HRP20220599T1 - Heterociklički spojevi kao inhibitori pi3k-gama - Google Patents
Heterociklički spojevi kao inhibitori pi3k-gama Download PDFInfo
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- HRP20220599T1 HRP20220599T1 HRP20220599TT HRP20220599T HRP20220599T1 HR P20220599 T1 HRP20220599 T1 HR P20220599T1 HR P20220599T T HRP20220599T T HR P20220599TT HR P20220599 T HRP20220599 T HR P20220599T HR P20220599 T1 HRP20220599 T1 HR P20220599T1
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- HR
- Croatia
- Prior art keywords
- alkyl
- pyrazolo
- amino
- carboxamide
- pyrimidine
- Prior art date
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- 150000002391 heterocyclic compounds Chemical class 0.000 title 1
- 239000003112 inhibitor Substances 0.000 title 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 129
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 62
- 125000001424 substituent group Chemical group 0.000 claims 46
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 42
- 150000003839 salts Chemical class 0.000 claims 30
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 29
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 29
- 125000000217 alkyl group Chemical group 0.000 claims 29
- 150000001875 compounds Chemical class 0.000 claims 28
- 229910052736 halogen Inorganic materials 0.000 claims 28
- 150000002367 halogens Chemical class 0.000 claims 28
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 25
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 25
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 24
- 229910052799 carbon Inorganic materials 0.000 claims 21
- LPCQBTAOTIZGAE-UHFFFAOYSA-N 2h-pyrimidine-1-carboxamide Chemical compound NC(=O)N1CN=CC=C1 LPCQBTAOTIZGAE-UHFFFAOYSA-N 0.000 claims 20
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 19
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 16
- 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims 15
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 14
- 229910052739 hydrogen Inorganic materials 0.000 claims 14
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims 11
- 229910052757 nitrogen Inorganic materials 0.000 claims 11
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 10
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 9
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 8
- 206010021245 Idiopathic thrombocytopenic purpura Diseases 0.000 claims 8
- 208000031981 Thrombocytopenic Idiopathic Purpura Diseases 0.000 claims 8
- 201000003710 autoimmune thrombocytopenic purpura Diseases 0.000 claims 8
- 206010073478 Anaplastic large-cell lymphoma Diseases 0.000 claims 7
- 208000032004 Large-Cell Anaplastic Lymphoma Diseases 0.000 claims 7
- 125000004414 alkyl thio group Chemical group 0.000 claims 7
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 6
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 6
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 6
- 208000011691 Burkitt lymphomas Diseases 0.000 claims 6
- 206010012818 diffuse large B-cell lymphoma Diseases 0.000 claims 6
- -1 ethoxy, phenyl Chemical group 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 208000031671 Large B-Cell Diffuse Lymphoma Diseases 0.000 claims 5
- 206010047115 Vasculitis Diseases 0.000 claims 5
- 125000006568 (C4-C7) heterocycloalkyl group Chemical group 0.000 claims 4
- 206010025323 Lymphomas Diseases 0.000 claims 4
- 206010039491 Sarcoma Diseases 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 201000009020 malignant peripheral nerve sheath tumor Diseases 0.000 claims 4
- 208000029974 neurofibrosarcoma Diseases 0.000 claims 4
- 201000003076 Angiosarcoma Diseases 0.000 claims 3
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims 3
- 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims 3
- 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims 3
- 101150073096 NRAS gene Proteins 0.000 claims 3
- 206010028980 Neoplasm Diseases 0.000 claims 3
- 208000025317 T-cell and NK-cell neoplasm Diseases 0.000 claims 3
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 208000020968 mature T-cell and NK-cell non-Hodgkin lymphoma Diseases 0.000 claims 3
- 230000002093 peripheral effect Effects 0.000 claims 3
- XMRIUEGHBZTNND-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1=CC=NC2=C(C(=O)N)C=NN21 XMRIUEGHBZTNND-UHFFFAOYSA-N 0.000 claims 3
- AYVJBFMKMYFPSN-UHFFFAOYSA-N 2-amino-N-[1-[8-chloro-1-cyano-5-(1,1-dioxo-1,4-thiazinan-4-yl)imidazo[1,5-a]pyridin-6-yl]ethyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound NC1=NN2C(N=CC=C2)=C1C(=O)NC(C)C=1C=C(C=2N(C=1N1CCS(CC1)(=O)=O)C=NC=2C#N)Cl AYVJBFMKMYFPSN-UHFFFAOYSA-N 0.000 claims 2
- JUQFRGPVIULNNW-UHFFFAOYSA-N 2-amino-N-[1-[8-chloro-1-cyano-5-(2-methyl-1,1-dioxo-1,4-thiazinan-4-yl)imidazo[1,5-a]pyridin-6-yl]ethyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound NC1=NN2C(N=CC=C2)=C1C(=O)NC(C)C=1C=C(C=2N(C=1N1CC(S(CC1)(=O)=O)C)C=NC=2C#N)Cl JUQFRGPVIULNNW-UHFFFAOYSA-N 0.000 claims 2
- CRGGDZXHXINBKL-UHFFFAOYSA-N 2-amino-N-[1-[8-chloro-1-cyano-5-(2-methyl-1,1-dioxo-1,4-thiazinan-4-yl)imidazo[1,5-a]pyridin-6-yl]propyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound NC1=NN2C(N=CC=C2)=C1C(=O)NC(CC)C=1C=C(C=2N(C=1N1CC(S(CC1)(=O)=O)C)C=NC=2C#N)Cl CRGGDZXHXINBKL-UHFFFAOYSA-N 0.000 claims 2
- ZVVWUBOYIVQERS-UHFFFAOYSA-N 2-amino-N-[1-[8-chloro-5-(1,1-dioxo-1,4-thiazinan-4-yl)imidazo[1,5-a]pyridin-6-yl]propyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound NC1=NN2C(N=CC=C2)=C1C(=O)NC(CC)C=1C=C(C=2N(C=1N1CCS(CC1)(=O)=O)C=NC=2)Cl ZVVWUBOYIVQERS-UHFFFAOYSA-N 0.000 claims 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 2
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims 2
- 125000006519 CCH3 Chemical group 0.000 claims 2
- 208000001258 Hemangiosarcoma Diseases 0.000 claims 2
- 208000006404 Large Granular Lymphocytic Leukemia Diseases 0.000 claims 2
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims 2
- 208000031839 Peripheral nerve sheath tumour malignant Diseases 0.000 claims 2
- 208000007048 Polymyalgia Rheumatica Diseases 0.000 claims 2
- 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 claims 2
- 208000029052 T-cell acute lymphoblastic leukemia Diseases 0.000 claims 2
- 206010042971 T-cell lymphoma Diseases 0.000 claims 2
- 208000027585 T-cell non-Hodgkin lymphoma Diseases 0.000 claims 2
- 210000001744 T-lymphocyte Anatomy 0.000 claims 2
- 206010043540 Thromboangiitis obliterans Diseases 0.000 claims 2
- 206010052779 Transplant rejections Diseases 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 208000003455 anaphylaxis Diseases 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 210000001102 germinal center b cell Anatomy 0.000 claims 2
- 208000015446 immunoglobulin a vasculitis Diseases 0.000 claims 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 210000004698 lymphocyte Anatomy 0.000 claims 2
- 201000005962 mycosis fungoides Diseases 0.000 claims 2
- 230000002085 persistent effect Effects 0.000 claims 2
- 230000000306 recurrent effect Effects 0.000 claims 2
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 1
- BHFVRKLOPVLCCZ-UHFFFAOYSA-N 2-amino-N-[(1,8-dichloro-5-pyrrolidin-1-ylimidazo[1,5-a]pyridin-6-yl)methyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound NC1=NN2C(N=CC=C2)=C1C(=O)NCC=1C=C(C=2N(C=1N1CCCC1)C=NC=2Cl)Cl BHFVRKLOPVLCCZ-UHFFFAOYSA-N 0.000 claims 1
- UHHYRGYBZFDIQL-NSHDSACASA-N 2-amino-N-[(1S)-1-[1,8-dichloro-5-(1,1-dioxo-1,2,5-thiadiazepan-5-yl)imidazo[1,5-a]pyridin-6-yl]ethyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound NC1=NN2C(N=CC=C2)=C1C(=O)N[C@@H](C)C=1C=C(C=2N(C=1N1CCNS(CC1)(=O)=O)C=NC=2Cl)Cl UHHYRGYBZFDIQL-NSHDSACASA-N 0.000 claims 1
- QPFDYIBLUFFWEI-NSHDSACASA-N 2-amino-N-[(1S)-1-[1,8-dichloro-5-(5-oxo-1,4-diazepan-1-yl)imidazo[1,5-a]pyridin-6-yl]ethyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound NC1=NN2C(N=CC=C2)=C1C(=O)N[C@@H](C)C=1C=C(C=2N(C=1N1CCNC(CC1)=O)C=NC=2Cl)Cl QPFDYIBLUFFWEI-NSHDSACASA-N 0.000 claims 1
- BJZAGPURCJXEDF-NSHDSACASA-N 2-amino-N-[(1S)-1-[4-chloro-7-(1,1-dioxo-1,4-thiazinan-4-yl)-3-fluoropyrazolo[1,5-a]pyridin-6-yl]ethyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound NC1=NN2C(N=CC=C2)=C1C(=O)N[C@@H](C)C=1C=C(C=2N(C=1N1CCS(CC1)(=O)=O)N=CC=2F)Cl BJZAGPURCJXEDF-NSHDSACASA-N 0.000 claims 1
- CJVNEHFNIUFZJU-LBPRGKRZSA-N 2-amino-N-[(1S)-1-[4-chloro-7-(1,1-dioxo-1,4-thiazinan-4-yl)pyrazolo[1,5-a]pyridin-6-yl]ethyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound NC1=NN2C(N=CC=C2)=C1C(=O)N[C@@H](C)C=1C=C(C=2N(C=1N1CCS(CC1)(=O)=O)N=CC=2)Cl CJVNEHFNIUFZJU-LBPRGKRZSA-N 0.000 claims 1
- SWDLALMLXXPMCA-OLZOCXBDSA-N 2-amino-N-[(1S)-1-[8-chloro-5-[(2R)-2-methyl-1,1-dioxo-1,4-thiazinan-4-yl]imidazo[1,5-a]pyridin-6-yl]ethyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound NC1=NN2C(N=CC=C2)=C1C(=O)N[C@@H](C)C=1C=C(C=2N(C=1N1C[C@H](S(CC1)(=O)=O)C)C=NC=2)Cl SWDLALMLXXPMCA-OLZOCXBDSA-N 0.000 claims 1
- SWDLALMLXXPMCA-STQMWFEESA-N 2-amino-N-[(1S)-1-[8-chloro-5-[(2S)-2-methyl-1,1-dioxo-1,4-thiazinan-4-yl]imidazo[1,5-a]pyridin-6-yl]ethyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound NC1=NN2C(N=CC=C2)=C1C(=O)N[C@@H](C)C=1C=C(C=2N(C=1N1C[C@@H](S(CC1)(=O)=O)C)C=NC=2)Cl SWDLALMLXXPMCA-STQMWFEESA-N 0.000 claims 1
- WWEUWPZFOKJJSE-UHFFFAOYSA-N 2-amino-N-[(8-chloro-1-cyano-5-pyrrolidin-1-ylimidazo[1,5-a]pyridin-6-yl)methyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound NC1=NN2C(N=CC=C2)=C1C(=O)NCC=1C=C(C=2N(C=1N1CCCC1)C=NC=2C#N)Cl WWEUWPZFOKJJSE-UHFFFAOYSA-N 0.000 claims 1
- SHRZWRQJYOYRKJ-UHFFFAOYSA-N 2-amino-N-[(8-chloro-5-pyrrolidin-1-ylimidazo[1,5-a]pyridin-6-yl)methyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound NC1=NN2C(N=CC=C2)=C1C(=O)NCC=1C=C(C=2N(C=1N1CCCC1)C=NC=2)Cl SHRZWRQJYOYRKJ-UHFFFAOYSA-N 0.000 claims 1
- KLENJARMZRMDBE-UHFFFAOYSA-N 2-amino-N-[1-(1-benzyl-4-chloro-7-ethoxyindazol-6-yl)ethyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound NC1=NN2C(N=CC=C2)=C1C(=O)NC(C)C1=CC(=C2C=NN(C2=C1OCC)CC1=CC=CC=C1)Cl KLENJARMZRMDBE-UHFFFAOYSA-N 0.000 claims 1
- SIOSGODTYYDOMV-UHFFFAOYSA-N 2-amino-N-[1-(1-but-2-ynyl-4-chloro-7-ethoxyindazol-6-yl)ethyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound NC1=NN2C(N=CC=C2)=C1C(=O)NC(C)C1=CC(=C2C=NN(C2=C1OCC)CC#CC)Cl SIOSGODTYYDOMV-UHFFFAOYSA-N 0.000 claims 1
- BZKWGQLEUZZIQL-UHFFFAOYSA-N 2-amino-N-[1-(2-benzyl-4-chloro-7-ethoxyindazol-6-yl)ethyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound NC1=NN2C(N=CC=C2)=C1C(=O)NC(C)C=1C=C(C2=CN(N=C2C=1OCC)CC1=CC=CC=C1)Cl BZKWGQLEUZZIQL-UHFFFAOYSA-N 0.000 claims 1
- NGJGMWGNALEXKA-UHFFFAOYSA-N 2-amino-N-[1-(2-but-2-ynyl-4-chloro-7-ethoxyindazol-6-yl)ethyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound NC1=NN2C(N=CC=C2)=C1C(=O)NC(C)C=1C=C(C2=CN(N=C2C=1OCC)CC#CC)Cl NGJGMWGNALEXKA-UHFFFAOYSA-N 0.000 claims 1
- HLBJNHYXJGJLQA-UHFFFAOYSA-N 2-amino-N-[1-(3,4-dichloro-7-ethoxy-2H-indazol-6-yl)ethyl]-5-(5-methoxypyridin-3-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound NC1=NN2C(N=C(C=C2)C=2C=NC=C(C=2)OC)=C1C(=O)NC(C)C1=CC(=C2C(=NNC2=C1OCC)Cl)Cl HLBJNHYXJGJLQA-UHFFFAOYSA-N 0.000 claims 1
- WPFIFJVLISXCCG-UHFFFAOYSA-N 2-amino-N-[1-(3,4-dimethyl-7-phenyl-2H-indazol-6-yl)ethyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound NC1=NN2C(N=CC=C2)=C1C(=O)NC(C)C1=CC(=C2C(=NNC2=C1C1=CC=CC=C1)C)C WPFIFJVLISXCCG-UHFFFAOYSA-N 0.000 claims 1
- RMORGGRUYZLNKT-UHFFFAOYSA-N 2-amino-N-[1-(3-bromo-4-chloro-7-ethoxy-2H-indazol-6-yl)ethyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound NC1=NN2C(N=CC=C2)=C1C(=O)NC(C)C1=CC(=C2C(=NNC2=C1OCC)Br)Cl RMORGGRUYZLNKT-UHFFFAOYSA-N 0.000 claims 1
- IOEJDDVXHMWQID-UHFFFAOYSA-N 2-amino-N-[1-(3-bromo-4-chloro-7-phenyl-2H-indazol-6-yl)ethyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound NC1=NN2C(N=CC=C2)=C1C(=O)NC(C)C1=CC(=C2C(=NNC2=C1C1=CC=CC=C1)Br)Cl IOEJDDVXHMWQID-UHFFFAOYSA-N 0.000 claims 1
- UKQOOMITZPDVFB-UHFFFAOYSA-N 2-amino-N-[1-(4-chloro-1-cyclobutyl-7-ethoxyindazol-6-yl)ethyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound NC1=NN2C(N=CC=C2)=C1C(=O)NC(C)C1=CC(=C2C=NN(C2=C1OCC)C1CCC1)Cl UKQOOMITZPDVFB-UHFFFAOYSA-N 0.000 claims 1
- VWFONRUQJDLCKG-UHFFFAOYSA-N 2-amino-N-[1-(4-chloro-1-methyl-7-phenylindazol-6-yl)ethyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound NC1=NN2C(N=CC=C2)=C1C(=O)NC(C)C1=CC(=C2C=NN(C2=C1C1=CC=CC=C1)C)Cl VWFONRUQJDLCKG-UHFFFAOYSA-N 0.000 claims 1
- FYLFDFIARXQHJJ-UHFFFAOYSA-N 2-amino-N-[1-(4-chloro-2-cyclobutyl-7-ethoxyindazol-6-yl)ethyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound NC1=NN2C(N=CC=C2)=C1C(=O)NC(C)C=1C=C(C2=CN(N=C2C=1OCC)C1CCC1)Cl FYLFDFIARXQHJJ-UHFFFAOYSA-N 0.000 claims 1
- FYELMOSYRNSIQF-UHFFFAOYSA-N 2-amino-N-[1-(4-chloro-2-methyl-7-phenylindazol-6-yl)ethyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound NC1=NN2C(N=CC=C2)=C1C(=O)NC(C)C=1C=C(C2=CN(N=C2C=1C1=CC=CC=C1)C)Cl FYELMOSYRNSIQF-UHFFFAOYSA-N 0.000 claims 1
- RNKJWBODDJFRPE-UHFFFAOYSA-N 2-amino-N-[1-(4-chloro-3-cyano-7-ethoxy-1H-indazol-6-yl)ethyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound NC1=NN2C(N=CC=C2)=C1C(=O)NC(C)C1=CC(=C2C(=NNC2=C1OCC)C#N)Cl RNKJWBODDJFRPE-UHFFFAOYSA-N 0.000 claims 1
- CJQKGLHPXJJQGY-UHFFFAOYSA-N 2-amino-N-[1-(4-chloro-3-cyano-7-phenyl-1H-indazol-6-yl)ethyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound NC1=NN2C(N=CC=C2)=C1C(=O)NC(C)C1=CC(=C2C(=NNC2=C1C1=CC=CC=C1)C#N)Cl CJQKGLHPXJJQGY-UHFFFAOYSA-N 0.000 claims 1
- AZZOHPRYPSLQMP-UHFFFAOYSA-N 2-amino-N-[1-(4-chloro-3-ethyl-7-phenyl-2H-indazol-6-yl)ethyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound NC1=NN2C(N=CC=C2)=C1C(=O)NC(C)C1=CC(=C2C(=NNC2=C1C1=CC=CC=C1)CC)Cl AZZOHPRYPSLQMP-UHFFFAOYSA-N 0.000 claims 1
- NMBSYNWWGZIZDK-UHFFFAOYSA-N 2-amino-N-[1-(4-chloro-3-methyl-7-phenyl-2H-indazol-6-yl)ethyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound NC1=NN2C(N=CC=C2)=C1C(=O)NC(C)C1=CC(=C2C(=NNC2=C1C1=CC=CC=C1)C)Cl NMBSYNWWGZIZDK-UHFFFAOYSA-N 0.000 claims 1
- LYJIJKUXBWUVEV-UHFFFAOYSA-N 2-amino-N-[1-(4-chloro-7-ethoxy-1-methylindazol-6-yl)ethyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound NC1=NN2C(N=CC=C2)=C1C(=O)NC(C)C1=CC(=C2C=NN(C2=C1OCC)C)Cl LYJIJKUXBWUVEV-UHFFFAOYSA-N 0.000 claims 1
- FLTSAOXWGVRMLB-UHFFFAOYSA-N 2-amino-N-[1-(4-chloro-7-ethoxy-1-propan-2-ylindazol-6-yl)ethyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound NC1=NN2C(N=CC=C2)=C1C(=O)NC(C)C1=CC(=C2C=NN(C2=C1OCC)C(C)C)Cl FLTSAOXWGVRMLB-UHFFFAOYSA-N 0.000 claims 1
- SCCBYIFSNVUXPW-UHFFFAOYSA-N 2-amino-N-[1-(4-chloro-7-ethoxy-1H-indazol-6-yl)ethyl]-5-(5-methoxypyridin-3-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound NC1=NN2C(N=C(C=C2)C=2C=NC=C(C=2)OC)=C1C(=O)NC(C)C1=CC(=C2C=NNC2=C1OCC)Cl SCCBYIFSNVUXPW-UHFFFAOYSA-N 0.000 claims 1
- MCBHNQAUEKCOOV-UHFFFAOYSA-N 2-amino-N-[1-(4-chloro-7-ethoxy-1H-indazol-6-yl)ethyl]-5-[5-(hydroxymethyl)pyridin-3-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound NC1=NN2C(N=C(C=C2)C=2C=NC=C(C=2)CO)=C1C(=O)NC(C)C1=CC(=C2C=NNC2=C1OCC)Cl MCBHNQAUEKCOOV-UHFFFAOYSA-N 0.000 claims 1
- WMCQAFMUKSKFFY-UHFFFAOYSA-N 2-amino-N-[1-(4-chloro-7-ethoxy-1H-indazol-6-yl)ethyl]-5-piperidin-1-ylpyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound NC1=NN2C(N=C(C=C2)N2CCCCC2)=C1C(=O)NC(C)C1=CC(=C2C=NNC2=C1OCC)Cl WMCQAFMUKSKFFY-UHFFFAOYSA-N 0.000 claims 1
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- LWVDZNWNWZKIRM-UHFFFAOYSA-N 2-amino-N-[1-[4-chloro-2-(2-morpholin-4-yl-2-oxoethyl)-7-phenylindazol-6-yl]ethyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound NC1=NN2C(N=CC=C2)=C1C(=O)NC(C)C=1C=C(C2=CN(N=C2C=1C1=CC=CC=C1)CC(=O)N1CCOCC1)Cl LWVDZNWNWZKIRM-UHFFFAOYSA-N 0.000 claims 1
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- UNMNKNWWWJDFPP-UHFFFAOYSA-N 2-amino-N-[1-[4-chloro-7-(2,2-dimethyl-1,1-dioxo-1,4-thiazinan-4-yl)pyrazolo[1,5-a]pyridin-6-yl]ethyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound NC1=NN2C(N=CC=C2)=C1C(=O)NC(C)C=1C=C(C=2N(C=1N1CC(S(CC1)(=O)=O)(C)C)N=CC=2)Cl UNMNKNWWWJDFPP-UHFFFAOYSA-N 0.000 claims 1
- LQDFLAZUUODQHQ-UHFFFAOYSA-N 2-amino-N-[1-[4-chloro-7-(2,3-dihydroxypropoxy)-1H-indazol-6-yl]ethyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound NC1=NN2C(N=CC=C2)=C1C(=O)NC(C)C1=CC(=C2C=NNC2=C1OCC(CO)O)Cl LQDFLAZUUODQHQ-UHFFFAOYSA-N 0.000 claims 1
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- UMAPLNWBQIZJTK-UHFFFAOYSA-N 2-amino-N-[1-[4-chloro-7-[4-(dimethylsulfamoyl)piperidin-1-yl]-1H-indazol-6-yl]ethyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound NC1=NN2C(N=CC=C2)=C1C(=O)NC(C)C=1C=C(C2=CNN=C2C=1N1CCC(CC1)S(=O)(=O)N(C)C)Cl UMAPLNWBQIZJTK-UHFFFAOYSA-N 0.000 claims 1
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- JDPOIBOUXZWMBX-UHFFFAOYSA-N 2-amino-N-[1-[4-chloro-7-ethoxy-2-(2-methoxyethyl)indazol-6-yl]ethyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound NC1=NN2C(N=CC=C2)=C1C(=O)NC(C)C=1C=C(C2=CN(N=C2C=1OCC)CCOC)Cl JDPOIBOUXZWMBX-UHFFFAOYSA-N 0.000 claims 1
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- MJOYAUIUQIYBNE-UHFFFAOYSA-N 2-amino-N-[1-[8-chloro-5-(2-oxo-1-oxa-3,8-diazaspiro[4.5]decan-8-yl)imidazo[1,5-a]pyridin-6-yl]ethyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound NC1=NN2C(N=CC=C2)=C1C(=O)NC(C)C=1C=C(C=2N(C=1N1CCC3(CNC(O3)=O)CC1)C=NC=2)Cl MJOYAUIUQIYBNE-UHFFFAOYSA-N 0.000 claims 1
- MCDADMMUZYANPY-UHFFFAOYSA-N 2-amino-N-[1-[8-chloro-5-(2-oxo-3-oxa-1,8-diazaspiro[4.5]decan-8-yl)imidazo[1,5-a]pyridin-6-yl]ethyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound NC1=NN2C(N=CC=C2)=C1C(=O)NC(C)C=1C=C(C=2N(C=1N1CCC3(COC(N3)=O)CC1)C=NC=2)Cl MCDADMMUZYANPY-UHFFFAOYSA-N 0.000 claims 1
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- ALNPIQGAYSHMRJ-UHFFFAOYSA-N 2-amino-N-[1-[8-chloro-5-(3,3-difluoropyrrolidin-1-yl)imidazo[1,5-a]pyridin-6-yl]ethyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound NC1=NN2C(N=CC=C2)=C1C(=O)NC(C)C=1C=C(C=2N(C=1N1CC(CC1)(F)F)C=NC=2)Cl ALNPIQGAYSHMRJ-UHFFFAOYSA-N 0.000 claims 1
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- FBQIVANOBPTUQO-UHFFFAOYSA-N 2-amino-N-[1-[8-chloro-5-(3-fluoropiperidin-1-yl)imidazo[1,5-a]pyridin-6-yl]ethyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound NC1=NN2C(N=CC=C2)=C1C(=O)NC(C)C=1C=C(C=2N(C=1N1CC(CCC1)F)C=NC=2)Cl FBQIVANOBPTUQO-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- 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
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- 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
Landscapes
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
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| EP16805238.9A EP3371190B1 (en) | 2015-11-06 | 2016-11-04 | Heterocyclic compounds as pi3k-gamma inhibitors |
| PCT/US2016/060468 WO2017079519A1 (en) | 2015-11-06 | 2016-11-04 | Heterocyclic compounds as pi3k-gamma inhibitors |
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| WO2016073889A1 (en) | 2014-11-06 | 2016-05-12 | Lysosomal Therapeutics Inc. | Substituted imidazo[1,5-a]pyrimidines and their use in the treatment of medical disorders |
| HRP20240644T1 (hr) | 2014-11-06 | 2024-08-02 | Bial-R&D Investments, S.A. | Supstituirani pirazolo(1,5-a)pirimidini i njihova uporaba u liječenju medicinskih poremećaja |
| WO2016130501A1 (en) | 2015-02-09 | 2016-08-18 | Incyte Corporation | Aza-heteroaryl compounds as pi3k-gamma inhibitors |
| RS63359B1 (sr) | 2015-11-06 | 2022-07-29 | Incyte Corp | Heterociklična jedinjenja kao inhibitori pi3k-gama |
| WO2017120194A1 (en) | 2016-01-05 | 2017-07-13 | Incyte Corporation | Pyridine and pyridimine compounds as pi3k-gamma inhibitors |
| KR20180132629A (ko) * | 2016-02-25 | 2018-12-12 | 아셰뉴론 에스아 | 글리코시다제 저해제 |
| CA3020305A1 (en) | 2016-04-06 | 2017-10-12 | Lysosomal Therapeutics Inc. | Imidazo [1,5-a]pyrimidinyl carboxamide compounds and their use in the treatment of medical disorders |
| EP3440081A4 (en) | 2016-04-06 | 2019-09-18 | Lysosomal Therapeutics Inc. | PYRROLO [1,2-A] PYRIMIDINYL-CARBOXAMIDE COMPOUNDS AND THEIR USE IN THE TREATMENT OF MEDICAL DISORDER |
| US11192892B2 (en) | 2016-04-06 | 2021-12-07 | Bial—R&D Investments, S.A. | Substituted pyrazolo[1,5-a]pyrimidines for the treatment of medical disorders |
| EP3452455A4 (en) | 2016-05-05 | 2019-11-13 | Lysosomal Therapeutics Inc. | SUBSTITUTED IMDAZO [1,2-] PYRIDINES, SUBSTITUTED IMIDAZO [1,2-] PYRAZINES, RELATED COMPOUNDS AND THEIR USE IN THE TREATMENT OF ILLNESSES |
| SG11201809693SA (en) * | 2016-05-05 | 2018-11-29 | Lysosomal Therapeutics Inc | SUBSTITUTED IMIDAZO[1,2-b]PYRIDAZINES, SUBSTITUTED IMIDAZO[1,5-b]PYRIDAZINES, RELATED COMPOUNDS, AND THEIR USE IN THE TREATMENT OF MEDICAL DISORDERS |
| WO2017223414A1 (en) | 2016-06-24 | 2017-12-28 | Incyte Corporation | HETEROCYCLIC COMPOUNDS AS PI3K-γ INHIBITORS |
| TWI795381B (zh) | 2016-12-21 | 2023-03-11 | 比利時商健生藥品公司 | 作為ｍａｌｔ１抑制劑之吡唑衍生物 |
| US11286264B2 (en) * | 2017-07-28 | 2022-03-29 | Turning Point Therapeutics, Inc. | Macrocyclic compounds and uses thereof |
| KR20240152947A (ko) | 2017-10-18 | 2024-10-22 | 인사이트 코포레이션 | Pi3k-감마 저해제로서의 3차 하이드록시기로 치환된 축합된 이미다졸 유도체 |
| CN111356692B (zh) * | 2017-12-19 | 2021-09-03 | 基石药业（苏州）有限公司 | Ido抑制剂 |
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| AU2020247990A1 (en) | 2019-03-26 | 2021-11-11 | Ventyx Biosciences, Inc. | TYK2 pseudokinase ligands |
| ES2949871T3 (es) | 2019-04-11 | 2023-10-03 | Janssen Pharmaceutica Nv | Anillos de piridina que contienen derivados como inhibidores de MALT1 |
| KR20220047247A (ko) | 2019-06-04 | 2022-04-15 | 아르커스 바이오사이언시즈 인코포레이티드 | 2,3,5-삼치환 피라졸로[1,5-a]피리미딘 화합물 |
| EP3980406A4 (en) | 2019-06-06 | 2023-06-28 | Aligos Therapeutics, Inc. | Heterocyclic compounds |
| KR102938141B1 (ko) | 2019-11-08 | 2026-03-11 | 벤틱스 바이오사이언스, 인크. | Tyk2 슈도키나제 리간드 |
| WO2022228302A1 (en) * | 2021-04-25 | 2022-11-03 | Bionova Pharmaceuticals (Shanghai) Limited | Heteroaromatic carboxamide compounds and its use |
| WO2025146216A1 (zh) * | 2024-01-05 | 2025-07-10 | 成都赜灵生物医药科技有限公司 | 六并五氮杂环酰胺类化合物及其用途 |
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- 2016-11-04 JP JP2018523015A patent/JP6854817B2/ja not_active Expired - Fee Related
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- 2016-11-04 DK DK16805238.9T patent/DK3371190T3/da active
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- 2016-11-04 HU HUE16805238A patent/HUE059324T2/hu unknown
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| US20190062336A1 (en) | 2019-02-28 |
| EP3371190A1 (en) | 2018-09-12 |
| US20230009843A1 (en) | 2023-01-12 |
| JP6854817B2 (ja) | 2021-04-07 |
| PT3371190T (pt) | 2022-07-08 |
| MA43169B1 (fr) | 2022-05-31 |
| TWI824309B (zh) | 2023-12-01 |
| JP2018532760A (ja) | 2018-11-08 |
| TWI744256B (zh) | 2021-11-01 |
| EP4086259A1 (en) | 2022-11-09 |
| DK3371190T3 (da) | 2022-05-23 |
| MA43169A (fr) | 2018-09-12 |
| RS63359B1 (sr) | 2022-07-29 |
| WO2017079519A1 (en) | 2017-05-11 |
| PL3371190T3 (pl) | 2022-11-07 |
| MD3371190T2 (ro) | 2022-09-30 |
| SI3371190T1 (sl) | 2022-08-31 |
| TW202204362A (zh) | 2022-02-01 |
| US11773102B2 (en) | 2023-10-03 |
| LT3371190T (lt) | 2022-08-10 |
| US10472368B2 (en) | 2019-11-12 |
| EP3371190B1 (en) | 2022-03-30 |
| US20200031837A1 (en) | 2020-01-30 |
| CY1125245T1 (el) | 2025-03-28 |
| HUE059324T2 (hu) | 2022-11-28 |
| US11091491B2 (en) | 2021-08-17 |
| TW201726679A (zh) | 2017-08-01 |
| US10065963B2 (en) | 2018-09-04 |
| US20170129899A1 (en) | 2017-05-11 |
| SMT202200250T1 (it) | 2022-07-21 |
| ES2915550T3 (es) | 2022-06-23 |
| AR106595A1 (es) | 2018-01-31 |
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