JP2018530571A5 - - Google Patents

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Publication number: JP2018530571A5
Authority: JP; Japan
Prior art keywords: oxadiazol; amine; pyrimidin; difluoromethyl; cyclobutyl
Prior art date: 2016-10-11
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

Application number

JP2018518487A

Other languages

English (en)

Japanese (ja)

Other versions

JP2018530571A (ja

JP6697074B2 (ja

Filing date

2016-10-11

Publication date

2020-04-02

2016-10-11 Application filed filed Critical

2016-10-11 Priority claimed from PCT/KR2016/011355 external-priority patent/WO2017065473A1/en

2018-10-18 Publication of JP2018530571A publication Critical patent/JP2018530571A/ja

2020-04-02 Publication of JP2018530571A5 publication Critical patent/JP2018530571A5/ja

2020-05-20 Application granted granted Critical

2020-05-20 Publication of JP6697074B2 publication Critical patent/JP6697074B2/ja

Status Active legal-status Critical Current

2036-10-11 Anticipated expiration legal-status Critical

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125000000217 alkyl group Chemical group 0.000 claims description 15
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 8
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 3
125000003118 aryl group Chemical group 0.000 claims description 3
125000001072 heteroaryl group Chemical group 0.000 claims description 3
150000001875 compounds Chemical class 0.000 claims 19
150000003839 salts Chemical class 0.000 claims 11
230000003287 optical effect Effects 0.000 claims 10
-1 oxadiazoleamine derivative compound Chemical class 0.000 claims 10
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 8
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 6
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 6
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 6
201000010099 disease Diseases 0.000 claims 6
102000011427 Histone Deacetylase 6 Human genes 0.000 claims 4
108010023925 Histone Deacetylase 6 Proteins 0.000 claims 4
FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 claims 3
IWLBNXJONYNAEW-UHFFFAOYSA-N 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-(1-phenylcyclobutyl)pyrimidin-2-amine Chemical compound FC(C1=NN=C(O1)C=1C=NC(=NC=1)NC1(CCC1)C1=CC=CC=C1)F IWLBNXJONYNAEW-UHFFFAOYSA-N 0.000 claims 3
JPVLSBUZEKWGHX-UHFFFAOYSA-N 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-(1-pyridin-2-ylcyclobutyl)pyrimidin-2-amine Chemical compound FC(C1=NN=C(O1)C=1C=NC(=NC=1)NC1(CCC1)C1=NC=CC=C1)F JPVLSBUZEKWGHX-UHFFFAOYSA-N 0.000 claims 3
XYEUQTIOPNGIBI-UHFFFAOYSA-N 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-fluorophenyl)cyclobutyl]pyrimidin-2-amine Chemical compound FC(C1=NN=C(O1)C=1C=NC(=NC=1)NC1(CCC1)C1=C(C=CC=C1)F)F XYEUQTIOPNGIBI-UHFFFAOYSA-N 0.000 claims 3
HNEATXXHHGDQQF-UHFFFAOYSA-N 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(3-fluorophenyl)cyclobutyl]pyrimidin-2-amine Chemical compound FC(C1=NN=C(O1)C=1C=NC(=NC=1)NC1(CCC1)C1=CC(=CC=C1)F)F HNEATXXHHGDQQF-UHFFFAOYSA-N 0.000 claims 3
KQAYHVMWQWFKFV-UHFFFAOYSA-N N-[1-(2-chlorophenyl)cyclobutyl]-5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]pyrimidin-2-amine Chemical compound ClC1=C(C=CC=C1)C1(CCC1)NC1=NC=C(C=N1)C=1OC(=NN=1)C(F)F KQAYHVMWQWFKFV-UHFFFAOYSA-N 0.000 claims 3
DLAYBQQQQIQTMD-UHFFFAOYSA-N N-[1-(3-chlorophenyl)cyclobutyl]-5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]pyrimidin-2-amine Chemical compound ClC=1C=C(C=CC=1)C1(CCC1)NC1=NC=C(C=N1)C=1OC(=NN=1)C(F)F DLAYBQQQQIQTMD-UHFFFAOYSA-N 0.000 claims 3
150000001412 amines Chemical class 0.000 claims 3
HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 claims 3
239000003814 drug Substances 0.000 claims 3
229940079593 drug Drugs 0.000 claims 3
230000005764 inhibitory process Effects 0.000 claims 3
239000008194 pharmaceutical composition Substances 0.000 claims 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 3
229930192474 thiophene Natural products 0.000 claims 3
NZUUXQSBKZPFKK-UHFFFAOYSA-N 4-piperazin-1-ylmorpholine Chemical compound C1CNCCN1N1CCOCC1 NZUUXQSBKZPFKK-UHFFFAOYSA-N 0.000 claims 2
OHUXVGIHPZKNEF-UHFFFAOYSA-N 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-(1-phenylcyclopentyl)pyrimidin-2-amine Chemical compound FC(C1=NN=C(O1)C=1C=NC(=NC=1)NC1(CCCC1)C1=CC=CC=C1)F OHUXVGIHPZKNEF-UHFFFAOYSA-N 0.000 claims 2
IRFXHUXQYBARTM-UHFFFAOYSA-N 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-(1-phenylcyclopropyl)pyrimidin-2-amine Chemical compound FC(C1=NN=C(O1)C=1C=NC(=NC=1)NC1(CC1)C1=CC=CC=C1)F IRFXHUXQYBARTM-UHFFFAOYSA-N 0.000 claims 2
URIYDONQDHNSLI-UHFFFAOYSA-N 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(3,4-difluorophenyl)cyclopropyl]pyrimidin-2-amine Chemical compound FC(C1=NN=C(O1)C=1C=NC(=NC=1)NC1(CC1)C1=CC(=C(C=C1)F)F)F URIYDONQDHNSLI-UHFFFAOYSA-N 0.000 claims 2
NYWYVJDCLKGRIO-UHFFFAOYSA-N 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(3-methoxyphenyl)cyclobutyl]pyrimidin-2-amine Chemical compound FC(C1=NN=C(O1)C=1C=NC(=NC=1)NC1(CCC1)C1=CC(=CC=C1)OC)F NYWYVJDCLKGRIO-UHFFFAOYSA-N 0.000 claims 2
XWIRZMLXWLSWLU-UHFFFAOYSA-N 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(4-fluorophenyl)cyclobutyl]pyrimidin-2-amine Chemical compound FC(C1=NN=C(O1)C=1C=NC(=NC=1)NC1(CCC1)C1=CC=C(C=C1)F)F XWIRZMLXWLSWLU-UHFFFAOYSA-N 0.000 claims 2
IBSOZXONCGPOID-UHFFFAOYSA-N 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(4-methoxyphenyl)cyclobutyl]pyrimidin-2-amine Chemical compound FC(C1=NN=C(O1)C=1C=NC(=NC=1)NC1(CCC1)C1=CC=C(C=C1)OC)F IBSOZXONCGPOID-UHFFFAOYSA-N 0.000 claims 2
ZCVCIOKWHGPURY-UHFFFAOYSA-N N-[1-(4-chlorophenyl)cyclobutyl]-5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]pyrimidin-2-amine Chemical compound ClC1=CC=C(C=C1)C1(CCC1)NC1=NC=C(C=N1)C=1OC(=NN=1)C(F)F ZCVCIOKWHGPURY-UHFFFAOYSA-N 0.000 claims 2
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 2
239000004480 active ingredient Substances 0.000 claims 2
OMTYOKNFBKZRCX-UHFFFAOYSA-N 3-[1-[[5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]pyrimidin-2-yl]amino]cyclobutyl]phenol Chemical compound FC(C1=NN=C(O1)C=1C=NC(=NC=1)NC1(CCC1)C=1C=C(C=CC=1)O)F OMTYOKNFBKZRCX-UHFFFAOYSA-N 0.000 claims 1
KQTGCJMBUBYSLL-UHFFFAOYSA-N 4-piperidin-1-ylmorpholine Chemical compound C1CCCCN1N1CCOCC1 KQTGCJMBUBYSLL-UHFFFAOYSA-N 0.000 claims 1
GVSBHWJWYJPQIM-UHFFFAOYSA-N 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-(1-phenylcyclohexyl)pyrimidin-2-amine Chemical compound FC(C1=NN=C(O1)C=1C=NC(=NC=1)NC1(CCCCC1)C1=CC=CC=C1)F GVSBHWJWYJPQIM-UHFFFAOYSA-N 0.000 claims 1
OSAQOVAKOFTYCZ-UHFFFAOYSA-N 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-(1-pyridin-3-ylcyclobutyl)pyrimidin-2-amine Chemical compound FC(C1=NN=C(O1)C=1C=NC(=NC=1)NC1(CCC1)C=1C=NC=CC=1)F OSAQOVAKOFTYCZ-UHFFFAOYSA-N 0.000 claims 1
NPTDMWYUZVJUMM-UHFFFAOYSA-N 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-(1-thiophen-2-ylcyclopropyl)pyrimidin-2-amine Chemical compound FC(C1=NN=C(O1)C=1C=NC(=NC=1)NC1(CC1)C=1SC=CC=1)F NPTDMWYUZVJUMM-UHFFFAOYSA-N 0.000 claims 1
CAJKPVLLDPXNAN-UHFFFAOYSA-N 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-(1-thiophen-3-ylcyclobutyl)pyrimidin-2-amine Chemical compound FC(C1=NN=C(O1)C=1C=NC(=NC=1)NC1(CCC1)C1=CSC=C1)F CAJKPVLLDPXNAN-UHFFFAOYSA-N 0.000 claims 1
VTTTXOGPYMPVPW-UHFFFAOYSA-N 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2,3-difluorophenyl)cyclobutyl]pyrimidin-2-amine Chemical compound FC(C1=NN=C(O1)C=1C=NC(=NC=1)NC1(CCC1)C1=C(C(=CC=C1)F)F)F VTTTXOGPYMPVPW-UHFFFAOYSA-N 0.000 claims 1
IONASXYPOBMBBE-UHFFFAOYSA-N 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2,4,5-trifluorophenyl)cyclobutyl]pyrimidin-2-amine Chemical compound FC(C1=NN=C(O1)C=1C=NC(=NC=1)NC1(CCC1)C1=C(C=C(C(=C1)F)F)F)F IONASXYPOBMBBE-UHFFFAOYSA-N 0.000 claims 1
ITYAJMHGAQGGOR-UHFFFAOYSA-N 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2,4-difluorophenyl)cyclobutyl]pyrimidin-2-amine Chemical compound FC(C1=NN=C(O1)C=1C=NC(=NC=1)NC1(CCC1)C1=C(C=C(C=C1)F)F)F ITYAJMHGAQGGOR-UHFFFAOYSA-N 0.000 claims 1
OLGXMCAJCVJOOS-UHFFFAOYSA-N 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2,4-difluorophenyl)cyclopropyl]pyrimidin-2-amine Chemical compound FC(C1=NN=C(O1)C=1C=NC(=NC=1)NC1(CC1)C1=C(C=C(C=C1)F)F)F OLGXMCAJCVJOOS-UHFFFAOYSA-N 0.000 claims 1
AQSCSJFKJJCULX-UHFFFAOYSA-N 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2,5-difluorophenyl)cyclobutyl]pyrimidin-2-amine Chemical compound FC(C1=NN=C(O1)C=1C=NC(=NC=1)NC1(CCC1)C1=C(C=CC(=C1)F)F)F AQSCSJFKJJCULX-UHFFFAOYSA-N 0.000 claims 1
POIZTOQUMFNAGU-UHFFFAOYSA-N 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2,6-difluorophenyl)cyclobutyl]pyrimidin-2-amine Chemical compound FC(C1=NN=C(O1)C=1C=NC(=NC=1)NC1(CCC1)C1=C(C=CC=C1F)F)F POIZTOQUMFNAGU-UHFFFAOYSA-N 0.000 claims 1
YPLIKXPJWPAMHH-UHFFFAOYSA-N 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-fluorophenyl)cyclopropyl]pyrimidin-2-amine Chemical compound FC(C1=NN=C(O1)C=1C=NC(=NC=1)NC1(CC1)C1=C(C=CC=C1)F)F YPLIKXPJWPAMHH-UHFFFAOYSA-N 0.000 claims 1
CVFUNOSWWHZQPL-UHFFFAOYSA-N 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-methoxyphenyl)cyclopropyl]pyrimidin-2-amine Chemical compound FC(C1=NN=C(O1)C=1C=NC(=NC=1)NC1(CC1)C1=C(C=CC=C1)OC)F CVFUNOSWWHZQPL-UHFFFAOYSA-N 0.000 claims 1
ITTIVAGNYVVBML-UHFFFAOYSA-N 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-methylphenyl)cyclobutyl]pyrimidin-2-amine Chemical compound FC(C1=NN=C(O1)C=1C=NC(=NC=1)NC1(CCC1)C1=C(C=CC=C1)C)F ITTIVAGNYVVBML-UHFFFAOYSA-N 0.000 claims 1
XJILLSGCZRFZGN-UHFFFAOYSA-N 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-methylphenyl)cyclopropyl]pyrimidin-2-amine Chemical compound FC(C1=NN=C(O1)C=1C=NC(=NC=1)NC1(CC1)C1=C(C=CC=C1)C)F XJILLSGCZRFZGN-UHFFFAOYSA-N 0.000 claims 1
GWHHJXUXHJKYOF-UHFFFAOYSA-N 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(3,4-difluorophenyl)cyclobutyl]pyrimidin-2-amine Chemical compound FC(C1=NN=C(O1)C=1C=NC(=NC=1)NC1(CCC1)C1=CC(=C(C=C1)F)F)F GWHHJXUXHJKYOF-UHFFFAOYSA-N 0.000 claims 1
TWHOWWKLLANQQY-UHFFFAOYSA-N 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(3,5-difluorophenyl)cyclobutyl]pyrimidin-2-amine Chemical compound FC(C1=NN=C(O1)C=1C=NC(=NC=1)NC1(CCC1)C1=CC(=CC(=C1)F)F)F TWHOWWKLLANQQY-UHFFFAOYSA-N 0.000 claims 1
YVEQMFKNMMXIMZ-UHFFFAOYSA-N 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(3,5-difluorophenyl)cyclopropyl]pyrimidin-2-amine Chemical compound FC(C1=NN=C(O1)C=1C=NC(=NC=1)NC1(CC1)C1=CC(=CC(=C1)F)F)F YVEQMFKNMMXIMZ-UHFFFAOYSA-N 0.000 claims 1
HCTAUPUREYXKFK-UHFFFAOYSA-N 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(3-fluorophenyl)cyclopropyl]pyrimidin-2-amine Chemical compound FC(C1=NN=C(O1)C=1C=NC(=NC=1)NC1(CC1)C1=CC(=CC=C1)F)F HCTAUPUREYXKFK-UHFFFAOYSA-N 0.000 claims 1
LTPUXKCCKVVLJB-UHFFFAOYSA-N 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(3-methoxyphenyl)cyclopropyl]pyrimidin-2-amine Chemical compound FC(C1=NN=C(O1)C=1C=NC(=NC=1)NC1(CC1)C1=CC(=CC=C1)OC)F LTPUXKCCKVVLJB-UHFFFAOYSA-N 0.000 claims 1
QXCJONADAMMDRA-UHFFFAOYSA-N 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(3-methylphenyl)cyclobutyl]pyrimidin-2-amine Chemical compound FC(C1=NN=C(O1)C=1C=NC(=NC=1)NC1(CCC1)C=1C=C(C=CC=1)C)F QXCJONADAMMDRA-UHFFFAOYSA-N 0.000 claims 1
DNRQRGVRWPIVBO-UHFFFAOYSA-N 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(4-fluoro-3-morpholin-4-ylphenyl)cyclobutyl]pyrimidin-2-amine Chemical compound FC(C1=NN=C(O1)C=1C=NC(=NC=1)NC1(CCC1)C1=CC(=C(C=C1)F)N1CCOCC1)F DNRQRGVRWPIVBO-UHFFFAOYSA-N 0.000 claims 1
NJAAVNSOZGGXFC-UHFFFAOYSA-N 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(4-fluorophenyl)cyclopropyl]pyrimidin-2-amine Chemical compound FC(C1=NN=C(O1)C=1C=NC(=NC=1)NC1(CC1)C1=CC=C(C=C1)F)F NJAAVNSOZGGXFC-UHFFFAOYSA-N 0.000 claims 1
XTEWTDPLEBUYHB-UHFFFAOYSA-N 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(4-methoxyphenyl)cyclopropyl]pyrimidin-2-amine Chemical compound FC(C1=NN=C(O1)C=1C=NC(=NC=1)NC1(CC1)C1=CC=C(C=C1)OC)F XTEWTDPLEBUYHB-UHFFFAOYSA-N 0.000 claims 1
GDYIQRPIWKNMRD-UHFFFAOYSA-N 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(4-methylphenyl)cyclobutyl]pyrimidin-2-amine Chemical compound FC(C1=NN=C(O1)C=1C=NC(=NC=1)NC1(CCC1)C1=CC=C(C=C1)C)F GDYIQRPIWKNMRD-UHFFFAOYSA-N 0.000 claims 1
CKZHCKRAKJWEOT-UHFFFAOYSA-N 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(4-piperidin-1-ylphenyl)cyclobutyl]pyrimidin-2-amine Chemical compound FC(C1=NN=C(O1)C=1C=NC(=NC=1)NC1(CCC1)C1=CC=C(C=C1)N1CCCCC1)F CKZHCKRAKJWEOT-UHFFFAOYSA-N 0.000 claims 1
GRJVDOLELSBCEX-UHFFFAOYSA-N 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-[(4-methylphenyl)sulfonylmethyl]cyclobutyl]pyrimidin-2-amine Chemical compound FC(C1=NN=C(O1)C=1C=NC(=NC=1)NC1(CCC1)CS(=O)(=O)C1=CC=C(C)C=C1)F GRJVDOLELSBCEX-UHFFFAOYSA-N 0.000 claims 1
BBIYXQBIVALMDC-UHFFFAOYSA-N 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-[2-(trifluoromethoxy)phenyl]cyclobutyl]pyrimidin-2-amine Chemical compound FC(C1=NN=C(O1)C=1C=NC(=NC=1)NC1(CCC1)C1=C(C=CC=C1)OC(F)(F)F)F BBIYXQBIVALMDC-UHFFFAOYSA-N 0.000 claims 1
MGMSBHAPWDRJFO-UHFFFAOYSA-N 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-[2-(trifluoromethyl)phenyl]cyclobutyl]pyrimidin-2-amine Chemical compound FC(C1=NN=C(O1)C=1C=NC(=NC=1)NC1(CCC1)C1=C(C=CC=C1)C(F)(F)F)F MGMSBHAPWDRJFO-UHFFFAOYSA-N 0.000 claims 1
RQQKXOMZYCDEAI-UHFFFAOYSA-N 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-[3-(trifluoromethyl)phenyl]cyclobutyl]pyrimidin-2-amine Chemical compound FC(C1=NN=C(O1)C=1C=NC(=NC=1)NC1(CCC1)C1=CC(=CC=C1)C(F)(F)F)F RQQKXOMZYCDEAI-UHFFFAOYSA-N 0.000 claims 1
JUEKLLPPPOBEDZ-UHFFFAOYSA-N 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-[3-(trifluoromethyl)phenyl]cyclopropyl]pyrimidin-2-amine Chemical compound FC(C1=NN=C(O1)C=1C=NC(=NC=1)NC1(CC1)C1=CC(=CC=C1)C(F)(F)F)F JUEKLLPPPOBEDZ-UHFFFAOYSA-N 0.000 claims 1
LETBEEUWGHYDCD-UHFFFAOYSA-N 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-[3-[1-(oxetan-3-yl)piperidin-4-yl]phenyl]cyclobutyl]pyrimidin-2-amine Chemical compound FC(C1=NN=C(O1)C=1C=NC(=NC=1)NC1(CCC1)C1=CC(=CC=C1)C1CCN(CC1)C1COC1)F LETBEEUWGHYDCD-UHFFFAOYSA-N 0.000 claims 1
HUINJMVBFMZLCP-UHFFFAOYSA-N 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-[4-(trifluoromethoxy)phenyl]cyclobutyl]pyrimidin-2-amine Chemical compound FC(C1=NN=C(O1)C=1C=NC(=NC=1)NC1(CCC1)C1=CC=C(C=C1)OC(F)(F)F)F HUINJMVBFMZLCP-UHFFFAOYSA-N 0.000 claims 1
FUYRLGWIEZIQTN-UHFFFAOYSA-N 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-[4-(trifluoromethyl)phenyl]cyclobutyl]pyrimidin-2-amine Chemical compound FC(C1=NN=C(O1)C=1C=NC(=NC=1)NC1(CCC1)C1=CC=C(C=C1)C(F)(F)F)F FUYRLGWIEZIQTN-UHFFFAOYSA-N 0.000 claims 1
FASUTFGXOCYZBQ-UHFFFAOYSA-N 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-[4-(trifluoromethyl)phenyl]cyclopropyl]pyrimidin-2-amine Chemical compound FC(C1=NN=C(O1)C=1C=NC(=NC=1)NC1(CC1)C1=CC=C(C=C1)C(F)(F)F)F FASUTFGXOCYZBQ-UHFFFAOYSA-N 0.000 claims 1
HMKSUSGISGIFSI-UHFFFAOYSA-N 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-[4-[1-(oxetan-3-yl)piperidin-4-yl]phenyl]cyclobutyl]pyrimidin-2-amine Chemical compound FC(C1=NN=C(O1)C=1C=NC(=NC=1)NC1(CCC1)C1=CC=C(C=C1)C1CCN(CC1)C1COC1)F HMKSUSGISGIFSI-UHFFFAOYSA-N 0.000 claims 1
GARYREBVDMJCRV-UHFFFAOYSA-N 5-[5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-[3-(trifluoromethyl)phenyl]cyclobutyl]pyrimidin-2-amine Chemical compound FC(C1=NN=C(O1)C=1C=NC(=NC=1)NC1(CCC1)C1=CC(=CC=C1)C(F)(F)F)(F)F GARYREBVDMJCRV-UHFFFAOYSA-N 0.000 claims 1
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JP2018518487A 2015-10-12 2016-10-11 ヒストン脱アセチル化酵素６阻害剤としてのオキサジアゾールアミン誘導体化合物及びこれを含有する薬剤学的組成物 Active JP6697074B2 (ja)

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KR10-2015-0142014		2015-10-12
PCT/KR2016/011355 WO2017065473A1 (en)	2015-10-12	2016-10-11	Oxadiazole amine derivative compounds as histone deacetylase 6 inhibitor, and the pharmaceutical composition comprising the same

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AU (1)	AU2016338118B2 (2)
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