JP2008505167A - 医薬組成物 - Google Patents

Info

Publication number

JP2008505167A

JP2008505167A JP2007519872A JP2007519872A JP2008505167A JP 2008505167 A JP2008505167 A JP 2008505167A JP 2007519872 A JP2007519872 A JP 2007519872A JP 2007519872 A JP2007519872 A JP 2007519872A JP 2008505167 A JP2008505167 A JP 2008505167A

Authority

JP

Japan

Prior art keywords

hydrogen

group

groups

compound

carbocyclic

Prior art date

2004-07-05

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.)

Withdrawn

Links

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• 239000008194 pharmaceutical composition Substances 0.000 title claims description 7
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 350
• 239000001257 hydrogen Substances 0.000 claims abstract description 348
• 150000001875 compounds Chemical class 0.000 claims abstract description 312
• 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 197
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 155
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 139
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 108
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 78
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 70
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 66
• 102000002254 Glycogen Synthase Kinase 3 Human genes 0.000 claims abstract description 55
• 108010014905 Glycogen Synthase Kinase 3 Proteins 0.000 claims abstract description 55
• 201000011510 cancer Diseases 0.000 claims abstract description 48
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 41
• 230000000694 effects Effects 0.000 claims abstract description 41
• 238000011282 treatment Methods 0.000 claims abstract description 37
• 150000003839 salts Chemical class 0.000 claims abstract description 36
• 150000001204 N-oxides Chemical class 0.000 claims abstract description 21
• 108091000080 Phosphotransferase Proteins 0.000 claims abstract description 19
• 102000020233 phosphotransferase Human genes 0.000 claims abstract description 19
• 239000012453 solvate Substances 0.000 claims abstract description 16
• 230000001404 mediated effect Effects 0.000 claims abstract description 12
• 125000003226 pyrazolyl group Chemical group 0.000 claims abstract description 5
• 150000002431 hydrogen Chemical class 0.000 claims abstract 48
• -1 cyano, nitro, carboxy, amino Chemical group 0.000 claims description 322
• 125000000623 heterocyclic group Chemical group 0.000 claims description 238
• 125000002837 carbocyclic group Chemical group 0.000 claims description 170
• 125000001424 substituent group Chemical group 0.000 claims description 168
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 150
• 229910052736 halogen Inorganic materials 0.000 claims description 125
• 150000002367 halogens Chemical class 0.000 claims description 118
• 125000003118 aryl group Chemical group 0.000 claims description 74
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 68
• 125000004432 carbon atom Chemical group C* 0.000 claims description 63
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 63
• 125000005842 heteroatom Chemical group 0.000 claims description 62
• 102000003903 Cyclin-dependent kinases Human genes 0.000 claims description 61
• 108090000266 Cyclin-dependent kinases Proteins 0.000 claims description 61
• 229910002091 carbon monoxide Inorganic materials 0.000 claims description 61
• 125000001072 heteroaryl group Chemical group 0.000 claims description 61
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 60
• 238000000034 method Methods 0.000 claims description 59
• 125000000217 alkyl group Chemical group 0.000 claims description 58
• 229910052799 carbon Inorganic materials 0.000 claims description 53
• 229910052731 fluorine Inorganic materials 0.000 claims description 53
• 102000003989 Aurora kinases Human genes 0.000 claims description 52
• 108090000433 Aurora kinases Proteins 0.000 claims description 52
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 49
• 239000011737 fluorine Substances 0.000 claims description 49
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 44
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 42
• 125000004043 oxo group Chemical group O=* 0.000 claims description 37
• NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 37
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 35
• 239000000460 chlorine Substances 0.000 claims description 33
• 230000001419 dependent effect Effects 0.000 claims description 32
• 201000010099 disease Diseases 0.000 claims description 31
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 31
• 125000002619 bicyclic group Chemical group 0.000 claims description 30
• 229910052801 chlorine Inorganic materials 0.000 claims description 29
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 26
• 125000004122 cyclic group Chemical group 0.000 claims description 26
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 25
• DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 25
• 125000002950 monocyclic group Chemical group 0.000 claims description 25
• 108090000461 Aurora Kinase A Proteins 0.000 claims description 23
• 108091007914 CDKs Proteins 0.000 claims description 21
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 21
• 230000002265 prevention Effects 0.000 claims description 21
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 19
• 239000003814 drug Substances 0.000 claims description 19
• 102000004000 Aurora Kinase A Human genes 0.000 claims description 18
• 206010006187 Breast cancer Diseases 0.000 claims description 18
• 125000004423 acyloxy group Chemical group 0.000 claims description 18
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 18
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 17
• 230000002401 inhibitory effect Effects 0.000 claims description 17
• 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 16
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 16
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 16
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 15
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 15
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
• 150000002148 esters Chemical class 0.000 claims description 15
• 108090000749 Aurora kinase B Proteins 0.000 claims description 14
• 230000003827 upregulation Effects 0.000 claims description 14
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 13
• 206010009944 Colon cancer Diseases 0.000 claims description 13
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 13
• 230000002159 abnormal effect Effects 0.000 claims description 13
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 13
• WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 claims description 13
• 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 12
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 12
• 208000026310 Breast neoplasm Diseases 0.000 claims description 12
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 12
• PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 claims description 12
• 102000004228 Aurora kinase B Human genes 0.000 claims description 11
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 11
• 230000010261 cell growth Effects 0.000 claims description 11
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 11
• 238000004519 manufacturing process Methods 0.000 claims description 11
• 208000024891 symptom Diseases 0.000 claims description 11
• KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 claims description 10
• 241000124008 Mammalia Species 0.000 claims description 10
• 206010033128 Ovarian cancer Diseases 0.000 claims description 10
• 206010061535 Ovarian neoplasm Diseases 0.000 claims description 10
• 125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 9
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 9
• 125000002883 imidazolyl group Chemical group 0.000 claims description 9
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 9
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 9
• XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 9
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 8
• 230000004770 neurodegeneration Effects 0.000 claims description 8
• 208000015122 neurodegenerative disease Diseases 0.000 claims description 8
• 125000002971 oxazolyl group Chemical group 0.000 claims description 8
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 7
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
• 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 7
• 125000001041 indolyl group Chemical group 0.000 claims description 7
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 7
• 230000002062 proliferating effect Effects 0.000 claims description 7
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 7
• 125000001544 thienyl group Chemical group 0.000 claims description 7
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 6
• KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 6
• 206010060862 Prostate cancer Diseases 0.000 claims description 6
• 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 6
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 6
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 6
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
• IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 6
• VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical compound C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 claims description 6
• AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 6
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 6
• 239000001301 oxygen Chemical group 0.000 claims description 6
• 230000001575 pathological effect Effects 0.000 claims description 6
• 125000006239 protecting group Chemical group 0.000 claims description 6
• 230000009467 reduction Effects 0.000 claims description 6
• FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 claims description 5
• FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 5
• AMFYRKOUWBAGHV-UHFFFAOYSA-N 1h-pyrazolo[4,3-b]pyridine Chemical compound C1=CN=C2C=NNC2=C1 AMFYRKOUWBAGHV-UHFFFAOYSA-N 0.000 claims description 5
• 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 5
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 5
• 208000023275 Autoimmune disease Diseases 0.000 claims description 5
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
• ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 5
• 208000036142 Viral infection Diseases 0.000 claims description 5
• 239000002168 alkylating agent Substances 0.000 claims description 5
• 229940100198 alkylating agent Drugs 0.000 claims description 5
• BNBQRQQYDMDJAH-UHFFFAOYSA-N benzodioxan Chemical compound C1=CC=C2OCCOC2=C1 BNBQRQQYDMDJAH-UHFFFAOYSA-N 0.000 claims description 5
• 125000002541 furyl group Chemical group 0.000 claims description 5
• CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 5
• 125000003386 piperidinyl group Chemical group 0.000 claims description 5
• PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 5
• 125000004076 pyridyl group Chemical group 0.000 claims description 5
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 5
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• 230000009385 viral infection Effects 0.000 claims description 5
• UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 claims description 4
• LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 claims description 4
• JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 4
• TVSMLBGFGKLKOO-UHFFFAOYSA-N 1,4-dimethylpiperidine Chemical compound CC1CCN(C)CC1 TVSMLBGFGKLKOO-UHFFFAOYSA-N 0.000 claims description 4
• HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 4
• 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims description 4
• HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical compound C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 claims description 4
• 101150012716 CDK1 gene Proteins 0.000 claims description 4
• 101100059559 Emericella nidulans (strain FGSC A4 / ATCC 38163 / CBS 112.46 / NRRL 194 / M139) nimX gene Proteins 0.000 claims description 4
• 208000000461 Esophageal Neoplasms Diseases 0.000 claims description 4
• 206010030155 Oesophageal carcinoma Diseases 0.000 claims description 4
• PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 4
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 4
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• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 4
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 4
• ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 4
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• 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims description 4
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• BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims description 3
• VMLKTERJLVWEJJ-UHFFFAOYSA-N 1,5-naphthyridine Chemical compound C1=CC=NC2=CC=CN=C21 VMLKTERJLVWEJJ-UHFFFAOYSA-N 0.000 claims description 3
• FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 claims description 3
• BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims description 3
• MFJCPDOGFAYSTF-UHFFFAOYSA-N 1H-isochromene Chemical compound C1=CC=C2COC=CC2=C1 MFJCPDOGFAYSTF-UHFFFAOYSA-N 0.000 claims description 3
• UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical compound C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 claims description 3
• RGNFMQJLAOONTP-UHFFFAOYSA-N 2-ethylmorpholine Chemical compound CCC1CNCCO1 RGNFMQJLAOONTP-UHFFFAOYSA-N 0.000 claims description 3
• VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 claims description 3
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• WPWNEKFMGCWNPR-UHFFFAOYSA-N 3,4-dihydro-2h-thiochromene Chemical compound C1=CC=C2CCCSC2=C1 WPWNEKFMGCWNPR-UHFFFAOYSA-N 0.000 claims description 3
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• 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
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• QZHPTGXQGDFGEN-UHFFFAOYSA-N chromene Chemical compound C1=CC=C2C=C[CH]OC2=C1 QZHPTGXQGDFGEN-UHFFFAOYSA-N 0.000 claims description 3
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• HEBMCVBCEDMUOF-UHFFFAOYSA-N isochromane Chemical compound C1=CC=C2COCCC2=C1 HEBMCVBCEDMUOF-UHFFFAOYSA-N 0.000 claims description 3
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• JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims description 3
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• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 2
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• 208000036765 Squamous cell carcinoma of the esophagus Diseases 0.000 claims description 2
• RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims description 2
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• 125000001153 fluoro group Chemical group F* 0.000 claims description 2
• 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 2
• 229940043355 kinase inhibitor Drugs 0.000 claims description 2
• 125000001624 naphthyl group Chemical group 0.000 claims description 2
• 239000003757 phosphotransferase inhibitor Substances 0.000 claims description 2
• 150000003254 radicals Chemical class 0.000 claims description 2
• 238000006467 substitution reaction Methods 0.000 claims description 2
• 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 2
• CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims description 2
• 241001465754 Metazoa Species 0.000 claims 3
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