JPWO2021097352A5 - - Google Patents
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- JPWO2021097352A5 JPWO2021097352A5 JP2022527677A JP2022527677A JPWO2021097352A5 JP WO2021097352 A5 JPWO2021097352 A5 JP WO2021097352A5 JP 2022527677 A JP2022527677 A JP 2022527677A JP 2022527677 A JP2022527677 A JP 2022527677A JP WO2021097352 A5 JPWO2021097352 A5 JP WO2021097352A5
- Authority
- JP
- Japan
- Prior art keywords
- compound according
- cancer
- section
- amine
- isoxazol
- 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.)
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- 150000001875 compounds Chemical class 0.000 claims description 145
- -1 methoxy, trifluoromethyloxy, difluoromethyloxy, ethoxy Chemical group 0.000 claims description 62
- 125000005843 halogen group Chemical group 0.000 claims description 32
- 206010028980 Neoplasm Diseases 0.000 claims description 30
- 201000011510 cancer Diseases 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- 125000003545 alkoxy group Chemical group 0.000 claims description 23
- 125000000623 heterocyclic group Chemical group 0.000 claims description 23
- 125000003342 alkenyl group Chemical group 0.000 claims description 18
- 125000000304 alkynyl group Chemical group 0.000 claims description 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 13
- 125000004414 alkyl thio group Chemical group 0.000 claims description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
- 150000002148 esters Chemical class 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 125000002252 acyl group Chemical group 0.000 claims description 9
- 125000003368 amide group Chemical group 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 claims description 9
- 229940124530 sulfonamide Drugs 0.000 claims description 9
- 150000003456 sulfonamides Chemical class 0.000 claims description 9
- 150000007970 thio esters Chemical class 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 206010006187 Breast cancer Diseases 0.000 claims description 6
- 208000026310 Breast neoplasm Diseases 0.000 claims description 6
- 206010009944 Colon cancer Diseases 0.000 claims description 6
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 6
- 208000029742 colonic neoplasm Diseases 0.000 claims description 6
- 201000005202 lung cancer Diseases 0.000 claims description 6
- 208000020816 lung neoplasm Diseases 0.000 claims description 6
- 201000001441 melanoma Diseases 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 208000008839 Kidney Neoplasms Diseases 0.000 claims description 5
- 206010033128 Ovarian cancer Diseases 0.000 claims description 5
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 5
- 206010060862 Prostate cancer Diseases 0.000 claims description 5
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 5
- 206010038389 Renal cancer Diseases 0.000 claims description 5
- 201000007455 central nervous system cancer Diseases 0.000 claims description 5
- 201000010982 kidney cancer Diseases 0.000 claims description 5
- 208000032839 leukemia Diseases 0.000 claims description 5
- DYMRYCZRMAHYKE-UHFFFAOYSA-N n-diazonitramide Chemical compound [O-][N+](=O)N=[N+]=[N-] DYMRYCZRMAHYKE-UHFFFAOYSA-N 0.000 claims description 5
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 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
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 4
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 125000005505 thiomorpholino group Chemical group 0.000 claims description 4
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 2
- 125000002393 azetidinyl group Chemical group 0.000 claims description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000004494 ethyl ester group Chemical group 0.000 claims description 2
- 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000004193 piperazinyl group Chemical group 0.000 claims description 2
- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 38
- 238000000034 method Methods 0.000 description 24
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 13
- IAXWZYXUKABJAN-UHFFFAOYSA-N 1,2-oxazol-5-amine Chemical compound NC1=CC=NO1 IAXWZYXUKABJAN-UHFFFAOYSA-N 0.000 description 8
- 101000836150 Homo sapiens Transforming acidic coiled-coil-containing protein 3 Proteins 0.000 description 8
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 8
- 102100027048 Transforming acidic coiled-coil-containing protein 3 Human genes 0.000 description 8
- 239000002246 antineoplastic agent Substances 0.000 description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 8
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 208000035475 disorder Diseases 0.000 description 4
- 230000001404 mediated effect Effects 0.000 description 4
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 229910000510 noble metal Inorganic materials 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 239000012453 solvate Substances 0.000 description 3
- MNILDQSRDHCFJG-UHFFFAOYSA-N 3-oxa-8-azabicyclo[3.2.1]octane Chemical compound C1OCC2CCC1N2 MNILDQSRDHCFJG-UHFFFAOYSA-N 0.000 description 2
- MJOUJKDTBGXKIU-UHFFFAOYSA-N 4,4-difluoropiperidine Chemical compound FC1(F)CCNCC1 MJOUJKDTBGXKIU-UHFFFAOYSA-N 0.000 description 2
- RDRQUUWCJTYHCT-UHFFFAOYSA-N 4-(trifluoromethyl)piperidine Chemical compound FC(F)(F)C1CCNCC1 RDRQUUWCJTYHCT-UHFFFAOYSA-N 0.000 description 2
- QBLLOOKBLTTXHB-UHFFFAOYSA-N 4-fluoropiperidine Chemical compound FC1CCNCC1 QBLLOOKBLTTXHB-UHFFFAOYSA-N 0.000 description 2
- UZOFELREXGAFOI-UHFFFAOYSA-N 4-methylpiperidine Chemical compound CC1CCNCC1 UZOFELREXGAFOI-UHFFFAOYSA-N 0.000 description 2
- POOPWPIOIMBTOH-UHFFFAOYSA-N 8-oxa-3-azabicyclo[3.2.1]octane Chemical compound C1NCC2CCC1O2 POOPWPIOIMBTOH-UHFFFAOYSA-N 0.000 description 2
- 230000005778 DNA damage Effects 0.000 description 2
- 231100000277 DNA damage Toxicity 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000006907 apoptotic process Effects 0.000 description 2
- 150000004678 hydrides Chemical class 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 229960005235 piperonyl butoxide Drugs 0.000 description 2
- 125000004591 piperonyl group Chemical group C(C1=CC=2OCOC2C=C1)* 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- DIQOUXNTSMWQSA-RFZPGFLSSA-N (1r,4r)-2-oxa-5-azabicyclo[2.2.1]heptane Chemical compound C1O[C@@]2([H])CN[C@]1([H])C2 DIQOUXNTSMWQSA-RFZPGFLSSA-N 0.000 description 1
- DIQOUXNTSMWQSA-WHFBIAKZSA-N (1s,4s)-2-oxa-5-azabicyclo[2.2.1]heptane Chemical compound C1O[C@]2([H])CN[C@@]1([H])C2 DIQOUXNTSMWQSA-WHFBIAKZSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- NDOVLWQBFFJETK-UHFFFAOYSA-N 1,4-thiazinane 1,1-dioxide Chemical compound O=S1(=O)CCNCC1 NDOVLWQBFFJETK-UHFFFAOYSA-N 0.000 description 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- HNVIQLPOGUDBSU-UHFFFAOYSA-N 2,6-dimethylmorpholine Chemical compound CC1CNCC(C)O1 HNVIQLPOGUDBSU-UHFFFAOYSA-N 0.000 description 1
- SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 description 1
- WFCSWCVEJLETKA-UHFFFAOYSA-N 2-piperazin-1-ylethanol Chemical compound OCCN1CCNCC1 WFCSWCVEJLETKA-UHFFFAOYSA-N 0.000 description 1
- LDSQQXKSEFZAPE-UHFFFAOYSA-N 2-piperidin-4-ylethanol Chemical compound OCCC1CCNCC1 LDSQQXKSEFZAPE-UHFFFAOYSA-N 0.000 description 1
- WRCGBYNVBFVRTN-UHFFFAOYSA-N 3-(4-methoxyphenyl)-N-(2-morpholin-4-ylpyrimidin-4-yl)-1,2-oxazol-5-amine Chemical compound COC1=CC=C(C=C1)C1=NOC(=C1)NC1=NC(=NC=C1)N1CCOCC1 WRCGBYNVBFVRTN-UHFFFAOYSA-N 0.000 description 1
- OTSKFVNQNDDFIG-UHFFFAOYSA-N C12CCCC(N1C1=NC=CC(=N1)NC1=CC(=NO1)C1=C(C=C(C=C1)OC)F)C2 Chemical compound C12CCCC(N1C1=NC=CC(=N1)NC1=CC(=NO1)C1=C(C=C(C=C1)OC)F)C2 OTSKFVNQNDDFIG-UHFFFAOYSA-N 0.000 description 1
- KGQGGFUEKBVCCT-UHFFFAOYSA-N C12OCC(N(C1)C1=NC=CC(=N1)NC1=CC(=NO1)C1=C(C=C(C=C1)OC)F)CC2 Chemical compound C12OCC(N(C1)C1=NC=CC(=N1)NC1=CC(=NO1)C1=C(C=C(C=C1)OC)F)CC2 KGQGGFUEKBVCCT-UHFFFAOYSA-N 0.000 description 1
- RFWVZBKPPZPCKV-UHFFFAOYSA-N C1CCC11CN(CCC1)C1=NC=CC(=N1)NC1=CC(=NO1)C1=C(C=C(C=C1)OC)F Chemical compound C1CCC11CN(CCC1)C1=NC=CC(=N1)NC1=CC(=NO1)C1=C(C=C(C=C1)OC)F RFWVZBKPPZPCKV-UHFFFAOYSA-N 0.000 description 1
- HGBJCBVVNXONCL-UHFFFAOYSA-N C1OCC11CN(CC1)C1=NC=CC(=N1)NC1=CC(=NO1)C1=C(C=C(C=C1)OC)F Chemical compound C1OCC11CN(CC1)C1=NC=CC(=N1)NC1=CC(=NO1)C1=C(C=C(C=C1)OC)F HGBJCBVVNXONCL-UHFFFAOYSA-N 0.000 description 1
- PZLVVZIESJSJGI-UHFFFAOYSA-N C1OCCC11CCN(CC1)C1=NC=CC(=N1)NC1=CC(=NO1)C1=C(C=C(C=C1)OC)F Chemical compound C1OCCC11CCN(CC1)C1=NC=CC(=N1)NC1=CC(=NO1)C1=C(C=C(C=C1)OC)F PZLVVZIESJSJGI-UHFFFAOYSA-N 0.000 description 1
- HYIWZHUYFSADOX-UHFFFAOYSA-N CCC(CN(C1=CC(C(C=C2)=CC=C2OC)=NO1)C1=NC(N2CCOCC2)=NC=C1)NCC Chemical compound CCC(CN(C1=CC(C(C=C2)=CC=C2OC)=NO1)C1=NC(N2CCOCC2)=NC=C1)NCC HYIWZHUYFSADOX-UHFFFAOYSA-N 0.000 description 1
- IZDRBFOBPZLFQW-UHFFFAOYSA-N COC(C=C1)=CC=C1C1=NOC(C2(N)NC(NC3CCOCC3)=NC=C2)=C1 Chemical compound COC(C=C1)=CC=C1C1=NOC(C2(N)NC(NC3CCOCC3)=NC=C2)=C1 IZDRBFOBPZLFQW-UHFFFAOYSA-N 0.000 description 1
- KYGPZMIMZZDEKF-UHFFFAOYSA-N COC(C=C1)=CC=C1C1=NOC(NC2=NC(CC(F)F)(N)NC=C2)=C1 Chemical compound COC(C=C1)=CC=C1C1=NOC(NC2=NC(CC(F)F)(N)NC=C2)=C1 KYGPZMIMZZDEKF-UHFFFAOYSA-N 0.000 description 1
- XAWCRELBHRBNOC-UHFFFAOYSA-N COC1=CC(=C(C=C1)C2=NOC(=C2)NC3=NC(=NC=C3)N4CC5CC(C4)O5)F Chemical compound COC1=CC(=C(C=C1)C2=NOC(=C2)NC3=NC(=NC=C3)N4CC5CC(C4)O5)F XAWCRELBHRBNOC-UHFFFAOYSA-N 0.000 description 1
- ZSQXSFVLRCSRQD-UHFFFAOYSA-N FC1=C(C=CC(=C1)OC)C1=NOC(=C1)NC1=NC(=NC=C1)N1C(COCC1)C(F)(F)F Chemical compound FC1=C(C=CC(=C1)OC)C1=NOC(=C1)NC1=NC(=NC=C1)N1C(COCC1)C(F)(F)F ZSQXSFVLRCSRQD-UHFFFAOYSA-N 0.000 description 1
- MTEWRTOFIAOTEG-UHFFFAOYSA-N FC1=C(C=CC(=C1)OC)C1=NOC(=C1)NC1=NC(=NC=C1)N1CC(OCC1)C Chemical compound FC1=C(C=CC(=C1)OC)C1=NOC(=C1)NC1=NC(=NC=C1)N1CC(OCC1)C MTEWRTOFIAOTEG-UHFFFAOYSA-N 0.000 description 1
- XPPBEODOULXEDO-UHFFFAOYSA-N FC1=C(C=CC(=C1)OC)C1=NOC(=C1)NC1=NC(=NC=C1)N1CC2C(C1)COC2 Chemical compound FC1=C(C=CC(=C1)OC)C1=NOC(=C1)NC1=NC(=NC=C1)N1CC2C(C1)COC2 XPPBEODOULXEDO-UHFFFAOYSA-N 0.000 description 1
- WDGSIOVDPABOMT-UHFFFAOYSA-N FC=1C=C(C=CC=1OC)C1=NOC(=C1)NC1=NC(=NC=C1)N1CCC(CC1)C Chemical compound FC=1C=C(C=CC=1OC)C1=NOC(=C1)NC1=NC(=NC=C1)N1CCC(CC1)C WDGSIOVDPABOMT-UHFFFAOYSA-N 0.000 description 1
- 206010027476 Metastases Diseases 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical group CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- LXNAVEXFUKBNMK-UHFFFAOYSA-N acetic acid;palladium Chemical compound [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 150000003973 alkyl amines Chemical group 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 230000005907 cancer growth Effects 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006001 difluoroethyl group Chemical group 0.000 description 1
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- RUJPPJYDHHAEEK-UHFFFAOYSA-N ethyl piperidine-4-carboxylate Chemical compound CCOC(=O)C1CCNCC1 RUJPPJYDHHAEEK-UHFFFAOYSA-N 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- SRJOCJYGOFTFLH-UHFFFAOYSA-N isonipecotic acid Chemical compound OC(=O)C1CCNCC1 SRJOCJYGOFTFLH-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 230000009401 metastasis Effects 0.000 description 1
- 230000011278 mitosis Effects 0.000 description 1
- 230000036456 mitotic arrest Effects 0.000 description 1
- 230000000394 mitotic effect Effects 0.000 description 1
- MKQLBNJQQZRQJU-UHFFFAOYSA-N morpholin-4-amine Chemical compound NN1CCOCC1 MKQLBNJQQZRQJU-UHFFFAOYSA-N 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 231100000590 oncogenic Toxicity 0.000 description 1
- 230000002246 oncogenic effect Effects 0.000 description 1
- AHVQYHFYQWKUKB-UHFFFAOYSA-N oxan-4-amine Chemical compound NC1CCOCC1 AHVQYHFYQWKUKB-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- LWMPFIOTEAXAGV-UHFFFAOYSA-N piperidin-1-amine Chemical compound NN1CCCCC1 LWMPFIOTEAXAGV-UHFFFAOYSA-N 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 229940121649 protein inhibitor Drugs 0.000 description 1
- 239000012268 protein inhibitor Substances 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000002626 targeted therapy Methods 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP19209120 | 2019-11-14 | ||
| EP19209120.5 | 2019-11-14 | ||
| PCT/US2020/060588 WO2021097352A1 (fr) | 2019-11-14 | 2020-11-13 | Dérivés d'isoxazole ciblant tacc3 en tant qu'agents anticancéreux |
Publications (2)
| Publication Number | Publication Date |
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| JP2023502602A JP2023502602A (ja) | 2023-01-25 |
| JPWO2021097352A5 true JPWO2021097352A5 (fr) | 2023-11-21 |
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| JP2022527677A Pending JP2023502602A (ja) | 2019-11-14 | 2020-11-13 | 抗がん剤としてｔａｃｃ３を標的とするイソオキサゾール誘導体 |
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|---|---|
| US (1) | US20230027854A1 (fr) |
| EP (1) | EP4058447A4 (fr) |
| JP (1) | JP2023502602A (fr) |
| KR (1) | KR20220103744A (fr) |
| CN (1) | CN115279754A (fr) |
| WO (1) | WO2021097352A1 (fr) |
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| TW202400575A (zh) | 2022-03-24 | 2024-01-01 | 美商Ａ２Ａ製藥公司 | 治療癌症的組合物和方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7115617B2 (en) * | 2001-08-22 | 2006-10-03 | Amgen Inc. | Amino-substituted pyrimidinyl derivatives and methods of use |
| EP1904065A2 (fr) * | 2005-07-14 | 2008-04-02 | AB Science | Utilisation d'inhibiteurs combines c-kit/fgfr3 pour le traitement du myelome multiple |
| EP2552214A4 (fr) * | 2010-03-26 | 2013-10-16 | Glaxo Group Ltd | Pyrazolyl-pyrimidines utilisés en tant qu'inhibiteurs de kinase |
| EP3801529B1 (fr) * | 2018-05-25 | 2023-10-11 | OncoCube Therapeutics LLC | Inhibiteur de tacc3 très puissant en tant que nouveau médicament candidat anticancéreux |
-
2020
- 2020-11-13 WO PCT/US2020/060588 patent/WO2021097352A1/fr unknown
- 2020-11-13 JP JP2022527677A patent/JP2023502602A/ja active Pending
- 2020-11-13 EP EP20888312.4A patent/EP4058447A4/fr active Pending
- 2020-11-13 KR KR1020227020047A patent/KR20220103744A/ko active Search and Examination
- 2020-11-13 US US17/776,767 patent/US20230027854A1/en active Pending
- 2020-11-13 CN CN202080091759.9A patent/CN115279754A/zh active Pending
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