JP2016513656A5 - - Google Patents

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Publication number

JP2016513656A5

JP2016513656A5 JP2016502156A JP2016502156A JP2016513656A5 JP 2016513656 A5 JP2016513656 A5 JP 2016513656A5 JP 2016502156 A JP2016502156 A JP 2016502156A JP 2016502156 A JP2016502156 A JP 2016502156A JP 2016513656 A5 JP2016513656 A5 JP 2016513656A5

Authority

JP

Japan

Prior art keywords

substituted

heterocycle

alkyl

aryl

cycloalkyl

Prior art date

2014-03-13

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

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• 150000001875 compounds Chemical class 0.000 claims description 664
• 125000000623 heterocyclic group Chemical group 0.000 claims description 658
• 125000000217 alkyl group Chemical group 0.000 claims description 342
• 125000003118 aryl group Chemical group 0.000 claims description 335
• 229910052739 hydrogen Inorganic materials 0.000 claims description 316
• 239000001257 hydrogen Substances 0.000 claims description 316
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 309
• 150000002431 hydrogen Chemical class 0.000 claims description 290
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 279
• 125000003107 substituted aryl group Chemical group 0.000 claims description 271
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 270
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 239
• 229910052799 carbon Inorganic materials 0.000 claims description 157
• 150000002367 halogens Chemical class 0.000 claims description 153
• 229910052736 halogen Inorganic materials 0.000 claims description 152
• 125000003342 alkenyl group Chemical group 0.000 claims description 136
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 136
• 125000000304 alkynyl group Chemical group 0.000 claims description 135
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 133
• 125000005017 substituted alkenyl group Chemical group 0.000 claims description 129
• 125000004426 substituted alkynyl group Chemical group 0.000 claims description 129
• 125000004953 trihalomethyl group Chemical group 0.000 claims description 107
• SQQWBSBBCSFQGC-JLHYYAGUSA-N ubiquinone-2 Chemical compound COC1=C(OC)C(=O)C(C\C=C(/C)CCC=C(C)C)=C(C)C1=O SQQWBSBBCSFQGC-JLHYYAGUSA-N 0.000 claims description 94
• 206010028980 Neoplasm Diseases 0.000 claims description 71
• 150000003839 salts Chemical class 0.000 claims description 64
• 201000011510 cancer Diseases 0.000 claims description 63
• -1 pyridyl compound Chemical class 0.000 claims description 62
• 125000001424 substituent group Chemical group 0.000 claims description 52
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 51
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 50
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 45
• 238000000034 method Methods 0.000 claims description 45
• 239000000203 mixture Substances 0.000 claims description 44
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 42
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 37
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 32
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 32
• 102000001253 Protein Kinase Human genes 0.000 claims description 30
• 208000035475 disorder Diseases 0.000 claims description 30
• 108060006633 protein kinase Proteins 0.000 claims description 30
• 239000000651 prodrug Substances 0.000 claims description 29
• 229940002612 prodrug Drugs 0.000 claims description 29
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 28
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 26
• 125000005842 heteroatom Chemical group 0.000 claims description 26
• 210000000130 stem cell Anatomy 0.000 claims description 26
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
• 229910052698 phosphorus Inorganic materials 0.000 claims description 23
• 239000012453 solvate Substances 0.000 claims description 23
• 150000002148 esters Chemical class 0.000 claims description 22
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 20
• 241000124008 Mammalia Species 0.000 claims description 19
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 18
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 18
• XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 18
• 229910052717 sulfur Inorganic materials 0.000 claims description 17
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 16
• IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 16
• 229910052760 oxygen Inorganic materials 0.000 claims description 16
• 125000003386 piperidinyl group Chemical group 0.000 claims description 16
• 229930192474 thiophene Natural products 0.000 claims description 14
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 13
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 13
• JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 claims description 13
• 230000002401 inhibitory effect Effects 0.000 claims description 13
• 125000003545 alkoxy group Chemical group 0.000 claims description 12
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 12
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 12
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 11
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 11
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 11
• 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 11
• 125000004076 pyridyl group Chemical group 0.000 claims description 11
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 10
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 10
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
• 125000001072 heteroaryl group Chemical group 0.000 claims description 10
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 10
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 10
• AMFYRKOUWBAGHV-UHFFFAOYSA-N 1h-pyrazolo[4,3-b]pyridine Chemical compound C1=CN=C2C=NNC2=C1 AMFYRKOUWBAGHV-UHFFFAOYSA-N 0.000 claims description 9
• GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 claims description 9
• MJQSRSOTRPMVKB-UHFFFAOYSA-N 5h-imidazo[4,5-c]pyridazine Chemical compound C1=NNC2=NC=NC2=C1 MJQSRSOTRPMVKB-UHFFFAOYSA-N 0.000 claims description 9
• ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 9
• OGEBRHQLRGFBNV-RZDIXWSQSA-N chembl2036808 Chemical compound C12=NC(NCCCC)=NC=C2C(C=2C=CC(F)=CC=2)=NN1C[C@H]1CC[C@H](N)CC1 OGEBRHQLRGFBNV-RZDIXWSQSA-N 0.000 claims description 9
• 239000003085 diluting agent Substances 0.000 claims description 9
• IJAPPYDYQCXOEF-UHFFFAOYSA-N phthalazin-1(2H)-one Chemical compound C1=CC=C2C(=O)NN=CC2=C1 IJAPPYDYQCXOEF-UHFFFAOYSA-N 0.000 claims description 9
• JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims description 9
• VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 9
• BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims description 8
• 239000003937 drug carrier Substances 0.000 claims description 8
• 230000004083 survival effect Effects 0.000 claims description 8
• DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 7
• ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 7
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
• ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 7
• CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 7
• LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 claims description 7
• 125000002950 monocyclic group Chemical group 0.000 claims description 7
• WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 7
• UHHKSVZZTYJVEG-UHFFFAOYSA-N oxepane Chemical compound C1CCCOCC1 UHHKSVZZTYJVEG-UHFFFAOYSA-N 0.000 claims description 7
• UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims description 7
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 7
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 7
• 150000003852 triazoles Chemical class 0.000 claims description 7
• 229910052720 vanadium Inorganic materials 0.000 claims description 7
• 230000000694 effects Effects 0.000 claims description 6
• 230000035755 proliferation Effects 0.000 claims description 6
• 125000001544 thienyl group Chemical group 0.000 claims description 6
• PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 5
• 102000009516 Protein Serine-Threonine Kinases Human genes 0.000 claims description 5
• 108010009341 Protein Serine-Threonine Kinases Proteins 0.000 claims description 5
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 5
• 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 5
• 102000037979 non-receptor tyrosine kinases Human genes 0.000 claims description 5
• 108091008046 non-receptor tyrosine kinases Proteins 0.000 claims description 5
• PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 5
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 5
• 102000027426 receptor tyrosine kinases Human genes 0.000 claims description 5
• 108091008598 receptor tyrosine kinases Proteins 0.000 claims description 5
• 230000002829 reductive effect Effects 0.000 claims description 4
• 230000008685 targeting Effects 0.000 claims description 4
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 4
• 208000031261 Acute myeloid leukaemia Diseases 0.000 claims description 3
• 206010003571 Astrocytoma Diseases 0.000 claims description 3
• 208000023275 Autoimmune disease Diseases 0.000 claims description 3
• 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims description 3
• 206010005003 Bladder cancer Diseases 0.000 claims description 3
• 206010006187 Breast cancer Diseases 0.000 claims description 3
• 208000026310 Breast neoplasm Diseases 0.000 claims description 3
• 208000024172 Cardiovascular disease Diseases 0.000 claims description 3
• 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims description 3
• 206010009944 Colon cancer Diseases 0.000 claims description 3
• 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 3
• 206010016654 Fibrosis Diseases 0.000 claims description 3
• 206010017993 Gastrointestinal neoplasms Diseases 0.000 claims description 3
• 206010051066 Gastrointestinal stromal tumour Diseases 0.000 claims description 3
• 208000032612 Glial tumor Diseases 0.000 claims description 3
• 206010018338 Glioma Diseases 0.000 claims description 3
• 208000017604 Hodgkin disease Diseases 0.000 claims description 3
• 208000021519 Hodgkin lymphoma Diseases 0.000 claims description 3
• 208000010747 Hodgkins lymphoma Diseases 0.000 claims description 3
• 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 3
• 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims description 3
• 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims description 3
• 208000014767 Myeloproliferative disease Diseases 0.000 claims description 3
• 201000007224 Myeloproliferative neoplasm Diseases 0.000 claims description 3
• 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims description 3
• 206010033128 Ovarian cancer Diseases 0.000 claims description 3
• 206010061535 Ovarian neoplasm Diseases 0.000 claims description 3
• 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 3
• 206010060862 Prostate cancer Diseases 0.000 claims description 3
• 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 3
• 201000004681 Psoriasis Diseases 0.000 claims description 3
• 208000006265 Renal cell carcinoma Diseases 0.000 claims description 3
• 206010041067 Small cell lung cancer Diseases 0.000 claims description 3
• 208000005718 Stomach Neoplasms Diseases 0.000 claims description 3
• 208000024770 Thyroid neoplasm Diseases 0.000 claims description 3
• 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 3
• 230000033115 angiogenesis Effects 0.000 claims description 3
• 125000003725 azepanyl group Chemical group 0.000 claims description 3
• 230000003197 catalytic effect Effects 0.000 claims description 3
• 230000005754 cellular signaling Effects 0.000 claims description 3
• 206010012601 diabetes mellitus Diseases 0.000 claims description 3
• 230000004761 fibrosis Effects 0.000 claims description 3
• 206010017758 gastric cancer Diseases 0.000 claims description 3
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• 208000005017 glioblastoma Diseases 0.000 claims description 3
• 201000010536 head and neck cancer Diseases 0.000 claims description 3
• 208000014829 head and neck neoplasm Diseases 0.000 claims description 3
• 206010073071 hepatocellular carcinoma Diseases 0.000 claims description 3
• 230000003463 hyperproliferative effect Effects 0.000 claims description 3
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• 208000020816 lung neoplasm Diseases 0.000 claims description 3
• 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 3
• 201000001441 melanoma Diseases 0.000 claims description 3
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
• 230000004770 neurodegeneration Effects 0.000 claims description 3
• 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 3
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• 125000003551 oxepanyl group Chemical group 0.000 claims description 3
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• 210000000603 stem cell niche Anatomy 0.000 claims description 3
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• 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims description 3
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• 208000008385 Urogenital Neoplasms Diseases 0.000 claims description 2
• 208000037964 urogenital cancer Diseases 0.000 claims description 2
• LMQPOBXTKNSKDQ-UHFFFAOYSA-N 1,3-benzothiazole 1H-indazole Chemical compound S1C=NC2=C1C=CC=C2.N2N=CC1=C2C=CC=C1 LMQPOBXTKNSKDQ-UHFFFAOYSA-N 0.000 claims 1
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• 229910052757 nitrogen Inorganic materials 0.000 description 98
• 229920000728 polyester Polymers 0.000 description 93
• 239000002904 solvent Substances 0.000 description 39
• 238000002360 preparation method Methods 0.000 description 27
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 26
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• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 20
• 238000006243 chemical reaction Methods 0.000 description 20
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
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• YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 16
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 14
• 210000004027 cell Anatomy 0.000 description 14
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