JP2012525367A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2012525367A5 JP2012525367A5 JP2012507826A JP2012507826A JP2012525367A5 JP 2012525367 A5 JP2012525367 A5 JP 2012525367A5 JP 2012507826 A JP2012507826 A JP 2012507826A JP 2012507826 A JP2012507826 A JP 2012507826A JP 2012525367 A5 JP2012525367 A5 JP 2012525367A5
- Authority
- JP
- Japan
- Prior art keywords
- pyridin
- benzimidazol
- methanone
- piperidin
- dimethylamino
- 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.)
- Ceased
Links
- -1 amino, hydroxy Chemical group 0.000 claims description 72
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 12
- 206010028980 Neoplasm Diseases 0.000 claims description 10
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
- 201000009030 Carcinoma Diseases 0.000 claims description 4
- 206010009944 Colon cancer Diseases 0.000 claims description 4
- 208000009956 adenocarcinoma Diseases 0.000 claims description 4
- 210000004027 cell Anatomy 0.000 claims description 4
- 201000005787 hematologic cancer Diseases 0.000 claims description 4
- 208000024200 hematopoietic and lymphoid system neoplasm Diseases 0.000 claims description 4
- 208000003950 B-cell lymphoma Diseases 0.000 claims description 3
- 206010006187 Breast cancer Diseases 0.000 claims description 3
- 208000026310 Breast neoplasm Diseases 0.000 claims description 3
- 208000032612 Glial tumor Diseases 0.000 claims description 3
- 206010018338 Glioma Diseases 0.000 claims description 3
- 208000034578 Multiple myelomas Diseases 0.000 claims description 3
- 206010035226 Plasma cell myeloma Diseases 0.000 claims description 3
- 206010060862 Prostate cancer Diseases 0.000 claims description 3
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 3
- 208000005718 Stomach Neoplasms Diseases 0.000 claims description 3
- 208000029742 colonic neoplasm Diseases 0.000 claims description 3
- 206010017758 gastric cancer Diseases 0.000 claims description 3
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 3
- 201000011549 stomach cancer Diseases 0.000 claims description 3
- GYESQEMZKJMLLT-UHFFFAOYSA-N (2-isoquinolin-4-ylpyridin-4-yl)-[5-(piperazine-1-carbonyl)-1h-imidazo[4,5-b]pyridin-2-yl]methanone Chemical compound C=1C=C2N=C(C(=O)C=3C=C(N=CC=3)C=3C4=CC=CC=C4C=NC=3)NC2=NC=1C(=O)N1CCNCC1 GYESQEMZKJMLLT-UHFFFAOYSA-N 0.000 claims description 2
- ULPRVYASATXOFK-UHFFFAOYSA-N (2-isoquinolin-4-ylpyridin-4-yl)-[6-(4-propan-2-ylpiperazin-1-yl)-1h-benzimidazol-2-yl]methanone Chemical compound C1CN(C(C)C)CCN1C1=CC=C(NC(=N2)C(=O)C=3C=C(N=CC=3)C=3C4=CC=CC=C4C=NC=3)C2=C1 ULPRVYASATXOFK-UHFFFAOYSA-N 0.000 claims description 2
- WXKNWWKHTSLSEL-UHFFFAOYSA-N 2-(3,5-dimethyl-1h-pyrazol-4-yl)-4-[6-(piperazine-1-carbonyl)-1h-benzimidazole-2-carbonyl]benzonitrile Chemical compound CC1=NNC(C)=C1C1=CC(C(=O)C=2NC3=CC(=CC=C3N=2)C(=O)N2CCNCC2)=CC=C1C#N WXKNWWKHTSLSEL-UHFFFAOYSA-N 0.000 claims description 2
- WJBDBQDFKAJTSV-UHFFFAOYSA-N 2-(3-methylisoquinolin-4-yl)-4-[6-(piperazine-1-carbonyl)-1h-benzimidazole-2-carbonyl]benzonitrile Chemical compound CC1=NC=C2C=CC=CC2=C1C(C(=CC=1)C#N)=CC=1C(=O)C(NC1=CC=2)=NC1=CC=2C(=O)N1CCNCC1 WJBDBQDFKAJTSV-UHFFFAOYSA-N 0.000 claims description 2
- QRFNPZUNAUBFQC-UHFFFAOYSA-N 4-[5-[4-(dimethylamino)piperidin-1-yl]-1h-imidazo[4,5-b]pyridine-2-carbonyl]-2-(1,3,5-trimethylpyrazol-4-yl)benzonitrile Chemical compound C1CC(N(C)C)CCN1C1=CC=C(N=C(N2)C(=O)C=3C=C(C(C#N)=CC=3)C3=C(N(C)N=C3C)C)C2=N1 QRFNPZUNAUBFQC-UHFFFAOYSA-N 0.000 claims description 2
- JAJBPEMNCZFNCD-UHFFFAOYSA-N 4-[5-[4-(dimethylamino)piperidin-1-yl]-1h-imidazo[4,5-b]pyridine-2-carbonyl]-2-(2-methylimidazo[1,2-a]pyridin-3-yl)benzonitrile Chemical compound C1CC(N(C)C)CCN1C1=CC=C(N=C(N2)C(=O)C=3C=C(C(C#N)=CC=3)C=3N4C=CC=CC4=NC=3C)C2=N1 JAJBPEMNCZFNCD-UHFFFAOYSA-N 0.000 claims description 2
- OBEDBWZPPYGENC-UHFFFAOYSA-N 4-[6-[4-(dimethylamino)piperidin-1-yl]-1h-benzimidazole-2-carbonyl]-1-methoxy-2-phenylcyclohexa-2,4-diene-1-carboxamide Chemical compound COC1(C(N)=O)CC=C(C(=O)C=2NC3=CC=C(C=C3N=2)N2CCC(CC2)N(C)C)C=C1C1=CC=CC=C1 OBEDBWZPPYGENC-UHFFFAOYSA-N 0.000 claims description 2
- 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
- 208000036762 Acute promyelocytic leukaemia Diseases 0.000 claims description 2
- 206010003571 Astrocytoma 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
- 206010005003 Bladder cancer Diseases 0.000 claims description 2
- 208000011691 Burkitt lymphomas Diseases 0.000 claims description 2
- 206010008342 Cervix carcinoma Diseases 0.000 claims description 2
- 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims description 2
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 2
- 206010014733 Endometrial cancer Diseases 0.000 claims description 2
- 206010014759 Endometrial neoplasm Diseases 0.000 claims description 2
- 208000006168 Ewing Sarcoma Diseases 0.000 claims description 2
- 201000008808 Fibrosarcoma Diseases 0.000 claims description 2
- 206010017993 Gastrointestinal neoplasms Diseases 0.000 claims description 2
- 206010051066 Gastrointestinal stromal tumour 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
- 208000008839 Kidney Neoplasms Diseases 0.000 claims description 2
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 2
- 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 claims description 2
- 206010025323 Lymphomas Diseases 0.000 claims description 2
- 201000003793 Myelodysplastic syndrome 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
- 206010029260 Neuroblastoma Diseases 0.000 claims description 2
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims description 2
- 208000010505 Nose Neoplasms Diseases 0.000 claims description 2
- 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 claims description 2
- 206010038389 Renal cancer Diseases 0.000 claims description 2
- 206010039491 Sarcoma Diseases 0.000 claims description 2
- 201000010208 Seminoma Diseases 0.000 claims description 2
- 208000000453 Skin Neoplasms Diseases 0.000 claims description 2
- 206010041067 Small cell lung cancer Diseases 0.000 claims description 2
- 206010042971 T-cell lymphoma Diseases 0.000 claims description 2
- 208000027585 T-cell non-Hodgkin lymphoma Diseases 0.000 claims description 2
- 208000024770 Thyroid neoplasm Diseases 0.000 claims description 2
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 2
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims description 2
- 201000006083 Xeroderma Pigmentosum Diseases 0.000 claims description 2
- QFPALJFKLKEVNR-UHFFFAOYSA-N [2-(2,3-difluoro-6-methoxyphenyl)pyridin-4-yl]-[6-[4-(dimethylamino)piperidin-1-yl]-1h-benzimidazol-2-yl]methanone Chemical compound COC1=CC=C(F)C(F)=C1C1=CC(C(=O)C=2NC3=CC=C(C=C3N=2)N2CCC(CC2)N(C)C)=CC=N1 QFPALJFKLKEVNR-UHFFFAOYSA-N 0.000 claims description 2
- RWKNIINLNXUVLK-UHFFFAOYSA-N [5-(1,4-diazepan-1-yl)-1h-imidazo[4,5-b]pyridin-2-yl]-[2-(1,3,5-trimethylpyrazol-4-yl)pyridin-4-yl]methanone Chemical compound CC1=NN(C)C(C)=C1C1=CC(C(=O)C=2NC3=NC(=CC=C3N=2)N2CCNCCC2)=CC=N1 RWKNIINLNXUVLK-UHFFFAOYSA-N 0.000 claims description 2
- UESAGYUKLKMQMV-UHFFFAOYSA-N [6-[4-(dimethylamino)piperidin-1-yl]-1h-benzimidazol-2-yl]-[2-(1h-indol-3-yl)pyridin-4-yl]methanone Chemical compound C1CC(N(C)C)CCN1C1=CC=C(N=C(N2)C(=O)C=3C=C(N=CC=3)C=3C4=CC=CC=C4NC=3)C2=C1 UESAGYUKLKMQMV-UHFFFAOYSA-N 0.000 claims description 2
- HTAGFNZZPCRWLK-UHFFFAOYSA-N [6-[4-(dimethylamino)piperidin-1-yl]-1h-benzimidazol-2-yl]-[2-(1h-indol-4-yl)pyridin-4-yl]methanone Chemical compound C1CC(N(C)C)CCN1C1=CC=C(N=C(N2)C(=O)C=3C=C(N=CC=3)C=3C=4C=CNC=4C=CC=3)C2=C1 HTAGFNZZPCRWLK-UHFFFAOYSA-N 0.000 claims description 2
- SJLLDOHQMMIRRT-UHFFFAOYSA-N [6-[4-(dimethylamino)piperidin-1-yl]-1h-benzimidazol-2-yl]-[2-(5-methyl-1h-pyrazol-4-yl)pyridin-4-yl]methanone Chemical compound C1CC(N(C)C)CCN1C1=CC=C(N=C(N2)C(=O)C=3C=C(N=CC=3)C3=C(NN=C3)C)C2=C1 SJLLDOHQMMIRRT-UHFFFAOYSA-N 0.000 claims description 2
- UAQBLDVNMHVXBX-UHFFFAOYSA-N [6-[4-(dimethylamino)piperidin-1-yl]-1h-benzimidazol-2-yl]-[2-(7-methyl-1h-indol-3-yl)pyridin-4-yl]methanone Chemical compound C1CC(N(C)C)CCN1C1=CC=C(N=C(N2)C(=O)C=3C=C(N=CC=3)C=3C4=CC=CC(C)=C4NC=3)C2=C1 UAQBLDVNMHVXBX-UHFFFAOYSA-N 0.000 claims description 2
- 230000001154 acute effect Effects 0.000 claims description 2
- 201000010881 cervical cancer Diseases 0.000 claims description 2
- 208000032852 chronic lymphocytic leukemia Diseases 0.000 claims description 2
- 201000011243 gastrointestinal stromal tumor Diseases 0.000 claims description 2
- 201000010536 head and neck cancer Diseases 0.000 claims description 2
- 208000014829 head and neck neoplasm Diseases 0.000 claims description 2
- 201000010982 kidney cancer Diseases 0.000 claims description 2
- 208000032839 leukemia Diseases 0.000 claims description 2
- 201000007270 liver cancer Diseases 0.000 claims description 2
- 208000014018 liver neoplasm Diseases 0.000 claims description 2
- 201000005202 lung cancer Diseases 0.000 claims description 2
- 208000020816 lung neoplasm Diseases 0.000 claims description 2
- 230000002071 myeloproliferative effect Effects 0.000 claims description 2
- 208000037830 nasal cancer Diseases 0.000 claims description 2
- 208000007538 neurilemmoma Diseases 0.000 claims description 2
- 201000008968 osteosarcoma Diseases 0.000 claims description 2
- 201000005528 peripheral nervous system neoplasm Diseases 0.000 claims description 2
- 201000009410 rhabdomyosarcoma Diseases 0.000 claims description 2
- 206010039667 schwannoma Diseases 0.000 claims description 2
- 208000000587 small cell lung carcinoma Diseases 0.000 claims description 2
- 206010041823 squamous cell carcinoma Diseases 0.000 claims description 2
- 208000011580 syndromic disease Diseases 0.000 claims description 2
- 208000001608 teratocarcinoma Diseases 0.000 claims description 2
- 201000002510 thyroid cancer Diseases 0.000 claims description 2
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims description 2
- 201000005112 urinary bladder cancer Diseases 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims 47
- 125000000217 alkyl group Chemical group 0.000 claims 32
- 125000003545 alkoxy group Chemical group 0.000 claims 28
- 125000004093 cyano group Chemical group *C#N 0.000 claims 25
- 229910052736 halogen Inorganic materials 0.000 claims 24
- 150000002367 halogens Chemical class 0.000 claims 23
- 125000003118 aryl group Chemical group 0.000 claims 22
- 125000001072 heteroaryl group Chemical group 0.000 claims 13
- 125000000623 heterocyclic group Chemical group 0.000 claims 13
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 8
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 8
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 7
- 150000001204 N-oxides Chemical class 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 7
- 239000012453 solvate Substances 0.000 claims 7
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 6
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 5
- 201000011510 cancer Diseases 0.000 claims 5
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 3
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 3
- 125000006574 non-aromatic ring group Chemical group 0.000 claims 3
- 208000000461 Esophageal Neoplasms Diseases 0.000 claims 2
- 206010030155 Oesophageal carcinoma Diseases 0.000 claims 2
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 125000005334 azaindolyl group Chemical group N1N=C(C2=CC=CC=C12)* 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 201000004101 esophageal cancer Diseases 0.000 claims 2
- 230000003325 follicular Effects 0.000 claims 2
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 2
- 201000002528 pancreatic cancer Diseases 0.000 claims 2
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 2
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 210000001685 thyroid gland Anatomy 0.000 claims 2
- FDWOHJOEJDYIKC-UHFFFAOYSA-N (2-isoquinolin-4-ylpyridin-4-yl)-[6-(piperazine-1-carbonyl)-1h-benzimidazol-2-yl]methanone Chemical compound C=1C=C2N=C(C(=O)C=3C=C(N=CC=3)C=3C4=CC=CC=C4C=NC=3)NC2=CC=1C(=O)N1CCNCC1 FDWOHJOEJDYIKC-UHFFFAOYSA-N 0.000 claims 1
- WOWAYCRTODXNHC-UHFFFAOYSA-N 2-(1h-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile Chemical compound N#CC1=CC=CC=C1C1=CN=CC2=C1C=CN2 WOWAYCRTODXNHC-UHFFFAOYSA-N 0.000 claims 1
- PCWXWSDCFQZIKP-UHFFFAOYSA-N 2-[4-[6-[4-(dimethylamino)piperidin-1-yl]-1h-benzimidazole-2-carbonyl]pyridin-2-yl]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC=C1C1=CC(C(=O)C=2NC3=CC(=CC=C3N=2)N2CCC(CC2)N(C)C)=CC=N1 PCWXWSDCFQZIKP-UHFFFAOYSA-N 0.000 claims 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 1
- RSAQLGNUSSDKPJ-UHFFFAOYSA-N 2-isoquinolin-4-yl-4-(5-piperazin-1-yl-1h-imidazo[4,5-b]pyridine-2-carbonyl)benzonitrile Chemical compound C=1C=C(C#N)C(C=2C3=CC=CC=C3C=NC=2)=CC=1C(=O)C(NC1=N2)=NC1=CC=C2N1CCNCC1 RSAQLGNUSSDKPJ-UHFFFAOYSA-N 0.000 claims 1
- XGCQSXXDPHVKNA-UHFFFAOYSA-N 4-(5-piperazin-1-yl-1h-imidazo[4,5-b]pyridine-2-carbonyl)-2-(1,3,5-trimethylpyrazol-4-yl)benzonitrile Chemical compound CC1=NN(C)C(C)=C1C1=CC(C(=O)C=2NC3=NC(=CC=C3N=2)N2CCNCC2)=CC=C1C#N XGCQSXXDPHVKNA-UHFFFAOYSA-N 0.000 claims 1
- UOOPUMIMUFIYRM-UHFFFAOYSA-N 4-(5-pyrrolidin-3-yloxy-1h-imidazo[4,5-b]pyridine-2-carbonyl)-2-(1,3,5-trimethylpyrazol-4-yl)benzonitrile Chemical compound CC1=NN(C)C(C)=C1C1=CC(C(=O)C=2NC3=NC(OC4CNCC4)=CC=C3N=2)=CC=C1C#N UOOPUMIMUFIYRM-UHFFFAOYSA-N 0.000 claims 1
- FKCGPPSRDPUEMX-UHFFFAOYSA-N 4-(5-pyrrolidin-3-yloxy-1h-imidazo[4,5-b]pyridine-2-carbonyl)-2-(1h-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile Chemical compound C=1C=C(C#N)C(C=2C=3C=CNC=3C=NC=2)=CC=1C(=O)C(NC1=N2)=NC1=CC=C2OC1CCNC1 FKCGPPSRDPUEMX-UHFFFAOYSA-N 0.000 claims 1
- SVVWDAVROKBLLM-UHFFFAOYSA-N 4-[5-(2,6-diazaspiro[3.3]heptan-2-yl)-1h-imidazo[4,5-b]pyridine-2-carbonyl]-2-(1,3,5-trimethylpyrazol-4-yl)benzonitrile Chemical compound CC1=NN(C)C(C)=C1C1=CC(C(=O)C=2NC3=NC(=CC=C3N=2)N2CC3(CNC3)C2)=CC=C1C#N SVVWDAVROKBLLM-UHFFFAOYSA-N 0.000 claims 1
- YTQVHCYNJSQYBQ-UHFFFAOYSA-N 4-[5-(3,3-dimethyl-2-oxopiperazin-1-yl)-1h-imidazo[4,5-b]pyridine-2-carbonyl]-2-(1,3,5-trimethylpyrazol-4-yl)benzonitrile Chemical compound CC1=NN(C)C(C)=C1C1=CC(C(=O)C=2NC3=NC(=CC=C3N=2)N2C(C(C)(C)NCC2)=O)=CC=C1C#N YTQVHCYNJSQYBQ-UHFFFAOYSA-N 0.000 claims 1
- CXUFMCLAOGFZCL-UHFFFAOYSA-N 4-[5-(3,6-diazabicyclo[3.2.0]heptan-3-yl)-1h-imidazo[4,5-b]pyridine-2-carbonyl]-2-(1,3,5-trimethylpyrazol-4-yl)benzonitrile Chemical compound CC1=NN(C)C(C)=C1C1=CC(C(=O)C=2NC3=NC(=CC=C3N=2)N2CC3NCC3C2)=CC=C1C#N CXUFMCLAOGFZCL-UHFFFAOYSA-N 0.000 claims 1
- ICWPIAFNXZRHOY-UHFFFAOYSA-N 4-[5-(3-aminopyrrolidin-1-yl)-1h-imidazo[4,5-b]pyridine-2-carbonyl]-2-(1,3,5-trimethylpyrazol-4-yl)benzonitrile Chemical compound CC1=NN(C)C(C)=C1C1=CC(C(=O)C=2NC3=NC(=CC=C3N=2)N2CC(N)CC2)=CC=C1C#N ICWPIAFNXZRHOY-UHFFFAOYSA-N 0.000 claims 1
- SVSQYSGVBLHFIR-UHFFFAOYSA-N 4-[5-(4-hydroxypiperidin-1-yl)-1h-imidazo[4,5-b]pyridine-2-carbonyl]-2-(1h-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile Chemical compound C1CC(O)CCN1C1=CC=C(N=C(N2)C(=O)C=3C=C(C(C#N)=CC=3)C=3C=4C=CNC=4C=NC=3)C2=N1 SVSQYSGVBLHFIR-UHFFFAOYSA-N 0.000 claims 1
- XBBDXTZEQSGHSX-UHFFFAOYSA-N 4-[5-(6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl)-1h-imidazo[4,5-b]pyridine-2-carbonyl]-2-(1,3,5-trimethylpyrazol-4-yl)benzonitrile Chemical compound CC1=NN(C)C(C)=C1C1=CC(C(=O)C=2NC3=NC(=CC=C3N=2)N2CC3=NC=CN3CC2)=CC=C1C#N XBBDXTZEQSGHSX-UHFFFAOYSA-N 0.000 claims 1
- UMNVIAGLNGIVNV-UHFFFAOYSA-N 4-[5-(6-amino-3-azabicyclo[3.1.0]hexan-3-yl)-1h-imidazo[4,5-b]pyridine-2-carbonyl]-2-(1,3,5-trimethylpyrazol-4-yl)benzonitrile Chemical compound CC1=NN(C)C(C)=C1C1=CC(C(=O)C=2NC3=NC(=CC=C3N=2)N2CC3C(N)C3C2)=CC=C1C#N UMNVIAGLNGIVNV-UHFFFAOYSA-N 0.000 claims 1
- NMRMRRPAIRIPGY-UHFFFAOYSA-N 4-[5-(pyrrolidin-3-ylamino)-1h-imidazo[4,5-b]pyridine-2-carbonyl]-2-(1,3,5-trimethylpyrazol-4-yl)benzonitrile Chemical compound CC1=NN(C)C(C)=C1C1=CC(C(=O)C=2NC3=NC(NC4CNCC4)=CC=C3N=2)=CC=C1C#N NMRMRRPAIRIPGY-UHFFFAOYSA-N 0.000 claims 1
- CKMCPMVEGWKUIK-UHFFFAOYSA-N 4-[5-[2-(4-methylpiperazin-1-yl)ethoxy]-1h-imidazo[4,5-b]pyridine-2-carbonyl]-2-(1,3,5-trimethylpyrazol-4-yl)benzonitrile Chemical compound C1CN(C)CCN1CCOC1=CC=C(N=C(N2)C(=O)C=3C=C(C(C#N)=CC=3)C3=C(N(C)N=C3C)C)C2=N1 CKMCPMVEGWKUIK-UHFFFAOYSA-N 0.000 claims 1
- PKZOUEKXSHRMJY-UHFFFAOYSA-N 4-[5-[4-(dimethylamino)piperidin-1-yl]-1h-imidazo[4,5-b]pyridine-2-carbonyl]-2-(1,3,5-trimethylpyrazol-4-yl)benzamide Chemical compound C1CC(N(C)C)CCN1C1=CC=C(N=C(N2)C(=O)C=3C=C(C(C(N)=O)=CC=3)C3=C(N(C)N=C3C)C)C2=N1 PKZOUEKXSHRMJY-UHFFFAOYSA-N 0.000 claims 1
- YYFYFLCAHGESSK-UHFFFAOYSA-N 4-[5-[4-(dimethylamino)piperidin-1-yl]-1h-imidazo[4,5-b]pyridine-2-carbonyl]-2-(1,6-naphthyridin-8-yl)benzonitrile Chemical compound C1CC(N(C)C)CCN1C1=CC=C(N=C(N2)C(=O)C=3C=C(C(C#N)=CC=3)C=3C4=NC=CC=C4C=NC=3)C2=N1 YYFYFLCAHGESSK-UHFFFAOYSA-N 0.000 claims 1
- UBZILCZVFAKCSH-UHFFFAOYSA-N 4-[5-[4-(dimethylamino)piperidin-1-yl]-1h-imidazo[4,5-b]pyridine-2-carbonyl]-2-(1h-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile Chemical compound C1CC(N(C)C)CCN1C1=CC=C(N=C(N2)C(=O)C=3C=C(C(C#N)=CC=3)C=3C=4C=CNC=4C=NC=3)C2=N1 UBZILCZVFAKCSH-UHFFFAOYSA-N 0.000 claims 1
- OHKLDPAMWXPTDV-UHFFFAOYSA-N 4-[5-[4-(dimethylamino)piperidin-1-yl]-1h-imidazo[4,5-b]pyridine-2-carbonyl]-2-(2-methyl-5,6-dihydro-4h-pyrrolo[1,2-b]pyrazol-3-yl)benzonitrile Chemical compound C1CC(N(C)C)CCN1C1=CC=C(N=C(N2)C(=O)C=3C=C(C(C#N)=CC=3)C3=C4CCCN4N=C3C)C2=N1 OHKLDPAMWXPTDV-UHFFFAOYSA-N 0.000 claims 1
- YWQBYRLLOJPSQF-UHFFFAOYSA-N 4-[5-[4-(dimethylamino)piperidin-1-yl]-1h-imidazo[4,5-b]pyridine-2-carbonyl]-2-(3,5-dimethyl-1h-pyrazol-4-yl)benzonitrile Chemical compound C1CC(N(C)C)CCN1C1=CC=C(N=C(N2)C(=O)C=3C=C(C(C#N)=CC=3)C3=C(NN=C3C)C)C2=N1 YWQBYRLLOJPSQF-UHFFFAOYSA-N 0.000 claims 1
- VNNWDTBGBTURRL-UHFFFAOYSA-N 4-[5-[4-(dimethylamino)piperidin-1-yl]-1h-imidazo[4,5-b]pyridine-2-carbonyl]-2-(5-methoxy-1h-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile Chemical compound COC1=NC=C2NC=CC2=C1C(C(=CC=1)C#N)=CC=1C(=O)C(NC1=N2)=NC1=CC=C2N1CCC(N(C)C)CC1 VNNWDTBGBTURRL-UHFFFAOYSA-N 0.000 claims 1
- AZXYPCBAGCXZPP-UHFFFAOYSA-N 4-[5-[4-(dimethylamino)piperidin-1-yl]-1h-imidazo[4,5-b]pyridine-2-carbonyl]-2-isoquinolin-4-ylbenzonitrile Chemical compound C1CC(N(C)C)CCN1C1=CC=C(N=C(N2)C(=O)C=3C=C(C(C#N)=CC=3)C=3C4=CC=CC=C4C=NC=3)C2=N1 AZXYPCBAGCXZPP-UHFFFAOYSA-N 0.000 claims 1
- CASXOABNUNPZDU-UHFFFAOYSA-N 4-[5-[4-(dimethylamino)piperidin-1-yl]-1h-imidazo[4,5-b]pyridine-2-carbonyl]-n,n-dimethyl-2-(1,3,5-trimethylpyrazol-4-yl)benzamide Chemical compound C1CC(N(C)C)CCN1C1=CC=C(N=C(N2)C(=O)C=3C=C(C(C(=O)N(C)C)=CC=3)C3=C(N(C)N=C3C)C)C2=N1 CASXOABNUNPZDU-UHFFFAOYSA-N 0.000 claims 1
- BHNKWBYHUQYDNL-UHFFFAOYSA-N 4-[6-[4-(dimethylamino)piperidin-1-yl]-1h-benzimidazole-2-carbonyl]-2-(1,6-naphthyridin-8-yl)benzonitrile Chemical compound C1CC(N(C)C)CCN1C1=CC=C(N=C(N2)C(=O)C=3C=C(C(C#N)=CC=3)C=3C4=NC=CC=C4C=NC=3)C2=C1 BHNKWBYHUQYDNL-UHFFFAOYSA-N 0.000 claims 1
- YSFRNDGQSYSMBC-UHFFFAOYSA-N 4-[6-[4-(dimethylamino)piperidin-1-yl]-1h-benzimidazole-2-carbonyl]-2-(1h-pyrrolo[2,3-c]pyridin-4-yl)benzonitrile Chemical compound C1CC(N(C)C)CCN1C1=CC=C(N=C(N2)C(=O)C=3C=C(C(C#N)=CC=3)C=3C=4C=CNC=4C=NC=3)C2=C1 YSFRNDGQSYSMBC-UHFFFAOYSA-N 0.000 claims 1
- KINUJJAJWRSOPG-UHFFFAOYSA-N 4-[6-[4-(dimethylamino)piperidin-1-yl]-1h-benzimidazole-2-carbonyl]-2-(3,5-dimethyl-1h-pyrazol-4-yl)benzonitrile Chemical compound C1CC(N(C)C)CCN1C1=CC=C(NC(=N2)C(=O)C=3C=C(C(C#N)=CC=3)C3=C(NN=C3C)C)C2=C1 KINUJJAJWRSOPG-UHFFFAOYSA-N 0.000 claims 1
- IZKOTEHTJHHWCW-UHFFFAOYSA-N 4-[6-[4-(dimethylamino)piperidin-1-yl]-1h-benzimidazole-2-carbonyl]-2-isoquinolin-4-ylbenzonitrile Chemical compound C1CC(N(C)C)CCN1C1=CC=C(N=C(N2)C(=O)C=3C=C(C(C#N)=CC=3)C=3C4=CC=CC=C4C=NC=3)C2=C1 IZKOTEHTJHHWCW-UHFFFAOYSA-N 0.000 claims 1
- LRETUTULBWLWJY-UHFFFAOYSA-N 4-[6-[4-(dimethylamino)piperidin-1-yl]-1h-benzimidazole-2-carbonyl]-2-pyridin-3-ylbenzonitrile Chemical compound C1CC(N(C)C)CCN1C1=CC=C(NC(=N2)C(=O)C=3C=C(C(C#N)=CC=3)C=3C=NC=CC=3)C2=C1 LRETUTULBWLWJY-UHFFFAOYSA-N 0.000 claims 1
- ANRFVQJNPUQBNQ-UHFFFAOYSA-N C1=NC=C(C2=CC=CC=C12)C1=NC=CC(=C1)C(=O)C=1NC2=C(N1)C=CC(=C2)C(=O)O.CN2CCC(CC2)NC(=O)C2=CC1=C(N=C(N1)C(=O)C1=CC(=NC=C1)C1=CN=CC3=CC=CC=C13)C=C2 Chemical compound C1=NC=C(C2=CC=CC=C12)C1=NC=CC(=C1)C(=O)C=1NC2=C(N1)C=CC(=C2)C(=O)O.CN2CCC(CC2)NC(=O)C2=CC1=C(N=C(N1)C(=O)C1=CC(=NC=C1)C1=CN=CC3=CC=CC=C13)C=C2 ANRFVQJNPUQBNQ-UHFFFAOYSA-N 0.000 claims 1
- 208000022072 Gallbladder Neoplasms Diseases 0.000 claims 1
- 208000007766 Kaposi sarcoma Diseases 0.000 claims 1
- 206010023347 Keratoacanthoma Diseases 0.000 claims 1
- 208000031671 Large B-Cell Diffuse Lymphoma Diseases 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- 208000025205 Mantle-Cell Lymphoma Diseases 0.000 claims 1
- GGOPPLRTQHXJOD-UHFFFAOYSA-N N1(CCNCCC1)C1=NC=C2N=C(NC2=N1)C(=O)C1=CC(=NC=C1)C1=CN=CC2=CC=CC=C12.CN(C1CCN(CC1)C1=NC=C2N=C(NC2=N1)C(=O)C1=CC(=NC=C1)C1=CN=CC2=CC=CC=C12)C Chemical compound N1(CCNCCC1)C1=NC=C2N=C(NC2=N1)C(=O)C1=CC(=NC=C1)C1=CN=CC2=CC=CC=C12.CN(C1CCN(CC1)C1=NC=C2N=C(NC2=N1)C(=O)C1=CC(=NC=C1)C1=CN=CC2=CC=CC=C12)C GGOPPLRTQHXJOD-UHFFFAOYSA-N 0.000 claims 1
- AKQIDEOPBDOBPH-UHFFFAOYSA-N OC(COC1=CC2=C(NC(=N2)C(=O)C2=CC(=NC=C2)C2=CN=CC3=CC=CC=C23)C=C1)CO.C1=NC=C(C2=CC=CC=C12)C1=NC=CC(=C1)C(=O)C1=NC2=C(N1)C=C(C=C2)C(=O)N2CCN(CC2)C Chemical compound OC(COC1=CC2=C(NC(=N2)C(=O)C2=CC(=NC=C2)C2=CN=CC3=CC=CC=C23)C=C1)CO.C1=NC=C(C2=CC=CC=C12)C1=NC=CC(=C1)C(=O)C1=NC2=C(N1)C=C(C=C2)C(=O)N2CCN(CC2)C AKQIDEOPBDOBPH-UHFFFAOYSA-N 0.000 claims 1
- 206010033128 Ovarian cancer Diseases 0.000 claims 1
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims 1
- POYXZUSWPDTCEZ-MHZLTWQESA-N [1-[2-[4-cyano-3-(1h-pyrrolo[2,3-c]pyridin-4-yl)benzoyl]-1h-imidazo[4,5-b]pyridin-5-yl]piperidin-4-yl] (2s)-2-amino-3-methylbutanoate Chemical compound C1CC(OC(=O)[C@@H](N)C(C)C)CCN1C1=CC=C(N=C(N2)C(=O)C=3C=C(C(C#N)=CC=3)C=3C=4C=CNC=4C=NC=3)C2=N1 POYXZUSWPDTCEZ-MHZLTWQESA-N 0.000 claims 1
- GELPAICLPBIPOL-UHFFFAOYSA-N [1-[2-[4-cyano-3-(1h-pyrrolo[2,3-c]pyridin-4-yl)benzoyl]-1h-imidazo[4,5-b]pyridin-5-yl]piperidin-4-yl] dihydrogen phosphate Chemical compound C1CC(OP(O)(=O)O)CCN1C1=CC=C(N=C(N2)C(=O)C=3C=C(C(C#N)=CC=3)C=3C=4C=CNC=4C=NC=3)C2=N1 GELPAICLPBIPOL-UHFFFAOYSA-N 0.000 claims 1
- GHZMACPPWOXDAF-UHFFFAOYSA-N [2-(2,3-difluoro-6-methoxyphenyl)pyridin-4-yl]-[5-[4-(dimethylamino)piperidin-1-yl]-1h-imidazo[4,5-b]pyridin-2-yl]methanone Chemical compound COC1=CC=C(F)C(F)=C1C1=CC(C(=O)C=2NC3=CC=C(N=C3N=2)N2CCC(CC2)N(C)C)=CC=N1 GHZMACPPWOXDAF-UHFFFAOYSA-N 0.000 claims 1
- POHLCTXEFNIAPD-UHFFFAOYSA-N [2-(2,3-difluoro-6-methoxyphenyl)pyridin-4-yl]-[6-(morpholin-4-ylmethyl)-1h-benzimidazol-2-yl]methanone Chemical compound COC1=CC=C(F)C(F)=C1C1=CC(C(=O)C=2NC3=CC=C(CN4CCOCC4)C=C3N=2)=CC=N1 POHLCTXEFNIAPD-UHFFFAOYSA-N 0.000 claims 1
- ZHACVGYKYWUETF-UHFFFAOYSA-N [2-(2,6-difluorophenyl)pyridin-4-yl]-[5-(1-methylpyrazol-4-yl)-1h-imidazol-2-yl]methanone Chemical compound C1=NN(C)C=C1C1=CN=C(C(=O)C=2C=C(N=CC=2)C=2C(=CC=CC=2F)F)N1 ZHACVGYKYWUETF-UHFFFAOYSA-N 0.000 claims 1
- JYMGLMLPGSJRJP-UHFFFAOYSA-N [2-(2-fluoro-6-methoxyphenyl)pyridin-4-yl]-[6-(4-methylpiperazin-1-yl)-1h-benzimidazol-2-yl]methanone Chemical compound COC1=CC=CC(F)=C1C1=CC(C(=O)C=2NC3=CC(=CC=C3N=2)N2CCN(C)CC2)=CC=N1 JYMGLMLPGSJRJP-UHFFFAOYSA-N 0.000 claims 1
- ICABARWOYMUEGC-UHFFFAOYSA-N [2-(2-fluoro-6-methoxyphenyl)pyridin-4-yl]-[6-(morpholin-4-ylmethyl)-1h-benzimidazol-2-yl]methanone Chemical compound COC1=CC=CC(F)=C1C1=CC(C(=O)C=2NC3=CC=C(CN4CCOCC4)C=C3N=2)=CC=N1 ICABARWOYMUEGC-UHFFFAOYSA-N 0.000 claims 1
- QQGLOTBFBBUOQN-UHFFFAOYSA-N [2-(2-methoxyphenyl)pyridin-4-yl]-[6-(morpholin-4-ylmethyl)-1h-benzimidazol-2-yl]methanone Chemical compound COC1=CC=CC=C1C1=CC(C(=O)C=2NC3=CC=C(CN4CCOCC4)C=C3N=2)=CC=N1 QQGLOTBFBBUOQN-UHFFFAOYSA-N 0.000 claims 1
- SCTPOSMZFADLDT-UHFFFAOYSA-N [2-(benzimidazol-1-yl)pyridin-4-yl]-[6-[4-(dimethylamino)piperidin-1-yl]-1h-benzimidazol-2-yl]methanone Chemical compound C1CC(N(C)C)CCN1C1=CC=C(N=C(N2)C(=O)C=3C=C(N=CC=3)N3C4=CC=CC=C4N=C3)C2=C1 SCTPOSMZFADLDT-UHFFFAOYSA-N 0.000 claims 1
- SWHVOLCMMMZWHU-UHFFFAOYSA-N [2-[4-(hydroxymethyl)phenyl]pyridin-4-yl]-[6-(morpholin-4-ylmethyl)-1h-benzimidazol-2-yl]methanone Chemical compound C1=CC(CO)=CC=C1C1=CC(C(=O)C=2NC3=CC=C(CN4CCOCC4)C=C3N=2)=CC=N1 SWHVOLCMMMZWHU-UHFFFAOYSA-N 0.000 claims 1
- SYKTYAPYHWVZFP-UHFFFAOYSA-N [3-(2-fluoro-6-methoxyphenyl)phenyl]-[6-(morpholin-4-ylmethyl)-1h-benzimidazol-2-yl]methanone Chemical compound COC1=CC=CC(F)=C1C1=CC=CC(C(=O)C=2NC3=CC=C(CN4CCOCC4)C=C3N=2)=C1 SYKTYAPYHWVZFP-UHFFFAOYSA-N 0.000 claims 1
- MEMMPNRCFBTOPD-UHFFFAOYSA-N [4-chloro-3-(2-methoxyphenyl)phenyl]-[6-[(dimethylamino)methyl]-1h-benzimidazol-2-yl]methanone Chemical compound COC1=CC=CC=C1C1=CC(C(=O)C=2NC3=CC=C(CN(C)C)C=C3N=2)=CC=C1Cl MEMMPNRCFBTOPD-UHFFFAOYSA-N 0.000 claims 1
- ZORNFEJUOXUUQB-UHFFFAOYSA-N [5-(1,4-diazepan-1-yl)-1h-imidazo[4,5-b]pyridin-2-yl]-(2-isoquinolin-4-ylpyridin-4-yl)methanone Chemical compound C=1C=NC(C=2C3=CC=CC=C3C=NC=2)=CC=1C(=O)C(NC1=N2)=NC1=CC=C2N1CCCNCC1 ZORNFEJUOXUUQB-UHFFFAOYSA-N 0.000 claims 1
- NUQHOJXVFHOPQP-UHFFFAOYSA-N [5-(1,4-diazepan-1-yl)-1h-imidazo[4,5-b]pyridin-2-yl]-[2-(3,5-dimethyl-1h-pyrazol-4-yl)pyridin-4-yl]methanone Chemical compound CC1=NNC(C)=C1C1=CC(C(=O)C=2NC3=NC(=CC=C3N=2)N2CCNCCC2)=CC=N1 NUQHOJXVFHOPQP-UHFFFAOYSA-N 0.000 claims 1
- QMLRTGRRMWDNLF-UHFFFAOYSA-N [5-(2,3-difluoro-6-methoxyphenyl)pyridin-3-yl]-[6-[(dimethylamino)methyl]-1h-benzimidazol-2-yl]methanone Chemical compound COC1=CC=C(F)C(F)=C1C1=CN=CC(C(=O)C=2NC3=CC=C(CN(C)C)C=C3N=2)=C1 QMLRTGRRMWDNLF-UHFFFAOYSA-N 0.000 claims 1
- VSHURSPEQITHNX-UHFFFAOYSA-N [5-[4-(dimethylamino)piperidin-1-yl]-1h-imidazo[4,5-b]pyridin-2-yl]-(2-isoquinolin-4-ylpyridin-4-yl)methanone Chemical compound C1CC(N(C)C)CCN1C1=CC=C(N=C(N2)C(=O)C=3C=C(N=CC=3)C=3C4=CC=CC=C4C=NC=3)C2=N1 VSHURSPEQITHNX-UHFFFAOYSA-N 0.000 claims 1
- WAFBWYMISKHOQF-UHFFFAOYSA-N [5-[4-(dimethylamino)piperidin-1-yl]-1h-imidazo[4,5-b]pyridin-2-yl]-[2-(1,3,5-trimethylpyrazol-4-yl)pyridin-4-yl]methanone Chemical compound C1CC(N(C)C)CCN1C1=CC=C(N=C(N2)C(=O)C=3C=C(N=CC=3)C3=C(N(C)N=C3C)C)C2=N1 WAFBWYMISKHOQF-UHFFFAOYSA-N 0.000 claims 1
- MGKFAGTZWMNNBL-UHFFFAOYSA-N [5-[4-(dimethylamino)piperidin-1-yl]-1h-imidazo[4,5-b]pyridin-2-yl]-[2-(3,5-dimethyl-1h-pyrazol-4-yl)pyridin-4-yl]methanone Chemical compound C1CC(N(C)C)CCN1C1=CC=C(N=C(N2)C(=O)C=3C=C(N=CC=3)C3=C(NN=C3C)C)C2=N1 MGKFAGTZWMNNBL-UHFFFAOYSA-N 0.000 claims 1
- QVQCCTONKGEBDU-UHFFFAOYSA-N [5-[[4-(dimethylamino)piperidin-1-yl]methyl]-1h-imidazol-2-yl]-[2-(2-fluoro-6-methoxyphenyl)pyridin-4-yl]methanone Chemical compound COC1=CC=CC(F)=C1C1=CC(C(=O)C=2NC=C(CN3CCC(CC3)N(C)C)N=2)=CC=N1 QVQCCTONKGEBDU-UHFFFAOYSA-N 0.000 claims 1
- BKBXBTTXDPREEK-UHFFFAOYSA-N [6-[4-(dimethylamino)piperidin-1-yl]-1H-benzimidazol-2-yl]-[2-(3,5-dimethyl-1H-pyrazol-4-yl)pyridin-4-yl]methanone formic acid Chemical compound OC=O.C1CC(N(C)C)CCN1C1=CC=C(N=C(N2)C(=O)C=3C=C(N=CC=3)C3=C(NN=C3C)C)C2=C1 BKBXBTTXDPREEK-UHFFFAOYSA-N 0.000 claims 1
- MOFMNWUBIGFTJG-UHFFFAOYSA-N [6-[4-(dimethylamino)piperidin-1-yl]-1h-benzimidazol-2-yl]-(2-imidazo[4,5-b]pyridin-1-ylpyridin-4-yl)methanone Chemical compound C1CC(N(C)C)CCN1C1=CC=C(N=C(N2)C(=O)C=3C=C(N=CC=3)N3C4=CC=CN=C4N=C3)C2=C1 MOFMNWUBIGFTJG-UHFFFAOYSA-N 0.000 claims 1
- JAXKKINYQHLFJQ-UHFFFAOYSA-N [6-[4-(dimethylamino)piperidin-1-yl]-1h-benzimidazol-2-yl]-(2-imidazo[4,5-b]pyridin-3-ylpyridin-4-yl)methanone Chemical compound C1CC(N(C)C)CCN1C1=CC=C(N=C(N2)C(=O)C=3C=C(N=CC=3)N3C4=NC=CC=C4N=C3)C2=C1 JAXKKINYQHLFJQ-UHFFFAOYSA-N 0.000 claims 1
- KBLNRFKWFDQCOH-UHFFFAOYSA-N [6-[4-(dimethylamino)piperidin-1-yl]-1h-benzimidazol-2-yl]-(2-imidazo[4,5-c]pyridin-1-ylpyridin-4-yl)methanone Chemical compound C1CC(N(C)C)CCN1C1=CC=C(N=C(N2)C(=O)C=3C=C(N=CC=3)N3C4=CC=NC=C4N=C3)C2=C1 KBLNRFKWFDQCOH-UHFFFAOYSA-N 0.000 claims 1
- LVJDDRKRMDYVGG-UHFFFAOYSA-N [6-[4-(dimethylamino)piperidin-1-yl]-1h-benzimidazol-2-yl]-(2-imidazo[4,5-c]pyridin-3-ylpyridin-4-yl)methanone Chemical compound C1CC(N(C)C)CCN1C1=CC=C(N=C(N2)C(=O)C=3C=C(N=CC=3)N3C4=CN=CC=C4N=C3)C2=C1 LVJDDRKRMDYVGG-UHFFFAOYSA-N 0.000 claims 1
- GANYPWUWUOBIFD-UHFFFAOYSA-N [6-[4-(dimethylamino)piperidin-1-yl]-1h-benzimidazol-2-yl]-(2-isoquinolin-4-ylpyridin-4-yl)methanone;hydrochloride Chemical compound Cl.C1CC(N(C)C)CCN1C1=CC=C(N=C(N2)C(=O)C=3C=C(N=CC=3)C=3C4=CC=CC=C4C=NC=3)C2=C1 GANYPWUWUOBIFD-UHFFFAOYSA-N 0.000 claims 1
- TZBFIXCVYSDUSL-UHFFFAOYSA-N [6-[4-(dimethylamino)piperidin-1-yl]-1h-benzimidazol-2-yl]-(2-naphthalen-1-ylpyridin-4-yl)methanone Chemical compound C1CC(N(C)C)CCN1C1=CC=C(N=C(N2)C(=O)C=3C=C(N=CC=3)C=3C4=CC=CC=C4C=CC=3)C2=C1 TZBFIXCVYSDUSL-UHFFFAOYSA-N 0.000 claims 1
- KADCBHAONKOVMP-UHFFFAOYSA-N [6-[4-(dimethylamino)piperidin-1-yl]-1h-benzimidazol-2-yl]-(2-quinolin-3-ylpyridin-4-yl)methanone Chemical compound C1CC(N(C)C)CCN1C1=CC=C(N=C(N2)C(=O)C=3C=C(N=CC=3)C=3C=C4C=CC=CC4=NC=3)C2=C1 KADCBHAONKOVMP-UHFFFAOYSA-N 0.000 claims 1
- KMIPCENMCPTFSM-UHFFFAOYSA-N [6-[4-(dimethylamino)piperidin-1-yl]-1h-benzimidazol-2-yl]-(3-isoquinolin-4-yl-4-methoxyphenyl)methanone Chemical compound C1=C(C=2C3=CC=CC=C3C=NC=2)C(OC)=CC=C1C(=O)C(NC1=C2)=NC1=CC=C2N1CCC(N(C)C)CC1 KMIPCENMCPTFSM-UHFFFAOYSA-N 0.000 claims 1
- GGUHGTXCHNVBAV-UHFFFAOYSA-N [6-[4-(dimethylamino)piperidin-1-yl]-1h-benzimidazol-2-yl]-(4-hydroxy-3-isoquinolin-4-ylphenyl)methanone Chemical compound C1CC(N(C)C)CCN1C1=CC=C(N=C(N2)C(=O)C=3C=C(C(O)=CC=3)C=3C4=CC=CC=C4C=NC=3)C2=C1 GGUHGTXCHNVBAV-UHFFFAOYSA-N 0.000 claims 1
- VHACBSGNRWYQOC-UHFFFAOYSA-N [6-[4-(dimethylamino)piperidin-1-yl]-1h-benzimidazol-2-yl]-[2-(1,5-dimethylpyrazol-4-yl)pyridin-4-yl]methanone Chemical compound C1CC(N(C)C)CCN1C1=CC=C(N=C(N2)C(=O)C=3C=C(N=CC=3)C3=C(N(C)N=C3)C)C2=C1 VHACBSGNRWYQOC-UHFFFAOYSA-N 0.000 claims 1
- ACPKIMZOKMUWKK-UHFFFAOYSA-N [6-[4-(dimethylamino)piperidin-1-yl]-1h-benzimidazol-2-yl]-[2-(2,4-dimethyl-1,3-thiazol-5-yl)pyridin-4-yl]methanone Chemical compound C1CC(N(C)C)CCN1C1=CC=C(N=C(N2)C(=O)C=3C=C(N=CC=3)C3=C(N=C(C)S3)C)C2=C1 ACPKIMZOKMUWKK-UHFFFAOYSA-N 0.000 claims 1
- DZRGXXMHDKOOOG-UHFFFAOYSA-N [6-[4-(dimethylamino)piperidin-1-yl]-1h-benzimidazol-2-yl]-[2-(2,4-dimethylimidazol-1-yl)pyridin-4-yl]methanone Chemical compound C1CC(N(C)C)CCN1C1=CC=C(N=C(N2)C(=O)C=3C=C(N=CC=3)N3C(=NC(C)=C3)C)C2=C1 DZRGXXMHDKOOOG-UHFFFAOYSA-N 0.000 claims 1
- PWGGBCYTAWYROK-UHFFFAOYSA-N [6-[4-(dimethylamino)piperidin-1-yl]-1h-benzimidazol-2-yl]-[2-(2,5-dimethylimidazol-1-yl)pyridin-4-yl]methanone Chemical compound C1CC(N(C)C)CCN1C1=CC=C(N=C(N2)C(=O)C=3C=C(N=CC=3)N3C(=NC=C3C)C)C2=C1 PWGGBCYTAWYROK-UHFFFAOYSA-N 0.000 claims 1
- KCOOVGMBJZHARI-UHFFFAOYSA-N [6-[4-(dimethylamino)piperidin-1-yl]-1h-benzimidazol-2-yl]-[2-(2-fluoro-6-methoxyphenyl)pyridin-4-yl]methanone Chemical compound COC1=CC=CC(F)=C1C1=CC(C(=O)C=2NC3=CC(=CC=C3N=2)N2CCC(CC2)N(C)C)=CC=N1 KCOOVGMBJZHARI-UHFFFAOYSA-N 0.000 claims 1
- YLCCDZZWUADAPM-UHFFFAOYSA-N [6-[4-(dimethylamino)piperidin-1-yl]-1h-benzimidazol-2-yl]-[2-(2-methylpyrazol-3-yl)pyridin-4-yl]methanone Chemical compound C1CC(N(C)C)CCN1C1=CC=C(N=C(N2)C(=O)C=3C=C(N=CC=3)C=3N(N=CC=3)C)C2=C1 YLCCDZZWUADAPM-UHFFFAOYSA-N 0.000 claims 1
- LPPHGFKBHIROMQ-UHFFFAOYSA-N [6-[4-(dimethylamino)piperidin-1-yl]-1h-benzimidazol-2-yl]-[2-(4-piperidin-1-ylphenyl)pyridin-4-yl]methanone Chemical compound C1CC(N(C)C)CCN1C1=CC=C(N=C(N2)C(=O)C=3C=C(N=CC=3)C=3C=CC(=CC=3)N3CCCCC3)C2=C1 LPPHGFKBHIROMQ-UHFFFAOYSA-N 0.000 claims 1
- ZZHRRFBGJUTZSM-UHFFFAOYSA-N [6-[4-(dimethylamino)piperidin-1-yl]-1h-benzimidazol-2-yl]-[2-(4-propan-2-ylpyrimidin-5-yl)pyridin-4-yl]methanone Chemical compound CC(C)C1=NC=NC=C1C1=CC(C(=O)C=2NC3=CC(=CC=C3N=2)N2CCC(CC2)N(C)C)=CC=N1 ZZHRRFBGJUTZSM-UHFFFAOYSA-N 0.000 claims 1
- UXNWVHSZNWPGAY-UHFFFAOYSA-N [6-[4-(dimethylamino)piperidin-1-yl]-1h-benzimidazol-2-yl]-[2-(5-fluoro-2-methoxyphenyl)pyridin-4-yl]methanone Chemical compound COC1=CC=C(F)C=C1C1=CC(C(=O)C=2NC3=CC(=CC=C3N=2)N2CCC(CC2)N(C)C)=CC=N1 UXNWVHSZNWPGAY-UHFFFAOYSA-N 0.000 claims 1
- 230000002159 abnormal effect Effects 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 230000003796 beauty Effects 0.000 claims 1
- 150000001555 benzenes Chemical group 0.000 claims 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 210000001185 bone marrow Anatomy 0.000 claims 1
- 230000004663 cell proliferation Effects 0.000 claims 1
- 201000010989 colorectal carcinoma Diseases 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 206010012818 diffuse large B-cell lymphoma Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 235000019253 formic acid Nutrition 0.000 claims 1
- 201000010175 gallbladder cancer Diseases 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- 206010024627 liposarcoma Diseases 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 230000003248 secreting effect Effects 0.000 claims 1
- 201000000849 skin cancer Diseases 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- YPFNWDCHTHUZJI-UHFFFAOYSA-N tert-butyl 4-[2-(2-isoquinolin-4-ylpyridine-4-carbonyl)-1h-imidazo[4,5-b]pyridin-5-yl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C1=CC=C(N=C(N2)C(=O)C=3C=C(N=CC=3)C=3C4=CC=CC=C4C=NC=3)C2=N1 YPFNWDCHTHUZJI-UHFFFAOYSA-N 0.000 claims 1
- VFMXFWKMRJHRET-UHFFFAOYSA-N tert-butyl 4-[2-(2-isoquinolin-4-ylpyridine-4-carbonyl)-1h-imidazo[4,5-b]pyridin-6-yl]-1,4-diazepane-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCCN1C1=CN=C(NC(=N2)C(=O)C=3C=C(N=CC=3)C=3C4=CC=CC=C4C=NC=3)C2=C1 VFMXFWKMRJHRET-UHFFFAOYSA-N 0.000 claims 1
- WDCGFXUFPDNXRY-UHFFFAOYSA-N tert-butyl 4-[2-(4-cyano-3-isoquinolin-4-ylbenzoyl)-1h-imidazo[4,5-b]pyridin-5-yl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C1=CC=C(N=C(N2)C(=O)C=3C=C(C(C#N)=CC=3)C=3C4=CC=CC=C4C=NC=3)C2=N1 WDCGFXUFPDNXRY-UHFFFAOYSA-N 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- MQSHJRDHJAXHCA-UHFFFAOYSA-N 2-(2-isoquinolin-4-ylpyridine-4-carbonyl)-n-methyl-n-piperidin-4-yl-3h-benzimidazole-5-carboxamide Chemical compound C=1C=C2N=C(C(=O)C=3C=C(N=CC=3)C=3C4=CC=CC=C4C=NC=3)NC2=CC=1C(=O)N(C)C1CCNCC1 MQSHJRDHJAXHCA-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 208000030901 thyroid gland follicular carcinoma Diseases 0.000 description 2
- QEJMSQXNOLMRQP-UHFFFAOYSA-N (2-isoquinolin-4-ylpyridin-4-yl)-(6-piperazin-1-ylsulfonyl-1h-benzimidazol-2-yl)methanone Chemical compound C=1C=NC(C=2C3=CC=CC=C3C=NC=2)=CC=1C(=O)C(NC1=C2)=NC1=CC=C2S(=O)(=O)N1CCNCC1 QEJMSQXNOLMRQP-UHFFFAOYSA-N 0.000 description 1
- XTJLXJJWHKJSKK-UHFFFAOYSA-N (2-isoquinolin-4-ylpyridin-4-yl)-[6-(4-methylpiperazine-1-carbonyl)-1h-benzimidazol-2-yl]methanone Chemical compound C1CN(C)CCN1C(=O)C1=CC=C(N=C(N2)C(=O)C=3C=C(N=CC=3)C=3C4=CC=CC=C4C=NC=3)C2=C1 XTJLXJJWHKJSKK-UHFFFAOYSA-N 0.000 description 1
- 0 *[C@](CC1)CN1C(CC1)=Nc2c1nc(C(c1ccnc(-c3cncc4c3cccc4)c1)=O)[n]2 Chemical compound *[C@](CC1)CN1C(CC1)=Nc2c1nc(C(c1ccnc(-c3cncc4c3cccc4)c1)=O)[n]2 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- OMSMEALWAYMUMV-UHFFFAOYSA-N 2-(2-isoquinolin-4-ylpyridine-4-carbonyl)-3h-benzimidazole-5-carboxylic acid Chemical compound C1=CC=C2C(C=3N=CC=C(C=3)C(=O)C3=NC4=CC=C(C=C4N3)C(=O)O)=CN=CC2=C1 OMSMEALWAYMUMV-UHFFFAOYSA-N 0.000 description 1
- CUWJNDQSCHRSLF-UHFFFAOYSA-N 2-(2-isoquinolin-4-ylpyridine-4-carbonyl)-n-(1-methylpiperidin-4-yl)-3h-benzimidazole-5-carboxamide Chemical compound C1CN(C)CCC1NC(=O)C1=CC=C(N=C(N2)C(=O)C=3C=C(N=CC=3)C=3C4=CC=CC=C4C=NC=3)C2=C1 CUWJNDQSCHRSLF-UHFFFAOYSA-N 0.000 description 1
- NHQNIRDQLWWOEA-UHFFFAOYSA-N 2-(3,5-dimethyl-1,2-oxazol-4-yl)-4-[6-(piperazine-1-carbonyl)-1h-benzimidazole-2-carbonyl]benzonitrile Chemical compound CC1=NOC(C)=C1C1=CC(C(=O)C=2NC3=CC(=CC=C3N=2)C(=O)N2CCNCC2)=CC=C1C#N NHQNIRDQLWWOEA-UHFFFAOYSA-N 0.000 description 1
- VXJSVATYJOKYHT-UHFFFAOYSA-N 2-(3,5-dimethyl-1-phenylpyrazol-4-yl)-4-[6-(piperazine-1-carbonyl)-1h-benzimidazole-2-carbonyl]benzonitrile Chemical compound CC1=NN(C=2C=CC=CC=2)C(C)=C1C(C(=CC=1)C#N)=CC=1C(=O)C(NC1=C2)=NC1=CC=C2C(=O)N1CCNCC1 VXJSVATYJOKYHT-UHFFFAOYSA-N 0.000 description 1
- GVEWCANTZKBWQZ-UHFFFAOYSA-N 2-isoquinolin-4-yl-4-[6-(piperazine-1-carbonyl)-1h-benzimidazole-2-carbonyl]benzonitrile Chemical compound C=1C=C2N=C(C(=O)C=3C=C(C(C#N)=CC=3)C=3C4=CC=CC=C4C=NC=3)NC2=CC=1C(=O)N1CCNCC1 GVEWCANTZKBWQZ-UHFFFAOYSA-N 0.000 description 1
- SDNULCBXKUDCSQ-UHFFFAOYSA-N 4-(5,6-dimethoxy-1h-benzimidazole-2-carbonyl)-2-[5-(ethylaminomethyl)pyridin-3-yl]benzonitrile Chemical compound CCNCC1=CN=CC(C=2C(=CC=C(C=2)C(=O)C=2NC3=CC(OC)=C(OC)C=C3N=2)C#N)=C1 SDNULCBXKUDCSQ-UHFFFAOYSA-N 0.000 description 1
- HCEVVNFSRNCYJU-UHFFFAOYSA-N 4-(6-chloro-1h-benzimidazole-2-carbonyl)-2-(1,6-naphthyridin-8-yl)benzonitrile Chemical compound C1=CN=C2C(C=3C(C#N)=CC=C(C=3)C(=O)C3=NC4=CC=C(C=C4N3)Cl)=CN=CC2=C1 HCEVVNFSRNCYJU-UHFFFAOYSA-N 0.000 description 1
- ZBCJILZMCZKXJJ-UHFFFAOYSA-N 4-[6-(piperazine-1-carbonyl)-1h-benzimidazole-2-carbonyl]-2-(1,3,5-trimethylpyrazol-4-yl)benzonitrile Chemical compound CC1=NN(C)C(C)=C1C1=CC(C(=O)C=2NC3=CC(=CC=C3N=2)C(=O)N2CCNCC2)=CC=C1C#N ZBCJILZMCZKXJJ-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- MMLRULFBXCZLBE-QDTIIGTASA-N C/N=C\C(CC1)CN1c(cc1)nc2c1nc(C(c1ccnc(-c3cncc4c3cccc4)c1)O)[nH]2 Chemical compound C/N=C\C(CC1)CN1c(cc1)nc2c1nc(C(c1ccnc(-c3cncc4c3cccc4)c1)O)[nH]2 MMLRULFBXCZLBE-QDTIIGTASA-N 0.000 description 1
- 206010048832 Colon adenoma Diseases 0.000 description 1
- 208000004463 Follicular Adenocarcinoma Diseases 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- JGCVUYFJASRLET-UHFFFAOYSA-N [6-(2,3-dihydroxypropoxy)-1h-benzimidazol-2-yl]-(2-isoquinolin-4-ylpyridin-4-yl)methanone Chemical compound C1=CC=C2C(C=3N=CC=C(C=3)C(=O)C=3NC4=CC=C(C=C4N=3)OCC(O)CO)=CN=CC2=C1 JGCVUYFJASRLET-UHFFFAOYSA-N 0.000 description 1
- TYJIOHIPDUAMJD-UHFFFAOYSA-N [6-(piperazine-1-carbonyl)-1h-benzimidazol-2-yl]-[2-(1,3,5-trimethylpyrazol-4-yl)pyridin-4-yl]methanone Chemical compound CC1=NN(C)C(C)=C1C1=CC(C(=O)C=2NC3=CC(=CC=C3N=2)C(=O)N2CCNCC2)=CC=N1 TYJIOHIPDUAMJD-UHFFFAOYSA-N 0.000 description 1
- AZSVOSUWSANYIN-UHFFFAOYSA-N [6-[4-(dimethylamino)piperidin-1-yl]-1h-benzimidazol-2-yl]-(2-methylpyridin-4-yl)methanone Chemical compound C1CC(N(C)C)CCN1C1=CC=C(N=C(N2)C(=O)C=3C=C(C)N=CC=3)C2=C1 AZSVOSUWSANYIN-UHFFFAOYSA-N 0.000 description 1
- APDOILJMYTVJQL-UHFFFAOYSA-N [6-[4-(dimethylamino)piperidin-1-yl]-1h-benzimidazol-2-yl]-(2-pyrazolo[1,5-a]pyridin-3-ylpyridin-4-yl)methanone Chemical compound C1CC(N(C)C)CCN1C1=CC=C(N=C(N2)C(=O)C=3C=C(N=CC=3)C3=C4C=CC=CN4N=C3)C2=C1 APDOILJMYTVJQL-UHFFFAOYSA-N 0.000 description 1
- 201000007455 central nervous system cancer Diseases 0.000 description 1
- 208000025997 central nervous system neoplasm Diseases 0.000 description 1
- 201000010897 colon adenocarcinoma Diseases 0.000 description 1
- 210000003238 esophagus Anatomy 0.000 description 1
- 210000000232 gallbladder Anatomy 0.000 description 1
- 238000004896 high resolution mass spectrometry Methods 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- 201000001441 melanoma Diseases 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- AMMXGROYYKHVQZ-UHFFFAOYSA-N n-(2-aminoethyl)-2-(4-cyano-3-isoquinolin-4-ylbenzoyl)-n-methyl-3h-benzimidazole-5-sulfonamide Chemical compound C1=CC=C2C(C=3C(C#N)=CC=C(C=3)C(=O)C3=NC4=CC=C(C=C4N3)S(=O)(=O)N(CCN)C)=CN=CC2=C1 AMMXGROYYKHVQZ-UHFFFAOYSA-N 0.000 description 1
- 210000001672 ovary Anatomy 0.000 description 1
- 210000000496 pancreas Anatomy 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- CZYUGTLMFHDODF-UHFFFAOYSA-N tert-butyl 4-(methylamino)piperidine-1-carboxylate Chemical compound CNC1CCN(C(=O)OC(C)(C)C)CC1 CZYUGTLMFHDODF-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US17429309P | 2009-04-30 | 2009-04-30 | |
| US61/174,293 | 2009-04-30 | ||
| PCT/GB2010/050725 WO2010125402A1 (en) | 2009-04-30 | 2010-04-30 | Imidazole derivatives and their use as modulators of cyclin dependent kinases |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2012525367A JP2012525367A (ja) | 2012-10-22 |
| JP2012525367A5 true JP2012525367A5 (enExample) | 2014-10-02 |
Family
ID=42315726
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012507826A Ceased JP2012525367A (ja) | 2009-04-30 | 2010-04-30 | イミダゾール誘導体およびサイクリン依存性キナーゼ類のモジュレーターとしてのその使用 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US8598217B2 (enExample) |
| EP (1) | EP2424843B1 (enExample) |
| JP (1) | JP2012525367A (enExample) |
| KR (1) | KR20120004542A (enExample) |
| CN (1) | CN102803225A (enExample) |
| AU (1) | AU2010243353B2 (enExample) |
| BR (1) | BRPI1016190A2 (enExample) |
| CA (1) | CA2759083A1 (enExample) |
| EA (1) | EA020017B1 (enExample) |
| ES (1) | ES2458872T3 (enExample) |
| MX (1) | MX2011011516A (enExample) |
| PL (1) | PL2424843T3 (enExample) |
| PT (1) | PT2424843E (enExample) |
| WO (1) | WO2010125402A1 (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2689177T3 (es) | 2010-04-13 | 2018-11-08 | Novartis Ag | Combinación que comprende un inhibidor de cinasa 4 dependiente de ciclina o cinasa dependiente de ciclina (CDK4/6) y un inhibidor de mTOR para tratar cáncer |
| CN103476258B (zh) * | 2011-02-25 | 2017-04-26 | 默沙东公司 | 用作抗糖尿病药剂的新的环状氮杂苯并咪唑衍生物 |
| WO2013033085A1 (en) * | 2011-08-30 | 2013-03-07 | Stephen Martin Courtney | Kynurenine-3-monooxygenase inhibitors, pharmaceutical compositions, and methods of use thereof |
| WO2013139734A1 (de) * | 2012-03-21 | 2013-09-26 | Bayer Intellectual Property Gmbh | Verwendung von (rs)-s-cyclopropyl-s-(4-{[4-{[(1r, 2r)-2-hydroxy-1-methylpropyl]oxy}-5-(trifluormethyl)pyrimidin-2-yl]amino}phenyl)sulfoximid zur behandlung spezifischer tumore |
| AU2013245353A1 (en) * | 2012-04-06 | 2014-09-25 | Pfizer Inc. | Diacylglycerol acyltransferase 2 inhibitors |
| JP6084292B2 (ja) | 2013-07-18 | 2017-02-22 | 大鵬薬品工業株式会社 | Ｆｇｆｒ阻害剤耐性癌の治療薬 |
| KR101974254B1 (ko) | 2013-07-18 | 2019-04-30 | 다이호야쿠힌고교 가부시키가이샤 | Fgfr 저해제의 간헐 투여용 항종양제 |
| US10258621B2 (en) | 2014-07-17 | 2019-04-16 | Chdi Foundation, Inc. | Methods and compositions for treating HIV-related disorders |
| KR101917557B1 (ko) | 2015-03-31 | 2018-11-09 | 다이호야쿠힌고교 가부시키가이샤 | 3,5-2치환 벤젠알키닐 화합물의 결정 |
| CN105218459B (zh) * | 2015-11-03 | 2019-02-15 | 广东电网有限责任公司电力科学研究院 | 苯并咪唑类金属钝化剂及其制备方法和应用 |
| WO2017091373A1 (en) * | 2015-11-25 | 2017-06-01 | Patheon Development Services Inc. | Amorphous dispersion granules and oral dosage forms |
| KR20250007056A (ko) | 2016-03-04 | 2025-01-13 | 다이호야쿠힌고교 가부시키가이샤 | 악성 종양 치료용 제제 및 조성물 |
| US11883404B2 (en) | 2016-03-04 | 2024-01-30 | Taiho Pharmaceuticals Co., Ltd. | Preparation and composition for treatment of malignant tumors |
| KR102700664B1 (ko) * | 2017-08-07 | 2024-08-29 | 조인트 스탁 컴퍼니 “바이오케드” | Cdk8/19 저해제로서 새로운 헤테로사이클릭 화합물 |
| SG11202008435SA (en) | 2018-03-19 | 2020-10-29 | Taiho Pharmaceutical Co Ltd | Pharmaceutical composition including sodium alkyl sulfate |
| KR102906523B1 (ko) | 2018-09-13 | 2025-12-30 | 브리스톨-마이어스 스큅 컴퍼니 | 수용체-상호작용 단백질 키나제 1 (ripk1) 억제제로서의 1h-인다졸 카르복스아미드 |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05331163A (ja) | 1991-03-26 | 1993-12-14 | Kumiai Chem Ind Co Ltd | ピリジン誘導体及び除草剤 |
| DE4142075A1 (de) | 1991-12-19 | 1993-06-24 | Hoechst Ag | Carbocyclische fuenfringverbindungen, verfahren zu ihrer herstellung und ihre verwendung als pharmazeutika |
| JP3217848B2 (ja) | 1992-03-25 | 2001-10-15 | クミアイ化学工業株式会社 | ピリジン誘導体及び除草剤 |
| PL341984A1 (en) | 1998-01-28 | 2001-05-07 | Shionogi & Co | Novel tricycle compounds |
| JP4295458B2 (ja) | 1999-06-30 | 2009-07-15 | アムジェン インコーポレイテッド | Ｐｐａｒ−ガンマ活性調節用化合物 |
| BR0012984A (pt) | 1999-08-04 | 2002-07-16 | Millennium Pharm Inc | Método para tratar um estado associado com o mc4-r em um mamìfero, composto de ligação ao mc4-r, e, composição farmacêutica |
| DE60131138T2 (de) | 2000-01-13 | 2008-08-14 | Amgen Inc., Thousand Oaks | Antibakterielle mittel |
| WO2002000647A1 (en) | 2000-06-23 | 2002-01-03 | Bristol-Myers Squibb Pharma Company | Heteroaryl-phenyl substituted factor xa inhibitors |
| WO2002062766A2 (en) | 2001-02-07 | 2002-08-15 | Millennium Pharmaceuticals, Inc. | Melanocortin-4 receptor binding compounds and methods of use thereof |
| US6603000B2 (en) | 2001-07-11 | 2003-08-05 | Boehringer Ingelheim Pharmaceuticals, Inc. | Synthesis for heteroarylamine compounds |
| GB0311276D0 (en) * | 2003-05-16 | 2003-06-18 | Astrazeneca Ab | Chemical compounds |
| US7504401B2 (en) | 2003-08-29 | 2009-03-17 | Locus Pharmaceuticals, Inc. | Anti-cancer agents and uses thereof |
| DE10354060A1 (de) | 2003-11-19 | 2005-06-02 | Merck Patent Gmbh | Pyrrolderivate |
| RU2006124843A (ru) | 2003-12-12 | 2008-01-20 | Уайт (Us) | Хинолины, пригодные для лечения сердечно-сосудистого заболевания |
| EP1730118A1 (en) | 2004-02-12 | 2006-12-13 | Transtech Pharma, Inc. | Substituted azole derivatives, compositions, and methods of use |
| AU2007209381A1 (en) * | 2006-01-27 | 2007-08-02 | F. Hoffmann-La Roche Ag | Use of substituted 2-imidazole of imidazoline derivatives |
| WO2008013963A2 (en) | 2006-07-28 | 2008-01-31 | University Of Connecticut | Fatty acid amide hydrolase inhibitors |
| US8883790B2 (en) * | 2006-10-12 | 2014-11-11 | Astex Therapeutics Limited | Pharmaceutical combinations |
| AU2008279776B2 (en) * | 2007-07-19 | 2013-05-23 | Merck Sharp & Dohme Corp. | Heterocyclic amide compounds as protein kinase inhibitors |
-
2010
- 2010-04-30 MX MX2011011516A patent/MX2011011516A/es active IP Right Grant
- 2010-04-30 EA EA201101566A patent/EA020017B1/ru not_active IP Right Cessation
- 2010-04-30 EP EP10719772.5A patent/EP2424843B1/en active Active
- 2010-04-30 PT PT107197725T patent/PT2424843E/pt unknown
- 2010-04-30 KR KR1020117028530A patent/KR20120004542A/ko not_active Withdrawn
- 2010-04-30 ES ES10719772.5T patent/ES2458872T3/es active Active
- 2010-04-30 JP JP2012507826A patent/JP2012525367A/ja not_active Ceased
- 2010-04-30 US US13/266,976 patent/US8598217B2/en not_active Expired - Fee Related
- 2010-04-30 WO PCT/GB2010/050725 patent/WO2010125402A1/en not_active Ceased
- 2010-04-30 BR BRPI1016190A patent/BRPI1016190A2/pt not_active IP Right Cessation
- 2010-04-30 AU AU2010243353A patent/AU2010243353B2/en not_active Expired - Fee Related
- 2010-04-30 CN CN201080029384XA patent/CN102803225A/zh active Pending
- 2010-04-30 PL PL10719772T patent/PL2424843T3/pl unknown
- 2010-04-30 CA CA2759083A patent/CA2759083A1/en not_active Abandoned
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2012525367A5 (enExample) | ||
| US11485745B2 (en) | Amido spirocyclic amide and sulfonamide derivatives | |
| AU2018201903B2 (en) | SUBSTITUTED N-(1H-INDAZOL-4-YL)IMIDAZO[1,2-a]PYRIDINE-3-CARBOXAMIDE COMPOUNDS AS TYPE III RECEPTOR TYROSINE KINASE INHIBITORS | |
| JP6876833B2 (ja) | Ｆｇｆｒ阻害剤およびその使用 | |
| CA2515197C (en) | Pyrazolopyridine derivates | |
| RS55045B1 (sr) | Biciklična heterociklična jedinjenja kao inhibitori tirozin kinaze proteina | |
| KR20180134983A (ko) | Ret 키나아제 억제제로서의 헤테로사이클릭 화합물 | |
| JP2008508358A (ja) | アリール−アミノ置換ピロロピリミジンマルチキナーゼ阻害化合物 | |
| CA3050827A1 (en) | Aryl hydrocarbon receptor (ahr) modulator compounds | |
| CN115557933B (zh) | 布鲁顿酪氨酸激酶及其突变体降解剂、组合物及应用 | |
| CN114945571A (zh) | 环状化合物及其使用方法 | |
| WO2021211741A1 (en) | Substituted pyridines for the treatment of inflammatory diseases | |
| JP2013511501A (ja) | ピリジノピリジノン誘導体、その調製および治療用途 | |
| JP7716777B2 (ja) | 窒素含有多環式縮合環系化合物、その医薬組成物、製造方法及び用途 | |
| JP2020530020A (ja) | Ｃｄｋ８／１９阻害薬としての新規ヘテロ環式化合物 | |
| CA3105010A1 (en) | 4-substituted pyrrolo[2,3-b]pyridine as erbb modulators useful for treating cancer | |
| AU2014284013B2 (en) | Five-membered heterocyclic pyridine compounds and preparation method and use thereof | |
| CN116490503A (zh) | 酪蛋白激酶1δ调节剂 | |
| TW202510868A (zh) | 新穎吡唑并吡啶衍生物 | |
| HK40109089A (zh) | 酰胺类化合物及其用途 | |
| HK40104416A (zh) | 酰胺类化合物及其用途 | |
| HK40105207A (zh) | 酰胺类化合物及其用途 | |
| WO2021165497A1 (en) | 2,3,5-substituted pyrrolo[2,3-b]pyridines as erbb modulators useful for treating cancer | |
| HK40095637A (zh) | 杂芳环类化合物及其用途 | |
| ES2558839T3 (es) | Derivados de aminas tricíclicas como inhibidores de la proteína tirosina quinasa |