1NC(C=C1)=CC=C1N1CCOCC1 PTOFYXIDOXXXHA-UHFFFAOYSA-N 0.000 description 1
- CNVLFLSTZICVFA-UHFFFAOYSA-N 5-[8-(3,4-dimethoxyanilino)imidazo[1,2-a]pyrazin-6-yl]-1h-pyridin-2-one Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC(C2=CNC(=O)C=C2)=CN2C1=NC=C2 CNVLFLSTZICVFA-UHFFFAOYSA-N 0.000 description 1
- KTCDICSIMNIWLF-UHFFFAOYSA-N 5-[8-(3-methoxy-4-morpholin-4-ylanilino)-5-methylimidazo[1,2-a]pyrazin-6-yl]-1,3-dihydrobenzimidazol-2-one Chemical compound COC1=CC(NC=2C3=NC=CN3C(C)=C(N=2)C=2C=C3NC(=O)NC3=CC=2)=CC=C1N1CCOCC1 KTCDICSIMNIWLF-UHFFFAOYSA-N 0.000 description 1
- UUPLNKYLXMQKHH-UHFFFAOYSA-N 5-[8-(4-morpholin-4-ylanilino)imidazo[1,2-a]pyrazin-6-yl]-1,3-dihydroindol-2-one Chemical compound C=1C=C2NC(=O)CC2=CC=1C(N=1)=CN2C=CN=C2C=1NC(C=C1)=CC=C1N1CCOCC1 UUPLNKYLXMQKHH-UHFFFAOYSA-N 0.000 description 1
- ZPBZTCRWDYRVIZ-UHFFFAOYSA-N 5-[8-(4-morpholin-4-ylanilino)imidazo[1,2-a]pyrazin-6-yl]-3h-1,3-benzoxazol-2-one Chemical compound C=1C=C2OC(=O)NC2=CC=1C(N=1)=CN2C=CN=C2C=1NC(C=C1)=CC=C1N1CCOCC1 ZPBZTCRWDYRVIZ-UHFFFAOYSA-N 0.000 description 1
- GMFWMUQPOBOFEL-UHFFFAOYSA-N 5-[[6-(1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]-1,3-dihydroindol-2-one Chemical compound C1=C2C=NNC2=CC(C=2N=C(C3=NC=CN3C=2)NC=2C=C3CC(NC3=CC=2)=O)=C1 GMFWMUQPOBOFEL-UHFFFAOYSA-N 0.000 description 1
- NWGDGQGEZLKZON-UHFFFAOYSA-N 5-[[6-(1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]-2-morpholin-4-ylbenzonitrile Chemical compound N#CC1=CC(NC=2C3=NC=CN3C=C(N=2)C=2C=C3NN=CC3=CC=2)=CC=C1N1CCOCC1 NWGDGQGEZLKZON-UHFFFAOYSA-N 0.000 description 1
- RXGHGGCOYJRRBR-UHFFFAOYSA-N 6-(2-amino-3h-benzimidazol-5-yl)-n-(3,4-dimethoxyphenyl)imidazo[1,2-a]pyrazin-8-amine Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC(C=2C=C3NC(N)=NC3=CC=2)=CN2C1=NC=C2 RXGHGGCOYJRRBR-UHFFFAOYSA-N 0.000 description 1
- YDRIEFOGTNWGAB-UHFFFAOYSA-N 6-(3-amino-1h-indazol-5-yl)-n-(3-methoxy-4-morpholin-4-ylphenyl)imidazo[1,2-a]pyrazin-8-amine Chemical compound COC1=CC(NC=2C3=NC=CN3C=C(N=2)C=2C=C3C(N)=NNC3=CC=2)=CC=C1N1CCOCC1 YDRIEFOGTNWGAB-UHFFFAOYSA-N 0.000 description 1
- LWPGBSRBPGKKJI-UHFFFAOYSA-N 6-(3-amino-1h-indazol-5-yl)-n-(3-methoxy-4-pyrrolidin-1-ylphenyl)imidazo[1,2-a]pyrazin-8-amine Chemical compound COC1=CC(NC=2C3=NC=CN3C=C(N=2)C=2C=C3C(N)=NNC3=CC=2)=CC=C1N1CCCC1 LWPGBSRBPGKKJI-UHFFFAOYSA-N 0.000 description 1
- XZGVMIMCAPSDIF-UHFFFAOYSA-N 6-(3-amino-1h-indazol-5-yl)-n-(4-ethoxy-3-methoxyphenyl)imidazo[1,2-a]pyrazin-8-amine Chemical compound C1=C(OC)C(OCC)=CC=C1NC1=NC(C=2C=C3C(N)=NNC3=CC=2)=CN2C1=NC=C2 XZGVMIMCAPSDIF-UHFFFAOYSA-N 0.000 description 1
- QTSCGXDXCGKQNK-UHFFFAOYSA-N 6-(3-amino-1h-indazol-6-yl)-n-(3-methoxy-4-morpholin-4-ylphenyl)imidazo[1,2-a]pyrazin-8-amine Chemical compound COC1=CC(NC=2C3=NC=CN3C=C(N=2)C=2C=C3NN=C(N)C3=CC=2)=CC=C1N1CCOCC1 QTSCGXDXCGKQNK-UHFFFAOYSA-N 0.000 description 1
- MWDZYVMBSNETRN-UHFFFAOYSA-N 6-(3-amino-1h-indazol-6-yl)-n-(4-ethoxy-3-methoxyphenyl)imidazo[1,2-a]pyrazin-8-amine Chemical compound C1=C(OC)C(OCC)=CC=C1NC1=NC(C=2C=C3NN=C(N)C3=CC=2)=CN2C1=NC=C2 MWDZYVMBSNETRN-UHFFFAOYSA-N 0.000 description 1
- BDJSCPVKVBKFND-UHFFFAOYSA-N 6-(3-amino-1h-indazol-6-yl)-n-(4-morpholin-4-ylphenyl)imidazo[1,2-a]pyrazin-8-amine Chemical compound C=1C=C2C(N)=NNC2=CC=1C(N=1)=CN2C=CN=C2C=1NC(C=C1)=CC=C1N1CCOCC1 BDJSCPVKVBKFND-UHFFFAOYSA-N 0.000 description 1
- FAIAXYWXOOBWCK-UHFFFAOYSA-N 6-(5-amino-6-methylpyridin-3-yl)-N-(4-morpholin-4-ylphenyl)imidazo[1,2-a]pyrazin-8-amine Chemical compound NC=1C=C(C=NC=1C)C=1N=C(C=2N(C=1)C=CN=2)NC1=CC=C(C=C1)N1CCOCC1 FAIAXYWXOOBWCK-UHFFFAOYSA-N 0.000 description 1
- WCLQGWQXRCNKHS-UHFFFAOYSA-N 6-(5-aminopyridin-3-yl)-n-(4-morpholin-4-ylphenyl)imidazo[1,2-a]pyrazin-8-amine Chemical compound NC1=CN=CC(C=2N=C(NC=3C=CC(=CC=3)N3CCOCC3)C3=NC=CN3C=2)=C1 WCLQGWQXRCNKHS-UHFFFAOYSA-N 0.000 description 1
- UUGFFVXOVKEYMH-UHFFFAOYSA-N 6-(6-aminopyridin-3-yl)-n-(3,4-dimethoxyphenyl)imidazo[1,2-a]pyrazin-8-amine Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC(C=2C=NC(N)=CC=2)=CN2C1=NC=C2 UUGFFVXOVKEYMH-UHFFFAOYSA-N 0.000 description 1
- FZDBMEPIQZVSOX-UHFFFAOYSA-N 6-[5-ethyl-8-(4-morpholin-4-ylanilino)imidazo[1,2-a]pyrazin-6-yl]-1,3-dihydroindol-2-one Chemical compound C12=NC=CN2C(CC)=C(C=2C=C3NC(=O)CC3=CC=2)N=C1NC(C=C1)=CC=C1N1CCOCC1 FZDBMEPIQZVSOX-UHFFFAOYSA-N 0.000 description 1
- YYPYCBLTGCMPRN-UHFFFAOYSA-N 6-[8-(3,4-dimethoxyanilino)imidazo[1,2-a]pyrazin-6-yl]-2-methyl-4h-1,4-benzoxazin-3-one Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC(C=2C=C3NC(=O)C(C)OC3=CC=2)=CN2C1=NC=C2 YYPYCBLTGCMPRN-UHFFFAOYSA-N 0.000 description 1
- BIMAPMTWJAFCKD-UHFFFAOYSA-N 6-[8-(3,4-dimethoxyanilino)imidazo[1,2-a]pyrazin-6-yl]-4-methyl-1,4-benzoxazin-3-one Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC(C=2C=C3N(C)C(=O)COC3=CC=2)=CN2C1=NC=C2 BIMAPMTWJAFCKD-UHFFFAOYSA-N 0.000 description 1
- TWVGBHPFQROYGO-UHFFFAOYSA-N 6-[8-(3,4-dimethoxyanilino)imidazo[1,2-a]pyrazin-6-yl]-4h-1,4-benzoxazin-3-one Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC(C=2C=C3NC(=O)COC3=CC=2)=CN2C1=NC=C2 TWVGBHPFQROYGO-UHFFFAOYSA-N 0.000 description 1
- FFOXIISPTNDSHW-UHFFFAOYSA-N 6-[8-(3,4-dimethoxyanilino)imidazo[1,2-a]pyrazin-6-yl]quinolin-2-amine Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC(C=2C=C3C=CC(N)=NC3=CC=2)=CN2C1=NC=C2 FFOXIISPTNDSHW-UHFFFAOYSA-N 0.000 description 1
- APYZYZCTNYLENV-UHFFFAOYSA-N 6-[8-(3,4-dimethoxyanilino)imidazo[1,2-a]pyrazin-6-yl]quinolin-3-amine Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC(C=2C=C3C=C(N)C=NC3=CC=2)=CN2C1=NC=C2 APYZYZCTNYLENV-UHFFFAOYSA-N 0.000 description 1
- NOFSYTUQEHOLOA-UHFFFAOYSA-N 6-[8-(3-ethoxy-4-morpholin-4-ylanilino)imidazo[1,2-a]pyrazin-6-yl]-3,3-dimethyl-1h-indol-2-one Chemical compound CCOC1=CC(NC=2C3=NC=CN3C=C(N=2)C=2C=C3C(C(C(=O)N3)(C)C)=CC=2)=CC=C1N1CCOCC1 NOFSYTUQEHOLOA-UHFFFAOYSA-N 0.000 description 1
- MNANBUWXDRNBRT-UHFFFAOYSA-N 6-[8-(3-ethoxy-4-morpholin-4-ylanilino)imidazo[1,2-a]pyrazin-6-yl]-4h-1,4-benzoxazin-3-one Chemical compound CCOC1=CC(NC=2C3=NC=CN3C=C(N=2)C=2C=C3NC(=O)COC3=CC=2)=CC=C1N1CCOCC1 MNANBUWXDRNBRT-UHFFFAOYSA-N 0.000 description 1
- NGYXIJRCWFAGOJ-UHFFFAOYSA-N 6-[8-(3-methoxy-4-morpholin-4-ylanilino)imidazo[1,2-a]pyrazin-6-yl]-3,3-dimethyl-1h-indol-2-one Chemical compound COC1=CC(NC=2C3=NC=CN3C=C(N=2)C=2C=C3C(C(C(=O)N3)(C)C)=CC=2)=CC=C1N1CCOCC1 NGYXIJRCWFAGOJ-UHFFFAOYSA-N 0.000 description 1
- LUSKJPFSGVAEKB-UHFFFAOYSA-N 6-[8-(3-methoxy-4-morpholin-4-ylanilino)imidazo[1,2-a]pyrazin-6-yl]-4h-1,4-benzoxazin-3-one Chemical compound COC1=CC(NC=2C3=NC=CN3C=C(N=2)C=2C=C3NC(=O)COC3=CC=2)=CC=C1N1CCOCC1 LUSKJPFSGVAEKB-UHFFFAOYSA-N 0.000 description 1
- RXFQNWUJRPSHFU-UHFFFAOYSA-N 6-[8-(3-methoxy-4-morpholin-4-ylanilino)imidazo[1,2-a]pyrazin-6-yl]quinazolin-2-amine Chemical compound COC1=CC(NC=2C3=NC=CN3C=C(N=2)C=2C=C3C=NC(N)=NC3=CC=2)=CC=C1N1CCOCC1 RXFQNWUJRPSHFU-UHFFFAOYSA-N 0.000 description 1
- WVCWYFHCRUABIV-UHFFFAOYSA-N 6-[8-(4-ethoxy-3-methoxyanilino)imidazo[1,2-a]pyrazin-6-yl]-1,3-dihydroindol-2-one Chemical compound C1=C(OC)C(OCC)=CC=C1NC1=NC(C=2C=C3NC(=O)CC3=CC=2)=CN2C1=NC=C2 WVCWYFHCRUABIV-UHFFFAOYSA-N 0.000 description 1
- WDWPJMALDHISIB-UHFFFAOYSA-N 6-[8-(4-ethoxy-3-methoxyanilino)imidazo[1,2-a]pyrazin-6-yl]-1h-indazole-3-carboxamide Chemical compound C1=C(OC)C(OCC)=CC=C1NC1=NC(C=2C=C3NN=C(C3=CC=2)C(N)=O)=CN2C1=NC=C2 WDWPJMALDHISIB-UHFFFAOYSA-N 0.000 description 1
- QDTSKPIVSLXSIH-UHFFFAOYSA-N 6-[8-(4-morpholin-4-ylanilino)imidazo[1,2-a]pyrazin-6-yl]-1,3-dihydroindol-2-one Chemical compound C1=C2NC(=O)CC2=CC=C1C(N=1)=CN2C=CN=C2C=1NC(C=C1)=CC=C1N1CCOCC1 QDTSKPIVSLXSIH-UHFFFAOYSA-N 0.000 description 1
- HXZHTMZMONHYDA-UHFFFAOYSA-N 6-[8-(4-morpholin-4-ylanilino)imidazo[1,2-a]pyrazin-6-yl]-4h-1,4-benzoxazin-3-one Chemical compound C1=C2NC(=O)COC2=CC=C1C(N=1)=CN2C=CN=C2C=1NC(C=C1)=CC=C1N1CCOCC1 HXZHTMZMONHYDA-UHFFFAOYSA-N 0.000 description 1
- JNAURSNHLVKRLB-UHFFFAOYSA-N 6-[8-(4-morpholin-4-ylanilino)imidazo[1,2-a]pyrazin-6-yl]quinazolin-2-amine Chemical compound C1=CC2=NC(N)=NC=C2C=C1C(N=1)=CN2C=CN=C2C=1NC(C=C1)=CC=C1N1CCOCC1 JNAURSNHLVKRLB-UHFFFAOYSA-N 0.000 description 1
- OOOYPNKLLNQKOC-UHFFFAOYSA-N 6-[8-[3-(2-hydroxyethoxy)-4-morpholin-4-ylanilino]imidazo[1,2-a]pyrazin-6-yl]-3-methyl-1h-benzimidazol-2-one Chemical compound C1=C2NC(=O)N(C)C2=CC=C1C(N=1)=CN2C=CN=C2C=1NC(C=C1OCCO)=CC=C1N1CCOCC1 OOOYPNKLLNQKOC-UHFFFAOYSA-N 0.000 description 1
- IUTHUUSQFWLIEO-UHFFFAOYSA-N 6-[8-[4-(1-hydroxy-2-methylpropan-2-yl)anilino]imidazo[1,2-a]pyrazin-6-yl]-4h-1,4-benzoxazin-3-one Chemical compound C1=CC(C(C)(CO)C)=CC=C1NC1=NC(C=2C=C3NC(=O)COC3=CC=2)=CN2C1=NC=C2 IUTHUUSQFWLIEO-UHFFFAOYSA-N 0.000 description 1
- QFIIDCDXHVDGAY-UHFFFAOYSA-N 6-[8-[4-(2-hydroxypropan-2-yl)anilino]imidazo[1,2-a]pyrazin-6-yl]-1,3-dihydroindol-2-one Chemical compound C1=CC(C(C)(O)C)=CC=C1NC1=NC(C=2C=C3NC(=O)CC3=CC=2)=CN2C1=NC=C2 QFIIDCDXHVDGAY-UHFFFAOYSA-N 0.000 description 1
- QLWMBSKYTATXPI-UHFFFAOYSA-N 6-[8-[4-(3-hydroxy-3-methylazetidin-1-yl)anilino]imidazo[1,2-a]pyrazin-6-yl]-3,3-dimethyl-1h-indol-2-one Chemical compound C1C(C)(O)CN1C(C=C1)=CC=C1NC1=NC(C=2C=C3C(C(C(=O)N3)(C)C)=CC=2)=CN2C1=NC=C2 QLWMBSKYTATXPI-UHFFFAOYSA-N 0.000 description 1
- JMPKJINSWXGTCG-UHFFFAOYSA-N 6-[8-[4-(3-hydroxy-3-methylazetidin-1-yl)anilino]imidazo[1,2-a]pyrazin-6-yl]-3-methyl-1h-benzimidazol-2-one Chemical compound C1=C2NC(=O)N(C)C2=CC=C1C(N=1)=CN2C=CN=C2C=1NC(C=C1)=CC=C1N1CC(C)(O)C1 JMPKJINSWXGTCG-UHFFFAOYSA-N 0.000 description 1
- LFRHKPGMDUBMMJ-UHFFFAOYSA-N 6-[8-[4-(3-hydroxy-3-methylazetidin-1-yl)anilino]imidazo[1,2-a]pyrazin-6-yl]-4h-1,4-benzoxazin-3-one Chemical compound C1C(C)(O)CN1C(C=C1)=CC=C1NC1=NC(C=2C=C3NC(=O)COC3=CC=2)=CN2C1=NC=C2 LFRHKPGMDUBMMJ-UHFFFAOYSA-N 0.000 description 1
- JRELYSSAEQQVBX-UHFFFAOYSA-N 6-[8-[4-(3-hydroxy-3-methylpyrrolidin-1-yl)anilino]imidazo[1,2-a]pyrazin-6-yl]-4h-1,4-benzoxazin-3-one Chemical compound C1C(C)(O)CCN1C(C=C1)=CC=C1NC1=NC(C=2C=C3NC(=O)COC3=CC=2)=CN2C1=NC=C2 JRELYSSAEQQVBX-UHFFFAOYSA-N 0.000 description 1
- FESDNEDXXSVZEV-UHFFFAOYSA-N 6-[8-[4-(4-hydroxy-4-methylpiperidin-1-yl)anilino]imidazo[1,2-a]pyrazin-6-yl]-3,3-dimethyl-1h-indol-2-one Chemical compound C=1C=C2C(C)(C)C(=O)NC2=CC=1C(N=1)=CN2C=CN=C2C=1NC(C=C1)=CC=C1N1CCC(C)(O)CC1 FESDNEDXXSVZEV-UHFFFAOYSA-N 0.000 description 1
- YXRMKIGKLUDHKO-UHFFFAOYSA-N 6-[8-[4-(4-hydroxy-4-methylpiperidin-1-yl)anilino]imidazo[1,2-a]pyrazin-6-yl]-4h-1,4-benzoxazin-3-one Chemical compound C1CC(C)(O)CCN1C(C=C1)=CC=C1NC1=NC(C=2C=C3NC(=O)COC3=CC=2)=CN2C1=NC=C2 YXRMKIGKLUDHKO-UHFFFAOYSA-N 0.000 description 1
- CAVIARWDKUGNOU-UHFFFAOYSA-N 6-[[6-(1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]-1,3-dihydroindol-2-one Chemical compound C1=C2C=NNC2=CC(C=2N=C(C3=NC=CN3C=2)NC2=CC=C3CC(NC3=C2)=O)=C1 CAVIARWDKUGNOU-UHFFFAOYSA-N 0.000 description 1
- STQGQHZAVUOBTE-UHFFFAOYSA-N 7-Cyan-hept-2t-en-4,6-diinsaeure Natural products C1=2C(O)=C3C(=O)C=4C(OC)=CC=CC=4C(=O)C3=C(O)C=2CC(O)(C(C)=O)CC1OC1CC(N)C(O)C(C)O1 STQGQHZAVUOBTE-UHFFFAOYSA-N 0.000 description 1
- QWZJFRFVSFHLGY-UHFFFAOYSA-N 7-[8-(3,4-dimethoxyanilino)imidazo[1,2-a]pyrazin-6-yl]-1h-quinoxalin-2-one Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC(C=2C=C3N=C(O)C=NC3=CC=2)=CN2C1=NC=C2 QWZJFRFVSFHLGY-UHFFFAOYSA-N 0.000 description 1
- IVGJQHCNAWVBPA-UHFFFAOYSA-N 7-[8-(3,4-dimethoxyanilino)imidazo[1,2-a]pyrazin-6-yl]-4h-1,4-benzoxazin-3-one Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC(C=2C=C3OCC(=O)NC3=CC=2)=CN2C1=NC=C2 IVGJQHCNAWVBPA-UHFFFAOYSA-N 0.000 description 1
- BSPYOYLKTSXGRS-UHFFFAOYSA-N 7-[8-(4-morpholin-4-ylanilino)imidazo[1,2-a]pyrazin-6-yl]-1h-quinolin-2-one Chemical compound C1=C2NC(=O)C=CC2=CC=C1C(N=1)=CN2C=CN=C2C=1NC(C=C1)=CC=C1N1CCOCC1 BSPYOYLKTSXGRS-UHFFFAOYSA-N 0.000 description 1
- RFQAQLQGBIGQKQ-UHFFFAOYSA-N 7-[8-(4-morpholin-4-ylanilino)imidazo[1,2-a]pyrazin-6-yl]-1h-quinoxalin-2-one Chemical compound C1=C2NC(=O)C=NC2=CC=C1C(N=1)=CN2C=CN=C2C=1NC(C=C1)=CC=C1N1CCOCC1 RFQAQLQGBIGQKQ-UHFFFAOYSA-N 0.000 description 1
- VINZHJJDABDTGZ-UHFFFAOYSA-N 7-[8-(4-morpholin-4-ylanilino)imidazo[1,2-a]pyrazin-6-yl]-3,4-dihydro-1H-quinoxalin-2-one Chemical compound C1=C2NC(=O)CNC2=CC=C1C(N=1)=CN2C=CN=C2C=1NC(C=C1)=CC=C1N1CCOCC1 VINZHJJDABDTGZ-UHFFFAOYSA-N 0.000 description 1
- DGFVNMNNLKCJQB-UHFFFAOYSA-N 7-[8-(4-morpholin-4-ylanilino)imidazo[1,2-a]pyrazin-6-yl]-3,4-dihydro-1h-quinolin-2-one Chemical compound C1=C2NC(=O)CCC2=CC=C1C(N=1)=CN2C=CN=C2C=1NC(C=C1)=CC=C1N1CCOCC1 DGFVNMNNLKCJQB-UHFFFAOYSA-N 0.000 description 1
- SBHASFNFOACLMN-UHFFFAOYSA-N 7-[8-(4-morpholin-4-ylanilino)imidazo[1,2-a]pyrazin-6-yl]-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound C=1N=C2NC(=O)COC2=CC=1C(N=1)=CN2C=CN=C2C=1NC(C=C1)=CC=C1N1CCOCC1 SBHASFNFOACLMN-UHFFFAOYSA-N 0.000 description 1
- TZXAIZIRSUPFFI-UHFFFAOYSA-N 7-[8-[(4-methyl-2,3-dihydro-1,4-benzoxazin-7-yl)amino]imidazo[1,2-a]pyrazin-6-yl]-1h-quinoxalin-2-one Chemical compound N1=CC(O)=NC2=CC(C=3N=C(C4=NC=CN4C=3)NC=3C=C4OCCN(C4=CC=3)C)=CC=C21 TZXAIZIRSUPFFI-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- XGWFJBFNAQHLEF-UHFFFAOYSA-N 9-anthroic acid Chemical compound C1=CC=C2C(C(=O)O)=C(C=CC=C3)C3=CC2=C1 XGWFJBFNAQHLEF-UHFFFAOYSA-N 0.000 description 1
- 208000026872 Addison Disease Diseases 0.000 description 1
- 229920000936 Agarose Polymers 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 108020000948 Antisense Oligonucleotides Proteins 0.000 description 1
- 206010003011 Appendicitis Diseases 0.000 description 1
- 208000012657 Atopic disease Diseases 0.000 description 1
- 230000003844 B-cell-activation Effects 0.000 description 1
- 108091007065 BIRCs Proteins 0.000 description 1
- DWRXFEITVBNRMK-UHFFFAOYSA-N Beta-D-1-Arabinofuranosylthymine Natural products O=C1NC(=O)C(C)=CN1C1C(O)C(O)C(CO)O1 DWRXFEITVBNRMK-UHFFFAOYSA-N 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 206010056695 Bronchial oedema Diseases 0.000 description 1
- 206010006487 Bronchostenosis Diseases 0.000 description 1
- 238000006418 Brown reaction Methods 0.000 description 1
- NQARUSAQGCZYNO-UHFFFAOYSA-N C1C(OC2=C(N1)C=C(C=C2)N)C3=NC(=CN4C3=NC=C4)C5=CC6=C(C=C5)C=CN6 Chemical compound C1C(OC2=C(N1)C=C(C=C2)N)C3=NC(=CN4C3=NC=C4)C5=CC6=C(C=C5)C=CN6 NQARUSAQGCZYNO-UHFFFAOYSA-N 0.000 description 1
- HYXKEUSHMJRVMC-UHFFFAOYSA-N C1C(OC2=C(N1)C=CC(=C2)N)C3=NC(=CN4C3=NC=C4)C5=CC6=C(C=C5)C=NN6 Chemical compound C1C(OC2=C(N1)C=CC(=C2)N)C3=NC(=CN4C3=NC=C4)C5=CC6=C(C=C5)C=NN6 HYXKEUSHMJRVMC-UHFFFAOYSA-N 0.000 description 1
- RJIZKRMXYOXLMB-UHFFFAOYSA-N C1CN(C2=C1C=CC(=C2)N)C3=NC(=CN4C3=NC=C4)C5=CC6=C(C=C5)C=NN6 Chemical compound C1CN(C2=C1C=CC(=C2)N)C3=NC(=CN4C3=NC=C4)C5=CC6=C(C=C5)C=NN6 RJIZKRMXYOXLMB-UHFFFAOYSA-N 0.000 description 1
- BLPVCKGKUWSORR-UHFFFAOYSA-N C1CNC(C2=C1C=C(C=C2)N)C3=NC(=CN4C3=NC=C4)C5=CC6=C(C=C5)C=NN6 Chemical compound C1CNC(C2=C1C=C(C=C2)N)C3=NC(=CN4C3=NC=C4)C5=CC6=C(C=C5)C=NN6 BLPVCKGKUWSORR-UHFFFAOYSA-N 0.000 description 1
- RRGXDWYYDHESFT-UHFFFAOYSA-N C1CNC2=C(C=CC(=C2)N)OC1C3=NC(=CN4C3=NC=C4)C5=CC6=C(C=C5)C=NN6 Chemical compound C1CNC2=C(C=CC(=C2)N)OC1C3=NC(=CN4C3=NC=C4)C5=CC6=C(C=C5)C=NN6 RRGXDWYYDHESFT-UHFFFAOYSA-N 0.000 description 1
- XQMRDNUPUZVNFC-UHFFFAOYSA-N C1CNC2=C1C=CC(=C2)C3=CN4C=CN=C4C(=N3)C5CNC6=C(O5)C=CC(=C6)N Chemical compound C1CNC2=C1C=CC(=C2)C3=CN4C=CN=C4C(=N3)C5CNC6=C(O5)C=CC(=C6)N XQMRDNUPUZVNFC-UHFFFAOYSA-N 0.000 description 1
- GLVXDGOUHVLHIT-UHFFFAOYSA-N C1CNCC2=C1C=C(C=C2)C3=CN4C=C(N=C4C(=N3)N)C5=CC=C(C=C5)N6CCOCC6 Chemical compound C1CNCC2=C1C=C(C=C2)C3=CN4C=C(N=C4C(=N3)N)C5=CC=C(C=C5)N6CCOCC6 GLVXDGOUHVLHIT-UHFFFAOYSA-N 0.000 description 1
- CKLZRGGUBIEYFB-UHFFFAOYSA-N C1CNCC2=C1C=CC(=C2)C3=CN4C=C(N=C4C(=N3)N)C5=CC=C(C=C5)N6CCOCC6 Chemical compound C1CNCC2=C1C=CC(=C2)C3=CN4C=C(N=C4C(=N3)N)C5=CC=C(C=C5)N6CCOCC6 CKLZRGGUBIEYFB-UHFFFAOYSA-N 0.000 description 1
- BGZXPILRSYQDFT-UHFFFAOYSA-N C1COC2=C(N1)C=C(C=N2)C3=CN4C=C(N=C4C(=N3)N)C5=CC=C(C=C5)N6CCOCC6 Chemical compound C1COC2=C(N1)C=C(C=N2)C3=CN4C=C(N=C4C(=N3)N)C5=CC=C(C=C5)N6CCOCC6 BGZXPILRSYQDFT-UHFFFAOYSA-N 0.000 description 1
- FYSMDSPDVIGGQA-UHFFFAOYSA-N C1COC2=C(N1)C=CC(=N2)C3=CN4C=C(N=C4C(=N3)N)C5=CC=C(C=C5)N6CCOCC6 Chemical compound C1COC2=C(N1)C=CC(=N2)C3=CN4C=C(N=C4C(=N3)N)C5=CC=C(C=C5)N6CCOCC6 FYSMDSPDVIGGQA-UHFFFAOYSA-N 0.000 description 1
- CYCWXCMEDKLPIO-UHFFFAOYSA-N C1COC2=C(N1)N=CC(=C2)C3=CN4C=C(N=C4C(=N3)N)C5=CC=C(C=C5)N6CCOCC6 Chemical compound C1COC2=C(N1)N=CC(=C2)C3=CN4C=C(N=C4C(=N3)N)C5=CC=C(C=C5)N6CCOCC6 CYCWXCMEDKLPIO-UHFFFAOYSA-N 0.000 description 1
- QXIZNZKZPKHSTN-UHFFFAOYSA-N C1COCCN1C2=CC=C(C=C2)C3=CN4C=C(N=C(C4=N3)N)C5=CC6=C(C=CN6)N=C5 Chemical compound C1COCCN1C2=CC=C(C=C2)C3=CN4C=C(N=C(C4=N3)N)C5=CC6=C(C=CN6)N=C5 QXIZNZKZPKHSTN-UHFFFAOYSA-N 0.000 description 1
- WAOWYAJSZKTWKC-UHFFFAOYSA-N C1COCCN1C2=CC=C(C=C2)C3=CN4C=C(N=C(C4=N3)N)C5=CN=CS5 Chemical compound C1COCCN1C2=CC=C(C=C2)C3=CN4C=C(N=C(C4=N3)N)C5=CN=CS5 WAOWYAJSZKTWKC-UHFFFAOYSA-N 0.000 description 1
- QXVJLSVBUMGDOR-UHFFFAOYSA-N C1COCCN1C2=CC=C(C=C2)C3=CN4C=C(N=C(C4=N3)N)C5=CNN=C5 Chemical compound C1COCCN1C2=CC=C(C=C2)C3=CN4C=C(N=C(C4=N3)N)C5=CNN=C5 QXVJLSVBUMGDOR-UHFFFAOYSA-N 0.000 description 1
- XHSUDSBGFABPSH-UHFFFAOYSA-N CC(C)(C(C=C1)=CC=C1C1=CN(C=CN=C2N)C2=N1)OC Chemical compound CC(C)(C(C=C1)=CC=C1C1=CN(C=CN=C2N)C2=N1)OC XHSUDSBGFABPSH-UHFFFAOYSA-N 0.000 description 1
- HERZQLKPBWSFMR-UHFFFAOYSA-N CC(C)(COC)C(C=C1)=CC=C1C1=CN(C=CN=C2N)C2=N1 Chemical compound CC(C)(COC)C(C=C1)=CC=C1C1=CN(C=CN=C2N)C2=N1 HERZQLKPBWSFMR-UHFFFAOYSA-N 0.000 description 1
- NMCJRBJHRVNWMB-UHFFFAOYSA-N CC1=C(C=C(C2=NC=CN12)C3=C(N=CC(=C3)N4CCOCC4)N)C5=CC6=C(C=C5)C=NN6 Chemical compound CC1=C(C=C(C2=NC=CN12)C3=C(N=CC(=C3)N4CCOCC4)N)C5=CC6=C(C=C5)C=NN6 NMCJRBJHRVNWMB-UHFFFAOYSA-N 0.000 description 1
- SYNHSKBCSXYITG-UHFFFAOYSA-N CC1=CC(=CC=C1)C2=CN3C=C(N=C3C(=N2)N)C4=CC(=C(C=C4)OC)OC Chemical compound CC1=CC(=CC=C1)C2=CN3C=C(N=C3C(=N2)N)C4=CC(=C(C=C4)OC)OC SYNHSKBCSXYITG-UHFFFAOYSA-N 0.000 description 1
- PWWFGSFXARXCJO-UHFFFAOYSA-N CC1=CC=C(C=C1)C2=CN3C=C(N=C3C(=N2)N)C4=CC(=C(C=C4)OC)OC Chemical compound CC1=CC=C(C=C1)C2=CN3C=C(N=C3C(=N2)N)C4=CC(=C(C=C4)OC)OC PWWFGSFXARXCJO-UHFFFAOYSA-N 0.000 description 1
- RDMYTVBSQJPBOC-UHFFFAOYSA-N CCC1C(CN1C2=CC=C(C=C2)NC3=NC(=CN4C3=NC=C4)C5=CC6=C(C=C5)C=NN6)O Chemical compound CCC1C(CN1C2=CC=C(C=C2)NC3=NC(=CN4C3=NC=C4)C5=CC6=C(C=C5)C=NN6)O RDMYTVBSQJPBOC-UHFFFAOYSA-N 0.000 description 1
- ARMSUXXMXHOYCT-UHFFFAOYSA-N CCN(CCO)C1=CC=C(C=C1)NC2=NC(=CN3C2=NC=C3)C4=CC5=C(C=C4)C(CN5)(C)C Chemical compound CCN(CCO)C1=CC=C(C=C1)NC2=NC(=CN3C2=NC=C3)C4=CC5=C(C=C4)C(CN5)(C)C ARMSUXXMXHOYCT-UHFFFAOYSA-N 0.000 description 1
- LVJGRDNPFNGVON-UHFFFAOYSA-N CCN1CNC2=C1C=CC(=C2)C3=CN4C=CN=C4C(=N3)NC5=CC=C(C=C5)N6CCOCC6 Chemical compound CCN1CNC2=C1C=CC(=C2)C3=CN4C=CN=C4C(=N3)NC5=CC=C(C=C5)N6CCOCC6 LVJGRDNPFNGVON-UHFFFAOYSA-N 0.000 description 1
- RRAVYYXFRFZEBV-UHFFFAOYSA-N CCNCC1=CC(=CC=C1)C2=CN3C=C(N=C3C(=N2)N)C4=CC(=C(C=C4)OC)OC Chemical compound CCNCC1=CC(=CC=C1)C2=CN3C=C(N=C3C(=N2)N)C4=CC(=C(C=C4)OC)OC RRAVYYXFRFZEBV-UHFFFAOYSA-N 0.000 description 1
- QNPVAUKCEOZKGT-UHFFFAOYSA-N CCNCC1=CC=C(C=C1)C2=CN3C=C(N=C3C(=N2)N)C4=CC(=C(C=C4)OC)OC Chemical compound CCNCC1=CC=C(C=C1)C2=CN3C=C(N=C3C(=N2)N)C4=CC(=C(C=C4)OC)OC QNPVAUKCEOZKGT-UHFFFAOYSA-N 0.000 description 1
- WCLLQEXJEMXPGQ-UHFFFAOYSA-N CCOC(C=C(C=C1)C2=CN(C=CN=C3N)C3=N2)=C1N1CCOCC1 Chemical compound CCOC(C=C(C=C1)C2=CN(C=CN=C3N)C3=N2)=C1N1CCOCC1 WCLLQEXJEMXPGQ-UHFFFAOYSA-N 0.000 description 1
- JMICFRUEVCUKAA-UHFFFAOYSA-N CCOC1=C(C=C(C=C1)C2=CN3C(=C(N=C(C3=N2)N)C4=CC5=C(C=C4)C=NN5)C)OC Chemical compound CCOC1=C(C=C(C=C1)C2=CN3C(=C(N=C(C3=N2)N)C4=CC5=C(C=C4)C=NN5)C)OC JMICFRUEVCUKAA-UHFFFAOYSA-N 0.000 description 1
- GYTIYBQOGSDWEK-UHFFFAOYSA-N CCOC1=C(C=C(C=C1)C2=CN3C=C(N=C(C3=N2)N)C4=CC(=C(C=C4)C)F)OC Chemical compound CCOC1=C(C=C(C=C1)C2=CN3C=C(N=C(C3=N2)N)C4=CC(=C(C=C4)C)F)OC GYTIYBQOGSDWEK-UHFFFAOYSA-N 0.000 description 1
- OSGIBKUZOJLACK-UHFFFAOYSA-N CCOC1=C(C=C(C=C1)C2=CN3C=C(N=C(C3=N2)N)C4=CC(=C(C=C4)F)C)OC Chemical compound CCOC1=C(C=C(C=C1)C2=CN3C=C(N=C(C3=N2)N)C4=CC(=C(C=C4)F)C)OC OSGIBKUZOJLACK-UHFFFAOYSA-N 0.000 description 1
- YFHKJWGNVRPZQS-UHFFFAOYSA-N CCOC1=C(C=C(C=C1)C2=CN3C=C(N=C(C3=N2)N)C4=CC(=CC=C4)F)OC Chemical compound CCOC1=C(C=C(C=C1)C2=CN3C=C(N=C(C3=N2)N)C4=CC(=CC=C4)F)OC YFHKJWGNVRPZQS-UHFFFAOYSA-N 0.000 description 1
- JYSAOCHRZKKLJF-UHFFFAOYSA-N CCOC1=C(C=C(C=C1)C2=CN3C=C(N=C(C3=N2)N)C4=CC(=CC=C4)S(=O)(=O)C)OC Chemical compound CCOC1=C(C=C(C=C1)C2=CN3C=C(N=C(C3=N2)N)C4=CC(=CC=C4)S(=O)(=O)C)OC JYSAOCHRZKKLJF-UHFFFAOYSA-N 0.000 description 1
- ZZPFOWKUWTUSSK-UHFFFAOYSA-N CCOC1=C(C=C(C=C1)C2=CN3C=C(N=C(C3=N2)N)C4=CC(=NC=C4)F)OC Chemical compound CCOC1=C(C=C(C=C1)C2=CN3C=C(N=C(C3=N2)N)C4=CC(=NC=C4)F)OC ZZPFOWKUWTUSSK-UHFFFAOYSA-N 0.000 description 1
- BUAGBTVPQRGUFF-UHFFFAOYSA-N CCOC1=C(C=C(C=C1)C2=CN3C=C(N=C(C3=N2)N)C4=CC5=C(C=CN5)N=C4)OC Chemical compound CCOC1=C(C=C(C=C1)C2=CN3C=C(N=C(C3=N2)N)C4=CC5=C(C=CN5)N=C4)OC BUAGBTVPQRGUFF-UHFFFAOYSA-N 0.000 description 1
- QVRSJZAJTPMGLX-UHFFFAOYSA-N CCOC1=C(C=C(C=C1)C2=CN3C=C(N=C(C3=N2)N)C4=CC=CC(=C4)C)OC Chemical compound CCOC1=C(C=C(C=C1)C2=CN3C=C(N=C(C3=N2)N)C4=CC=CC(=C4)C)OC QVRSJZAJTPMGLX-UHFFFAOYSA-N 0.000 description 1
- MGBZIICQZOUFIV-UHFFFAOYSA-N CCOC1=C(C=C(C=C1)C2=CN3C=C(N=C(C3=N2)N)C4=CN=CC(=C4)C)OC Chemical compound CCOC1=C(C=C(C=C1)C2=CN3C=C(N=C(C3=N2)N)C4=CN=CC(=C4)C)OC MGBZIICQZOUFIV-UHFFFAOYSA-N 0.000 description 1
- LMYXLDZDVOFQBX-UHFFFAOYSA-N CCOC1=C(C=C(C=C1)C2=CN3C=C(N=C(C3=N2)N)C4=CN=CN=C4)OC Chemical compound CCOC1=C(C=C(C=C1)C2=CN3C=C(N=C(C3=N2)N)C4=CN=CN=C4)OC LMYXLDZDVOFQBX-UHFFFAOYSA-N 0.000 description 1
- YGUMRQJXXXUJSB-UHFFFAOYSA-N CCOC1=C(C=CC(=C1)C2=CN3C=C(N=C(C3=N2)N)C4=CC5=C(C=C4)N=CN5C)N6CCOCC6 Chemical compound CCOC1=C(C=CC(=C1)C2=CN3C=C(N=C(C3=N2)N)C4=CC5=C(C=C4)N=CN5C)N6CCOCC6 YGUMRQJXXXUJSB-UHFFFAOYSA-N 0.000 description 1
- 101150075558 CHGA gene Proteins 0.000 description 1
- LPQRTGMGEXXQRV-UHFFFAOYSA-N CN(C)CCOC1=CC=C(C=C1)C2=CN3C=C(N=C(C3=N2)N)C4=CC5=C(C=C4)C=NN5 Chemical compound CN(C)CCOC1=CC=C(C=C1)C2=CN3C=C(N=C(C3=N2)N)C4=CC5=C(C=C4)C=NN5 LPQRTGMGEXXQRV-UHFFFAOYSA-N 0.000 description 1
- KBKVACGRTIZQPH-UHFFFAOYSA-N CN1CC(OC2=C1C=C(C=C2)N)C3=NC(=CN4C3=NC=C4)C5=CC6=C(C=C5)C=NN6 Chemical compound CN1CC(OC2=C1C=C(C=C2)N)C3=NC(=CN4C3=NC=C4)C5=CC6=C(C=C5)C=NN6 KBKVACGRTIZQPH-UHFFFAOYSA-N 0.000 description 1
- DPEYFNRZOFWBBM-UHFFFAOYSA-N CN1CC(OC2=C1C=C(C=C2)N)C3=NC(=CN4C3=NC=C4)C5=CC6=CN=C(N=C6C=C5)N Chemical compound CN1CC(OC2=C1C=C(C=C2)N)C3=NC(=CN4C3=NC=C4)C5=CC6=CN=C(N=C6C=C5)N DPEYFNRZOFWBBM-UHFFFAOYSA-N 0.000 description 1
- IUBLNVDPZVDVHI-UHFFFAOYSA-N CN1CC(OC2=C1C=CC(=C2)N)C3=NC(=CN4C3=NC=C4)C5=CC6=C(C=C5)C=NN6 Chemical compound CN1CC(OC2=C1C=CC(=C2)N)C3=NC(=CN4C3=NC=C4)C5=CC6=C(C=C5)C=NN6 IUBLNVDPZVDVHI-UHFFFAOYSA-N 0.000 description 1
- HTCAEIQGDQHUOQ-UHFFFAOYSA-N CN1CCC2=C(C1C3=NC(=CN4C3=NC=C4)C5=CC6=C(C=C5)C=NN6)C=CC(=C2)N Chemical compound CN1CCC2=C(C1C3=NC(=CN4C3=NC=C4)C5=CC6=C(C=C5)C=NN6)C=CC(=C2)N HTCAEIQGDQHUOQ-UHFFFAOYSA-N 0.000 description 1
- IGKYLANNBMRAFT-UHFFFAOYSA-N CN1CNC2=C1C=C(C=C2)C3=CN4C=CN=C4C(=N3)NC5=CC=C(C=C5)N6CCOCC6 Chemical compound CN1CNC2=C1C=C(C=C2)C3=CN4C=CN=C4C(=N3)NC5=CC=C(C=C5)N6CCOCC6 IGKYLANNBMRAFT-UHFFFAOYSA-N 0.000 description 1
- BJSFPVZKWNUWLZ-UHFFFAOYSA-N COC1=C(C=C(C=C1)C2=CN3C=C(N=C(C3=N2)N)C4=CC(=CC=C4)C(F)(F)F)OC Chemical compound COC1=C(C=C(C=C1)C2=CN3C=C(N=C(C3=N2)N)C4=CC(=CC=C4)C(F)(F)F)OC BJSFPVZKWNUWLZ-UHFFFAOYSA-N 0.000 description 1
- JCCABFIIOZUTND-UHFFFAOYSA-N COC1=C(C=C(C=C1)C2=CN3C=C(N=C(C3=N2)N)C4=CC(=CC=C4)OC)OC Chemical compound COC1=C(C=C(C=C1)C2=CN3C=C(N=C(C3=N2)N)C4=CC(=CC=C4)OC)OC JCCABFIIOZUTND-UHFFFAOYSA-N 0.000 description 1
- WIZJZBRWQQKSBI-UHFFFAOYSA-N COC1=C(C=C(C=C1)C2=CN3C=C(N=C(C3=N2)N)C4=CC(=CC=C4)[N+](=O)[O-])OC Chemical compound COC1=C(C=C(C=C1)C2=CN3C=C(N=C(C3=N2)N)C4=CC(=CC=C4)[N+](=O)[O-])OC WIZJZBRWQQKSBI-UHFFFAOYSA-N 0.000 description 1
- IASLXMJVLKLBQD-UHFFFAOYSA-N COC1=C(C=C(C=C1)C2=CN3C=C(N=C(C3=N2)N)C4=CC5=C(C=C4)N=CC=C5)OC Chemical compound COC1=C(C=C(C=C1)C2=CN3C=C(N=C(C3=N2)N)C4=CC5=C(C=C4)N=CC=C5)OC IASLXMJVLKLBQD-UHFFFAOYSA-N 0.000 description 1
- SKMCXKZRJAWFBI-UHFFFAOYSA-N COC1=C(C=C(C=C1)C2=CN3C=C(N=C(C3=N2)N)C4=CC5=C(C=C4)NN=C5)OC Chemical compound COC1=C(C=C(C=C1)C2=CN3C=C(N=C(C3=N2)N)C4=CC5=C(C=C4)NN=C5)OC SKMCXKZRJAWFBI-UHFFFAOYSA-N 0.000 description 1
- UJALORLRIWIWOQ-UHFFFAOYSA-N COC1=C(C=C(C=C1)C2=CN3C=C(N=C(C3=N2)N)C4=CC5=C(C=CN5)N=C4)OC Chemical compound COC1=C(C=C(C=C1)C2=CN3C=C(N=C(C3=N2)N)C4=CC5=C(C=CN5)N=C4)OC UJALORLRIWIWOQ-UHFFFAOYSA-N 0.000 description 1
- ZPIHNNNQIDGAJK-UHFFFAOYSA-N COC1=C(C=C(C=C1)C2=CN3C=C(N=C(C3=N2)N)C4=CC=C(C=C4)C5=NC=CN5)OC Chemical compound COC1=C(C=C(C=C1)C2=CN3C=C(N=C(C3=N2)N)C4=CC=C(C=C4)C5=NC=CN5)OC ZPIHNNNQIDGAJK-UHFFFAOYSA-N 0.000 description 1
- CFXCGKQNXGZNJN-UHFFFAOYSA-N COC1=C(C=C(C=C1)C2=CN3C=C(N=C(C3=N2)N)C4=CC=C(C=C4)F)OC Chemical compound COC1=C(C=C(C=C1)C2=CN3C=C(N=C(C3=N2)N)C4=CC=C(C=C4)F)OC CFXCGKQNXGZNJN-UHFFFAOYSA-N 0.000 description 1
- FGSJHTGZBGYDIT-UHFFFAOYSA-N COC1=C(C=C(C=C1)C2=CN3C=C(N=C(C3=N2)N)C4=CC=C(C=C4)S(=O)(=O)C)OC Chemical compound COC1=C(C=C(C=C1)C2=CN3C=C(N=C(C3=N2)N)C4=CC=C(C=C4)S(=O)(=O)C)OC FGSJHTGZBGYDIT-UHFFFAOYSA-N 0.000 description 1
- JHJJTIWDZNIWNR-UHFFFAOYSA-N COC1=C(C=C(C=C1)C2=CN3C=C(N=C(C3=N2)N)C4=CC=CC=C4)OC Chemical compound COC1=C(C=C(C=C1)C2=CN3C=C(N=C(C3=N2)N)C4=CC=CC=C4)OC JHJJTIWDZNIWNR-UHFFFAOYSA-N 0.000 description 1
- VNQDADZXKKPUGX-UHFFFAOYSA-N COC1=C(C=C(C=C1)C2=CN3C=C(N=C(C3=N2)N)C4=CC=NC=C4)OC Chemical compound COC1=C(C=C(C=C1)C2=CN3C=C(N=C(C3=N2)N)C4=CC=NC=C4)OC VNQDADZXKKPUGX-UHFFFAOYSA-N 0.000 description 1
- XGZOSJJSPOWPTF-UHFFFAOYSA-N COC1=C(C=C(C=C1)C2=CN3C=C(N=C(C3=N2)N)C4=CN=CC=C4)OC Chemical compound COC1=C(C=C(C=C1)C2=CN3C=C(N=C(C3=N2)N)C4=CN=CC=C4)OC XGZOSJJSPOWPTF-UHFFFAOYSA-N 0.000 description 1
- DPSVGVIBNWYAPO-UHFFFAOYSA-N COC1=C(C=C(C=C1)C2=CN3C=C(N=C(C3=N2)N)C4=CSC=C4)OC Chemical compound COC1=C(C=C(C=C1)C2=CN3C=C(N=C(C3=N2)N)C4=CSC=C4)OC DPSVGVIBNWYAPO-UHFFFAOYSA-N 0.000 description 1
- VXLMJYLRACUVBR-UHFFFAOYSA-N COC1=C(C=CC(=C1)C2=CN3C=C(N=C(C3=N2)N)C4=CC5=C(C=CN5)N=C4)N6CCOCC6 Chemical compound COC1=C(C=CC(=C1)C2=CN3C=C(N=C(C3=N2)N)C4=CC5=C(C=CN5)N=C4)N6CCOCC6 VXLMJYLRACUVBR-UHFFFAOYSA-N 0.000 description 1
- UIGABPACHSUMEQ-UHFFFAOYSA-N COC1=C(C=CC(=C1)NC2=NC(=C(N3C2=NC=C3)Cl)C4=CC5=C(CCN5)C=C4)N6CCOCC6 Chemical compound COC1=C(C=CC(=C1)NC2=NC(=C(N3C2=NC=C3)Cl)C4=CC5=C(CCN5)C=C4)N6CCOCC6 UIGABPACHSUMEQ-UHFFFAOYSA-N 0.000 description 1
- KRQSVXITWTXISN-UHFFFAOYSA-N COC1=C(C=CC(=C1CCO)NC2=NC(=CN3C2=NC=C3)C4=CC5=C(C=C4)C=NN5)C(=O)N Chemical compound COC1=C(C=CC(=C1CCO)NC2=NC(=CN3C2=NC=C3)C4=CC5=C(C=C4)C=NN5)C(=O)N KRQSVXITWTXISN-UHFFFAOYSA-N 0.000 description 1
- YFNTUDBDISWIFL-UHFFFAOYSA-N COC1=CC(=C(C=C1)C2=CN3C=C(N=C(C3=N2)N)C4=CC5=C(C=C4)C=NN5)F Chemical compound COC1=CC(=C(C=C1)C2=CN3C=C(N=C(C3=N2)N)C4=CC5=C(C=C4)C=NN5)F YFNTUDBDISWIFL-UHFFFAOYSA-N 0.000 description 1
- RJHHGVGXSRNLFY-UHFFFAOYSA-N COCC(C=C(C=C1)C2=CN(C=CN=C3N)C3=N2)=C1N1CCOCC1 Chemical compound COCC(C=C(C=C1)C2=CN(C=CN=C3N)C3=N2)=C1N1CCOCC1 RJHHGVGXSRNLFY-UHFFFAOYSA-N 0.000 description 1
- RUPBDHFNSRKULQ-UHFFFAOYSA-N COCCOC(C=CC(C1=CN(C=CN=C2N)C2=N1)=C1)=C1OC Chemical compound COCCOC(C=CC(C1=CN(C=CN=C2N)C2=N1)=C1)=C1OC RUPBDHFNSRKULQ-UHFFFAOYSA-N 0.000 description 1
- KLWPJMFMVPTNCC-UHFFFAOYSA-N Camptothecin Natural products CCC1(O)C(=O)OCC2=C1C=C3C4Nc5ccccc5C=C4CN3C2=O KLWPJMFMVPTNCC-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- DLGOEMSEDOSKAD-UHFFFAOYSA-N Carmustine Chemical compound ClCCNC(=O)N(N=O)CCCl DLGOEMSEDOSKAD-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 108010009685 Cholinergic Receptors Proteins 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- MFYSYFVPBJMHGN-ZPOLXVRWSA-N Cortisone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 MFYSYFVPBJMHGN-ZPOLXVRWSA-N 0.000 description 1
- MFYSYFVPBJMHGN-UHFFFAOYSA-N Cortisone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 MFYSYFVPBJMHGN-UHFFFAOYSA-N 0.000 description 1
- 208000011231 Crohn disease Diseases 0.000 description 1
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 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 description 1
- 108010036949 Cyclosporine Proteins 0.000 description 1
- 229940123780 DNA topoisomerase I inhibitor Drugs 0.000 description 1
- 229940124087 DNA topoisomerase II inhibitor Drugs 0.000 description 1
- WEAHRLBPCANXCN-UHFFFAOYSA-N Daunomycin Natural products CCC1(O)CC(OC2CC(N)C(O)C(C)O2)c3cc4C(=O)c5c(OC)cccc5C(=O)c4c(O)c3C1 WEAHRLBPCANXCN-UHFFFAOYSA-N 0.000 description 1
- 229940124186 Dehydrogenase inhibitor Drugs 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- LTMHDMANZUZIPE-AMTYYWEZSA-N Digoxin Natural products O([C@H]1[C@H](C)O[C@H](O[C@@H]2C[C@@H]3[C@@](C)([C@@H]4[C@H]([C@]5(O)[C@](C)([C@H](O)C4)[C@H](C4=CC(=O)OC4)CC5)CC3)CC2)C[C@@H]1O)[C@H]1O[C@H](C)[C@@H](O[C@H]2O[C@@H](C)[C@H](O)[C@@H](O)C2)[C@@H](O)C1 LTMHDMANZUZIPE-AMTYYWEZSA-N 0.000 description 1
- 229940117937 Dihydrofolate reductase inhibitor Drugs 0.000 description 1
- 206010061818 Disease progression Diseases 0.000 description 1
- 206010059866 Drug resistance Diseases 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 208000004232 Enteritis Diseases 0.000 description 1
- 240000000731 Fagus sylvatica Species 0.000 description 1
- 235000010099 Fagus sylvatica Nutrition 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- 208000007882 Gastritis Diseases 0.000 description 1
- 108010024636 Glutathione Proteins 0.000 description 1
- 208000024869 Goodpasture syndrome Diseases 0.000 description 1
- 102100039121 Histone-lysine N-methyltransferase MECOM Human genes 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 101001033728 Homo sapiens Histone-lysine N-methyltransferase MECOM Proteins 0.000 description 1
- 108090000144 Human Proteins Proteins 0.000 description 1
- 102000003839 Human Proteins Human genes 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 description 1
- 102000055031 Inhibitor of Apoptosis Proteins Human genes 0.000 description 1
- 102000004877 Insulin Human genes 0.000 description 1
- 108090001061 Insulin Proteins 0.000 description 1
- 208000008839 Kidney Neoplasms Diseases 0.000 description 1
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- 108010022337 Leucine Enkephalin Proteins 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- MQHWFIOJQSCFNM-UHFFFAOYSA-L Magnesium salicylate Chemical class [Mg+2].OC1=CC=CC=C1C([O-])=O.OC1=CC=CC=C1C([O-])=O MQHWFIOJQSCFNM-UHFFFAOYSA-L 0.000 description 1
- 201000009906 Meningitis Diseases 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- FQISKWAFAHGMGT-SGJOWKDISA-M Methylprednisolone sodium succinate Chemical compound [Na+].C([C@@]12C)=CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2[C@@H](O)C[C@]2(C)[C@@](O)(C(=O)COC(=O)CCC([O-])=O)CC[C@H]21 FQISKWAFAHGMGT-SGJOWKDISA-M 0.000 description 1
- 241001529936 Murinae Species 0.000 description 1
- 101100091501 Mus musculus Ros1 gene Proteins 0.000 description 1
- 208000009525 Myocarditis Diseases 0.000 description 1
- 201000002481 Myositis Diseases 0.000 description 1
- SJLUFUJUVSXDGR-UHFFFAOYSA-N N1(CCOCC1)C(=O)C1=CC=C(C=C1)C=1N=C2N(C=CN=C2N)C=1 Chemical compound N1(CCOCC1)C(=O)C1=CC=C(C=C1)C=1N=C2N(C=CN=C2N)C=1 SJLUFUJUVSXDGR-UHFFFAOYSA-N 0.000 description 1
- YYPSXAQCGONJMV-UHFFFAOYSA-N NC1=NC=CN2C1=NC(C(C=C1)=CC=C1N(C1)CC11CCOCC1)=C2 Chemical compound NC1=NC=CN2C1=NC(C(C=C1)=CC=C1N(C1)CC11CCOCC1)=C2 YYPSXAQCGONJMV-UHFFFAOYSA-N 0.000 description 1
- UIMJMNRBVNNHCS-UHFFFAOYSA-N NC1=NC=CN2C1=NC(C(C=C1)=CC=C1N1CCNCC1)=C2 Chemical compound NC1=NC=CN2C1=NC(C(C=C1)=CC=C1N1CCNCC1)=C2 UIMJMNRBVNNHCS-UHFFFAOYSA-N 0.000 description 1
- DXDYTXNFFZEQDT-UHFFFAOYSA-N NC1=NC=CN2C1=NC(C(C=C1)=CC=C1N1CCOCCC1)=C2 Chemical compound NC1=NC=CN2C1=NC(C(C=C1)=CC=C1N1CCOCCC1)=C2 DXDYTXNFFZEQDT-UHFFFAOYSA-N 0.000 description 1
- PFUSTLUMEGTLRN-UHFFFAOYSA-N NC1=NC=CN2C1=NC(C(C=C1)=CC=C1OC1=CC=NC=C1)=C2 Chemical compound NC1=NC=CN2C1=NC(C(C=C1)=CC=C1OC1=CC=NC=C1)=C2 PFUSTLUMEGTLRN-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 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 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 206010031252 Osteomyelitis Diseases 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 206010033645 Pancreatitis Diseases 0.000 description 1
- 208000018737 Parkinson disease Diseases 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
- 206010035664 Pneumonia Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 102100038277 Prostaglandin G/H synthase 1 Human genes 0.000 description 1
- 108050003243 Prostaglandin G/H synthase 1 Proteins 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- 206010037394 Pulmonary haemorrhage Diseases 0.000 description 1
- 108010052300 RA X peptide Proteins 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 206010038389 Renal cancer Diseases 0.000 description 1
- 206010039710 Scleroderma Diseases 0.000 description 1
- 208000034189 Sclerosis Diseases 0.000 description 1
- 206010040070 Septic Shock Diseases 0.000 description 1
- ABBQHOQBGMUPJH-UHFFFAOYSA-M Sodium salicylate Chemical compound [Na+].OC1=CC=CC=C1C([O-])=O ABBQHOQBGMUPJH-UHFFFAOYSA-M 0.000 description 1
- 108010090804 Streptavidin Proteins 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 206010042496 Sunburn Diseases 0.000 description 1
- 102000016266 T-Cell Antigen Receptors Human genes 0.000 description 1
- 108010092262 T-Cell Antigen Receptors Proteins 0.000 description 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 description 1
- 239000000365 Topoisomerase I Inhibitor Substances 0.000 description 1
- 239000000317 Topoisomerase II Inhibitor Substances 0.000 description 1
- 206010052779 Transplant rejections Diseases 0.000 description 1
- 102000004243 Tubulin Human genes 0.000 description 1
- 108090000704 Tubulin Proteins 0.000 description 1
- 108060008683 Tumor Necrosis Factor Receptor Proteins 0.000 description 1
- 206010046851 Uveitis Diseases 0.000 description 1
- JXLYSJRDGCGARV-WWYNWVTFSA-N Vinblastine Natural products O=C(O[C@H]1[C@](O)(C(=O)OC)[C@@H]2N(C)c3c(cc(c(OC)c3)[C@]3(C(=O)OC)c4[nH]c5c(c4CCN4C[C@](O)(CC)C[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C JXLYSJRDGCGARV-WWYNWVTFSA-N 0.000 description 1
- LWWVQVGXDWYJOU-UHFFFAOYSA-N [1-[4-[[6-(1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]piperidin-4-yl]methanol Chemical compound C1CC(CO)CCN1C(C=C1)=CC=C1NC1=NC(C=2C=C3NN=CC3=CC=2)=CN2C1=NC=C2 LWWVQVGXDWYJOU-UHFFFAOYSA-N 0.000 description 1
- LAJHOCMCZGEKQK-UHFFFAOYSA-N [1-[4-[[6-(1h-pyrrolo[3,2-b]pyridin-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]piperidin-4-yl]methanol Chemical compound C1CC(CO)CCN1C(C=C1)=CC=C1NC1=NC(C=2C=C3NC=CC3=NC=2)=CN2C1=NC=C2 LAJHOCMCZGEKQK-UHFFFAOYSA-N 0.000 description 1
- HJRZWXZGHDWTTB-UHFFFAOYSA-N [2-(hydroxymethyl)morpholin-4-yl]-[4-[[6-(1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]methanone Chemical compound C1COC(CO)CN1C(=O)C(C=C1)=CC=C1NC1=NC(C=2C=C3NN=CC3=CC=2)=CN2C1=NC=C2 HJRZWXZGHDWTTB-UHFFFAOYSA-N 0.000 description 1
- FMUQGYRBBXAGDT-UHFFFAOYSA-N [2-[8-(4-morpholin-4-ylanilino)imidazo[1,2-a]pyrazin-6-yl]phenyl]methanol Chemical compound OCC1=CC=CC=C1C(N=C1NC=2C=CC(=CC=2)N2CCOCC2)=CN2C1=NC=C2 FMUQGYRBBXAGDT-UHFFFAOYSA-N 0.000 description 1
- PNLIGKWHLWTAGK-UHFFFAOYSA-N [2-methoxy-5-[[6-(3-methylbenzimidazol-5-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]methanol Chemical compound C1=C(CO)C(OC)=CC=C1NC1=NC(C=2C=C3N(C)C=NC3=CC=2)=CN2C1=NC=C2 PNLIGKWHLWTAGK-UHFFFAOYSA-N 0.000 description 1
- YSVZGWAJIHWNQK-UHFFFAOYSA-N [3-(hydroxymethyl)-2-bicyclo[2.2.1]heptanyl]methanol Chemical compound C1CC2C(CO)C(CO)C1C2 YSVZGWAJIHWNQK-UHFFFAOYSA-N 0.000 description 1
- MYCNLLRYYDOFGC-UHFFFAOYSA-N [4-[4-[[6-(1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]morpholin-2-yl]methanol Chemical compound C1COC(CO)CN1C(C=C1)=CC=C1NC1=NC(C=2C=C3NN=CC3=CC=2)=CN2C1=NC=C2 MYCNLLRYYDOFGC-UHFFFAOYSA-N 0.000 description 1
- BMFBLXSIFKIKRK-UHFFFAOYSA-N [4-[[6-(1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]-2-methoxyphenyl]methanol Chemical compound C1=C(CO)C(OC)=CC(NC=2C3=NC=CN3C=C(N=2)C=2C=C3NN=CC3=CC=2)=C1 BMFBLXSIFKIKRK-UHFFFAOYSA-N 0.000 description 1
- IIEINJSQIQOIJR-UHFFFAOYSA-N [5-[[6-(1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]-2-methoxyphenyl]methanol Chemical compound C1=C(CO)C(OC)=CC=C1NC1=NC(C=2C=C3NN=CC3=CC=2)=CN2C1=NC=C2 IIEINJSQIQOIJR-UHFFFAOYSA-N 0.000 description 1
- IHDIBQVRAKBPCU-UHFFFAOYSA-N [6-[8-(4-morpholin-4-ylanilino)imidazo[1,2-a]pyrazin-6-yl]-2h-indazol-3-yl]methanol Chemical compound C=1C=C2C(CO)=NNC2=CC=1C(N=1)=CN2C=CN=C2C=1NC(C=C1)=CC=C1N1CCOCC1 IHDIBQVRAKBPCU-UHFFFAOYSA-N 0.000 description 1
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 description 1
- 230000001594 aberrant effect Effects 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 1
- 102000034337 acetylcholine receptors Human genes 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 230000003113 alkalizing effect Effects 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 239000013566 allergen Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001413 amino acids Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 239000000074 antisense oligonucleotide Substances 0.000 description 1
- 238000012230 antisense oligonucleotides Methods 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 229940114079 arachidonic acid Drugs 0.000 description 1
- 235000021342 arachidonic acid Nutrition 0.000 description 1
- 125000005160 aryl oxy alkyl group Chemical group 0.000 description 1
- 238000011914 asymmetric synthesis Methods 0.000 description 1
- AUJRCFUBUPVWSZ-XTZHGVARSA-M auranofin Chemical compound CCP(CC)(CC)=[Au]S[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O AUJRCFUBUPVWSZ-XTZHGVARSA-M 0.000 description 1
- 229960005207 auranofin Drugs 0.000 description 1
- 208000037979 autoimmune inflammatory disease Diseases 0.000 description 1
- VSRXQHXAPYXROS-UHFFFAOYSA-N azanide;cyclobutane-1,1-dicarboxylic acid;platinum(2+) Chemical compound [NH2-].[NH2-].[Pt+2].OC(=O)C1(C(O)=O)CCC1 VSRXQHXAPYXROS-UHFFFAOYSA-N 0.000 description 1
- LMEKQMALGUDUQG-UHFFFAOYSA-N azathioprine Chemical compound CN1C=NC([N+]([O-])=O)=C1SC1=NC=NC2=C1NC=N2 LMEKQMALGUDUQG-UHFFFAOYSA-N 0.000 description 1
- 229960002170 azathioprine Drugs 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 210000003651 basophil Anatomy 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- IQFYYKKMVGJFEH-UHFFFAOYSA-N beta-L-thymidine Natural products O=C1NC(=O)C(C)=CN1C1OC(CO)C(O)C1 IQFYYKKMVGJFEH-UHFFFAOYSA-N 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 125000006580 bicyclic heterocycloalkyl group Chemical group 0.000 description 1
- 238000004166 bioassay Methods 0.000 description 1
- 239000003124 biologic agent Substances 0.000 description 1
- 230000031018 biological processes and functions Effects 0.000 description 1
- 230000008512 biological response Effects 0.000 description 1
- 229960002685 biotin Drugs 0.000 description 1
- 235000020958 biotin Nutrition 0.000 description 1
- 239000011616 biotin Substances 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 229940098773 bovine serum albumin Drugs 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000005510 but-1-en-2-yl group Chemical group 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229960005069 calcium Drugs 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 229940127093 camptothecin Drugs 0.000 description 1
- VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical compound C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 description 1
- 229960004562 carboplatin Drugs 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000012754 cardiac puncture Methods 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- FLKYBGKDCCEQQM-WYUVZMMLSA-M cefazolin sodium Chemical compound [Na+].S1C(C)=NN=C1SCC1=C(C([O-])=O)N2C(=O)[C@@H](NC(=O)CN3N=NN=C3)[C@H]2SC1 FLKYBGKDCCEQQM-WYUVZMMLSA-M 0.000 description 1
- 229960000590 celecoxib Drugs 0.000 description 1
- RZEKVGVHFLEQIL-UHFFFAOYSA-N celecoxib Chemical compound C1=CC(C)=CC=C1C1=CC(C(F)(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 RZEKVGVHFLEQIL-UHFFFAOYSA-N 0.000 description 1
- 238000000423 cell based assay Methods 0.000 description 1
- 239000013592 cell lysate Substances 0.000 description 1
- 238000001516 cell proliferation assay Methods 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 201000001352 cholecystitis Diseases 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- 208000025302 chronic primary adrenal insufficiency Diseases 0.000 description 1
- 229960001265 ciclosporin Drugs 0.000 description 1
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 1
- 229960004316 cisplatin Drugs 0.000 description 1
- 238000010668 complexation reaction Methods 0.000 description 1
- 229920001577 copolymer Chemical compound 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 229960001334 corticosteroids Drugs 0.000 description 1
- 229960004544 cortisone Drugs 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 description 1
- KTHXBEHDVMTNOH-UHFFFAOYSA-N cyclobutanol Chemical compound OC1CCC1 KTHXBEHDVMTNOH-UHFFFAOYSA-N 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 229960004397 cyclophosphamide Drugs 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 229930182912 cyclosporin Natural products 0.000 description 1
- 230000009089 cytolysis Effects 0.000 description 1
- 210000000805 cytoplasm Anatomy 0.000 description 1
- 238000013480 data collection Methods 0.000 description 1
- STQGQHZAVUOBTE-VGBVRHCVSA-N daunorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(C)=O)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 STQGQHZAVUOBTE-VGBVRHCVSA-N 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 210000004443 dendritic cell Anatomy 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 201000001981 dermatomyositis Diseases 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 229960003957 dexamethasone Drugs 0.000 description 1
- UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- VILAVOFMIJHSJA-UHFFFAOYSA-N dicarbon monoxide Chemical compound [C]=C=O VILAVOFMIJHSJA-UHFFFAOYSA-N 0.000 description 1
- 229960001259 diclofenac Drugs 0.000 description 1
- DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 description 1
- 229960001193 diclofenac sodium Drugs 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- HUPFGZXOMWLGNK-UHFFFAOYSA-N diflunisal Chemical compound C1=C(O)C(C(=O)O)=CC(C=2C(=CC(F)=CC=2)F)=C1 HUPFGZXOMWLGNK-UHFFFAOYSA-N 0.000 description 1
- 229960000616 diflunisal Drugs 0.000 description 1
- LTMHDMANZUZIPE-PUGKRICDSA-N digoxin Chemical compound C1[C@H](O)[C@H](O)[C@@H](C)O[C@H]1O[C@@H]1[C@@H](C)O[C@@H](O[C@@H]2[C@H](O[C@@H](O[C@@H]3C[C@@H]4[C@]([C@@H]5[C@H]([C@]6(CC[C@@H]([C@@]6(C)[C@H](O)C5)C=5COC(=O)C=5)O)CC4)(C)CC3)C[C@@H]2O)C)C[C@@H]1O LTMHDMANZUZIPE-PUGKRICDSA-N 0.000 description 1
- 229960005156 digoxin Drugs 0.000 description 1
- LTMHDMANZUZIPE-UHFFFAOYSA-N digoxine Natural products C1C(O)C(O)C(C)OC1OC1C(C)OC(OC2C(OC(OC3CC4C(C5C(C6(CCC(C6(C)C(O)C5)C=5COC(=O)C=5)O)CC4)(C)CC3)CC2O)C)CC1O LTMHDMANZUZIPE-UHFFFAOYSA-N 0.000 description 1
- 239000003166 dihydrofolate reductase inhibitor Substances 0.000 description 1
- 108091022884 dihydropyrimidinase Proteins 0.000 description 1
- 239000001177 diphosphate Substances 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
- 235000011180 diphosphates Nutrition 0.000 description 1
- 230000006806 disease prevention Effects 0.000 description 1
- 230000005750 disease progression Effects 0.000 description 1
- VXIHRIQNJCRFQX-UHFFFAOYSA-K disodium aurothiomalate Chemical compound [Na+].[Na+].[O-]C(=O)CC(S[Au])C([O-])=O VXIHRIQNJCRFQX-UHFFFAOYSA-K 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- VHJLVAABSRFDPM-QWWZWVQMSA-N dithiothreitol Chemical compound SC[C@@H](O)[C@H](O)CS VHJLVAABSRFDPM-QWWZWVQMSA-N 0.000 description 1
- VSJKWCGYPAHWDS-UHFFFAOYSA-N dl-camptothecin Natural products C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)C5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-UHFFFAOYSA-N 0.000 description 1
- 230000007783 downstream signaling Effects 0.000 description 1
- 229960004679 doxorubicin Drugs 0.000 description 1
- 210000005069 ears Anatomy 0.000 description 1
- 229960002224 eculizumab Drugs 0.000 description 1
- 238000000132 electrospray ionisation Methods 0.000 description 1
- 230000009881 electrostatic interaction Effects 0.000 description 1
- 206010014599 encephalitis Diseases 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 239000002532 enzyme inhibitor Substances 0.000 description 1
- 210000003743 erythrocyte Anatomy 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- XFBVBWWRPKNWHW-UHFFFAOYSA-N etodolac Chemical compound C1COC(CC)(CC(O)=O)C2=N[C]3C(CC)=CC=CC3=C21 XFBVBWWRPKNWHW-UHFFFAOYSA-N 0.000 description 1
- 229960005293 etodolac Drugs 0.000 description 1
- 229960004945 etoricoxib Drugs 0.000 description 1
- MNJVRJDLRVPLFE-UHFFFAOYSA-N etoricoxib Chemical compound C1=NC(C)=CC=C1C1=NC=C(Cl)C=C1C1=CC=C(S(C)(=O)=O)C=C1 MNJVRJDLRVPLFE-UHFFFAOYSA-N 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000008622 extracellular signaling Effects 0.000 description 1
- 230000002550 fecal effect Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
- 238000001917 fluorescence detection Methods 0.000 description 1
- 238000002795 fluorescence method Methods 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 229960002390 flurbiprofen Drugs 0.000 description 1
- SYTBZMRGLBWNTM-UHFFFAOYSA-N flurbiprofen Chemical compound FC1=CC(C(C(O)=O)C)=CC=C1C1=CC=CC=C1 SYTBZMRGLBWNTM-UHFFFAOYSA-N 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 208000007565 gingivitis Diseases 0.000 description 1
- 229960003180 glutathione Drugs 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 230000002949 hemolytic effect Effects 0.000 description 1
- 208000006454 hepatitis Diseases 0.000 description 1
- 231100000283 hepatitis Toxicity 0.000 description 1
- 125000005844 heterocyclyloxy group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- DOUHZFSGSXMPIE-UHFFFAOYSA-N hydroxidooxidosulfur(.) Chemical compound [O]SO DOUHZFSGSXMPIE-UHFFFAOYSA-N 0.000 description 1
- XXSMGPRMXLTPCZ-UHFFFAOYSA-N hydroxychloroquine Chemical compound ClC1=CC=C2C(NC(C)CCCN(CCO)CC)=CC=NC2=C1 XXSMGPRMXLTPCZ-UHFFFAOYSA-N 0.000 description 1
- 229960004171 hydroxychloroquine Drugs 0.000 description 1
- 230000009610 hypersensitivity Effects 0.000 description 1
- 229960001680 ibuprofen Drugs 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 230000001506 immunosuppresive effect Effects 0.000 description 1
- 229960003444 immunosuppressant agent Drugs 0.000 description 1
- 239000003018 immunosuppressive agent Substances 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 229960000905 indomethacin Drugs 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 230000036512 infertility Effects 0.000 description 1
- 230000008595 infiltration Effects 0.000 description 1
- 238000001764 infiltration Methods 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 230000028709 inflammatory response Effects 0.000 description 1
- 229960000598 infliximab Drugs 0.000 description 1
- 230000015788 innate immune response Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229940125396 insulin Drugs 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 208000002551 irritable bowel syndrome Diseases 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 238000005304 joining Methods 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 201000010982 kidney cancer Diseases 0.000 description 1
- URLZCHNOLZSCCA-UHFFFAOYSA-N leu-enkephalin Chemical compound C=1C=C(O)C=CC=1CC(N)C(=O)NCC(=O)NCC(=O)NC(C(=O)NC(CC(C)C)C(O)=O)CC1=CC=CC=C1 URLZCHNOLZSCCA-UHFFFAOYSA-N 0.000 description 1
- 210000000265 leukocyte Anatomy 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 238000012417 linear regression Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000012160 loading buffer Substances 0.000 description 1
- 229960000994 lumiracoxib Drugs 0.000 description 1
- KHPKQFYUPIUARC-UHFFFAOYSA-N lumiracoxib Chemical compound OC(=O)CC1=CC(C)=CC=C1NC1=C(F)C=CC=C1Cl KHPKQFYUPIUARC-UHFFFAOYSA-N 0.000 description 1
- 239000006166 lysate Substances 0.000 description 1
- 239000012139 lysis buffer Substances 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 210000002540 macrophage Anatomy 0.000 description 1
- 239000006249 magnetic particle Substances 0.000 description 1
- 229940049920 malate Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000035800 maturation Effects 0.000 description 1
- 210000003519 mature b lymphocyte Anatomy 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- SGDBTWWWUNNDEQ-LBPRGKRZSA-N melphalan Chemical compound OC(=O)[C@@H](N)CC1=CC=C(N(CCCl)CCCl)C=C1 SGDBTWWWUNNDEQ-LBPRGKRZSA-N 0.000 description 1
- 229960001924 melphalan Drugs 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- FBBDOOHMGLLEGJ-UHFFFAOYSA-N methane;hydrochloride Chemical compound C.Cl FBBDOOHMGLLEGJ-UHFFFAOYSA-N 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- OJLOPKGSLYJEMD-URPKTTJQSA-N methyl 7-[(1r,2r,3r)-3-hydroxy-2-[(1e)-4-hydroxy-4-methyloct-1-en-1-yl]-5-oxocyclopentyl]heptanoate Chemical compound CCCCC(C)(O)C\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(=O)OC OJLOPKGSLYJEMD-URPKTTJQSA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 229960004584 methylprednisolone Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 229960005249 misoprostol Drugs 0.000 description 1
- 229960004857 mitomycin Drugs 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- RTGDFNSFWBGLEC-SYZQJQIISA-N mycophenolate mofetil Chemical compound COC1=C(C)C=2COC(=O)C=2C(O)=C1C\C=C(/C)CCC(=O)OCCN1CCOCC1 RTGDFNSFWBGLEC-SYZQJQIISA-N 0.000 description 1
- 229960004866 mycophenolate mofetil Drugs 0.000 description 1
- VABLXPYNIUSDPJ-UHFFFAOYSA-N n-(3,4-dimethoxyphenyl)-6-(4-methylphenyl)imidazo[1,2-a]pyrazin-8-amine Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC(C=2C=CC(C)=CC=2)=CN2C1=NC=C2 VABLXPYNIUSDPJ-UHFFFAOYSA-N 0.000 description 1
- RHGWNVCYUPEFJE-UHFFFAOYSA-N n-(3,4-dimethoxyphenyl)-6-quinolin-6-ylimidazo[1,2-a]pyrazin-8-amine Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC(C=2C=C3C=CC=NC3=CC=2)=CN2C1=NC=C2 RHGWNVCYUPEFJE-UHFFFAOYSA-N 0.000 description 1
- NYDBRMPLLYGSJP-UHFFFAOYSA-N n-(3-ethoxy-4-morpholin-4-ylphenyl)-6-(4-fluoro-1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-amine Chemical compound CCOC1=CC(NC=2C3=NC=CN3C=C(N=2)C=2C=C3NN=CC3=C(F)C=2)=CC=C1N1CCOCC1 NYDBRMPLLYGSJP-UHFFFAOYSA-N 0.000 description 1
- WJWXHSWZIYEVCT-UHFFFAOYSA-N n-(3-methoxy-4-morpholin-4-ylphenyl)-6-(1-methylindazol-6-yl)imidazo[1,2-a]pyrazin-8-amine Chemical compound COC1=CC(NC=2C3=NC=CN3C=C(N=2)C=2C=C3N(C)N=CC3=CC=2)=CC=C1N1CCOCC1 WJWXHSWZIYEVCT-UHFFFAOYSA-N 0.000 description 1
- GUMBTSUAFNYGDT-UHFFFAOYSA-N n-(3-methoxy-4-morpholin-4-ylphenyl)-6-(3-methyl-2h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-amine Chemical compound COC1=CC(NC=2C3=NC=CN3C=C(N=2)C=2C=C3NN=C(C)C3=CC=2)=CC=C1N1CCOCC1 GUMBTSUAFNYGDT-UHFFFAOYSA-N 0.000 description 1
- QZGNJFJEDIJHBI-UHFFFAOYSA-N n-(3-methoxy-4-morpholin-4-ylphenyl)-6-(5-methoxypyridin-3-yl)imidazo[1,2-a]pyrazin-8-amine Chemical compound COC1=CN=CC(C=2N=C(NC=3C=C(OC)C(N4CCOCC4)=CC=3)C3=NC=CN3C=2)=C1 QZGNJFJEDIJHBI-UHFFFAOYSA-N 0.000 description 1
- BGDRABCWYKFIBU-UHFFFAOYSA-N n-(3-methoxy-4-morpholin-4-ylphenyl)-6-(6-methoxypyridin-3-yl)imidazo[1,2-a]pyrazin-8-amine Chemical compound C1=NC(OC)=CC=C1C(N=C1NC=2C=C(OC)C(N3CCOCC3)=CC=2)=CN2C1=NC=C2 BGDRABCWYKFIBU-UHFFFAOYSA-N 0.000 description 1
- FTZHCSWBKHGIJM-UHFFFAOYSA-N n-[3-[8-(4-morpholin-4-ylanilino)imidazo[1,2-a]pyrazin-6-yl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC(C=2N=C(NC=3C=CC(=CC=3)N3CCOCC3)C3=NC=CN3C=2)=C1 FTZHCSWBKHGIJM-UHFFFAOYSA-N 0.000 description 1
- UFPNMRFGNLHSOR-UHFFFAOYSA-N n-[3-ethoxy-4-(4-ethylpiperazin-1-yl)phenyl]-6-(1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-amine Chemical compound CCOC1=CC(NC=2C3=NC=CN3C=C(N=2)C=2C=C3NN=CC3=CC=2)=CC=C1N1CCN(CC)CC1 UFPNMRFGNLHSOR-UHFFFAOYSA-N 0.000 description 1
- GPKZWGGNVQVYHH-UHFFFAOYSA-N n-[4-(3-amino-3-methylazetidin-1-yl)phenyl]-6-(1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-amine Chemical compound C1C(C)(N)CN1C(C=C1)=CC=C1NC1=NC(C=2C=C3NN=CC3=CC=2)=CN2C1=NC=C2 GPKZWGGNVQVYHH-UHFFFAOYSA-N 0.000 description 1
- QIBGSKGSBOWEKZ-UHFFFAOYSA-N n-[4-[8-(3,4-dimethoxyanilino)imidazo[1,2-a]pyrazin-6-yl]phenyl]acetamide Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC(C=2C=CC(NC(C)=O)=CC=2)=CN2C1=NC=C2 QIBGSKGSBOWEKZ-UHFFFAOYSA-N 0.000 description 1
- HTVNDDLGKOBXOV-UHFFFAOYSA-N n-[4-[8-(4-morpholin-4-ylanilino)imidazo[1,2-a]pyrazin-6-yl]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C(N=C1NC=2C=CC(=CC=2)N2CCOCC2)=CN2C1=NC=C2 HTVNDDLGKOBXOV-UHFFFAOYSA-N 0.000 description 1
- DCXOETLCCJKPNX-UHFFFAOYSA-N n-[5-[8-(4-morpholin-4-ylanilino)imidazo[1,2-a]pyrazin-6-yl]pyridin-3-yl]acetamide Chemical compound CC(=O)NC1=CN=CC(C=2N=C(NC=3C=CC(=CC=3)N3CCOCC3)C3=NC=CN3C=2)=C1 DCXOETLCCJKPNX-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229960002009 naproxen Drugs 0.000 description 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 description 1
- 229960003940 naproxen sodium Drugs 0.000 description 1
- CDBRNDSHEYLDJV-FVGYRXGTSA-M naproxen sodium Chemical compound [Na+].C1=C([C@H](C)C([O-])=O)C=CC2=CC(OC)=CC=C21 CDBRNDSHEYLDJV-FVGYRXGTSA-M 0.000 description 1
- 210000000822 natural killer cell Anatomy 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 201000008383 nephritis Diseases 0.000 description 1
- 102000037979 non-receptor tyrosine kinases Human genes 0.000 description 1
- 108091008046 non-receptor tyrosine kinases Proteins 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical group C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 230000000414 obstructive effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- OFPXSFXSNFPTHF-UHFFFAOYSA-N oxaprozin Chemical compound O1C(CCC(=O)O)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 OFPXSFXSNFPTHF-UHFFFAOYSA-N 0.000 description 1
- 229960002739 oxaprozin Drugs 0.000 description 1
- 125000005968 oxazolinyl group Chemical group 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 229950003203 pexelizumab Drugs 0.000 description 1
- 239000002831 pharmacologic agent Substances 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 description 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 description 1
- 229960002702 piroxicam Drugs 0.000 description 1
- 210000004180 plasmocyte Anatomy 0.000 description 1
- 239000008389 polyethoxylated castor oil Substances 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229960005205 prednisolone Drugs 0.000 description 1
- OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 1
- JDOZJEUDSLGTLU-VWUMJDOOSA-N prednisolone phosphate Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)COP(O)(O)=O)[C@@H]4[C@@H]3CCC2=C1 JDOZJEUDSLGTLU-VWUMJDOOSA-N 0.000 description 1
- 229960002943 prednisolone sodium phosphate Drugs 0.000 description 1
- 229960004618 prednisone Drugs 0.000 description 1
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 1
- 210000001948 pro-b lymphocyte Anatomy 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 125000006238 prop-1-en-1-yl group Chemical group [H]\C(*)=C(/[H])C([H])([H])[H] 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 239000002599 prostaglandin synthase inhibitor Substances 0.000 description 1
- 125000004944 pyrazin-3-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- CZAAKPFIWJXPQT-UHFFFAOYSA-N quinazolin-2-amine Chemical compound C1=CC=CC2=NC(N)=NC=C21 CZAAKPFIWJXPQT-UHFFFAOYSA-N 0.000 description 1
- 125000004550 quinolin-6-yl group Chemical group N1=CC=CC2=CC(=CC=C12)* 0.000 description 1
- 230000003439 radiotherapeutic effect Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000008521 reorganization Effects 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 108091008020 response regulators Proteins 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 230000036303 septic shock Effects 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 201000009890 sinusitis Diseases 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- 229960001315 sodium aurothiomalate Drugs 0.000 description 1
- 229960004025 sodium salicylate Drugs 0.000 description 1
- JGMJQSFLQWGYMQ-UHFFFAOYSA-M sodium;2,6-dichloro-n-phenylaniline;acetate Chemical compound [Na+].CC([O-])=O.ClC1=CC=CC(Cl)=C1NC1=CC=CC=C1 JGMJQSFLQWGYMQ-UHFFFAOYSA-M 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000012289 standard assay Methods 0.000 description 1
- 210000000130 stem cell Anatomy 0.000 description 1
- 125000005338 substituted cycloalkoxy group Chemical group 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- MLKXDPUZXIRXEP-MFOYZWKCSA-N sulindac Chemical compound CC1=C(CC(O)=O)C2=CC(F)=CC=C2\C1=C/C1=CC=C(S(C)=O)C=C1 MLKXDPUZXIRXEP-MFOYZWKCSA-N 0.000 description 1
- 229960000894 sulindac Drugs 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 208000037707 susceptibility to 8 restless legs syndrome Diseases 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 229960001967 tacrolimus Drugs 0.000 description 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 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- 230000003582 thrombocytopenic effect Effects 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 229960000303 topotecan Drugs 0.000 description 1
- UCFGDBYHRUNTLO-QHCPKHFHSA-N topotecan Chemical compound C1=C(O)C(CN(C)C)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 UCFGDBYHRUNTLO-QHCPKHFHSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 102000003298 tumor necrosis factor receptor Human genes 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 229940121358 tyrosine kinase inhibitor Drugs 0.000 description 1
- 239000005483 tyrosine kinase inhibitor Substances 0.000 description 1
- 241000701447 unidentified baculovirus Species 0.000 description 1
- LNPDTQAFDNKSHK-UHFFFAOYSA-N valdecoxib Chemical compound CC=1ON=C(C=2C=CC=CC=2)C=1C1=CC=C(S(N)(=O)=O)C=C1 LNPDTQAFDNKSHK-UHFFFAOYSA-N 0.000 description 1
- 229960002004 valdecoxib Drugs 0.000 description 1
- 229960003048 vinblastine Drugs 0.000 description 1
- JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000001262 western blot Methods 0.000 description 1
- 239000012224 working solution Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
- 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
- A61K31/498—Pyrazines or piperazines ortho- and peri-condensed with carbocyclic ring systems, e.g. quinoxaline, phenazine
-
- 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
-
- 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
- A61P11/02—Nasal agents, e.g. decongestants
-
- 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
-
- 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
- A61P11/08—Bronchodilators
-
- 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
- A61P11/16—Central respiratory analeptics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- 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
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- 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
-
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- 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
-
- 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
- A61P37/02—Immunomodulators
-
- 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
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- 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
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
- C07D491/107—Spiro-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
- C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
- C12Q1/02—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving viable microorganisms
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
- C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
- C12Q1/48—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving transferase
- C12Q1/485—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving transferase involving kinase
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/53—Immunoassay; Biospecific binding assay; Materials therefor
- G01N33/573—Immunoassay; Biospecific binding assay; Materials therefor for enzymes or isoenzymes
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N2333/00—Assays involving biological materials from specific organisms or of a specific nature
- G01N2333/90—Enzymes; Proenzymes
- G01N2333/91—Transferases (2.)
- G01N2333/912—Transferases (2.) transferring phosphorus containing groups, e.g. kinases (2.7)
- G01N2333/91205—Phosphotransferases in general
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Immunology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Molecular Biology (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Pulmonology (AREA)
- Biochemistry (AREA)
- Physics & Mathematics (AREA)
- Microbiology (AREA)
- Biotechnology (AREA)
- Analytical Chemistry (AREA)
- Biomedical Technology (AREA)
- Hematology (AREA)
- Urology & Nephrology (AREA)
- General Engineering & Computer Science (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- Epidemiology (AREA)
- Pathology (AREA)
- Cell Biology (AREA)
- General Physics & Mathematics (AREA)
- Food Science & Technology (AREA)
- Rheumatology (AREA)
- Transplantation (AREA)
- Otolaryngology (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12058708P | 2008-12-08 | 2008-12-08 | |
| US14051408P | 2008-12-23 | 2008-12-23 | |
| US24097909P | 2009-09-09 | 2009-09-09 | |
| PCT/US2009/006445 WO2010068257A1 (en) | 2008-12-08 | 2009-12-07 | Imidazopyrazine syk inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA201190042A1 EA201190042A1 (ru) | 2012-02-28 |
| EA020461B1 true EA020461B1 (ru) | 2014-11-28 |
Family
ID=42242994
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA201190042A EA020461B1 (ru) | 2008-12-08 | 2009-12-07 | ИМИДАЗОПИРАЗИНОВЫЕ ИНГИБИТОРЫ Syk |
| EA201400197A EA024140B1 (ru) | 2008-12-08 | 2009-12-07 | Имидазопиразиновые ингибиторы тирозинкиназы syk |
| EA201690111A EA201690111A1 (ru) | 2008-12-08 | 2009-12-07 | Имидазопиразиновые ингибиторы тирозинкиназы syk |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA201400197A EA024140B1 (ru) | 2008-12-08 | 2009-12-07 | Имидазопиразиновые ингибиторы тирозинкиназы syk |
| EA201690111A EA201690111A1 (ru) | 2008-12-08 | 2009-12-07 | Имидазопиразиновые ингибиторы тирозинкиназы syk |
Country Status (30)
| Country | Link |
|---|---|
| US (7) | US8455493B2 (enExample) |
| EP (3) | EP2373169B1 (enExample) |
| JP (4) | JP5567587B2 (enExample) |
| KR (4) | KR20170013414A (enExample) |
| CN (2) | CN104744476B (enExample) |
| AU (1) | AU2009325132B2 (enExample) |
| BR (1) | BRPI0922225B1 (enExample) |
| CA (1) | CA2746023C (enExample) |
| CL (1) | CL2011001360A1 (enExample) |
| CO (1) | CO6390078A2 (enExample) |
| CY (1) | CY1118377T1 (enExample) |
| DK (1) | DK2716157T3 (enExample) |
| EA (3) | EA020461B1 (enExample) |
| ES (2) | ES2545610T3 (enExample) |
| HR (1) | HRP20161036T1 (enExample) |
| HU (1) | HUE030427T2 (enExample) |
| IL (3) | IL213365A (enExample) |
| LT (1) | LT2716157T (enExample) |
| MX (1) | MX2011006091A (enExample) |
| NZ (1) | NZ593459A (enExample) |
| PE (2) | PE20140975A1 (enExample) |
| PL (2) | PL2373169T3 (enExample) |
| PT (2) | PT2716157T (enExample) |
| RS (1) | RS55055B1 (enExample) |
| SG (1) | SG171991A1 (enExample) |
| SI (2) | SI2373169T1 (enExample) |
| SM (1) | SMT201600267B (enExample) |
| TW (2) | TWI478922B (enExample) |
| VN (1) | VN28228A1 (enExample) |
| WO (1) | WO2010068257A1 (enExample) |
Families Citing this family (67)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5496915B2 (ja) | 2008-02-13 | 2014-05-21 | シージーアイ ファーマシューティカルズ,インコーポレーテッド | 6−アリール−イミダゾ[1,2−a]ピラジン誘導体、その製造方法、及びその使用方法 |
| EA020461B1 (ru) | 2008-12-08 | 2014-11-28 | Джилид Коннектикут, Инк. | ИМИДАЗОПИРАЗИНОВЫЕ ИНГИБИТОРЫ Syk |
| PE20120121A1 (es) | 2008-12-08 | 2012-02-20 | Gilead Connecticut Inc | Derivados de imidazopirazina como inhibidores de syk |
| US8450321B2 (en) | 2008-12-08 | 2013-05-28 | Gilead Connecticut, Inc. | 6-(1H-indazol-6-yl)-N-[4-(morpholin-4-yl)phenyl]imidazo-[1,2-A]pyrazin-8-amine, or a pharmaceutically acceptable salt thereof, as a SYK inhibitor |
| UA111579C2 (uk) * | 2009-08-17 | 2016-05-25 | Інтеллікіне Ллк | ГЕТЕРОЦИКЛІЧНІ ПОХІДНІ 2-АМІНОБЕНЗО[d]ОКСАЗОЛУ, ФАРМАЦЕВТИЧНА КОМПОЗИЦІЯ НА ЇХ ОСНОВІ ТА ЇХ ЗАСТОСУВАННЯ ДЛЯ ЛІКУВАННЯ ЗАХВОРЮВАННЯ, ПОВ'АНОГО З РІ3-КІНАЗОЮ |
| JP5938352B2 (ja) | 2010-03-11 | 2016-06-22 | ギリアード コネチカット, インコーポレイテッド | イミダゾピリジンsyk阻害剤 |
| WO2012116237A2 (en) | 2011-02-23 | 2012-08-30 | Intellikine, Llc | Heterocyclic compounds and uses thereof |
| CA2834062A1 (en) | 2011-05-10 | 2012-11-15 | Merck Sharp & Dohme Corp. | Pyridyl aminopyridines as syk inhibitors |
| AU2012253885A1 (en) | 2011-05-10 | 2013-10-31 | Merck Sharp & Dohme Corp. | Aminopyrimidines as Syk inhibitors |
| WO2012154518A1 (en) | 2011-05-10 | 2012-11-15 | Merck Sharp & Dohme Corp. | Bipyridylaminopyridines as syk inhibitors |
| WO2013052391A1 (en) | 2011-10-05 | 2013-04-11 | Merck Sharp & Dohme Corp. | PHENYL CARBOXAMIDE-CONTAINING SPLEEN TYROSINE KINASE (Syk) INHIBITORS |
| US8987456B2 (en) | 2011-10-05 | 2015-03-24 | Merck Sharp & Dohme Corp. | 3-pyridyl carboxamide-containing spleen tyrosine kinase (SYK) inhibitors |
| EP2763976B1 (en) | 2011-10-05 | 2016-05-18 | Merck Sharp & Dohme Corp. | 2-pyridyl carboxamide-containing spleen tyrosine kinase (syk) inhibitors |
| AR090650A1 (es) | 2012-04-12 | 2014-11-26 | Alcon Res Ltd | Tratamiento para respuestas inflamatorias inducidas por microbios en el ojo |
| WO2013188856A1 (en) * | 2012-06-14 | 2013-12-19 | Gilead Connecticut, Inc. | Imidazopyrazine syk inhibitors |
| WO2013192125A1 (en) | 2012-06-20 | 2013-12-27 | Merck Sharp & Dohme Corp. | Pyrazolyl derivatives as syk inhibitors |
| EP2863913B1 (en) | 2012-06-20 | 2018-09-12 | Merck Sharp & Dohme Corp. | Imidazolyl analogs as syk inhibitors |
| WO2013192088A1 (en) | 2012-06-22 | 2013-12-27 | Merck Sharp & Dohme Corp. | SUBSTITUTED DIAZINE AND TRIAZINE SPLEEN TYROSINE KINASE (Syk) INHIBITORS |
| US9376418B2 (en) | 2012-06-22 | 2016-06-28 | Merck Sharp & Dohme Corp. | Substituted pyridine spleen tyrosine kinase (SYK) inhibitors |
| AU2013302617A1 (en) * | 2012-08-14 | 2015-02-05 | Gilead Calistoga Llc | Combination therapies for treating cancer |
| EP2884982B1 (en) | 2012-08-20 | 2017-09-20 | Merck Sharp & Dohme Corp. | SUBSTITUTED PHENYL SPLEEN TYROSINE KINASE (Syk) INHIBITORS |
| WO2014048065A1 (en) | 2012-09-28 | 2014-04-03 | Merck Sharp & Dohme Corp. | Triazolyl derivatives as syk inhibitors |
| EP2931281B1 (en) | 2012-12-12 | 2018-01-17 | Merck Sharp & Dohme Corp. | Amino-pyrimidine-containing spleen tyrosine kinase inhibitors |
| EP2934525B1 (en) | 2012-12-21 | 2019-05-08 | Merck Sharp & Dohme Corp. | Thiazole-substituted aminopyridines as spleen tyrosine kinase inhibitors |
| WO2014176216A1 (en) | 2013-04-26 | 2014-10-30 | Merck Sharp & Dohme Corp. | Thiazole-substituted aminopyrimidines as spleen tyrosine kinase inhibitors |
| EP2988744A4 (en) | 2013-04-26 | 2016-11-02 | Merck Sharp & Dohme | THIAZOLSUBSTITUTED AMINOHETEROARYLE AS MILZTYROSINKINASE INHIBITOR |
| PL3027171T3 (pl) | 2013-07-30 | 2020-08-24 | Gilead Connecticut, Inc. | Formulacja inhibitorów syk |
| EA029281B1 (ru) * | 2013-07-30 | 2018-03-30 | Джилид Коннектикут, Инк. | Полиморф ингибиторов syk |
| EA031601B1 (ru) | 2013-07-31 | 2019-01-31 | Джилид Сайэнс, Инк. | Ингибиторы syk |
| AU2014360537B2 (en) | 2013-12-04 | 2017-09-07 | Gilead Sciences, Inc. | Methods for treating cancers |
| WO2015094997A1 (en) | 2013-12-20 | 2015-06-25 | Merck Sharp & Dohme Corp. | Thiazole-substituted aminoheteroaryls as spleen tyrosine kinase inhibitors |
| US9670196B2 (en) | 2013-12-20 | 2017-06-06 | Merck Sharp & Dohme Corp. | Thiazole-substituted aminoheteroaryls as Spleen Tyrosine Kinase inhibitors |
| EP3083559B1 (en) | 2013-12-20 | 2021-03-10 | Merck Sharp & Dohme Corp. | Thiazole-substituted aminoheteroaryls as spleen tyrosine kinase inhibitors |
| US9290505B2 (en) | 2013-12-23 | 2016-03-22 | Gilead Sciences, Inc. | Substituted imidazo[1,2-a]pyrazines as Syk inhibitors |
| TWI662037B (zh) * | 2013-12-23 | 2019-06-11 | 美商基利科學股份有限公司 | 脾酪胺酸激酶抑制劑 |
| WO2015138273A1 (en) | 2014-03-13 | 2015-09-17 | Merck Sharp & Dohme Corp. | 2-pyrazine carboxamides as spleen tyrosine kinase inhibitors |
| US9796733B2 (en) | 2014-06-04 | 2017-10-24 | Merck Sharp & Dohme Corp. | Imidazo-pyrazine derivatives useful as soluble guanylate cyclase activators |
| TW201617074A (zh) | 2014-07-14 | 2016-05-16 | 吉李德科學股份有限公司 | Syk(脾酪胺酸激酶)抑制劑 |
| CN106687139A (zh) | 2014-07-14 | 2017-05-17 | 吉利德科学公司 | 用于治疗癌症的组合 |
| TW201639573A (zh) * | 2015-02-03 | 2016-11-16 | 吉李德科學股份有限公司 | 有關治療癌症之合併治療 |
| HK1249054A1 (zh) | 2015-04-21 | 2018-10-26 | Kronos Bio, Inc. | 使用syk抑制剂对慢性移植物抗宿主病的治疗 |
| US20180201614A1 (en) * | 2015-05-12 | 2018-07-19 | Kalyra Pharmaceuticals, Inc. | Bicyclic compounds |
| CN107709336B (zh) * | 2015-06-12 | 2021-06-22 | 杭州英创医药科技有限公司 | 作为Syk抑制剂和/或Syk-HDAC双重抑制剂的杂环化合物 |
| US20170173034A1 (en) | 2015-12-17 | 2017-06-22 | Gilead Sciences, Inc. | Combination of a jak inhibitor and a syk inhibitor for treating cancers and inflammatory disorders |
| EP3490547A4 (en) * | 2016-07-28 | 2020-04-01 | QBiotics Pty Ltd | TREATMENT METHOD |
| TW201822764A (zh) | 2016-09-14 | 2018-07-01 | 美商基利科學股份有限公司 | Syk抑制劑 |
| EP3512519A1 (en) | 2016-09-14 | 2019-07-24 | Gilead Sciences, Inc. | Syk inhibitors |
| WO2018108083A1 (zh) * | 2016-12-12 | 2018-06-21 | 杭州英创医药科技有限公司 | 作为Syk抑制剂和/或Syk-HDAC双重抑制剂的杂环化合物 |
| WO2018195471A1 (en) | 2017-04-21 | 2018-10-25 | Gilead Sciences, Inc. | Syk inhibitors in combination with hypomethylating agents |
| EP3670500A4 (en) * | 2017-08-18 | 2020-12-16 | Beijing Hanmi Pharmaceutical Co., Ltd. | CHEMICAL COMPOUND, PHARMACEUTICAL COMPOSITION OF IT, CORRESPONDING USE AND APPLICATION |
| KR20220070056A (ko) | 2017-08-25 | 2022-05-27 | 길리애드 사이언시즈, 인코포레이티드 | Syk 억제제의 다형체 |
| AU2018350683A1 (en) | 2017-10-19 | 2020-04-02 | Bayer Animal Health Gmbh | Use of fused heteroaromatic pyrrolidones for treatment and prevention of diseases in animals |
| CN109879878A (zh) * | 2017-12-06 | 2019-06-14 | 朱允涛 | 一种氘代的咪唑并吡嗪类脾酪氨酸激酶(Syk)抑制剂 |
| US12012394B2 (en) | 2018-02-19 | 2024-06-18 | Washington University | Alpha-synuclein ligands |
| EP3801069A4 (en) | 2018-06-01 | 2022-03-16 | Cornell University | COMBINATION THERAPY FOR A PI3K-ASSOCIATED DISEASE OR DISORDER |
| AU2020225455A1 (en) | 2019-02-22 | 2021-09-09 | Kronos Bio, Inc. | Solid forms of condensed pyrazines as Syk inhibitors |
| CA3129665A1 (en) | 2019-03-21 | 2020-09-24 | Onxeo | A dbait molecule in combination with kinase inhibitor for the treatment of cancer |
| KR20220098759A (ko) | 2019-11-08 | 2022-07-12 | 인쎄름 (엥스띠뛰 나씨오날 드 라 쌍떼 에 드 라 흐쉐르슈 메디깔) | 키나제 억제제에 대해 내성을 획득한 암의 치료 방법 |
| WO2021148581A1 (en) | 2020-01-22 | 2021-07-29 | Onxeo | Novel dbait molecule and its use |
| JP7535600B2 (ja) * | 2020-06-01 | 2024-08-16 | ナンジン ルイジエ ファーマ シーオー.,エルティーディー. | 化合物および脾臓チロシンキナーゼ阻害剤としてのその使用 |
| WO2022064458A1 (en) | 2020-09-28 | 2022-03-31 | 1ST Biotherapeutics, Inc. | Indazoles as hematopoietic progenitor kinase 1 (hpk1) inhibitors and methods of using same |
| KR102560178B1 (ko) * | 2021-02-10 | 2023-07-27 | 재단법인 대구경북첨단의료산업진흥재단 | 이미다조[1,5-a]피라진 유도체 화합물 및 이를 유효성분으로 함유하는 암 또는 자가면역질환의 예방 또는 치료용 약학적 조성물 |
| CN113480543B (zh) * | 2021-07-07 | 2022-05-17 | 无锡市第二人民医院 | 2,6,8-多取代咪唑并[1,2-a]吡嗪及其合成方法和应用 |
| KR20250004665A (ko) * | 2022-03-14 | 2025-01-08 | 퍼듀 리서치 파운데이션 | 비장 티로신 키나아제 억제제, 조성물 및 사용 방법 |
| EP4499643A4 (en) * | 2022-03-25 | 2026-01-28 | 1St Biotherapeutics Inc | INDAZOLES USED AS HEMATOPOIETIC PROGENITOR KINASE 1 (HPK1) INHIBITORS AND THEIR METHODS OF USE |
| CN119630668A (zh) * | 2022-07-25 | 2025-03-14 | 细胞基因公司 | 取代的咪唑并吡嗪化合物作为irak3结合剂 |
| WO2024102970A1 (en) * | 2022-11-11 | 2024-05-16 | Kronos Bio, Inc. | Compounds for modulating syk activity and e3 ubiquitin ligase activity |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005047290A2 (en) * | 2003-11-11 | 2005-05-26 | Cellular Genomics Inc. | Imidazo[1,2-a] pyrazin-8-ylamines as kinase inhibitors |
Family Cites Families (75)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2607813B1 (fr) | 1986-12-05 | 1989-03-31 | Montpellier I Universite | Alkylamino-8 imidazo (1,2-a) pyrazines et derives, leur preparation et leur application en therapeutique |
| US5137876A (en) | 1990-10-12 | 1992-08-11 | Merck & Co., Inc. | Nucleoside antiviral and anti-inflammatory compounds and compositions and methods for using same |
| DE4327027A1 (de) * | 1993-02-15 | 1994-08-18 | Bayer Ag | Imidazoazine |
| DE4337611A1 (de) * | 1993-11-04 | 1995-05-11 | Boehringer Ingelheim Kg | Neue Benzoylguanidine, ihre Herstellung und ihre Verwendung in Arzneimitteln |
| DE4337609A1 (de) | 1993-11-04 | 1995-05-11 | Boehringer Ingelheim Kg | Neue Pyrazincarboxamidderivate, ihre Herstellung und ihre Verwendung in Arzneimitteln |
| FR2711993B1 (fr) | 1993-11-05 | 1995-12-01 | Rhone Poulenc Rorer Sa | Médicaments contenant des dérivés de 7H-imidazol[1,2-a]pyrazine-8-one, les nouveaux composés et leur préparation. |
| KR100477070B1 (ko) * | 1994-03-25 | 2006-04-21 | 이소테크니카 인코포레이티드 | 중수소화작용에의한의약품의효능강화법 |
| US6334997B1 (en) * | 1994-03-25 | 2002-01-01 | Isotechnika, Inc. | Method of using deuterated calcium channel blockers |
| FR2723373B1 (fr) | 1994-08-02 | 1996-09-13 | Rhone Poulenc Rorer Sa | Forme purifiee de streptogramines, sa preparation et les compositions pharmaceutiques qui la contiennent |
| AU5348396A (en) | 1995-05-01 | 1996-11-21 | Fujisawa Pharmaceutical Co., Ltd. | Imidazo 1,2-a pyridine and imidazo 1,2-a pyridezine derivati ves and their use as bone resorption inhibitors |
| US5593997A (en) * | 1995-05-23 | 1997-01-14 | Pfizer Inc. | 4-aminopyrazolo(3-,4-D)pyrimidine and 4-aminopyrazolo-(3,4-D)pyridine tyrosine kinase inhibitors |
| US6249495B1 (en) | 1997-02-27 | 2001-06-19 | Matsushita Electric Industrial Co., Ltd. | Stepping motor control method and disk drive apparatus |
| SE9704404D0 (sv) | 1997-11-28 | 1997-11-28 | Astra Ab | New compounds |
| DE19948434A1 (de) | 1999-10-08 | 2001-06-07 | Gruenenthal Gmbh | Substanzbibliothek enthaltend bicyclische Imidazo-5-amine und/oder bicyclische Imidazo-3-amine |
| JP2001302667A (ja) * | 2000-04-28 | 2001-10-31 | Bayer Ag | イミダゾピリミジン誘導体およびトリアゾロピリミジン誘導体 |
| WO2001098685A1 (en) | 2000-06-19 | 2001-12-27 | Tay Armin S | Axial position changing transmission mechanism |
| GB0018473D0 (en) | 2000-07-27 | 2000-09-13 | Merck Sharp & Dohme | Therapeutic agents |
| DE10050663A1 (de) | 2000-10-13 | 2002-04-18 | Gruenenthal Gmbh | Verwendung von substituierten Imidazo[1,2-a]pyridin-, -pyrimidin- und pyrazin-3-yl-amin-Derivaten zur Herstellung von Medikamenten zur NOS-Inhibierung |
| WO2002101221A2 (en) | 2000-11-20 | 2002-12-19 | Cryoco, Inc. | A method and apparatus for the preparation and usage of a cryogenic propellant or explosive system |
| DK174233B1 (da) | 2000-12-27 | 2002-10-07 | Dss Danish Separation Systems | Sanitært spiralfilteranlæg |
| WO2002060492A1 (en) * | 2001-01-30 | 2002-08-08 | Cytopia Pty Ltd | Methods of inhibiting kinases |
| GB0103926D0 (en) | 2001-02-17 | 2001-04-04 | Astrazeneca Ab | Chemical compounds |
| WO2002076985A1 (en) | 2001-03-23 | 2002-10-03 | Smithkline Beecham Corporation | Compounds useful as kinase inhibitors for the treatment of hyperproliferative diseases |
| US7003125B2 (en) | 2001-09-12 | 2006-02-21 | Seung-Hwan Yi | Micromachined piezoelectric microspeaker and fabricating method thereof |
| JP2005523288A (ja) | 2002-02-19 | 2005-08-04 | ファルマシア・アンド・アップジョン・カンパニー・エルエルシー | 疾病治療用の縮合した二環式−n−架橋−複素環式芳香族カルボキサミド |
| BR0309398A (pt) | 2002-04-19 | 2005-02-01 | Cellular Genomics Inc | Composto ou um seu sal, hidrato, solvato, forma cristalina, diastereÈmero, prodroga farmaceuticamente aceitável, ou misturas deles, composição farmacêutica, e, métodos para tratar uma condição envolvida com a cinase em um mamìfero, para tratar câncer, e para identificar uma cinase |
| US20040072081A1 (en) | 2002-05-14 | 2004-04-15 | Coleman Thomas P. | Methods for etching photolithographic reticles |
| US7288075B2 (en) | 2002-06-27 | 2007-10-30 | Ethicon, Inc. | Methods and devices utilizing rheological materials |
| JP2004053714A (ja) | 2002-07-17 | 2004-02-19 | Fuji Xerox Co Ltd | 画像定着装置及び画像定着方法 |
| US20040026867A1 (en) | 2002-08-09 | 2004-02-12 | Adams David J. | Bearing seal |
| US6761361B2 (en) | 2002-08-09 | 2004-07-13 | Credo Technology Corporation | Drill and drive apparatus with improved tool holder |
| AU2003270489A1 (en) | 2002-09-09 | 2004-03-29 | Cellular Genomics, Inc. | 6-ARYL-IMIDAZO(1,2-a)PYRAZIN-8-YLAMINES, METHOD OF MAKING, AND METHOD OF USE THEREOF |
| WO2004026867A2 (en) | 2002-09-19 | 2004-04-01 | Schering Corporation | Imidazopyridines as cyclin dependent kinase inhibitors |
| JP4799864B2 (ja) * | 2002-09-23 | 2011-10-26 | シェーリング コーポレイション | サイクリン依存性キナーゼインヒビターとしてのイミダゾピラジン |
| KR20060010709A (ko) | 2002-09-23 | 2006-02-02 | 쉐링 코포레이션 | 사이클린 의존성 키나제 억제제로서의 신규한 이미다조피라진 |
| JP4056346B2 (ja) | 2002-09-30 | 2008-03-05 | 三洋電機株式会社 | 非水電解質二次電池 |
| AU2003304204B2 (en) | 2002-10-29 | 2009-12-24 | Insmed Incorporated | Sustained release of antiinfectives |
| US7189723B2 (en) * | 2003-02-10 | 2007-03-13 | Cgi Pharmaceuticals, Inc. | Certain 8-heteroaryl-6-phenyl-imidazo[1,2-a]pyrazines as modulators of kinase activity |
| AR043002A1 (es) * | 2003-02-18 | 2005-07-13 | Altana Pharma Ag | Imidazopirazinas 6-substituidos |
| US7186832B2 (en) * | 2003-02-20 | 2007-03-06 | Sugen Inc. | Use of 8-amino-aryl-substituted imidazopyrazines as kinase inhibitors |
| US7157460B2 (en) * | 2003-02-20 | 2007-01-02 | Sugen Inc. | Use of 8-amino-aryl-substituted imidazopyrazines as kinase inhibitors |
| US7456393B2 (en) | 2003-04-10 | 2008-11-25 | Ge Homeland Protection, Inc. | Device for testing surfaces of articles for traces of explosives and/or drugs |
| US7405295B2 (en) * | 2003-06-04 | 2008-07-29 | Cgi Pharmaceuticals, Inc. | Certain imidazo[1,2-a]pyrazin-8-ylamines and method of inhibition of Bruton's tyrosine kinase by such compounds |
| US20060183746A1 (en) * | 2003-06-04 | 2006-08-17 | Currie Kevin S | Certain imidazo[1,2-a]pyrazin-8-ylamines and method of inhibition of Bruton's tyrosine kinase by such compounds |
| US7393848B2 (en) * | 2003-06-30 | 2008-07-01 | Cgi Pharmaceuticals, Inc. | Certain heterocyclic substituted imidazo[1,2-A]pyrazin-8-ylamines and methods of inhibition of Bruton's tyrosine kinase by such compounds |
| WO2005019220A2 (en) | 2003-08-11 | 2005-03-03 | Cellular Genomics Inc. | Substituted imidazo[1,2-a]pyrazines as modulators of kinase activity |
| US7236749B2 (en) | 2003-10-15 | 2007-06-26 | Honeywell International Inc. | Stuck microphone deselection system and method |
| WO2005085252A1 (en) * | 2004-03-04 | 2005-09-15 | Biofocus Discovery Limited | Imidazo ‘1,2-a’ pyrazine compounds which interact with protein kinases |
| JP2006099930A (ja) | 2004-09-01 | 2006-04-13 | Tdk Corp | 情報記録媒体、記録再生装置およびスタンパー |
| US8145601B2 (en) | 2004-09-09 | 2012-03-27 | Microsoft Corporation | Method, system, and apparatus for providing resilient data transfer in a data protection system |
| EP1812439B2 (en) | 2004-10-15 | 2017-12-06 | Takeda Pharmaceutical Company Limited | Kinase inhibitors |
| CN101124227A (zh) * | 2004-11-10 | 2008-02-13 | Cgi制药有限公司 | 可用作激酶活性调节剂的咪唑并[1,2-a]吡嗪-8-基胺 |
| JP2008519843A (ja) * | 2004-11-10 | 2008-06-12 | シージーアイ ファーマスーティカル インコーポレーテッド | 特定のイミダゾ[1,2−a]ビラジン−8−イラミンズ、その生成方法及びそれに関する使用方法 |
| JP4883959B2 (ja) | 2005-08-17 | 2012-02-22 | Ntn株式会社 | 回転検出装置および回転検出装置付き軸受 |
| GB0520838D0 (en) * | 2005-10-13 | 2005-11-23 | Glaxo Group Ltd | Novel compounds |
| EP1945644A2 (en) * | 2005-11-10 | 2008-07-23 | Schering Corporation | Imidazopyrazines as protein kinase inhibitors |
| JP4837378B2 (ja) | 2006-01-04 | 2011-12-14 | 株式会社日立製作所 | データの改竄を防止する記憶装置 |
| US7446352B2 (en) | 2006-03-09 | 2008-11-04 | Tela Innovations, Inc. | Dynamic array architecture |
| DE102006032495A1 (de) | 2006-07-13 | 2008-02-07 | Nokia Siemens Networks Gmbh & Co.Kg | Verfahren und Vorrichtung zur Vermeidung von Interferenzen in einem zellulären Funkkommunikationssystem |
| US20080025821A1 (en) | 2006-07-25 | 2008-01-31 | Applied Materials, Inc. | Octagon transfer chamber |
| JP5336375B2 (ja) | 2006-08-30 | 2013-11-06 | セルゾーム リミテッド | キナーゼ阻害剤としてのトリアゾール誘導体 |
| ES2307402B1 (es) | 2006-10-30 | 2009-09-30 | Archivel Farma, S.L. | Vacuna profilactica contra la tuberculosis. |
| WO2008138843A1 (en) * | 2007-05-10 | 2008-11-20 | Galapagos N.V. | Imidazopyridines and triazolopyrimidines useful for the treatment of joint degenerative & inflammatory diseases |
| EP2229390B1 (en) | 2007-12-14 | 2014-04-09 | F. Hoffmann-La Roche AG | Novel imidazoý1,2-a¨pyridine and imidazoý1,2-b¨pyridazine derivatives |
| JP5496915B2 (ja) | 2008-02-13 | 2014-05-21 | シージーアイ ファーマシューティカルズ,インコーポレーテッド | 6−アリール−イミダゾ[1,2−a]ピラジン誘導体、その製造方法、及びその使用方法 |
| CA2723237A1 (en) * | 2008-05-06 | 2009-11-12 | Peter A. Blomgren | Substituted amides, method of making, and use as btk inhibitors |
| CA2726460C (en) | 2008-07-15 | 2017-02-21 | F. Hoffmann-La Roche Ag | Novel phenyl-imidazopyridines and pyridazines |
| TWI453207B (zh) | 2008-09-08 | 2014-09-21 | Signal Pharm Llc | 胺基三唑并吡啶,其組合物及使用其之治療方法 |
| EA020461B1 (ru) | 2008-12-08 | 2014-11-28 | Джилид Коннектикут, Инк. | ИМИДАЗОПИРАЗИНОВЫЕ ИНГИБИТОРЫ Syk |
| US8450321B2 (en) * | 2008-12-08 | 2013-05-28 | Gilead Connecticut, Inc. | 6-(1H-indazol-6-yl)-N-[4-(morpholin-4-yl)phenyl]imidazo-[1,2-A]pyrazin-8-amine, or a pharmaceutically acceptable salt thereof, as a SYK inhibitor |
| PE20120121A1 (es) | 2008-12-08 | 2012-02-20 | Gilead Connecticut Inc | Derivados de imidazopirazina como inhibidores de syk |
| US20110112995A1 (en) | 2009-10-28 | 2011-05-12 | Industrial Technology Research Institute | Systems and methods for organizing collective social intelligence information using an organic object data model |
| JP5938352B2 (ja) | 2010-03-11 | 2016-06-22 | ギリアード コネチカット, インコーポレイテッド | イミダゾピリジンsyk阻害剤 |
| JP5554746B2 (ja) | 2011-05-06 | 2014-07-23 | 株式会社日立製作所 | ガス絶縁母線及びガス絶縁母線の異物除去方法 |
| US20140148430A1 (en) | 2012-11-26 | 2014-05-29 | Gilead Connecticut, Inc. | Imidazopyridines syk inhibitors |
-
2009
- 2009-12-07 EA EA201190042A patent/EA020461B1/ru active IP Right Revival
- 2009-12-07 KR KR1020177002329A patent/KR20170013414A/ko not_active Ceased
- 2009-12-07 LT LTEP13005979.3T patent/LT2716157T/lt unknown
- 2009-12-07 TW TW098141713A patent/TWI478922B/zh active
- 2009-12-07 CN CN201510093652.9A patent/CN104744476B/zh active Active
- 2009-12-07 EP EP20090832228 patent/EP2373169B1/en active Active
- 2009-12-07 ES ES09832228.2T patent/ES2545610T3/es active Active
- 2009-12-07 KR KR1020177014984A patent/KR20170066685A/ko not_active Ceased
- 2009-12-07 RS RS20160667A patent/RS55055B1/sr unknown
- 2009-12-07 NZ NZ593459A patent/NZ593459A/xx not_active IP Right Cessation
- 2009-12-07 EA EA201400197A patent/EA024140B1/ru active IP Right Revival
- 2009-12-07 TW TW103135973A patent/TWI529172B/zh active
- 2009-12-07 SI SI200931249T patent/SI2373169T1/sl unknown
- 2009-12-07 US US12/632,140 patent/US8455493B2/en active Active
- 2009-12-07 PL PL09832228T patent/PL2373169T3/pl unknown
- 2009-12-07 EP EP13005979.3A patent/EP2716157B1/en active Active
- 2009-12-07 PE PE2014000121A patent/PE20140975A1/es active IP Right Grant
- 2009-12-07 BR BRPI0922225-1A patent/BRPI0922225B1/pt not_active IP Right Cessation
- 2009-12-07 CN CN200980156331.1A patent/CN102307474B/zh active Active
- 2009-12-07 ES ES13005979.3T patent/ES2590804T3/es active Active
- 2009-12-07 KR KR1020117015724A patent/KR101745732B1/ko active Active
- 2009-12-07 WO PCT/US2009/006445 patent/WO2010068257A1/en not_active Ceased
- 2009-12-07 PT PT130059793T patent/PT2716157T/pt unknown
- 2009-12-07 KR KR1020147035525A patent/KR101748925B1/ko active Active
- 2009-12-07 SI SI200931503A patent/SI2716157T1/sl unknown
- 2009-12-07 AU AU2009325132A patent/AU2009325132B2/en not_active Ceased
- 2009-12-07 DK DK13005979.3T patent/DK2716157T3/en active
- 2009-12-07 PT PT98322282T patent/PT2373169E/pt unknown
- 2009-12-07 VN VN201101623A patent/VN28228A1/vi unknown
- 2009-12-07 PE PE2011001178A patent/PE20120058A1/es active IP Right Grant
- 2009-12-07 SG SG2011041241A patent/SG171991A1/en unknown
- 2009-12-07 JP JP2011539524A patent/JP5567587B2/ja active Active
- 2009-12-07 PL PL13005979T patent/PL2716157T3/pl unknown
- 2009-12-07 MX MX2011006091A patent/MX2011006091A/es active IP Right Grant
- 2009-12-07 HU HUE13005979A patent/HUE030427T2/en unknown
- 2009-12-07 EP EP16164453.9A patent/EP3123864A1/en not_active Withdrawn
- 2009-12-07 CA CA2746023A patent/CA2746023C/en not_active Expired - Fee Related
- 2009-12-07 EA EA201690111A patent/EA201690111A1/ru unknown
-
2011
- 2011-06-05 IL IL213365A patent/IL213365A/en not_active IP Right Cessation
- 2011-06-07 CL CL2011001360A patent/CL2011001360A1/es unknown
- 2011-06-21 CO CO11077863A patent/CO6390078A2/es active IP Right Grant
-
2013
- 2013-04-23 US US13/868,971 patent/US8748607B2/en not_active Expired - Fee Related
- 2013-04-23 US US13/868,967 patent/US8765761B2/en not_active Expired - Fee Related
-
2014
- 2014-05-07 JP JP2014095907A patent/JP5832586B2/ja not_active Expired - Fee Related
- 2014-05-09 US US14/274,618 patent/US9120811B2/en active Active
- 2014-06-09 US US14/300,189 patent/US9212191B2/en active Active
- 2014-08-27 IL IL234326A patent/IL234326A/en not_active IP Right Cessation
- 2014-11-23 IL IL235837A patent/IL235837A0/en unknown
-
2015
- 2015-08-12 JP JP2015159313A patent/JP6132445B2/ja active Active
- 2015-10-13 US US14/882,278 patent/US9796718B2/en active Active
-
2016
- 2016-08-05 SM SM201600267T patent/SMT201600267B/it unknown
- 2016-08-17 HR HRP20161036TT patent/HRP20161036T1/hr unknown
- 2016-08-18 CY CY20161100814T patent/CY1118377T1/el unknown
-
2017
- 2017-03-13 JP JP2017047354A patent/JP2017101090A/ja not_active Withdrawn
- 2017-09-28 US US15/719,399 patent/US20180086769A1/en not_active Abandoned
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005047290A2 (en) * | 2003-11-11 | 2005-05-26 | Cellular Genomics Inc. | Imidazo[1,2-a] pyrazin-8-ylamines as kinase inhibitors |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US9796718B2 (en) | 6-(benzo[d]thiazol-5-yl)-n-(3,4-dimethoxyphenyl)imidazo[1,2-a]pyrazin-8-amine | |
| US8450321B2 (en) | 6-(1H-indazol-6-yl)-N-[4-(morpholin-4-yl)phenyl]imidazo-[1,2-A]pyrazin-8-amine, or a pharmaceutically acceptable salt thereof, as a SYK inhibitor | |
| IL213369A (en) | Weight-based calibration system for pressure-sensitive catheters | |
| HK1233445A1 (en) | Imidazopyrazine syk inhibitors | |
| HK1211939B (en) | Imidazopyrazine syk inhibitors |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Lapse of a eurasian patent due to non-payment of renewal fees within the time limit in the following designated state(s) |
Designated state(s): AM AZ BY KZ KG MD TJ TM RU |
|
| NF4A | Restoration of lapsed right to a eurasian patent |
Designated state(s): AM AZ BY KZ KG MD TJ TM RU |