JP2019522018A5 - - Google Patents
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- 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 |
|---|---|---|---|
| EP16181105.4 | 2016-07-25 | ||
| EP16181105 | 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 (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102445887B1 (ko) | 2016-04-21 | 2022-09-21 | 아스트로사이트 파마슈티컬스, 인코포레이티드 | 신경계 및 심혈관계 병태 치료를 위한 화합물 및 방법 |
| 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 |
| JP2023074248A (ja) | 2021-11-17 | 2023-05-29 | 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 |
| 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 |
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| CA1268404A (en) | 1985-03-15 | 1990-05-01 | Antivirals Inc. | Polynucleotide assay reagent and method |
| DE10139730A1 (de) * | 2001-08-13 | 2003-02-27 | Nanogen Recognomics Gmbh | Verfahren zur Herstellung CNA |
| JP4870562B2 (ja) * | 2003-09-12 | 2012-02-08 | メルク セローノ ソシエテ アノニム | 糖尿病の治療のためのスルホンアミド誘導体 |
| 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 |
| WO2012058645A1 (en) * | 2010-10-29 | 2012-05-03 | Biogen Idec Ma Inc. | Heterocyclic tyrosine kinase inhibitors |
| WO2012175537A1 (en) * | 2011-06-20 | 2012-12-27 | Traslational Cancer Drugs Pharma, S.L. | Method for predicting the clinical response to chemotherapy in a subject with cancer |
| EP2751101A1 (en) | 2011-09-22 | 2014-07-09 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of choline kinase |
| RU2014115979A (ru) | 2011-09-22 | 2015-10-27 | Вертекс Фармасьютикалз Инкорпорейтед | Соединения, используемые как ингибиторы холинкиназы |
| WO2014019908A2 (en) * | 2012-08-02 | 2014-02-06 | Nerviano Medical Sciences S.R.L. | Substituted pyrroles active as kinases inhibitors |
| WO2014165216A1 (en) * | 2013-03-12 | 2014-10-09 | The Trustees Of The University Of Pennsylvania | Diagnosing and treating cancer |
| EP2968358A4 (en) * | 2013-03-15 | 2016-08-10 | Ariad Pharma Inc | NOVEL CHOLINKINASE 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 |
| DK3303334T3 (da) * | 2015-06-03 | 2021-06-28 | Principia Biopharma Inc | Tyrosinkinasehæmmere |
| KR102479746B1 (ko) * | 2016-05-04 | 2022-12-21 | 비.씨.아이. 파르마 | 단백질 키나아제 억제제로서의 아데닌 유도체 |
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2017
- 2017-07-19 EP EP17746421.1A patent/EP3487857B1/en active Active
- 2017-07-19 ES ES17746421T patent/ES2899114T3/es active Active
- 2017-07-19 JP JP2019503678A patent/JP6920411B2/ja active Active
- 2017-07-19 WO PCT/EP2017/068255 patent/WO2018019681A1/en not_active Ceased
- 2017-07-19 US US16/319,951 patent/US10683292B2/en active Active
- 2017-07-19 CN CN201780058594.3A patent/CN109790164B/zh active Active
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