JP2012525367A5 - - Google Patents
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- 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
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- -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
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| 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 |
| AU2004298486A1 (en) | 2003-12-12 | 2005-06-30 | Wyeth | Quinolines useful in treating cardiovascular disease |
| CA2551909C (en) | 2004-02-12 | 2011-10-11 | Transtech Pharma, Inc. | Substituted azole derivatives, compositions, and methods of use |
| CA2637312A1 (en) * | 2006-01-27 | 2007-08-02 | F. Hoffmann-La Roche Ag | Use of substituted 2-imidazole of imidazoline derivatives |
| EP2051964A4 (en) | 2006-07-28 | 2012-03-07 | Univ Connecticut | INHIBITORS OF FATTY ACID AMIDHYDROLASE |
| EP2073807A1 (en) * | 2006-10-12 | 2009-07-01 | Astex Therapeutics Limited | Pharmaceutical combinations |
| MY150032A (en) * | 2007-07-19 | 2013-11-29 | Merck Sharp & Dohme | Heterocyclic amide compounds as protein kinase inhibitors |
-
2010
- 2010-04-30 CA CA2759083A patent/CA2759083A1/en not_active Abandoned
- 2010-04-30 US US13/266,976 patent/US8598217B2/en not_active Expired - Fee Related
- 2010-04-30 CN CN201080029384XA patent/CN102803225A/zh active Pending
- 2010-04-30 JP JP2012507826A patent/JP2012525367A/ja not_active Ceased
- 2010-04-30 EA EA201101566A patent/EA020017B1/ru not_active IP Right Cessation
- 2010-04-30 PT PT107197725T patent/PT2424843E/pt unknown
- 2010-04-30 ES ES10719772.5T patent/ES2458872T3/es active Active
- 2010-04-30 MX MX2011011516A patent/MX2011011516A/es active IP Right Grant
- 2010-04-30 PL PL10719772T patent/PL2424843T3/pl unknown
- 2010-04-30 AU AU2010243353A patent/AU2010243353B2/en not_active Expired - Fee Related
- 2010-04-30 EP EP10719772.5A patent/EP2424843B1/en active Active
- 2010-04-30 KR KR1020117028530A patent/KR20120004542A/ko not_active Withdrawn
- 2010-04-30 BR BRPI1016190A patent/BRPI1016190A2/pt not_active IP Right Cessation
- 2010-04-30 WO PCT/GB2010/050725 patent/WO2010125402A1/en not_active Ceased
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