JP2018504415A5

JP2018504415A5 -

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Publication number: JP2018504415A5
Authority: JP; Japan
Prior art keywords: phenyl; methyl; oxazol; ethoxymethyl; pyrazol
Prior art date: 2016-02-05
Legal status : Granted

Application number

JP2017539023A

Other languages

English (en)

Japanese (ja)

Other versions

JP6713000B2 (ja

JP2018504415A (ja

Filing date

2016-02-05

Publication date

2019-03-07

2015-02-05 Priority claimed from EP15154028.3A external-priority patent/EP3053920B1/en

2016-02-05 Application filed filed Critical

2018-02-15 Publication of JP2018504415A publication Critical patent/JP2018504415A/ja

2019-03-07 Publication of JP2018504415A5 publication Critical patent/JP2018504415A5/ja

2020-06-24 Application granted granted Critical

2020-06-24 Publication of JP6713000B2 publication Critical patent/JP6713000B2/ja

Status Active legal-status Critical Current

2036-02-05 Anticipated expiration legal-status Critical

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150000001875 compounds Chemical class 0.000 claims description 194
-1 1,2-diazinyl Chemical group 0.000 claims description 88
239000001257 hydrogen Substances 0.000 claims description 60
229910052739 hydrogen Inorganic materials 0.000 claims description 60
125000000217 alkyl group Chemical group 0.000 claims description 59
150000003839 salts Chemical class 0.000 claims description 54
230000003381 solubilizing effect Effects 0.000 claims description 43
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 42
125000000623 heterocyclic group Chemical group 0.000 claims description 42
201000010099 disease Diseases 0.000 claims description 40
125000001072 heteroaryl group Chemical group 0.000 claims description 37
238000002360 preparation method Methods 0.000 claims description 36
150000002431 hydrogen Chemical group 0.000 claims description 35
125000000753 cycloalkyl group Chemical group 0.000 claims description 31
206010028980 Neoplasm Diseases 0.000 claims description 30
125000003118 aryl group Chemical group 0.000 claims description 28
125000003545 alkoxy group Chemical group 0.000 claims description 27
201000011510 cancer Diseases 0.000 claims description 26
230000002062 proliferating effect Effects 0.000 claims description 23
239000003814 drug Substances 0.000 claims description 22
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 22
239000008194 pharmaceutical composition Substances 0.000 claims description 20
229910052736 halogen Inorganic materials 0.000 claims description 17
150000002367 halogens Chemical class 0.000 claims description 17
208000014951 hematologic disease Diseases 0.000 claims description 17
238000011282 treatment Methods 0.000 claims description 17
229910052757 nitrogen Inorganic materials 0.000 claims description 16
125000004093 cyano group Chemical group *C#N 0.000 claims description 15
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
239000008186 active pharmaceutical agent Substances 0.000 claims description 12
125000001425 triazolyl group Chemical group 0.000 claims description 12
125000002971 oxazolyl group Chemical group 0.000 claims description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
125000000335 thiazolyl group Chemical group 0.000 claims description 10
125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 8
208000019838 Blood disease Diseases 0.000 claims description 8
ZPMUGFCTFPDKHI-UHFFFAOYSA-N N-[5-(ethoxymethyl)-2-methylphenyl]-5-(4-pyrazol-1-ylphenyl)-1,3-thiazol-2-amine Chemical compound C(C)OCC=1C=CC(=C(C=1)NC=1SC(=CN=1)C1=CC=C(C=C1)N1N=CC=C1)C ZPMUGFCTFPDKHI-UHFFFAOYSA-N 0.000 claims description 8
206010035226 Plasma cell myeloma Diseases 0.000 claims description 8
208000018706 hematopoietic system disease Diseases 0.000 claims description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
125000002883 imidazolyl group Chemical group 0.000 claims description 8
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
125000003386 piperidinyl group Chemical group 0.000 claims description 8
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 8
150000003573 thiols Chemical class 0.000 claims description 8
ZBAFYGYLXHEICJ-UHFFFAOYSA-N 1-[4-[2-[5-(ethoxymethyl)-2-methylanilino]-1,3-oxazol-5-yl]phenyl]imidazolidin-2-one Chemical compound C(C)OCC=1C=CC(=C(C=1)NC=1OC(=CN=1)C1=CC=C(C=C1)N1C(NCC1)=O)C ZBAFYGYLXHEICJ-UHFFFAOYSA-N 0.000 claims description 7
HKHLLEPTTVBSDM-UHFFFAOYSA-N 1-[4-[2-[5-(ethoxymethyl)-2-methylanilino]-1,3-thiazol-4-yl]phenyl]imidazolidin-2-one Chemical compound C(C)OCC=1C=CC(=C(C=1)NC=1SC=C(N=1)C1=CC=C(C=C1)N1C(NCC1)=O)C HKHLLEPTTVBSDM-UHFFFAOYSA-N 0.000 claims description 7
201000003793 Myelodysplastic syndrome Diseases 0.000 claims description 7
PFQUSHNGTYPQTP-UHFFFAOYSA-N N-(5-methoxy-2-methylphenyl)-5-(6-pyrazol-1-ylpyridin-3-yl)-1,3-oxazol-2-amine Chemical compound COC=1C=CC(=C(C=1)NC=1OC(=CN=1)C=1C=NC(=CC=1)N1N=CC=C1)C PFQUSHNGTYPQTP-UHFFFAOYSA-N 0.000 claims description 7
CEJUBYJYSXUBGM-UHFFFAOYSA-N N-[5-(ethoxymethyl)-2-methylphenyl]-5-(3-methoxy-4-pyrazol-1-ylphenyl)-1,3-oxazol-2-amine Chemical compound C(C)OCC=1C=CC(=C(C=1)NC=1OC(=CN=1)C1=CC(=C(C=C1)N1N=CC=C1)OC)C CEJUBYJYSXUBGM-UHFFFAOYSA-N 0.000 claims description 7
125000004193 piperazinyl group Chemical group 0.000 claims description 7
125000003226 pyrazolyl group Chemical group 0.000 claims description 7
208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 claims description 6
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
208000001333 Colorectal Neoplasms Diseases 0.000 claims description 6
206010058467 Lung neoplasm malignant Diseases 0.000 claims description 6
206010025323 Lymphomas Diseases 0.000 claims description 6
208000005718 Stomach Neoplasms Diseases 0.000 claims description 6
206010017758 gastric cancer Diseases 0.000 claims description 6
201000007270 liver cancer Diseases 0.000 claims description 6
208000014018 liver 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
239000000546 pharmaceutical excipient Substances 0.000 claims description 6
201000011549 stomach cancer Diseases 0.000 claims description 6
125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 claims description 6
125000003831 tetrazolyl group Chemical group 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
206010061902 Pancreatic neoplasm Diseases 0.000 claims description 5
206010038389 Renal cancer Diseases 0.000 claims description 5
239000003937 drug carrier Substances 0.000 claims description 5
201000010536 head and neck cancer Diseases 0.000 claims description 5
208000014829 head and neck neoplasm Diseases 0.000 claims description 5
201000010982 kidney cancer Diseases 0.000 claims description 5
208000032839 leukemia Diseases 0.000 claims description 5
208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 5
201000001441 melanoma Diseases 0.000 claims description 5
201000000050 myeloid neoplasm Diseases 0.000 claims description 5
201000008968 osteosarcoma Diseases 0.000 claims description 5
201000002528 pancreatic cancer Diseases 0.000 claims description 5
208000008443 pancreatic carcinoma Diseases 0.000 claims description 5
208000024893 Acute lymphoblastic leukemia Diseases 0.000 claims description 4
208000014697 Acute lymphocytic leukaemia Diseases 0.000 claims description 4
208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 claims description 4
206010060862 Prostate cancer Diseases 0.000 claims description 4
208000000236 Prostatic Neoplasms Diseases 0.000 claims description 4
208000005017 glioblastoma Diseases 0.000 claims description 4
230000001537 neural effect Effects 0.000 claims description 4
208000006168 Ewing Sarcoma Diseases 0.000 claims description 3
201000010915 Glioblastoma multiforme Diseases 0.000 claims description 3
208000034578 Multiple myelomas Diseases 0.000 claims description 3
206010028537 myelofibrosis Diseases 0.000 claims description 3
QRCSISPIJNVFQQ-MRXNPFEDSA-N (5R)-1-[4-[2-[5-(ethoxymethyl)-2-methylanilino]-1,3-oxazol-5-yl]phenyl]-5-methylimidazolidin-2-one Chemical compound C(C)OCC=1C=CC(=C(C=1)NC=1OC(=CN=1)C1=CC=C(C=C1)N1C(NC[C@H]1C)=O)C QRCSISPIJNVFQQ-MRXNPFEDSA-N 0.000 claims description 2
KIECZPNABSVWNH-OAHLLOKOSA-N (5R)-1-[5-[2-[5-(ethoxymethyl)-2-methylanilino]-1,3-oxazol-5-yl]pyridin-2-yl]-5-methylimidazolidin-2-one Chemical compound C(C)OCC=1C=CC(=C(C=1)NC=1OC(=CN=1)C=1C=CC(=NC=1)N1C(NC[C@H]1C)=O)C KIECZPNABSVWNH-OAHLLOKOSA-N 0.000 claims description 2
GSYUXXIWIAFEEC-UHFFFAOYSA-N 1-(2-aminoethyl)-3-[4-[2-[5-(ethoxymethyl)-2-methylanilino]-1,3-oxazol-5-yl]phenyl]imidazolidin-2-one Chemical compound NCCN1C(N(CC1)C1=CC=C(C=C1)C1=CN=C(O1)NC1=C(C=CC(=C1)COCC)C)=O GSYUXXIWIAFEEC-UHFFFAOYSA-N 0.000 claims description 2
DQLSBFQGLKMGEA-UHFFFAOYSA-N 1-[4-[2-(5-methoxy-2-methylanilino)-1,3-thiazol-5-yl]phenyl]imidazolidin-2-one Chemical compound COC=1C=CC(=C(C=1)NC=1SC(=CN=1)C1=CC=C(C=C1)N1C(NCC1)=O)C DQLSBFQGLKMGEA-UHFFFAOYSA-N 0.000 claims description 2
SBJGWUJYRDHDBQ-UHFFFAOYSA-N 1-[4-[2-[3,5-bis(ethoxymethyl)anilino]-1,3-oxazol-5-yl]phenyl]imidazolidin-2-one Chemical compound CCOCC1=CC(NC2=NC=C(O2)C2=CC=C(C=C2)N2CCNC2=O)=CC(COCC)=C1 SBJGWUJYRDHDBQ-UHFFFAOYSA-N 0.000 claims description 2
FIJFTLZRJFJJHH-UHFFFAOYSA-N 1-[4-[2-[3-(ethoxymethyl)-5-(2-hydroxyethoxy)anilino]-1,3-oxazol-5-yl]phenyl]imidazolidin-2-one Chemical compound CCOCC1=CC(OCCO)=CC(NC2=NC=C(O2)C2=CC=C(C=C2)N2CCNC2=O)=C1 FIJFTLZRJFJJHH-UHFFFAOYSA-N 0.000 claims description 2
RQPXDZRYAPBRHH-UHFFFAOYSA-N 1-[4-[2-[3-(ethoxymethyl)-5-(2-methoxyethoxy)anilino]-1,3-oxazol-5-yl]phenyl]imidazolidin-2-one Chemical compound CCOCC1=CC(OCCOC)=CC(NC2=NC=C(O2)C2=CC=C(C=C2)N2CCNC2=O)=C1 RQPXDZRYAPBRHH-UHFFFAOYSA-N 0.000 claims description 2
LLZOOVAINRMGQZ-UHFFFAOYSA-N 1-[4-[2-[3-(ethoxymethyl)-5-methylanilino]-1,3-oxazol-5-yl]phenyl]imidazolidin-2-one Chemical compound C(C)OCC=1C=C(C=C(C=1)C)NC=1OC(=CN=1)C1=CC=C(C=C1)N1C(NCC1)=O LLZOOVAINRMGQZ-UHFFFAOYSA-N 0.000 claims description 2
LAKSUMNYPLRTDS-UHFFFAOYSA-N 1-[4-[2-[3-(ethoxymethyl)-5-methylanilino]-1,3-thiazol-4-yl]phenyl]imidazolidin-2-one Chemical compound C(C)OCC=1C=C(C=C(C=1)C)NC=1SC=C(N=1)C1=CC=C(C=C1)N1C(NCC1)=O LAKSUMNYPLRTDS-UHFFFAOYSA-N 0.000 claims description 2
QGBQAFISZCLPMZ-UHFFFAOYSA-N 1-[4-[2-[3-(ethoxymethyl)anilino]-1,3-oxazol-5-yl]phenyl]imidazolidin-2-one Chemical compound CCOCC1=CC=CC(NC2=NC=C(O2)C2=CC=C(C=C2)N2CCNC2=O)=C1 QGBQAFISZCLPMZ-UHFFFAOYSA-N 0.000 claims description 2
ZXWMOVQGEFDBGU-UHFFFAOYSA-N 1-[4-[2-[3-(ethoxymethyl)anilino]-1,3-thiazol-4-yl]phenyl]imidazolidin-2-one Chemical compound CCOCC1=CC=CC(NC2=NC(=CS2)C2=CC=C(C=C2)N2CCNC2=O)=C1 ZXWMOVQGEFDBGU-UHFFFAOYSA-N 0.000 claims description 2
HWDNOMODJUYGCR-UHFFFAOYSA-N 1-[4-[2-[5-(ethoxymethyl)-2-methylanilino]-1,3-oxazol-5-yl]phenyl]-3-(2-methoxyethyl)imidazolidin-2-one Chemical compound CCOCC1=CC(NC2=NC=C(O2)C2=CC=C(C=C2)N2CCN(CCOC)C2=O)=C(C)C=C1 HWDNOMODJUYGCR-UHFFFAOYSA-N 0.000 claims description 2
HFPQVVDIBFNORW-UHFFFAOYSA-N 1-[4-[2-[5-(ethoxymethyl)-2-methylanilino]-1,3-oxazol-5-yl]phenyl]-3-methylimidazolidin-2-one Chemical compound C(C)OCC=1C=CC(=C(C=1)NC=1OC(=CN=1)C1=CC=C(C=C1)N1C(N(CC1)C)=O)C HFPQVVDIBFNORW-UHFFFAOYSA-N 0.000 claims description 2
WPTJLPQUUQBCGM-UHFFFAOYSA-N 1-[4-[2-[5-(ethoxymethyl)-2-methylanilino]-1,3-oxazol-5-yl]phenyl]pyridin-2-one Chemical compound C(C)OCC=1C=CC(=C(C=1)NC=1OC(=CN=1)C1=CC=C(C=C1)N1C(C=CC=C1)=O)C WPTJLPQUUQBCGM-UHFFFAOYSA-N 0.000 claims description 2
ILSJJAHMDZLZCZ-UHFFFAOYSA-N 1-[4-[2-[5-(ethoxymethyl)-2-methylanilino]-1,3-oxazol-5-yl]phenyl]pyrrolidin-2-one Chemical compound C(C)OCC=1C=CC(=C(C=1)NC=1OC(=CN=1)C1=CC=C(C=C1)N1C(CCC1)=O)C ILSJJAHMDZLZCZ-UHFFFAOYSA-N 0.000 claims description 2
YYHQBSIXIZKFNY-UHFFFAOYSA-N 1-[4-[2-[5-(ethoxymethyl)-2-methylanilino]-1,3-thiazol-5-yl]phenyl]imidazolidin-2-one Chemical compound C(C)OCC=1C=CC(=C(C=1)NC=1SC(=CN=1)C1=CC=C(C=C1)N1C(NCC1)=O)C YYHQBSIXIZKFNY-UHFFFAOYSA-N 0.000 claims description 2
VOKVJCQSCHSFJP-UHFFFAOYSA-N 1-[4-[5-[5-(ethoxymethyl)-2-methylanilino]-1,2,4-thiadiazol-3-yl]phenyl]imidazolidin-2-one Chemical compound C(C)OCC=1C=CC(=C(C=1)NC1=NC(=NS1)C1=CC=C(C=C1)N1C(NCC1)=O)C VOKVJCQSCHSFJP-UHFFFAOYSA-N 0.000 claims description 2
XGESFNUMDHJAJS-UHFFFAOYSA-N 1-[4-[5-[5-(ethoxymethyl)-2-methylanilino]-1,3,4-oxadiazol-2-yl]phenyl]imidazolidin-2-one Chemical compound C(C)OCC=1C=CC(=C(C=1)NC1=NN=C(O1)C1=CC=C(C=C1)N1C(NCC1)=O)C XGESFNUMDHJAJS-UHFFFAOYSA-N 0.000 claims description 2
RFUULTLARLJBKO-UHFFFAOYSA-N 1-[5-[2-[5-(ethoxymethyl)-2-methylanilino]-1,3-oxazol-5-yl]pyridin-2-yl]imidazolidin-2-one Chemical compound CCOCC1=CC(NC2=NC=C(O2)C2=CN=C(C=C2)N2CCNC2=O)=C(C)C=C1 RFUULTLARLJBKO-UHFFFAOYSA-N 0.000 claims description 2
GVJOWQGYKUBCQE-UHFFFAOYSA-N 2-[4-[2-[5-(ethoxymethyl)-2-methylanilino]-1,3-oxazol-5-yl]phenyl]-4H-1,2,4-triazol-3-one Chemical compound C(C)OCC=1C=CC(=C(C=1)NC=1OC(=CN=1)C1=CC=C(C=C1)N1N=CNC1=O)C GVJOWQGYKUBCQE-UHFFFAOYSA-N 0.000 claims description 2
RRIGSUOVCYJHHP-UHFFFAOYSA-N 2-[[4-methyl-3-[[5-(4-pyrazol-1-ylphenyl)-1,3-oxazol-2-yl]amino]phenyl]methoxy]ethanol Chemical compound CC1=C(C=C(COCCO)C=C1)NC=1OC(=CN=1)C1=CC=C(C=C1)N1N=CC=C1 RRIGSUOVCYJHHP-UHFFFAOYSA-N 0.000 claims description 2
JSWUEYLOGRTPSD-UHFFFAOYSA-N 3-[4-[2-[5-(ethoxymethyl)-2-methylanilino]-1,3-oxazol-5-yl]phenyl]-1H-pyridin-2-one Chemical compound C(C)OCC=1C=CC(=C(C=1)NC=1OC(=CN=1)C1=CC=C(C=C1)C=1C(NC=CC=1)=O)C JSWUEYLOGRTPSD-UHFFFAOYSA-N 0.000 claims description 2
FZZLWAAVIZYJIV-UHFFFAOYSA-N 4-[4-[2-[5-(ethoxymethyl)-2-methylanilino]-1,3-oxazol-5-yl]phenyl]-3-methyl-1H-1,2,4-triazol-5-one Chemical compound C(C)OCC=1C=CC(=C(C=1)NC=1OC(=CN=1)C1=CC=C(C=C1)N1C(NN=C1C)=O)C FZZLWAAVIZYJIV-UHFFFAOYSA-N 0.000 claims description 2
GSBIYGCUXADINY-UHFFFAOYSA-N 4-methyl-N-(2-morpholin-4-ylethyl)-3-[[5-(4-pyrazol-1-ylphenyl)-1,3-oxazol-2-yl]amino]benzamide Chemical compound CC1=C(C=C(C(=O)NCCN2CCOCC2)C=C1)NC=1OC(=CN=1)C1=CC=C(C=C1)N1N=CC=C1 GSBIYGCUXADINY-UHFFFAOYSA-N 0.000 claims description 2
QMRAFYAFAQQRNJ-UHFFFAOYSA-N 4-methyl-N-[2-(4-methylpiperazin-1-yl)ethyl]-3-[[5-(4-pyrazol-1-ylphenyl)-1,3-oxazol-2-yl]amino]benzamide Chemical compound CC1=C(C=C(C(=O)NCCN2CCN(CC2)C)C=C1)NC=1OC(=CN=1)C1=CC=C(C=C1)N1N=CC=C1 QMRAFYAFAQQRNJ-UHFFFAOYSA-N 0.000 claims description 2
208000031261 Acute myeloid leukaemia Diseases 0.000 claims description 2
208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims description 2
206010058314 Dysplasia Diseases 0.000 claims description 2
BQVYNKAYYQVEDE-UHFFFAOYSA-N N,4-dimethyl-3-[[5-(4-pyrazol-1-ylphenyl)-1,3-oxazol-2-yl]amino]benzamide Chemical compound CC1=C(C=C(C(=O)NC)C=C1)NC=1OC(=CN=1)C1=CC=C(C=C1)N1N=CC=C1 BQVYNKAYYQVEDE-UHFFFAOYSA-N 0.000 claims description 2
TWXLTOPJWOZTJL-UHFFFAOYSA-N N-(5-methoxy-2-methylphenyl)-5-(4-pyrazol-1-ylphenyl)-1,3-oxazol-2-amine Chemical compound COC=1C=CC(=C(C=1)NC=1OC(=CN=1)C1=CC=C(C=C1)N1N=CC=C1)C TWXLTOPJWOZTJL-UHFFFAOYSA-N 0.000 claims description 2
MKFYLBQJGUUPPH-UHFFFAOYSA-N N-(5-methoxy-2-methylphenyl)-5-(4-pyrazol-1-ylphenyl)-1,3-thiazol-2-amine Chemical compound COC=1C=CC(=C(C=1)NC=1SC(=CN=1)C1=CC=C(C=C1)N1N=CC=C1)C MKFYLBQJGUUPPH-UHFFFAOYSA-N 0.000 claims description 2
JNBIUWYKWYDSPW-UHFFFAOYSA-N N-[2-[3-[4-[2-[5-(ethoxymethyl)-2-methylanilino]-1,3-oxazol-5-yl]phenyl]-2-oxoimidazolidin-1-yl]ethyl]acetamide Chemical compound C(C)OCC=1C=CC(=C(C=1)NC=1OC(=CN=1)C1=CC=C(C=C1)N1C(N(CC1)CCNC(C)=O)=O)C JNBIUWYKWYDSPW-UHFFFAOYSA-N 0.000 claims description 2
CIOSLVWJVLMMGY-UHFFFAOYSA-N N-[2-[[4-methyl-3-[[5-(4-pyrazol-1-ylphenyl)-1,3-oxazol-2-yl]amino]phenyl]methoxy]ethyl]acetamide Chemical compound CC1=C(C=C(COCCNC(C)=O)C=C1)NC=1OC(=CN=1)C1=CC=C(C=C1)N1N=CC=C1 CIOSLVWJVLMMGY-UHFFFAOYSA-N 0.000 claims description 2
PJYYCUOWUUOHEC-UHFFFAOYSA-N N-[2-methyl-5-(2-morpholin-4-ylethoxy)phenyl]-5-(4-pyrazol-1-ylphenyl)-1,3-oxazol-2-amine Chemical compound CC1=C(C=C(C=C1)OCCN1CCOCC1)NC=1OC(=CN=1)C1=CC=C(C=C1)N1N=CC=C1 PJYYCUOWUUOHEC-UHFFFAOYSA-N 0.000 claims description 2
NYTQNUSFRYFORG-UHFFFAOYSA-N N-[2-methyl-5-[(2-morpholin-4-ylethylamino)methyl]phenyl]-5-(4-pyrazol-1-ylphenyl)-1,3-oxazol-2-amine Chemical compound CC1=C(C=C(C=C1)CNCCN1CCOCC1)NC=1OC(=CN=1)C1=CC=C(C=C1)N1N=CC=C1 NYTQNUSFRYFORG-UHFFFAOYSA-N 0.000 claims description 2
QRSGFQDESJIFLU-UHFFFAOYSA-N N-[3,5-bis(ethoxymethyl)phenyl]-5-(4-pyrazol-1-ylphenyl)-1,3-oxazol-2-amine Chemical compound C(C)OCC=1C=C(C=C(C=1)COCC)NC=1OC(=CN=1)C1=CC=C(C=C1)N1N=CC=C1 QRSGFQDESJIFLU-UHFFFAOYSA-N 0.000 claims description 2
WUCHRJRDCNDMFS-UHFFFAOYSA-N N-[3-(ethoxymethyl)-5-methylphenyl]-5-(4-pyrazol-1-ylphenyl)-1,3-oxazol-2-amine Chemical compound C(C)OCC=1C=C(C=C(C=1)C)NC=1OC(=CN=1)C1=CC=C(C=C1)N1N=CC=C1 WUCHRJRDCNDMFS-UHFFFAOYSA-N 0.000 claims description 2
ANBIJEYNXHJRIP-UHFFFAOYSA-N N-[3-(ethoxymethyl)phenyl]-5-(4-pyrazol-1-ylphenyl)-1,3-oxazol-2-amine Chemical compound C(C)OCC=1C=C(C=CC=1)NC=1OC(=CN=1)C1=CC=C(C=C1)N1N=CC=C1 ANBIJEYNXHJRIP-UHFFFAOYSA-N 0.000 claims description 2
ZLVGNONNILHECM-UHFFFAOYSA-N N-[5-(2-aminoethoxymethyl)-2-methylphenyl]-5-(4-pyrazol-1-ylphenyl)-1,3-oxazol-2-amine Chemical compound NCCOCC=1C=CC(=C(C=1)NC=1OC(=CN=1)C1=CC=C(C=C1)N1N=CC=C1)C ZLVGNONNILHECM-UHFFFAOYSA-N 0.000 claims description 2
ZPQNZRRKCVTTFS-UHFFFAOYSA-N N-[5-(ethoxymethyl)-2-methylphenyl]-4-(4-pyrazol-1-ylphenyl)-1,3-thiazol-2-amine Chemical compound C(C)OCC=1C=CC(=C(C=1)NC=1SC=C(N=1)C1=CC=C(C=C1)N1N=CC=C1)C ZPQNZRRKCVTTFS-UHFFFAOYSA-N 0.000 claims description 2
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JP2017539023A 2015-02-05 2016-02-05 抗腫瘍活性を有する化合物 Active JP6713000B2 (ja)