JP2019522018A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2019522018A5 JP2019522018A5 JP2019503678A JP2019503678A JP2019522018A5 JP 2019522018 A5 JP2019522018 A5 JP 2019522018A5 JP 2019503678 A JP2019503678 A JP 2019503678A JP 2019503678 A JP2019503678 A JP 2019503678A JP 2019522018 A5 JP2019522018 A5 JP 2019522018A5
- Authority
- JP
- Japan
- Prior art keywords
- amino
- purin
- cis
- cyclohexanecarboxamide
- chloro
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- PNZXMIKHJXIPEK-UHFFFAOYSA-N cyclohexanecarboxamide Chemical compound NC(=O)C1CCCCC1 PNZXMIKHJXIPEK-UHFFFAOYSA-N 0.000 claims 41
- 150000001875 compounds Chemical class 0.000 claims 32
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 27
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 20
- 229910052757 nitrogen Inorganic materials 0.000 claims 17
- 125000003118 aryl group Chemical group 0.000 claims 13
- 125000001072 heteroaryl group Chemical group 0.000 claims 13
- 229910052799 carbon Inorganic materials 0.000 claims 12
- 229910052739 hydrogen Inorganic materials 0.000 claims 11
- 239000001257 hydrogen Substances 0.000 claims 11
- 150000003839 salts Chemical class 0.000 claims 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 10
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 9
- 125000000623 heterocyclic group Chemical group 0.000 claims 8
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 7
- 239000008194 pharmaceutical composition Substances 0.000 claims 7
- 229910052731 fluorine Inorganic materials 0.000 claims 6
- 239000011737 fluorine Substances 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 229910052801 chlorine Inorganic materials 0.000 claims 5
- 239000000460 chlorine Substances 0.000 claims 5
- 201000010099 disease Diseases 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 150000002431 hydrogen Chemical class 0.000 claims 5
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 4
- 206010028980 Neoplasm Diseases 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 125000001153 fluoro group Chemical group F* 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical group 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 230000002152 alkylating effect Effects 0.000 claims 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 3
- 125000006239 protecting group Chemical group 0.000 claims 3
- -1 4-aminopiperidin-1-yl Chemical group 0.000 claims 2
- 208000024893 Acute lymphoblastic leukemia Diseases 0.000 claims 2
- 208000014697 Acute lymphocytic leukaemia Diseases 0.000 claims 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 2
- 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 2
- 235000011114 ammonium hydroxide Nutrition 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 210000004027 cell Anatomy 0.000 claims 2
- IBNWGIFHWSUUCL-UHFFFAOYSA-N cyclohexanecarboxamide;hydrochloride Chemical compound Cl.NC(=O)C1CCCCC1 IBNWGIFHWSUUCL-UHFFFAOYSA-N 0.000 claims 2
- NZNMSOFKMUBTKW-UHFFFAOYSA-M cyclohexanecarboxylate Chemical compound [O-]C(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-M 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 2
- 201000005787 hematologic cancer Diseases 0.000 claims 2
- 208000024200 hematopoietic and lymphoid system neoplasm Diseases 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 125000006413 ring segment Chemical group 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims 1
- 208000036762 Acute promyelocytic leukaemia Diseases 0.000 claims 1
- 206010003571 Astrocytoma Diseases 0.000 claims 1
- 208000003950 B-cell lymphoma Diseases 0.000 claims 1
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 208000011691 Burkitt lymphomas Diseases 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- STQTWDQGVOUNAG-OCAPTIKFSA-N COC(=O)[C@@H]1CC[C@@H](CC1)N1C=NC2=C(N)N=C(Cl)N=C12 Chemical compound COC(=O)[C@@H]1CC[C@@H](CC1)N1C=NC2=C(N)N=C(Cl)N=C12 STQTWDQGVOUNAG-OCAPTIKFSA-N 0.000 claims 1
- 201000009030 Carcinoma Diseases 0.000 claims 1
- 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims 1
- 208000035473 Communicable disease Diseases 0.000 claims 1
- MYAUKMIXDZPUNU-USLMUHTMSA-N FC(C(=O)O)(F)F.FC(C(=O)O)(F)F.NC1=C2N=CN(C2=NC(=N1)C=1C=C(C(=O)NC2=CC=C(C=C2)CN2CCC(CC2)N(C)C)C=CC1)[C@@H]1CC[C@@H](CC1)C(NC=1SC=C(N1)C)=O Chemical compound FC(C(=O)O)(F)F.FC(C(=O)O)(F)F.NC1=C2N=CN(C2=NC(=N1)C=1C=C(C(=O)NC2=CC=C(C=C2)CN2CCC(CC2)N(C)C)C=CC1)[C@@H]1CC[C@@H](CC1)C(NC=1SC=C(N1)C)=O MYAUKMIXDZPUNU-USLMUHTMSA-N 0.000 claims 1
- 201000008808 Fibrosarcoma Diseases 0.000 claims 1
- 206010018338 Glioma Diseases 0.000 claims 1
- 208000017604 Hodgkin disease Diseases 0.000 claims 1
- 208000021519 Hodgkin lymphoma Diseases 0.000 claims 1
- 208000010747 Hodgkins lymphoma Diseases 0.000 claims 1
- 208000007766 Kaposi sarcoma Diseases 0.000 claims 1
- 206010025323 Lymphomas Diseases 0.000 claims 1
- 208000009018 Medullary thyroid cancer Diseases 0.000 claims 1
- 201000003793 Myelodysplastic syndrome Diseases 0.000 claims 1
- 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims 1
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims 1
- ONCXSLLTHHHLEG-AOOOYVTPSA-N NC1=C2N=CN(C2=NC(=N1)C(=O)N)[C@@H]1CC[C@@H](CC1)C(NC=1SC=C(N=1)C)=O Chemical compound NC1=C2N=CN(C2=NC(=N1)C(=O)N)[C@@H]1CC[C@@H](CC1)C(NC=1SC=C(N=1)C)=O ONCXSLLTHHHLEG-AOOOYVTPSA-N 0.000 claims 1
- QEXLOOFMLDWQLT-MTIAPNHUSA-N NC1=C2N=CN(C2=NC(=N1)C1=CC=C(C(=O)NC2=CC=C(C=C2)CN2CCC(CC2)N(C)C)C=C1)[C@@H]1CC[C@@H](CC1)C(NC1=CC(=CC=C1)OC)=O Chemical compound NC1=C2N=CN(C2=NC(=N1)C1=CC=C(C(=O)NC2=CC=C(C=C2)CN2CCC(CC2)N(C)C)C=C1)[C@@H]1CC[C@@H](CC1)C(NC1=CC(=CC=C1)OC)=O QEXLOOFMLDWQLT-MTIAPNHUSA-N 0.000 claims 1
- HOLDHPSOTBXGOQ-UQDOTLQCSA-N NC1=C2N=CN(C2=NC(=N1)C1=CC=C(C(=O)NC2=CC=C(C=C2)CN2CCN(CC2)C)C=C1)[C@@H]1CC[C@@H](CC1)C(NC1=CC(=CC=C1)OC)=O Chemical compound NC1=C2N=CN(C2=NC(=N1)C1=CC=C(C(=O)NC2=CC=C(C=C2)CN2CCN(CC2)C)C=C1)[C@@H]1CC[C@@H](CC1)C(NC1=CC(=CC=C1)OC)=O HOLDHPSOTBXGOQ-UQDOTLQCSA-N 0.000 claims 1
- HSCVAFOCWCEHKC-GLRZTSSQSA-N NC1=C2N=CN(C2=NC(=N1)C=1C=C(C(=O)N)C=CC=1)[C@@H]1CC[C@@H](CC1)C(NC1=CC(=CC=C1)OC)=O Chemical compound NC1=C2N=CN(C2=NC(=N1)C=1C=C(C(=O)N)C=CC=1)[C@@H]1CC[C@@H](CC1)C(NC1=CC(=CC=C1)OC)=O HSCVAFOCWCEHKC-GLRZTSSQSA-N 0.000 claims 1
- VUTSDHPEHBIXLX-AKAXFMLLSA-N NC1=C2N=CN(C2=NC(=N1)C=1C=C(C(=O)N)C=CC=1)[C@@H]1CC[C@@H](CC1)C(NC=1SC=C(N=1)C)=O Chemical compound NC1=C2N=CN(C2=NC(=N1)C=1C=C(C(=O)N)C=CC=1)[C@@H]1CC[C@@H](CC1)C(NC=1SC=C(N=1)C)=O VUTSDHPEHBIXLX-AKAXFMLLSA-N 0.000 claims 1
- VUTSDHPEHBIXLX-SAZUREKKSA-N NC1=C2N=CN(C2=NC(=N1)C=1C=C(C(=O)N)C=CC=1)[C@@H]1CC[C@H](CC1)C(NC=1SC=C(N=1)C)=O Chemical compound NC1=C2N=CN(C2=NC(=N1)C=1C=C(C(=O)N)C=CC=1)[C@@H]1CC[C@H](CC1)C(NC=1SC=C(N=1)C)=O VUTSDHPEHBIXLX-SAZUREKKSA-N 0.000 claims 1
- GBZFQGAJYUTAKM-YFBXGRPASA-N NC1=C2N=CN(C2=NC(=N1)C=1C=C(C(=O)NC2=CC=C(C=C2)CN2CCC(CC2)N(C)C)C=CC=1)[C@@H]1CC[C@@H](CC1)C(NC1=CC(=CC=C1)OC)=O Chemical compound NC1=C2N=CN(C2=NC(=N1)C=1C=C(C(=O)NC2=CC=C(C=C2)CN2CCC(CC2)N(C)C)C=CC=1)[C@@H]1CC[C@@H](CC1)C(NC1=CC(=CC=C1)OC)=O GBZFQGAJYUTAKM-YFBXGRPASA-N 0.000 claims 1
- VQEOBHLUGBEWGD-COIMTEQESA-N NC1=C2N=CN(C2=NC(=N1)C=1C=C(C(=O)NC2=CC=C(C=C2)CN2CCN(CC2)C)C=CC=1)[C@@H]1CC[C@@H](CC1)C(NC1=CC(=CC=C1)OC)=O Chemical compound NC1=C2N=CN(C2=NC(=N1)C=1C=C(C(=O)NC2=CC=C(C=C2)CN2CCN(CC2)C)C=CC=1)[C@@H]1CC[C@@H](CC1)C(NC1=CC(=CC=C1)OC)=O VQEOBHLUGBEWGD-COIMTEQESA-N 0.000 claims 1
- OTKZSCBGTXCURI-UWUNEBHHSA-N NC1=C2N=CN(C2=NC(=N1)Cl)[C@H]1CC[C@H](CC1)C(=O)NC1=CC=C(C(=O)NC2CCCCC2)C=C1 Chemical compound NC1=C2N=CN(C2=NC(=N1)Cl)[C@H]1CC[C@H](CC1)C(=O)NC1=CC=C(C(=O)NC2CCCCC2)C=C1 OTKZSCBGTXCURI-UWUNEBHHSA-N 0.000 claims 1
- CZEJGJZYTMLTMI-JGZJWPJOSA-N NC1=C2N=CN(C2=NC(=N1)Cl)[C@H]1CC[C@H](CC1)C(=O)NC=1SC2=C(N=1)C=CC(=C2)C(=O)N Chemical compound NC1=C2N=CN(C2=NC(=N1)Cl)[C@H]1CC[C@H](CC1)C(=O)NC=1SC2=C(N=1)C=CC(=C2)C(=O)N CZEJGJZYTMLTMI-JGZJWPJOSA-N 0.000 claims 1
- NRIKKXQDZBEOII-TXEJJXNPSA-N NC1=C2N=CN(C2=NC(=N1)Cl)[C@H]1CC[C@H](CC1)C(=O)NC=1SC2=C(N=1)C=CC(=C2)CC(=O)O Chemical compound NC1=C2N=CN(C2=NC(=N1)Cl)[C@H]1CC[C@H](CC1)C(=O)NC=1SC2=C(N=1)C=CC(=C2)CC(=O)O NRIKKXQDZBEOII-TXEJJXNPSA-N 0.000 claims 1
- QRJIJWRBGGGIDJ-BETUJISGSA-N NC1=C2N=CN(C2=NC(=N1)Cl)[C@H]1CC[C@H](CC1)C(=O)NC=1SC2=C(N=1)C=CC(=C2)CC(=O)OC Chemical compound NC1=C2N=CN(C2=NC(=N1)Cl)[C@H]1CC[C@H](CC1)C(=O)NC=1SC2=C(N=1)C=CC(=C2)CC(=O)OC QRJIJWRBGGGIDJ-BETUJISGSA-N 0.000 claims 1
- VGKKBBAGACAATJ-KNCOVGOOSA-N NC1=C2N=CN(C2=NC(=N1)Cl)[C@H]1CC[C@H](CC1)C(=O)NC=1SC2=C(N=1)C[C@@H]1CC[C@H]2N1C(=O)OC(C)(C)C Chemical compound NC1=C2N=CN(C2=NC(=N1)Cl)[C@H]1CC[C@H](CC1)C(=O)NC=1SC2=C(N=1)C[C@@H]1CC[C@H]2N1C(=O)OC(C)(C)C VGKKBBAGACAATJ-KNCOVGOOSA-N 0.000 claims 1
- KSSKVDAASLUVFC-BETUJISGSA-N NC1=C2N=CN(C2=NC(=N1)Cl)[C@H]1CC[C@H](CC1)C(=O)NC=1SC=2CN(CCC=2N=1)C(=O)OC(C)(C)C Chemical compound NC1=C2N=CN(C2=NC(=N1)Cl)[C@H]1CC[C@H](CC1)C(=O)NC=1SC=2CN(CCC=2N=1)C(=O)OC(C)(C)C KSSKVDAASLUVFC-BETUJISGSA-N 0.000 claims 1
- FTXLUEFEUJUVKQ-PHIMTYICSA-N NC1=C2N=CN(C2=NC(=N1)Cl)[C@H]1CC[C@H](CC1)NC(=O)C=1SC2=C(N=1)C=CC=C2 Chemical compound NC1=C2N=CN(C2=NC(=N1)Cl)[C@H]1CC[C@H](CC1)NC(=O)C=1SC2=C(N=1)C=CC=C2 FTXLUEFEUJUVKQ-PHIMTYICSA-N 0.000 claims 1
- DKINLLUSFMDNQR-AOOOYVTPSA-N NC1=C2N=CN(C2=NC(=N1)Cl)[C@H]1CC[C@H](CC1)NC(=O)C=1SC=C(N=1)C Chemical compound NC1=C2N=CN(C2=NC(=N1)Cl)[C@H]1CC[C@H](CC1)NC(=O)C=1SC=C(N=1)C DKINLLUSFMDNQR-AOOOYVTPSA-N 0.000 claims 1
- OMHPMTVRNYKXQJ-BJHJDKERSA-N NC1=C2N=CN(C2=NC(=N1)Cl)[C@H]1CC[C@H](CC1)NC(=O)NC1=CC(=CC=C1)OC Chemical compound NC1=C2N=CN(C2=NC(=N1)Cl)[C@H]1CC[C@H](CC1)NC(=O)NC1=CC(=CC=C1)OC OMHPMTVRNYKXQJ-BJHJDKERSA-N 0.000 claims 1
- VIPDMQKDNFIHOI-BETUJISGSA-N NC1=C2N=CN(C2=NC(=N1)Cl)[C@H]1CC[C@H](CC1)NC(C1=CC(=CC=C1)OC)=O Chemical compound NC1=C2N=CN(C2=NC(=N1)Cl)[C@H]1CC[C@H](CC1)NC(C1=CC(=CC=C1)OC)=O VIPDMQKDNFIHOI-BETUJISGSA-N 0.000 claims 1
- KOOPNNRLIROOLP-TXEJJXNPSA-N NC1=C2N=CN(C2=NC(=N1)Cl)[C@H]1CC[C@H](CC1)NS(=O)(=O)C1=CC(=CC=C1)OC Chemical compound NC1=C2N=CN(C2=NC(=N1)Cl)[C@H]1CC[C@H](CC1)NS(=O)(=O)C1=CC(=CC=C1)OC KOOPNNRLIROOLP-TXEJJXNPSA-N 0.000 claims 1
- 206010029260 Neuroblastoma Diseases 0.000 claims 1
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims 1
- 206010033701 Papillary thyroid cancer Diseases 0.000 claims 1
- 201000010208 Seminoma Diseases 0.000 claims 1
- 206010041067 Small cell lung cancer Diseases 0.000 claims 1
- 206010042971 T-cell lymphoma Diseases 0.000 claims 1
- 208000027585 T-cell non-Hodgkin lymphoma Diseases 0.000 claims 1
- 208000024770 Thyroid neoplasm Diseases 0.000 claims 1
- 201000006083 Xeroderma Pigmentosum Diseases 0.000 claims 1
- 230000001154 acute effect Effects 0.000 claims 1
- 238000011394 anticancer treatment Methods 0.000 claims 1
- 239000002246 antineoplastic agent Substances 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 210000002798 bone marrow cell Anatomy 0.000 claims 1
- 210000000481 breast Anatomy 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 201000007455 central nervous system cancer Diseases 0.000 claims 1
- 208000025997 central nervous system neoplasm Diseases 0.000 claims 1
- 210000003679 cervix uteri Anatomy 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 claims 1
- 229960001231 choline Drugs 0.000 claims 1
- 210000001072 colon Anatomy 0.000 claims 1
- 229940127089 cytotoxic agent Drugs 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 210000003238 esophagus Anatomy 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 210000000232 gallbladder Anatomy 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 claims 1
- 210000003734 kidney Anatomy 0.000 claims 1
- 208000032839 leukemia Diseases 0.000 claims 1
- 210000004185 liver Anatomy 0.000 claims 1
- 210000004072 lung Anatomy 0.000 claims 1
- 210000004324 lymphatic system Anatomy 0.000 claims 1
- 208000023356 medullary thyroid gland carcinoma Diseases 0.000 claims 1
- 201000001441 melanoma Diseases 0.000 claims 1
- 230000004060 metabolic process Effects 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 208000007538 neurilemmoma Diseases 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- 201000008968 osteosarcoma Diseases 0.000 claims 1
- 210000001672 ovary Anatomy 0.000 claims 1
- 210000000496 pancreas Anatomy 0.000 claims 1
- 201000005528 peripheral nervous system neoplasm Diseases 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 230000002062 proliferating effect Effects 0.000 claims 1
- 210000002307 prostate Anatomy 0.000 claims 1
- 201000009410 rhabdomyosarcoma Diseases 0.000 claims 1
- 210000003491 skin Anatomy 0.000 claims 1
- 208000000587 small cell lung carcinoma Diseases 0.000 claims 1
- 206010041823 squamous cell carcinoma Diseases 0.000 claims 1
- 210000002784 stomach Anatomy 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 208000001608 teratocarcinoma Diseases 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 201000002510 thyroid cancer Diseases 0.000 claims 1
- 210000001685 thyroid gland Anatomy 0.000 claims 1
- 208000030045 thyroid gland papillary carcinoma Diseases 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 210000003932 urinary bladder Anatomy 0.000 claims 1
- 0 *C1C(*C*2)=C2*=C(*)*1 Chemical compound *C1C(*C*2)=C2*=C(*)*1 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP16181105 | 2016-07-25 | ||
| EP16181105.4 | 2016-07-25 | ||
| PCT/EP2017/068255 WO2018019681A1 (en) | 2016-07-25 | 2017-07-19 | Purine and 3-deazapurine analogues as choline kinase inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019522018A JP2019522018A (ja) | 2019-08-08 |
| JP2019522018A5 true JP2019522018A5 (enExample) | 2020-07-27 |
| JP6920411B2 JP6920411B2 (ja) | 2021-08-18 |
Family
ID=56550132
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019503678A Active JP6920411B2 (ja) | 2016-07-25 | 2017-07-19 | コリンキナーゼ阻害剤としてのプリン及び３−デアザプリンアナログ |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US10683292B2 (enExample) |
| EP (1) | EP3487857B1 (enExample) |
| JP (1) | JP6920411B2 (enExample) |
| CN (1) | CN109790164B (enExample) |
| ES (1) | ES2899114T3 (enExample) |
| WO (1) | WO2018019681A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109310695B (zh) | 2016-04-21 | 2022-04-01 | 阿斯特罗赛特制药公司 | 治疗神经和心血管病况的化合物和方法 |
| CN110183442A (zh) * | 2019-06-06 | 2019-08-30 | 无锡合全药业有限公司 | 一种1 -(乙氧羰基)咪唑并[1, 5]吡啶-6-羧酸的合成方法 |
| US20240368164A1 (en) * | 2021-04-28 | 2024-11-07 | Astrocyle Pharmaceuticals, Inc. | Purine nucleosides, their intermediates, and methods of preparation thereof |
| JP7856405B2 (ja) | 2021-11-17 | 2026-05-11 | 信越化学工業株式会社 | 有機膜形成用組成物、パターン形成方法並びに有機膜形成用化合物及び重合体 |
| WO2023205366A1 (en) * | 2022-04-20 | 2023-10-26 | Carthronix, Inc. | Small molecule modulators of gp130 signaling pathways |
| WO2024044751A2 (en) * | 2022-08-26 | 2024-02-29 | Wake Forest University Health Sciences | Peroxiredoxin 3 inhibitors and methods of use for treating cancer |
| CN115403593B (zh) * | 2022-09-22 | 2024-02-02 | 河南师范大学 | 一种环加成合成手性嘌呤[3,2-c]并噁唑化合物的方法 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2528107B2 (ja) * | 1985-03-15 | 1996-08-28 | サマ−トン，ジエ−ムス | ポリヌクレオチド測定試薬と方法 |
| DE10139730A1 (de) * | 2001-08-13 | 2003-02-27 | Nanogen Recognomics Gmbh | Verfahren zur Herstellung CNA |
| ES2385219T3 (es) * | 2003-09-12 | 2012-07-19 | Merck Serono Sa | Derivados de sulfonamida para el tratamiento de diabetes |
| ES2237332B1 (es) | 2004-01-14 | 2006-11-01 | Consejo Sup. Investig. Cientificas | Derivados de piridinio y quinolinio. |
| ES2277568B1 (es) | 2005-12-30 | 2008-04-01 | Consejo Superior De Investigaciones Cientificas | Derivados de triterpenoquinona y triterpenofenoles y su aplicacion para el tratamiento de tumores y enfermedades parasitarias. |
| WO2009116074A2 (en) * | 2008-02-13 | 2009-09-24 | Cadila Healthcare Limited | Substituted benzimidazoles as cannabinoid modulator |
| US9273028B2 (en) * | 2010-10-29 | 2016-03-01 | Biogen Ma Inc. | Heterocyclic tyrosine kinase inhibitors |
| AU2012274156A1 (en) * | 2011-06-20 | 2014-01-23 | Traslational Cancer Drugs Pharma, S.L. | Method for predicting the clinical response to chemotherapy in a subject with cancer |
| US20130281445A1 (en) | 2011-09-22 | 2013-10-24 | Simon Everitt | Compounds useful as inhibitors of choline kinase |
| KR20140064987A (ko) | 2011-09-22 | 2014-05-28 | 버텍스 파마슈티칼스 인코포레이티드 | 콜린 키나제의 억제제로서 유용한 화합물 |
| CN104507923B (zh) * | 2012-08-02 | 2018-02-09 | 内尔维阿诺医学科学有限公司 | 作为激酶抑制剂的取代的吡咯类活性剂 |
| WO2014165216A1 (en) * | 2013-03-12 | 2014-10-09 | The Trustees Of The University Of Pennsylvania | Diagnosing and treating cancer |
| WO2014151761A1 (en) * | 2013-03-15 | 2014-09-25 | Ariad Pharmaceuticals, Inc. | Novel choline kinase inhibitors |
| WO2015151006A1 (en) * | 2014-03-29 | 2015-10-08 | Lupin Limited | Substituted purine compounds as btk inhibitors |
| ES2482290B1 (es) | 2014-06-05 | 2015-05-19 | Universidad De Granada | Inhibidores polares simétricos de colina cinasa con actividad antitumoral |
| EP3912979B1 (en) * | 2015-06-03 | 2026-03-25 | Principia Biopharma Inc. | Tyrosine kinase inhibitors |
| US11236093B2 (en) * | 2016-05-04 | 2022-02-01 | B.C.I. Pharma | Adenine derivatives as protein kinase inhibitors |
-
2017
- 2017-07-19 ES ES17746421T patent/ES2899114T3/es active Active
- 2017-07-19 EP EP17746421.1A patent/EP3487857B1/en active Active
- 2017-07-19 WO PCT/EP2017/068255 patent/WO2018019681A1/en not_active Ceased
- 2017-07-19 CN CN201780058594.3A patent/CN109790164B/zh active Active
- 2017-07-19 JP JP2019503678A patent/JP6920411B2/ja active Active
- 2017-07-19 US US16/319,951 patent/US10683292B2/en active Active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ES2797955T3 (es) | Moduladores de la ruta de hedgehog | |
| JP2023512038A5 (enExample) | ||
| ES2373688T3 (es) | Pirrolo[2,3-b]piridinas y pirrolo[2,3-b]pirimidinas sustituidas con heteroarilo como inhibidores de quinasas janus. | |
| RU2016141645A (ru) | ИНГИБИТОРЫ TrkA КИНАЗЫ, ОСНОВАННЫЕ НА НИХ КОМПОЗИЦИИ И СПОСОБЫ | |
| AU2021202728A1 (en) | Aryl, Heteroaryl, And Heterocyclic Compounds For Treatment Of Medical Disorders | |
| JP2022544946A5 (enExample) | ||
| JP2014530238A5 (enExample) | ||
| RU2017105296A (ru) | Новые соединения | |
| JP2017508766A5 (enExample) | ||
| CA3061392A1 (en) | Azalactam compounds as hpk1 inhibitors | |
| JP2012525335A5 (enExample) | ||
| RU2015124917A (ru) | Новые бициклические фенилпиридины/пиразины для лечения рака | |
| RU2011114487A (ru) | Гетероциклические соединения как ингибиторы протеинкиназы | |
| JP2017537080A5 (enExample) | ||
| CN103002897A (zh) | 特定氨基-哒嗪类，与其组合物，及其使用方法 | |
| IL187690A (en) | Derivatives 1, 2, 4 - Triazolo - 1, 6 - Naphthiridines as inhibitors of AKT activity for use in the preparation of drugs for the treatment of cancer | |
| RU2017138100A (ru) | Имидазолонилхинолины и их применение в качестве ингибиторов киназы атм | |
| JP2010508274A (ja) | アニリノピペラジン誘導体およびアニリノピペラジン誘導体を使用する方法 | |
| JP2006503010A5 (enExample) | ||
| JP2011520896A5 (enExample) | ||
| AU2023261964A1 (en) | Compounds for inhibiting kif18a | |
| JP2018512062A5 (enExample) | ||
| BR112019013287A2 (pt) | compostos de pirazolopirimidina e métodos de uso dos mesmos | |
| JP2004534065A5 (enExample) | ||
| JP2014528450A5 (enExample) |